These Key West vacation homes, condos, villas, cabins, cottages, chalets, and bed & breakfasts are presented by their owners or agents.
Please contact them directly with your inquiries. Click on the underlined descriptions below for more details and property photos.
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- Key West
- House (single)
- 4 bedrooms, sleeps 8
- 3 bathrooms
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- Key West
- Townhouse
- 7 bedrooms
- 9 bathrooms
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- Key West
- House (single)
- 7 bedrooms, sleeps 16
- 7 bathrooms
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- Weekly rates
From $6,800 to $9,300 USD
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- Key West
- Condo
- 2 bedrooms, sleeps 5
- 2.5 bathrooms
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- Key West
- Villa
- 4 bedrooms, sleeps 2-10
- 3.5 bathrooms
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- Weekly rates
From $3,800 to $4,800 USD
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- Key West
- Cottage
- 1 bedrooms, sleeps 2
- 1 bathrooms
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- Weekly rates
From $1,375 to $1,876 USD
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- Key West
- Condo
- 2 - 4 (Vari bedrooms, sleeps 4 - 10 (Var
- 2 - 4 (Var bathrooms
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- Key West
- Condo
- 3 bedrooms, sleeps 6
- 2 bathrooms
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- Weekly rates
From $2,000 to $2,800 USD
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- Key West
- Condo
- 2 bedrooms, sleeps 2-5
- 2 bathrooms
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- Key West
- Cottage
- 2 bedrooms, sleeps 4
- 2 bathrooms
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- Key West
- Cottage
- 3 bedrooms, sleeps 6
- 2 bathrooms
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- Weekly rates
From $2,856 to $3,556 USD
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- Key West
- Villa
- 6 bedrooms, sleeps 14
- 5 bathrooms
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- Weekly rates
From $5,850 to $7,500 USD
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- Key West
- Villa
- 3 bedrooms, sleeps 8
- 2.5 bathrooms
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- Weekly rates
From $3,500 to $4,500 USD
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- Key West
- Suite
- 1 bedrooms, sleeps 4
- 1 bathrooms
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- Weekly rates
From $1,176 to $1,736 USD
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- Key West
- House (single)
- 2 bedrooms, sleeps 6
- 2.5 bathrooms
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- Weekly rates
From $2,786 to $3,486 USD
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- Key West
- House (single)
- 6 bedrooms, sleeps 12-14
- 4 bathrooms
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- Weekly rates
From $5,000 to $7,500 USD
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- Key West
- House (single)
- 4 bedrooms, sleeps 9
- 5 bathrooms
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- Key West
- Condo
- 2 bedrooms, sleeps 4
- 2 bathrooms
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- Key West
- House (single)
- 3 bedrooms, sleeps 6
- 2 bathrooms
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- Key West
- House (single)
- 4 bedrooms, sleeps 8
- 3 bathrooms
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- Weekly rates
From $2,500 to $5,500 USD
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- Key West
- House (single)
- 5 bedrooms, sleeps 10
- 3 bathrooms
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- Weekly rates
From $4,450 to $5,350 USD
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- Key West
- Cottage
- 2 bedrooms, sleeps 4-6
- 2 bathrooms
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- Weekly rates
From $1,850 to $2,550 USD
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- Key West
- Home
- 3 bedrooms, sleeps 6
- 2.5 bathrooms
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- Key West
- Townhouse
- 2 bedrooms, sleeps 4
- 2 bathrooms
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- Weekly rates
From $1,500 to $2,100 USD
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- Key West
- House (single)
- 3 bedrooms, sleeps 6
- 3 bathrooms
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- Weekly rates
From $4,000 to $6,000 USD
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Rental Locations (Listed alphabetically by City or Town)
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City |
BR(s) |
BA(s) |
Sleeps |
Description |
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Big Coppitt Key |
6 BR |
3.5 BA |
10 |
Key West Vacation Home, Views of the bay, Private, Tiki Hut. |
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Key West |
Studio |
1 BA |
2 |
"Casa Atlantica Studio" Experience Breathtaking Ocean Views From This Secluded Private Studio. |
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Key West |
BR |
BA |
