50 Best Key West Vacation rentals on Holiday Lettings - House rentals

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508 Vacation rentals

(1) Excellent 

17

Yacht rental in Key West

Florida Keys / Key West

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary
This yacht is very spacious and bright with windows surrounding it making views of the ocean amazing. The marina and its grounds are meticulous and located in the middle of a turquoise paradise with amazing water clarity. Your stay will include free access to the mari …see more

from $240 / night

$1,680 / week

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Responds fast!
avg. 1 hour 23 minutes

from $240 / night

(29) Excellent 

31

Key West Vacation houseboat rental

Florida Keys / Key West

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary
Ocean view yacht with beautiful sunsets and sunrises. Underwater windows in the forward cabins makes this yacht unbelievable. Located in the finest most elegant first class marinas giving you full access to its restaurant and private pool during your stay. The marina i …see more

from $400 / night

$2,800 / week

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Responds fast!
avg. 1 hour 23 minutes

from $400 / night

(27) Very Good 

Certificate of Excellence

12

Vacation apartment in Key West

Florida Keys / Key West

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 2 mi
  • Swimming pool
  • Child friendly
Tropical 2 bedroom, 2 bath condo 1/2 mile from Smather's Beach in Key West. Fully appointed kitchen and living room. Balcony overlooking Salt Ponds and distant ocean view. Large heated pool on property, perfect for sunbathing. Jacuzzi and gym. Tennis court. Small b …see more

Certificate of Excellence

from $159 / night

$1,100 - $2,793 / week

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from $159 / night

(59) Very Good 

Certificate of Excellence

11

Apartment rental in Key West

Florida Keys / Key West

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Car not necessary
Just steps away from shops, restaurants, and the excitement of Duval Street, yet set on a quiet side street in a world of its own. With 3 bedrooms and 2 Baths, The Grand Bahama Suite has plenty of room for a large gathering or group of friends. Experience endless sun …see more

Certificate of Excellence

from $329 / night

$2,303 / week

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from $329 / night

(7) Excellent 

15

Apartment rental in Key West

Florida Keys / Key West

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Upper Duval is the best! A few steps away from the Southernmost pt & beaches,great restaurants,art galleries, Louies backyard,and Blue Heaven. A few more steps from Mallory sq, Sloppy Joes, Smokin tuna, the pier restaurants, entertainment day and night. Have the best of …see more

from $290 / night

$2,175 / week

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from $290 / night

(85) Very Good 

26

Apartment rental in Key West with swimming pool

Florida Keys / Key West

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This luxurious condo/hotel features a wonderful tropical interior design. It has 2 spacious bedrooms (one room with a king-size bed and a full bath and one queen-size bed with a full bath. The unit has a fully equipped kitchen that looks onto the living room with a q …see more

from $227 / night

$1,540 - $2,830 / week

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from $227 / night

(32) Excellent 

Certificate of Excellence

14

Vacation apartment in Key West

Florida Keys / Key West

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Car not necessary
Relax of the Island Style front porch and enjoy Key West at it's finest. Centrally located, less than a block from Duval - this Completely updated 2 Bedroom, 1 Bath will simply amaze you! High Ceilings, tall windows, full kitchen with separate dining room and plenty o …see more

Certificate of Excellence

from $249 / night

$1,743 / week

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from $249 / night

(7) Very Good 

18

Vacation apartment in Key West

Florida Keys / Key West

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
Mango Hideaway is ideally located in a quiet three-unit compound a half block off Duval St. in the heart of Old Town Key West. Our guests enjoy the best of both worlds, as the restaurants, world-class galleries, and vibrant nightlife of Duval St. are just a few steps aw …see more

from $225 / night

$1,575 / week

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from $225 / night

(47) Very Good 

Certificate of Excellence

17

Key West Vacation apartment rental

Florida Keys / Key West

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Car not necessary
Located in the heart of Old Town, this split 2 Bedroom plan is just blocks from everything Key West has to offer. The famous Southernmost Point, Hemingway House, Lighthouse, Beaches and more. Just 1/2 block from Duval Street. Completely updated for your comfort and c …see more

