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

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434 Vacation rentals

(1) Excellent 

17

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 $200 / night

$1,400 / week

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Responds fast!
avg. 1 hour 54 minutes

from $200 / night

(27) 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 $385 / night

$2,875 - $3,925 / week

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Responds fast!
avg. 1 hour 54 minutes

from $385 / 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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Responds fast!
avg. 44 minutes

from $159 / 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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Responds fast!
avg. 2 hours 52 minutes

from $259 / 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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Responds fast!
avg. 2 hours 52 minutes

from $249 / night

(22) 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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Responds fast!
avg. 44 minutes

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 8 minutes

from $375 / night

(24) Very Good 

24

Vacation home with shared pool in Key West

Florida Keys / Key West

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
DUVAL PENTHOUSE -- A large luxury vacation rental in Key West located in downtown Key West. This property has it all, fabulous location, beautifully furnished and plenty of space to accommodate your friends and family. Duval Penthouse is designed after a chic urban f …see more

from $550 / night

$3,850 / week

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from $550 / night

(8) 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

(10) Excellent 

23

Vacation home with shared pool in Key West

Florida Keys / Key West

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
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 an …see more

from $225 / night

$1,575 / week

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from $225 / 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

(55) 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. 2 hours 55 minutes

from $329 / night

50

Key West Vacation apartment rental

Florida Keys / Key West

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • 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 $380 / night

$2,660 - $3,850 / week

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from $380 / 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
  • Air conditioning
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 $200 / night

$1,400 / week

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from $200 / 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 $108 / night

$756 / week

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from $108 / night

(3) Very Good 

24

Home accommodation in Key West with shared pool

Florida Keys / Key West

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
THE DOLPHIN HOUSE: Twice the comfort and twice the amenities - located in the exclusive Truman Annex. The Dolphin House Key West Vacation Rental is comprised of a bright and open main house and a lovely and bright guesthouse, with a pool and outdoor living space comf …see more

from $600 / night

$4,200 / week

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from $600 / night

(16) Very Good 

24

Vacation home with shared pool in Key West

Florida Keys / Key West

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
ALLURING PORCHES - A beautiful 2 bedroom 3 bath townhome with an additional den, is the tranquil escape you have been looking for. Wonderfully decorated with Key West charm and unique art work, stunning orchids surround this home and a beautiful open air feel brings the …see more

from $275 / night

$1,925 / week

Inquire View

from $275 / night

(26) 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. 2 hours 52 minutes

from $279 / night

(1) Excellent 

25

Vacation home in Key West

Florida Keys / Key West

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
EASY LIVIN' -- The name says it all! This lovely private home with pool is located in a secluded cul-de-sac in Truman Annex. Truman Annex is a gated community located in the historic Old Town neighborhood, in walking distance of anything you'll want to do during you …see more

from $500 / night

$3,500 / week

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from $500 / night

24

Vacation apartment with shared pool in Key West

Florida Keys / Key West

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
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 $160 / night

$1,120 / week

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from $160 / night

(1) Very Good 

24

Vacation apartment rental

Florida Keys / Key West

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
A BAREFOOT RETREAT: Step into this fantastic condo and the first thing you'll want to do is take off your shoes; feels just like home. Located on the main entry to Truman Annex, an exclusive gated community in historic Old Town, with all that Key West has to offer in ea …see more

from $170 / night

$1,190 / week

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from $170 / night

(4) Excellent 

24

Vacation home with shared pool in Key West

Florida Keys / Key West

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
CASA GRANDE: You hear all the time about grand homes tucked away in little private corners of Key West; this is one of them. Located on a quaint lane just steps from Duval Street with room to park 2 vehicles off-street -- a bonus in Old Town where parking is worth its w …see more

from $700 / night

$4,900 / week

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from $700 / night

(23) Very Good 

24

Vacation home 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
A PLACE IN PARADISE - You will experience true Key West living when you stay in this delightful 2 bedroom 2.5 bath Conch-Style townhome in Truman Annex. One of the most desirable locations for vacationers, you will spend your vacation in a quiet gated community surround …see more

from $225 / night

$1,575 / week

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from $225 / night

(2) Excellent 

25

Vacation home in Key West

Florida Keys / Key West

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 1 mi
  • Swimming pool
  • Child friendly
Beautiful Keywest home blocks from Higgs Beach, playgrounds, restaurants, and famous Duval street. This rental includes use of 2 beach cruisers. Private Pool and front yard. Tropical Oasis. Includes washer and dryer. This is a beautiful Key West home in old town. All am …see more

