Key West

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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

Details

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 …

$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.

$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

Details

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!

$186

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Sunshine Luxury Suite - 2 Free Bicycles & Garage

Key West condo
2 BR / 2 BA / Sleeps 6 | Quick view
Excellent1 Reviews

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Reviews

(1)

My Sunshine Luxury Suite is an upscale property located in Key West, an island paradise. Sunshine Suite provides the luxury and convenience of your own condo home just 90 miles from Havana. Surrounding the resort, you will enjoy lush tropical foliage and amenities such as our tennis court, gym facilities, and heated …
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(1)

Great Place!

Left on Oct 28, 2014 for a stay in October 2014

fabulous condo on a very secure property close to the beaches. Roosevelt Blvd is within walking distance and has a sidewalk large enough for walking and biking along the ocean. The unit is very clean, well stocked with linens, has a fully equipped kitchen and has everything you need and/or forgot. It also has a covered parking spot and bicycles! Perfect layout for two couples each bedroom has…

$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 …

Key West Condo close to the Ocean - Key West vacation rentals
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
1 / 18

$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

$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 …

$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 …

$350

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Premium 1800 Atlantic Key West - C232

Key West condo
2 BR / 2 BA / Sleeps 6 | Quick view
Excellent3 Reviews

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Reviews

(3)

Unit C232 is one of the premium rental Condo's in the 1800 Atlantic Complex. Beautifully decorated with higher end furnishings. Top of the line full size fully equipped eat in Kitchen. Dining room area and spacious living room. Both Bedrooms and the living room open onto the expansive private balcony that runs the …
  • Suitable for children - ask
  • Suitable for the elderly
  • Wheelchair accessible - ask

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Reviews

(3)

Another great stay!

Left on Jul 15, 2010 for a stay in June 2010

Every facet of our stay was perfect. We have stayed in many other places in Key West, and this is by far our favorite! We have stayed in this particular unit several times, and will continue to do so. The location is great: right on the ocean, on the quiet side, and stores, etc. are a short distance away, without having to brave the traffic of the whole"Duval area". The whole experience was easy…

$205

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Nassau Suite Old Town Key West

Key West house
1 BR / 1 BA / Sleeps 4 | Quick view
Excellent12 Reviews

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Reviews

(12)

• Wireless Internet • Full Kitchen Nassau Suite is a bi-level suite with a very spacious bedroom upstairs a king bed, TV, writing desk w/outlet for computer and chair, in-room safe, iron & ironing board complete with Bahama ceiling fan, A/C and colorful Caribbean artwork. The upstairs tiled bath with hair…
  • Smoking allowed - ask
  • Suitable for children - ask

Details

Reviews

(12)

A nice and quiet place to stay

Left on Jan 29, 2011 for a stay in January 2011

Close to all activities in Duval street (walking distance).
Possibility to stay outside on porch or on central area.
Lots of privacy. Food store next door.

One negative point maybe: no parking available

1 / 54

(1)

Poor

$117

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Artist cottage with hot tub

Key West cottage
1 BR / 1 BA / Sleeps 4 | Quick view

Details

Reviews

(1)

The artist cottage is mainly used as a residence for visiting artist that are in town doing shows at my gallery. The cottage is very quiet and secluded with lots of privacy,situated amongst 100 year old trees and lush tropical foliage. The cottage was built in 1913 and is a true piece of old key west. The property is…
  • Hot Tub/Jacuzzi
  • Internet Access
  • Housekeeping Optional
  • Outdoor Dining Area
  • A/C or climate control
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

Wonderful little cottage, not so wonderful owner

Left on Apr 07, 2014 for a stay in June 2013

First, let me say that I intended not to review this property simply because I didn't want to leave a negative review but today I got a letter in the mail that made me change my mind.The cottage was great, clean,neat,location great, and a great place for our little dogs, who were welcome. First there was no washing machine which didn't seem a problem because David assured us that our laundry …

$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 …

$359

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Key West Harbour Oceanfront Suites

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

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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…

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$215

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Casa Alegre

Key West villa
1 BR / 1 BA / Sleeps 2 | Quick view

Details

Nestled midway between the Atlantic Ocean and the Gulf of Mexico is Casa Alegre, an easy-living one-bedroom, one-bath duplex cottage featuring a bubbling hot tub on its own private deck. The White Street corridor is an Old Town neighborhood unto itself, yet the world-famous Duval Street in easy walking distance. In …
  • Hot Tub/Jacuzzi
  • Internet Access
  • Patio
  • Parking
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
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$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

