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$270

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Shelleys Rooftop Hideaway

Key West condo
2 BR / 3 BA / Sleeps 4 | Quick view
Excellent3 Reviews

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Reviews

(3)

Upper Duval is the best! A few steps away from the Southernmost pt & beaches,great restaurants,art galleries, Louies backyard,and Blue Heaven. A few more steps from Mallory sq, Sloppy Joes, Smokin tuna, the pier restaurants, entertainment day and night. Have the best of both worlds, be in the middle of all key west …
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible - ask

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Reviews

(3)

Great location

Left on Dec 31, 2013 for a stay in December 2013

Really enjoyed staying at Shelleys Rooftop. Far enough down Duval St. to be away from the crowds but just a walk away to the crowds and popular bars. Spent Christmas with family and friends in Key West and fun time had by all. Great pool at the condo and great people watching area at the "ledge" over looking Duval St. Condo was perfect for the 5 of us especially with 2 1/2 baths. When I …

$218

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Newton Street Hideaway: A secluded one bedroom

Key West house
1 BR / 2 BA / Sleeps 2 | Quick view
Excellent2 Reviews

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Reviews

(2)

30 DAY MINIMUM RENTAL The meadows of Key West is a lovely, quiet and historic neighborhood located just behind Old Town Key West and known for it's tranquil tree lined streets. Centrally located on the island, yet far enough away from the hustle bustle of Duval, this is truly a wonderful locale for an extended stay …
  • Internet Access
  • A/C or climate control
  • Deck
  • Parking
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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Reviews

(2)

A Second Home

Left on Jun 17, 2011 for a stay in May 2011

We have stayed at the Newton Street Hideaway for several years, and, as soon as we open the door, it's just like coming home! It's fun to spot the improvements made by the owners since our previous visit (this time there were new rugs in the kitchen, and stools at the breakfast bar) The house is situated in the quiet residential area known as The Meadows, on the far side of White Street, but it …

$303

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Angela Cottage: A hideaway in Old Town

Key West house
2 BR / 2 BA / Sleeps 4 | Quick view
Excellent2 Reviews

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Reviews

(2)

30 DAY MINIMUM RENTAL This cute cottage just off of Frances Street is a great hideaway, still in Old Town, but a good central location to get to the Historic seaport or new town. The light & airy combined living/dining area with its soft color toned furnishings, hardwood floors & many windows create a relaxing Key …
  • Internet Access
  • A/C or climate control
  • Deck
  • Grill
  • Linens Provided
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

Outstanding

Left on Jun 26, 2009 for a stay in March 2009

I have rented the Angla Cottage for the past three seasons. The house is very comfortable with space for guests in a separate portion of thje house. Swimming pool is great, and outdoor dining area is outstanding for any meal. The kitchen is new and all the necessary pots and pans are present.

$225

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Key West condo! Bring your own boat!

Key West condo
2 BR / 2 BA / Sleeps 6 | Quick view
Very Good4 Reviews

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Reviews

(4)

Come down and take part in in Key West's many fishing tournaments this summer! No docking fees at this condo where you can park your boat in the spacious lot and keep your car covered in your reserved spot under the building. Make memories the whole family will cherish in this great family friendly condo in Key …
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly - elevator access
  • Wheelchair accessible

Details

Reviews

(4)

Lovely, well presented

Left on Oct 25, 2013 for a stay in October 2013

A very nice accommodation. Very well thought out and presented. Faultlessly clean and well maintained. Pauly was quite kind and took great pains to ensure our complete satisfaction.

$175

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Sail Florida Adventures | Days and Sunset sails

Key West house
2 BR / 1 BA / Sleeps 4 | Quick view
Excellent8 Reviews

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Reviews

(8)

What a unique way to spend time on the water. Its not a 5 star hotel but you will have a nice clean private chartered boat on the water. Get ready for a unique vacation that others will envy. Boat is a 2003 Beneteau 331, while the boat is dockside the marina has electricity, water and Internet. Fully functional …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • A/C or climate control
  • Suitable for children - ask

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Reviews

(8)

Very Relaxing

Left on Feb 23, 2014 for a stay in February 2014

The boat is exactly as stated and I found the accommodations very pleasant and comfortable . We stayed three nights. However some people might not as there are very "tight quarters" on relatively small boats. And I would not recommend it to individuals with mobility issues. The marina is very safe and the clubhouse and pool very nice. Our host was very nice and met us at the boat and …

$265

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Paradise Found

Key West condo
2 BR / 2 BA / Sleeps 6 | Quick view
Excellent5 Reviews

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Reviews

(5)

Paradise found reservations must begin and end on a Saturday. You feel it the moment you arrive. It's a rhythm. A rhythm set into motion over a century ago by pirates, artists, writers and other champions of leisure. Today that same rhythm beckons you to discover the charm and grace of Old Key West in a new and …
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Sauna
  • Internet Access
  • Suitable for the elderly
  • Wheelchair accessible

Details

Reviews

(5)

Wonderful place off the beaten path

Left on Jun 20, 2011 for a stay in August 2010

The condo it's self was wonderful could stand a little updating (Bed) and outside but were painting and fixing when we were there, The grounds were very beautiful
But we really enjoyed the pool and the view was spectacular
could not walk to everything definitely need a car
Mike was very nice to work with great place overall

$243

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Casa Del Sol, a Key West Vacation (Truman Annex)

Key West house
2 BR / 3 BA / Sleeps 6 | Quick view
Excellent24 Reviews

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Reviews

(24)

Welcome to Casa Del Sol, a Key West Vacation...your very own luxurious and elegantly appointed 2 bedroom and 2.5 bath townhome with private carport... part of 45 lushly landscaped acres in Truman Annex. As part of President's Walk townhomes in gated Truman Annex, this premier waterfront community is bordered on one …
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly - ask

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Reviews

(24)

Comfortable, cozy & perfectly located - a great place to stay!

