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From $2324 per night (USD)
VRBO
Key West Oasis - Truman Annex Estate
Bedrooms:
5
Bathrooms:
5
Sleeps:
8
Welcome to Key West Oasis! This beautiful and sophisticated estate checks all the boxes and is located on one of the mos ...
From $2324 per night (USD)
VRBO
$Modern 2BR Condo Old Town\/Balcony & Pool$
From $194 per night (USD)
Expedia
Modern 2BR Condo Old Town\/Balcony & Pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
*28 day min stay* Come enjoy this fully updated 2/BR condo in the heart of Old Town. The perfect balance of being close ...
From $194 per night (USD)
Expedia
$Green Goddess - 4 BD\/3 BA Amazing 360 Degree Rooftop Views! RealKeyWest$
From $397 per night (USD)
VRBO
Green Goddess - 4 BD\/3 BA Amazing 360 Degree Rooftop Views! RealKeyWest
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Experience the beauty of Key West's famous sunsets from the comfort of your own vacation home at The Green Goddess. This ...
From $397 per night (USD)
VRBO
From $197 per night (USD)
Expedia
Private Parking & Near Downtown - Lil' Bit
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: - "Lil Bit" is a rare find in the historic Bahama Village neighborhood. - This classic "conch" home is modern ...
From $197 per night (USD)
Expedia
From $757 per night (USD)
VRBO
Balcony & Near Downtown - Sky Suite on Duval
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Summary: Welcome to Sky Suite On Duval Street - a newly remodeled masterpiece that overlooks world famous Duval Street. ...
From $757 per night (USD)
VRBO
From $1330 per night (USD)
Expedia
**ENDLESS SUMMER @ OLD TOWN** New Villa & Pool + LAST KEY SERVICES...
Bedrooms:
5
Bathrooms:
5
Sleeps:
12
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! All year long ...
From $1330 per night (USD)
Expedia
From $730 per night (USD)
VRBO
Historic Old Town Key West Cigarmaker's Cottage - Cigar House, Sleeps 4
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
OVERVIEW The Cigar House is a 100+ year old “Cigar maker’s house”. The recently completely renovated house is charming, ...
From $730 per night (USD)
VRBO
From $716 per night (USD)
Expedia
Balcony on Duval - Duval Dream Loft
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Summary: Located right in the heart of the World Famous Duval Street, enjoy a true downtown Key West experience! This un ...
From $716 per night (USD)
Expedia
From $673 per night (USD)
VRBO
Balcony on Duval - The Collins on Duval
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Summary: Located right in the heart of the World Famous Duval Street, enjoy a true downtown Key West experience! The Col ...
From $673 per night (USD)
VRBO
From $730 per night (USD)
Expedia
Historic Old Town Key West Cigarmaker's Cottage - Conch House, Sleeps 5
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
The Conch House is a 100+ year old “Cigarmaker’s house. The house is recently renovated, charming, spacious, secluded a ...
From $730 per night (USD)
Expedia
$Fairway Villa w\/ Private Pool$
From $332 per night (USD)
VRBO
Fairway Villa w\/ Private Pool
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Welcome to Fairway Villa a beautiful large 3 bedroom, 3 bathroom townhouse on the Key West Golf Course. This one of a ...
From $332 per night (USD)
VRBO
From $524 per night (USD)
Expedia
**CARIBBEAN CHARM @ THE FOUNDRY** Villa Near Duval & Beach + LAST KEY SERVICES…
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! The sound of ...
From $524 per night (USD)
Expedia
From $4035 per night (USD)
VRBO
**ALL TOGETHER NOW @ OLD TOWN** Three Homes & Pools + LAST KEY SERVICES…
Bedrooms:
15
Bathrooms:
13
Sleeps:
32
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Coordinating ...