Certificate of Excellence

from $259 / night

$1,813 / week

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from $259 / night

(2) Very Good 

41

Vacation home rental

Florida Keys / Key West

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 0 mi
  • Swimming pool
  • Child friendly
Check out the new "Duval Loop" that ferries you around Old Town for free and is located at the corner of this homes block!!!!Map is included in pictures. Hemmingway House, Lighthouse, Butterfly World, Southern Most Point, Conch Tour Train, Beach, Galleries & Restaurant …see more

from $100 / night

$700 / week

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Responds fast!
avg. 1 hour 30 minutes

from $100 / night

(2) Excellent 

8

Key West Vacation apartment rental

Florida Keys / Key West

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary
Decorated in shade of sea foam and coral, this property is located in the Truman Annex and puts all of Key West's top attraction within easy walking distance. French doors open to a garden with hibiscus and cat palms framing a comfortable patio. Both bedrooms have que …see more

from $179 / night

$1,250 - $2,800 / week

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Responds fast!
avg. 1 hour 41 minutes

from $179 / night

(24) Very Good 

Certificate of Excellence

14

Vacation apartment in Key West

Florida Keys / Key West

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
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. Loc …see more

Certificate of Excellence

from $159 / night

$1,100 - $2,520 / week

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from $159 / night

13

Vacation home rental

Florida Keys / Key West

2 4 28 nights min

  • 2 bedrooms
  • Sleeps 4
  • 28 nights min
  • Nearest beach 2 mi
  • Child friendly
  • Air conditioning
Make this your Key West Vacation home! Cozy 2 bedroom, 1 bath home set on the back half of a residential lot with new kitchen, bath, and furniture. Privacy provided by the fenced outdoor area, with a shaded porch and furnished gazebo for relaxing. The location is 5 minu …see more

from $100 / night

$700 / week

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from $100 / night

(2) Very Good 

48

Apartment rental in Key West with shared pool

Florida Keys / Key West

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Atlantic Paradise Found C232 at 1800 Atlantic Condominiums is a beautifully appointed spacious condominium with a lovely view of the Atlantic Ocean Atlantic Paradise Found is one of the premium rental properties Condo's in the 1800 Atlantic Complex. Beautifully decor …see more

from $360 / night

$2,520 / week

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from $360 / night

32

Home rental in Key West with shared pool

Florida Keys / Key West

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
3 Bedrooms, 3 Full Bathrooms, Backs to Community Pool, Sleeps up to 6 This home was built in 2004. It has been well maintained and is ready for you to enjoy on your next vacation in Key West. You can stay in this 3 Bedroom home for less than the cost of one room in som …see more

from $325 / night

$2,275 / week

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from $325 / night

24

Boathouse rental in Key West

Florida Keys / Key West

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 6 mi
  • Swimming pool
  • Child friendly
Luxurious and spacious accommodations aboard this elegantly designed 45' Morgan Nelson Marek sailing vessel. Moored on first class dock space in front of the newly constructed Key West Perry Hotel, your stay will begin with welcome and cocktails as you board. Once you'v …see more

from $199 / night

$1,200 - $2,625 / week

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from $199 / night

18

Vacation home in Key West

Florida Keys / Key West

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Private garden
Come enjoy Island Living at it’s finest, Your own “Little Paradise”. This Two Bedroom Two bath home is nestled on a quiet one way street in The Historic Seaport District. This location is desirable for being walking distance to Duval Street and the proximity to 5 star r …see more

from $308 / night

$2,150 / week

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Responds fast!
avg. 3 hours 35 minutes

from $308 / night

6

Vacation apartment in Key West

Florida Keys / Key West

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
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- …see more

from $229 / night

$1,600 / week

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from $229 / night

(29) Excellent 

Certificate of Excellence

17

Vacation apartment in Key West

Florida Keys / Key West

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Car not necessary
  • Air conditioning
The Nassau Suite is one of the largest suites in The Bahama House. Featuring 2 King Bedrooms, 2 Bath. Quietly Tucked away in a world of it's own, yet literally only steps away from all that Key West has to offer. Whether your looking for a place to meditate or find an …see more

