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From $675 per night (USD)
VRBO
Balcony on Duval - The Collins on Duval
Bedrooms:
1
Bathrooms:
2
Sleeps:
8
Summary: Located right in the heart of the World Famous Duval Street, enjoy a true downtown Key West experience! The Col ...
From $675 per night (USD)
VRBO
From $787 per night (USD)
Expedia
Historic Old Town Key West Cigarmaker's Cottage - Conch House, Sleeps 5
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The Conch House is a 100+ year old “Cigarmaker’s house. The house is recently renovated, charming, spacious, secluded a ...
From $787 per night (USD)
Expedia
From $335 per night (USD)
VRBO
Fairway Villa w/ Private Pool
Bedrooms:
2
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 $335 per night (USD)
VRBO
From $502 per night (USD)
Expedia
**CARIBBEAN CHARM @ THE FOUNDRY** Villa Near Duval & Beach + LAST KEY SERVICES…
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! The sound of ...
From $502 per night (USD)
Expedia
From $4070 per night (USD)
VRBO
**ALL TOGETHER NOW @ OLD TOWN** Three Homes & Pools + LAST KEY SERVICES…
Bedrooms:
14
Bathrooms:
13
Sleeps:
32
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Coordinating ...
From $4070 per night (USD)
VRBO
From $1280 per night (USD)
Expedia
**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 $1280 per night (USD)
Expedia
From $1240 per night (USD)
VRBO
Balcony on Duval - Duval's Duet on Duval
Bedrooms:
2
Bathrooms:
4
Sleeps:
16
Summary: Located right in the heart of the World Famous Duval Street, enjoy a true downtown Key West experience! Duval's ...
From $1240 per night (USD)
VRBO
From $301 per night (USD)
Expedia
Old Town home a short walk to Duval/Couples Oasis
Bedrooms:
1
Bathrooms:
1
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)
Expedia
From $253 per night (USD)
VRBO
Relaxing island home/Great location/Stylish
Bedrooms:
1
Bathrooms:
1
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)
VRBO
From $723 per night (USD)
Expedia
5 STAR yet low rates. 3 BR + 1 BR cottage, private pool, close to Duval.
Bedrooms:
0
Bathrooms:
4
Sleeps:
8
Our calendar is updated in real time and our rates are accurately displayed. You can book instantly without waiting for ...
From $723 per night (USD)
Expedia
From $323 per night (USD)
VRBO
SUGAR PALM SUITE ~ Adult Only, Cozy 1 BR, 1 Ba w/ Kitchen and Shared Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
SULTRY GARDEN SANCTUARY... Steal away from reality and find your way to the quintessential, tropical & adults only Trave ...
From $323 per night (USD)
VRBO
From $334 per night (USD)
Expedia
COCONUT PALM SUITE ~ Adult Only, 1 BR, 1 Ba w/ Kitchen & Shared Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
BOTANICAL MAGIC AWAITS YOU... Only three blocks from all of the fine dining and entertainment of Duval Street, yet tucke ...
From $334 per night (USD)
Expedia
From $264 per night (USD)
VRBO
Charming 'Boho Breeze' Retreat w/ Pool Access
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Experience crystal clear waters, picturesque beaches, and famous historic sites with a stay at 'Boho Breeze!' This 2-bed ...
From $264 per night (USD)
VRBO
From $323 per night (USD)
Expedia
ROYAL PALM SUITE ~ Adult Only, 1 BR, 1 Ba w/ Kitchen and Shared Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
ESCAPE TO A BOTANICAL HIDEAWAY... Immerse yourself at the charming adults only Travelers Palm Inn with unique suites and ...
From $323 per night (USD)
Expedia
From $580 per night (USD)
VRBO
ISLAND OASIS in the Truman Annex
Bedrooms:
2
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 $580 per night (USD)
VRBO
From $194 per night (USD)
Expedia
NEW MONTHLY RENTAL, Old Town Duplex, SUMMER DEALS, private backyard, pets welcom
Bedrooms:
2
Bathrooms:
2
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 $194 per night (USD)
Expedia
Click For Pricing
VRBO
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 ...
Click For Pricing
VRBO
From $692 per night (USD)
Expedia
Enjoy Old Town Key West in this Beautifully furnished house
Bedrooms:
2
Bathrooms:
2
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 $328 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 $328 per night (USD)
VRBO
From $336 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 $336 per night (USD)
Expedia
From $362 per night (USD)
VRBO
Green Room at the Grand Maloney
Bedrooms:
1
Bathrooms:
1
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 $362 per night (USD)
VRBO
From $289 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 $289 per night (USD)
Expedia
From $227 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 $227 per night (USD)
VRBO
From $316 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 $316 per night (USD)
Expedia
From $240 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 $240 per night (USD)
VRBO
From $259 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 $259 per night (USD)
Expedia
From $256 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 $256 per night (USD)
VRBO
From $244 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 (king) and kitchen. Overlooking ...
