Key West National Wildlife Refuge Rentals
From $605 per night (USD)VRBO
Seaport Proximity | Resort w\/ Outdoor Pools | Spacious Key West Room w\/ Balcony
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $605 per night (USD)VRBO
From $3665 per night (USD)VRBO
Spacious 2 BR Suite w\/ Living Area and Balcony | Onsite Parking Available
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $3665 per night (USD)VRBO
From $3513 per night (USD)VRBO
Two Bedrooms Family Suite with Balcony | Idyllic Resort w\/ Outdoor Pools
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $3513 per night (USD)VRBO
From $1242 per night (USD)VRBO
Waterfront Getaway | 2 Spacious Family Rooms w\/ Balcony | Old Town Best
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $1242 per night (USD)VRBO
From $1018 per night (USD)VRBO
**GARDEN OF EMMA @ THE ANNEX** Private Home & Pool + LAST KEY SERVICES…
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Tranquility. ...
From $1018 per night (USD)VRBO
From $379 per night (USD)Expedia
Royal Palm in Key West
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 5
End of Year Specials!There's no better way to experience island time - that slow shifting of hours that makes Key West s ...
From $379 per night (USD)Expedia
From $600 per night (USD)VRBO
Green Turtle Cottage KW 1 Block from Mile Marker 0 in Gated Truman Annex
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
This 2 bedroom 2.5 bath private home in a secluded section of the gated community of Truman Annex quietly sits among pre ...
From $600 per night (USD)VRBO
From $247 per night (USD)Expedia
Tropical cottage with private pool, two blocks from Duval - near Hemingway House
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
The Conch-Out Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $247 per night (USD)Expedia
From $1219 per night (USD)VRBO
Luxurious Gated Key West Oasis: 3 Bed + 4th Floor Sleeper, Elevator, & Golf Cart
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Immerse yourself in the heart of Old Town Key West and discover a luxurious retreat where island living meets modern com ...
From $1219 per night (USD)VRBO
From $950 per night (USD)Expedia
New! Coastal Rose - Bright Loft with High Ceilings!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Experience the charm of downtown Key West in this cozy 1-bedroom unit with an additional loft and a shared pool ...
From $950 per night (USD)Expedia
From $380 per night (USD)VRBO
New! Rose Petal Petite Suite - Pool & Parking!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Located in downtown Key West, the 'Rose Petal Petite Suite' offers a cozy and charming accommodation experience ...
From $380 per night (USD)VRBO
From $948 per night (USD)Expedia
New! Rose Key Cottage- Pool & Parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Escape to paradise with this luxurious Key West retreat, perfect for families and groups looking to unwind in s ...
From $948 per night (USD)Expedia
From $915 per night (USD)VRBO
An Ocean Serenity in Truman Annex, Key West
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
A luxury, ocean front, 2 bedroom, (king in master, queen in guest bedroom) 2.5 bath condo at Harbour Place in the award ...
From $915 per night (USD)VRBO
From $1043 per night (USD)VRBO
Romantic Stay in Historic Key West: 1BR Suite w\/ King Bed & Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Enjoy vibrant Key West: steps to Duval Street's nightlife, historic sites, and serene beaches. Perfect for culture and s ...
From $1043 per night (USD)VRBO
From $853 per night (USD)VRBO
Key West Paradise: Minimalist King Room w\/ Balcony or Terrace! Enjoy the Breeze
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Enjoy vibrant Key West: steps to Duval Street's nightlife, historic sites, and serene beaches. Perfect for culture and s ...
From $853 per night (USD)VRBO
From $873 per night (USD)VRBO
Stunning Key West Stay Perfect for a Romantic Escape! Outdoor Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Enjoy vibrant Key West: steps to Duval Street's nightlife, historic sites, and serene beaches. Perfect for culture and s ...
From $873 per night (USD)VRBO
From $800 per night (USD)VRBO
Stylish Boutique Room w\/ 2 Queen Beds - Access Pool & Poolside Bar
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Explore, dine, and relax in downtown Key West! We're steps from the Hemingway Home, Duval Street nightlife, and Southern ...
