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62 Results   |  

Very Good 4.5/5 

15 Photos

Florida Keys / Key West

House / 2 Bedrooms / sleeps 4

Very Good 4.5/5 

30 Nights min stay

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Pricing unknown

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning
  • Pets welcome
30 DAY MINIMUM RENTAL This cute cottage just off of Frances Street is a great hideaway, still in Old Town, but a good central location to get to the Historic seaport or new town. The light & airy combined living/dining area with its soft color toned furnishings, hardwo  …see more

5 Photos

Florida Keys / Key West

B&B / 1 Bedroom / sleeps 2

3 Nights min stay

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from £98 / night

£682 / week

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Key info:

  • Beach / lakeside relaxation
  • Not suitable for children
  • Air conditioning
  • No pets allowed
 …see more

Good 3.5/5 

13 Photos

Florida Keys / Key West

House / 3 Bedrooms / sleeps 6

Good 3.5/5 

30 Nights min stay

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Pricing unknown

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning
  • No pets allowed
30 DAY MINIMUM RENTAL Walk the historic streets of Key West, live in Old Town in a quiet residential neighborhood. Just two blocks from Duval Street, it is a quick walk or bike ride to all of Key West's attractions, including it's close proximity to the Historic Seapor  …see more

Featured properties

Excellent 5/5 

18 Photos

Florida Keys / Key West

Yacht / 3 Bedrooms / sleeps 8

Excellent 5/5 

3 Nights min stay

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from £232 / night

£1623 - £3636 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
 …see more

24 Photos

Florida Keys / Key West

House / 3 Bedrooms / sleeps 8

30 Nights min stay

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from £206 / night

£1436 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Luxury house 10 minutes from Duval Street, pool, dock, pool bar, hot tub. Home owner association tennis courts and private beach on exclusive gated community island.  …see more

Very Good 4.5/5 

16 Photos

Florida Keys / Key West

Cottage / 1 Bedroom / sleeps 2

Very Good 4.5/5 

6 Nights min stay

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from £137 / night

£955 - £1773 / week

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning
  • No pets allowed
This charming one bedroom cottage is the perfect hideaway. The quiet compound is located just one block from Duval Street combining the best of both worlds for relaxing and taking advantage of all that Key West has to offer. Within 2 blocks you'll find Key West classic  …see more

Very Good 4.5/5 

34 Photos

Florida Keys / Key West

House / 4 Bedrooms / sleeps 8

Very Good 4.5/5 

6 Nights min stay

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from £533 / night

£3728 - £6455 / week

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning
  • No pets allowed
Tropical seclusion best describes this oasis in the Casa Marina District. Enter the splendor of this large estate through a private gate; stroll down brick pathways, meandering by the cottage until you reach the two story main home. The gardens are lush and abundant fea  …see more

Very Good 4.5/5 

16 Photos

Florida Keys / Key West

House / 3 Bedrooms / sleeps 6

Very Good 4.5/5 

6 Nights min stay

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from £286 / night

£2000 - £3410 / week

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning
  • No pets allowed
An Old town Key West home, located in the Historic District and just one half a block off Duval Street. Guests are within walking distance of restaurants, the Atlantic Ocean, Southernmost Point of Key West and our sunset piers. All lovingly restored and cared for, this  …see more

Very Good 4.5/5 

18 Photos

Florida Keys / Key West

House / 3 Bedrooms / sleeps 6

Very Good 4.5/5 

6 Nights min stay

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from £273 / night

£1910 - £3455 / week

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning
  • No pets allowed
This mid-town Key West home is newly renovated and beautifully decorated in jewel tones of the Mediterranean. It features three bedrooms and three baths. The open living/kitchen area is decorated with rich tones with tropical accents and soft fabrics. The dining room is  …see more

Very Good 4/5 

17 Photos

Florida Keys / Key West

Apartment / 2 Bedrooms / sleeps 6

Very Good 4/5 

6 Nights min stay

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from £176 / night

£1228 - £2364 / week

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning
  • No pets allowed
Unique oceanfront living only 65 feet from the Atlantic! The Key West Beach Club is a quiet, peaceful residential building that sits directly on the water. The breathtaking view can be seen as soon as you enter the unit. This spacious 2 bedroom unit features a larg  …see more

