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$215

1 BR / 1 BA / Sleeps 2

15 Reviews

$215

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The Courtyard

1 BR / 1 BA / Sleeps 2 | Quick view
“ Excellent ” 15 Reviews

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Reviews

(15)

Vacation ever so comfortably in this well-designed one bedroom, one-full-bath courtyard unit at Campbell Court. You can step off your front porch and up to the deck of the enticing, heated, residents-only Monaco pool. Steps to the right, you'll find a raised deck with table, chairs, and shade umbrella above. Tropical …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for the elderly - ask

Details

Reviews

(15)

Convenient and Well-Organized

Left on Feb 07, 2010 for a stay in January 2010

The unit was extremely efficient and all appliances worked as they should - from heat to air-conditioning. The bath area with the washer/dryer was extremely organized with a deep washing machine. The master bed was very comfortable! I really liked the whole layout and the privacy of the unit. I liked going out on the patio and not seeing or having to speak with anyone.

It was an extremely …

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$468

4 BR / 2 BA / Sleeps 12

1 Reviews

$468

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"SEAPORT SUITE" - Great Party House w/ Hot Tub! 1 Min Walk to Sloppy Joe's

4 BR / 2 BA / Sleeps 12 | Quick view
“ Poor ” 1 Reviews

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Reviews

(1)

Seaport Suite is available for daily or weekly vacation rentals and located on the second floor of 219 Simonton in Old Town Key West. The location is as close to perfect as you can get, being one block off Duval Street and within walking distance to every single thing you could possibly want to do. With four bedrooms …
  • Hot Tub/Jacuzzi
  • 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

(1)

Seaport Suite not the place to stay

Left on Dec 02, 2014 for a stay in November 2014

Rental agents were very helpful can't complain about them or the maintenance staff. The property was not in the best shape. washer dryer didn''t work , had to have it replaced. One bathroom did not drain properly so when showering you could also take a bath. Ants all over the kitchen and bathrooms. Not impressed for the price I paid.

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$103

1 BR / 1 BA / Sleeps 4

Topsail Cottage Key West ~ Monthly Rental - Key West vacation rentals
1 / 16

$103

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Topsail Cottage Key West ~ Monthly Rental

1 BR / 1 BA / Sleeps 4 | Quick view

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Island living is made easy in this tropical one bedroom, 2-story Key West cottage. A classic-contemporary Key West style, this attractive rental home is designed with a graceful spiral stair case that connects the 1st and 2nd floors and a romantic gingerbread Juliet-style 2nd floor balcony overlooking a private …
  • Internet Access
  • Housekeeping Optional
  • A/C or climate control
  • Satellite or cable TV
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$227

3 BR / 3 BA / Sleeps 6

2 Reviews

$227

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"VILLA AZUL" Luxurious Monthly Home w/ Pvt Pool, Deck & Gorgeous Interior.

3 BR / 3 BA / Sleeps 6 | Quick view
“ Excellent ” 2 Reviews

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Reviews

(2)

***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** You will certainly enjoy this wonderful historic home with recent renovations, perfectly placed pool, and plenty of outdoor living space located at 1116 Curry Lane. This home is situated in the heart of Old Town, just 4 blocks …
  • Internet Access
  • A/C or climate control
  • Deck
  • Fitness Room
  • Grill
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

Beautiful and comfortable home

Left on Jan 27, 2011 for a stay in December 2008

Villa azul is a wonderfully decorated and appointed home in the historic Old Town section of Key West. The home and grounds were beautiful, serene, private and cozy. It is hard to imagine that this property would not exceed anyone's expectations.

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$378

3 BR / 3 BA / Sleeps 8

6 Reviews

$378

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"ALMOST SOUTHERNMOST TOO" - Private Pool - Half Block To Duval St! Sleeps 8

3 BR / 3 BA / Sleeps 8 | Quick view
“ Excellent ” 6 Reviews

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Reviews

(6)

Part of ALMOST SOUTHERNMOST RETREAT Almost Southernmost Too in the 400 block of Truman Avenue is the perfect location, located between Duval Street and Whitehead St. Just around the corner from Hemingway's House and the Historic Lighthouse Museum, Almost Southernmost Too is a perfect example of shotgun architecture …
  • Internet Access
  • A/C or climate control
  • Patio
  • Fitness Room
  • Grill
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(6)

Fantastic, wonderful experience.