From $800 per night (USD)VRBO
From $2424 per night (USD)Expedia
NEW! The Rigby House - Pvt Pool, Amazing Location!
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 12
Summary: Escape to paradise with this stunning 6-bedroom, 6.5 bathroom home nestled in the heart of historic Key West. W ...
From $2424 per night (USD)Expedia
From $774 per night (USD)VRBO
NEW!!! UNDER RENOVATION!!! - Beacon Terrace in the Truman Annex Key West
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
"Beacon Terrace" at the Truman Annex is a beautifully renovated town home in the historic Foundry. The living area is th ...
From $774 per night (USD)VRBO
From $929 per night (USD)VRBO
Outstanding Room w\/ King Bed & Patio just steps from Duval St - Key West Bliss
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Explore, dine, and relax in downtown Key West! We're steps from the Hemingway Home, Duval Street nightlife, and Southern ...
From $929 per night (USD)VRBO
From $1097 per night (USD)VRBO
1BR Suite w\/ Spacious Living Area and Access to Heated Pool, Near Duval St
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
Explore, dine, and relax in downtown Key West! We're steps from the Hemingway Home, Duval Street nightlife, and Southern ...
From $1097 per night (USD)VRBO
From $890 per night (USD)VRBO
Welcoming 2 Queen Room w\/ Patio- Heart of Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Explore, dine, and relax in downtown Key West! We're steps from the Hemingway Home, Duval Street nightlife, and Southern ...
From $890 per night (USD)VRBO
From $826 per night (USD)VRBO
Room w\/ Queen Bed w\/ Patio in the Heart of Key West - Duval St steps away
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Explore, dine, and relax in downtown Key West! We're steps from the Hemingway Home, Duval Street nightlife, and Southern ...
From $826 per night (USD)VRBO
From $2557 per night (USD)VRBO
Stunning 2 Floor Loft in Vibrant Key West Ideal for Romantic Weekends - Pool
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
Explore, dine, and relax in downtown Key West! We're steps from the Hemingway Home, Duval Street nightlife, and Southern ...
From $2557 per night (USD)VRBO
From $1146 per night (USD)VRBO
Vibrant 2 Floor Loft Ideal for Relaxing Escape in Key West - Near Duval St
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Explore, dine, and relax in downtown Key West! We're steps from the Hemingway Home, Duval Street nightlife, and Southern ...
From $1146 per night (USD)VRBO
From $952 per night (USD)VRBO
Elegant Boutique Room w\/ Private Patio & Garden - Duval Street steps away
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Explore, dine, and relax in downtown Key West! We're steps from the Hemingway Home, Duval Street nightlife, and Southern ...
From $952 per night (USD)VRBO
From $1181 per night (USD)VRBO
𝐅𝐢𝐧𝐝𝐢𝐧𝐠𝐌𝐞𝐢𝐥𝐢 Near Duval Street, Waterfront Sunset Harbor Resort. 2BR
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to 𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢🌴 Experience Paradise at Hyatt Vacation Club at Sunset Harbor! 🌅 Nestled in the he ...
From $1181 per night (USD)VRBO
From $1101 per night (USD)VRBO
2 Family-friendly Units, Complimentary Breakfast, Outdoor Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Explore, dine, and relax in downtown Key West! We're steps from the Hemingway Home, Duval Street nightlife, and Southern ...
From $1101 per night (USD)VRBO
From $1883 per night (USD)VRBO
Perfect for Groups! 2 Pet-friendly Units, Free Breakfast, Outdoor Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Explore, dine, and relax in downtown Key West! We're steps from the Hemingway Home, Duval Street nightlife, and Southern ...
From $1883 per night (USD)VRBO
From $520 per night (USD)Expedia
**A BEACHY VIEW @ THE TRUMAN ANNEX IN KEY WEST**
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Come and relax in this 2-bedroom 1 bath, first floor with 3 flat screen TV's, custom kitchen, backyard tropical paradise ...
From $520 per night (USD)Expedia
From $2761 per night (USD)VRBO
3| Galleon | Marina | Spa | Hot Tub | Pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
The Galleon Resort is a premier destination in Key West, Florida, offering an unbeatable combination of luxury, comfort, ...
