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

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421 Vacation rentals

15

Yacht rental in Key West

Florida Keys / Key West

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • 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 $225 / night

$1,575 / week

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Responds fast!
avg. 25 minutes

from $225 / night

(23) Excellent 

28

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
  • 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

$2,875 - $3,750 / week

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Responds fast!
avg. 25 minutes

from $400 / night

(21) Excellent 

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

(23) 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

$1,000 - $2,520 / week

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from $159 / night

(39) 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 $375 / night

$2,362 - $2,645 / week

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Responds fast!
avg. 1 hour 27 minutes

from $375 / night

24

Apartment 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
  • Ask about pets
ATLANTIC PARADISE -- Imagine the ocean only several yards from your balcony, in a secure gated complex, with all the amenities you could ask for -- pool, Jacuzzi, tennis courts, parking garage with personal parking space. That's what you'll find at Atlantic Paradise. Tw …see more

from $230 / night

$1,610 / week

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from $230 / night

(26) Very Good 

24

Home rental in Key West with shared pool

Florida Keys / Key West

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
KEY WEST CASA – Beautiful and spacious Shipyard condo Key West, Key West Casa is one of only a few 3 bedroom 2 bath condos in the Shipyard complex. This great rental property is located in the prestigous Truman Annex community just 2 blocks to famous Duval Street and wa …see more

from $325 / night

$2,275 / week

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from $325 / night

8

Key West Vacation home rental

Florida Keys / Key West

2 6 30 nights min

  • 2 bedrooms
  • Sleeps 6
  • 30 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

(22) 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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Responds fast!
avg. 3 hours 12 minutes

from $279 / night

(43) 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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Responds fast!
avg. 3 hours 12 minutes

from $259 / night

(10) 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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Responds fast!
avg. 3 hours 24 minutes

from $299 / 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 - $2,000 / week

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from $215 / night

(1) Excellent 

48

Apartment 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
  • Ask about children
  • 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 $455 / night

$2,866 - $3,850 / week

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Responds fast!
avg. 3 hours 46 minutes

from $455 / 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 $115 / night

$805 / week

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from $115 / night

(52) Excellent 

28

Vacation apartment with shared pool in Key West

Florida Keys / Key West

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
SHIPYARD TREASURE: Contemporary Condo at Truman Annex - Walk to Beach/Duval Street Decorated in casual contemporary style, this second floor Shipyard condo is centrally located in the Truman Annex, within quick walking distance to all the sites and attractions of Old T …see more

from $235 / night

$1,645 / week

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from $235 / night

52

Vacation apartment in Key West

Florida Keys / Key West

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
1st floor garden-view unit, King in the master bedroom, 2 twins 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 Sports enthusiast …see more

from $400 / night

$2,520 - $2,700 / week

Book View

Responds fast!
avg. 3 hours 46 minutes

from $400 / night

(22) Very Good 

24

Home rental in Key West with shared pool

Florida Keys / Key West

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
LINGER LONGER -- Enjoy a carefree vacation in this beautifully decorated, 2 bedroom 1.5 bath home rental Florida Keys, located in the President's Walk of Truman Annex. Master bedroom with queen bed and guest bedroom with trundle that converts to 2 twins are on either s …see more

from $245 / night

$1,715 / week

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from $245 / night

54

Key West Vacation apartment accommodation

Florida Keys / Key West

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • 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 $455 / night

$2,866 - $3,850 / week

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Responds fast!
avg. 3 hours 46 minutes

from $455 / night

(32) Very Good 

24

Vacation apartment with shared pool in Key West

Florida Keys / Key West

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
FINN KEY: A beautiful 2 bedroom 1 bath downstairs condo located in The Shipyard section of Truman Annex. This pristine residential community is one of the most requested locations in the heart of Old Town Key West. A wonderful mix of a private community yet easy walking …see more

from $205 / night

$1,435 / week

Inquire View

from $205 / 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

$1,400 - $3,000 / week

Book View

Responds fast!
avg. 59 minutes

from $250 / night

(47) 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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Responds fast!
avg. 3 hours 12 minutes

from $329 / night

24

Vacation apartment with shared pool in Key West

Florida Keys / Key West

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
CONCH ADVENTURE - Nestled in a quiet corner of the Shipyard Condominiums in Truman Annex, this 2 bedroom 1 bath downstairs condo offers peace, quiet and convenience. Within steps of the road to Fort Zachary Taylor State Park in one direction and to the community pool i …see more

from $205 / night

$1,435 / week

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from $205 / night

(9) 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. 2 hours 45 minutes

from $279 / night

24

Vacation apartment with shared pool in Key West

Florida Keys / Key West

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Swimming pool
  • Child friendly
SOUTHARD GETAWAY: Imagine it. Arrive in Key West to a beach-like home in walking distance to all that Key West has to offer. Yes, that's Southard Getaway. Two queen bedrooms upstairs with full bath, open living space downstairs with quiet, shaded deck. Decorated in …see more

