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Holiday Rentals with Pools in Key West

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 km
88 rentals in Key West.
Island Suite @ KW Vacation, holiday rental in Key West

Island Suite @ KW Vacation

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, All pools
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OLD TOWN, 2 Bedrm, Pool, Fully Equipped Kitchen, Wrap around private porch, W/D, holiday rental in Key West
OLD TOWN, 2 Bedrm, Pool, Fully Equipped Kitchen, Wrap around private porch, W/D, holiday rental in Key West
OLD TOWN, 2 Bedrm, Pool, Fully Equipped Kitchen, Wrap around private porch, W/D, holiday rental in Key West

OLD TOWN, 2 Bedrm, Pool, Fully Equipped Kitchen, Wrap around private porch, W/D

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, All pools
More info
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One-bedroom time share suite in the heart of Old Key West, holiday rental in Key West
One-bedroom time share suite in the heart of Old Key West, holiday rental in Key West
One-bedroom time share suite in the heart of Old Key West, holiday rental in Key West

One-bedroom time share suite in the heart of Old Key West

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, All pools
More info
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Sunshine suit (2/2 apartment), holiday rental in Key West
Sunshine suit (2/2 apartment), holiday rental in Key West
Sunshine suit (2/2 apartment), holiday rental in Key West

Sunshine suit (2/2 apartment)

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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The Oasis: Stylishly Updated 1BR Home Convenient to Duval St & Beaches, Shared P, holiday rental in Key West
The Oasis: Stylishly Updated 1BR Home Convenient to Duval St & Beaches, Shared P, holiday rental in Key West
The Oasis: Stylishly Updated 1BR Home Convenient to Duval St & Beaches, Shared P, holiday rental in Key West

The Oasis: Stylishly Updated 1BR Home Convenient to Duval St & Beaches, Shared P

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, All pools
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A Change in Latitudes - TRUMAN ANNEX, holiday rental in Key West
A Change in Latitudes - TRUMAN ANNEX, holiday rental in Key West
A Change in Latitudes - TRUMAN ANNEX, holiday rental in Key West

A Change in Latitudes - TRUMAN ANNEX

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, All pools
More info
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Key West, Private Beach, Fishing Pier, Old Town, Galleon Resort, holiday rental in Key West
Key West, Private Beach, Fishing Pier, Old Town, Galleon Resort, holiday rental in Key West
Key West, Private Beach, Fishing Pier, Old Town, Galleon Resort, holiday rental in Key West

Key West, Private Beach, Fishing Pier, Old Town, Galleon Resort

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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Sunrise Suite Key West 2 Bed Rooms 2 Full Baths, holiday rental in Key West
Sunrise Suite Key West 2 Bed Rooms 2 Full Baths, holiday rental in Key West
Sunrise Suite Key West 2 Bed Rooms 2 Full Baths, holiday rental in Key West

Sunrise Suite Key West 2 Bed Rooms 2 Full Baths

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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Private, heated pool.  Private yard., holiday rental in Key West
Private, heated pool.  Private yard., holiday rental in Key West
Private, heated pool.  Private yard., holiday rental in Key West

Private, heated pool. Private yard.

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, All pools
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Cozy Key West Hideaway with a Pool, Digital Workspace, and Privacy, holiday rental in Key West
Cozy Key West Hideaway with a Pool, Digital Workspace, and Privacy, holiday rental in Key West
Cozy Key West Hideaway with a Pool, Digital Workspace, and Privacy, holiday rental in Key West

Cozy Key West Hideaway with a Pool, Digital Workspace, and Privacy

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps, All pools
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Comfy Family Home in a Gorgeous Gated Community, holiday rental in Key West
Comfy Family Home in a Gorgeous Gated Community, holiday rental in Key West
Comfy Family Home in a Gorgeous Gated Community, holiday rental in Key West

Comfy Family Home in a Gorgeous Gated Community

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Tropical Old Town Bungalow: Charming 2nd Floor Unit, Private Spa/Shared Pool, Ne, holiday rental in Key West
Tropical Old Town Bungalow: Charming 2nd Floor Unit, Private Spa/Shared Pool, Ne, holiday rental in Key West
Tropical Old Town Bungalow: Charming 2nd Floor Unit, Private Spa/Shared Pool, Ne, holiday rental in Key West