from $315 / night

$2,200 - $3,000 / week

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Responds fast!
avg. 31 minutes

from $315 / night

(35) Very Good 

24

Vacation home with shared pool in Key West

Florida Keys / Key West

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
LEEWARD ISLE KEY WEST RETREAT -- Dwell in the possibility! From the moment you park in the private parking lot for this Key West vacation condo you know you are someplace special. A small gated and secured compound with only 13 properties, this townhome community is qui …see more

from $225 / night

$1,575 / week

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from $225 / night

(52) Excellent 

28

Vacation apartment with shared pool in Key West

Florida Keys / Key West

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
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 …see more

from $210 / night

$1,470 / week

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from $210 / night

(29) Very Good 

24

Vacation cottage with shared pool in Key West

Florida Keys / Key West

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
TRANQUILITY - The epitome of life in Key West, this charming cottage is full of color and creativity, lovingly restored with no detail overlooked for a Key West vacation rental Florida. Fabulous artwork, fun collectibles, beautiful stained glass all give this cottage …see more

from $175 / night

$1,225 / week

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from $175 / 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
  • Ask about children
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 $500 / night

$2,900 / week

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from $500 / 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

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Responds fast!
avg. 1 hour 7 minutes

from $250 / night

(1) Excellent 

24

Home rental in Key West with shared pool

Florida Keys / Key West

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Breezy Bungalow - Weekly Rental When a name says it all you know you have made the perfect choice for your Key West island escape. Bright and colorful with plenty of windows, balconies and French doors open to allow sunshine and seaside breezes to flow openly into Bree …see more

from $225 / night

$1,575 / week

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from $225 / night

(1) Excellent 

24

Vacation home with swimming pool in Key West

Florida Keys / Key West

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
PRESIDENT'S WALK: It wasn't that long ago that President Truman took casual walks in this same location; now it's your turn. President's Walk exudes luxury and elegance with lots of upgrades and plush furnishings with your every comfort in mind. Situated directly in …see more

from $180 / night

$1,260 / week

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from $180 / night

(11) Very Good 

24

Apartment rental in Key West with shared pool

Florida Keys / Key West

2 5 Min stay varies

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

from $275 / night

$1,925 / week

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from $275 / night

(22) Very Good 

24

Home rental in Key West with shared pool

Florida Keys / Key West

2 5 Min stay varies

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

from $195 / night

$1,365 / week

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from $195 / night

(27) Very Good 

24

Vacation home with shared pool in Key West

Florida Keys / Key West

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
ARTIST GARDEN -- A bright and breezy 2 bedroom 2.5 bath private Key West house rental located in the prestigious Admiral's Lane neighborhood of the Truman Annex. This property is in the ideal location, walking distance to all Old Town Key West has to offer along with th …see more

from $275 / night

$1,925 / week

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from $275 / night

24

Key West Vacation home rental

Florida Keys / Key West

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
CAPTAINS WHEEL: Take control of your vacation, be the master of your fate. Captains Wheel will not disappoint. Situated on the corner of Southard and Emma Streets in Truman Annex, a most prestigious gated community in the heart of historic Old Town. 2 bedrooms, 2.5 b …see more

from $210 / night

$1,470 / week

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from $210 / night

(25) Very Good 

24

Vacation apartment rental

Florida Keys / Key West

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
LAVENDER JUNGLE - Beautiful 2 bedroom 1 bath downstairs Shipyard condo for rent Key West located in Truman Annex, this home has a renovated kitchen and upgraded bathroom. For those who don't want to climb stairs, this property is on the first floor and has a large br …see more

from $160 / night

$1,120 / week

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from $160 / night

(36) Very Good 

23

Vacation home with shared pool in Key West

Florida Keys / Key West

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
CONCH WIND - Stop searching, Conch Wind is the rental home in Key West you have been hunting for! This two story Conch Style townhome located in Old Town Key West is nestled in a quiet, secure compound. Plenty of space, beautifully furnished with all attention given …see more

from $225 / night

$1,575 / week

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from $225 / night

(3) Very Good 

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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from $225 / 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 $380 / night

$2,660 - $3,850 / week

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from $380 / night

(31) Very Good 

24

Key West Vacation home rental

Florida Keys / Key West

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
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 includi …see more

from $250 / night

$1,750 / week

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from $250 / night