From $2761 per night (USD)VRBO
From $1207 per night (USD)VRBO
Sunset Harbor | Marina | Hot Tub | Pool | Concierge
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to your serene oasis in the heart of Key West’s iconic Old Town, where lush greenery and contemporary design cre ...
From $1207 per night (USD)VRBO
From $1234 per night (USD)VRBO
The Banyan | Concierge | Beach Access | Pool
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Located in the heart of historic Old Town Key West, The Banyan Resort is a charming escape set on a mid-1800s estate ste ...
From $1234 per night (USD)VRBO
From $2727 per night (USD)VRBO
Galleon | Hot Tub | Marina | Lux Resort | Concierge
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Galleon Resort is a premier destination in Key West, Florida, offering an unbeatable combination of luxury, comfort, ...
From $2727 per night (USD)VRBO
From $1502 per night (USD)VRBO
Sunset Harbor | Hyatt | Hot Tub | Pool | Marina | Lux Resort
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to your serene oasis in the heart of Key West’s iconic Old Town, where lush greenery and contemporary design cre ...
From $1502 per night (USD)VRBO
From $1009 per night (USD)VRBO
Galleon | Marina | Lux Resort | Pool | Hot Tub
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The Galleon Resort is a premier destination in Key West, Florida, offering an unbeatable combination of luxury, comfort, ...
From $1009 per night (USD)VRBO
From $2903 per night (USD)VRBO
Galleon | Marina | Concierge | Hot Tub | Spa
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Nestled along the sparkling Gulf of Mexico in historic Old Town, The Galleon Resort places you in the heart of Key West’ ...
From $2903 per night (USD)VRBO
From $1951 per night (USD)VRBO
Sunset Harbor | Hyatt | Marina | Concierge | Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your serene oasis in the heart of Key West’s iconic Old Town, where lush greenery and contemporary design cre ...
From $1951 per night (USD)VRBO
From $987 per night (USD)VRBO
𝐅𝐢𝐧𝐝𝐢𝐧𝐠𝐌𝐞𝐢𝐥𝐢 Near Duval Street, Waterfront Sunset Harbor Resort. 2BR
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to 𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢🌴 Experience Paradise at Hyatt Vacation Club at Sunset Harbor! 🌅 Nestled in the he ...
From $987 per night (USD)VRBO
From $1238 per night (USD)VRBO
𝐅𝐢𝐧𝐝𝐢𝐧𝐠𝐌𝐞𝐢𝐥𝐢 Near Duval Street, Waterfront Sunset Harbor Resort. 2BR
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to 𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢🌴 Experience Paradise at Hyatt Vacation Club at Sunset Harbor! 🌅 Nestled in the he ...
From $1238 per night (USD)VRBO
From $5625 per night (USD)VRBO
Key West Hyatt Charming 2-bedroom resort with WiFi, AC
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Experience a serene oasis nestled in the heart of Key West’s historic Old Town. Surrounded by lush greenery, this retrea ...
From $5625 per night (USD)VRBO
From $5625 per night (USD)VRBO
Key West Florida Charming 1-bedroom resort with WiFi, AC
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Experience a serene oasis nestled in the heart of Key West’s historic Old Town. Surrounded by lush greenery, this retrea ...
From $5625 per night (USD)VRBO
From $5625 per night (USD)VRBO
Key West Studio Charming resort with WiFi, AC, fitness room
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Experience a serene oasis nestled in the heart of Key West’s historic Old Town. Surrounded by lush greenery, this retrea ...
From $5625 per night (USD)VRBO
From $1614 per night (USD)Expedia
The Caroline House Estate - 1 Block off Duval & Key West Historic Seaport
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
This gorgeous classical Key West Estate property is quite possibly the most stylish blend of historic Victorian-Caribbea ...
From $1614 per night (USD)Expedia
From $1653 per night (USD)VRBO
No secrets at Pilar's Secret - Just a great location!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Pilar’s Secret is hidden away in the heart of Old Town Key West just half a block off the famous Duval Street. This secl ...
