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$215

2 BR / 1 BA / Sleeps 6

The Banyan Resort at Key West - Key West vacation rentals
1 / 6

$215

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The Banyan Resort at Key West

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

Details

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

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$743

3 BR / 4 BA / Sleeps 8

Ocean Paradise - Key West vacation rentals
1 / 25

$743

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Ocean Paradise

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

Details

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

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$408

3 BR / 2 BA / Sleeps 10

3 Reviews

$408

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

Key West house
3 BR / 2 BA / Sleeps 10 | Quick view
Excellent3 Reviews

Details

Reviews

(3)

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

(3)

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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$600

3 BR / 3 BA / Sleeps 6

Sail and Sleep on a Catamaran - Key West vacation rentals
1 / 9

$600

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Sail and Sleep on a Catamaran

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

Details

Price includes taxes. cleaning fee and sunset sail (weather willing). For six or less adults only. You have the use of three of four private cabins each with its own marine style bathroom and queen like bed. Captain Charles and wife Deborah use one cabin.The "ANAA B" is 41ft long and 24ft wide Catamaran (sailboat) …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Smoking allowed - ask
  • Suitable for the elderly - ask

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$145

1 BR / 6 BA / Sleeps 2

Cabin on a 35-foot Sailboat (Key West) - Key West vacation rentals
1 / 5

$145

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Cabin on a 35-foot Sailboat (Key West)

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

Details

We are a young couple with a private cabin on a two cabin sailboat in a Key West marina with a number of amenities (restaurant, bar, gym, lounge). The cabin holds two people comfortably (one double bed). We live on the boat as well in the second cabin. Restrooms and showers are at the bathhouse at the end of the dock…
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Outdoor Dining Area
  • Balcony or terrace
  • Suitable for children - ask

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$238

1 BR / 1 BA / Sleeps 4

1 Reviews

$238

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"PORCHSIDE PARADISE" Private Porch & Hot Tub 1/2 Block To Duval St.

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

Details

Reviews

(1)

Part of Conch Republic Cottages "Porchside Paradise" is located in the front section of the "Conch Republic Cottages". This beautiful 'home away from home' features an inviting and spacious front porch - great for people watching - as well as a private two person hot tub. The unit is gated off from the other …
  • Hot Tub/Jacuzzi
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

Old Key West Home

Left on Apr 21, 2015 for a stay in March 2015

My 1st visit to Key West was in 1971 when it was a small, end of the road, sleepy beach town with old homes & history. Things have changed & it has grown tremendously. One thing that has not iatr the homes. Old buildings from the 60's - 70's are still here but split up into multi-unit apartments within houses. This was one of them. This was the front apartment that was very cute. Small but …

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$575

3 BR / 2 BA / Sleeps 8

6 Reviews

$575

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Abaco Dreams ~ Weekly Rental

Key West house
3 BR / 2 BA / Sleeps 8 | Quick view
Average6 Reviews

Details

Reviews

(6)

Some wonderful changes are happening at the Abaco Dreams vacation rental. From the moment the new owners first stepped inside this beautifully maintained historic home, it was a love story about to unfold. With a passion for Key West wooden homes, they immediately began making furnishing upgrades, with an eye to the …
  • Internet Access
  • A/C or climate control
  • Linens Provided
  • Satellite or cable TV
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(6)

Nice house....bad letting agent!

Left on Jan 03, 2012 for a stay in November 2011

DON'T EXPECT THIS COMPANY TO REPLY TO YOUR CALLS ON ANY OF THEIR TELEPHONE NUMBERS! THEY DON'T PICK UP, NOT EVEN IN THE MIDDLE OF THE NIGHT WHEN THE ALARM SYSTEM IN THE HOUSE IS AT IT'S LOUDEST.

