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Vacation Rentals Contact
Truman Annex
(305) 292-1881 ~ 1 (800) 884-RENT
rentals@compass-realty.com

Key West Golf Club
(305) 292-1480 ~ 1 (800) 721-RENT
rentals@compass-realty.com

Truman Annex Real Estate Sales
(305) 296-7078
trumanannex@compass-realty.com

Key West Golf Club
(305) 292-0020
compassrealty@compass-realty.com

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Waterfront Key West Vacation Rentals
Found 27 Listings
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Vacation Rental in Key West, FL
Truman Annex
Condo
 Bamboo Key - Truman Annex

Rates starting at: $2,400/week
Type: Condo
Sleeps: 5
Beds / Baths: 2 / 2.5

Check Availability for Bamboo Key Now!
 
Vacation Rental in Key West, FL
Truman Annex
Condo
 Catch of the Day - Truman Annex

Rates starting at: $3,000/week
Type: Condo
Sleeps: 7
Beds / Baths: 3 / 2.5

Check Availability for Catch of the Day Now!
 
Aug to October 22nd $1900 per week!!
Vacation Rental in Key West, FL
Truman Annex
Condo
 Chilmark South - Truman Annex

Rates starting at: $2400/wk
Type: Condo
Sleeps: 5
Beds / Baths: 2 / 2

Check Availability for Chilmark South Now!
 
Vacation Rental in Key West, FL
Truman Annex
Private Home
 Dolphin Watch - Truman Annex

Rates starting at: $4,500/week
Type: Private Home
Sleeps: 8
Beds / Baths: 4 / 3

Check Availability for Dolphin Watch Now!
 
Vacation Rental in Key West, FL
Truman Annex
Condo
 Driftwood Buoy - Truman Annex

Rates starting at: $2400/wk
Type: Condo
Sleeps: 5
Beds / Baths: 2 / 2.5

Check Availability for Driftwood Buoy Now!
 
Vacation Rental in Key West, FL
Truman Annex
Condo
 Gulfstream Drift - Truman Annex

Rates starting at: $3000/week
Type: Condo
Sleeps: 6
Beds / Baths: 3 / 3

Check Availability for Gulfstream Drift Now!
 
Vacation Rental in Key West, FL
Truman Annex
Condo
 Harbour Walk - Truman Annex

Rates starting at: $2,400/week
Type: Condo
Sleeps: 5
Beds / Baths: 2 / 2

Check Availability for Harbour Walk Now!
 
Vacation Rental in Key West, FL
Truman Annex
Condo
 Mariner's Landing - Truman Annex

Rates starting at: $2,400/week
Type: Condo
Sleeps: 5
Beds / Baths: 2 / 2

Check Availability for Mariner's Landing Now!
 
Vacation Rental in Key West, FL
Truman Annex
Condo
 Naught in your Wildest Dreams - Truman Annex

Rates starting at: $2400.00
Type: Condo
Sleeps: 5
Beds / Baths: 2 / 2.5

Check Availability for Naught in your Wildest Dreams Now!
 
Vacation Rental in Key West, FL
Truman Annex
Condo
 Nautical Adventures - Truman Annex

Rates starting at: $2400/wk
Type: Condo
Sleeps: 5
Beds / Baths: 2 / 2.5

Check Availability for Nautical Adventures Now!
 
$1600 PER WEEK FOR THE MONTH OF JUNE!!
Vacation Rental in Key West, FL
Truman Annex
Condo
 Next Stop Havana - Truman Annex

Rates starting at: $2400.00
Type: Condo
Sleeps: 5
Beds / Baths: 2 / 2

Check Availability for Next Stop Havana Now!
 
Vacation Rental in Key West, FL
Truman Annex
Condo
 Ocean Breeze - Truman Annex

Rates starting at: $2400.00
Type: Condo
Sleeps: 5
Beds / Baths: 2 / 2.5

Check Availability for Ocean Breeze Now!
 