Left on Nov 23, 2011 for a stay in November 2011

Great location, in the center of KeyWest. Parked the car and walked,biked,trollied everywhere. Beautiful color scheme, every room was vibrant with a South Florida palat. Fantastic new kitchen and pool. Spent many hours on the pool patio with a 6-toe cat from the Hemmingway house. Just an all around wonderful experience. We will return to this house again in 2013...Thanks for making this a …

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$255

2 BR / 2 BA / Sleeps 4

3 Reviews

$255

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Banana Key

2 BR / 2 BA / Sleeps 4 | Quick view
“ Excellent ” 3 Reviews

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Reviews

(3)

Impressive. Distinctive. Comfortable. The perfect spot for your tropical getaway. This second-story, two-bedroom, two full bath Harbour Place condominium is a part of Key West's prestigious Truman Annex community. From the luxurious pool area one floor below, you can enjoy breathtaking views just steps from the Gulf …
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Suitable for the elderly - ask

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Reviews

(3)

Better than the pictures!!!

Left on Jan 11, 2012 for a stay in December 2011

We absolutely loved the apartment and the fantastic walk behind the apartment that lead to Duval Street. If we could retire in Key West, this apartment is perfect. The master bedroom was so private, we barely noticed our two daughters in their room. The only complaint would be that the internet signal was weak and we a few problems with that.

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$275

2 BR / 2 BA / Sleeps 4

20 Reviews

$275

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La Prive

2 BR / 2 BA / Sleeps 4 | Quick view
“ Excellent ” 20 Reviews

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Reviews

(20)

This is the real deal-a light, airy, well-appointed Key West townhome with two stories, two bedrooms, two full baths, and all the amenities needed to enhance your vacation lifestyle. Not to mention a large private deck and an inviting pool for the exclusive use of compound residents. La Prive has all this plus close …
  • Shared outdoor pool (unheated)
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Suitable for the elderly - ask

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Reviews

(20)

Excellent - all that we needed

Left on Jun 07, 2011 for a stay in May 2011

This vacation rental was probably the only feature in Key West that was completely as advertised. The rental had everything we needed, to include a blender. Staff was completely courteous and friendly. Rental was only a few blocks from Duval and beaches. Parking spot was spacious. We will always recommend this rental to friends. 5 stars all the way around - and I am a hard reviewer. The rental …

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$888

5 BR / 4 BA / Sleeps 12

1 / 32

$888

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"ABBEY ROAD" Great for Big Parties! - 4 Luxury Units - 4 Private Hot Tubs

5 BR / 4 BA / Sleeps 12 | Quick view

Details

Abbey Road - Gated Compound, Sleeps up to 12! Lennon's Lodge (Sleeps 6 with 8 person hot tub), McCartney's Manor (Sleeps 2 with 2 person hot tub), Starr's Suite (Sleeps 2 with 2 person hot tub) and Harrison's Hideaway (Sleeps 2 with 2 person hot tub) and will accommodate up to 12 persons for the ultimate in …
  • Hot Tub/Jacuzzi
  • 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

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$350

3 BR / 2 BA / Sleeps 6

1 / 19

$350

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

3 BR / 2 BA / Sleeps 6 | Quick view

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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

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$400

2 BR / 2 BA / Sleeps 6

17 Reviews

$400

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The Meadows House

2 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 17 Reviews

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Reviews

(17)

If you choose this two-bedroom, two plus bath home for your Key West vacation, you won't be sorry. While Key West has some fourteen neighborhoods, locals identify The Meadows area, your vacation neighborhood, as the most neighborly. Here you'll find houses with a statistically high year-around residency, relatively …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for the elderly - ask

Details

Reviews

(17)

Week In Key West

Left on Aug 16, 2011 for a stay in July 2011

The house was very nice, the back yard/pool
were great...Enjoyed it very much.
Check in & out very easy.

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$268

2 BR / 2 BA / Sleeps 6

1 Reviews

$268

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SOUTHERN CROSS @ TROPICAL VILLAGE - Beautifully Updated Home w/ Shared Pool.