Left on Jul 18, 2013 for a stay in June 2013

We stayed for a week in June, and enjoyed it so much that we extended the stay 3 more days. This is a beautiful and cozy rental with quick access to everything in the Keys we wanted to do and see. We had every amenity we needed, to the point that we felt like we were at home. The owners made us feel the same way - as family instead of strangers renting their space. We are already looking …

$186

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Artist Cottage in Truman Annex

Key West condo
2 BR / 1 BA / Sleeps 4 | Quick view
Excellent8 Reviews

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Reviews

(8)

Truman Annex Best Location in Town!! 2 Bedroom 1 Bath ground floor Shipyard Condo. This beautiful townhome sits on a private quiet walking lane and is just a 5 minute walk to downtown where you will find Key West's famous bars and shopping. Also a 10 minute walk to Ft. Zachary Taylor, our beautiful beach..great …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for children
  • Suitable for the elderly

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Reviews

(8)

Thank you for the memories!

Left on Sep 12, 2010 for a stay in July 2010

Dear Susan & staff,

We wanted to take this opportunity to thank you for our amazing stay this summer. The artist Cottage was just immaculate and we were very impressed. It was a perfect place for us and our boys for our summer vacation. We've been to Key West before, and this place by far surpasses all the other places we have stayed. Next time we plan a trip to Key West, you can guarantee we …

$229

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Best Location, 1/2 Block to Duval, Bimini Suite

Key West condo
2 BR / 2 BA / Sleeps 5 | Quick view
Excellent15 Reviews

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Reviews

(15)

Located in the heart of Old Town, this split 2 Bedroom plan is just blocks from everything Key West has to offer. The famous Southernmost Point, Hemingway House, Lighthouse, Beaches and more. Just 1/2 block from Duval Street. Completely updated for your comfort and convience with new furnitire, bedding, decor and …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for the elderly

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Reviews

(15)

location! location! location!

Left on Apr 24, 2014 for a stay in April 2014

The location was perfect for going out in Key west! I stayed with 3 other friends and there was plenty of space. The place was clean the bathrooms were nice. The only thing that was a bit of a pain was the parking. its just a driveway you share with the rest of the guests. So one night/ eve I was out and had to go back and move the car so another guest could leave. Aside form that the place was …

$295

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Spectacular Atlantic Ocean View Condo

Key West condo
2 BR / 2 BA / Sleeps 6 | Quick view
Excellent16 Reviews

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Reviews

(16)

************************************************************************************************* TAKE 20%+ OFF: -- Stay July 20 - 23 (3 nights) and pay a reduced rate of $800 for all three nights instead of $1,020. -- Note, taxes and fees will be added to all rates…
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Housekeeping Optional
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - elevator access
  • Wheelchair accessible

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Reviews

(16)

Unbelievable view!

Left on Mar 15, 2014 for a stay in February 2014

A gorgeous retreat from the hustle and bustle of everyday life. Our family of 2 grown ups and 2 kids had a wonderful time at this place, very nicely decorated and appointed with all the necessities. Great kitchen, nice bedrooms, one with a spectacular view and one with its own couch and seating area. The balcony is to die for. Set away from the business of the center of Key West so there's a 10 …

$259

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Steps to Duval, Old Town Charm -Grand Bahama Suite

Key West condo
3 BR / 2 BA / Sleeps 8 | Quick view
Excellent15 Reviews

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Reviews

(15)

Just steps away from shops, restaurants, and the excitement of Duval Street, yet set on a quiet side street in a world of its own. With 3 bedrooms and 2 Baths, The Grand Bahama Suite has plenty of room for a large gathering or group of friends. Experience endless sunshine and the incomparable charm found only in …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for the elderly - ask

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Reviews

(15)

Amazing location!!!

Left on Nov 05, 2013 for a stay in August 2013

Location was wonderful one block block of Duval street, 3 of us shared the rental each had their own bedroom and there were 2 baths, and we 3 grown men having the 2nd bath was very valuable. The backyard area while not being the most beautiful thing in the world was still a great place to sit out and have a few drinks with friends old and new, our upstairs neighbors were great people and we …

$210

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2 bedroom Condo Presented Key West Style

Key West condo
2 BR / 2 BA / Sleeps 6 | Quick view
Excellent41 Reviews

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Reviews

(41)

This is a non-smoking condo (smoking on the balcony only) with that "home away from home" appeal. My condo is reasonably priced and includes 1 king bed suite and 1 queen bed suite and a sofabed. All bed linens are provided. Wait there is more, 2 full baths, fully equipped kitchen (dine in/dine out), cental air with …
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly - elevator access
  • Wheelchair accessible - ask

Details

Reviews

(41)

spacious, clean, quiet, excellent value for the price.

