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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 134 Listings
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Vacation Rental in Key West, FL
Key West Golf Club
Townhome
A Casa de Mare - Key West Golf Club

Rates starting at: $2400-$5000
Type: Townhome
Sleeps: 4
Beds / Baths: 2 / 1.5

Check Availability for A Casa de Mare Now!
 

Vacation Rental in Key West, FL
Key West Golf Club
Townhome
A Chandelier House - Key West Golf Club

Rates starting at: $2400-$5000
Type: Townhome
Sleeps: 4
Beds / Baths: 2 / 1

Check Availability for A Chandelier House Now!
 

Vacation Rental in Key West, FL
Truman Annex
Condo
A CHANGE IN LATITUDES - Truman Annex

Rates starting at: $4350
Type: Condo
Sleeps: 4
Beds / Baths: 2 / 1

Check Availability for A CHANGE IN LATITUDES Now!
 

Vacation Rental in Key West, FL
Key West Golf Club
Townhome
A Garden Escape - Key West Golf Club

Rates starting at: $2300-$5000
Type: Townhome
Sleeps: 4
Beds / Baths: 2 / 1.5

Check Availability for A Garden Escape Now!
 

Call for April Special
Vacation Rental in Key West, FL
Truman Annex
Condo
A Hondurosa South - Truman Annex

Rates starting at: $2,600/week
Type: Condo
Sleeps: 5
Beds / Baths: 2 / 2

Check Availability for A Hondurosa South Now!
 

Vacation Rental in Key West, FL
Key West Golf Club
Townhome
A Palm Tree Paradise - Key West Golf Club

Rates starting at: $2300-$5000
Type: Townhome
Sleeps: 4
Beds / Baths: 2 / 1.5

Check Availability for A Palm Tree Paradise Now!
 

Vacation Rental in Key West, FL
Key West Golf Club
Private Home
A Place To Rest - Key West Golf Club

Rates starting at: $3500-$7500
Type: Private Home
Sleeps: 6
Beds / Baths: 3 / 2

Check Availability for A Place To Rest Now!
 

Vacation Rental in Key West, FL
Key West Golf Club
Private Home
A Sanctuary Home - Key West Golf Club

Rates starting at: $4000
Type: Private Home
Sleeps: 6
Beds / Baths: 3 / 2.5

Check Availability for A Sanctuary Home Now!
 

Vacation Rental in Key West, FL
Key West Golf Club
Townhome
A Slice of Heaven - Key West Golf Club

Rates starting at: $2300-$5000
Type: Townhome
Sleeps: 4
Beds / Baths: 2 / 1.5

Check Availability for A Slice of Heaven Now!
 

Vacation Rental in Key West, FL
Truman Annex
Condo
A Sunset and Harbor View - Truman Annex

Rates starting at: 4300/week
Type: Condo
Sleeps: 6
Beds / Baths: 3 / 3

Check Availability for A Sunset and Harbor View Now!
 

Vacation Rental in Key West, FL
Truman Annex
Private Home
A Sunset Breeze - Truman Annex

Rates starting at: $4,000/week
Type: Private Home
Sleeps: 7
Beds / Baths: 3 / 2.5

Check Availability for A Sunset Breeze Now!
 

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

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

Check Availability for A Sunset View Now!
 

Vacation Rental in Key West, FL
Truman Annex
Townhome
Aah Paradise - Truman Annex

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

Check Availability for Aah Paradise Now!
 

Vacation Rental in Key West, FL
Truman Annex
Townhome
Admiral's Gold - Truman Annex

Rates starting at: $4000/week
Type: Townhome
Sleeps: 8
Beds / Baths: 4 / 3.5

Check Availability for Admiral's Gold Now!
 

Vacation Rental in Key West, FL
Truman Annex
Private Home
Admiral's Paradise - Truman Annex

Rates starting at: $5,000/week
Type: Private Home
Sleeps: 6
Beds / Baths: 3 / 3.5

Check Availability for Admiral's Paradise Now!
 

Vacation Rental in Key West, FL
Truman Annex
Private Home
Admiral's Treasure - Truman Annex

Rates starting at: $6300.00/week
Type: Private Home
Sleeps: 8
Beds / Baths: 4 / 4

Check Availability for Admiral's Treasure Now!
 

Vacation Rental in Key West, FL
Truman Annex
Private Home
Admirals Quarters - Truman Annex

Rates starting at: $15,000/monthly
Type: Private Home
Sleeps: 8
Beds / Baths: 4 / 4

Check Availability for Admirals Quarters Now!
 

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

Rates starting at: $2,100/week
Type: Townhome
Sleeps: 6
Beds / Baths: 2 / 2.5

Check Availability for Alegre Now!
 

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

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

Check Availability for Alhambra Now!
 

Vacation Rental in Key West, FL
Key West Golf Club
Townhome
Almost Heaven - Key West Golf Club

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

Check Availability for Almost Heaven Now!
 

Vacation Rental in Key West, FL
Truman Annex
Condo
Almost Paradise - Truman Annex

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

Check Availability for Almost Paradise Now!
 

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

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

Check Availability for Amberjack Now!
 

Vacation Rental in Key West, FL
Truman Annex
Townhome
Angel Fish - Truman Annex

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

Check Availability for Angel Fish Now!
 