Tropical Old Town Bungalow: Charming 2nd Floor Unit, Private Spa/Shared Pool, Ne

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, All pools
More info
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Cocktails & Dreams: Modern 2nd Floor Condo, Steps from Duval St, Seaport, Waterp, holiday rental in Key West
Cocktails & Dreams: Modern 2nd Floor Condo, Steps from Duval St, Seaport, Waterp, holiday rental in Key West
Cocktails & Dreams: Modern 2nd Floor Condo, Steps from Duval St, Seaport, Waterp, holiday rental in Key West

Cocktails & Dreams: Modern 2nd Floor Condo, Steps from Duval St, Seaport, Waterp

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, All pools
More info
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Lovely 2 bedroom, 2 bath condo at La Brisa., holiday rental in Key West
Lovely 2 bedroom, 2 bath condo at La Brisa., holiday rental in Key West
Lovely 2 bedroom, 2 bath condo at La Brisa., holiday rental in Key West

Lovely 2 bedroom, 2 bath condo at La Brisa.

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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Ambrosia - OLD TOWN/HISTORIC SEAPORT, large POOL, wrap around porch, washer/dry, holiday rental in Key West
Ambrosia - OLD TOWN/HISTORIC SEAPORT, large POOL, wrap around porch, washer/dry, holiday rental in Key West
Ambrosia - OLD TOWN/HISTORIC SEAPORT, large POOL, wrap around porch, washer/dry, holiday rental in Key West

Ambrosia - OLD TOWN/HISTORIC SEAPORT, large POOL, wrap around porch, washer/dry

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, All pools
More info
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White Ibis: Charming 2BR Key West Home, Pool, Ideal for Downtown & Beach Fun, Do, holiday rental in Key West
White Ibis: Charming 2BR Key West Home, Pool, Ideal for Downtown & Beach Fun, Do, holiday rental in Key West
White Ibis: Charming 2BR Key West Home, Pool, Ideal for Downtown & Beach Fun, Do, holiday rental in Key West

White Ibis: Charming 2BR Key West Home, Pool, Ideal for Downtown & Beach Fun, Do

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
More info
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Sunrise at Seaside Condo 2 Bedroom, holiday rental in Key West
Sunrise at Seaside Condo 2 Bedroom, holiday rental in Key West
Sunrise at Seaside Condo 2 Bedroom, holiday rental in Key West

Sunrise at Seaside Condo 2 Bedroom

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps, All pools
More info
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Key West Townhouse in stunning 5 Star Resort * Close to Duval Street and beach, holiday rental in Key West
Key West Townhouse in stunning 5 Star Resort * Close to Duval Street and beach, holiday rental in Key West
Key West Townhouse in stunning 5 Star Resort * Close to Duval Street and beach, holiday rental in Key West

Key West Townhouse in stunning 5 Star Resort * Close to Duval Street and beach

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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Key West Gulf front Home with private dock and pool.  , holiday rental in Key West
Key West Gulf front Home with private dock and pool.  , holiday rental in Key West
Key West Gulf front Home with private dock and pool.  , holiday rental in Key West

Key West Gulf front Home with private dock and pool.

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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Salt Ponds Sanctuary: Your Tranquil Escape, Shared Pool/Hot Tub & Proximity to t, holiday rental in Key West
Salt Ponds Sanctuary: Your Tranquil Escape, Shared Pool/Hot Tub & Proximity to t, holiday rental in Key West
Salt Ponds Sanctuary: Your Tranquil Escape, Shared Pool/Hot Tub & Proximity to t, holiday rental in Key West

Salt Ponds Sanctuary: Your Tranquil Escape, Shared Pool/Hot Tub & Proximity to t

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
More info
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Margaritaville: Live Like a Local in Old Town Key West! Dog-Friendly Conch House, holiday rental in Key West
Margaritaville: Live Like a Local in Old Town Key West! Dog-Friendly Conch House, holiday rental in Key West
Margaritaville: Live Like a Local in Old Town Key West! Dog-Friendly Conch House, holiday rental in Key West