Certificate of Excellence

from $279 / night

$1,953 / week

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from $279 / night

54

Key West Vacation apartment accommodation

Florida Keys / Key West

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Penthouse property with vaulted ceilings at the famous 1800 Atlantic. Both bedrooms and the living room have access to your private balcony with great views of the property and Atlantic Ocean. The Owners are fishing enthusiasts as you will see when you relax in the comf …see more

from $360 / night

$2,520 / week

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from $360 / night

(39) Excellent 

39

Vacation apartment rental

Florida Keys / Key West

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool
This Luxury unit is 1375 sq ft of breath taking beachfront living space in this tropical complex. Great views from the 40 foot deck which encompasses the whole unit. Every room has a spectacular view of the tropical Nature Preserve and the Atlantic Ocean. The complex i …see more

from $375 / night

$2,362 - $2,583 / week

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Responds fast!
avg. 1 hour 12 minutes

from $375 / night

7

Apartment rental in Key West

Florida Keys / Key West

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
Unique and beautifully renewed apartment in the heart of Key West. Spacious bedroom with King Size bed and Walk-in Closet, large living room with pull-out sofa bed and kitchen. Take advantage of our unbeatable reopening price and enjoy! If we find that the house has be …see more

from $266 / night

$1,862 / week

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from $266 / night

13

Condo rental in Key West with shared pool

Florida Keys / Key West

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Located one block off Duval Street in central Old Town, the unit is on a historic estate and renovated with modern conveniences, hardwood floors, and plantation shutters, with plenty of ambient light. This second story unit has a large bathroom and a large deck off the …see more

from $190 / night

$1,225 / week

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Responds fast!
avg. 1 hour 40 minutes

from $190 / night

(4) Excellent 

22

Vacation condo in Key West

Florida Keys / Key West

2 6 5 nights min

  • 2 bedrooms
  • Sleeps 6
  • 5 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
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 …see more

from $225 / night

$1,400 - $3,000 / week

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Responds fast!
avg. 3 hours 59 minutes

from $225 / night

(2) Excellent 

30

Vacation home in Key West

Florida Keys / Key West

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Air conditioning
The Poinciana Place Vacation Rentals are located on a tiny lane in Old Town Key West. This two story duplex is one block to Duval Street and central to all that Key West has to offer. There are two one bedroom vacation rental units in this home. The second floor un …see more

from $257 / night

$1,565 - $2,373 / week

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from $257 / night

29

Key West Vacation home rental

Florida Keys / Key West

3 6 28 nights min

  • 3 bedrooms
  • Sleeps 6
  • 28 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Our beautiful, private home is located in a private, small subdivision with about 25 homes all on the open water, Gulf view. Its's a lovely home with 1 bedroom downstairs with a half bath and 2 large bedrooms upstairs with 2 full bathrooms. The master upstairs has a ba …see more

from $250 / night

$1,750 / week

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Responds fast!
avg. 3 hours 56 minutes

from $250 / night

(1) Very Good 

43

Vacation apartment in Key West

Florida Keys / Key West

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
The Grand Vista - 2 bedroom suite 2 Bedroom 2 bath suite, Totally renovated with flat screen plasma TV's in both bedrooms and the living room. All brand new furniture in Jan 2010, King bed in the Master bedroom, queen in the guest bedroom and a queen sleeper sofa in th …see more

from $360 / night

$2,520 / week

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from $360 / night

50

Key West Vacation apartment rental

Florida Keys / Key West

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This wonderful property has brand new living and bedroom furniture in 2016, King bed in the master bedroom, 2 twins in the 2nd bedroom and a memory foam luxury queen sleeper in the living room will comfortably accommodate your party. Watch the sunrise from your private …see more

from $420 / night

$3,675 / week

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from $420 / night

(11) Excellent 

17

Vacation apartment in Key West

Florida Keys / Key West

2 6 5 nights min

  • 2 bedrooms
  • Sleeps 6
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
The "SeaJay" at La Brisa is located in a gated community overlooking the Atlantic Ocean just steps away from Smathers Beach with it's pristine sand and palm trees. Directly across the street is Key West's longest sidewalk along the beautiful ocean for bike riding, jogg …see more

from $279 / night

$1,950 / week

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Responds fast!
avg. 3 hours 53 minutes

from $279 / night

(4) Excellent 

24

Vacation townhouse in Key West

Florida Keys / Key West

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
2 Bdrm, 1 Bath, Washer/dryer, Dishwasher, Great Porch View Of Southard St, Pool Multiple week and military discounts available. Great Fall rates! Queen bed in Master Bedroom, two single beds in second bedroom, fold out queen bed in couch, gated back patio with ga …see more