From $244 per night (USD)
Expedia
From $234 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 $234 per night (USD)
VRBO
From $2485 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 $2485 per night (USD)
Expedia
From $165 per night (USD)
VRBO
MONTHLY RENTAL, Old Town Duplex, private backyd, SUMMER DEALS, 2 BR/2 BA,pets ok
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
ou must cancel.Welcome to Sea Monkey and The Mermaid! Our home is a duplex located in Old Town and full of Key West ch ...
From $165 per night (USD)
VRBO
From $577 per night (USD)
Expedia
Parking, Pool, Near Duval St - Poolside Suite
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Summary: Poolside Suite is the PERFECT vacation home for family and friends looking for a fun-filled getaway in the hear ...
From $577 per night (USD)
Expedia
From $389 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 $389 per night (USD)
VRBO
From $444 per night (USD)
Expedia
Galleon Resort beach hotel luxury in Old Town Key West
Bedrooms:
1
Bathrooms:
1
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 $444 per night (USD)
Expedia
From $1744 per night (USD)
VRBO
NEW PRICING: DRIVE TO YOUR GETAWAY - BIG Pool, Steps to Beach & Free Parking
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Seaside Place welcomes guests from all states and follows all cleanliness and safety guidelines. Your safety and comfor ...
From $1744 per night (USD)
VRBO
From $1176 per night (USD)
Expedia
**THE ZESTY LIME @ OLD TOWN** Beautifully Restored Home + LAST KEY SERVICES…
Bedrooms:
3
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 $1176 per night (USD)
Expedia
From $357 per night (USD)
VRBO
Craig & Cindy Key West Truman Annex Shipyard Condo w/ a patio at Mile Marker 0!
Bedrooms:
1
Bathrooms:
2
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 $503 per night (USD)
Expedia
Parking, Pool & Pet Friendly - The Grand Turk
Bedrooms:
2
Bathrooms:
2
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 $503 per night (USD)
Expedia
From $247 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 $247 per night (USD)
VRBO
From $538 per night (USD)
Expedia
Ocean Hideaway a Key West Nature retreat close to Smathers & 15 to Duval
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $538 per night (USD)
Expedia
From $487 per night (USD)
VRBO
Caribbean Conch 5 Minutes to Smathers Beach & 10 minute Bike Downtown - Value
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $487 per night (USD)
VRBO
Click For Pricing
Expedia
Close enough to Bike Ride to Mallory Square,far away to sleep during FantasyFest
Bedrooms:
2
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 $504 per night (USD)
VRBO
Free Parking, Pool, & Pet Friendly - The Trinidad
Bedrooms:
2
Bathrooms:
2
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 $504 per night (USD)
VRBO
From $285 per night (USD)
Expedia
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 $285 per night (USD)
Expedia
From $447 per night (USD)
VRBO
SECOND WIND ~ Charming 2 Bedroom, 2 Bathroom Home w/ Pool!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
CATCH YOUR SECOND WIND… Unplug in this newly renovated and elegant refuge, a place of tranquility with an island ambianc ...
From $447 per night (USD)
VRBO
From $450 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 $450 per night (USD)
VRBO
From $374 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 $374 per night (USD)
VRBO
From $2973 per night (USD)
Expedia
STARS AND STRIPES ~ Magnificent Home Located In The Heart of Old Town!
Bedrooms:
4
Bathrooms:
8
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 $2973 per night (USD)
Expedia
From $344 per night (USD)
VRBO
**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)
VRBO
From $279 per night (USD)
VRBO
Eleanor's Place Key West - Historic Old Town Cottage Dog Friendly
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Eleanor's Place is a charming Key West Cottage in the heart of Key West! Featured on HGTV's Island Life, our renovated c ...
From $279 per night (USD)
VRBO
From $204 per night (USD)
VRBO
~ MY HAPPY PLACE ~ A charmingly beautiful treasure in a perfect location!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local ...
From $204 per night (USD)
VRBO
From $205 per night (USD)
VRBO
Dreamworks Conch Cottage
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
PEACEFUL RETREAT... A quintessential Key West cottage in the heart of Old Town and only a few blocks away from Higgs Bea ...
From $205 per night (USD)
VRBO
From $178 per night (USD)
VRBO
Seaside Condo, 2 pools 6 MONTHS SPECIALS
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Upon waking in the morning we hear the murmuring of tropical birds , feel the gentle sea breezes and the fragrance of j ...
From $178 per night (USD)
VRBO
From $431 per night (USD)
VRBO
Tropical Seclusion On Old Town Lane With Pool And Detached Bungalow. Sleeps 6
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Hidden at the end of one of the most beautiful lanes in Old Town, Casa Escondida awaits you with its tropical seclusion ...
