These Keys 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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- Marathon
- House (single)
- 2 bedrooms
- 2 bathrooms
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- Weekly rates
From $3,995 to $5,995 USD
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- Duck Key
- Cottage
- 3 bedrooms, sleeps 8
- 2.5 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
- 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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- Islamorada
- House (single)
- 10 bedrooms, sleeps 2-28
- 2-8 bathrooms
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- Weekly rates
From $4,900 to $11,000 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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- Melody Key
- House (single)
- 3 bedrooms, sleeps 6
- 3.5 bathrooms
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- Weekly rates
From $6,800 to $8,000 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)
- 2 bedrooms, sleeps 6
- 2.5 bathrooms
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- Weekly rates
From $2,786 to $3,486 USD
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- Plantation Key
- House (single)
- 3 bedrooms, sleeps 6
- 3.5 bathrooms
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- Key West
- Condo
- 2 bedrooms, sleeps 5
- 2.5 bathrooms
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- Marathon
- House (single)
- 4 bedrooms
- 4 bathrooms
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- Weekly rates
From $2,595 to $3,995 USD
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- Marathon
- Condo
- 2 bedrooms, sleeps 4 Ad & 2 Ch
- 2 1/2 bathrooms
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- Weekly rates
From $1,000 to $1,600 USD
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- Duck Key
- Condo
- 2 bedrooms, sleeps 7
- 2 bathrooms
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- Weekly rates
From $1,500 to $1,500 USD
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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
- Condo
- 2 bedrooms, sleeps 4
- 2 bathrooms
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- Weekly rates
From $1,750 to $3,430 USD
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- Islamorada
- Townhouse
- 2 bedrooms, sleeps 6
- 2.5 bathrooms
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- Weekly rates
From $1,560 to $1,872 USD
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- Marathon
- House (single)
- 8 bedrooms
- 6 bathrooms
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- Weekly rates
From $4,590 to $7,990 USD
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- Grassy Key
- House (single)
- 6 bedrooms, sleeps 16
- 5.5 bathrooms
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- Weekly rates
From $5,500 to $11,000 USD
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- Islamorada
- Condo
- 2 bedrooms
- 2 bathrooms
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- Weekly rates
From $900 to $1,500 USD
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- Big Pine Key
- House (single)
- 2 bedrooms, sleeps 4
- 2 bathrooms
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- Key West
- House (single)
- 4 bedrooms, sleeps 8
- 3 bathrooms
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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
- 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 Colony Beach
- Apts & Townhomes
- 2-3 bedrooms
- 2-3 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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- Grassy Key
- House (single)
- 4 bedrooms, sleeps 10
- 4 bathrooms
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- Weekly rates
From $4,500 to $8,500 USD
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- Marathon
- House (single)
- 4 bedrooms, sleeps 10
- 4 bathrooms
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- Weekly rates
From $1,600 to $4,500 USD
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- Key Colony Beach
- Duplex
- 2 bedrooms, sleeps 4
- 2 bathrooms
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- Marathon
- House (single)
- 5 bedrooms
- 4 bathrooms
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- Key West
- Condo
- 2 bedrooms, sleeps 2-5
- 2 bathrooms
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- Marathon
- House (single)
- 3 bedrooms
- 3 bathrooms
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- Weekly rates
From $2,495 to $3,895 USD
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- Cudjoe Key
- House (single)
- 2 bedrooms, sleeps 6
- 2 bathrooms
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- Marathon
- House (single)
- 4 bedrooms
- 2 bathrooms
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- Weekly rates
From $2,495 to $3,995 USD
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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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- Cudjoe Key
- House (single)
- 3 bedrooms, sleeps 6 to 8
- 2 bathrooms
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- Weekly rates
From $1,000 to $1,125 USD
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- Key West
- Suite
- sleeps 4
- 1 bathrooms
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- Weekly rates
From $1,100 to $1,700 USD
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- Duck Key
- Villa
- 2 bedrooms, sleeps 5
- 2 bathrooms
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- Weekly rates
From $1,500 to $2,100 USD
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- Duck Key
- House (single)
- 2-4 bedrooms, sleeps 4-8
- 1.5 - 4 bathrooms
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- Weekly rates
From $3,000 to $3,500 USD
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- Summerland Key