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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…

    $353

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    Hemmingway's Retreat

    Key West house
    3 BR / 2 BA / Sleeps 8 | Quick view
    Excellent8 Reviews

    Details

    Reviews

    (8)

    Welcome To Paradise!!! Located in the heart of Key West this charming 3 bedroom, 2 bathroom house has been completly renovated and includes 50", 42", and 27" flat screen TVs, DVR, and wireless high speed internet. The interior has just been furnished with custom designer furniture by Domestic Home Furnishings. The …
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly

    Details

    Reviews

    (8)

    1211 Catherine St.

    Left on May 10, 2010 for a stay in April 2010

    My wife and I spent time in April at 1211 Catherine St., Key West, FL and had a marvelous time. The house is wonderful expecially the private pool. All that Key West has to offer is within easy walking or cycling distance of the house. The house is beautifully furnished and appointed so much so we spent many days just staying home and relaxing around the pool. One of the bicycles provided had to…

    $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 …

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    $258

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    Key West Bluewater Retreat

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

    Details

    Bluewater is a classic porch-on-porch Key West home with all the amenities to make your vacation ideal. Located in the prestigious Sanctuary of the Key West Golf Club, the house has two bedrooms each with its own private bath. The house sleeps 4 adults and two children or smaller adults. It offers a private patio, …
    • Pet friendly - ask
    • Suitable for children

    $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 …

    $117

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    The Tree House Old Town Built 1883 MONTHLY Rental

    Key West house
    2 BR / 1 BA / Sleeps 7 | Quick view
    Excellent3 Reviews

    Details

    Reviews

    (3)

    Our lovely home is rented for a 28 day minimum.Enjoy the lovely Key West ocean breeze from your private Tree House. Two Blocks to Blue Heaven, 4 blocks to the beach, 3 blocks to Duval, 3 blocks to the biggest pool on the Island, you will not find a better or quieter location to enjoy all that Key West has to offer. …
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • Outdoor Dining Area
    • A/C or climate control
    • Pet friendly
    • Smoking allowed - ask
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (3)

    Wonderful

    Left on Jul 18, 2014 for a stay in December 2013

    Close to everything! Furnishings just the best. We stayed upstairs in the 2 bedroom 1 large bath. Great wrap around porch up stairs and down. Our key Westies were welcomed which was a plus for us! Overall Stephanie has done a great job and her sister was really helpful. Planning on returning!!!!

    $159

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    It's a Sweet Deal in Historic Old Town

    Key West condo
    1 BR / 1 BA / Sleeps 4 | Quick view
    Excellent21 Reviews

    Details

    Reviews

    (21)

    CALL AND ASK ABOUT OUR WEEKLY SPECIAL WITH 1 NIGHT FREE! You will love staying in this great Key West historic old town location where 90% of the residents are local. They each have an interesting Key West tale to tell and are a very warm,friendly and diverse group. Here you will absorb the ambiance that made Key …
    • Wireless Internet
    • Porch
    • Linens Provided
    • Towels Provided
    • Freezer
    • Suitable for children - ask
    • Suitable for the elderly

    Details

    Reviews

    (21)

    Key West in the Spring Time!!

    Left on May 01, 2010 for a stay in April 2010

    What a great little place! We enjoyed our stay the most. This is very convenient to anywhere you would like to go in Key West. About 1 mile from anything and everything. We walked most everywhere but there is bike rentals at the end of the block. The place is VERY clean and perfect for a couple. (maybe three but 3's a crowd!) We love it here and hope to come back sooner rather than later…

    $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 …

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    $140

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    Conch Haven Built 1883 Beautiful ! MONTHLY Rental

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

    Details

    This 1200 sq ft luxury apartment in the the heart of Old Key West is located only 2 blocks off Duval St and is a short walk or bike to all the fun of Key West ! The property is completely private and safe, surrounded by a 6 foot gated fence and tropical landscaping. Due to local zoning laws we can only rent by the …
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • Outdoor Dining Area
    • A/C or climate control
    • Pet friendly
    • Smoking allowed - ask
    • Suitable for children - ask
    • Suitable for the elderly