Margaritaville: Live Like a Local in Old Town Key West! Dog-Friendly Conch House

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
More info
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NEW LISTING!  40’ Luxury Catamaran Yacht!, holiday rental in Key West
NEW LISTING!  40’ Luxury Catamaran Yacht!, holiday rental in Key West
NEW LISTING!  40’ Luxury Catamaran Yacht!, holiday rental in Key West

NEW LISTING! 40’ Luxury Catamaran Yacht!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps, All pools
More info
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Ananda - Discover Your Blissful Getaway, Steps from Smathers Beach, Shared Pool, holiday rental in Key West
Ananda - Discover Your Blissful Getaway, Steps from Smathers Beach, Shared Pool, holiday rental in Key West
Ananda - Discover Your Blissful Getaway, Steps from Smathers Beach, Shared Pool, holiday rental in Key West

Ananda - Discover Your Blissful Getaway, Steps from Smathers Beach, Shared Pool

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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Key West Bayfront Paradise - House and Private Pool!  Steps from shops and food, holiday rental in Key West
Key West Bayfront Paradise - House and Private Pool!  Steps from shops and food, holiday rental in Key West
Key West Bayfront Paradise - House and Private Pool!  Steps from shops and food, holiday rental in Key West

Key West Bayfront Paradise - House and Private Pool! Steps from shops and food

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, All pools
More info
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Nassau Suite just steps to Duval Tropical oasis  quiet location Downtown, holiday rental in Key West
Nassau Suite just steps to Duval Tropical oasis  quiet location Downtown, holiday rental in Key West
Nassau Suite just steps to Duval Tropical oasis  quiet location Downtown, holiday rental in Key West

Nassau Suite just steps to Duval Tropical oasis quiet location Downtown

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, All pools
More info
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Artist Cottage, holiday rental in Key West
Artist Cottage, holiday rental in Key West
Artist Cottage, holiday rental in Key West

Artist Cottage

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, All pools
More info
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Henry's Piece Of Paradise On The Ocean In Key West, holiday rental in Key West
Henry's Piece Of Paradise On The Ocean In Key West, holiday rental in Key West
Henry's Piece Of Paradise On The Ocean In Key West, holiday rental in Key West

Henry's Piece Of Paradise On The Ocean In Key West

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps, All pools
More info
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Single Family Home, 3 Bedroom, 2 Baths, and Pool.  Great Value!, holiday rental in Key West
Single Family Home, 3 Bedroom, 2 Baths, and Pool.  Great Value!, holiday rental in Key West
Single Family Home, 3 Bedroom, 2 Baths, and Pool.  Great Value!, holiday rental in Key West

Single Family Home, 3 Bedroom, 2 Baths, and Pool. Great Value!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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Vahevala: Your Tranquil Mid-Town Key West Oasis, 3BR Home, Pool & Close to Beach, holiday rental in Key West
Vahevala: Your Tranquil Mid-Town Key West Oasis, 3BR Home, Pool & Close to Beach, holiday rental in Key West
Vahevala: Your Tranquil Mid-Town Key West Oasis, 3BR Home, Pool & Close to Beach, holiday rental in Key West

Vahevala: Your Tranquil Mid-Town Key West Oasis, 3BR Home, Pool & Close to Beach

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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HISTORIC KEY WEST -  Cigar House - Sleeps 4, holiday rental in Key West
HISTORIC KEY WEST -  Cigar House - Sleeps 4, holiday rental in Key West
HISTORIC KEY WEST -  Cigar House - Sleeps 4, holiday rental in Key West

HISTORIC KEY WEST - Cigar House - Sleeps 4

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, All pools
More info
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Casa Del Sol, a Key West Vacation (Truman Annex), holiday rental in Key West
Casa Del Sol, a Key West Vacation (Truman Annex), holiday rental in Key West
Casa Del Sol, a Key West Vacation (Truman Annex), holiday rental in Key West