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Luxurious Key West Vacation Home |
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Key West |
1 - 4 BR |
1 - 2 BA |
4 per |
"Pete's Cottages" Beautiful Vacation Rental Cottages |
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Key West |
1 BR |
1 BA |
2-4 |
Key West Garden Suite - Key West, Florida |
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Key West |
1 BR |
1 BA |
4 |
Egret one bedroom cottages in the heart of the historic district |
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Key West |
1 BR |
1 BA |
2-4 |
Key West Studio Suite in the Gardens, Near Restaurants, and The Beach. |
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Key West |
1 BR |
1 BA |
2 |
Land’s End one bedroom one bath cottage available monthly near historic seaport |
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Key West |
1 BR |
1 BA |
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"Buddy Shula's Paradise Place" Spacious 1 Bedroom Key West Vacation Rental |
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Key West |
1 BR |
1 BA |
2-4 |
Key West Studio Suite - Peaceful & Serene yet close to city activities. |
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Key West |
1 BR |
1 BA |
2 |
Fabulous Key West Cottage with Art-Deco Interior Design |
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Key West |
1 BR |
1 BA |
4 |
Key West Suite, Private Jacuzzi, Near Activities Downtown. |
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Key West |
1 BR |
1 BA |
2-4 |
Key West Suite - Near Beach, Restaurants and Duval Street. |
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Key West |
1 BR |
1 BA |
4 |
Key West Cottage - Butterfly Garden |
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Key West |
1 BR |
1 BA |
4 |
Vintage Luxury Cottage Vacation Rental - Just Off Upper Duval Street with Pool |
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Key West |
1 BR |
1 BA |
2 |
Key West Cottage For Two with Hot tub, tiki Bar, Private Yard. |
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Key West |
1 BR |
1 BA |
2-4 |
Key West Carriage Cottage |
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Key West |
1 BR |
1 BA |
4 |
Margaret’s Harborside Cottage one bedroom one bath cottage available monthly near Historic seaport |
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Key West |
1 BR |
1 BA |
2 |
"Key Lime Calypso "A great vacation home in the heart of Old Town Key West! |
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Key West |
1 BR |
1 BA |
2 |
"Casa Atlantica One" - Breathtaking Ocean Views From This Secluded Private Ocean Front Apartment. |
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Key West |
2 BR |
1.5 BA |
6 |
Emerald Sea - Key West, Florida |
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Key West |
2 BR |
2 BA |
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Luxurious Key West Vacation Home |
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Key West |
2 BR |
2 BA |
2-6 w/ Pool |
Henry's Penthouse On the Ocean In Key West |
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Key West |
2 BR |
1 BA |
4-6 |
Romantic Garden Cottage in Key West |
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Key West |
2 BR |
BA |
6 |
Duval Street Hideaway - two bedroom two 1/2 bath townhome in historic district |
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Key West |
2 BR |
2.5 BA |
5 |
Southern Comfort - Two bedroom two 1/2 bath townhome available monthly |
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Key West |
2 BR |
2 BA |
4-6 |
Island Village Cottage Vacation Rental - Key West |
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Key West |
2 BR |
1.5 BA |
2-6 |
Flamboyant Tree Cottage Vacation Rental - off Upper Duval Street with Jacuzzi |
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Key West |
2 BR |
2.5 BA |
6 |
Fantastic Key West Vacation Rental - Amelia Home |
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Key West |
2 BR |
2 BA |
4 |
Catherine St. Getaway- Old Town Home with Pool |
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Key West |
2 BR |
2 BA |
4-6 |
Historic Home,In Old Town Key West,Heart of the Cities Culture. |
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Key West |
2 BR |
1 BA |
2-5 |
Key West - Secret Courtyard Cottage Vacation Rental |
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Key West |
2 BR |
2 BA |
2-4 |
Cottage in the heart of Key West Bustling Seaport,Private Pool. |
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Key West |
2 BR |
2 BA |
4 |
Howe St. Hideaway two bedroom two bath home located in the Old Town in a very peaceful area. |
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Key West |
2 BR |
2.5 BA |
6 |
Key West Found - 2 Bedroom Townhouse - Historic Section Key West |
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Key West |
2 BR |
2 BA |
4 |
Ocean Front Luxury Condominium at 1800 Atlantic #435 |
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Key West |
2 BR |
2.5 BA |
5 |
BAMBOO KEY - KEY WEST |
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Key West |