- House (single)
- 2 bedrooms
- 2 bathrooms
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- Key West
- Cottage
- 2 bedrooms, sleeps 4
- 2 bathrooms
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- Weekly rates
From $2,100 to $3,430 USD
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- Islamorada
- Condo
- 1 bedrooms, sleeps 2-4
- 2 bathrooms
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- Duck Key
- Villa
- 2 bedrooms, sleeps 2-4
- 1.5 bathrooms
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- Weekly rates
From $3,100 to $3,500 USD
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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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- Duck Key
- Villa
- 2-4 bedrooms, sleeps 2 - 10
- 1-3 bathrooms
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- Marathon
- House (single)
- 1 bedrooms
- 1 bathrooms
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- Weekly rates
From $2,895 to $3,895 USD
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- Marathon
- House (single)
- 2 bedrooms
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- Weekly rates
From $2,995 to $3,995 USD
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- Key West
- Condo
- 1 bedrooms, sleeps 4
- 1 bathrooms
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- Weekly rates
From $1,036 to $1,246 USD
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- Key West
- Cottage
- sleeps 2
- 1 bathrooms
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- Weekly rates
From $1,386 to $1,806 USD
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- Key Colony Beach
- Condo
- 2 bedrooms, sleeps 4
- 2 bathrooms
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- Weekly rates
From $1,000 to $1,400 USD
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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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- Marathon
- HouseBoat
- 1 bedrooms, sleeps 4-5
- 1 bathrooms
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- Weekly rates
From $2,995 to $4,195 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
- Condo
- 2 - 4 (Vari bedrooms, sleeps 4 - 10 (Var
- 2 - 4 (Var bathrooms
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- Weekly rates
From $1,330 to $4,900 USD
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- Key West
- Home
- 3 bedrooms, sleeps 6
- 2.5 bathrooms
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- Islamorada
- Villa
- 2 bedrooms, sleeps 4-8
- 2 bathrooms
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- Key West
- Townhouse
- 7 bedrooms
- 9 bathrooms
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- Nautical Maps shown as Russell Key
- Private Island-all to yourself
- 3 bedrooms, sleeps 8
- 3 bathrooms
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- Weekly rates
From $5,595 to $6,995 USD
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- Marathon
- House (single)
- 2 bedrooms
- 1 bathrooms
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- Weekly rates
From $700 to $1,300 USD
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- Big Pine Key
- House (single)
- 2 to 10 bedrooms, sleeps 4 to 20
- 1.5 to 5.5 bathrooms
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- Key West
- House (single)
- 3 bedrooms, sleeps 6
- 2 bathrooms
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- Weekly rates
From $2,310 to $4,410 USD
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- Key West
- House (single)
- 4 bedrooms, sleeps 9
- 5 bathrooms
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- Weekly rates
From $4,830 to $8,540 USD
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- Islamorada
- Apartment
- 4 bedrooms, sleeps 8-10
- 3 bathrooms
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- Weekly rates
From $3,000 to $3,500 USD
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- Summerland Key
- House (single)
- 4 bedrooms, sleeps 8
- 3 bathrooms
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- Key Largo
- Townhouse
- 3 bedrooms, sleeps 8
- 3 bathrooms
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- Weekly rates
From $1,650 to $2,200 USD
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- Grassy Key
- House (single)
- 4 bedrooms, sleeps 8 Adults +
- 2 bathrooms
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- Weekly rates
From $2,800 to $6,200 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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- Key Colony Beach
- House (multifamily)
- 3 bedrooms, sleeps 8
- 2 bathrooms
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- Weekly rates
From $1,100 to $1,850 USD
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- Key Largo
- Yacht
- 1 bedrooms, sleeps 2-6
- 1 bathrooms
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- Weekly rates
From $840 to $2,100 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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Big Pine Key |
2 to 10 BR |
1.5 to 5.5 BA |
4 to 20 |
The San Marco Homes & Bungalow - Big Pine Key |
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Big Pine Key |
2 BR |
2 BA |
4 |
Fisherman’s Paradise This Home Will Not Disappoint - Florida |
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Big Pine Key |
2 BR |
2 BA |
4 |
Beautiful Home - Great Views - Big Pine Key |
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Big Pine Key |
3 BR |
2 BA |
6 |
Magnificent Open Water Views - Big Pine Key Vacation Home |
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Big Pine Key |
3 BR |
1 BA |
8-9 |
Fabulous Florida Keys Vacation in Port Pine Heights |
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Big Pine Key |
3 BR |
2 BA |
6 |
Tropical Bay |
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Big Pine Key |
3 BR |
2 BA |
6 |
Gorgeous Views - Big Pine Key |