2 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 1 Reviews

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Reviews

(1)

Part of TROPICAL VILLAGE Southern Cross: Sitting next to the lily pond with fountain or lounging in the shade of your own Royal Poinciana tree, Southern Cross is the perfect place to relax in paradise. This one and a half story vacation cottage is surrounded by exotic gardens, and situated in the Tropical Village …
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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Reviews

(1)

Tropical Perfection

Left on Oct 07, 2014 for a stay in October 2014

The property was clean, the kitchen was equipped with all the necessities, great private porch and shared pool. Location is great - just a couple blocks from Duval and a 15 minute walk to the Mallory Square. Higgs Beach was a close, great market nearby, and a CVS, you really couldn't have asked for a better location! The trip was epic, relaxing and wild from start to finish. I can't wait to come …

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$743

3 BR / 4 BA / Sleeps 6

1 / 22

$743

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The Water's Edge

3 BR / 4 BA / Sleeps 6 | Quick view

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Bring more luminescence into your next vacation with evening after evening of incomparable Key West sunsets viewed from the third-floor deck of this spectacular private home. Called The Water's Edge because of its location at the edge of the Gulf of Mexico, this lovely and comfortable three-bedroom, four-bath lies …
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area

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$180

1 BR / 1 BA / Sleeps 2

16 Reviews

$180

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Key West Garden House

1 BR / 1 BA / Sleeps 2 | Quick view
“ Excellent ” 16 Reviews

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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.

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$700

3 BR / 3 BA / Sleeps 7

7 Reviews

$700

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"SECRET VILLA" 1.5 Blocks to Duval Street - Pool

3 BR / 3 BA / Sleeps 7 | Quick view
“ Excellent ” 7 Reviews

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Reviews

(7)

Key West Vacation Rental "SECRET VILLA" A Hidden Jewel in Historic Old Town Key West Location, Location, Location....This amazing property is situated on a quiet and peaceful lane away from traffic and noise. The secret location is also just a few blocks from everything Key West has to offer; fine dining, nightlife…
  • Waterfront
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Suitable for the elderly

Details

Reviews

(7)

Secret Villa - Fabulous

Left on Apr 26, 2014 for a stay in April 2014

Wonderful location - quiet, tucked away yet only two blocks from Duval. The house is beautifully decorated -outdoor deck and pool area is superb. Have stayed in a number of luxury Key West vacation rentals over the years and this is by far the best. Carlos was a wonderful host and it was so good to meet Jim, the actual property owner.

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$190

3 BR / 3 BA / Sleeps 6

1 Reviews

$190

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"CLUB CLARK" Gorgeous 3 Bd 3 Bth Home w/ Pvt Pool. Close to Dante's!

3 BR / 3 BA / Sleeps 6 | Quick view
“ Excellent ” 1 Reviews

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Reviews

(1)

***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** The main dwelling includes a beautiful, newly-renovated kitchen, a master bedroom with en-suite, a second bedroom with twin beds (which can be made into a king upon request), a full guest bathroom including a tub and full …
  • Internet Access
  • A/C or climate control
  • Patio
  • Grill
  • Linens Provided
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

Club Clark

Left on Apr 10, 2014 for a stay in March 2014

The place was really nice and the staff was very easy to work with. It was a very good vacation and would definitely like to stay there again.

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$250

1 BR / 1 BA / Sleeps 2

68 Reviews

$250

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Rose Cottage

1 BR / 1 BA / Sleeps 2 | Quick view
“ Excellent ” 68 Reviews

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Reviews

(68)

Old Key West style defines this charming Bahamian Colonial studio hidden away on Rose Lane, which runs only one block from Simonton to Duval. The building right next door on Simonton, Casa Antigua, was Hemingway's first island residence, where in 1928 he wrote Farewell to Arms. Going the other way, the lane intersects…
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for the elderly - ask

Details

Reviews

(68)

Great Getaway Spot

Left on Sep 23, 2008 for a stay in April 2008

I am working in Iraq and had just a short time for a break, dreamt about a place with a pool down in the Keys.
This location sounded great - and it lived up to our expectations. Everything worked, it was spotless, it had all the amenities, it was completely private and just a short walk from the main street of Key West. Outstanding location. The back yard was great, there were no bugs, the ladder…

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$215

1 BR / 1 BA / Sleeps 3

42 Reviews

$215

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Ann Street Gardens

1 BR / 1 BA / Sleeps 3 | Quick view
“ Excellent ” 42 Reviews

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Reviews

(42)

(Ann Street Gardens is a 16+ compound. Regretfully, no children under 16 allowed.) The cottage is a cozy hideaway. The poolside area is picture-postcard perfect. The location is in the very heart of Key West's Old Town, a half a block off the world-famous Duval Street. In short, Ann Street Gardens offers the …
  • Shared outdoor pool (unheated)
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Suitable for the elderly - ask