2 BR |
2 BA |
4 |
"Beach Club #201" Luxurious Oceanfront Condo with Magnificent views of the Ocean |
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Key West |
2 BR |
2 BA |
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Key West Island Elegance |
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Key West |
2 BR |
2 BA |
6 |
Tropical Breeze - two bedroom two bath oceanfront condo |
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Key West |
2 BR |
2 BA |
6 |
Key West Crown Jewel - Enjoy Key West in STYLE!! |
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Key West |
2 BR |
2 BA |
4 |
Vacation Rental in Key West Meadows,Pool,Private Cottage. |
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Key West |
2 BR |
1.5 BA |
4 |
"Shipyard Palms " Charming Gated Comunity Condo in the heart of HIstoric District |
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Key West |
2 BR |
2 BA |
6 |
Key West Sweet Sunshine Garden Cottage Vacation Rentals |
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Key West |
2 BR |
2 BA |
4 |
Key West - Good Day Sunshine! |
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Key West |
2 BR |
2.5 BA |
6 |
Larkin House,Open,Airy, Gated Neighborhood,Pool. |
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Key West |
2 BR |
2 BA |
4 |
Mahogany Breezes |
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Key West |
2 BR |
2 BA |
4 |
"Havana Lane" An Old Town Vacation Rental Retreat |
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Key West |
2 BR |
2.5 BA |
4 |
"Dockside Villa" - 2 bedroom 2 1/2 bath Townhome with Dockage |
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Key West |
2 BR |
1.5 BA |
5 |
Carols Bungalow - Two bedroom one 1/2 bath townhome available monthly |
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Key West |
2 BR |
1 BA |
4 |
Aquamarine - two bedroom one bath upstairs condo |
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Key West |
2 BR |
2 BA |
4 |
Island Oasis Garden Home Vacation Rental - Key West |
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Key West |
2 BR |
2 BA |
4 |
"Beach Club #303" Luxurious Oceanfront Condo with Magnificent views of the Ocean |
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Key West |
2 BR |
2 BA |
2-6 |
Down Island Digs Vacation Rental in Old Town Key West |
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Key West |
2 BR |
2 BA |
4 |
Upscale Modern Key West Cottage - Tropical Chill |
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Key West |
2 BR |
2.5 BA |
6 |
SPINNAKER SAIL - Key West, FL |
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Key West |
2 BR |
2 BA |
6 |
Suite Paradise - Wonderful Key West Home with Private Pool |
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Key West |
2 BR |
2 BA |
6 |
This great two bedroom two bath condominium at 1800 Atlantic Condominiums offers you a wonderful relaxing garden view. |
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Key West |
2 BR |
2 BA |
4-6 |
Ocean Front Luxury Condominium at 1800 Atlantic #228 |
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Key West |
2 BR |
2 BA |
6 |
Key West - Havana Moon Vacation Home |
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Key West |
2 BR |
2 BA |
6 |
Atlantic Retreat- two bedroom two bath oceanview condo on Atlantic |
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Key West |
2 BR |
2 BA |
4 |
Southern Wind - two bedroom two bath home in historic district |
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Key West |
2 BR |
2.5 BA |
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Foundry on the Waterfront - Key West |
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Key West |
2 BR |
2.5 BA |
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CARIBBEAN CHARM - KEY WEST |
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Key West |
2 BR |
2.5 BA |
6 |
Old Town Key West Pool Home with 2 Off-Street Parking Spaces! |
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Key West |
2 BR |
2 BA |
2-5 |
Henry's Piece Of Paradise On The Ocean In Key West |
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Key West |
2 BR |
2 BA |
6 |
A Zen Garden - Tranquil 2 bedroom 2 bath oceanfront condo |
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Key West |
2 BR |
1 BA |
4 |
Key West Charming - Two bedroom one bath condominium |
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Key West |
2 BR |
2 BA |
4 |
"La Brisa 206E" Ocean front condo with beautiful ocean view. |
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Key West |
2 BR |
2.5 BA |
6 |
Artist's House,2 Bedroom Condo,Downtown Key West. |
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Key West |
2 BR |
1 BA |
4 |
Shipyard Condo 'Havana Views' - Key West |
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Key West |
2 BR |
2 BA |
5 |
Truman Annex Shipyard Cottage |
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Key West |
2 - 4 (Vari BR |
2 - 4 (Var BA |
4 - 10 (Var |
"Duval Square" Vacation Rental Condo's Conveniently Located |
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Key West |