Vacation Rental in Key West, FL
Truman Annex
Condo
 Ocean Cathedral - Truman Annex

Rates starting at: $1900/wk
Type: Condo
Sleeps: 4
Beds / Baths: 2 / 2.5

Check Availability for Ocean Cathedral Now!
 
Vacation Rental in Key West, FL
Oceanside
Condo
 Ocean Reflection - Oceanside

Rates starting at: $1500.00
Type: Condo
Sleeps: 6
Beds / Baths: 2 / 2

Check Availability for Ocean Reflection Now!
 
Vacation Rental in Key West, FL
Oceanside
Condo
 Oceanfront Oasis - Oceanside

Rates starting at: $1500.00
Type: Condo
Sleeps: 6
Beds / Baths: 3 / 2

Check Availability for Oceanfront Oasis Now!
 
Vacation Rental in Key West, FL
Oceanside
Condo
 Palm Oasis - Oceanside

Rates starting at: $1000.00
Type: Condo
Sleeps: 7
Beds / Baths: 3 / 2

Check Availability for Palm Oasis Now!
 
Vacation Rental in Key West, FL
Truman Annex
Condo
 Paradise on the Ocean - Truman Annex

Rates starting at: $2,400
Type: Condo
Sleeps: 5
Beds / Baths: 2 / 2.5

Check Availability for Paradise on the Ocean Now!
 
Vacation Rental in Key West, FL
Truman Annex
Condo
 Pipe the Side - Truman Annex

Rates starting at: $1600.00
Type: Condo
Sleeps: 4
Beds / Baths: 2 / 2.5

Check Availability for Pipe the Side Now!
 
Vacation Rental in Key West, FL
Truman Annex
Condo
 Pirates Trove - Truman Annex

Rates starting at: $3000.00
Type: Condo
Sleeps: 7
Beds / Baths: 3 / 3

Check Availability for Pirates Trove Now!
 
Vacation Rental in Key West, FL
Truman Annex
Townhome
 Queen Palm's Shade - Truman Annex

Rates starting at: $2000.00
Type: Townhome
Sleeps: 5
Beds / Baths: 2 / 2.5

Check Availability for Queen Palm's Shade Now!
 
Vacation Rental in Key West, FL
Truman Annex
Condo
 Saltwater Angler - Truman Annex

Rates starting at: $2400.00
Type: Condo
Sleeps: 5
Beds / Baths: 2 / 2.5

Check Availability for Saltwater Angler Now!
 
Vacation Rental in Key West, FL
Truman Annex
Condo
 Sol de Mar - Truman Annex

Rates starting at: $3500.00
Type: Condo
Sleeps: 8
Beds / Baths: 4 / 3.5

Check Availability for Sol de Mar Now!
 
Vacation Rental in Key West, FL
Truman Annex
Condo
 Sunset Dalite - Truman Annex

Rates starting at: $2400/wk
Type: Condo
Sleeps: 4
Beds / Baths: 2 / 2.5

Check Availability for Sunset Dalite Now!
 
Vacation Rental in Key West, FL
Truman Annex
Condo
 Tradewinds - Truman Annex

Rates starting at: $3000.00
Type: Condo
Sleeps: 7
Beds / Baths: 3 / 2

Check Availability for Tradewinds Now!
 
Vacation Rental in Key West, FL
Truman Annex
Condo
 Tropical Executive - Truman Annex

Rates starting at: $2400/wk
Type: Condo
Sleeps: 5
Beds / Baths: 2 / 2.5

Check Availability for Tropical Executive Now!
 
Vacation Rental in Key West, FL
Oceanside
Condo
 Tropical Splendor - Oceanside

Rates starting at: $1000.00
Type: Condo
Sleeps: 7
Beds / Baths: 3 / 2

Check Availability for Tropical Splendor Now!
 
Vacation Rental in Key West, FL
Truman Annex
Condo
 Window on the Sea - Truman Annex

Rates starting at: $2400/wk
Type: Condo
Sleeps: 5
Beds / Baths: 2 / 2

Check Availability for Window on the Sea Now!
 
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