Left on Sep 20, 2012 for a stay in August 2012

We stayed in late august and had a wonderful time here. Very spacious with 2 bedrooms ,2 spacious bathrooms and a a large fully equipped kitchen. The kitchen has everything you will need,pots,pans, toaster,coffeemaker,dishwasher,microwave,etc.,etc. You feel at home. The master bedroom has a walk in closet,in suite bathroom. The smaller bedroom has queen bed. Both rooms have their own TVs. There …

$250

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Tee by the Sea - Luxury 2/3 condo - 7 Bikes FREE

Key West condo
2 BR / 3 BA / Sleeps 6 | Quick view
Excellent56 Reviews

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Reviews

(56)

All new luxury 2 bedroom / 2 1/2 bath condo of 1100 sq. ft. less than 1/2 mile outside of Key West in NEW gated community, including huge heated pool, clubhouse with fitness center. Sleeps up to 6 with a queen bed in each room and a queen sleeper/sofa in LR. We are 4 miles from Duval St. and 2 miles from the beach…
  • Wireless Internet
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(56)

Perfect Escape

Left on Jun 28, 2009 for a stay in April 2009

From the moment we walked in the door we loved this condo! It was clean, well decorated and looked brand new. Everything was very nice quality and in perfect condition. The bedding was wonderful! We loved the pool. There was hardly anyone around when we were there. We did meet some nice people there though. It was a great place to kick back and relax. We rode the bikes to the store down the …

$260

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Elegant, Two Bedroom Condo Close to the Ocean

Key West condo
2 BR / 2 BA / Sleeps 6 | Quick view
Excellent14 Reviews

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Reviews

(14)

This quiet four-story condominium building is located just a short walk across the road to the Ocean with a recreational side walk miles long for running, walking, rollerblading and biking to Smaters Beach which is Key West's largest beach. This 2 bedroom, 2 bathroom unit offers all the convenience and comfort of your…
  • Hot Tub/Jacuzzi
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Outdoor Dining Area
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

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Reviews

(14)

Outstanding!

Left on Feb 18, 2013 for a stay in January 2013

This was perfect for us! It is fully stocked with everything you need. The pool, hot tub and grill area were great after a long day of sightseeing. We were well taken care by both Margaret and Pauly. Pauly referred us to good restaurants and cab service. Be sure to visit the Hogfish Bar & Grill while you're there! Thanks so much for making our vacation an enjoyable experience!

$219

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Coconut Mallory Resort 2 Bedroom Condo

Key West condo
2 BR / 2 BA / Sleeps 6 | Quick view
Terrible1 Reviews

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Reviews

(1)

This popular island destination is the site of the only living coral reef in the coastal regions of the US. In addition to the marine life and water activities other features of Key West include natural preserves and unique land animals. Coconut Mallory Resort and Marina is located in Key West, the southernmost …
  • Waterfront
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible - ask

Details

Reviews

(1)

Don't stay her

Left on Apr 03, 2014 for a stay in April 2014

We booked this through Expedia (sorry trip Advisor). Check in began at 4 according to our printed information from Expedia. We arrived at 6:30--the office was closed--- it had closed at 5. Check in is 4-5 PM???? An envelope was taped to the office door with our name on it and directions to our room, OK--we felt better.

I have traveled all over the world and have NEVER seen such a dark and …

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$289

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Eyebrow House - Historic Home in Heart of Old Town

Key West B&B
1 BR / 1 BA / Sleeps 4 | Quick view

Details

Eyebrow House is a very spacious one-bedroom suite with a large front porch and palm tree-filled private fenced-in yard overlooking a quiet side street. Our guests enjoy the best of both worlds as the restaurants, world-class galleries, and vibrant nightlife of Duval St. are just a half block away. You feel like a …
  • Hot Tub/Jacuzzi
  • Wireless Internet
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly - ask
1 / 6

$215

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Coconut Beach

Key West condo
1 BR / 2 BA / Sleeps 4 | Quick view

Details

This Key West condo is legally listed as a one-bedroom. However it could easily accommodate two couples, or a family of 4, with privacy. The first floor includes a full kitchen, full bath, dining area, TV area with a sofa, and a Murphy Bed. The second floor (a lock-out unit) includes a "closet kitchen", a king bed…
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Outdoor Dining Area
  • A/C or climate control
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly - ask
1 / 6

$215

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The Banyan Resort at Key West

Key West condo
2 BR / 1 BA / Sleeps 6 | Quick view

Details

Experience a world full of lush and fragrant gardens on a Caribbean Estate tucked away in the heart of Old Town, Key West. Stay in a 2 bedroom unit in a restored historic wrecker's home and wander through the extensive gardens as time transcends you to an era long ago. You can relax and indulge yourself at this …
  • Hot Tub/Jacuzzi
  • Internet Access
  • Outdoor Dining Area
  • A/C or climate control
  • Central heating
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly - ask
1 / 19

$255

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Key West Condo close to the Ocean

Key West apartment
2 BR / 2 BA / Sleeps 6 | Quick view

Details

This 2 bedroom, 2 bathroom unit offers all the convenience and comfort of your own home. It is spacious and fully equipped. Located just minutes from Smathers Beach, two miles from Higgs Beach. This condo is a fourth floor unit (there are two elevators in the building). It has a private balcony with an unobstructed …
  • Hot Tub/Jacuzzi
  • Wireless Internet
  • Washing Machine
  • Outdoor Dining Area
  • A/C or climate control
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly - elevator access
  • Wheelchair accessible - ask

$183

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Key West 2bd/2ba Condo - Monthly

Key West condo
2 BR / 2 BA / Sleeps 4 | Quick view
Excellent1 Reviews

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Reviews

(1)

***Due to licensing restrictions, this Key West Condo rental requires minimum stay of 30 nights*** MONTHLY RENTAL ONLY - NO PETS ALLOWED - NO SMOKING - NO EXCEPTIONS Seaside Breeze is a true Key West island paradise. It is a wonderful two bedroom two bath, newly renovated condo decorated in light and bright colors. …
  • Shared outdoor pool (unheated)
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Suitable for children
  • Suitable for the elderly - elevator access

Details

Reviews

(1)

Great location for hitting all the best of Key West

Left on Mar 17, 2015 for a stay in January 2015

Stayed here for 2 months while I was having my house remodeled and I was very pleased with the facilities and the unit.