    $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

    $1,150

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    Tropical ~ Tranquility ~ Weekly Rental

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

    Details

    Reviews

    (1)

    Few places exist where you can ride the fine line separating a secluded tranquil luxury villa, and the Heart of Old Town Key West. It may sound like a poetic abstraction, but for this masterful property with 5-Star amenities, the distinction is definitely real. Extraordinarily secluded and completely hidden from view …
    • Housekeeping Optional
    • A/C or climate control
    • Satellite or cable TV
    • Stereo or CD player
    • Telephone
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (1)

    Girl get-away

    Left on Apr 12, 2012 for a stay in February 2012

    Wonderful place. As nice as photos in ads. Pool has sun all day, am and pm! Plenty of bathroom space. Lovely kitchen. We managed a week without a car. Not too far to walk to all the fun night spots. Beach walk took 5 minutes!

    $175

    Book

    KeyWestStay.com

    Key West condo
    2 BR / 1 BA / Sleeps 4 | Quick view
    Very Good1 Reviews

    Details

    Reviews

    (1)

    For those of you who want to stay as close to Key West as possible without paying those outrageous Key West prices, stay with us between mile marker 10 and 11 in this waterfront condominium. This small, yet efficient penthouse condominium, 672 sq. ft., stands alone as a roof unit on building 3 of Bayside Condominiums …
    • Waterfront
    • Ocean or water views
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • Suitable for children

    Details

    Reviews

    (1)

    The outside appearance of the condo isn't attractive, but the inside was.

    Left on May 03, 2014 for a stay in May 2014

    The condo was exactly what I was looking for and it was represented accurately. It was about fifteen minutes from Duval street, had a water view, it was quiet and the interior was clean and in good shape. I had no problems

    $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
    • Suitable for children
    • Suitable for the elderly

    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.

    $325

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    Caribbean Cottage ~ Weekly Rental

    Key West house
    2 BR / 2 BA / Sleeps 5 | Quick view
    Very Good2 Reviews

    Details

    Reviews

    (2)

    Imagine the quintessential Caribbean island village, its cottages nestled hand-in-hand on charming historic pedestrian streets. As people stroll by, sun kissed from an afternoon of beaching and sight seeing, they'll say hi to one another even if they've never met. This is your neighborhood during your stay at …
    • Wireless Internet
    • A/C or climate control
    • Stereo or CD player
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (2)

    Private and Convienient

    Left on Dec 01, 2013 for a stay in November 2013

    We just stayed here Thanksgiving week and had a great time. It is right off Duval Street and you can walk any where easily. The hot tub is the back yard is very private. The only problem was the resident rooster who liked to wake up well before the crack of dawn.

    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

    $1,074

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    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 / 16

    $214

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    Key West Beach Front rental Your Ocean View Studio

    Key West condo
    1 BA / Sleeps 2 | Quick view

    Details

    See if this unit is for you! Want to have a piece of Paradise to call your own? Even tho it for a short stay?… read rates then call- NO QUOTES BY EMAIL thank you Questions by phone! Give a call Come have breakfast lunch or dinner in your hidden GEM of a suite overlooking the beach! We are So glad you found us! …
    • Waterfront
    • Ocean or water views
    • Housekeeping Optional
    • Outdoor Dining Area
    • A/C or climate control
    • Suitable for the elderly - ask
    1 / 25

    $208

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    TRUMAN @ DUVAL 'Old Town KW' Home Just A Hop-Skip-And-Jump To Duval St.

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

    Details

    Truman at Duval - if you're looking for South Beach slick-- not here! If you're looking for Key West charm and location, look no further. Small 2 bedroom, 1 bath, apartment that just screams fun and good times! Duval, with its world class reputation, beckons you to come play. Sight-seeing, people watching, it's all…
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    $1,500

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    Real World MTV House Key West

    Key West house
    10 BR / 6 BA / Sleeps 20 | Quick view
    Excellent39 Reviews

    Details

    Reviews

    (39)

    THIS ISN'T JUST A HOUSE, THIS IS YOUR OWN PRIVATE MINI RESORT IN KEY WEST, FLORIDA. THIS IS THE PROPERTY USED BY MTV TO FILM THE 2006 REAL WORLD KEY WEST. 500 FEET OF OCEANFRONT, 8 to 10 BEDROOMS are available (sleeps up to 20) , 5 1/2 baths, 11 plasma TVs, pool table (and Ping Pong), tennis court, optional Racket …
    • Waterfront
    • Ocean or water views
    • Hot Tub/Jacuzzi
    • Internet Access
    • Housekeeping Optional
    • Pet friendly - ask
    • Suitable for children - ask
    • Suitable for the elderly
    • Wheelchair accessible - ask

    Details

    Reviews

    (39)

    Just plain amazing!!!

