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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 (888) 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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Weekly Key West Vacation Rentals

Found 110 Listings
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JUNE SPECIAL $3500/WEEK
Vacation Rental in Key West, FL
Truman Annex
Condo
Gulfstream Drift - Truman Annex

Rates starting at: $4300/week
Type: Condo
Sleeps: 7
Beds / Baths: 3 / 3

Check Availability for Gulfstream Drift Now!
 

Vacation Rental in Key West, FL
Truman Annex
Condo
Happy Hour Haven - Truman Annex

Rates starting at: $1,650/week
Type: Condo
Sleeps: 5
Beds / Baths: 2 / 2

Check Availability for Happy Hour Haven Now!
 

Vacation Rental in Key West, FL
Truman Annex
Condo
Havana Views - Truman Annex

Rates starting at: $1,450/week
Type: Condo
Sleeps: 4
Beds / Baths: 2 / 1

Check Availability for Havana Views Now!
 

Vacation Rental in Key West, FL
Coral Hammock
Townhome
Heavenly Haven - Coral Hammock

Rates starting at: $1800.00 wk
Type: Townhome
Sleeps: 6
Beds / Baths: 3 / 3

Check Availability for Heavenly Haven Now!
 

Vacation Rental in Key West, FL
Truman Annex
Condo
Hemingway's Hammock - Truman Annex

Rates starting at: $1,200/week
Type: Condo
Sleeps: 2
Beds / Baths: 1 / 1

Check Availability for Hemingway's Hammock Now!
 

Vacation Rental in Key West, FL
Truman Annex
Condo
Hibiscus Scents - Truman Annex

Rates starting at: $1,200/week
Type: Condo
Sleeps: 2
Beds / Baths: 1 / 1

Check Availability for Hibiscus Scents Now!
 

Vacation Rental in Key West, FL
Truman Annex
Townhome
High Tide - Truman Annex

Rates starting at: $1,800/week
Type: Townhome
Sleeps: 4
Beds / Baths: 2 / 1.5

Check Availability for High Tide Now!
 

NO MONTHLY RENTALS
Vacation Rental in Key West, FL
Truman Annex
Condo
Island Breezes - Truman Annex

Rates starting at: $1450/week
Type: Condo
Sleeps: 4
Beds / Baths: 2 / 1

Check Availability for Island Breezes Now!
 

Vacation Rental in Key West, FL
Truman Annex
Condo
Island Buoy - Truman Annex

Rates starting at: $1,450/week
Type: Condo
Sleeps: 4
Beds / Baths: 2 / 1

Check Availability for Island Buoy Now!
 

NO STAY MORE THAN 2 WEEKS
Vacation Rental in Key West, FL
Truman Annex
Condo
Island Spa - Truman Annex

Rates starting at: $1,200/week
Type: Condo
Sleeps: 2
Beds / Baths: 1 / 1

Check Availability for Island Spa Now!
 

Vacation Rental in Key West, FL
Truman Annex
Townhome
Ivory Coast - Truman Annex

Rates starting at: $1800.00 per week
Type: Townhome
Sleeps: 6
Beds / Baths: 2 / 1.5

Check Availability for Ivory Coast Now!
 

Vacation Rental in Key West, FL
Coral Hammock
Townhome
King Coral - Coral Hammock

Rates starting at: $250-$450 NIGHTLY
Type: Townhome
Sleeps: 4
Beds / Baths: 2 / 2.5

Check Availability for King Coral Now!
 

Vacation Rental in Key West, FL
Truman Annex
Townhome
La Mer - Truman Annex

Rates starting at: $2100.00/week
Type: Townhome
Sleeps: 6
Beds / Baths: 2 / 2.5

Check Availability for La Mer Now!
 

Vacation Rental in Key West, FL
Truman Annex
Townhome
Latitude Adjustment - Truman Annex

Rates starting at: $2100.00/week
Type: Townhome
Sleeps: 6
Beds / Baths: 2 / 2.5

Check Availability for Latitude Adjustment Now!
 

Vacation Rental in Key West, FL
Truman Annex
Townhome
License to Chill - Truman Annex

Rates starting at: $2100.00/week
Type: Townhome
Sleeps: 6
Beds / Baths: 2 / 2.5

Check Availability for License to Chill Now!
 

Vacation Rental in Key West, FL
Truman Annex
Condo
Low Tide - Truman Annex

Rates starting at: $1,450/week
Type: Condo
Sleeps: 4
Beds / Baths: 2 / 1

Check Availability for Low Tide Now!
 