Very Good 4.5/5 

15 Photos

Florida Keys / Key West

Apartment / 2 Bedrooms / sleeps 6

Very Good 4.5/5 

6 Nights min stay

Add to shortlist

from £176 / night

£1228 - £2364 / week

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning
  • No pets allowed
Unique oceanfront living only 65 feet from the Atlantic! The Key West Beach Club is a quiet, peaceful residential building that sits directly on the water. The breathtaking view can be seen as soon as you enter the unit. This 2 bedroom, 2 bath unit features a huge  …see more

Very Good 4.5/5 

15 Photos

Florida Keys / Key West

Cottage / 1 Bedroom / sleeps 2

Very Good 4.5/5 

6 Nights min stay

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from £137 / night

£955 - £1773 / week

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning
  • No pets allowed
Tucked away in an inviting compound you'll find the perfect hideaway called Ann Street Cottage; a charming one bedroom cottage. The quiet compound is located just one block from Duval Street combining the best of both worlds for relaxing and taking advantage of all tha  …see more

Very Good 4.5/5 

14 Photos

Florida Keys / Key West

Cottage / sleeps 2

Very Good 4.5/5 

6 Nights min stay

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from £130 / night

£910 - £1637 / week

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning
  • No pets allowed
Perfect for two, this Bali-style studio cottage has it all: comfort, privacy and location. The quiet compound is located just one block from Duval Street combining the best of both worlds for relaxing and taking advantage of all that Key West has to offer. Within 2 bl  …see more

Very Good 4.5/5 

17 Photos

Florida Keys / Key West

Apartment / 2 Bedrooms / sleeps 5

Very Good 4.5/5 

6 Nights min stay

Add to shortlist

from £176 / night

£1228 - £2546 / week

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning
  • No pets allowed
Unique oceanfront living only 65 feet from the Atlantic! The Key West Beach Club is a quiet, peaceful residential building that sits directly on the water. The breathtaking view can be seen as soon as you enter the unit. This is one of the most elegant and colorful  …see more

Very Good 4/5 

17 Photos

Florida Keys / Key West

House / 2 Bedrooms / sleeps 4

Very Good 4/5 

6 Nights min stay

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from £189 / night

£1319 - £2500 / week

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning
  • No pets allowed
Thoughtfully restored, Havana Lane hearkens back to a time when cigar makers lived in the neighborhood, gathering on porch stoops to pass on the latest news. Near the notorious Key West Cemetery, this classic conch cottage embodies the essence of rustic charm while offe  …see more

Very Good 4.5/5 

11 Photos

from £195 / night

£1364 - £2319 / week

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Holiday home rental

Florida Keys / Key West

House / 2 Bedrooms / sleeps 4

Very Good 4.5/5 

6 Nights min stay

Add to shortlist

from £195 / night

£1364 - £2319 / week

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning
  • No pets allowed
This charming Key West style cottage is just a short walk to a selection of great restaurants, art galleries, and shopping. Catherine House is located only ½ block from the quieter end of Duval Street, and better yet, just three blocks to a beach (Duval & South Streets  …see more

Very Good 4/5 

9 Photos

Florida Keys / Key West

Apartment / 2 Bedrooms / sleeps 5

Very Good 4/5 

6 Nights min stay

Add to shortlist

from £176 / night

£1228 - £2364 / week

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning
  • No pets allowed
Unique oceanfront living only 65 feet from the Atlantic! The Key West Beach Club is a quiet, peaceful residential building that sits directly on the water. The breathtaking view can be seen as soon as you enter the unit. This comfortable 2 bedroom unit features a h  …see more

Very Good 4.5/5 

8 Photos

Florida Keys / Key West

Log cabin / 1 Bedroom / sleeps 4

Very Good 4.5/5 

6 Nights min stay

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from £130 / night

£910 - £1682 / week

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning
  • No pets allowed
Located just a step away from Old Town area surrounded by coconut palms and blooming bougainvilleas this charming one bedroom bungalow is a true island hideaway .The bungalow features an one level open space living/dining area, full kitchen and a spacious bedroom with a  …see more