From $1653 per night (USD)VRBO
From $2001 per night (USD)VRBO
Key West, Galleon Resort, Marina, In Town, Pool, Hot Tub
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to The Galleon Resort in Key West, where paradise meets luxury at the southernmost tip of the United States. In ...
From $2001 per night (USD)VRBO
From $1374 per night (USD)VRBO
Sunset Harbor Resort & Spa, In Town, Marina, Hot Tub.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Discover this relaxing oasis in the heart of Key West's famed Old Town. Lush, verdant foliage surrounds the grounds and ...
From $1374 per night (USD)VRBO
From $1588 per night (USD)VRBO
Sunset Harbor Resort & Spa, Hot Tub, Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Discover this relaxing oasis in the heart of Key West's famed Old Town. Lush, verdant foliage surrounds the grounds and ...
From $1588 per night (USD)VRBO
From $986 per night (USD)VRBO
Sunset Harbor Resort, Marina, In Town, Hot Tub, Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover this relaxing oasis in the heart of Key West's famed Old Town. Lush, verdant foliage surrounds the grounds and ...
From $986 per night (USD)VRBO
From $599 per night (USD)Expedia
SWEET DREAMS ARE MADE OF 'THE KEYS' ~ Bahama Village 2 BR\/2 Ba Home w\/ Pool!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
BAHAMA VILLAGE BEAUTY... This dream of a home is yours for the ultimate escape to southernmost paradise! Located in the ...
From $599 per night (USD)Expedia
From $314 per night (USD)VRBO
THE NEST ~ Charming Conch Cottage Close to the Beach and Duval w\/ Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
HIDDEN GEM... The perfect location for guests who want to walk and bike to everything Key West has to offer. Modern cot ...
From $314 per night (USD)VRBO
From $282 per night (USD)Expedia
SWEET LIKE SUMMERTIME ~ 3 BR\/2Ba Home w\/ Pool and Yard!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
CLASSIC UPDATED CHARMER... Welcome to this beautifully renovated 3 bedroom 2 bath pool home, located in the heart of Bah ...
From $282 per night (USD)Expedia
From $1424 per night (USD)VRBO
Waterfront Sunset Harbor Resort Near Old Town+Amenities: 2BR FindingMeili
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to FindingMeili🌴 Experience Paradise at Hyatt Vacation Club at Sunset Harbor! An Additional Savings from $500 ...
From $1424 per night (USD)VRBO
From $476 per night (USD)Expedia
THE GOOD LIFE ~ Charming 2nd Floor 1 Bedroom, 1 Bath Truman Annex Condo!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
COZY VALUE IN TRUMAN ANNEX… This 2nd Floor one bedroom, one bath condo is located in The Shipyard, a neighborhood of the ...
From $476 per night (USD)Expedia
From $1016 per night (USD)VRBO
Craig & Cindy's 4 Bedroom Key West Truman Annex Porter House with private pool
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
The two story Truman Annex Porter House is the largest of our Key West properties and features 4 bedrooms and a private ...
From $1016 per night (USD)VRBO
From $1030 per night (USD)Expedia
JUST OFF DUVAL~ 2nd Floor Condo in Center of Duval St. with Parking Space!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
STEPS TO DUVAL ST… Take advantage of this premier opportunity to indulge in all your desired Key West bucket list items ...
From $1030 per night (USD)Expedia
From $1024 per night (USD)VRBO
Rose Lane Villas - Villa Aqua - 2 King Bedrooms - Downtown Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Nestled on a quiet lane in the heart of Old Town Key West, Rose Lane Villas is as close to the action as you'll get with ...
From $1024 per night (USD)VRBO
From $521 per night (USD)VRBO
Enjoy More Privacy in a Truman Annex End Unit Townhome
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Contact us about special Summer Rates! Absolute Best Location! Our Townhome is set in the tranquil verdant gardens of ...
From $521 per night (USD)VRBO
From $1133 per night (USD)VRBO
\"Tranquility \" At Ann Street Gardens Steps From Duval
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Location is ideal for this wonderful one bedroom retreat. A lush, inviting compound created so owners and guests could e ...