Vacation Rental in Key West, FL
Truman Annex
Townhome
Mahogany Corner - Truman Annex

Rates starting at: $2100.00/week
Type: Townhome
Sleeps: 6
Beds / Baths: 2 / 2.5

Check Availability for Mahogany Corner Now!
 

Vacation Rental in Key West, FL
Truman Annex
Townhome
Manatee - Truman Annex

Rates starting at: $1,450/week
Type: Townhome
Sleeps: 4
Beds / Baths: 2 / 1

Check Availability for Manatee Now!
 

Vacation Rental in Key West, FL
Truman Annex
Townhome
Mangrove Snapper - Truman Annex

Rates starting at: $2050.00/week
Type: Townhome
Sleeps: 5
Beds / Baths: 2 / 2.5

Check Availability for Mangrove Snapper Now!
 

Vacation Rental in Key West, FL
Truman Annex
Condo
Marlin Blue - Truman Annex

Rates starting at: $1,200.00/week
Type: Condo
Sleeps: 2
Beds / Baths: 1 / 1

Check Availability for Marlin Blue Now!
 

Vacation Rental in Key West, FL
Truman Annex
Condo
Nautical Adventures - Truman Annex

Rates starting at: $2,900/week
Type: Condo
Sleeps: 4
Beds / Baths: 2 / 2.5

Check Availability for Nautical Adventures Now!
 

Vacation Rental in Key West, FL
Truman Annex
Condo
Ocean Breeze - Truman Annex

Rates starting at: $2900/week
Type: Condo
Sleeps: 5
Beds / Baths: 2 / 2.5

Check Availability for Ocean Breeze Now!
 

Vacation Rental in Key West, FL
Truman Annex
Condo
Oyster's Pearl - Truman Annex

Rates starting at: $1,200 per week
Type: Condo
Sleeps: 2
Beds / Baths: 1 / 1

Check Availability for Oyster's Pearl Now!
 

Vacation Rental in Key West, FL
Truman Annex
Condo
Paradise on the Ocean - Truman Annex

Rates starting at: $2,900/week
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
Paradise Poolside - Truman Annex

Rates starting at: $1650/week
Type: Condo
Sleeps: 4
Beds / Baths: 2 / 1.5

Check Availability for Paradise Poolside Now!
 

Vacation Rental in Key West, FL
Truman Annex
Townhome
Pelican's Perch - Truman Annex

Rates starting at: $1,950/week
Type: Townhome
Sleeps: 5
Beds / Baths: 2 / 2

Check Availability for Pelican's Perch Now!
 

Vacation Rental in Key West, FL
Truman Annex
Condo
Pirates Trove - Truman Annex

Rates starting at: $4,300.00
Type: Condo
Sleeps: 7
Beds / Baths: 3 / 3

Check Availability for Pirates Trove Now!
 

Vacation Rental in Key West, FL
Truman Annex
Townhome
Plato's Retreat - Truman Annex

Rates starting at: $2,050/week
Type: Townhome
Sleeps: 5
Beds / Baths: 2 / 2

Check Availability for Plato's Retreat Now!
 

Vacation Rental in Key West, FL
Truman Annex
Townhome
Poolside Hangover - Truman Annex

Rates starting at: $1,650/week
Type: Townhome
Sleeps: 4
Beds / Baths: 2 / 2

Check Availability for Poolside Hangover Now!
 

Vacation Rental in Key West, FL
Truman Annex
Condo
Rooster Haven - Truman Annex

Rates starting at: $1,450.00/week
Type: Condo
Sleeps: 4
Beds / Baths: 2 / 1

Check Availability for Rooster Haven Now!
 

Vacation Rental in Key West, FL
Truman Annex
Condo
Royal Poinciana - Truman Annex

Rates starting at: $1,200/week
Type: Condo
Sleeps: 2
Beds / Baths: 1 / 1

Check Availability for Royal Poinciana Now!
 

Vacation Rental in Key West, FL
Truman Annex
Townhome
Sago Palm - Truman Annex

Rates starting at: $1,950/week
Type: Townhome
Sleeps: 4
Beds / Baths: 2 / 2.5

Check Availability for Sago Palm Now!
 

Vacation Rental in Key West, FL
Truman Annex
Townhome
Sailor's Story - Truman Annex

Rates starting at: $1,950/week
Type: Townhome
Sleeps: 6
Beds / Baths: 2 / 2.5

Check Availability for Sailor's Story Now!
 