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Big Pine Key |
3 BR |
3 BA |
6 |
Big Pine Key Oceanfront Vacation Home - Atlantis |
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Cudjoe Key |
1 BR |
1 BA |
2 |
Magnificent Cudjoe Key Vacation Home |
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Cudjoe Key |
2 BR |
2 BA |
4 |
Vacation in Paradise - Located on Cudjoe Key |
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Cudjoe Key |
2 BR |
2 BA |
6 |
Tropical Paradise Oceanfront Home with Pool |
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Cudjoe Key |
3 BR |
2 BA |
6 |
Suncatcher's Dream - Paradise in the Beautiful Florida Keys. |
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Cudjoe Key |
3 BR |
2 BA |
6 |
Cudjoe Ocean Shores Room for all your water toys |
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Cudjoe Key |
3 BR |
2 BA |
6 |
Waterfront Vacation Rental - Casa Rosado |
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Cudjoe Key |
3 BR |
2 BA |
6 to 8 |
Breathtaking Ocean Views with 60ft dock on crystal clean canal |
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Cudjoe Key |
3 BR |
2 BA |
6 |
Quiet Waters - Cudjoe Key |
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Cudjoe Key |
3 BR |
2 BA |
6 |
Cudjoe Paradise |
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Duck Key |
2-4 BR |
1.5 - 4 BA |
4-8 |
Florida Key Villa - Santuary Villas |
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Duck Key |
2 BR |
1.5 BA |
2-4 |
Enjoy Your Very Own Cozy Florida Key Villa! |
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Duck Key |
2 BR |
2 BA |
7 |
Waterfront Keys to Memories - Duck Key |
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Duck Key |
2-4 BR |
1-3 BA |
2 - 10 |
This Luxurious Duck Key Vacation Rental Condo Can Be Your Dream Vacation... |
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Duck Key |
2 BR |
2 BA |
5 |
Two-Bedroom Conch Villa In Florida Keys |
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Duck Key |
3 BR |
2.5 BA |
8 |
Beautiful Florida Key Three Bedroom Cottage Villa |
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Grassy Key |
4 BR |
4 BA |
10 |
Gorgeous Views - Gorgeous Home - Marathon / Grassy Key property is managed by "American Paradise" |
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Grassy Key |
4 BR |
2 BA |
8 Adults + |
Grassy Key/Marathon Gulf Front Property - property is managed by "American Paradise" |
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Grassy Key |
6 BR |
5.5 BA |
16 |
Spectacular Gulf Front Luxury Home on 2.5 Acres property is managed by "American Paradise" |
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Islamorada |
1 BR |
2 BA |
2-4 |
Bayside 1st floor Condo on Florida Bay - Islamorada, Florida |
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Islamorada |
2 BR |
2 BA |
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Oceanfront Islamorada Condo Rentals Located in the Beautiful Florida Keys- www.OceanfrontParadise.com |
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Islamorada |
2 BR |
2.5 BA |
6 |
Islamorada Futura Yacht Club - Swim, Fish, & Relax |
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Islamorada |
2 BR |
2 BA |
6 |
Futura Yacht Club - Tropical Paradise - Islamorada |
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Islamorada |
2 BR |
2 BA |
4-8 |
THE KEYS KOTTAGE has it all - Islamorada, Florida |
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Islamorada |
3 BR |
3 BA |
6 |
Best Florida Keys Rental - Islamorada |
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Islamorada |
4 BR |
3 BA |
8-10 |
The Perfect Getaway with Heated Pool and Jacuzzi - IN THE HEART of ISLAMORADA |
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Islamorada |
5 BR |
3.5 BA |
13 |
Exclusive Oceanfront Private Gated Estate Home with 200 feet of Oceanfront Islamorada in the Florida Keys |
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Islamorada |
10 BR |
2-8 BA |
2-28 |
PRISTINE OCEANFRONT HOME IN ISLAMORADA, THE FLORIDA KEYS - Rent All or Rent Separately |
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Key Colony Beach |
2-3 BR |
2-3 BA |
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Key Colony Point borders the waters edge of paradise... offering breathtaking sunsets daily, and an escape to paradise well worth planning every year |
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Key Colony Beach |
2 BR |
2 BA |
4 |
Private Beach-Ocean View-Pool-Walking Distance to Restaurants - Key Colony Beach |
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Key Colony Beach |
2 BR |
2 BA |
4 |
Key Colony Sunrise Retreat - Book Now for a $100.00 Gas Credit |
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Key Colony Beach |
3 BR |
2 BA |
8 |
Bright & Breezy - Very Popular Home - WiFi & Cabana Club Included! |
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Key Colony Beach |
6 BR |
BA |
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Key Colony Beach Waterfront Pool Home |
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Key Largo |
BR |
BA |
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Key Largo Yacht Rentals - "The Key in Life is to Take the Water" |
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Key Largo |
1 BR |
1 BA |
2-6 |
BAY FRONT Cottages & your own FREE 22’ SAILBOAT + Paddle Boats, Kayaks, Canoes, Fishing & Snorkeling Gear, Sun Sets, Dolphins & Manatees Tiki Huts |
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Key Largo |
2 BR |
1 BA |
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Key Largo Condo Located in the Moon Bay Yacht and Tennis Club |
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Key Largo |
3 BR |
3 BA |
8 |
Fabulous Marina View! |
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Key Largo |
