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From $844 per night (USD)
VRBO
Balcony & Near Downtown - Sky Suite on Duval
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Welcome to Sky Suite On Duval Street - a newly remodeled masterpiece that overlooks world famous Duval Street. ...
From $844 per night (USD)
VRBO
From $1099 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 $1099 per night (USD)
Expedia
From $726 per night (USD)
VRBO
Historic Old Town Key West Cigarmaker's Cottage - Cigar House, Sleeps 4
Bedrooms:
1
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 $726 per night (USD)
VRBO
From $776 per night (USD)
Expedia
Balcony on Duval - Duval Dream Loft
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! This un ...
From $776 per night (USD)
Expedia
From $770 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 $770 per night (USD)
VRBO
From $711 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 $711 per night (USD)
Expedia
From $332 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 $332 per night (USD)
VRBO
From $492 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 $492 per night (USD)
Expedia
From $3514 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 $3514 per night (USD)
VRBO
$Central walk-up studio with partial ac - walk to Duval Street bars\/dining$
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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 $920 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 $920 per night (USD)
VRBO
From $1629 per night (USD)
Expedia
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 $1629 per night (USD)
Expedia
From $301 per night (USD)
VRBO
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)
VRBO
From $253 per night (USD)
Expedia
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)
Expedia
From $761 per night (USD)
VRBO
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 $761 per night (USD)
VRBO
From $312 per night (USD)
Expedia
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 $312 per night (USD)
Expedia
From $345 per night (USD)
VRBO
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 $345 per night (USD)
VRBO
From $297 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 $297 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 $146 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 $146 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 $250 per night (USD)
Expedia
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 $250 per night (USD)
Expedia
From $692 per night (USD)
VRBO
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)
VRBO
From $535 per night (USD)
Expedia
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 $535 per night (USD)
Expedia
From $398 per night (USD)
VRBO
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 $398 per night (USD)
VRBO
From $407 per night (USD)
Expedia
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 $407 per night (USD)
Expedia
From $386 per night (USD)
VRBO
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 $386 per night (USD)
VRBO
From $334 per night (USD)
Expedia
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 $334 per night (USD)
Expedia
From $460 per night (USD)
VRBO
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 $460 per night (USD)
VRBO
From $275 per night (USD)
Expedia
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 $275 per night (USD)
Expedia
From $294 per night (USD)
VRBO
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 $294 per night (USD)
VRBO
From $309 per night (USD)
Expedia
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 $309 per night (USD)
Expedia
From $242 per night (USD)
VRBO
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)
VRBO
From $245 per night (USD)
Expedia
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 $245 per night (USD)
Expedia
From $1269 per night (USD)
VRBO
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 $1269 per night (USD)
VRBO
From $147 per night (USD)
Expedia
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 $147 per night (USD)
Expedia
From $589 per night (USD)
VRBO
Parking & Near Duval - 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 $589 per night (USD)
VRBO
From $380 per night (USD)
Expedia
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 $380 per night (USD)
Expedia
From $539 per night (USD)
VRBO
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 $539 per night (USD)
VRBO
From $1744 per night (USD)
Expedia
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)
Expedia
From $737 per night (USD)
VRBO
**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 $737 per night (USD)
VRBO
From $357 per night (USD)
Expedia
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)
Expedia
From $413 per night (USD)
VRBO
Balcony, 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 $413 per night (USD)
VRBO
From $318 per night (USD)
Expedia
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 $318 per night (USD)
Expedia
From $452 per night (USD)
VRBO
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 $452 per night (USD)
VRBO
From $399 per night (USD)
Expedia
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 $399 per night (USD)
Expedia
Click For Pricing
VRBO
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
VRBO
From $368 per night (USD)
Expedia
Balcony, 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 $368 per night (USD)
Expedia
From $305 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 $305 per night (USD)
VRBO
From $423 per night (USD)
Expedia
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 $423 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 $729 per night (USD)
Expedia
**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 $729 per night (USD)
Expedia
From $417 per night (USD)
VRBO
