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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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Monthly & Seasonal Key West Vacation Rentals
Found 177 Listings
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Vacation Rental in Key West, FL
Truman Annex
Private Home
 27 Palms - Truman Annex

Rates starting at: $4500
Type: Private Home
Sleeps: 6
Beds / Baths: 3 / 4

Check Availability for 27 Palms Now!
 
Vacation Rental in Key West, FL
Truman Annex
Private Home
 A Mermaid's Rock - Truman Annex

Rates starting at: $4,000/week
Type: Private Home
Sleeps: 8
Beds / Baths: 4 / 3

Check Availability for A Mermaid's Rock Now!
 
Vacation Rental in Key West, FL
Truman Annex
Condo
 A Southern Exposure - Truman Annex

Rates starting at: $1,200
Type: Condo
Sleeps: 4
Beds / Baths: 2 / 1

Check Availability for A Southern Exposure Now!
 
SUMMER SPECIAL $1100.00 WEEK APR TO NOV EXCLUDING SPECIAL EVENTS
Vacation Rental in Key West, FL
Truman Annex
Condo
 A Sunset View - Truman Annex

Rates starting at: $1,200/week
Type: Condo
Sleeps: 4
Beds / Baths: 2 / 1

Check Availability for A Sunset View Now!
 
Vacation Rental in Key West, FL
Truman Annex
Condo
 Abbott - Truman Annex

Rates starting at: $1,200 per week
Type: Condo
Sleeps: 4
Beds / Baths: 2 / 1

Check Availability for Abbott Now!
 
Vacation Rental in Key West, FL
Truman Annex
Townhome
 Admiral's Gold - Truman Annex

Rates starting at: $4,000/week
Type: Townhome
Sleeps: 10
Beds / Baths: 4 / 3.5

Check Availability for Admiral's Gold Now!
 
Vacation Rental in Key West, FL
Truman Annex
Townhome
 Admiral's Key - Truman Annex

Rates starting at: $1,600/week
Type: Townhome
Sleeps: 6
Beds / Baths: 2 / 2.5

Check Availability for Admiral's Key Now!
 
SUMMER SPECIAL $3750.00 PER WEEK
Vacation Rental in Key West, FL
Truman Annex
Private Home
 Admiral's Paradise - Truman Annex

Rates starting at: $4,500/week
Type: Private Home
Sleeps: 6
Beds / Baths: 3 / 3.5

Check Availability for Admiral's Paradise Now!
 
JUNE THRU MID OCTOBER $4,500 per week
Vacation Rental in Key West, FL
Truman Annex
Private Home
 Admiral's Treasure - Truman Annex

Rates starting at: $6000.00/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
Condo
 Alhambra - Truman Annex

Rates starting at: $1,000/week
Type: Condo
Sleeps: 4
Beds / Baths: 1 / 1

Check Availability for Alhambra Now!
 
Vacation Rental in Key West, FL
Truman Annex
Condo
 Almost Paradise - Truman Annex

Rates starting at: $1200
Type: Condo
Sleeps: 4
Beds / Baths: 2 / 1

Check Availability for Almost Paradise Now!
 
Vacation Rental in Key West, FL
Truman Annex
Townhome
 Angel Fish - Truman Annex

Rates starting at: $1,600/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: $1200.00/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
 Arosa - Truman Annex

Rates starting at: $1200.00
Type: Condo
Sleeps: 4
Beds / Baths: 2 / 1

Check Availability for Arosa Now!
 
Call for Summer special rates!!
Vacation Rental in Key West, FL
Bahama Village
Unique Property
 Bahama Mama - Bahama Village

Rates starting at: $4000.00/month
Type: Unique Property
Sleeps: 6
Beds / Baths: 3 / 2

Check Availability for Bahama Mama Now!
 
Vacation Rental in Key West, FL
Truman Annex
Condo
 Bamboo Cabana - Truman Annex

Rates starting at: $1200.00
Type: Condo
Sleeps: 4
Beds / Baths: 2 / 1

Check Availability for Bamboo Cabana Now!
 
Vacation Rental in Key West, FL
Truman Annex
Condo
 Bamboo Dreams - Truman Annex

Rates starting at: $1,200/week
Type: Condo
Sleeps: 4
Beds / Baths: 2 / 1

Check Availability for Bamboo Dreams Now!
 
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
 Banana Key - Truman Annex

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

Check Availability for Banana Key Now!
 
Vacation Rental in Key West, FL
Truman Annex
Condo
 Bayview Harbor - Truman Annex

Rates starting at: $1,200/week
Type: Condo
Sleeps: 4
Beds / Baths: 2 / 1

Check Availability for Bayview Harbor Now!
 
Vacation Rental in Key West, FL
Truman Annex
Private Home
 Big Bamboo - Truman Annex

Rates starting at: $3,500.00
Type: Private Home
Sleeps: 8
Beds / Baths: 3 / 3

Check Availability for Big Bamboo Now!
 
Vacation Rental in Key West, FL
Truman Annex
Townhome
 Bikinis in Paradise - Truman Annex

Rates starting at: $1,600
Type: Townhome
Sleeps: 4
Beds / Baths: 2 / 2.5

Check Availability for Bikinis in Paradise Now!
 
