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

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149 Vacation rentals

(7) Excellent 

21

Key West Vacation houseboat rental

Florida Keys / Key West

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
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 member only marinas. Guests have access to private pool, tiki bar, fine dining restaurant and fre …see more

from $405 / night

$2500 - $6650 / week

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from $405 / night

(1)  

15

Houseboat rental in Key West

Florida Keys / Key West

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Pet friendly
Rosie is at anchor in harbor just off the bustling downtown life of Key West. She has a very comfortable queen size V berth bed, a cozy saloon (living room) great for curling up, amazing sunset views, and in a very friendly neighborhood of boats! Rosie is a 33ft Pears …see more

from $169 / night

$999 - $1349 / week

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from $169 / night

4

Key West Vacation boathouse rental

Florida Keys / Key West

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Air conditioning
2 private bedrooms, plus pullout bed. Immaculate cabin interior. Approximately 100 yards off shore is where your adventure begins! Enjoy key west sunshine on your own private sundeck with comfortable upholstered seating & outdoor table for drinks/snacks. After you've wo …see more

from $225 / night

$1575 / week

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from $225 / night

(39) Very Good 

Certificate of Excellence

14

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

$2303 / week

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from $329 / night

(37) Excellent 

Certificate of Excellence

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

Certificate of Excellence

from $340 / night

$2143 - $3800 / week

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from $340 / night

(33) 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

$1813 / week

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from $259 / night

15

Vacation home rental

Florida Keys / Key West

2 6 30 nights min

  • 2 bedrooms
  • Sleeps 6
  • 30 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Hello prospective guests! Our great little spot is only a monthly rental but I am sure you will find our rate for a month is less expensive than most for a week. Please consider a longer stay on our island while saving some money by doing so. In a great location,nes …see more

from $94 / night

$654 / week

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from $94 / night

13

Key West Vacation condo rental

Florida Keys / Key West

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
Modern 2 bedroom/2 bath condo with nice size balcony overlooks the Atlantic Ocean. California king bed in Master Bedroom and twin beds in the guest bedroom that can be converted into a king bed. Living room sofa with queen sleeper. Nicely decorated with a Key West Flai …see more

from $299 / night

$1400 - $2500 / week

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from $299 / night

6

Vacation hotel apartment in Key West

Florida Keys / Key West

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
We are able to offer reservations in weekly increments with arrivals and departures Fridays, Saturdays, and Sundays only. Welcome to your own private sanctuary among the lush landscape of Key West - envision old-fashioned screen-enclosed porches, gardens bursting with …see more

from $475 / night

$3325 / week

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from $475 / night

(17) 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 and 2 Day-rooms with Futons. 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 p …see more

Certificate of Excellence

from $279 / night

$1953 / week

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from $279 / night

(28) 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

$1743 / week

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from $249 / night

(4) 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 $270 / night

$1875 / week

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from $270 / night

8

Key West Vacation home rental

Florida Keys / Key West

2 6 14 nights min

  • 2 bedrooms
  • Sleeps 6
  • 14 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly
This fully furnished turn-key two bedroom bungalow is the perfect spot to escape the winter weather in tropical Key West! Full kitchen, luxury shower, high ceilings and washer/dryer in unit! Also has a nice little fenced in outdoor space with a picnic table for enjoying …see more

from $135 / night

$945 / week

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from $135 / night

15

Vacation hotel apartment rental

Florida Keys / Key West

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
The Hyatt Windward Pointe is the most luxurious accommodation in Key West. This is one of a kind unit that is the best in the property with ocean and pool view and largest balcony on the third floor. One- king bedroom suite with ocean views, queen bedroom and sleep sofa …see more

from $429 / night

$2999 - $4890 / week

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from $429 / night

7

Key West Vacation hotel apartment rental

Florida Keys / Key West

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
We are able to offer reservations in weekly increments with arrivals and departures Fridays, Saturdays and Sundays only. Set along the Atlantic Ocean, Hyatt Windward Pointe Resort blends the laid-back Key West style with a modern, upscale resort ambiance. Here is a ret …see more

from $500 / night

$3500 / week

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from $500 / night

9

Vacation condo with shared pool 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
Hyatt Sunset Harbour Residence Club. *2016 Certificate of Excellence Winner TripAdvisor* **1 WEEK RENTAL 5/28/17 to 6/04/17**. Location, Location, Location. Private Balcony. 2 bedroom 2 bath. Full kitchen, dining table and living room includes sofa bed. Can accommod …see more

from $199 / night

$1393 / week

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from $199 / night

(3) Excellent 

22

Vacation condo in Key West

Florida Keys / Key West

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
This 2 bedroom, 2 bathroom unit offers all the convenience and comfort of your own home. It is spacious and fully equipped. Located just minutes from Smathers Beach, two miles from Higgs Beach. This condo is a fourth floor unit (there are two elevators in the buildin …see more

from $275 / night

$1700 - $2400 / week

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from $275 / night

(4) Very Good 

20

Vacation apartment in Key West

Florida Keys / Key West

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Nearest beach 3 mi
  • Swimming pool
  • Child friendly
Come down and take part in in Key West's many fishing tournaments! 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 gr …see more

from $240 / night

$1600 / week

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from $240 / night

(3) Very Good 

32

Key West Vacation townhouse rental

Florida Keys / Key West

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
Coral Hammock was built in 2004. Casa Paradiso is a spacious 3 bedroom, 3 bath home in a beautifully landscaped gated community. It features 2 king size beds and one queen.The kitchen is fully equipped with modern appliances, dishes and cooking utensils.There is an outd …see more

from $320 / night

$2240 / week

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from $320 / night

53

Vacation apartment in Key West

Florida Keys / Key West

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Beautiful 2 bedroom 2 bath unit, with a lovely view of the Atlantic Ocean. This unit is an extra large floor plan with a slighly large balcony. Access the Balcony from both bedrooms and the living room. There is a full size fully equipped eat in Kitchen and a Full size …see more

from $250 / night

$1750 / week

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from $250 / night

(8) Excellent 

14

Apartment rental in Key West

Florida Keys / Key West

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • 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 $168 / night