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

    Totally exceeded our expectationsa. The house was clean, plenty of amenities, Andrew and adam were just amazing. We had a group of 16 adults and the house was perfect for that size of party. Nice quiet neighborhood and clean water. We saw , Tarpon and other fish swimming around the dock and had a matee say hi to us also. Will definently return and highly recomend.

    $185

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    Architects Cottage on Quiet Lane in Old Town

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

    Details

    Reviews

    (1)

    Note, this is a monthly rental. We do not rent our home out for less than 30 days. Historic 'conch' house has been completely redesigned and custom crafted by 2 architects as our home away from home. Featured on HGTV in 2007 (!), this intimate house boasts many fun and thoughtful features which will help make your…
    • Wireless Internet
    • Washing Machine
    • Clothes Dryer
    • Outdoor Dining Area
    • A/C or climate control
    • Pet friendly - ask
    • Suitable for children

    Details

    Reviews

    (1)

    Tranquility and great music at night

    Left on Dec 08, 2014 for a stay in November 2014

    This is a wonderful conch house in Old Town, Key West. The house is just around the middle of Old Town, so you can walk or bike to the harbor, the ocean, and the great music at night. There is a little park at the end of the lane, and if you travel with a dog as I do, the park is a great place to meet other people and dogs. There is a large, light-filled room overlooking the pool in the …

    $10,000

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    Ellen's Retreat, tropical living, MINIMUM 28 days

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

    Details

    Reviews

    (2)

    This beautiful home offers you contemporary luxury combined with exquisite historical charm of Old Town Key West. The open and spacious downstairs floorplan has an abundance of natural light and opens onto a fabulous pool area with an expansive deck. Entertaining your family and friends is effortless with the design …
    • Hot Tub/Jacuzzi
    • Internet Access
    • Housekeeping Optional
    • Washing Machine
    • Clothes Dryer
    • Pet friendly - ask
    • Suitable for children - ask
    • Suitable for the elderly - ask

    Details

    Reviews

    (2)

    A place in heaven!

    Left on Feb 19, 2013 for a stay in January 2013

    Ellen´s retreat was simply fantastic. The house was beautiful and luxurious. The grounds were spacious and it was like you had your very own private oasis. I need also to mention the fantastic and beautiful heated pool in which both children and adults spent most of their time.

    I will certainly come back again. I have never in my lift had such a great holiday stay.

    $175

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    Sunrise at Seaside Condo 2 Bedroom

    Key West condo
    2 BR / 2 BA / Sleeps 5 | Quick view
    Excellent8 Reviews

    Details

    Reviews

    (8)

    Tropical 2 bedroom, 2 bath Key West Condo. Large balcony overlooking pool. Full kitchen and living room with all the amenities of home. Large heated pool and Jacuzzi. Tennis court and gym. Washer and dryer in unit. Great condo complex on quiet side of island. Located 1 mile from Smathers Beach. Plenty of …
    • Hot Tub/Jacuzzi
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • Outdoor Dining Area
    • Suitable for children
    • Suitable for the elderly

    Details

    Reviews

    (8)

    OK

    Left on Feb 14, 2014 for a stay in February 2014

    when we arrived the condo smelled cigarette smoke, there was no notation if there is wi-fi and if there was no code was provided until we called the following day.

    i know this is Key West where smoking is allowed everywhere. when i looked at the ad smoking was not mentioned. i just assumed that the condo would be smelling great since the rent was top notched. it is about 4 miles to the heart of …

    $322

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    Olivia Cottage: A charming Old Town house near Key West's historic cemetery

    Key West house
    2 BR / 3 BA / Sleeps 4 | Quick view
    Excellent2 Reviews

    Details

    Reviews

    (2)