Vacation Rental in Key West, FL
Truman Annex
Condo
 Bird of Paradise - Truman Annex

Rates starting at: $1,400/week
Type: Condo
Sleeps: 4
Beds / Baths: 2 / 2

Check Availability for Bird of Paradise Now!
 
Vacation Rental in Key West, FL
Key West Golf Club
Townhome
 Blue Heron Hacienda - Key West Golf Club

Rates starting at: $1800 per month
Type: Townhome
Sleeps: 4
Beds / Baths: 2 / 1.5

Check Availability for Blue Heron Hacienda Now!
 
Vacation Rental in Key West, FL
Truman Annex
Townhome
 Blue Lagoon - Truman Annex

Rates starting at: $2,500/week
Type: Townhome
Sleeps: 8
Beds / Baths: 3 / 2

Check Availability for Blue Lagoon Now!
 
SUMMER SPECIAL $4500.00 PER WEEK
Vacation Rental in Key West, FL
Truman Annex
Private Home
 Blume'n Paradise - Truman Annex

Rates starting at: $5500.00/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
Townhome
 Bougainvillea Vines - Truman Annex

Rates starting at: $1,800/week
Type: Townhome
Sleeps: 6
Beds / Baths: 2 / 2.5

Check Availability for Bougainvillea Vines Now!
 
Vacation Rental in Key West, FL
Truman Annex
Townhome
 Brubeck Cottage - Truman Annex

Rates starting at: $1500.00/week
Type: Townhome
Sleeps: 6
Beds / Baths: 2 / 2.5

Check Availability for Brubeck Cottage Now!
 
Vacation Rental in Key West, FL
Truman Annex
Condo
 Cabana Breeze - Truman Annex

Rates starting at: $1200.00 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: $1,600.00/week
Type: Townhome
Sleeps: 6
Beds / Baths: 2 / 2.5

Check Availability for Captains Wheel Now!
 
Vacation Rental in Key West, FL
Truman Annex
Townhome
 Caribe - Truman Annex

Rates starting at: $1,200/week
Type: Townhome
Sleeps: 4
Beds / Baths: 2 / 1

Check Availability for Caribe Now!
 
Vacation Rental in Key West, FL
Key West Golf Club
Townhome
 Casablanca - Key West Golf Club

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

Check Availability for Casablanca 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!
 
Vacation Rental in Key West, FL
Truman Annex
Townhome
 Cayo Hueso Casa - Truman Annex

Rates starting at: $1,600 per week
Type: Townhome
Sleeps: 4
Beds / Baths: 2 / 2.5

Check Availability for Cayo Hueso Casa 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
Townhome
 Coconut Bay - Truman Annex

Rates starting at: $1,800.00/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
 Coconut Palm - Truman Annex

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

Check Availability for Coconut Palm Now!
 
Vacation Rental in Key West, FL
Truman Annex
Townhome
 Colorful Cocktail - Truman Annex

Rates starting at: $1600.00
Type: Townhome
Sleeps: 6
Beds / Baths: 2 / 2

Check Availability for Colorful Cocktail Now!
 
Vacation Rental in Key West, FL
Truman Annex
Townhome
 Colors of Paradise - Truman Annex

Rates starting at: $1800/wk
Type: Townhome
Sleeps: 6
Beds / Baths: 2 / 2.5

Check Availability for Colors of Paradise Now!
 
Vacation Rental in Key West, FL
Truman Annex
Condo
 Conch Retreat - Truman Annex

Rates starting at: $1,200/week
Type: Condo
Sleeps: 4
Beds / Baths: 2 / 1

Check Availability for Conch Retreat Now!
 
Summer special rate $1000 per week May thru Sept
Vacation Rental in Key West, FL
Truman Annex
Condo
 Conch Shell Isle - Truman Annex

Rates starting at: $1,100/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: $1,200/week
Type: Condo
Sleeps: 4
Beds / Baths: 2 / 1

Check Availability for Cool Citrus Now!
 
Vacation Rental in Key West, FL
Coral Hammock
Townhome
 Coral Isle - Coral Hammock

Rates starting at: $1000.00/week
Type: Townhome
Sleeps: 6
Beds / Baths: 3 / 3

Check Availability for Coral Isle Now!
 
Vacation Rental in Key West, FL
Truman Annex
Townhome
 Crown Jewel - Truman Annex

Rates starting at: $1,800/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
 Dinner is Poured - Truman Annex

Rates starting at: $1,200/week
Type: Condo
Sleeps: 4
Beds / Baths: 2 / 1

Check Availability for Dinner is Poured Now!
 
Vacation Rental in Key West, FL
Truman Annex
Condo
 Dolphin Delight - Truman Annex

Rates starting at: $1,200/week
Type: Condo
Sleeps: 4
Beds / Baths: 2 / 1

Check Availability for Dolphin Delight Now!
 
Vacation Rental in Key West, FL
Truman Annex
Condo
 Dolphin Suite - Truman Annex

Rates starting at: $1200.00
Type: Condo
Sleeps: 4
Beds / Baths: 2 / 1

Check Availability for Dolphin Suite 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
Townhome
 Emerald Sea - Truman Annex

Rates starting at: $1,400/week
Type: Townhome
Sleeps: 6
Beds / Baths: 2 / 1.5

Check Availability for Emerald Sea Now!
 
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