From $1133 per night (USD)VRBO
Click For PricingExpedia
Craig & Cindy Truman Annex Foundry Townhouse 2 bedrooms 2.5 baths
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Craig & Cindy Truman Annex Foundry Townhouse is a 2 bedroom 2 1/2 bath townhouse in the best location in all of Key West ...
Click For PricingExpedia
From $816 per night (USD)VRBO
Hyatt Sunset Harbor, overlooking the Gulf of Mexico.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
<p>Close to snorkeling, ecotours, and more, this smoke-free condo brings it all within reach. There's convenient onsite ...
From $816 per night (USD)VRBO
From $2064 per night (USD)Expedia
Location In Down Town Key West W\/ 2 Pools, Huge Private Roof Deck & Parking
- Bedrooms:
- 7
- Bathrooms:
- 7
- Sleeps:
- 16
Perfect location and great for entertaining! In the heart of Old Town Key West just steps from restaurants, bars, theate ...
From $2064 per night (USD)Expedia
From $432 per night (USD)VRBO
FOUNDRY 7- Weekly Vacation Rental - Shared Pool - 2BD\/2.5BA RealKeyWest
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 5
WELCOME TO FOUNDRY 7! Escape to the historic and luxurious neighborhood of Truman Annex in Key West, where you'll find ...
From $432 per night (USD)VRBO
From $370 per night (USD)Expedia
THE QUARTERDECK ~ Colorful & Comfy 2nd Floor 2Ba\/ 1Ba Unit in The Shipyard!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
COMFORT AND VALUE IN TRUMAN ANNEX… This newly renovated 2nd floor two bedroom condo is located in The Shipyard, a neighb ...
From $370 per night (USD)Expedia
From $2219 per night (USD)VRBO
STRIPES ~ Delightful Condo w\/Shared Pool in the Heart of Old Town Key West!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
When you don't need the entire compound but still want to enjoy this magnificent property in the heart of Old Town Key W ...
From $2219 per night (USD)VRBO
From $4270 per night (USD)Expedia
SOUTHERNMOST BELLE~ Heated Pool, Gourmet Kitchen & Elegant Large Bedrooms!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
LUXURY IN OLD TOWN... Grand home in the Historic Seaport area of Old Town Key West. Tucked behind a canopy of palms this ...
From $4270 per night (USD)Expedia
From $1950 per night (USD)VRBO
SAPODILLA HOUSE ~ Spectacular 3B\/3.5Ba Annex Home w\/Private Heated Pool!
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
PREMIER TROPICAL RETREAT... Come spoil yourself in this conveniently located two-story home tucked away on a quiet lane ...
From $1950 per night (USD)VRBO
From $1497 per night (USD)Expedia
STARS ~ 4 bedroom, 2 Bath Condo, Shared Heated Pool, Downtown Location!
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
When you do not need the entire compound but still want to enjoy this magnificent property in the heart of Old Town Key ...
From $1497 per night (USD)Expedia
From $1586 per night (USD)VRBO
PINEAPPLE COTTAGE: 2BR\/2BA-Pvt Pool -1\/2 block to Duval- RealKeyWest
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
WELCOME TO PINEAPPLE COTTAGE! The Pineapple Cottage is a charming two-bedroom, two-bathroom home located in Old Town K ...
From $1586 per night (USD)VRBO
From $409 per night (USD)VRBO
A Slice of Paradise! @ the Shipyard Palms!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
In the heart of Old Town, with the beautiful community of private homes and condominiums of Truman Annex, this Shipyard ...
From $409 per night (USD)VRBO
From $586 per night (USD)VRBO
Ann Street Cottage: A bright and airy home near Duval Street
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
Tucked away in an inviting compound you'll find the perfect hideaway called Ann Street Cottage; a charming one bedroom c ...
From $586 per night (USD)VRBO
From $746 per night (USD)Expedia
PALMS AWAY ~ Truman Annex Townhome with Outdoor Patio and Community Pool!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
STEPS TO IT ALL... Peaceful surroundings of swaying palm trees and picturesque white picket fences invite you in to this ...