Casa Del Sol, a Key West Vacation (Truman Annex)

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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2 Bedroom, 2 Bath Condo with private balcony and Close to the Ocean, holiday rental in Key West
2 Bedroom, 2 Bath Condo with private balcony and Close to the Ocean, holiday rental in Key West
2 Bedroom, 2 Bath Condo with private balcony and Close to the Ocean, holiday rental in Key West

2 Bedroom, 2 Bath Condo with private balcony and Close to the Ocean

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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Tiki Too Townhouse, 2 blocks from Duval,Pool, Bikes, holiday rental in Key West
Tiki Too Townhouse, 2 blocks from Duval,Pool, Bikes, holiday rental in Key West
Tiki Too Townhouse, 2 blocks from Duval,Pool, Bikes, holiday rental in Key West

Tiki Too Townhouse, 2 blocks from Duval,Pool, Bikes

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps, All pools
More info
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HISTORIC KEY WEST  - Conch House - Sleeps 5, holiday rental in Key West
HISTORIC KEY WEST  - Conch House - Sleeps 5, holiday rental in Key West
HISTORIC KEY WEST  - Conch House - Sleeps 5, holiday rental in Key West

HISTORIC KEY WEST - Conch House - Sleeps 5

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps, All pools
More info
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KEY WEST and 3 Bikes or Walk Everywhere! 2 Porches, Pool, Parking & WIFI, holiday rental in Key West
KEY WEST and 3 Bikes or Walk Everywhere! 2 Porches, Pool, Parking & WIFI, holiday rental in Key West
KEY WEST and 3 Bikes or Walk Everywhere! 2 Porches, Pool, Parking & WIFI, holiday rental in Key West

KEY WEST and 3 Bikes or Walk Everywhere! 2 Porches, Pool, Parking & WIFI

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, All pools
More info
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Paradise: Beautifully Updated Conch Home, Pool, Quiet But Close Enough To Walk T, holiday rental in Key West
Paradise: Beautifully Updated Conch Home, Pool, Quiet But Close Enough To Walk T, holiday rental in Key West
Paradise: Beautifully Updated Conch Home, Pool, Quiet But Close Enough To Walk T, holiday rental in Key West

Paradise: Beautifully Updated Conch Home, Pool, Quiet But Close Enough To Walk T

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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 Seaside Condo 2 pools. sunny, quiet, near Old Town, holiday rental in Key West
 Seaside Condo 2 pools. sunny, quiet, near Old Town, holiday rental in Key West
 Seaside Condo 2 pools. sunny, quiet, near Old Town, holiday rental in Key West

Seaside Condo 2 pools. sunny, quiet, near Old Town

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, All pools
More info
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HISTORIC KEY WEST - Turtle House - Sleeps 6, holiday rental in Key West
HISTORIC KEY WEST - Turtle House - Sleeps 6, holiday rental in Key West
HISTORIC KEY WEST - Turtle House - Sleeps 6, holiday rental in Key West

HISTORIC KEY WEST - Turtle House - Sleeps 6

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps, All pools
More info
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Coral Hammock Poolside Home 3 bdrm 3 bath10 minute drive to Old Town Key West, holiday rental in Key West
Coral Hammock Poolside Home 3 bdrm 3 bath10 minute drive to Old Town Key West, holiday rental in Key West
Coral Hammock Poolside Home 3 bdrm 3 bath10 minute drive to Old Town Key West, holiday rental in Key West

Coral Hammock Poolside Home 3 bdrm 3 bath10 minute drive to Old Town Key West

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, All pools
More info
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Oceanfront 2 Bedroom 2 Bath Condo Key West Florida, holiday rental in Key West
Oceanfront 2 Bedroom 2 Bath Condo Key West Florida, holiday rental in Key West
Oceanfront 2 Bedroom 2 Bath Condo Key West Florida, holiday rental in Key West