From $4035 per night (USD)
VRBO
$Central walk-up studio with partial ac - walk to Duval Street bars\/dining$
Click For Pricing
Expedia
Central walk-up studio with partial ac - walk to Duval Street bars\/dining
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Truman at Duval - Unit E Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ente ...
Click For Pricing
Expedia
From $1084 per night (USD)
VRBO
**MAYA’S SECRET TREASURE @ DUVAL** Private Pool & Balcony over Duval + LAST KEY
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Walking along ...
From $1084 per night (USD)
VRBO
From $1352 per night (USD)
Expedia
Balcony on Duval - Duval's Duet on Duval
Bedrooms:
2
Bathrooms:
6
Sleeps:
16
Summary: Located right in the heart of the World Famous Duval Street, enjoy a true downtown Key West experience! Duval's ...
From $1352 per night (USD)
Expedia
$Old Town home a short walk to Duval\/Couples Oasis$
From $301 per night (USD)
VRBO
Old Town home a short walk to Duval\/Couples Oasis
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summary: Add this listing to your wishlist by clicking the ♥ in the upper right hand corner. This 1 bedroom/1.5 bathroom ...
From $301 per night (USD)
VRBO
$Relaxing island home\/Great location\/Stylish$
From $253 per night (USD)
Expedia
Relaxing island home\/Great location\/Stylish
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summary: Only 4 short blocks to Duval, this 1 bedroom/1.5 bathroom home is walking distance to your favorite Key West sp ...
From $253 per night (USD)
Expedia
From $830 per night (USD)
VRBO
5 STAR yet low rates. 3 BR + 1 BR cottage, private pool, close to Duval.
Bedrooms:
4
Bathrooms:
5
Sleeps:
8
Our calendar is updated in real time and our rates are accurately displayed. You can book instantly without waiting for ...
From $830 per night (USD)
VRBO
From $394 per night (USD)
Expedia
The Emelina, Key West Monthly Rental
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The Emelina is located in a beautiful historic home. This unit is luxuriously appointed with elegant materials and impe ...
From $394 per night (USD)
Expedia
$SUGAR PALM SUITE ~ Adult Only, Cozy 1 BR, 1 Ba w\/ Kitchen and Shared Pool!$
From $394 per night (USD)
VRBO
SUGAR PALM SUITE ~ Adult Only, Cozy 1 BR, 1 Ba w\/ Kitchen and Shared Pool!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
SULTRY GARDEN SANCTUARY... Steal away from reality and find your way to the quintessential, tropical & adults only Trave ...
From $394 per night (USD)
VRBO
$COCONUT PALM SUITE ~ Adult Only, 1 BR, 1 Ba w\/ Kitchen & Shared Pool!$
From $386 per night (USD)
Expedia
COCONUT PALM SUITE ~ Adult Only, 1 BR, 1 Ba w\/ Kitchen & Shared Pool!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
BOTANICAL MAGIC AWAITS YOU... Only three blocks from all of the fine dining and entertainment of Duval Street, yet tucke ...
From $386 per night (USD)
Expedia
$ROYAL PALM SUITE ~ Adult Only, 1 BR, 1 Ba w\/ Kitchen and Shared Pool!$
From $384 per night (USD)
VRBO
ROYAL PALM SUITE ~ Adult Only, 1 BR, 1 Ba w\/ Kitchen and Shared Pool!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
ESCAPE TO A BOTANICAL HIDEAWAY... Immerse yourself at the charming adults only Travelers Palm Inn with unique suites and ...
From $384 per night (USD)
VRBO
From $572 per night (USD)
Expedia
ISLAND OASIS in the Truman Annex
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Island Oasis @ the Truman Annex is beautifully renovated town home in the historic Foundry. | The living area is the ent ...
From $572 per night (USD)
Expedia
From $163 per night (USD)
VRBO
NEW MONTHLY RENTAL, Old Town, Duplex, JUNE OPEN, private backyard, pets welcome
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Sea Monkey and The Mermaid. Our home is a duplex located in Old Town and full of Key West charm. Walk to a ...