Excellent 5/5 

23 Photos

Florida Keys / Key West

House / 4 Bedrooms / sleeps 8

Excellent 5/5 

6 Nights min stay

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from £468 / night

£3273 - £5455 / week

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning
  • No pets allowed
On a lovely tree-lined residential street in the heart of the historic Old Town district, this quiet, historic compound offers three separate vacation suites sharing a lush, large, sunny pool or combines for a wonderful four bedroom retreat. Downstairs enjoys a large, o  …see more

Very Good 4/5 

18 Photos

Florida Keys / Key West

House / 4 Bedrooms / sleeps 8

Very Good 4/5 

6 Nights min stay

Add to shortlist

from £306 / night

£2137 - £3864 / week

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning
  • No pets allowed
Great location, just half a block off Duval Street, walking distance to restaurants, the Atlantic beaches and the Southernmost Point. Casually decorated in soft pine and white, wicker furnishings and sofa sleeper in living room, this four bedroom, three and a half bath  …see more

Very Good 4/5 

12 Photos

Florida Keys / Key West

Apartment / 2 Bedrooms / sleeps 6

Very Good 4/5 

6 Nights min stay

Add to shortlist

from £176 / night

£1228 - £2364 / week

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning
  • No pets allowed
Unique oceanfront living only 65 feet from the Atlantic! The Key West Beach Club is a quiet, peaceful residential building that sits directly on the water. The breathtaking view can be seen as soon as you enter the unit. The huge oceanfront balcony can be accessed  …see more

Very Good 4/5 

19 Photos

from £221 / night

£1546 - £2910 / week

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Holiday home rental

Florida Keys / Key West

House / 3 Bedrooms / sleeps 6

Very Good 4/5 

6 Nights min stay

Add to shortlist

from £221 / night

£1546 - £2910 / week

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning
  • No pets allowed
Whitehead House is a unique two-story single family attached home nestled beside the Audubon House in Old Town Key West. Hidden behind the most photographed "prohibition fence" in Key West, this three bedroom, two bathroom home includes a large sunny pool and patio as w  …see more

Very Good 4.5/5 

20 Photos

Florida Keys / Key West

Apartment / 2 Bedrooms / sleeps 6

Very Good 4.5/5 

6 Nights min stay

Add to shortlist

from £156 / night

£1091 - £2000 / week

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning
  • No pets allowed
Enjoy the resort-style amenities of 1800 Atlantic Condominiums while relaxing in a residential setting amongst neighbors. 1800 Atlantic sits on 400 feet of oceanfront property. An expansive pool and spa sits oceanside surrounded by a lushly landscaped garden of native K  …see more

Excellent 5/5 

24 Photos

from £585 / night

£4091 - £12728 / week

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Holiday home rental

Florida Keys / Key West

House / 5 Bedrooms / sleeps 12

Excellent 5/5 

5 Nights min stay

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from £585 / night

£4091 - £12728 / week

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning
  • No pets allowed
Luxury on Duval Street in historic Key West? Luxury is not what most people visiting Key West associate with Duval Street until you look at Dreaming On Duval! There are very few private homes on Duval, let alone a single family vacation rental that is steps away from e  …see more

Very Good 4/5 

13 Photos

Florida Keys / Key West

House / 2 Bedrooms / sleeps 4

Very Good 4/5 

6 Nights min stay

Add to shortlist

from £169 / night

£1182 - £2000 / week

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning
  • No pets allowed
The best of Key West, in the middle of Historic Old Town and a half block from Duval Street and the gates to Bahama Village, a perfect location for visitors to our Island. Guests can stroll to Mallory Square, Fort Zachary Beach or the sunset piers which are all within e  …see more

 

13 Photos

Florida Keys / Key West

Cottage / 2 Bedrooms / sleeps 4

 

6 Nights min stay

Add to shortlist

from £163 / night

£1137 - £2000 / week

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning
  • No pets allowed
This property has it all! The styling of the original shot gun homes of Key West restored with a beautiful natural cypress exterior combines with the clean lines of a contemporary home. Each Twin opens to it's own semi-private deck and lounge area with steps into a larg  …see more