$2800 - $4850 / week

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from $168 / night

(4) Very Good 

99

Vacation cottage in Key West

Florida Keys / Key West

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Child friendly
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 …see more

from $428 / night

$2856 / week

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from $428 / night

(4) Excellent 

53

Vacation apartment with shared pool 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
Totally renovated top of the the line unit. King bed in the master bedroom, 2 twins in the guest bedroom and a queen sleeper sofa in the living room. Beautifully decorated by an interior designer. Custom bathrooms and modern kitchen with stainless appliances. Wireless I …see more

from $403 / night

$2588 - $2993 / week

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from $403 / night

(17) Very Good 

13

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

from $169 / night

$1000 - $2520 / week

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from $169 / night

(8) Very Good 

14

Vacation apartment in Key West

Florida Keys / Key West

3 6 30 nights min

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

from $400 / night

$2800 / week

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from $400 / night

(1) Excellent 

15

Vacation home in Key West

Florida Keys / Key West

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This beautiful home in Key West has recently been updated with new furnishings. It has over 1400 sf of living space. On the upper level there are two good sized bedrooms (one has a king size bed, the other has two twin size beds) each with their own bathroom. There …see more

from $250 / night

$1400 - $3000 / week

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from $250 / night

(1) 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 $325 / night

$2275 - $3900 / week

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from $325 / night

(1) Excellent 

40

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
1800 Atlantic Condominiums Unit C232 2 Bedroom. Ocean View. Unit C232 is one of the premium rental Condo's in the 1800 Atlantic Complex. Beautifully decorated with higher end furnishings. Top of the line full size fully equipped eat in Kitchen. Dining room area and spa …see more

from $420 / night

$2646 - $2993 / week

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from $420 / night

12

Vacation townhouse 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
The master bedroom has a queen sized bed with a feather mattress topper to experience a floating cloud effect. It has cable flat-screen TV, DVD/VCR, and a balcony where you can sit (take director's chairs from bedrooms) for morning coffee or evening cocktails. The custo …see more

from $358 / night

$2500 / week

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from $358 / night

44

Vacation apartment rental

Florida Keys / Key West

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
2 Bedroom Garden-View Condo at 1800 Atlantic Key West with king in the Master bedroom, queen in the guest bedroom and a queen sleeper sofa in the living room. Privately owned with upgrades, Flat screen TV's 1800 Atlantic is directly on the Atlantic ocean in Key West, …see more

from $360 / night

$2268 - $2520 / week

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from $360 / 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 $225 / night

$1575 / week

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from $225 / night

(2) Excellent 

22

Vacation condo in Key West

Florida Keys / Key West

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • 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

$1400 - $3000 / week

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from $225 / night

36

Vacation apartment with shared pool 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
Located overlooking the tropical courtyard and garden area. Nicely decorated two bedroom two bath unit. Newly renovated bathrooms. Master bathroom has a tub and walk in shower. There is a queen in the master bedroom, two twins in the guest bedroom and a queen sleeper so …see more

from $360 / night

$2268 - $2520 / week

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from $360 / night

(4) Excellent 

23

Key West Vacation home rental

Florida Keys / Key West

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Ask about children
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

from $486 / night

$3400 - $4500 / week

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from $486 / night

(1) Excellent 

24

Home rental in Key West

Florida Keys / Key West

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Private garden
The Space Fully renewed, beautiful colors and large spaces. The affordable luxury in downtown Key West. Two blocks from the Ocean, two minutes walk to watch the beautiful Key West Sunset. Guest Access You take over the full house, deck, balcony, large living-room, kitc …see more

from $680 / night

$4760 / week

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from $680 / night

43

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
Fabulous 2 bedroom island view condominium, fully equipped unit. Full kitchen and washer dryer. There is a king in the master bedroom, 2 twins in the guest bedroom and a queen sleeper sofa in the living room. Wireless Internet. The unit is 1357 sq feet. Both bedrooms an …see more

from $360 / night

$2268 - $2520 / week

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from $360 / night

43

Vacation apartment with shared pool in Key West

Florida Keys / Key West

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This is a unique unit with an amazing view of the Atlantic ocean. Your home away from home, all the conveniences you would need. Both bedrooms and the living room have sliding glass doors that open onto an extensive private balcony with the best view in Key West. You c …see more

from $340 / night

$2375 / week

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from $340 / night

44

Key West Vacation apartment rental

Florida Keys / Key West

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Beautiful 3 Bedroom Two and a half Bath ocean-front condominium at 1800 Atlantic. Enjoy the balmy breezes from your 60 foot private wrap around balcony with a fabulous view of the Atlantic ocean. This unit has a remodeled Kitchen and bathrooms also. Guest pays $200 clea …see more

from $550 / night

$3600 - $4086 / week

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from $550 / night

(12) Excellent 

14

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

from $159 / night

$1100 - $2793 / week

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from $159 / 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 $215 / night

$1500 / week

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from $215 / night

1