Details

Reviews

(42)

The Great Escape

Left on May 02, 2009 for a stay in March 2009

Location, Location, Location: One block from Duval Streets north end, three blocks to Mallory Square, The Westin,The Hyatt and Pier House, Historic Seaport Boadwalk, multiple wonderfull musuems. No need for any form of city transportation. The best of Key West is 10 minutes(at most)away by foot..even a beautiful public beach at the end of Simenton, two well equiped grocery stores and a …

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$700

4 BR / 3 BA / Sleeps 8

15 Reviews

$700

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Admiral's Lane

4 BR / 3 BA / Sleeps 8 | Quick view
“ Excellent ” 15 Reviews

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Reviews

(15)

As part of the Truman Annex, this stately four-bedroom, three-bath home on Admiral's Lane is tucked away in the beauty and privacy of thick tropical foliage. The Annex neighborhood, named for President Harry Truman who wintered at The Little White House just blocks away, is Old Town's premiere gated waterfront …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for the elderly - ask

Details

Reviews

(15)

Excellent experience

Left on May 11, 2010 for a stay in March 2010

Beautiful accommodations, helpful and friendly staff, and excellent experience
overall. Highly recommend both the house and the management company.

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$175

2 BR / 2 BA / Sleeps 5

6 Reviews

$175

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Sunrise at Seaside Condo 2 Bedroom

2 BR / 2 BA / Sleeps 5 | Quick view
“ Excellent ” 6 Reviews

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Reviews

(6)

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
  • A/C or climate control
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(6)

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 …

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$140

1 BR / 1 BA / Sleeps 4

1 / 12

$140

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Conch Haven Built 1883 Beautiful ! MONTHLY Rental

1 BR / 1 BA / Sleeps 4 | Quick view

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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

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$157

3 BR / 3 BA / Sleeps 8

1 / 26

$157

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"BEACH CLUB BREEZE" Monthly Rental - Two Story Home w/ Sun Deck & BBQ Grill

3 BR / 3 BA / Sleeps 8 | Quick view

Details

***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** This well-manicured, "home away from home" is two stories of wonderful! It has 3 bedrooms, 3 baths and has a colorful, comfortable style. The traditional white picket fence greets you when you arrive. Though, it's only a …
  • Internet Access
  • A/C or climate control
  • Patio
  • Fitness Room
  • Grill
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$748

4 BR / 4 BA / Sleeps 16

1 / 30

$748

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Palm Gardens - Great for Groups!

4 BR / 4 BA / Sleeps 16 | Quick view

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The Condos are tied together in a lushly landscaped garden setting with a spa pool in the rear. Booking all 4 condos gives you a great alternative to booking a single house as you are offered privacy and closeness at the same time. Call to book your Island Paradise while there is still time! Palm Gardens is …
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Fitness Room
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$133

2 BR / 5 BA / Sleeps 4

1 / 14

$133

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Buoy's Backyard

2 BR / 5 BA / Sleeps 4 | Quick view

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MONTHLY RENTAL ONLY Buoy's Backyard - an authentic Key West retreat in the historic district just a block from upper Duval (the quiet end), two blocks from Hemingway House, and three blocks to Southernmost Buoy and Beach. Brick driveway provides private gated parking for two cars. This home has 2 buildings …
  • Wireless Internet
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Pet friendly - ask
  • Suitable for children - over five
  • Wheelchair accessible

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$1,448

11 BR / 9 BA / Sleeps 32

1 / 32

$1,448

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TROPICAL VILLAGE 6 Homes w/ Pvt Pool & BBQ Grill. Great For Large Parties!

11 BR / 9 BA / Sleeps 32 | Quick view

Details

Tropical Village is comprised of 6 separate vacation rentals properties that can also be rented separately. COTTAGE @ TROPICAL VILLAGE POOLSIDE @ TROPICAL VILLAGE SOUTHERN CROSS @ TROPICAL VILLAGE TOON HALL @ TROPICAL VILLAGE RETREAT @ TROPICAL VILLAGE HIDEAWAY @ TROPICAL VILLAGE Located at 706 and…
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$408

3 BR / 2 BA / Sleeps 10

13 Reviews

$408

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"POOLSIDE PARADISE" Amazing Home 1/2 Block to Duval w/ Pool and Pvt Parking

3 BR / 2 BA / Sleeps 10 | Quick view
“ Excellent ” 13 Reviews

Details

Reviews

(13)