Oceanfront 2 Bedroom 2 Bath Condo Key West Florida

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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Luxury Condominium in Old Town | Monthly Rental at Steamplant Key West, holiday rental in Key West
Luxury Condominium in Old Town | Monthly Rental at Steamplant Key West, holiday rental in Key West
Luxury Condominium in Old Town | Monthly Rental at Steamplant Key West, holiday rental in Key West

Luxury Condominium in Old Town | Monthly Rental at Steamplant Key West

Condo/Apartment
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps, All pools
More info
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Key West Beachfront Luxury 2/2 Condo  A212 No Hurricane Damage, holiday rental in Key West
Key West Beachfront Luxury 2/2 Condo  A212 No Hurricane Damage, holiday rental in Key West
Key West Beachfront Luxury 2/2 Condo  A212 No Hurricane Damage, holiday rental in Key West

Key West Beachfront Luxury 2/2 Condo A212 No Hurricane Damage

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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Tranquility by Smathers and 10 minute bike downtown Key West value savings, holiday rental in Key West
Tranquility by Smathers and 10 minute bike downtown Key West value savings, holiday rental in Key West
Tranquility by Smathers and 10 minute bike downtown Key West value savings, holiday rental in Key West

Tranquility by Smathers and 10 minute bike downtown Key West value savings

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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Key West Affordable Ocean View Condo. Clean priced well on the Atlantic, holiday rental in Key West
Key West Affordable Ocean View Condo. Clean priced well on the Atlantic, holiday rental in Key West
Key West Affordable Ocean View Condo. Clean priced well on the Atlantic, holiday rental in Key West

Key West Affordable Ocean View Condo. Clean priced well on the Atlantic

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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Top floor, two bedroom,two bath condo with private balcony,close to the Ocean, holiday rental in Key West
Top floor, two bedroom,two bath condo with private balcony,close to the Ocean, holiday rental in Key West
Top floor, two bedroom,two bath condo with private balcony,close to the Ocean, holiday rental in Key West

Top floor, two bedroom,two bath condo with private balcony,close to the Ocean

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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Frost Free at 1800 Atlantic overlooking Smathers Beach top floor & upgrades, holiday rental in Key West
Frost Free at 1800 Atlantic overlooking Smathers Beach top floor & upgrades, holiday rental in Key West
Frost Free at 1800 Atlantic overlooking Smathers Beach top floor & upgrades, holiday rental in Key West

Frost Free at 1800 Atlantic overlooking Smathers Beach top floor & upgrades

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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Tee by the Sea - Luxury 2/2 1/2, WIFI, pool, parking, Bikes, 3 night min., holiday rental in Key West
Tee by the Sea - Luxury 2/2 1/2, WIFI, pool, parking, Bikes, 3 night min., holiday rental in Key West
Tee by the Sea - Luxury 2/2 1/2, WIFI, pool, parking, Bikes, 3 night min., holiday rental in Key West

Tee by the Sea - Luxury 2/2 1/2, WIFI, pool, parking, Bikes, 3 night min.

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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Hemingways Atlantic Retreat overlooks Smathers Beach upgrades galore Key West, holiday rental in Key West
Hemingways Atlantic Retreat overlooks Smathers Beach upgrades galore Key West, holiday rental in Key West
Hemingways Atlantic Retreat overlooks Smathers Beach upgrades galore Key West, holiday rental in Key West

Hemingways Atlantic Retreat overlooks Smathers Beach upgrades galore Key West

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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Amazingly Transformed in 2022 Luxurious renovation Fantastic Ocean View, holiday rental in Key West
Amazingly Transformed in 2022 Luxurious renovation Fantastic Ocean View, holiday rental in Key West
Amazingly Transformed in 2022 Luxurious renovation Fantastic Ocean View, holiday rental in Key West

Amazingly Transformed in 2022 Luxurious renovation Fantastic Ocean View

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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Atlantic Paradise Found modern luxury Best pool in Key West fine finishes, holiday rental in Key West
Atlantic Paradise Found modern luxury Best pool in Key West fine finishes, holiday rental in Key West
Atlantic Paradise Found modern luxury Best pool in Key West fine finishes, holiday rental in Key West

Atlantic Paradise Found modern luxury Best pool in Key West fine finishes

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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