Vacation Rental in Key West, FL
Truman Annex
Condo
Angler's Retreat - Truman Annex

Rates starting at: $1450.00/week
Type: Condo
Sleeps: 4
Beds / Baths: 2 / 1

Check Availability for Angler's Retreat Now!
 

Vacation Rental in Key West, FL
Truman Annex
Condo
Annie's Hideaway - Truman Annex

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

Check Availability for Annie's Hideaway Now!
 

Vacation Rental in Key West, FL
Truman Annex
Condo
Another Day in Paradise - Truman Annex

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

Check Availability for Another Day in Paradise Now!
 

Vacation Rental in Key West, FL
Truman Annex
Condo
Another Three Hour Tour - Truman Annex

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

Check Availability for Another Three Hour Tour Now!
 

Vacation Rental in Key West, FL
Truman Annex
Condo
Aqua Oasis - Truman Annex

Rates starting at: $1450.00
Type: Condo
Sleeps: 4
Beds / Baths: 2 / 1

Check Availability for Aqua Oasis Now!
 

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

Rates starting at: $3,900
Type: Townhome
Sleeps: 12
Beds / Baths: 4 / 4.5

Check Availability for ARCHIPELAGO Now!
 

Vacation Rental in Key West, FL
Truman Annex
Townhome
ARCHIPELAGO l - Truman Annex

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

Check Availability for ARCHIPELAGO l Now!
 

Vacation Rental in Key West, FL
Truman Annex
Townhome
ARCHIPELAGO ll - Truman Annex

Rates starting at: $1950.00
Type: Townhome
Sleeps: 6
Beds / Baths: 2 / 2.5

Check Availability for ARCHIPELAGO ll Now!
 

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

Rates starting at: $1450.00
Type: Condo
Sleeps: 4
Beds / Baths: 2 / 1

Check Availability for Arosa Now!
 

Vacation Rental in Key West, FL
Truman Annex
Condo
At Worlds End - Truman Annex

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

Check Availability for At Worlds End Now!
 

Vacation Rental in Key West, FL
Key West Golf Club
Townhome
Azalea Isle - Key West Golf Club

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

Check Availability for Azalea Isle Now!
 

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

Rates starting at: $2,400/week
Type: Condo
Sleeps: 4
Beds / Baths: 2 / 2

Check Availability for Banana Key Now!
 

Vacation Rental in Key West, FL
Truman Annex
Townhome
Bay Breeze - Truman Annex

Rates starting at: $2,100/week
Type: Townhome
Sleeps: 6
Beds / Baths: 2 / 2.5

Check Availability for Bay Breeze Now!
 

Vacation Rental in Key West, FL
Truman Annex
Condo
Bayview Harbor - Truman Annex

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

Check Availability for Bayview Harbor Now!
 

Vacation Rental in Key West, FL
Truman Annex
Condo
Bird of Paradise - Truman Annex

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

Check Availability for Bird of Paradise Now!
 

Vacation Rental in Key West, FL
Truman Annex
Townhome
Blue Lagoon - Truman Annex

Rates starting at: $3,100/week
Type: Townhome
Sleeps: 8
Beds / Baths: 3 / 2

Check Availability for Blue Lagoon Now!
 

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

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

Check Availability for Blue Ocean Now!
 

Unique old town living, inquire for summer rate specials
Vacation Rental in Key West, FL
Old Town
Unique Property
Blue on White - Old Town

Rates starting at: $2000/$2500--Monthly Only
Type: Unique Property
Sleeps: 2
Beds / Baths: 1 / 1

Check Availability for Blue on White Now!
 

Vacation Rental in Key West, FL
Truman Annex
Private Home
Blume'n Paradise - Truman Annex

Rates starting at: $7,000/Week
Type: Private Home
Sleeps: 8
Beds / Baths: 4 / 4

Check Availability for Blume'n Paradise Now!
 

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

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

Check Availability for Cabana Breeze Now!
 

Vacation Rental in Key West, FL
Truman Annex
Townhome
Captains Wheel - Truman Annex

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

Check Availability for Captains Wheel Now!
 

Vacation Rental in Key West, FL
Truman Annex
Condo
Catch of the Day - Truman Annex

Rates starting at: $4300/week
Type: Condo
Sleeps: 7
Beds / Baths: 3 / 2.5

Check Availability for Catch of the Day Now!
 

Vacation Rental in Key West, FL
Truman Annex
Condo
Chilmark South - Truman Annex

Rates starting at: $2,900/wk
Type: Condo
Sleeps: 5
Beds / Baths: 2 / 2

Check Availability for Chilmark South Now!
 

Vacation Rental in Key West, FL
Truman Annex
Townhome
Coconut Bay - Truman Annex

Rates starting at: $2,100/week
Type: Townhome
Sleeps: 6
Beds / Baths: 2 / 2.5

Check Availability for Coconut Bay Now!
 

Vacation Rental in Key West, FL
Truman Annex
Townhome
Colorful Cocktail - Truman Annex

Rates starting at: $1950.00
Type: Townhome
Sleeps: 6
Beds / Baths: 2 / 2

Check Availability for Colorful Cocktail Now!
 

Vacation Rental in Key West, FL
Truman Annex
Condo
Conch Shell Isle - Truman Annex

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

Check Availability for Conch Shell Isle Now!
 

Vacation Rental in Key West, FL
Truman Annex
Condo
Cool Citrus - Truman Annex

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

Check Availability for Cool Citrus Now!
 

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