From $431 per night (USD)
VRBO
From $1021 per night (USD)
VRBO
**THE TOASTED COCONUT @ OLD TOWN** Fully Restored + Pool + LAST KEY SERVICES…
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Throughout Ke ...
From $1021 per night (USD)
VRBO
From $350 per night (USD)
Expedia
EBB AND FLO ~ Newly Renovated Retreat in Old Town with Incredible Pool!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
OLD TOWN KEY WEST… Surround yourself in this newly renovated gem located in the desirable Casa Marina neighborhood neari ...
From $350 per night (USD)
Expedia
From $207 per night (USD)
VRBO
Studio overlooking historic Key West waterfront.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Overlooking the Historic Key West Bight, this bright and clean studio features a fully equipped kitchen, renovated bathr ...
From $207 per night (USD)
VRBO
From $501 per night (USD)
Expedia
Pool, Free Parking & Pet Friendly - The Barbados
Bedrooms:
2
Bathrooms:
2
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 $501 per night (USD)
Expedia
$Perfect Location, \nPrivate Heated Pool,\nPristine Luxury Home!$
From $1740 per night (USD)
VRBO
Perfect Location, \nPrivate Heated Pool,\nPristine Luxury Home!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Welcome to OCTOPUS GARDEN! The TOP Key West rental with 150+ 5-STAR reviews! Perfectly located and fully remodeled, Oc ...
From $1740 per night (USD)
VRBO
From $611 per night (USD)
Expedia
Bright Key West House with Private Pool, Gas Grill, W/D, Central AC, & Free WiFi
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
Tropical Vibes Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $611 per night (USD)
Expedia
From $661 per night (USD)
VRBO
Oceanfront Property - 2BR/2BA - Near Smather's Beach - Poolside Bar and Grill
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
★Excellent Key West Location - Oceanside Resort - Two Bedroom - Two Bath - Sleeps 6 ★Very Clean - Very Nice Property. T ...
From $661 per night (USD)
VRBO
From $202 per night (USD)
Expedia
Atlantic Ocean Breezes Tropical Island Key West Sunrises
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $202 per night (USD)
Expedia
From $300 per night (USD)
VRBO
Tropical 2BR Condo w/ Pool, Tennis, Near Beach & Downtown
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to our piece of paradise in Key West! Our beautifully maintained, fully tiled 2-bedroom condo is your perfect ho ...
From $300 per night (USD)
VRBO
From $718 per night (USD)
Expedia
ISLE AZURE ~ Charming 3 Bed/3 Bath with Private Pool in Truman Annex!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
PLEASE BE AWARE... We cannot accept a reservation of less than 28 nights after 12/22/25. You may book less than 28 nigh ...
From $718 per night (USD)
Expedia
From $1441 per night (USD)
VRBO
NEW LISTING Old Town Private Pool in Garden Of Eden tropical spa-like Oasis
Bedrooms:
0
Bathrooms:
2
Sleeps:
4
( NEW LISTING SEE VRBO LISTING 1223004 for reviews on my other property ) Newly renovated, invitingly spacious, serenely ...
From $1441 per night (USD)
VRBO
From $1710 per night (USD)
Expedia
Private Parking & Pool, Near Duval - Contra House
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
Summary: This captivating modern home with a striking exterior and vaulted ceilings makes for the perfect vacation home. ...
From $1710 per night (USD)
Expedia
From $573 per night (USD)
VRBO
Island Time Hideaway at Old Town Key West Historic Seaport - 3 Blocks to Duval
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
LOCATION, LOCATION, LOCATION! Located on a picturesque Old Town street, in one of the most desirable areas of the hist ...
From $573 per night (USD)
VRBO
From $455 per night (USD)
Expedia
Key West Cabana-Old Town Key West- Steps to Duval Street w/ Pool & Tiki Bar
Bedrooms:
2
Bathrooms:
2
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 $455 per night (USD)
Expedia
From $289 per night (USD)
VRBO
OLD TOWN SUMMER’24! Private pool, stunning decor, 5-star reviews. NO PETS
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Sun yourself on the back patio, then cool off in the pool. Rinse off in the outdoor shower with hot/cold running water. ...
From $289 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 $258 per night (USD)
VRBO
OUR HAPPY PLACE ~ Adorable 2 Bedroom, 2 Bath Condo Steps from the Beach!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
PLEASE BE AWARE: This community is currently undergoing balcony repair property-wide potentially through April 2026. A ...
From $258 per night (USD)
VRBO
From $218 per night (USD)
Expedia
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 $218 per night (USD)
Expedia
From $334 per night (USD)
VRBO
Gorgeous beach bungalow just steps from the beach!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Just seconds away from the ocean, this 3 bedroom 2 bath home with a large backyard and patio is ready for you and your f ...