POOLSIDE PARADISE is made up of POOLSIDE RETREAT and POOLSIDE SUITE With 3 bedrooms (K, 2 Q, plus 2 Q sleeper), 2 full baths and 2 full kitchens, this historic home is perfect for up to 10 persons. The front portion features a King bedroom, a Queen bedroom and a Queen sleeper sofa in the living room. The bath with …
  • Internet Access
  • A/C or climate control
  • Deck
  • Fitness Room
  • Grill
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(13)

Enjoyed our Stay

Left on Oct 14, 2011 for a stay in September 2011

The place was perfect for our group. My husband and I traveled with my parents and another couple. It worked out great because the parents stayed with us and our friends had their own little apartment which gave us all our privacy if needed. The location was pretty nice as well. We were one block off Duval. Even though we were down on the end closest to SouthernMost everything was within …

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$233

2 BR / 2 BA / Sleeps 4

1 Reviews

$233

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Pinder House - Monthly Rental

2 BR / 2 BA / Sleeps 4 | Quick view
“ Very Good ” 1 Reviews

Details

Reviews

(1)

***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Located at 516 Elizabeth Street, the Pinder House is an address and house of distinction! Previously owned by Theopolis Pinder of the historic Pinder Family, whose roots go back to the 1850’s, this historic Eyebrow home has …
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Central heating
  • Balcony or terrace
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

Live in an 1830's house w / 2014 conveniences

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

B+ no Choices in cable channels no prkg
On site , parrot sanctuary adjacent
Property's remote pool. Access. K

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$153

2 BR / 2 BA / Sleeps 4

1 / 7

$153

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Governor's Retreat ~ Monthly Rental

2 BR / 2 BA / Sleeps 4 | Quick view

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This gentle Governor's Retreat in the Key West Meadows is an immaculate luxury vacation rental cottage ideal for a quiet couple or single person with discerning taste. The property is the perfect Key West setting for rest, relaxation, and rejuvenation. It is ideal for the person of distinction who is looking for …
  • Internet Access
  • Satellite or cable TV
  • Telephone
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$268

2 BR / 2 BA / Sleeps 6

1 / 31

$268

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THE COTTAGE @ TROPICAL VILLAGE - Spacious Home w/ Shared Pool. Close To Beach

2 BR / 2 BA / Sleeps 6 | Quick view

Details

Part of TROPICAL VILLAGE Tropical Village Cottage - is a two bedroom, two bath vacation cottage that overlooks a large shared seasonally heated pool, sun-deck and pool-side grilling station. With all the amenities of contemporary living set in island style and decor. Tropical Village Cottage is your ticket to a …
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$215

2 BR / 2 BA / Sleeps 6

1 / 4

$215

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Key West Hyatt Windward Pointe

2 BR / 2 BA / Sleeps 6 | Quick view

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The Hyatt Windward Pointe is the most luxurious accommodation in Key West. One king bedroom suite with ocean views, queen bedroom and sleep sofa (accommodates 6), Full kitchen, balcony with ocean views, W/D in unit, TV in every room, large pool and hot tub, volleyball court, amazing landscaping. This unit rents …
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

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$188

1 BR / 1 BA / Sleeps 4

23 Reviews

$188

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"VERDE SUITE" - Quiet & Affordable 'Old Town' Cottage - Shared Pool

1 BR / 1 BA / Sleeps 4 | Quick view
“ Excellent ” 23 Reviews

Details

Reviews

(23)

The location is ideal in that it is just two blocks from the action of Duval street, yet has the tranquility and peacefulness to nap on the outside deck. This immaculately clean and comfortable air conditioned suite features beautiful vaulted ceilings and pastel colored walls as well as a top of the line flat screen …
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Patio
  • Fitness Room
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(23)

Verde Suite relaxation

Left on Jun 25, 2009 for a stay in April 2009

Glorius week in a great little suite with almost everything you would want. The only thing missing was the availability of authorized parking although there are parking spaces adjacent to the complex that remained vacant the entire week
Everything else ranks high. Cleanliness, secluded, close to everything in Old Town.

Would I do it again? In a heartbeat....as a matter of fact I am planning a …

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$408

3 BR / 2 BA / Sleeps 10

2 Reviews

$408

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"TOON HALL @ TROPICAL VILLAGE" - Great For Large Groups. Close to ATL Ocean!