4 BR |
3 BA |
8 |
Luxury oceanfront villa at Mariner's Club Key Largo |
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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 |
BR |
1 BA |
4 |
SAVE 20% thru Dec. 15, 2009 - Sleep 4 - $110.40/night |
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Key West |
0 BR |
1 BA |
2 |
SAVE 20% thru Dec 14, 2009 - Sleep 2 for $158.40/night |
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Key West |
1 BR |
1 BA |
4 |
SAVE 20% thru Dec 14, 2009 - Sleep 4 for $134.40/night |
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Key West |
1 BR |
2 BA |
2 |
Charming Key West 1 Bedroom Bungalow |
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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 |
4 |
Key West Cottage - Butterfly Garden |
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Key West |
1 BR |
1 BA |
2-4 |
Key West Carriage Cottage |
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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 |
4 |
Egret one bedroom cottages in the heart of the historic district |
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Key West |
1 BR |
1 BA |
4 |
Totally Renovated & Stylish Conch Cottage |
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Key West |
1 BR |
1 BA |
4 |
SAVE 20% thru Dec. 14, 2009 - Sleep 4 - $118.40/night |
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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 |
1 BR |
1 BA |
2 |
Key West 1 Bedroom 1 Bath Cottage - Ann Street Tranquility |
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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 |
Vintage Luxury Cottage Vacation Rental - Just Off Upper Duval Street with 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 |
Conch Condo - upstairs two bedroom two bath in historic district |
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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 |
4-6 |
Key West Southern Sunrise Vacation Rental |
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Key West |
2 BR |
2 BA |
4 |
Oceanfront Living at Key West Beach Club #204 |
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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 |
2.5 BA |
6 |
Two bedroom / two and a half 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 |
6 |
Key West - Havana Moon Vacation Home |
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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 |
6 |
Key West Vacation Rentals |
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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 |
2.5 BA |
6 |
SPINNAKER SAIL - Key West, FL |
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Key West |
2 BR |
2 BA |
4 |
Mahogany Breezes |
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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 |
4-6 |
Ocean Front Luxury Condominium at 1800 Atlantic #228 |
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Key West |
2 BR |
2 BA |
6 |
Two bedroom / two bathroom condo near the Atlantic Ocean |
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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 BA |
4 |
Oceanfront 2 Bedroom Key West Condo - 1800 Atlantic |
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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 |
6 |
Key West Crown Jewel - Enjoy Key West in STYLE!! |
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Key West |
2 BR |
3 BA |
6 |
Casa Flora is the perfect vacation for the avid golfer |
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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 |
4-6 |
Island Village Cottage Vacation Rental - Key West |
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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 BA |
2-4 |
Click here to view more details about this property |
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Key West |
2 BR |
2 BA |
4 |
Wonderful Pool Home in the Casa Marina District of Key West |
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Key West |
2 BR |
2 BA |
4 |
Key West 2 Bedroom Southard Sophistication Home |
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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 BA |
4 |
Josephine - Luxurious Key West Vacation Home |
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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 |
2-6 |
Key West - Cockadoodle Cottage with Pool |
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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 |
6 |
Fully Renovated Luxury Home in the heart of Old Town Key West. |
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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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Featured
Property Managers |
| ActionKeysRealty.com Whether you are planning your vacation or planning to move to the beautiful Florida Keys, we have information to help you. |
| Island Breeze Realty Welcome to the Fabulous Florida Keys...Whether you are interested in Buying or Renting one of our Luxury Waterfront Vacation Rental Homes, We are committed to serving you...
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| 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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Seabird Key, Private Island, Florida Keys...with a stunning home, 19' Boston Whaler, Kayaks, Hobie Cat, and a long list of unexpected amenities.
Nautical Maps shown as Russell Key Private Island-all to yourself, 3 bedrooms, sleeps 8, 3 bathrooms Weekly rates from $5,595 to $6,995 USD
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Fabulous Marina View!
Key Largo Townhouse, 3 bedrooms, sleeps 8, 3 bathrooms Weekly rates from $1,650 to $2,200 USD
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