Lovely Key West home, very traditional, as it looks in the brochure. Advertised to take 6, in our view only if 2 are small children. The lovely pool area is set for 4 .. chairs at the table, 4 …

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$408

3 BR / 2 BA / Sleeps 6

31 Reviews

$408

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"CASA SERENDIPITY" - World Class Comfort in Lush, Tropical Paradise

Key West house
3 BR / 2 BA / Sleeps 6 | Quick view
Excellent31 Reviews

Details

Reviews

(31)

Located on one of old town's prettiest historic streets, Frances Street. Casa Serendipity is one of the finest examples of the 'conch cottage' style architecture that Key West is famous for. Designed to accommodate a family, this three-bedroom home has two full baths, one full bath upstairs and one full bath …
  • Internet Access
  • A/C or climate control
  • Deck
  • Grill
  • Linens Provided
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(31)

Very quaint

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

Loved the house, nicely decorated and well kept. Lots of room except you
need to watch your head going down the stairs - low clearance. Nice wrap
around porch and yard with small pool (too cold for me but the kids loved it).
The walk to town (Duval St area) was longer than expected especially since the
house is across from the cemetary (above ground).

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$215

1 BR / 2 BA / Sleeps 4

1 / 6

$215

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Coconut Beach

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

Details

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

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$388

2 BR / 3 BA / Sleeps 6

20 Reviews

$388

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"ISLAND OASIS" Luxury 2 BR 2 Bath Townhome w/ Pvt Heated Pool & Pvt Parking

Key West house
2 BR / 3 BA / Sleeps 6 | Quick view
Excellent20 Reviews

Details

Reviews

(20)

The beaches of the Atlantic Ocean are less than a 7 minute blocks away. This ultra luxurious 2 bedroom, 2-1/2 bath, 2 story house has been totally redecorated by one of Key West’s most talented designers, Michael Pelkey. Sitting in a row of 6 townhomes built by Key West's premier builder, Island Oasis will …
  • Internet Access
  • A/C or climate control
  • Deck
  • Grill
  • Linens Provided
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(20)

Great to have our own pool and grill

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

What can be better than leisurely lounging at the pool on the lanai with friends, wine, and shrimp on the bar-b. The owners even provided the boombox :)
The short walk to the strip was the only downfall--a bit unsightly immediately around the unit, but still only a very short stroll to the more quiet end of the street so that you can gradually head up Duval.

Parking was limited but we …

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$100

1 BR / 1 BA / Sleeps 2

1 / 15

$100

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"HEMINGWAYS SHADOW" Beautiful & Modern - Style 1 Bed Condo in Old Town

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

Details

***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Hemingway's Shadow is a well-appointed, 1 bedroom home located on Thomas Street, directly behind the Key West Lighthouse Museum. The living room, dining area and kitchen form an L-shape open area. The kitchen also has a …
  • Internet Access
  • A/C or climate control
  • Dishwasher
  • Microwave
  • Refrigerator
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$198

2 BR / 2 BA / Sleeps 6

1 / 24

$198

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GRAND TURK SUITE #404 - 2/2 Condo w/ Pool & Hot Tub - Near Smathers Beach

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

Details

Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9am - 6pm daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped …
  • 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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$208

4294967295 BR / 1 BA / Sleeps 2

15 Reviews

$208

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"McCARTNEY'S MANOR" Luxury Cottage - Private Hot Tub - 1/2 Block To Duval St!

Key West cottage
1 BA / Sleeps 2 | Quick view
Excellent15 Reviews

Details

Reviews

(15)

Part of 4 exclusive units at Abbey Road, The state-of-the-art kitchen includes granite counter tops, a Jenn-Air 2 burner cook top, dishwasher, under counter refrigerator, microwave and soft mood lighting under and above the cabinets. There is also an ice-maker on site for fresh ice to prepare your tropical drinks in …
  • 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

Details

Reviews

(15)

Best vacation inside us ever!