3 BR / 2 BA / Sleeps 10 | Quick view
“ Excellent ” 2 Reviews

Details

Reviews

(2)

Part of TROPICAL VILLAGE Toon Hall: World-class comfort, lush tropical surroundings and unmatched privacy characterize the former winter home of Pulitzer Prize winning cartoonist, author and artist, Jeff MacNelly. Designed to accommodate a large family or group, this three bedroom home has two full baths plus the …
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

Best vacation ever!

Left on Jul 01, 2014 for a stay in June 2014

We took our family of 6 to Toon Hall and were greeted by 2 Cadillac SUV's at the airport to check us in and take us to our home. Toon Hall was very spacious and comfortable, perfectly situated blocks from the beach and Duvall Street. We were able to chill and grill at home by our pool or walk into town for a night of fun.We also loved the privacy and security the fenced yard offered.

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$275

2 BR / 2 BA / Sleeps 6

1 Reviews

$275

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Penthouse Condo in Key West Florida

2 BR / 2 BA / Sleeps 6 | Quick view
“ Average ” 1 Reviews

Details

Reviews

(1)

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
  • Balcony or terrace
  • Parking
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

Details

Reviews

(1)

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

2 BR / 3 BA / Sleeps 6

1 / 11

$258

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Island Brownstone ~ Weekly Rental

2 BR / 3 BA / Sleeps 6 | Quick view

Details

An exclusive island style brownstone perfectly nestled in Key West's most prominent gated waterfront neighborhood known as "Truman Annex", this striking tri-level historic building has all the architectural allure of a 19th century urban brownstone with an unparalleled modern Caribbean reinterpretation. …
  • A/C or climate control
  • Porch
  • Grill
  • Television
  • Stereo or CD player
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$408

2 BR / 2 BA / Sleeps 6

9 Reviews

$408

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HELEN'S HIDEAWAY - Gated, Unique, 2 BR House W/ Private Heated Pool

2 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 9 Reviews

Details

Reviews

(9)

This gem is located at the end of a hidden lane, just off Simonton Street, behind The Gardens Hotel. Helen's Hideaway is a step back in time to Key West during its slumbering past. Built by David Wolkowski, who built many of Key West's premier resorts, including the Pier House, this paradise reflects his passion for …
  • Internet Access
  • A/C or climate control
  • Deck
  • Fitness Room
  • Grill
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(9)

Quiet, private, unique concept, but big price for significant di

Left on Sep 12, 2013 for a stay in September 2013

Truly a hideaway! Very private-locked behind a wooden fence. Location-excellent! Fun detached bedroom w/a wall of sliders that open to the private pool. Outdoor hot/cold shower well placed amidst foliage for privacy. Sufficiently equipped kitchen, but outdated & narrow - two large people may have trouble passing each another. 3 flat screens. Lg bathroom in main bldg recently redone with huge walk…

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$540

3 BR / 2 BA / Sleeps 6

1 / 18

$540

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Casa de Cuba:Beautiful home loaded with style and elegance

3 BR / 2 BA / Sleeps 6 | Quick view

Details

Location! Style! Elegance! This beautiful home is the fabulous combination of everything a great vacation property should be. One half block to Duval Street in the historic district, the location can't be beat. The home's history is rich; neighboring the historic Gato Cigar factory which is now restored and used as …
  • Internet Access
  • A/C or climate control
  • Patio
  • Parking
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$83

2 BR / 2 BA / Sleeps 6

1 / 24

$83

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"SALT POND HIDEAWAY" 2/2 Condo w/ Huge Shared Pool & Hot Tub. Close to Beach!

2 BR / 2 BA / Sleeps 6 | Quick view

Details

***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Salt Pond Hideaway is located right off of South Roosevelt Blvd. in the oceanfront Salt Ponds Condominium Complex. It offers a neighborly and relaxing atmosphere with the ocean breezes of the Atlantic right across the …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Deck
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$184

2 BR / 1 BA / Sleeps 4

4 Reviews

$184

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"LAZY LANE" - WEEKLY OR MONTHLY(Truman Annex) - Color and Style Front to Back

2 BR / 1 BA / Sleeps 4 | Quick view
“ Very Good ” 4 Reviews

Details

Reviews

(4)

***Due to licensing restrictions, this property requires a minimum stay of 7 nights.*** The spacious living room/dining room features a with large flat screen TV and DVD player. Living room French doors open up into the private deck which features outdoor seating and a Gas BBQ Grill, making your vacation a true …
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Deck
  • Fitness Room
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(4)

