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From $881 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 $881 per night (USD)
VRBO
From $828 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 $828 per night (USD)
Expedia
From $879 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 $879 per night (USD)
VRBO
From $160 per night (USD)
VRBO
Ocean-breeze Key West Cottage
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
This property recently fully renovated. Original house was built in 1892. 1 bedroom 1 bathroom apartment with hardwood f ...
From $160 per night (USD)
VRBO
From $916 per night (USD)
VRBO
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 $916 per night (USD)
VRBO
From $816 per night (USD)
VRBO
Southard Love: 2.5 Blocks to Duval, beach & historic seaport. 4 Beds, 3 Baths
Bedrooms:
3
Bathrooms:
4
Sleeps:
7
'SOUTHARD LOVE' is located on Southard Street on the corner of LOVE Lane This home is a perfect example of WHY people c ...
From $816 per night (USD)
VRBO
From $261 per night (USD)
VRBO
Beautiful Upper Duval - Uptown - 2 bedroom Condo
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Location, Location!!Welcome to our Key West Condo! This beautiful Upper Duvalcondo is walkable to everything in Key West ...
From $261 per night (USD)
VRBO
From $247 per night (USD)
Expedia
Fairway Villa w/ Private Pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Fairway Villa — a stunning, spacious 3-bedroom, 3-bathroom townhouse nestled on the beautiful Key West Golf C ...
From $247 per night (USD)
Expedia
From $225 per night (USD)
VRBO
Key West-Coconut Beach Resort - Avail 11/14/26 to 11/21/26
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Book it before it's gone - 7 day rental - available from Saturday 11/14/26 to Saturday 11/21/26 only. Cozy and comforta ...
From $225 per night (USD)
VRBO
From $325 per night (USD)
VRBO
ShangriLa Suite / Queen Studio / Sleeps 2
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Mingle with other guests around the tropical gardens surrounding the heated pool and sundeck creating the perfect settin ...
From $325 per night (USD)
VRBO
From $326 per night (USD)
VRBO
Tropical Paradise In Key West-Coconut Beach Resort - Avail 4/25/25 to 5/2/26
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Book it before it's gone! 7 Day rental - available from Saturday 4/25/26 to Saturday 5/2/26 only. Cozy and comfortable ...
From $326 per night (USD)
VRBO
From $338 per night (USD)
Expedia
LA PUERTA ROSA~Charming 3 bed/2 bath Conch Home in Old Town Key West!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
**Please note that this rental only allows for payment by check/E-check. Credit card payment will be subject to additio ...
From $338 per night (USD)
Expedia
From $220 per night (USD)
VRBO
Single Family Home, 3 Bedroom, 2 Baths, Pool. Great Value!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Private home located in New Town available for 4 week minimum rental. Beautifully landscaped yard with secure private b ...
From $220 per night (USD)
VRBO
From $524 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 $524 per night (USD)
Expedia
From $175 per night (USD)
VRBO
Peaceful One Bedroom Retreat Located Blocks From Duval Street And The Harbor.
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This one bedroom loft apartment with full kitchen and laundry has everything you need for an extended stay! Located on o ...
From $175 per night (USD)
VRBO
From $3628 per night (USD)
Expedia
**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 $3628 per night (USD)
Expedia
From $675 per night (USD)
VRBO
Key West On THE BEACH New Years! Dec 27th - Jan 3rd 2026
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
PLEASE READ CAREFULLY BEFORE YOU EMAIL OWNER This rental is for a 7 NIGHT HOLIDAY 1 week RENTAL ONLY! This is for 7 n ...
From $675 per night (USD)
VRBO
From $1929 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 $1929 per night (USD)
Expedia
From $755 per night (USD)
VRBO
2-Bedroom Villa at Hyatt Beach House! Quiet Beachfront Location! Sleeps 6
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Located on a private beach, this quiet piece of Key West is an excellent choice for relaxation while also situated only ...
From $755 per night (USD)
VRBO
From $2485 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 $2485 per night (USD)
Expedia
From $812 per night (USD)
VRBO
Largest Shipyard Condo in the Truman Annex - over twice the size with a loft!
Bedrooms:
3
Bathrooms:
5
Sleeps:
8
Shipyard PENTHOUSE! This unit was supposed to be 2 units but it was built as one larger unit plus two lofts were added. ...
From $812 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 $731 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 $731 per night (USD)
Expedia
From $919 per night (USD)
VRBO
Luxury Private Home w/ Heated Pool in Key West
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
28 DAY MINIMUM. This gated property includes a 3 bedroom 2 bathroom main house (main level) PLUS a 1 bedroom 1 bathroom ...