The condo has been nicely redone and very well stocked with any items you might need during your stay. The Complex is well maintained and managed with plenty of parking available. A great Pool and whirlpool are available for your visit, and it was never super crowded during …

$1,200

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Suite Dreams in Key West

Key West house
7 BR / 6 BA / Sleeps 18 | Quick view
Excellent1 Reviews

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Reviews

(1)

Our unique property consists of 3 suites (a total of 7 bedrooms and 6 baths) with 2 sparkling lagoon style dipping pools in one compound in the luxurious Casa Marina area of Old Town Key West. We can accommodate groups up to 18 guests. The breakdown of the 3 suites which are being rented together are as follows: …
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(1)

Perfect stay

Left on Feb 16, 2014 for a stay in January 2014

So our stay was Friday - Tuesday in January … We rented the Hemingway suite then added additional rooms … Love Love Love this place !! can not say enough about the owners / and their property manager Vicki …. Highly recommend this place , it has everything you need .. Full property, private pool , Patio, Bbq, fully stocked kitchen , an on "your honor" store , washer dryer … going to …

$239

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Luxury 2Bed/Bath condo on the beach. (Sleeps 6)

Key West condo
2 BR / 2 BA / Sleeps 6 | Quick view
Excellent7 Reviews

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Reviews

(7)

Beautifully remodeled, 1374 sq. ft., 2 bedrooms (both are King Beds) 2 Bath condo located on the beach in a resort complex -(SLEEPS 6). Gorgeously landscaped & located RIGHT NEXT TO SMATHERS BEACH, the largest beach in Key West! AMENTIES INCLUDE: Private 40' Balcony, Master suite, Resort includes a Private …
  • Waterfront
  • Hot Tub/Jacuzzi
  • Sauna
  • Internet Access
  • Housekeeping Optional
  • Suitable for children
  • Suitable for the elderly - elevator access
  • Wheelchair accessible

Details

Reviews

(7)

Iowa Couple - Great Key West vacation

Left on Jan 19, 2012 for a stay in September 2011

This was our second trip to Key West and it was also a repeat stay in the
same place. The place was clean and nicely maintained as in our first
visit. The location on the beach is nice and we sure liked the convenience of being able to walk to Smather's Beach. We went with another couple and we all agreed the roominess of the place and also the heated pool on the beach, were both big factors…

$558

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Ocean Retreat

Key West condo
3 BR / 3 BA / Sleeps 5 | Quick view
Excellent1 Reviews

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Reviews

(1)

Private home of three bedrooms and 2 1/2 Baths within a gated community. High definition plasma TV found in every bedroom in addition to the living room and high speed internet available throughout. There is access to a large private association pool. This beautiful home is close to ocean and the beach. Only three …
  • Shared outdoor pool (unheated)
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Smoking allowed
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

Ocean Retreat- luxe comfort without pretense!

Left on Feb 28, 2014 for a stay in February 2014

This three bedroom condo (two upstairs bedrooms with king and twin beds and ensuite baths and a downstairs bedroom with full-sized bed and right-next-door half-bath) exceeded all our expectations. The new pictures are accurate representations of the condition and quality of the property. Tasteful and yet relaxed, this is, without a doubt, our favorite condo in our eight years of vacationing in …

$450

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4 Bedroom Home with private pool just off Duval St

Key West house
4 BR / 3 BA / Sleeps 7 | Quick view
Excellent4 Reviews

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Reviews

(4)

Chick-A-Pea’s Cottage: Located in the gallery district of Key West. The house is steps off of Duval St. near Hemmingway’s house, the Southernmost Point, the Butterfly Museum and great shops, restaurants and bars . The location is quiet & private… yet in the heart of key west The house is a traditional Key …
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(4)

Key West Charm

Left on Jun 30, 2013 for a stay in June 2013

Perfect home for my family of 5 adults. Very clean, well maintained property. Lovely pool and cabana which functions as an outside room. Location was great - not too close to the noise of Duval Street but close enough to walk to all the action. Good restaurants, Butterfly Museum, and Hemingway House nearby.

$743

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Ocean Paradise

Key West house
3 BR / 4 BA / Sleeps 8 | Quick view
Excellent1 Reviews

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Reviews

(1)

Three bedroom, four bathroom private home with heated pool stocked with massage water jets and special colored lighting. Breathtaking sunsets can be seen from third floor deck overlooking the Ocean. High definition plasma TV and surround stereo throughout the home. High Speed internet and faxing available as well. …
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

Perfect for a Memorable Key West Experience!

Left on Jun 02, 2015 for a stay in May 2015

My family and I absolutely loved staying in this beautiful Key West home. Located in Truman Annex (a quiet, private community in Old Town Key West), the location is perfect for whatever you wish to do during your Key West experience. Ocean Paradise has gorgeous views from the 3rd level balcony, a wonderful screened-in porch on the main level (perfect for al fresco dining), and an incredible pool …

$400

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Quilted Giraffe

Key West house
2 BR / 2 BA / Sleeps 4 | Quick view
Excellent2 Reviews

Details

Reviews

(2)

This home has a unique pricing structure. While it can rent for less than 30 days, the owner prefers Monthly rentals. Because of this, this home offers substantial (25% off) Monthly Rental discounts. Your space. Your vacation lifestyle. The Quilted Giraffe provides both. This two-bedroom, two full bath home welcomes …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for the elderly - ask

Details

Reviews

(2)