Left on Sep 06, 2010 for a stay in July 2010

Came down to Key West with my fiancée and wow we were surprised our room the mcarthy manor was wonderful ! The decorated immaculately! Everything was too of the line including the appliances. Never had a problem finding parking for our car. When I come back I won't stay anywhere else! Neither should you! The privacy and beauty of these rooms cant be top anywhere else on the island. And the pool …

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$138

4294967295 BR / 1 BA / Sleeps 2

1 Reviews

$138

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"DECKSIDE SUITE" Studio w/ Shared Hot Tub Steps To Duval St

Key West cottage
1 BA / Sleeps 2 | Quick view
Terrible1 Reviews

Details

Reviews

(1)

Part of Conch Republic Cottages Efficiency at its finest! The Deckside Suite is the perfect vacation rental in Key West for those who are trying to get the most bang for their buck. You have everything you need in this cozy, studio-style unit, including a fully-stocked kitchen, cable TV, free wireless internet, and a…
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

Rats Rats and Rats

Left on Jan 21, 2015 for a stay in January 2015

this is a very small unit... in need of a total make over. and yes there are rats all over the deck and in the walls. We could hear them at night and in the moring we saw 4 run across the deck.... Management (Key West Vacation Rentas)was not concerned simply saying there are rats everwhere in Key West.. It appears that one side of the unit is rented to locals and they helped entertain us by …

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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

Key West cottage
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
  • Deck
  • Grill
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$60

1 BR / 1 BA / Sleeps 4

1 / 14

$60

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737 The Place, a Monthly Rental Old Town Key West

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

Details

Reasonable rates, best for couples and small families, Key West, Private, gated property in Historic Old Town Key West. Fishermen will love smoker grille for their catch. Newly refurbished, tropical furnishings, private deck. Large kitchen with full range and oven, microwave, and toaster oven. Washer/dryer enclosed …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$800

4 BR / 3 BA / Sleeps 10

4 Reviews

$800

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Villa Deja vu Key West ~ Weekly Rental

Key West house
4 BR / 3 BA / Sleeps 10 | Quick view
Excellent4 Reviews

Details

Reviews

(4)

You know that incredible experience of Déjà vu? When you enter someplace for the very first time, and instantly you get that sense that you’ve been there before? When I first visited this vacation rental house, it happened to me. My mind sparked, the place seemed wonderfully familiar, and I felt an…
  • Internet Access
  • Housekeeping Optional
  • A/C or climate control
  • Satellite or cable TV
  • Stereo or CD player
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(4)

Perfectly Private in Key West

Left on Jun 05, 2012 for a stay in June 2012

We just returned from a wonderful trip to Key West and a much anticipated visit with my daughter and her boyfriend. We were also very fortunate to have stayed at a wonderful rental called Villa Deja Vu. From the minute we walked into Villa Deja Vu it was like entering a sweet, happy and quiet place. Every inch of the resident was beautifully decorated in perfect Key West fashion and the most …

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$214

0 BR / 1 BA / Sleeps 2

1 / 16

$214

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Key West Beach Front rental Your Ocean View Studio

Key West condo
0 BR / 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

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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

Key West house
3 BR / 3 BA / Sleeps 8 | Quick view
Excellent6 Reviews

Details

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
  • Balcony or terrace
  • Grill
  • Linens Provided
  • 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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$150

2 BR / 2 BA / Sleeps 4

19 Reviews

$150

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"CASA TORTUGA" Monthly Rental. Tropical Condo w/ Pool. A Few Blocks To Duval.

Key West condo
2 BR / 2 BA / Sleeps 4 | Quick view
Excellent19 Reviews

Details

Reviews

(19)

***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** The master bedroom decorated in Key West styled décor has a queen-size bed and full bathroom with tub. The second bedroom has 2 twin-size beds that can also be converted in to a king upon request. The fully stocked gourmet …
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Deck
  • Fitness Room
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(19)

Great place! Will stay there again!