12 Photos

Florida Keys / Key West

House / 3 Bedrooms / sleeps 6

6 Nights min stay

Add to shortlist

from £345 / night

£2410 - £4091 / week

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning
  • No pets allowed
Tucked away near the upper end of Duval Street you'll find this stylish, newly renovated three bedroom, three bath home. Thoughtful details are luxuriously appointed to suit the vacation guest looking for privacy and high design. Walk up the brick drive and enter the  …see more

28 Photos

Florida Keys / Key West

House / 4 Bedrooms / sleeps 8

6 Nights min stay

Add to shortlist

from £293 / night

£2046 - £3637 / week

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning
  • No pets allowed
This property has it all! The styling of the original shot gun homes of Key West restored with a beautiful natural cypress exterior combines with the clean lines of a contemporary home. Each Twin opens to it's own semi-private deck and lounge area with steps into a larg  …see more

9 Photos

Florida Keys / Key West

Cottage / 2 Bedrooms / sleeps 4

6 Nights min stay

Add to shortlist

from £163 / night

£1137 - £2000 / week

View

Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning
  • No pets allowed
This property has it all! The styling of the original shot gun homes of Key West restored with a beautiful natural cypress exterior combines with the clean lines of a contemporary home. Each Twin opens to it's own semi-private deck and lounge area with steps into a larg  …see more

21 Photos

Florida Keys / Key West

House / 1 Bedroom / sleeps 2

6 Nights min stay

Add to shortlist

from £169 / night

£1182 - £1910 / week

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning
  • No pets allowed
Tucked away in an inviting compound you'll find a blissful retreat called Namaste; a tranquil and relaxing one bedroom cottage. The quiet compound is located just one block from Duval Street combining the best of both worlds for relaxing and taking advantage of all th  …see more

18 Photos

Florida Keys / Key West

House / 3 Bedrooms / sleeps 6

6 Nights min stay

Add to shortlist

from £332 / night

£2319 - £3864 / week

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning
  • No pets allowed
Location! Style! Elegance! This beautiful home is the fabulous combination of everything a great vacation property should be. One half block to Duval Street in the historic district, the location can't be beat. The home's history is rich; neighboring the historic Gato C  …see more

Excellent 5/5 

10 Photos

Florida Keys / Key West

House / 1 Bedroom / sleeps 2

Excellent 5/5 

30 Nights min stay

Add to shortlist

Pricing unknown

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning
  • No pets allowed
30 DAY MINIMUM RENTAL The meadows of Key West is a lovely, quiet and historic neighborhood located just behind Old Town Key West and known for it's tranquil tree lined streets. Centrally located on the island, yet far enough away from the hustle bustle of Duval, this i  …see more

Excellent 5/5 

17 Photos

Florida Keys / Key West

House / 2 Bedrooms / sleeps 4

Excellent 5/5 

30 Nights min stay

Add to shortlist

Pricing unknown

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning
  • No pets allowed
30 DAY MINIMUM RENTAL OLIVIA COTTAGE Recently featured in Coastal Living's "Guestbook" column, this charming Old Town house has recently been completely and tastefully renovated by its owners. Located just across the street from Key West's historic city cemetery, truly  …see more

 

54 Photos

Florida Keys / Key West

Cottage / 1 Bedroom / sleeps 4

 

30 Nights min stay

Add to shortlist

Pricing unknown

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Car not necessary
  • Air conditioning
  • Pets welcome
 …see more

Excellent 5/5 

17 Photos

Florida Keys / Key West

Apartment / 2 Bedrooms / sleeps 5

Excellent 5/5 

2 Nights min stay

Add to shortlist

from £141 / night

£983 - £2254 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Not suitable for children
  • Car not necessary
  • Air conditioning
  • No pets allowed
 …see more

8 Photos

Florida Keys / Key West

Condo / 1 Bedroom / sleeps 2

30 Nights min stay

Add to shortlist

Pricing unknown

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Key info:

  • Swimming pool
  • Not suitable for children
  • Air conditioning
  • No pets allowed
  • Private garden
 …see more