from $245 / night

$1,715 / week

Inquire View

from $245 / night

(30) Very Good 

24

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
  • Ask about pets
PAPAYA PLACE pops with color! This great 2 bedroom 2 bath waterfront Key West rental condo at 1800 Atlantic Condominiums offers you a wonderful relaxing garden view overlooking the nature preserve. Enjoy the peace and quiet of the tucked away balconies, far from the re …see more

from $230 / night

$1,610 / week

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from $230 / night

(10) Excellent 

23

Vacation home with shared pool in Key West

Florida Keys / Key West

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
ISLAND WIND : Welcome to a tropical sun drenched oasis in the heart of Old Town Key West. This charming 2 bedroom 2 bath Bahamian style townhome, with tin roof and white spindled decks reminiscent of old Key West, is located in award winning Windward Park, a gated and …see more

from $275 / night

$1,925 / week

Inquire View

from $275 / night

(26) Very Good 

24

Vacation apartment in Key West

Florida Keys / Key West

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
KEY WEST CHARMING at the Shipyard Condominiums condo rental in Key West. This downstairs 2 bedroom 1 bath home has been lovingly cared for by the owners. They actually use the property themselves each spring so they know what will make their guests stay more comfortabl …see more

from $205 / night

$1,435 / week

Inquire View

from $205 / night

(30) 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

Book View

Responds fast!
avg. 3 hours 12 minutes

from $249 / night

(6) Very Good 

24

Apartment 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
  • Ask about pets
KEY WEST CROWN JEWEL -- We know that you will enjoy staying in our vacation rental condo Key West - our little bit of Paradise. This is a 2-bedroom, 2-bath, penthouse condominium with 1350 square feet of living space and vaulted ceilings. Enjoy absolutely breathtaking …see more

from $375 / night

$2,625 / week

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from $375 / night

(1) Very Good 

43

Vacation apartment in Key West

Florida Keys / Key West

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • 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 $455 / night

$2,866 - $3,850 / week

Book View

Responds fast!
avg. 3 hours 46 minutes

from $455 / night

(11) Very Good 

24

Apartment rental in Key West with shared pool

Florida Keys / Key West

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
TRUMAN'S HIDEAWAY: It's hard to say which is more impressive, the view of Florida Bay from your private deck or living in front of Truman's Little White House. This lovely Truman Annex condo rental in the exclusive Harbour Place condominium complex offers all the comfo …see more

from $330 / night

$2,310 / week

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from $330 / night

(7) Excellent 

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

from $472 / night

$3,299 - $4,399 / week

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from $472 / night

(3) Excellent 

24

Vacation apartment with shared pool in Key West

Florida Keys / Key West

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
CITY CAY: Looking for a cozy, quiet spot for just the two of you with all the modern conveniences of home? This lovely Truman Annex Condo is the place! City Cay is our 1-bedroom 1-bath upper level condo that has been lovingly renovated and furnished in a sleek modern s …see more

from $190 / night

$1,330 / week

Inquire View

from $190 / night

(31) Very Good 

24

Key West Vacation home rental

Florida Keys / Key West

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
KEY WEST FOUND – A striking Key West FL home for rent, this 2 bedroom, 2.5 bath townhome is located in the historic brick Foundry building within the Truman Annex. This 3 story townhome is decorated in a whimsical Key West style with new living room furniture including …see more

from $280 / night

$1,960 / week

Inquire View

from $280 / night

(2) 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

(6) 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 $235 / night

$1,645 / week

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from $235 / night

(9) Excellent 

23

Apartment rental in Key West with shared pool

Florida Keys / Key West

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
SUNDOWN REFUGE: Balmy breezes, brilliant sunshine and magnificent sunsets await you at Sundown Refuge, located in the exclusive Harbour Place condominium complex in Truman Annex. You'll spend most of your time overlooking Florida Bay in one direction and Truman's Little …see more

from $330 / night

$2,310 / week

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from $330 / night

(4) Excellent 

24

Vacation home with shared pool in Key West

Florida Keys / Key West

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Coral Casita - Weekly Vacation Rental Completely re-designed, re-decorated and ready for your island adventures! When Key West is calling your name and nothing else will do, Coral Casita is the perfect mix of location, price and room for your large group to gather. A s …see more

from $245 / night

$1,715 / week

Inquire View

from $245 / 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 - $2,275 / week

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from $290 / night

(1) Good 

24

Vacation home with shared pool in Key West

Florida Keys / Key West

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
BAHAMIAN REED: 2 bedroom 1.5 bathroom townhome located in Truman Annex in Old Town Key West. Conveniently located near all the reasons you came to Key West: Fort Zachary Taylor State Park , Duval Street shops, galleries, bars and restaurants, and Sunset Celebration. G …see more

from $245 / night

$1,715 / week

Inquire View

from $245 / night