Balcony, Pool, & 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 $417 per night (USD)
VRBO
From $181 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 $181 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 $433 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 $433 per night (USD)
Expedia
From $1788 per night (USD)
VRBO
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 $1788 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:
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 $470 per night (USD)
Expedia
From $364 per night (USD)
VRBO
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 $364 per night (USD)
VRBO
From $266 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 $266 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 $169 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 $169 per night (USD)
Expedia
From $278 per night (USD)
VRBO
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 $278 per night (USD)
VRBO
Click For Pricing
Expedia
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
Expedia
From $240 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 $240 per night (USD)
VRBO
From $703 per night (USD)
Expedia
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 $703 per night (USD)
Expedia
From $2321 per night (USD)
VRBO
**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 $2321 per night (USD)
VRBO
From $202 per night (USD)
Expedia
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)
Expedia
From $274 per night (USD)
VRBO
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)
VRBO
From $798 per night (USD)
Expedia
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)
Expedia
From $740 per night (USD)
VRBO
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)
VRBO
From $233 per night (USD)
Expedia
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)
Expedia
From $233 per night (USD)
VRBO
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)
VRBO
From $266 per night (USD)
Expedia
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)
Expedia
From $249 per night (USD)
VRBO
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)
VRBO
From $230 per night (USD)
Expedia
**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 $230 per night (USD)
Expedia
From $1206 per night (USD)
VRBO
Poolside Paradise | Heated Pool, Steps to Duval St!
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 $1206 per night (USD)
VRBO
From $434 per night (USD)
Expedia
Poolside Retreat | Shared Heated Pool, Near Duval
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 $434 per night (USD)
Expedia
From $2433 per night (USD)
VRBO
Banana's Foster Guesthouse | 1 Block to Duval St
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 $2433 per night (USD)
VRBO
From $385 per night (USD)
Expedia
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 $385 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 $1262 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 $1262 per night (USD)
Expedia
From $334 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 $334 per night (USD)
VRBO
From $450 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 $450 per night (USD)
Expedia
From $292 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 $292 per night (USD)
VRBO
From $421 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 His ...
From $421 per night (USD)
Expedia
From $459 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 $459 per night (USD)
VRBO
From $888 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 $888 per night (USD)
Expedia
From $307 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 $307 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 $830 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 $830 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
From $279 per night (USD)
VRBO
Historic House, Gorgeous Porch, Great Location, See 5 Star Reviews
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Treat yourself, your family and friends to a grand Key West home ideal for an extended stay on the island. This wonderfu ...
From $279 per night (USD)
VRBO
From $1205 per night (USD)
Expedia
Steps from Duval with Private Pool – Coconut Palm
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: Step into the heart of Key West at Coconut Palm! Just one block from Duval Street, this tropical gem features a ...
From $1205 per night (USD)
Expedia
From $1042 per night (USD)
VRBO
Parking & Shared Pool - Casa Key West
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: - Located on the south end of Duval Street steps from the Southernmost Point! - Large open-concept condo with p ...
From $1042 per night (USD)
VRBO
From $508 per night (USD)
Expedia
Private Parking & Near Downtown - Sea Breeze
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Summary: Sea Breeze is the perfect location for your tropical getaway. This two bedroom condo is located in the heart of ...
From $508 per night (USD)
Expedia
From $1252 per night (USD)
VRBO
Waterfront Luxury Home with private pool!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautifu ...
From $1252 per night (USD)
VRBO
From $443 per night (USD)
Expedia
Panoramic Ocean: Beach from every window
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $443 per night (USD)
Expedia
From $339 per night (USD)
VRBO
Another Day in Paradise! PRIVATE POOL! Blocks from Duval, 2BR/2BA in Old Town!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
*** Located in the Old Town neighborhood. This exclusive residential area of Old Town Key West is really an extension of ...
From $339 per night (USD)
VRBO
From $445 per night (USD)
Expedia
Penthouse Beach Ocean Views- Live the Dream
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $445 per night (USD)
Expedia

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