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

Our entire experience from making the reservation through to the actual stay was great! It was my first trip to Key West and the Mel Fisher Suite was the perfect choice! The check-in process was very smooth and easy. We found the apartment clean, comfortable and fully equipped with everything we needed. It was just a few short blocks to Duvall Street which was perfect! Close to the action …

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$183

2 BR / 2 BA / Sleeps 6

1 / 20

$183

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A Low Key Paradise- Monthly rental only

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

Details

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

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$275

3 BR / 3 BA / Sleeps 8

10 Reviews

$275

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Island Days - Fishing, Boating, Golfing, Dining, Shopping!

Key West house
3 BR / 3 BA / Sleeps 8 | Quick view
Excellent10 Reviews

Details

Reviews

(10)

The Best of Everything! "Island Days" has it all: Large heated resort style pool with Tiki Hut right outside your French doors. Lush landscaping, off street parking steps to your door, all in a private 3 bedroom 3 bathroom town house located in the gated Coral Hammock community just a few minutes from Old Town Key …
  • Shared outdoor pool (unheated)
  • Parking
  • Grill
  • Satellite or cable TV
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(10)

Our fabulous stay at Island Days in Key West

Left on Oct 26, 2013 for a stay in June 2013

I wanted to take my sons and future daughter in-law and her two children to Key West for a week vacation this past summer and had been searching on line for a house or townhouse/condo to rent for our stay. After 1 place falling through I came upon Island Days townhouses. I have to say that it was everything and more! It was decorated beautifully and was exactly as the photos shown! It made me …

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$488

3 BR / 3 BA / Sleeps 10

2 Reviews

$488

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"TRES FLORES" - Private Parking - Just Steps From Duval St - Sleeps up to 10!

Key West condo
3 BR / 3 BA / Sleeps 10 | Quick view
Excellent2 Reviews

Details

Reviews

(2)

Hibiscus Suite is a queen efficiency with a kitchen, bathroom and a small outdoor deck. Orchid and Jasmine are both one bedroom suites with queen bedrooms, queen sleeper sofas, kitchenettes and outdoor decks. All units have TV/DVD, cable and Free WiFi! This complex offers combined parking for 3 vehicles, a BBQ grill …
  • Internet Access
  • A/C or climate control
  • Patio
  • Grill
  • Linens Provided
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

A very clean property for our extended family's trip to Key West!

Left on Jul 28, 2014 for a stay in July 2014

Pictures online are great and the property was perfect for 3 families traveling together. We tried not to be in rooms during the day since we were busy with excursions but the bedrooms were roomy and comfortable. It would be nice to have locks on bathrooms.

The office staff were great and even transported all of our 30+ pieces of luggage while we were eating at Sara Beth's.

It is relatively…

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$325

2 BR / 2 BA / Sleeps 6

1 / 22

$325

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Key West Florida Beachfront Condo

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

Details

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

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$600

3 BR / 3 BA / Sleeps 6

10 Reviews

$600

Inquire

Kemp House

Key West house
3 BR / 3 BA / Sleeps 6 | Quick view
Excellent10 Reviews

Details

Reviews

(10)

This Civil War Era home sits in Key West's most desirable Historic Seaport District, less than a block from the Gulf of Mexico. Did Abraham Lincoln sleep here? Probably not. But anyone staying today in this classic revival valued in the millions will find not only history but every creature comfort and contemporary …
  • Wireless Internet
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for the elderly - ask

Details

Reviews

(10)

very lovely

Left on Feb 09, 2009 for a stay in November 2008

Beautiful house. Near everything. Comfortable and well kept.

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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

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

Details

Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9am - 6pm daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped …
  • 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

PreviousNext property

$558

3 BR / 3 BA / Sleeps 5

1 Reviews

$558

Inquire

Ocean Retreat

Key West condo
3 BR / 3 BA / Sleeps 5 | Quick view
Excellent1 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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$400

2 BR / 2 BA / Sleeps 4

11 Reviews

$400

Inquire

Casa Camilla

Key West house
2 BR / 2 BA / Sleeps 4 | Quick view
Excellent11 Reviews

Details

Reviews

(11)

You'll know you've found island heaven--the term heaven meaning transcendence or going beyond the ordinary--when you enter Casa Camilla. This two-bedroom, two-bathroom home located in the lovely Meadows neighborhood of Old Key West is extraordinary inside and out. The outside rear half of the property is beautifully …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for the elderly - ask

Details

Reviews

(11)

absolutely gorgeous!