261 Lazy Lane- Vacation!!!

Left on Nov 14, 2013 for a stay in October 2013

The condo was clean and had all of the necessary items needed for a 10 day stay (cleaning products, laundry, etc). It was a nice place to stay and would stay there again next time

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$198

2 BR / 2 BA / Sleeps 6

1 / 25

$198

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SAINT MARTIN SUITE #207 - 2/2 Condo w/ Pool & Hot Tub - Near Smathers Beach

2 BR / 2 BA / Sleeps 6 | Quick view

Details

Sunrise Suites Resort is an island paradise. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped pool surrounded by lush tropical foliage where you can let your cares melt away. Please take a moment to look through our site at our many amenities, the …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$83

2 BR / 2 BA / Sleeps 4

1 / 23

$83

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Playa Royale - Monthly Rental

2 BR / 2 BA / Sleeps 4 | Quick view

Details

***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Playa Royale is located on South Roosevelt Blvd., directly across from Key West's largest beach (Smathers) on the Atlantic Ocean. You can choose to join in activities held in the club house overlooking the pool, tennis courts …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Sauna
  • Internet Access
  • A/C or climate control
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$788

5 BR / 4 BA / Sleeps 12

1 / 24

$788

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"SOUTHERN PALMS" Historical Hideaway - Bahama Village - 2 Hot Tubs & Pvt Pool

5 BR / 4 BA / Sleeps 12 | Quick view

Details

Located at 729 Whitehead St, "Southern Palms" is the group property consisting of the following homes Coconut Palm formerly Island Oasis Traveler's Palm formerly Palm Isle Royal Palm formerly Little Palm which can all be booked individually. All together, these three units have 5 separate bedrooms, 3 …
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$288

3 BR / 2 BA / Sleeps 6

1 / 10

$288

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Southernmost Retreat- 1 Block from Duval

3 BR / 2 BA / Sleeps 6 | Quick view

Details

Just 1 short block from Duval Street the Southernmost Retreat is a recently renovated and decorated 3 bedroom, 2 bath house located Simonton Street. The Southernmost Retreat is located in the Simonton Historic Cottages enclave and is surrounded by fine restaurants, art galleries, shopping and in the center of the Old…
  • Internet Access
  • Housekeeping Optional
  • Outdoor Dining Area
  • A/C or climate control
  • Porch
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly

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$198

2 BR / 2 BA / Sleeps 6

1 / 26

$198

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RUM CAY SUITE #304 - 2/2 Condo w/ Pool & Hot Tub - Near Smathers Beach

2 BR / 2 BA / Sleeps 6 | Quick view

Details

Sunrise Suites Resort is an island paradise. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped pool surrounded by lush tropical foliage where you can let your cares melt away. Please take a moment to look through our site at our many amenities, the …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$515

3 BR / 3 BA / Sleeps 5

1 Reviews

$515

Inquire

Ocean Retreat

3 BR / 3 BA / Sleeps 5 | Quick view
“ Excellent ” 1 Reviews

Details

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 …

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$188

1 BR / 1 BA / Sleeps 4

2 Reviews

$188

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Flamingo Hideaway - Private hot tub, Lush landscape

1 BR / 1 BA / Sleeps 4 | Quick view
“ Very Good ” 2 Reviews

Details

Reviews

(2)

Part of the Nightly Group PALM GARDENS Flamingo Hideaway is a spacious unit. Historic homes dating to the late 1880s, this tropical paradise has just undergone a complete restoration with exceptional attention to details. The original Dade County pine walls have been saved to create that unique historic feel…
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Patio
  • Fitness Room
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

The home was great, the service was awful.

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

The home we stayed in (905 White street- Flamingo) was wonderful. It was very clean, well kept and a great getaway from the business of Duval Street. We rented bikes so we only had a short bike ride to get to a store, bar or beach. The only problem was the service we received. It started at the beginning of the trip when we were rudely spoken to on the phone when we had no idea how to get into …

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$188

1 BR / 2 BA / Sleeps 4

21 Reviews

$188

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"THE AUDUBON HOUSE" Customer Favorite! Great Location 1 Block To Duval

1 BR / 2 BA / Sleeps 4 | Quick view
“ Excellent ” 21 Reviews

Details

Reviews

(21)