From $163 per night (USD)
VRBO
$Conch Cottage | 'Old Town' Home w\/ Shared Pool$
From $186 per night (USD)
Expedia
Conch Cottage | 'Old Town' Home w\/ Shared Pool
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Escape to this charming Key West cottage, the perfect home base for your island getaway. Whether you relax by t ...
From $186 per night (USD)
Expedia
$Charming 'Boho Breeze' Retreat w\/ Pool Access$
From $250 per night (USD)
VRBO
Charming 'Boho Breeze' Retreat w\/ Pool Access
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Experience crystal clear waters, picturesque beaches, and famous historic sites with a stay at 'Boho Breeze!' This 2-bed ...
From $250 per night (USD)
VRBO
From $692 per night (USD)
Expedia
Enjoy Old Town Key West in this Beautifully furnished house
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
We recently bought this house because we LOVE Key West! It is a 2 story Key West style house. The bedrooms are upstair ...
From $692 per night (USD)
Expedia
From $350 per night (USD)
VRBO
Yellow Room at the Grand Maloney
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: The Grand Maloney Hotel is a new boutique hotel located in the heart of downtown Key West. Our signature red br ...
From $350 per night (USD)
VRBO
From $354 per night (USD)
Expedia
Blue Room at the Grand Maloney
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: The Grand Maloney Hotel is a new boutique hotel located in the heart of downtown Key West. Our signature red br ...
From $354 per night (USD)
Expedia
From $354 per night (USD)
VRBO
Green Room at the Grand Maloney
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: The Grand Maloney Hotel is a new boutique hotel located in the heart of downtown Key West. Our signature red br ...
From $354 per night (USD)
VRBO
From $370 per night (USD)
Expedia
Poolside King Room Steps from Duval!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The Poolside King Room is a hotel-style room adjacent to the pool. It can sleep up to four persons, two in the king-size ...
From $370 per night (USD)
Expedia
From $288 per night (USD)
VRBO
Poolside Queen Room Steps from Duval!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The Poolside Queen Room is a hotel-style bedroom and bath unit that offers the amenities of our Key West villas for thos ...
From $288 per night (USD)
VRBO
From $443 per night (USD)
Expedia
One Bedroom Deck Villa Steps from Duval!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Enjoy a wonderful Key West accommodation. Our One Bedroom Deck Villa features a living room, a separate bedroom with ki ...
From $443 per night (USD)
Expedia
From $233 per night (USD)
VRBO
Duval Street Suites on Duval Free Parking and heated Pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Cuban Club Suite is a one bedroom (queen) 1 bath suite with a queen murphy bed and kitchen. Overlooking Duval ...
From $233 per night (USD)
VRBO
From $257 per night (USD)
Expedia
Duval Street Suites full kitchen, free parking, & heated pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: The Key West Suite is a one bedroom (king) 1 bath suite with a sleeper sofa (queen) and kitchen. In historic O ...
From $257 per night (USD)
Expedia
From $255 per night (USD)
VRBO
Duval Street Suites full kitchen, free parking, heated pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Paradise Suite is a one bedroom (king bed) 1 bath suite with a murphy bed (queen) and kitchen. In historic Old ...
From $255 per night (USD)
VRBO
From $242 per night (USD)
Expedia
Duval Street Suites full kitchen and heated pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: The Little Palm Suite is a one bedroom (king) 1 bath suite with a sleeper sofa (queen) and kitchen. Overlookin ...
From $242 per night (USD)
Expedia
From $356 per night (USD)
VRBO
Duval Street Suites with full kitchen heated pool, free parking
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Mile Zero Suite is a one bedroom (queen) 1 bath suite with a sleeper sofa (king) and kitchen. Overlooking Duva ...