Vacation Rental in Key West, FL
Truman Annex
Condo
Saltwater Angler - Truman Annex

Rates starting at: $2,900.00/week
Type: Condo
Sleeps: 5
Beds / Baths: 2 / 2.5

Check Availability for Saltwater Angler Now!
 

Vacation Rental in Key West, FL
Truman Annex
Condo
Sand Crab Cabana - Truman Annex

Rates starting at: $1,200/week
Type: Condo
Sleeps: 2
Beds / Baths: 1 / 1

Check Availability for Sand Crab Cabana Now!
 

Vacation Rental in Key West, FL
Truman Annex
Condo
Seagull Lull - Truman Annex

Rates starting at: $1,200/week
Type: Condo
Sleeps: 2
Beds / Baths: 1 / 1

Check Availability for Seagull Lull Now!
 

Vacation Rental in Key West, FL
Truman Annex
Condo
Seascape - Truman Annex

Rates starting at: $1,450/week
Type: Condo
Sleeps: 4
Beds / Baths: 2 / 1

Check Availability for Seascape Now!
 

Vacation Rental in Key West, FL
Truman Annex
Townhome
Serenity Now - Truman Annex

Rates starting at: $2,050.00/week
Type: Townhome
Sleeps: 4
Beds / Baths: 2 / 2.5

Check Availability for Serenity Now Now!
 

Vacation Rental in Key West, FL
Truman Annex
Condo
Shady Nook - Truman Annex

Rates starting at: $1,450/week
Type: Condo
Sleeps: 4
Beds / Baths: 2 / 1

Check Availability for Shady Nook Now!
 

Vacation Rental in Key West, FL
Truman Annex
Townhome
South of the Palms - Truman Annex

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

Check Availability for South of the Palms Now!
 

Vacation Rental in Key West, FL
Truman Annex
Townhome
Southard Getaway - Truman Annex

Rates starting at: $1,800/week
Type: Townhome
Sleeps: 6
Beds / Baths: 2 / 1.5

Check Availability for Southard Getaway Now!
 

Vacation Rental in Key West, FL
Truman Annex
Condo
Southernmost Sanctuary - Truman Annex

Rates starting at: $1,450/week
Type: Condo
Sleeps: 4
Beds / Baths: 2 / 1

Check Availability for Southernmost Sanctuary Now!
 

Vacation Rental in Key West, FL
Truman Annex
Condo
Starshine Key West - Truman Annex

Rates starting at: $1,450/week
Type: Condo
Sleeps: 4
Beds / Baths: 2 / 1

Check Availability for Starshine Key West Now!
 

Vacation Rental in Key West, FL
Truman Annex
Condo
SUN,SEA, and SKY - Truman Annex

Rates starting at: $900.00/week
Type: Condo
Sleeps: 2
Beds / Baths: 1 / 1

Check Availability for SUN,SEA, and SKY Now!
 

Vacation Rental in Key West, FL
Truman Annex
Condo
Sunrise Cay - Truman Annex

Rates starting at: $1,200/week
Type: Condo
Sleeps: 2
Beds / Baths: 1 / 1

Check Availability for Sunrise Cay Now!
 

Vacation Rental in Key West, FL
Truman Annex
Townhome
Sunrise Cottage - Truman Annex

Rates starting at: $1950/week
Type: Townhome
Sleeps: 6
Beds / Baths: 2 / 2

Check Availability for Sunrise Cottage Now!
 

Vacation Rental in Key West, FL
Truman Annex
Condo
Sunset Dalite - Truman Annex

Rates starting at: $2,900/week
Type: Condo
Sleeps: 4
Beds / Baths: 2 / 2.5

Check Availability for Sunset Dalite Now!
 

Vacation Rental in Key West, FL
Truman Annex
Condo
Sunset Poolside - Truman Annex

Rates starting at: $1650/week
Type: Condo
Sleeps: 4
Beds / Baths: 2 / 2

Check Availability for Sunset Poolside Now!
 

Vacation Rental in Key West, FL
Truman Annex
Townhome
The Plantation - Truman Annex

Rates starting at: $3,100/week
Type: Townhome
Sleeps: 6
Beds / Baths: 3 / 3

Check Availability for The Plantation Now!
 

Vacation Rental in Key West, FL
Truman Annex
Townhome
Total Tranquility - Truman Annex

Rates starting at: $1,950/week
Type: Townhome
Sleeps: 6
Beds / Baths: 2 / 2.5

Check Availability for Total Tranquility Now!
 

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