From $746 per night (USD)Expedia
From $549 per night (USD)VRBO
Incredible 2BR Penthouse condo on Front Street with amazing amenities!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Galleon Resort is one of Key West's best resorts. Located on Front Street in front of the Marina, it has a large wat ...
From $549 per night (USD)VRBO
From $261 per night (USD)VRBO
Zen Cigar Maker Cottage, magical serpentine pool, serene landscaping, pkg\/bikes
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to the Key West Shire! A sublime sanctuary where all your worldly troubles melt away and relaxation is paramoun ...
From $261 per night (USD)VRBO
From $2068 per night (USD)VRBO
BAHAMA DREAMING ~ Incredibly Located 3 Bedroom, 2 Bath w\/ Private Pool!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
BEGIN YOUR ISLAND ESCAPE... Come get lost in the magic of this captivating island retreat offering modern amenities with ...
From $2068 per night (USD)VRBO
From $1406 per night (USD)VRBO
Secret Villa II @ Old Town: with Private Pool, close to Duval!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
- Secret Villa II - A Newly Renovated, Private Sanctuary, Centrally Located off of Duval Street with your very own pri ...
From $1406 per night (USD)VRBO
From $180 per night (USD)VRBO
PINEAPPLE COTTAGE ~ Adorable, Updated Cottage in Old Town with Heated Pool!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
RELAXED DOWNTOWN LIVING... Envelop yourself in true island living in this cute cottage just for the two of you. Located ...
From $180 per night (USD)VRBO
From $1224 per night (USD)VRBO
Secret Villa I @ Old Town with Private Pool, close to Duval!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
- Secret Villa I - A Newly Renovated, Private Sanctuary, Centrally Located off of Duval Street with your very own priv ...
From $1224 per night (USD)VRBO
From $1751 per night (USD)VRBO
Key West Suites Hotel # 205
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Key West Suites Hotel Welcome to your charming private studio apartment right on Duval street! Built in 1919, it used t ...
From $1751 per night (USD)VRBO
From $515 per night (USD)Expedia
SMOOTH SAILING ~ 2 Bedroom, 1 Bath Renovated Condo w\/ Community Pool!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
A TRUMAN ANNEX DREAM... Come discover this beautifully renovated condo within the desirable Shipyard neighborhood in the ...
From $515 per night (USD)Expedia
From $207 per night (USD)VRBO
BELLA VITA ~ 2\/1.5 located in the Truman Annex with a community pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
IDEAL LOCATION IN GREAT COMMUNITY... Enjoy your stay at the President's Walk at Truman Annex. This well manicured commu ...
From $207 per night (USD)VRBO
From $816 per night (USD)VRBO
Hyatt Sunset Harbor, overlooking the stunning and beautiful Gulf of Mexico.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
<p>A short distance from snorkeling, ecotours, and more, this smoke-free condo lets you experience it all. Duval Street ...
From $816 per night (USD)VRBO
From $356 per night (USD)VRBO
Minute walk to pool! 5 Star Preferred, 3 bikes, a pool, parking, and 2 porches!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
BIlly's Blue Heaven is fresh, clean and Pristine. We have updated the condo with all new paint, a new Smart Tv in the ...
From $356 per night (USD)VRBO
From $267 per night (USD)VRBO
Banyan Court downtown condo- 2 bedroom, 2.5 bath, walkable, parking, pool
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
AGE REQUIREMENT: Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their ...
From $267 per night (USD)VRBO
From $214 per night (USD)VRBO
Shipyard Truman Annex; 620 Thomas St. 1st Floor - AVAILABLE JULY & SEPT 2025
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
A Change In Latitudes is a non-smoking, 1st floor end unit in the serene section of Shipyard, Truman Annex. All the ame ...
From $214 per night (USD)VRBO
From $608 per night (USD)VRBO
** Waterfront - Two Blocks From Duval Street & Mallory Square**
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This condo located right on the water in Building 5 (Unit 531) - top floor - at the Hyatt Sunset Harbor, is a 2 bedroom, ...
From $608 per night (USD)VRBO
From $972 per night (USD)VRBO
★Family Friendly 2BR Condo at Heart of Old Town Key West- Sleeps 6!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Located in the heart of Old Town Key West. This resort overlooks the Gulf of Mexico with a private marina, private beach ...