    30 DAY MINIMUM RENTAL OLIVIA COTTAGE Recently featured in Coastal Living's "Guestbook" column, this charming Old Town house has recently been completely and tastefully renovated by its owners. Located just across the street from Key West's historic city cemetery, truly a tourist attraction in our town, the Oliva …
    • Hot Tub/Jacuzzi
    • Internet Access
    • A/C or climate control
    • Deck
    • Parking
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (2)

    Stepping Into a Picture

    Left on Jul 21, 2011 for a stay in June 2011

    I stayed in Olivia Cottage five weeks and loved every minute. After looking at pictures on the internet, I felt like I was stepping into the pictures. It's exactly as shown. The patio/pool area is just the most relaxing place. Everything I needed was provided and the staff at KW Vacation Rentals were most friendly and helpful. I had one problem with the smoke detectors and it was repaired quickly…

    $360

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    Casa Alegria - a Bahamian style conch house

    Key West house
    3 BR / 4 BA / Sleeps 8 | Quick view
    Excellent3 Reviews

    Details

    Reviews

    (3)

    30 DAY MINIMUM RENTAL Welcome to Casa Alegria! An extended vacation at this Bahamian style conch house is sure to bring you happiness and joy! As you approach the front of the house you'll notice ample off-street parking on either side (a rarity in Old Town!) as well as an easy place to park bicycles. You can park…
    • Internet Access
    • A/C or climate control
    • Deck
    • Parking
    • Grill
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (3)

    paradise

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

    We were fortunate enough to stay in this immaculate and welcoming retreat. We loved swimming in the pool and riding the bikes around town. We could not have asked for a more perfect place to make our vacation more fabulous!!!! Love...love...love!

    $290

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    Beach Club #112 - Unique Oceanfront living

    Key West condo
    2 BR / 2 BA / Sleeps 5 | Quick view
    Excellent9 Reviews

    Details

    Reviews

    (9)

    Unique oceanfront living only 65 feet from the Atlantic! The Key West Beach Club is a quiet, peaceful residential building that sits directly on the water. The breathtaking view can be seen as soon as you enter the unit. This comfortable 2 bedroom unit features a huge oceanfront balcony accessed from both the …
    • Ocean or water views
    • Shared outdoor pool (unheated)
    • Internet Access
    • A/C or climate control
    • Balcony or terrace
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (9)

    Fabulous view

    Left on Jun 19, 2009 for a stay in May 2009

    This unit was just lovely, the view off the terrace was amazing. We had the pool (one of 2) to ourselves everyday. We never heard any of our neighbors. Although the beach was not manicured, the unit was very close to 2 beaches, if you want to sit in the sand.
    We could see cruise ships and parasailing right off the pation. I can't say enough, it was GREAT.

    $450

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    Villa Paradiso: A unique mid-town paradise

    Key West house
    3 BR / 3 BA / Sleeps 6 | Quick view
    Excellent35 Reviews

    Details

    Reviews

    (35)

    This mid-town Key West home is newly renovated and beautifully decorated in jewel tones of the Mediterranean. It features three bedrooms and three baths. The open living/kitchen area is decorated with rich tones with tropical accents and soft fabrics. The dining room is outside in the attached pavillion with an ornate…
    • Internet Access
    • A/C or climate control
    • Deck
    • Parking
    • Grill
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (35)

    The 3 couples loved this home.

    Left on Jun 18, 2009 for a stay in February 2009

    We chose the Villa because it advertised 3 bedrooms and 3 baths. I would advertise it as 2.5 bedrooms. However, the space worked out very well for the 6 of us. The home is graciously appointed and easy to live in. The small pool area was a perfect gathering spot. There were other decks and seating areas when each of us choses a bit more privacy. The Villa was within walking distance of the …

    $1,000

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    DREAMING ON DUVAL- Luxury 5 Bed & Private Pool- As seen on HGTV House Hunters

    Key West house
    5 BR / 4 BA / Sleeps 12 | Quick view
    Excellent20 Reviews

    Details

    Reviews

    (20)

    Luxury on Duval Street in historic Key West? Luxury is not what most people visiting Key West associate with Duval Street until you look at Dreaming On Duval! There are very few private homes on Duval, let alone a single family vacation rental that is steps away from everything Key West has to offer and accommodates …
    • Hot Tub/Jacuzzi
    • Internet Access
    • A/C or climate control
    • Balcony or terrace
    • Parking
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (20)

    Fabulous...