Left on Dec 07, 2011 for a stay in November 2011

The house is absolutely beautiful and in a great location; easy to get to Duval street. Very quiet neighborhood. The house had everything except internet access and a heated pool/jacuzzi.

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$450

3 BR / 2 BA / Sleeps 6

8 Reviews

$450

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3 Bedroom Oceanfront Condo Key West

Key West condo
3 BR / 2 BA / Sleeps 6 | Quick view
Excellent8 Reviews

Details

Reviews

(8)

Large 3 Bedroom, 2 Bath OCEANFRONT condo. Breathtaking views of the Atlantic from every room. Tropical landscaped property with large heated pool and Jacuzzi. Just steps to Smathers Beach which has swimming, jet skis, parasailing, etc. Fully appointed condo with all the amenities of home at your fingertips. Sorry …
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Suitable for children

Details

Reviews

(8)

Beautiful oceanfront condo

Left on Jan 11, 2014 for a stay in January 2014

We just rented this unit - it was wonderful!!! Beautiful kitchen,
recently remolded. Large family room. Bedrooms nice sizes. Unit
has a complete wrap around deck with ocean views. About 3 minute walk to Smathers beach. Really nice pool & 15 person hot tub. If you are
a beach person this unit is for you!! Only negative - not that close
to the down town area(5 minute car ride) - however unit …

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$600

6 BR / 7 BA / Sleeps 12

1 / 31

$600

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Seaport Treasure Estate ~ Monthly Rental

Key West house
6 BR / 7 BA / Sleeps 12 | Quick view

Details

While you won’t need a treasure map to find this exclusive resort-style estate, you’ll know you’ve discovered a rare island gem from the moment you walk through the private gates. Hidden by white picket fences and mature tropical landscaping, this spacious Seaport Treasure Estate is cleverly …
  • Housekeeping Optional
  • Grill
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$198

2 BR / 2 BA / Sleeps 6

1 / 22

$198

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DOMINICAN SUITE #110 - 2/2 Condo w/ Pool & Hot Tub - Near Smathers Beach

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

Details

Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9am - 6pm daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped …
  • 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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$198

2 BR / 2 BA / Sleeps 6

1 / 22

$198

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SAINT LUCIA SUITE #201 - 2/2 Condo w/ Pool & Hot Tub - Near Smathers Beach

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

Details

Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9am - 6pm daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped …
  • 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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$110

1 BR / 1 BA / Sleeps 4

1 / 4

$110

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Key West Cottage

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

Details

Key West Cottage located in Mid-town away from the maddening crowd when you want to be and close enough to join in when you're ready. Our cottage is surrounded by lush vegetation including: coconuts trees, mango trees, tamarind trees, banana plants, guava plants, Spanish lime trees and many more. In late summer …
  • A/C or climate control
  • Central heating
  • Linens Provided
  • Towels Provided

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$368

2 BR / 3 BA / Sleeps 6

1 / 38

$368

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"SWEET CAROLINE"

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

Details

Part of Banana's Foster Guest House This spacious 2 bedroom apartment takes up the first floor of this historic home. From the off street parking and shared courtyard entrance off Simonton opening into the kitchen to the private front entrance with sweeping front porch over Caroline Street- this rental has a lot to…
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Patio
  • Grill
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$225

2 BR / 2 BA / Sleeps 6

4 Reviews

$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

Details

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.