2 BR |
2 BA |
2-4 |
Click here to view more details about this property |
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Key West |
2 BR |
2.5 BA |
6 |
Spa on Duval - two bedroom two 1/2 bath townhome on Duval St |
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Key West |
2 BR |
2.5 BA |
6 |
Duval Sea Turtle two bedroom two 1/2 bath on Duval Street |
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Key West |
2 BR |
2 BA |
4 |
"Beach Club #103" Luxurious Oceanfront Condo with Magnificent views of the Ocean |
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Key West |
2 BR |
2 BA |
4-6 |
Key West Southern Sunrise Vacation Rental |
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Key West |
2 BR |
2.5 BA |
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BRUBECK COTTAGE - KEY WEST |
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Key West |
2 BR |
1 BA |
4 |
Key West Cottage with Jacuzzi - Ideal for Relaxing. |
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Key West |
2 BR |
2 BA |
4 |
"La Brisa 405East" Vacation Rental Condo With Beautiful Ocean View |
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Key West |
2 BR |
2 BA |
2-6 |
Key West - Cockadoodle Cottage with Pool |
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Key West |
2 BR |
2 BA |
6 |
Fully Renovated Luxury Home in the heart of Old Town Key West. |
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Key West |
2 BR |
2 BA |
5 |
Conch Condo - upstairs two bedroom two bath in historic district |
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Key West |
2 BR |
2 BA |
6 |
Key West Vacation Rentals |
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Key West |
2.5 BR |
2 BA |
4 |
Duval on the Square Two bedroom two and one half bath townhome in historic district available monthly only |
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Key West |
3 BR |
2 BA |
6 |
Hideaway in Key West with Pool - Near Activities & Restaurants. |
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Key West |
3 BR |
2.5 BA |
6 |
Mediterranean Caribbean Villa in Key West |
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Key WEst |
3 BR |
2 BA |
6 |
"La Brisa 308North" - Great beach front condo on Salt Pond Nature Preserve |
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Key West |
3 BR |
2 BA |
2-6 |
Island Cosmopolitan Vacation Rental with Private Pool & High Speed Internet |
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Key West |
3 BR |
2 BA |
8 |
Shipyard Condo 'Sandcastles' - Key West |
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Key West |
3 BR |
2 BA |
6 |
Key West Waterfront Vacation Home in Prestigious Key Haven |
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Key West |
3 BR |
2 BA |
6 |
"Casa De Cuba" A Vacation Rental House With A Cuban Twist! |
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Key West |
3 BR |
3 BA |
6 |
In the Heart of "Old Town" Beautiful Vacation Home in Key West, Florida |
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Key West |
3 BR |
2.5 BA |
6-8 |
Coco's Poolside Retreat Key West Vacation Rental |
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Key West |
3 BR |
3 BA |
8 |
Lighthouse Keep - Three bedroom three bath townhome. GREAT VALUE |
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Key West |
3 BR |
3 BA |
6-8 |
Private Key West Villa |
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Key West |
3 BR |
3.5 BA |
6 |
"Duval Roost" A Beautiful Vacation Home With Screened Balcony Overlooking The Pool |
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Key West |
3 BR |
3.5 BA |
6 |
ADMIRAL'S PARADISE - KEY WEST |
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Key West |
3 BR |
2.5 BA |
6 |
Golf Club Dr. in The Sanctuary at The Key West Golf Club. |
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Result Page:
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Select additonal pages to continue viewing the listings alphabetically by city/town
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Featured
Property Managers |
| www.TrumanAnnex.com We are the exclusive on-site rental agency for the Truman Annex and Key West Golf Club. Our staff of professional, licensed Realtors® is here to accommodate your needs whether you are vacationing, in need of temporary housing or are looking for a permanent home |
| Bone Island Vacation Rentals Key West, FL
Rates Vary
Our Key West Accommodations are suited for all your vacation needs. Whether you're traveling alone or in a group, we can provide the perfect setup. We offer B&B lodging, homes and cottages, suites, and condos that meet every tourist's holiday expectation. |
| www.AtHomeKeyWest.com Located throughout Key West many homes, cottages and compounds are open for vacation rentals. These homes offer a private haven in the tropical beauty of Key West Many different styles and amenities are available. |
| www.RentKeyWest.com Key West, FL
Rates Vary
Rent a private home, cottage, villa, or condo as an alternative to your typical Key West hotel stay. |
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