From $356 per night (USD)
VRBO
From $1917 per night (USD)
Expedia
6 BR 6 BA Guesthouse Suites on Duval free parking, private pool
Bedrooms:
6
Bathrooms:
6
Sleeps:
24
Summary: This can accommodate 24 people, each apartment has 2 beds. You'll have privacy with 6 individual suites each eq ...
From $1917 per night (USD)
Expedia
$MONTHLY RENTAL, Old Town, Duplex, private yard, 2 BR\/2 BA$
From $161 per night (USD)
VRBO
MONTHLY RENTAL, Old Town, Duplex, private yard, 2 BR\/2 BA
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Sea Monkey and The Mermaid! Our home is a duplex located in Old Town and full of Key West charm. Both unit ...
From $161 per night (USD)
VRBO
From $588 per night (USD)
Expedia
Parking & Near Duval - Poolside Suite
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Summary: Poolside Suite is the PERFECT vacation home for family and friends looking for a fun-filled getaway in the hear ...
From $588 per night (USD)
Expedia
From $341 per night (USD)
VRBO
AWAY FROM IT ALL @ The Truman Annex
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The c ...
From $341 per night (USD)
VRBO
From $662 per night (USD)
Expedia
Galleon Resort beach hotel luxury in Old Town Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
This is a large (1245 SF) 1BR/1BA condo on the 6th floor of the Galleon Resort & Marina.....and is a one of a kind. It ...
From $662 per night (USD)
Expedia
From $1642 per night (USD)
VRBO
NEW PRICING: DRIVE TO YOUR GETAWAY - BIG Pool, Steps to Beach & Free Parking
Bedrooms:
6
Bathrooms:
5
Sleeps:
12
Seaside Place welcomes guests from all states and follows all cleanliness and safety guidelines. Your safety and comfor ...
From $1642 per night (USD)
VRBO
From $993 per night (USD)
Expedia
**THE ZESTY LIME @ OLD TOWN** Beautifully Restored Home + LAST KEY SERVICES…
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Key West is k ...
From $993 per night (USD)
Expedia
$Craig & Cindy Key West Truman Annex Shipyard Condo w\/ a patio at Mile Marker 0!$
From $357 per night (USD)
VRBO
Craig & Cindy Key West Truman Annex Shipyard Condo w\/ a patio 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 $357 per night (USD)
VRBO
From $522 per night (USD)
Expedia
Balcony, Pool, & Pet Friendly - The Grand Turk
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Welcome to Sunrise Suites, a peaceful community on Key West's southeast side. Just 1 mile from the beach and 10 ...
From $522 per night (USD)
Expedia
From $239 per night (USD)
VRBO
Duval Street Suites full kitchen Old Town with heated pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: The Key Lime Suite is a one bedroom (king) 1 bath suite with a sleeper sofa (queen) and full kitchen complete w ...
From $239 per night (USD)
VRBO
From $476 per night (USD)
Expedia
Ocean Hideaway a Key West Nature retreat close to Smathers & 15 to Duval
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $476 per night (USD)
Expedia
From $435 per night (USD)
VRBO
Caribbean Conch 5 Minutes to Smathers Beach & 10 minute Bike Downtown - Value
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $435 per night (USD)
VRBO
Click For Pricing
Expedia
Close enough to Bike Ride to Mallory Square,far away to sleep during FantasyFest
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Coconut Mallory Resort and marina has multiple amenities including two pools, hot tubs, open air restaurant and bar, mar ...
Click For Pricing
Expedia
From $313 per night (USD)
VRBO
Rent a Piece of Paradise, Best Location on the Island!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Rent a piece of paradise right in the heart of beautiful Old Town Key West. Walking distance to all major attraction (r ...
From $313 per night (USD)
VRBO
From $545 per night (USD)
Expedia
Balcony, Pool, & Pet Friendly - The Trinidad
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Welcome to Sunrise Suites, a peaceful community on Key West's southeast side. Just 1 mile from the beach and 10 ...