17 Photos

Florida Keys / Key West

Condo / 2 Bedrooms / sleeps 6

7 Nights min stay

Add to shortlist

from £229 / night

£1603 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Pets welcome
 …see more

Very Good 4.5/5 

14 Photos

Florida Keys / Key West

Apartment / 3 Bedrooms / sleeps 8

Very Good 4.5/5 

2 Nights min stay

Add to shortlist

from £161 / night

£1122 - £2599 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Not suitable for children
  • Car not necessary
  • Air conditioning
  • No pets allowed
 …see more

Excellent 5/5 

14 Photos

Florida Keys / Key West

Apartment / 2 Bedrooms / sleeps 6

Excellent 5/5 

2 Nights min stay

Add to shortlist

from £134 / night

£932 - £2150 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Not suitable for children
  • Car not necessary
  • Air conditioning
  • No pets allowed
 …see more

Very Good 4.5/5 

10 Photos

Florida Keys / Key West

Apartment / 2 Bedrooms / sleeps 5

Very Good 4.5/5 

2 Nights min stay

Add to shortlist

from £110 / night

£770 - £1616 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Air conditioning
  • No pets allowed
 …see more

7 Photos

Florida Keys / Key West

Apartment / 2 Bedrooms / sleeps 4

2 Nights min stay

Add to shortlist

from £115 / night

£802 - £2020 / week

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Key info:

  • Nearest beach 2 km
  • Swimming pool
  • Not suitable for children
  • Car advised
  • Air conditioning
  • No pets allowed
 …see more

9 Photos

Florida Keys / Key West

Yacht / 3 Bedrooms / sleeps 6

1 night min stay

Add to shortlist

from £415 / night

£2904 - £6420 / week

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Key info:

  • Not suitable for children
  • Air conditioning
  • No pets allowed
 …see more

10 Photos

Florida Keys / Key West

Yacht / 1 Bedroom / sleeps 2

1 night min stay

Add to shortlist

from £111 / night

£775 - £2065 / week

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Key info:

  • Not suitable for children
  • Air conditioning
  • No pets allowed
 …see more

Excellent 5/5 

16 Photos

Florida Keys / Key West

Apartment / 2 Bedrooms / sleeps 6

Excellent 5/5 

1 night min stay

Add to shortlist

from £154 / night

£1073 - £2480 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Car not necessary
  • Air conditioning
  • No pets allowed
 …see more

15 Photos

Florida Keys / Key West

Apartment / 1 Bedroom / sleeps 4

30 Nights min stay

Add to shortlist

Pricing unknown

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Key info:

  • Beach / lakeside relaxation
  • Ask owner if suitable for children
  • Car not necessary
  • Air conditioning
  • No pets allowed
 …see more

20 Photos

Florida Keys / Key West

House / 2 Bedrooms / sleeps 6

30 Nights min stay

Add to shortlist

from £86 / night

£601 - £904 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • Pets welcome
 …see more

10 Photos

Florida Keys / Key West

House / 3 Bedrooms / sleeps 6

7 Nights min stay

Add to shortlist

from £185 / night

£1291 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Air conditioning
  • Some pets are welcome - please contact the owner
******** Key West laws state that this property can only be rented out monthly******* This lovely home is in the Casa Marina District of Key West. It has a front porch, front balcony that the 2 smaller bedrooms have access to, a large patio by the heated private pool  …see more

Excellent 5/5 

8 Photos

Florida Keys / Key West

House / 3 Bedrooms / sleeps 8

Excellent 5/5 

30 Nights min stay

Add to shortlist

from £120 / night

£836 - £1130 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
 …see more

Excellent 5/5 

20 Photos

Florida Keys / Key West

Apartment / 1 Bedroom / sleeps 4

Excellent 5/5 

7 Nights min stay

Add to shortlist

from £96 / night

£671 - £1162 / week

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Key info:

  • Nearest beach 0 km
  • Swimming pool
  • Not suitable for children
  • Car not necessary
  • Air conditioning
  • No pets allowed
 …see more

18 Photos

Florida Keys / Key West

Condo / 3 Bedrooms / sleeps 9

30 Nights min stay

Add to shortlist

Pricing unknown

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
 …see more

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