from $315 / night

$2,200 - $2,900 / week

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Responds fast!
avg. 3 hours 12 minutes

from $315 / night

50

Vacation apartment in Key West

Florida Keys / Key West

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
1st floor garden-view unit, King in the master bedroom, A double and a single in the guest bedroom and a queen sleeper sofa in the living room. This unit has high speed wireless and will accommodate up to 6 people. Just a short walk to the pool and Jacuzzi. For the Spo …see more

from $360 / night

$3,325 / week

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from $360 / night

14

Key West Vacation home rental

Florida Keys / Key West

2 6 30 nights min

  • 2 bedrooms
  • Sleeps 6
  • 30 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
YOUR PRIVATE GETAWAY IN KEY WEST, FLORIDA.  This beautifully historic 2 bedroom 2 bath home is conveniently located in Old Town Key West, FL. Just a short walk from everything you could dream of, for your island vacation. Just 5 blocks from the famous Duval Street. Tw …see more

from $335 / night

$2,345 / week

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from $335 / night

(11) Excellent 

14

Apartment rental in Key West

Florida Keys / Key West

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Beach/lakeside relaxation
  • Car not necessary
  • Air conditioning
Located in the heart of Duval St, this unique property offers a central location to the Key West landmarks and sights. Enjoy all Key West has to offer from a historic building with a private balcony overlooking Duval St. This property features a 1 bedroom with a king …see more

from $299 / night

$2,093 / week

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from $299 / night

(3) Very Good 

17

Key West Vacation apartment rental

Florida Keys / Key West

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
For those of you who want to stay as close to Key West as possible without paying those outrageous Key West prices, stay with us between mile marker 10 and 11 in this waterfront condominium. This small, yet efficient penthouse condominium, 672 sq. ft., stands alone as a …see more

from $165 / night

$1,155 / week

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from $165 / night

(8) Excellent 

Certificate of Excellence

23

Key West Vacation home rental

Florida Keys / Key West

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary
Key West Oasis is a private two bedroom/two bath rental house ideally located in Charming Old Town, Key West, Florida, close to Duval street, great restaurants, bars and the beach. This 1906 'cigar maker's cottage' has been newly renovated into a stylish Key West retrea …see more

Certificate of Excellence

from $472 / night

$3,299 - $4,399 / week

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from $472 / night

(1) Excellent 

46

Vacation apartment rental

Florida Keys / Key West

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This unit has a king in both bedrooms. 1800 Atlantic is directly on the Atlantic ocean in Key West, adjacent to Smathers Beach the City Beach with a variety of watersports activities available. The property itself features assigned secure parking spaces, 3 lighted ten …see more

from $300 / night

$2,100 / week

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from $300 / night

9

Vacation townhouse in Key West

Florida Keys / Key West

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
This 2 bedroom, fully furnished condominium is located in the Truman Annex, a gated community of private homes and condominiums. Freshly painted and upgraded with custom bedspreads, new key west style furniture, all flat screen televisions, comfortable outdoor furniture …see more

from $215 / night

$1,500 / week

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from $215 / night

6

Vacation condo in Key West

Florida Keys / Key West

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Garden Oasis is a first floor condo in the Shipyard Condos in Truman Annex. We are ideally located 2 blocks from the action (restaurants, shops, clubs) of Duval St., and very short walks to sunsets at Mallory Sq, and the beaches of Ft. Zachary Tayler Park. The Shipyard …see more

from $275 / night

$1,925 / week

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from $275 / night

44

Vacation yacht rental

Florida Keys / Key West

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 4 mi
  • Swimming pool
If you have had your fill of hotels and the street scenes of downtown Key West and you don't want to spend another minute on a boat loaded with people but do want to get out on the water, then S/V Tortuga may be the perfect solution for you. Tortuga Sailing Adventures …see more

from $700 / night

$4,900 / week

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from $700 / night

(4) Very Good 

24

Home rental in Key West with shared pool

Florida Keys / Key West

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
DUVAL ON THE SQUARE - Located at the Duval Square townhomes directly on Duval but above all the hubbub. This Key West house rental near Duval Street is built on the second and third story of the complex with the first floor being a wonderful collection of cafes and bist …see more

from $234 / night

$1,638 / week

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from $234 / night