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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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Monthly & Seasonal Key West Vacation Rentals

Found 125 Listings
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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!
 

SUMMER SPECIAL $1200/week
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
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
Key West Golf Club
Townhome
Spoonbill Retreat - Key West Golf Club

Rates starting at: $2400/MONTH
Type: Townhome
Sleeps: 4
Beds / Baths: 2 / 1.5

Check Availability for Spoonbill Retreat 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: $1,200.00
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
Key West Golf Club
Townhome
Sunrise on the Green - Key West Golf Club

Rates starting at: $3000 per month
Type: Townhome
Sleeps: 6
Beds / Baths: 3 / 2

Check Availability for Sunrise on the Green 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
Key West Golf Club
Townhome
Sunset Escape - Key West Golf Club

Rates starting at: $3500-$7000
Type: Townhome
Sleeps: 5
Beds / Baths: 3 / 3

Check Availability for Sunset Escape 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!
 

Please call for Summer Specials!
Vacation Rental in Key West, FL
Coral Hammock
Townhome
Treasure Trove - Coral Hammock

Rates starting at: $1600
Type: Townhome
Sleeps: 4
Beds / Baths: 2 / 2.5

Check Availability for Treasure Trove Now!
 

Vacation Rental in Key West, FL
Truman Annex
Private Home
Treehouse Island - Truman Annex

Rates starting at: $5000.00
Type: Private Home
Sleeps: 8
Beds / Baths: 3 / 4

Check Availability for Treehouse Island Now!
 

Vacation Rental in Key West, FL
Key West Golf Club
Townhome
Trophy Spot - Key West Golf Club

Rates starting at: $2400 per month
Type: Townhome
Sleeps: 4
Beds / Baths: 2 / 2

Check Availability for Trophy Spot Now!
 

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

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

Check Availability for Tropical Angler Now!
 

Vacation Rental in Key West, FL
Truman Annex
Townhome
Tropical Delight - Truman Annex

Rates starting at: $1,950.00/week
Type: Townhome
Sleeps: 6
Beds / Baths: 2 / 2.5

Check Availability for Tropical Delight Now!
 

Vacation Rental in Key West, FL
Truman Annex
Condo
Tropical Executive - Truman Annex

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

Check Availability for Tropical Executive Now!
 

Vacation Rental in Key West, FL
Truman Annex
Condo
Tropical Poolview - Truman Annex

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

Check Availability for Tropical Poolview Now!
 

Vacation Rental in Key West, FL
Truman Annex
Condo
Tropical Vineyard - Truman Annex

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

Check Availability for Tropical Vineyard Now!
 

Vacation Rental in Key West, FL
Truman Annex
Townhome
Villa Luna - Truman Annex

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

Check Availability for Villa Luna Now!
 

Vacation Rental in Key West, FL
Key West Golf Club
Townhome
Where The Sidewalk Ends - Key West Golf Club

Rates starting at: $2400-$5200
Type: Townhome
Sleeps: 4
Beds / Baths: 2 / 2.5

Check Availability for Where The Sidewalk Ends Now!
 

Vacation Rental in Key West, FL
Truman Annex
Condo
Window on the Sea - Truman Annex

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

Check Availability for Window on the Sea Now!
 

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