From $334 per night (USD)
VRBO
From $154 per night (USD)
Expedia
A Stones Throw Away from Duval - Downtown -Caroline's Cottage KW
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Caroline's Cottage KW Welcome to Caroline’s Cottage steps away from the world’s famous Duval Street in Key West Fla. Yo ...
From $154 per night (USD)
Expedia
From $1553 per night (USD)
VRBO
Sublime Sunsets Waterfront Condo at The Truman Annex in Key West
Bedrooms:
4
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 $1553 per night (USD)
VRBO
From $161 per night (USD)
Expedia
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 $161 per night (USD)
Expedia
From $163 per night (USD)
VRBO
Cozy cottage apartment with front porch & upgraded finishes - close to beach
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Borrowed Time Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $163 per night (USD)
VRBO
From $324 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 $324 per night (USD)
Expedia
From $188 per night (USD)
VRBO
GOOD FEELIN ~ Charming 2 BR/2 Ba Home Conveniently Located w/ Parking!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
SPOIL YOURSELF… Come unwind in this tropical retreat allowing for your delightful Key West story to unfold. Sounds of sw ...
From $188 per night (USD)
VRBO
From $186 per night (USD)
Expedia
POSITIVE VIBES ~ Charming 2 BR, 1 Ba Cottage in Peaceful Area w/ Parking!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
LOST ON ISLAND TIME… Treasure your time together within this charming Key West cottage tucked away on this peaceful and ...
From $186 per night (USD)
Expedia
From $298 per night (USD)
VRBO
GOOD VIBES ~ 2 Cottages w/ 4 BR/3 Ba, Outdoor Oasis and Parking!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
MEMORIES TO LAST A LIFETIME… This unique set of 2 charming, Conch style homes provide the perfect compound setting for y ...
From $298 per night (USD)
VRBO
From $260 per night (USD)
VRBO
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 $260 per night (USD)
VRBO
From $799 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 $799 per night (USD)
VRBO
From $2649 per night (USD)
Expedia
**SWEET AMERICANA @ OLD TOWN** 8BR/8BA Compound + 2 Pools + LAST KEY SERVICES…
Bedrooms:
9
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 $2649 per night (USD)
Expedia
From $202 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 $202 per night (USD)
VRBO
From $1310 per night (USD)
Expedia
**GOOD VIBRATIONS @ OLD TOWN** Unique Villa & Pool + LAST KEY SERVICES…
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Key West has ...
From $1310 per night (USD)
Expedia
From $531 per night (USD)
VRBO
Stunning Historic Estate – 20% Off Summer Bookings, Heated Pool & Bikes Included
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Discover a delightful four-bedroom getaway nestled within the historic district of Key West. Nestled just a 13-minute wa ...
From $531 per night (USD)
VRBO
From $2634 per night (USD)
Expedia
1 Block to Duval St | Banana's Foster Guesthouse
Bedrooms:
7
Bathrooms:
7
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 $2634 per night (USD)
Expedia
From $451 per night (USD)
VRBO
Fully renovated Condo with Private Balcony, Shared Pool, Hot Tub and Parking
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
*Brand New Listing* Welcome to Captains Choice The NICEST Unit at Sunrise Suites Resort in Key West- Unit 302. Tropical ...
From $451 per night (USD)
VRBO
From $274 per night (USD)
Expedia
Upscale end unit home @ Truman Annex close to Duval St
Bedrooms:
1
Bathrooms:
1
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 $274 per night (USD)
Expedia
From $289 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 $289 per night (USD)
VRBO
From $964 per night (USD)
Expedia
Heated Pool, Steps to Duval St - Poolside Paradise
Bedrooms:
2
Bathrooms:
3
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 $964 per night (USD)
Expedia
From $372 per night (USD)
VRBO
Shared Heated Pool, Near Duval - Poolside Retreat
Bedrooms:
1
Bathrooms:
1
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 $372 per night (USD)
VRBO
From $1323 per night (USD)
VRBO
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 $1323 per night (USD)
VRBO
From $388 per night (USD)
VRBO
Dog-friendly condo with pool & hot tub - walk or bike to beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Sunrise Suites - Paradise Escape 407 Our calendar is updated in real-time & our nightly rates are accurately displayed. ...
From $388 per night (USD)
VRBO
From $431 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 $431 per night (USD)
Expedia
From $356 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 $356 per night (USD)
VRBO
From $180 per night (USD)
VRBO
Conch Republic Studio - Key West Millionaires Row
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
In the center of Key West's prestigious "Millionaires Row," Conch Republic Studio is a tranquil getaway for one or a cou ...
From $180 per night (USD)
VRBO
From $394 per night (USD)
VRBO
'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 His ...
From $394 per night (USD)
VRBO
From $444 per night (USD)
Expedia
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 $444 per night (USD)
Expedia

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