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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 122 Listings
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Vacation Rental in Key West, FL
Truman Annex
Townhome
Crown Jewel - Truman Annex

Rates starting at: $2,100/week
Type: Townhome
Sleeps: 4
Beds / Baths: 2 / 2.5

Check Availability for Crown Jewel Now!
 

Vacation Rental in Key West, FL
Truman Annex
Condo
Dolphin Delight - Truman Annex

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

Check Availability for Dolphin Delight Now!
 

Ask About fantasy Fest Special!
Vacation Rental in Key West, FL
Truman Annex
Private Home
Dolphin Watch - Truman Annex

Rates starting at: $5,000/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: $2,900/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
Flamingo Beach - Truman Annex

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

Check Availability for Flamingo Beach Now!
 

Vacation Rental in Key West, FL
Truman Annex
Condo
Flip Flop In - Truman Annex

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

Check Availability for Flip Flop In Now!
 

CALL FOR FANTASY FEST SPECIAL!!
Vacation Rental in Key West, FL
Truman Annex
Condo
Forever Young - Truman Annex

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

Check Availability for Forever Young Now!
 

Vacation Rental in Key West, FL
Truman Annex
Townhome
Fun in the Sun - Truman Annex

Rates starting at: $1,950.00/week
Type: Townhome
Sleeps: 5
Beds / Baths: 2 / 2.5

Check Availability for Fun in the Sun Now!
 

CALL FOR FANTASY FEST SPECIAL!!
Vacation Rental in Key West, FL
Truman Annex
Condo
Grandview Terrace - Truman Annex

Rates starting at: $4,300/week
Type: Condo
Sleeps: 5
Beds / Baths: 2 / 2

Check Availability for Grandview Terrace Now!
 

Vacation Rental in Key West, FL
Truman Annex
Townhome
Green Bamboo in the Truman Annex - Truman Annex

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

Check Availability for Green Bamboo in the Truman Annex Now!
 

Vacation Rental in Key West, FL
Truman Annex
Condo
Green Spot - Truman Annex

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

Check Availability for Green Spot Now!
 

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!
 

Vacation Rental in Key West, FL
Old Town
Private Home
Holiday Haven - Old Town

Rates starting at: $3500/month
Type: Private Home
Sleeps: 2
Beds / Baths: 2 / 2

Check Availability for Holiday Haven 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!
 

CALL FOR FANTASY FEST SPECIAL!!
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
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
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
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
Key West Golf Club
Townhome
Mermaid Manor - Key West Golf Club

Rates starting at: MONTHLY STARTING AT $2400
Type: Townhome
Sleeps: 4
Beds / Baths: 2 / 2.5

Check Availability for Mermaid Manor 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!
 

CALL FOR FANTASY FEST SPECIAL!!
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
Key West Golf Club
Townhome
Paradise Key - Key West Golf Club

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

Check Availability for Paradise Key Now!
 

CALL FOR FANTASY FEST SPECIAL!!
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
Key West Golf Club
Townhome
Paradise Palm - Key West Golf Club

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

Check Availability for Paradise Palm 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!
 

CALL FOR FANTASY FEST SPECIAL!!
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!
 

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