From $972 per night (USD)VRBO
From $928 per night (USD)VRBO
Near Duval - Tiki Bar - Private Beach - 2BR Condo - Old Town Key West - Sleeps 6
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Located in the heart of Old Town Key West. This resort overlooks the Gulf of Mexico with a private marina, private beach ...
From $928 per night (USD)VRBO
From $540 per night (USD)VRBO
Galleon Resort & Marina available Feb8-15 2025
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
1 bed/1 bath overlooking Marina. King master bedroom. Sleeper sofa in living room. Jacuzzi tub in master bath with ceram ...
From $540 per night (USD)VRBO
From $870 per night (USD)Expedia
ISLE AZURE ~ Charming 3 Bed\/3 Bath with Private Pool in Truman Annex!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
QUINTESSENTIAL OLD TOWN CHARM… Imagine pulling up to a picture-perfect gated community, lined by white picket fences and ...
From $870 per night (USD)Expedia
From $1945 per night (USD)VRBO
Steps From Duval St. Historical Charm Meets Modern Design In Old Town Key West
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Perfectly located and fully remodeled, Octopus's Garden is steps from Duval Street and the home of Ernest Hemmingway. ...
From $1945 per night (USD)VRBO
From $4724 per night (USD)Expedia
STARS AND STRIPES ~ Magnificent Home Located In The Heart of Old Town!
- Bedrooms:
- 4
- Bathrooms:
- 9
- Sleeps:
- 20
ABUNDANCE IN OLD TOWN... Majestic home in the Historic Seaport area of Old Town Key West. This is THE house to bring eve ...
From $4724 per night (USD)Expedia
From $465 per night (USD)VRBO
Eleanor's Place in Key West Old Town - Dogs Ok with Parking.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
THE PROPERTY: "Eleanor's Place" has everything you might want on your monthly vacation to Key West, beginning with your ...
From $465 per night (USD)VRBO
From $338 per night (USD)VRBO
Lock-Out Unit at the Galleon Resort - Best Resort Location In KW
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Studio(lock-out) for rent 5th floor. The Galleon Resort has its own marina, fishing charters on-site, tiki bar that serv ...
From $338 per night (USD)VRBO
From $403 per night (USD)VRBO
Craig & Cindy Key West Truman Annex 2 bedroom 2 bath Shipyard Condo at MM 0!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Partial list of rental amenities at Craig & Cindy's Truman Annex Shipyard Condo includes: 2 bedrooms 2 bath {queen and ...
From $403 per night (USD)VRBO
From $344 per night (USD)Expedia
Craig & Cindy Key West Truman Annex Shipyard Condo with balcony at Mile Marker 0
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
Partial list of rental amenities at Craig & Cindy's Truman Annex Shipyard Condos include: 2 bedrooms 1 bath {queen and ...
From $344 per night (USD)Expedia
From $584 per night (USD)VRBO
TROPICAL FRONT ~ Remodeled 2 BR, 2.5 Ba w\/ Parking in Perfect Location!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
IN THE HEART OF IT ALL… A perfect location within a peaceful setting, this updated home allows for extraordinary moments ...
From $584 per night (USD)VRBO
From $704 per night (USD)Expedia
BLUE BUNGALOW ~ 2 Bedroom Townhome in Truman Annex Community with Pool!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
PICTURE PERFECT… Swaying palms and a picturesque white picket fence outline this tropical retreat luring you in to your ...
From $704 per night (USD)Expedia
Click For PricingVRBO
Penthouse Suite @ KW, Galleon Resort, Not Available in 2024-2025
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
The Galleon Resort is the best location - Old Town Key West, walking location to all the bars, many high quality restaur ...
Click For PricingVRBO
From $403 per night (USD)Expedia
Craig & Cindy Key West Truman Annex Shipyard Condo w\/ balcony at Mile Marker 0!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
Partial list of rental amenities at Craig & Cindy's Truman Annex Shipyard Condo includes: 2 bedrooms 1 bath {queen and ...
From $403 per night (USD)Expedia