AUDUBON'S LIVING ROOM HAS JUST BEEN REFURBISHED WITH NEW FURNITURE INCLUDING NEW CHAIRS AND A NEW QUEEN SLEEPER SOFA! The Audubon House is an historic free-standing one bedroom cottage featuring all the comforts of home, and more! The spacious, beautifully furnished great room features a living room. The dining …
  • Internet Access
  • A/C or climate control
  • Patio
  • Fitness Room
  • Grill
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(21)

Nice, but

Left on Jun 24, 2009 for a stay in February 2008

The home was nice and well maintained. It had all the amenities it said it did, but the pool was away a bit and across the street and was very small with little if any sun, so we ended up not using it at all and going to the beach. This house is in the area where the roosters wake you up early in the morning. Too early for vacation. The master bedroom is tight -- the bed is cramped and closet …

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$200

3 BR / 3 BA / Sleeps 7

1 / 16

$200

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Luxurious Manor ~ Monthly Rental

3 BR / 3 BA / Sleeps 7 | Quick view

Details

Live in the lap of luxury in this stunningly renovated Key West classic "Eyebrow House." An esteemed Key West renovation builder assembled a creative team of elite woodworkers, masons, local craftspeople, and an internationally known traveling artist / sailor to execute his plans to create this Luxurious …
  • A/C or climate control
  • Parking
  • Satellite or cable TV
  • Stereo or CD player
  • Telephone
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$750

4 BR / 3 BA / Sleeps 8

1 Reviews

$750

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By The Beautiful Sea ~ Weekly Rental

4 BR / 3 BA / Sleeps 8 | Quick view
“ Very Good ” 1 Reviews

Details

Reviews

(1)

If you've been searching for a private home overlooking the tropical turquoise sea, you've probably found that nearly all water-view vacation rental properties on Key West are hotels, condominiums, or time-shares, and that it's nearly impossible to find a private Key West house that offers both an open …
  • Internet Access
  • A/C or climate control
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

Location, view, everything you need!

Left on Jun 23, 2014 for a stay in June 2014

Very convenient to all the local sights and everything needed for a reasonably large group of people. Everyone had their space but also a large living/dining/kitchen for gathering. We enjoyed the week!

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$188

1 BR / 1 BA / Sleeps 4

47 Reviews

$188

Book

Osprey’s Nest

1 BR / 1 BA / Sleeps 4 | Quick view
“ Excellent ” 47 Reviews

Details

Reviews

(47)

Part of the Nightly Group PALM GARDENS Historic homes dating to the late 1880s, the tropical paradise has just undergone a complete restoration with exceptional attention to details. Osprey's Nest is an upstairs spacious unit at 905 White Street. The original Dade County pine walls have been saved to create …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Deck
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(47)

Perfect

Left on Jun 24, 2009 for a stay in January 2009

The location is great! Close to everything yet far enough away that you have privacy. The rental was tastefully decorated and clean. Loved everything about it!! Will definitely keep in my Rolodex for future plans!!

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$638

5 BR / 4 BA / Sleeps 16

14 Reviews

$638

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ALMOST SOUTHERNMOST RETREAT Pvt Pool & Hot Tub -1/2 Block to Duval -Sleeps 16

5 BR / 4 BA / Sleeps 16 | Quick view
“ Excellent ” 14 Reviews

Details

Reviews

(14)

Almost Southernmost Retreat is made up of Part of ALMOST SOUTHERNMOST and Part of ALMOST SOUTHERNMOST TOOon the 400 block of Truman Avenue is the perfect location between Duval Street and Whitehead Streets. This style is common throughout the islands. Located in a row of identical cigar-maker cottages, the front …
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Deck
  • Fitness Room
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(14)

Perfect for a large group!

Left on Nov 23, 2011 for a stay in October 2011

We rented the Retreat and love it. We had 11 people (26-29yrs old) at one point and everyone had plenty of room. The location is perfect and having parking spots is a huge plus. Check-in and check-out was painless. Overall I would highly recommend this rental for a large group looking to be close to the action.

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$217

5 BR / 3 BA / Sleeps 18

1 / 24

$217

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"BAY HARBOR VIEW" - Waterfront Monthly Rental w/ Spectacular Views

5 BR / 3 BA / Sleeps 18 | Quick view

Details

***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** a passport tucked away off of mile marker 15. While relaxing in the 20x12 free form lagoon pool, the surrounding scenery makes you feel like you are on your own deserted island. Around the back of the home, the large …
  • Waterfront
  • Internet Access
  • A/C or climate control
  • Patio
  • Fitness Room
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
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