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$133

2 BR / 5 BA / Sleeps 4

1 / 14

$133

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Buoy's Backyard

Key West house
2 BR / 5 BA / Sleeps 4 | Quick view

Details

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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$400

2 BR / 2 BA / Sleeps 6

18 Reviews

$400

Inquire

The Meadows House

Key West house
2 BR / 2 BA / Sleeps 6 | Quick view
Excellent18 Reviews

Details

Reviews

(18)

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

(18)

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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$250

2 BR / 2 BA / Sleeps 6

35 Reviews

$250

Inquire

Duval Square

Key West house
2 BR / 2 BA / Sleeps 6 | Quick view
Excellent35 Reviews

Details

Reviews

(35)

The rooftop community of Duval Square is a prime perch from which to launch the best tropical vacation ever. The townhomes cluster on the second story above their namesake square. Winding pathways bordered by swaying palm and colorful plantings arranged in terracotta pots define the layout. Best of all, the small …
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Suitable for the elderly - ask

Details

Reviews

(35)

Barbecue

Left on Aug 14, 2008 for a stay in February 2008

The vacation week was good, except for the use of the barbecue. When we had stayed there before we had used the barbecue every other night (and gone out for dinner the other nights). We have a 6 yr. old and the deal we made with him was the above (as you know 6 yr. olds couldn't care less about eating out) and prefer barbecues and staying in. (ours does anyway). This February we were told that we…

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$700

4 BR / 4 BA / Sleeps 8

2 Reviews

$700

Inquire

Hermitage South

Key West house
4 BR / 4 BA / Sleeps 8 | Quick view
Excellent2 Reviews

Details

Reviews

(2)

The name Hermitage invokes the sense of secluded residence or private retreat that aptly describes this inspiring four-bedroom, four-bath home in the heart of Old Town Key West. You'll know the minute you walk through the front door that an artist with considerable flair has decorated Hermitage South to be a one-of-a-…
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for the elderly - ask

Details

Reviews

(2)

Family Vacation in Key West

Left on Aug 11, 2012 for a stay in July 2012

The staff at Historic Hideaways was absolutely wonderful in assisting with the long distance scheduling of this vacation. In addition they were very responsive to any question related to the property both before arrival and during our stay.

The home was exactly as described...Clean...and stocked with all the items needed for a home away from home vacation rental. This home was close to …

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$250

1 BR / 1 BA / Sleeps 2

70 Reviews

$250

Inquire

Rose Cottage

Key West house
1 BR / 1 BA / Sleeps 2 | Quick view
Excellent70 Reviews

Details

Reviews

(70)

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

(70)

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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$286

3 BR / 2 BA / Sleeps 6

1 / 9

$286

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Whitehead Suite B

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

Details

Downtown Key West, one block from Southernmost Point, one block from Hemingway House, walking distance to all mojor tourist attractions, restaurants, galleries, beaches. Three bedroom, two bath totally renovated, on site parking, rear patio. Central Air, granite counters, stainless appliances. Great family unit, one …
  • Wireless Internet
  • A/C or climate control
  • Central heating
  • Parking
  • Grill

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$188

1 BR / 1 BA / Sleeps 4

4 Reviews

$188

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HIDEAWAY @ TROPICAL VILLAGE - Cozy Condo For 2 w/ Shared Pool

Key West cottage
1 BR / 1 BA / Sleeps 4 | Quick view
Excellent4 Reviews

Details

Reviews

(4)

Part of TROPICAL VILLAGE Tropical Hideaway - Lush gardens surround this lovingly restored two-story vacation house. This downstairs rental cottage has one bedroom with full bath and features a living room with queen sleeper-sofa, cable TV, DVD, stereo with CD player, and wireless internet. The bedroom has a queen …
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(4)

Great stay!!!

Left on Oct 08, 2014 for a stay in October 2014

Everything was great! The location was perfect - and the private hot tub was the best! Only down side (which wasn't a big deal) was there were ants on the kitchen counter!

Very nice rental!!!!