Relaxing respite

Left on Mar 05, 2010 for a stay in February 2010

The heated pool and lush backyard foliage were the draw to this well appointed home. Parking was a nightmare, the neighbor to the right facing the house was most unpleasant. A parking spot in the front yard would be recommended. The location was excellent for walking anywhere. The service was good once we met Bill. Prior to him, Corey and Libby both seemed disorganized and inattentive to our …

$425

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Valhalla

Key West house
2 BR / 2 BA / Sleeps 4 | Quick view
Excellent49 Reviews

Details

Reviews

(49)

This two-bedroom, two-bath classic contemporary is the perfect headquarters for your dream vacation. The entire inside is painted cloud white. This choice creates not only a crisp, clean elegance but also serves as the perfect backdrop for an amazing art collection. It's fitting that this special residence isn't …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for the elderly - ask

Details

Reviews

(49)

Wonderful Home

Left on Oct 17, 2008 for a stay in October 2008

We participated in a fund raiser for epilepsy in Houston and won the week at the house in an auction. We had never been to Key West and could not have been happier with the house and the island. It was beautiful, well furnished and very comfortable. It was also very close to both the beach and the clubs. We had a great week and will come back and rent from Historic Hideaways again.

$300

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Oceanside Key West's Best Luxury Penthouse Condo

Key West condo
3 BR / 2 BA / Sleeps 8 | Quick view
Excellent1 Reviews

Details

Reviews

(1)

WOW Oceanside Voted #1 Key West's Best Luxury Penthouse Marina/Condo/Pool Direct Oceanfront 1490 Sq Ft Condo, 3 Bedrooms, 2 Baths, (Sleeps 6) Oceanside Marina is one of the newest and one of the most prestigious communities offering breath taking water views and large, open units. The amenities are rounded out with …
  • Waterfront
  • Ocean or water views
  • Wireless Internet
  • Housekeeping Optional
  • Washing Machine
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly - elevator access
  • Wheelchair accessible

Details

Reviews

(1)

Awesome View. Great Place.

Left on May 01, 2015 for a stay in April 2015

My brother, mother and I and our spouses met up in Key West for a great vacation. This condo had plenty of space inside and out for 6 adults and was very comfortable. The deck offered a wonderful view for morning coffee, nap, conversation, and/or book read each and every day. The pool space was also great. This condo is technically on Stock Island which is on the opposite end from THE Duval …

$359

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Key West Harbour Oceanfront Suites

Key West condo
2 BR / 3 BA / Sleeps 5 | Quick view
Excellent35 Reviews

Details

Reviews

(35)

Fully Appointed Suite- Condominium Unit- 2 Bedrooms, 2.5 Baths (Sleeps 4-5) Our beautifully landscaped property and contemporary housing will provide you with a serene tropical setting ideal for a relaxing vacation getaway. Located off the azure waters of the Atlantic Ocean, minutes away from downtown Key West, …
  • Waterfront
  • Ocean or water views
  • Sauna
  • Internet Access
  • Housekeeping Optional
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

Details

Reviews

(35)

Out of Sight Excellence!

Left on Nov 20, 2013 for a stay in October 2013

From the very beginning of entering the property we knew that it was going to be special.
From Karen V. to Chef Clive who is one great Chef we cannot say enough about their care and handling of our three days. The facility is quiet and very clean we had a two bedroom suite. Waterfront with entrance to there pristine harbor wow what not to like especially there olympic size pool.

$220

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Oceanfront 2 Bedroom 2 Bath Condo Key West Florida

Key West condo
2 BR / 2 BA / Sleeps 6 | Quick view
Excellent2 Reviews

Details

Reviews

(2)

The "SeaJay" at La Brisa is located in a gated community overlooking the Atlantic Ocean just steps away from Smathers Beach with it's pristine sand and palm trees. Directly across the street is Key West's longest sidewalk along the beautiful ocean for bike riding, jogging or walking. Smathers Beach offers diving, …
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Sauna
  • Internet Access
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

Details

Reviews

(2)

Ocean Front Condo on Smathers Beach Gets an a+ for Value, Comfor

Left on Apr 07, 2014 for a stay in March 2014

Waking up after staying our first night at the condo located at La Brisa #105 East, I barely lifted my head up off the pillow and I could see the ocean! Wow, that was a nice wake-up!
The condo is very roomy, clean and tastefully decorated without any clutter. A great balcony with fantastic views is was super relaxing too.
A fully functioning kitchen was at the ready but other than making coffee…

1 / 10

$286

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A Dream come True

Key West house
3 BR / 3 BA / Sleeps 6 | Quick view

Details

******** Key West laws state that this property can only be rented out monthly******* This lovely home is in the Casa Marina District of Key West. It has a front porch, front balcony that the 2 smaller bedrooms have access to, a large patio by the heated private pool in the back yard, and a balcony off the master …
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Pet friendly - ask
  • Suitable for children
1 / 8

$271

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Calico Cove

Key West condo
2 BR / 1 BA / Sleeps 4 | Quick view

Details

Two bedroom / 1 bath, second floor, corner unit with front and back porches located at the Shipyard in Old Town, two blocks from Duval Street and everything that's happening in Key West but quiet enough to relax when you need to. Master bedroom has a queen size bed and guest bedroom two twin size beds to accommodate …
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Central heating
  • Porch
  • Suitable for children - ask
  • Suitable for the elderly - ask

$500

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Pineapple Cottage Key West

Key West house
2 BR / 2 BA / Sleeps 4 | Quick view
Excellent14 Reviews

Details

Reviews

(14)

The Pineapple Cottage is tucked away and totally private, yet it is only a half a block from Duval Street. This two story "cottage" offers a first floor bedroom that opens through french doors to the private pool and gardens. A second floor suite includes a bedroom and bath plus a seperate living room. Each floor has …
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area