From $545 per night (USD)
Expedia
From $399 per night (USD)
VRBO
The Palms...A beautiful space in the perfect place.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
The perfect space in the perfect place. A quiet oasis on the 2nd floor nestled amongst palm trees in the shipyard secti ...
From $399 per night (USD)
VRBO
From $344 per night (USD)
Expedia
**DANCE OF THE BUTTERFLIES @ SOUTHERNMOST** New Home & Pool + LAST KEY SERVICES.
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! For a month i ...
From $344 per night (USD)
Expedia
From $670 per night (USD)
VRBO
A BANANA REPUBLIC in Old Town Key West
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
A Banana Republic Gem. This Old Town house may be the nicest property in Key West. Totally redone and professionally dec ...
From $670 per night (USD)
VRBO
From $879 per night (USD)
Expedia
**THE TOASTED COCONUT @ OLD TOWN** Fully Restored + Pool + LAST KEY SERVICES…
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Throughout Ke ...
From $879 per night (USD)
Expedia
From $517 per night (USD)
VRBO
Balcony, Pool, & Pet Friendly - The Barbados
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Welcome to the quiet Sunrise Suites community located on the southeast side of Key West. Just 1 mile from the b ...
From $517 per night (USD)
VRBO
$Bright Key West House with Private Pool, Gas Grill, W\/D, Central AC, & Free WiFi$
From $503 per night (USD)
Expedia
Bright Key West House with Private Pool, Gas Grill, W\/D, Central AC, & Free WiFi
Bedrooms:
6
Bathrooms:
4
Sleeps:
8
Tropical Vibes Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $503 per night (USD)
Expedia
From $173 per night (USD)
VRBO
Atlantic Ocean Breezes, Tropical Island Sunrises, Downtown 10 minutes away
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Experience elegant sophistication in this stunning 2-bedroom, 2-bathroom ocean-view condominium at the premier 1800 Atla ...
From $173 per night (USD)
VRBO
From $300 per night (USD)
Expedia
BOOK NOW FOR AMAZING DEALS FOR KEY WEST APRIL - SEPTEMBER $3750 A MONTH
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
You will love our piece of paradise. Our home away from home is tiled throughout. All new furnishings in 2017. Large fla ...
From $300 per night (USD)
Expedia
From $1577 per night (USD)
VRBO
Private Parking & Pool, Near Duval - Contra House
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
Summary: This captivating modern home with a striking exterior and vaulted ceilings makes for the perfect vacation home. ...
From $1577 per night (USD)
VRBO
From $470 per night (USD)
Expedia
Island Time Hideaway at Old Town Key West Historic Seaport - 3 Blocks to Duval
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
LOCATION, LOCATION, LOCATION! Located on a picturesque Old Town street, in one of the most desirable areas of the hist ...
From $470 per night (USD)
Expedia
$Key West Cabana-Old Town Key West- Steps to Duval Street w\/ Pool & Tiki Bar$
From $362 per night (USD)
VRBO
Key West Cabana-Old Town Key West- Steps to Duval Street w\/ Pool & Tiki Bar
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Key West Cabana welcomes you to our quaint 2 bedroom, 2 bathroom home with large private pool, assigned parking for 2 ca ...
From $362 per night (USD)
VRBO
From $566 per night (USD)
Expedia
Happy’s Houseboat Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
This beautiful houseboat is the best way to stay in Key West. Recently Featured in Old Dominion‘s music video “I was on ...
From $566 per night (USD)
Expedia
From $241 per night (USD)
VRBO
Private Paradise with Heated Waterfall Pool
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Time to sit back and relax! Paradise found in this completely redone home in Key West. Private outdoor heated pool, show ...
From $241 per night (USD)
VRBO
From $1545 per night (USD)
Expedia
Sublime Sunsets Waterfront Condo at The Truman Annex in Key West
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
Breathtaking waterfront view from this 4 bedroom, 4.5 bath condominium in Harbour Place in the Truman Annex is ready to ...