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

    Dreaming in Duval is a beautiful, spacious home. The home is very well equipt,and accomodated 10 people easily.
    The location was perfect, we could walk to everything.
    Dean and Paul were both great and very helpful.
    One of our best vacations ever, we are already planning a return trip.

    $290

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    Beach Club #104 - Unique oceanfront living with breathtaking views

    Key West condo
    2 BR / 2 BA / Sleeps 6 | Quick view
    Excellent15 Reviews

    Details

    Reviews

    (15)

    Unique oceanfront living only 65 feet from the Atlantic! The Key West Beach Club is a quiet, peaceful residential building that sits directly on the water. The breathtaking view can be seen as soon as you enter the unit. The huge oceanfront balcony can be accessed from both the living/dining area and master …
    • Ocean or water views
    • Shared outdoor pool (unheated)
    • Internet Access
    • A/C or climate control
    • Balcony or terrace
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (15)

    Good facility overall, but lots of rules for teeneagers

    Left on Apr 16, 2011 for a stay in March 2011

    Beach Club #104 is nicely and recently decorated. Everything was in good working order (TVs, washer/dryer, kitchen appliances). The cleaning service could have done a better job. There are a number of loose floor tiles which could be dangerous for older renters. The public areas are well kept, but there are some rather draconian rules -- the owners are not particularly friendly and I have to …

    $320

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    Havana Lane: A classic conch cottage with rustic charm

    Key West house
    2 BR / 2 BA / Sleeps 4 | Quick view
    Excellent30 Reviews

    Details

    Reviews

    (30)

    Thoughtfully restored, Havana Lane hearkens back to a time when cigar makers lived in the neighborhood, gathering on porch stoops to pass on the latest news. Near the notorious Key West Cemetery, this classic conch cottage embodies the essence of rustic charm while offering modern amenities and style. Centrally …
    • Internet Access
    • A/C or climate control
    • Deck
    • Grill
    • Linens Provided
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (30)

    Gorgeous surroundings, comfortable Key West home

    Left on Jun 18, 2009 for a stay in April 2009

    As soon as we unlocked the gate to the high wooden fence surrounding 1
    Havana Lane, we knew we had picked a gem of a place to stay for Spring Break.
    My husband and I came to Key West with our 15 year-old daughter and her
    friend. The home was perfect for us four, and we enjoyed being there almost
    as much as going out and about the island. We called the yard our "Secret
    Garden." It was so lush…

    $334

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    Elizabeth Retreat: A three bedroom historic home in Old Town

    Key West house
    3 BR / 2 BA / Sleeps 6 | Quick view
    Very Good3 Reviews

    Details

    Reviews

    (3)

    30 DAY MINIMUM RENTAL Walk the historic streets of Key West, live in Old Town in a quiet residential neighborhood. Just two blocks from Duval Street, it is a quick walk or bike ride to all of Key West's attractions, including it's close proximity to the Historic Seaport area. This is an lovingly restored eyebrow 3 …
    • Internet Access
    • A/C or climate control
    • Patio
    • Parking
    • Grill
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (3)

    A month in Key West

    Left on Jun 18, 2009 for a stay in January 2009

    We had an absolutely delightful time! We have been renting homes in the Keys for years and found this to be our best experience yet. The folks at Rent Key West were so helpful - really stayed on top of everything and went out of their way to accomodate our schedule on check in and check out. The house was absolutely lovely and clearly well cared for. We liked it so much, we are coming back …

    1 / 21

    $440

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    Namaste : A blissful one bedroom cottage designed with relaxation in mind.

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

    Details

    Tucked away in an inviting compound you'll find a blissful retreat called Namaste; a tranquil and relaxing one bedroom cottage. The quiet compound is located just one block from Duval Street combining the best of both worlds for relaxing and taking advantage of all that Key West has to offer. Within 2 blocks you'll …
    • Shared outdoor pool (unheated)
    • Internet Access
    • A/C or climate control
    • Balcony or terrace
    • Linens Provided
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask
    1 2345
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