    Details

    Reviews

    (14)

    We loved it, you can't beat the location

    Left on Oct 15, 2010 for a stay in October 2010

    We booked through preferred properties and they were very helpful. The cottage is right next to their office so check in was easy. I have to be honest and say I was very apprehensive when we entered the cottage through the car park but I needn't have been, it's like entering your own private oasis! You would never know it is there, but its so close to everything which is perfect. The decking area…

    $197

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    Key West Fully Equiped 2 br, 2ba

    Key West condo
    2 BR / 2 BA / Sleeps 6 | Quick view
    Excellent2 Reviews

    Details

    Reviews

    (2)

    The resort all the convenience and comfort of your own home with these spacious fully equipped 2 bedroom condos located just minutes from Smathers Beach and 2 miles from Key West Airport. This location is also two miles from popular Higgs Beach and between 4 miles from the Key West Lighthouse Museum, Discovery …
    • Hot Tub/Jacuzzi
    • Internet Access
    • Housekeeping Optional
    • A/C or climate control
    • Central heating
    • Pet friendly
    • Smoking allowed - ask
    • Suitable for children
    • Suitable for the elderly - elevator access
    • Wheelchair accessible

    Details

    Reviews

    (2)

    Fantastic!!!

    Left on Jan 23, 2014 for a stay in January 2014

    The condo was fantastic. I was clean convenient and would recommend to anyone. This was exactly as described.

    $185

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    Penthouse Condo in Key West Florida

    Key West condo
    2 BR / 2 BA / Sleeps 6 | Quick view
    Very Good2 Reviews

    Details

    Reviews

    (2)

    Penthouse unit has designer furniture in this two bedroom (master has king size bed and guest bedroom has a queen) with a comfortable queen sleeper sofa in the living room. Two full bathrooms, full kitchen, dishwasher, microwave, cook top and electric oven, and outside balcony overlooking the beautiful pool and …
    • Shared outdoor pool (unheated)
    • Internet Access
    • A/C or climate control
    • Porch
    • Parking
    • Suitable for children
    • Suitable for the elderly
    • Wheelchair accessible

    Details

    Reviews

    (2)

    Noisy inconsiderate poorly behave guests

    Left on Sep 03, 2013 for a stay in September 2013

    Our first night I was kept up until 4 AM by noisy you people and I love to hang and have fun but come on they were really poorly behaved. The following night Saturday of Labor Day they were all over the pool and parking and once again kept me up until 4:29 PM. By Sunday I was a wreck, very tired and could not stop yawning with a severe headache and not for having a hang over but from lack of …

    $300

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    Key West Beachfront Luxury 2/2 Condo A212

    Key West condo
    2 BR / 2 BA / Sleeps 6 | Quick view
    Excellent30 Reviews

    Details

    Reviews

    (30)

    This Luxury unit is 1375 sq ft of breath taking beachfront living space in this tropical complex. Great views from the 40 foot deck which encompasses the whole unit. Every room has a spectacular view of the tropical Nature Preserve and the Atlantic Ocean. The complex is oceanfront with an Olympic heated pool and …
    • Waterfront
    • Ocean or water views
    • Hot Tub/Jacuzzi
    • Sauna
    • Internet Access
    • Suitable for children
    • Suitable for the elderly - elevator access
    • Wheelchair accessible

    Details

    Reviews

    (30)

    comfortable condo in great complex near the beach

    Left on Aug 09, 2012 for a stay in April 2012

    Loved it!! Five of us recently stayed here for a much needed relaxing getaway. This condo was perfect for us. It was spacious and very clean. The kitchen had everything we needed. There are even BBQ grills in the common area if you want to have a cook-out. Having a washer and dryer right in the condo was super convenient. We loved enjoying our morning coffee and afternoon cocktails on the covered…

    1 / 24

    $600

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    Garden Home Paradise in Midtown Key West

    Key West house
    2 BR / 2 BA / Sleeps 6 | Quick view

    Details

    2 bedrooms, 1 Bath, 1 Outdoor Shower and Pavillion, Tropical Garden (sleeps 4-6). Open the gate and stroll through the lush gardens of this beautiful two bedroom, one bath home, built in 1953 and entirely renovated. In addition to the updated kitchen and bath, there's a screen porch, a covered outdoor pavillion with …
    • Internet Access
    • Housekeeping Optional
    • Washing Machine
    • Clothes Dryer
    • Outdoor Dining Area
    • Pet friendly
    • Suitable for children
    • Suitable for the elderly - ask
    1 / 20

    $183

    Book

    A Low Key Paradise- Monthly rental only

    Key West house
    2 BR / 2 BA / Sleeps 6 | Quick view

    Details

    Located on a quiet residential street in the beautiful Key West neighborhood of Casa Marina, A Low Key Paradise has a beautiful open layout, with views of the large private patio and pool visible as soon as you enter. Guests can walk to nearby Higgs beach, and Higgs beach dog park— perfect for your family member …
    • Internet Access
    • Housekeeping Optional
    • Washing Machine
    • Clothes Dryer
    • Outdoor Dining Area
    • Pet friendly
    • Suitable for children
    • Suitable for the elderly
    • Wheelchair accessible - ask

    $205

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    Tropical Escape

    Key West condo
    2 BR / 2 BA / Sleeps 6 | Quick view
    Excellent45 Reviews

    Details

    Reviews

    (45)

    This luxurious condo/hotel features a wonderful tropical interior design. It has 2 spacious bedrooms (one room with a king-size bed and a full bath and one queen-size bed with a full bath. The unit has a fully equipped kitchen that looks onto the living room with a queen-size sofa sleeper. The patio overlooks the …
    • Hot Tub/Jacuzzi
    • Internet Access
    • Housekeeping Optional
    • Washing Machine
    • Clothes Dryer
    • Pet friendly
    • Suitable for children
    • Suitable for the elderly - elevator access

    Details

    Reviews

    (45)

    Relaxing

    Left on Nov 26, 2010 for a stay in July 2010

    Check-in was quick & easy. Condo was clean, nicely decorated and very accomodating to our party of four. The location in the building made it easily accessable to the pool & barbecue area and covered parking under the building was a nice plus. Condo location was a bit far from Duval Street but it was nice to retreat to the peace and tranquilty after visiting busy downtown. There were also …

    $349

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    Key West 'Yacht And Breakfast!'