From $1545 per night (USD)
Expedia
From $172 per night (USD)
VRBO
Centrally located cottage apartment with patio - walk to beach & dining
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Bottoms Up Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $172 per night (USD)
VRBO
From $268 per night (USD)
Expedia
Gorgeous Home with Lush Patio & Private Pool - Two Blocks to Higgs Beach
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
Sunshine Drive Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $268 per night (USD)
Expedia
Click For Pricing
VRBO
Cozy condo with free WiFi & fantastic location in central Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
Truman at Duval - Unit C Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ente ...
Click For Pricing
VRBO
From $241 per night (USD)
Expedia
A+ Location in Old Town Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
The house has beautiful vaulted high ceilings. Along with the en-suite there is also another bathroom on the 1st floor a ...
From $241 per night (USD)
Expedia
From $733 per night (USD)
VRBO
AFTERNOON DELIGHT at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This amazing 2 bedroom/2 bath condo has one of the best views in Key West. Located in the historic Mills Place in Truman ...
From $733 per night (USD)
VRBO
$**SWEET AMERICANA @ OLD TOWN** 8BR\/8BA Compound + 2 Pools + LAST KEY SERVICES…$
From $2476 per night (USD)
Expedia
**SWEET AMERICANA @ OLD TOWN** 8BR\/8BA Compound + 2 Pools + LAST KEY SERVICES…
Bedrooms:
10
Bathrooms:
8
Sleeps:
20
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! It doesn't ge ...
From $2476 per night (USD)
Expedia
From $203 per night (USD)
VRBO
Julia's Secret
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Best location in Key West! Just steps from the world class shops and restaurants of world famous Duval Street. There are ...
From $203 per night (USD)
VRBO
From $291 per night (USD)
Expedia
Upscale end unit home @ Truman Annex close to Duval St
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
Now more than ever it is important it is important to choose a home that is thoroughly cleaned and well maintained. We ...
From $291 per night (USD)
Expedia
From $798 per night (USD)
VRBO
Dream Vacation! 3 Awesome Units, Pool, On-Site Bar, Gym, Parking!
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $798 per night (USD)
VRBO
From $740 per night (USD)
Expedia
Ultimate Key West Adventure! 3 Serene Units, Pool, Parking, Bar, Restaurant!
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $740 per night (USD)
Expedia
From $233 per night (USD)
VRBO
King Bed Accommodation at The Gates Hotel Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $233 per night (USD)
VRBO
From $233 per night (USD)
Expedia
Escape to the Beach! Pool, Restaurant, Gym, Bike Rentals, Parking!
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $233 per night (USD)
Expedia
From $266 per night (USD)
VRBO
Pool View Two Queen Beds at The Gates Hotel Key West, Swimming Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $266 per night (USD)
VRBO
From $249 per night (USD)
Expedia
Pool View King at The Gates Hotel Key West, Onsite Swimming Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $249 per night (USD)
Expedia
From $224 per night (USD)
VRBO
**DRIFTWOOD DREAMS @ 1800 ATLANTIC** Beachside Condo & Pool + LAST KEY SERVICES.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE - There will be concrete restoration happening in this complex through Summer 2026. This constructio ...
From $224 per night (USD)
VRBO
From $1255 per night (USD)
Expedia
Poolside Paradise | Heated Pool, Steps to Duval St!
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
Summary: This 3 bed 2 bath home with an amazing HEATED pool is located right off the quieter end of Duval St. The home c ...
From $1255 per night (USD)
Expedia
From $396 per night (USD)
VRBO
Poolside Retreat | Shared Heated Pool, Near Duval
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Poolside Retreat is the PERFECT vacation home for a couple or small group of friends looking for a fun-filled g ...