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$400

5 BR / 4 BA / Sleeps 12

1 / 22

$400

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Bella Grand Premier ~ Monthly Rental

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

Details

Classic romantic 1800’s Key West architecture has inspired a superbly executed renovation of this extraordinary historic Victorian estate. Displaying a perfected cosmopolitan flair, the owner / designer has artfully intertwined a look-back into architectural history with a sophisticated contemporary Caribbean …
  • Shared outdoor pool (unheated)
  • Housekeeping Optional
  • A/C or climate control
  • Porch
  • Garden
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$215

1 BR / 1 BA / Sleeps 4

1 / 13

$215

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OLD TOWN KEY WEST - Historic & Charming - Cigar

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

Details

RENTAL RATES ARE NEGOTIABLE...Please contact us for current pricing and availability (we do not maintain calendars) In the event you, or any of your family, your guests, or your friends want to use the house at any time during the rental term, the rental rate would be the same. We do request that all guests, family …
  • Hot Tub/Jacuzzi
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$310

2 BR / 1 BA / Sleeps 5

1 Reviews

$310

Inquire

Harry in the Truman Suites - Luxury 2 bedroom 1 bath with full kitchen - sleeps up to 5

Key West house
2 BR / 1 BA / Sleeps 5 | Quick view
Excellent1 Reviews

Details

Reviews

(1)

THE TRUMAN SUITES - Four Weekly Vacation Rentals - 3 to 5 Night Minimum Stay Requirement - Lavishly appointed 1 and 2 bedroom suites located ONE HALF BLOCK FROM DUVAL STREET Each suite is furnished with a full kitchen, contemporary living room with comfortable furniture, new ultra comfortable mattresses with premium …
  • Wireless Internet
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Central heating
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

First class and close to everything!

Left on Dec 16, 2014 for a stay in October 2014

My wife and I stayed at this location during Fantasy Fest. It was our first time at Fantasy Fest but we are Key West regulars. The rooms are newly remodeled, clean and well thought out. The kitchen and TV area is larger and relaxing and the appliances are also all new. The location is perfect. We had a private parking place and the option to walk either direction on Duval St. depending on which …

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$300

3 BR / 2 BA / Sleeps 8

1 Reviews

$300

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Oceanside Key West's Best Luxury Penthouse Condo

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

Details

Reviews

(1)

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

Details

Reviews

(1)

Awesome View. Great Place.

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

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

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$198

2 BR / 2 BA / Sleeps 6

1 Reviews

$198

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CAT ISLAND SUITE #205 - 2/2 Condo w/ Pool & Hot Tub - Near Smathers Beach

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

Details

Reviews

(1)

Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9am - 6pm daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped …
  • 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

Details

Reviews

(1)

Aweful

Left on Nov 11, 2014 for a stay in October 2014

Avoid this place at all costs . It is horrible ….. I would rather have stayed in my car. The apartment was disgusting . Furniture looked like it was from the early 80's and was dirty.

The walls are mirrored and broken, fixed with tape. The smoke alarms are missing but the wires are hanging out of the walls. I would never stay there again. I do have to say the girl at the front desk was nice …

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$198

2 BR / 2 BA / Sleeps 6

1 / 24

$198

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COZUMEL SUITE #112 - 2/2 Condo w/ Pool & Hot Tub - Near Smathers Beach

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

Details

Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9am - 6pm daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped …
  • 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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$198

2 BR / 2 BA / Sleeps 6

1 / 23

$198

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HISPANIOLA SUITE #101- 2/2 Condo w/ Pool & Hot Tub - 1 Mile To Smathers Beach

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

Details

Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9am - 6pm daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped…
  • 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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$467

5 BR / 5 BA / Sleeps 14

1 / 40

$467

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"SHARK KEY CHATEAU" Incredible 3-Story Mansion w/ Private Beach, Pool, & Spa

Key West house
5 BR / 5 BA / Sleeps 14 | Quick view

Details

***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Shark Key Chateau is 'Grande' to say the least. With unspoiled views from every angle, to playful colors, and unrivaled decor and design, this home is a Chateau unlike any other. Shark Key Chateau is designed in true keys …
  • Private Beach
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
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