    Key West yacht
    3 BR / 2 BA / Sleeps 8 | Quick view
    Excellent5 Reviews

    Details

    Reviews

    (5)

    Upscale 'Yacht and Breakfast'! 3 bedroom, (4th convertible bed), 2bath luxury yacht. IF TRAVELING WITHIN 3 WEEKS please contact us for reduced rates! Fully equipped from bow to stern -- Galley (kitchen to the non-boat speakers) has all cooking, baking and grilling items; 3/4 fridge/freezer, Keurig coffee, 3 burner …
    • Waterfront
    • Ocean or water views
    • Shared outdoor pool (unheated)
    • Internet Access
    • Washing Machine
    • Suitable for children
    • Suitable for the elderly
    • Wheelchair accessible - ask

    Details

    Reviews

    (5)

    Key West - Yacht Style

    Left on Jan 12, 2015 for a stay in December 2014

    It never crossed my mind to look into staying on a Yacht in Key West. Now, everywhere we travel it is our first option. The boat accommodations were perfect for us. We could fish right off the docks, paddle the kayaks around the marina, and bike around town. Front Street and Duval were only steps from the marina. Staying on this boat made our trip better than we could have ever imagined. We were …

    $300

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    Pelican Landing Abaco Retreat

    Key West condo
    2 BR / 2 BA / Sleeps 8 | Quick view
    Excellent12 Reviews

    Details

    Reviews

    (12)

    Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is 25 years old. Everyone in your party must be 25 years old to check in unless accompanied by a parent. Our beautiful waterfront condos have a range of …
    • Shared outdoor pool (unheated)
    • Internet Access
    • A/C or climate control
    • Balcony or terrace
    • Grill
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (12)

    Flawless new year stay

    Left on Jan 20, 2012 for a stay in January 2012

    Outstanding time wonderful facilities, will bring boat next time

    $300

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    A Touch of Bermuda in Key West

    Key West house
    2 BR / 2 BA / Sleeps 6 | Quick view
    Excellent9 Reviews

    Details

    Reviews

    (9)

    Envision yourself unwinding and getting into the casual clothes we wear in Key West while you look around and know you are in Paradise as our island is called. Then ask anyone and they will tell you the best place to stay in Key West is the Truman Annex. My Bermuda-style cottage is on the picturesque main entrance …
    • Internet Access
    • Housekeeping Optional
    • Washing Machine
    • Clothes Dryer
    • Outdoor Dining Area
    • Pet friendly - ask
    • Suitable for children
    • Suitable for the elderly
    • Wheelchair accessible - ask

    Details

    Reviews

    (9)

    warm, convenient and comfortable

    Left on Jun 24, 2010 for a stay in May 2010

    great location, lovely unit, comfortable, clean, nice pool, and a terrific owner.

    $200

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    Key West Garden House

    Key West house
    1 BR / 1 BA / Sleeps 2 | Quick view
    Excellent16 Reviews

    Details

    Reviews

    (16)

    Experiance the laid back life of the tropics in this light and airy 1 bedroom, 1 bath private home. Located on a quiet lane in the heart of Old Town, The Key West Garden House features a large covered back porch, outdoor living and dining area, gas barbeque and heated pool in a lush tropical setting. The yard is …
    • Internet Access
    • Washing Machine
    • Outdoor Dining Area
    • Grill
    • Satellite or cable TV
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask

    Details

    Reviews

    (16)

    Great Experience!

    Left on Jul 23, 2013 for a stay in May 2013

    We stayed at the Garden House with our maltese in May. Susan was terrific and her place felt like a home away from home in the Keys. It is such an adorable historic house, we just loved it.
    I hope to go back soon and stay at the Garden House again.
    Maureen B.

    1 / 22

    $325

    Book

    Key West Florida Beachfront Condo

    Key West apartment
    2 BR / 2 BA / Sleeps 6 | Quick view

    Details

    WELCOME to our beachside condo in Key West. Our terrace directly overlooks Smather's Beach and is the focal point of our home; watch the sunrise with coffee; watch the kids on the beach and the parasailors fly by; have a private sunset dinner; enjoy a late night drink and watch the cruise ships leave port. Our …
    • Ocean or water views
    • Hot Tub/Jacuzzi
    • Sauna
    • Wireless Internet
    • Washing Machine
    • Pet friendly - ask
    • Suitable for children
    • Suitable for the elderly - elevator access
    • Wheelchair accessible
    1 / 10

    $83

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    Minimum 90 day rental - 1 bedroom 1 Bathroom Condo at Las Salinas

    Key West condo
    2 BR / 2 BA / Sleeps 2 | Quick view

    Details

    Minimum 90 day stay requirement- Las Salinas is well maintained and has a beautiful community pool. Offers covered parking. There is a shared swimming pool.Located in New Town featuring 1 bedroom with a queen sized bed and one bathroom. The unit has a private balcony and offers covered parking. There is a shared …
    • Shared outdoor pool (unheated)
    • Internet Access
    • A/C or climate control
    • Balcony or terrace
    • Linens Provided
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    $357