From $396 per night (USD)
VRBO
Click For Pricing
Expedia
Updated home with private pool, patio, & grill in enclosed tropical backyard
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Margaret Street Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
Click For Pricing
Expedia
From $3071 per night (USD)
VRBO
Banana's Foster Guesthouse | 1 Block to Duval St
Bedrooms:
8
Bathrooms:
9
Sleeps:
19
Summary: Palm trees, sunsets, and the blissful pace of island time will all be yours when you stay at this large histori ...
From $3071 per night (USD)
VRBO
From $378 per night (USD)
Expedia
Fully renovated Condo with Private Balcony, Shared Pool, Hot Tub and Parking
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
*Brand New Listing* Welcome to Captains Choice The NICEST Unit at Sunrise Suites Resort in Key West- Unit 302. Tropical ...
From $378 per night (USD)
Expedia
From $359 per night (USD)
VRBO
~Bahari House, Seaport~Walk to the harbor from this quintessential conch home
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local ...
From $359 per night (USD)
VRBO
From $1258 per night (USD)
Expedia
Old Town Retreat near Upper Duval St
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Casa Caribe! When you think of the Caribbean, you think of tranquil blue green waters and a fun vibe. That's the feel wh ...
From $1258 per night (USD)
Expedia
From $440 per night (USD)
VRBO
Dog-friendly condo with pool & hot tub - walk or bike to beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Sunrise Suites - Paradise Escape 407 Our calendar is updated in real-time & our nightly rates are accurately displayed. ...
From $440 per night (USD)
VRBO
$Sea Breeze Cottage 2 Large Decks, pool, free parking\/wifi in Truman Annex$
From $506 per night (USD)
Expedia
Sea Breeze Cottage 2 Large Decks, pool, free parking\/wifi in Truman Annex
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Sea Breeze Cottage Cottage is a private, tropical, stand alone cottage located in the prestigious Truman Annex. This is ...
From $506 per night (USD)
Expedia
From $452 per night (USD)
VRBO
Charming Studio in Historic Key West, 5-Min Bike Ride to Beach & Bikes Included!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Location, location, location! Situated in the heart of the Cuban district, steps from arguably the best 'con leche' in ...
From $452 per night (USD)
VRBO
From $480 per night (USD)
Expedia
'LA DOLCE VITA' OLD TOWN, STEPS TO DUVAL! SLEEPS 2-4, 3 BLOCKS TO SOUTH BEACH!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
La Dolce Vita is located in the heart of Old Town Key West and just steps to Duval Street in the heart of the Hist ...
From $480 per night (USD)
Expedia
From $456 per night (USD)
VRBO
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Here in Key West we believe in One Human Family where everyone is welcome and treated like family. Key West! .....it’s ...
From $456 per night (USD)
VRBO
From $1066 per night (USD)
Expedia
**GOOD VIBRATIONS @ OLD TOWN** Unique Villa & Pool + LAST KEY SERVICES…
Bedrooms:
5
Bathrooms:
4
Sleeps:
10
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Key West has ...
From $1066 per night (USD)
Expedia
From $333 per night (USD)
VRBO
Galleon Resort efficiency
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This unit has a queen size bed. Updated ceramic stand up shower. The unit is an efficiency.It has a small refrigerator, ...
From $333 per night (USD)
VRBO
Click For Pricing
Expedia
3 blocks from waterfront and 1 block off Duval in heart of Old Town Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Want to “ Get away from it all” but still be in the heart of Olde Town Key West with everything you need right there? Th ...
Click For Pricing
Expedia
From $994 per night (USD)
VRBO
Seaside Retreat: Waterfront Home with private heated pool & lush landscaping
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautifu ...
From $994 per night (USD)
VRBO
Click For Pricing
Expedia
3 blocks from waterfront and 1 block off Duval in Old Town Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Want to “ Get Away from it all” but still in the heart of Old Town Key West with everything you need within walking dist ...
Click For Pricing
Expedia

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