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    SeaShadows of Key West

    Key West house
    2 BR / 2 BA / Sleeps 4 | Quick view
    Excellent13 Reviews

    Details

    Reviews

    (13)

    SeaShadows is a townhouse located just 2 blocks from Duval Street and a few minutes walk from Mallory Square. Down the street is Ft. Zachary Taylor Park where you can spend the day fishing, swimming, barbecuing, walking, and anything else that you can think of doing in the sun. It sleeps 4 adults or two adult …
    • Shared outdoor pool (unheated)
    • Internet Access
    • Housekeeping Optional
    • Washing Machine
    • Clothes Dryer
    • Suitable for the elderly - ask

    Details

    Reviews

    (13)

    Absolutely fantastic

    Left on May 31, 2011 for a stay in May 2011

    Had a fantastic week in fey west,the townhouse was beautiful,the location was perfect,townhouse had everything you could possibly need also a great pool area..Everything is in walking distance,we will absolutely go back next year and many years after that thank you so much Sonia

    $315

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    Tropical Paradise on the Atlantic Ocean

    Key West condo
    2 BR / 2 BA / Sleeps 6 | Quick view
    Excellent10 Reviews

    Details

    Reviews

    (10)

    Make our lovely home your dream vacation destination in fun-filled tropical Key West, Florida. "1800 Atlantic" is Key West's premiere luxury condo complex on a private Atlantic Ocean beach. Our beautifully furnished large 2 bedroom and 2 bath condo overlooks a serene tropical garden. Both bathrooms and kitchen were…
    • Waterfront
    • Hot Tub/Jacuzzi
    • Sauna
    • Internet Access
    • Washing Machine
    • Suitable for children - ask
    • Suitable for the elderly

    Details

    Reviews

    (10)

    Great Beach Location and Value

    Left on May 07, 2010 for a stay in April 2010

    Patrick was very professional and courteous. The two bedroom condo was very large and accommodated the six people in my family very well. The Courtyard, heated pool, hot tub and grille were very nice to have access to. We also played a few sets of tennis which was very fun. The location was very close to Smathers Beach and a nice bike ride to Duval. We really enjoyed all the amenities the …

    $1,074

    Inquire

    Top Of Duval- 6 Bedroom Penthouse

    Key West house
    6 BR / 6 BA / Sleeps 16 | Quick view
    Excellent1 Reviews

    Details

    Reviews

    (1)

    Ready to escape to Key West? Make the most of your visit and stay at Top of Duval Vacation Rentals, located in the heart of Key West's Old Town. It's like having your own private hotel. If you are vacationing with family and friends, Top of Duval offers a truly unique layout with six individual suites. Perfectly …
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • Outdoor Dining Area
    • A/C or climate control
    • Suitable for children
    • Suitable for the elderly

    Details

    Reviews

    (1)

    A++ LOCATION AND AMENITIES!!

    Left on Dec 22, 2014 for a stay in December 2014

    This place was fantastic. With friends or family every room has its own bathroom and kitchen so you Can spread out. The front of building is right in the action on duval and the back is a quiet private pool great for relaxing. I would definitely stay here again this place is awesome especially for groups!

    1 / 22

    (1)

    Poor

    $350

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    KEY WEST LIVIN' BEAUTIFUL 50' Yacht 3 Bed , 2 bath, WIFI, Flatscreen,Sleeps 6

    Key West houseboat
    3 BR / 2 BA / Sleeps 6 | Quick view

    Details

    Reviews

    (1)

    BETTER THEN ANY HOTEL IN KEY WEST HANDS DOWN :) As the name suggests Key West Livin' this is the only way To truly experience what Key West is all about. Stay aboard this 50 foot Ocean Super Sport Yacht instead of a hotel room in Beautiful Harbor Yacht Club located on the ocean with Beach , Heated Infinity -Edge …
    • Waterfront
    • Ocean or water views
    • Sauna
    • Internet Access
    • A/C or climate control
    • Pet friendly
    • Suitable for children
    • Suitable for the elderly
    • Wheelchair accessible - ask

    Details

    Reviews

    (1)

    Not worth your money: Falling apart and dirty.

    Left on May 18, 2015 for a stay in April 2015

    Would be lovely with lots of maintenance and repairs. Water leak in the cabin, smells humidity, surage, fridges are sticky from dirt and the fridge door won’t even close. Towels and beddings are dirty as well the seats, showers and the rest… No keys to lock it. We wanted to try "boat living" before buying a boat... The Marina is nice and quiet, 5 miles from Duval Street.

    $378

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    "DU PONT HOUSE" Luxury Rental - Private Pool - 1/2 Block To Duval St.

    Key West house
    2 BR / 2 BA / Sleeps 6 | Quick view
    Excellent11 Reviews

    Details

    Reviews

    (11)

    Built in the 1990's, The Du Pont House is a two story hideaway on a quiet lane. Completely gated and fenced, your private pool is surrounded by tropical plants ablaze with color. French doors in the living room and bedroom open to your private courtyard and outdoor shower. The second bedroom and bath are …
    • Internet Access
    • A/C or climate control
    • Deck
    • Grill
    • Linens Provided
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (11)

    Another wonderful stay

    Left on Sep 10, 2010 for a stay in August 2010

    We love the Dupont House! Pictures don't quite do it justice because it has two-story ceilings because of the second bedroom. It is much more open and roomy than it appears. This is our second stay there and both times it has been perfect. It is current and appropriately (not to mention cutely) decorated... Seriously cute - we have a bunch of pictures of the house and its decorations! The house …

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