From $919 per night (USD)
VRBO
From $341 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 $341 per night (USD)
Expedia
From $336 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 $336 per night (USD)
VRBO
From $355 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 $355 per night (USD)
VRBO
From $330 per night (USD)
VRBO
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 $330 per night (USD)
VRBO
From $580 per night (USD)
Expedia
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)
Expedia
Click For Pricing
VRBO
Pet friendly Monthly Rental with Private Pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Lush tropical grounds greet you upon entrance of this enhanced 3/2 monthly rental home. This adorable retreat is located ...
Click For Pricing
VRBO
From $419 per night (USD)
Expedia
SOUTHERN CROSS ~ Conveniently Located 3 Bedroom, 2.5 Bathroom Gem w/ Pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
SOUTHERN HOSPITALITY... Find your luxurious, island retreat nestled in the heart of Old Town, just blocks from the beaut ...
From $419 per night (USD)
Expedia
From $190 per night (USD)
VRBO
NEW MONTHLY RENTAL, Old Town Duplex, private backyard, pets welcome, 2BR/2BA
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 $190 per night (USD)
VRBO
From $472 per night (USD)
Expedia
Craig & Cindy Key West Truman Annex Shipyard Condo w/ balcony at Mile Marker 0!
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Partial list of rental amenities at Craig & Cindy's Truman Annex Shipyard Condo includes: 2 bedrooms 2 full bath {queen ...
From $472 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 $885 per night (USD)
VRBO
Duval Street, Condo, Luxury,
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
We know that you will enjoy staying in this oasis of comfort in the paradise of Key West. Our Cuban Club Condo is a 1500 ...
From $885 per night (USD)
VRBO
From $504 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 $504 per night (USD)
VRBO
From $540 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 $540 per night (USD)
Expedia
From $504 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 $504 per night (USD)
VRBO
From $271 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 $271 per night (USD)
Expedia
From $224 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 $224 per night (USD)
VRBO
From $370 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 $370 per night (USD)
Expedia
From $451 per night (USD)
VRBO
TROPICAL FRONT ~ Remodeled 2 BR, 2.5 Ba w/ Parking in Perfect Location!
Bedrooms:
2
Bathrooms:
2
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 $451 per night (USD)
VRBO
From $233 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 $233 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: The Key West Suite is a one bedroom (king) 1 bath suite with a sleeper sofa (queen) and kitchen. In historic O ...
From $255 per night (USD)
VRBO
From $252 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 $252 per night (USD)
Expedia
From $243 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 (king) and kitchen. Overlooking ...
From $243 per night (USD)
VRBO
From $234 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 $234 per night (USD)
Expedia
From $2736 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 $2736 per night (USD)
VRBO
From $448 per night (USD)
Expedia
BLUE BUNGALOW ~ 2 Bedroom Townhome in Truman Annex Community with Pool!
Bedrooms:
2
Bathrooms:
2
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 $448 per night (USD)
Expedia
From $180 per night (USD)
VRBO
MONTHLY RENTAL, Old Town Duplex, private backyard, 2 BR/2 BA, pets ok
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 $180 per night (USD)
VRBO
From $731 per night (USD)
VRBO
Penthouse Suite @ KW, Galleon Resort, Not Available in 2024-2025
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
The Galleon Resort is the best location - Old Town Key West, walking location to all the bars, many high quality restaur ...
From $731 per night (USD)
VRBO
From $580 per night (USD)
VRBO
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 $580 per night (USD)
VRBO
From $433 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 $433 per night (USD)
Expedia
From $619 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 $619 per night (USD)
VRBO
From $2070 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 $2070 per night (USD)
Expedia
From $411 per night (USD)
VRBO
Craig & Cindy Key West Truman Annex Shipyard Condo with balcony at Mile Marker 0
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Partial list of rental amenities at Craig & Cindy's Truman Annex Shipyard Condos include: 2 bedrooms 1 bath {queen and ...
From $411 per night (USD)
VRBO
From $833 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 $833 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 $515 per night (USD)
Expedia
Pet Friendly, Pool, Free Parking - 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 $515 per night (USD)
Expedia
From $236 per night (USD)
VRBO
Craig & Cindy Key West Truman Annex 2 bedroom 2 bath Shipyard Condo at MM 0!
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Partial list of rental amenities at Craig & Cindy's Truman Annex Shipyard Condo includes: 2 bedrooms 2 bath {queen and ...
From $236 per night (USD)
VRBO
From $561 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 $561 per night (USD)
Expedia
From $428 per night (USD)
VRBO
Ocean views and beach breezes at La Brisa's #303 West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
28 DAY MINIMUM RENTAL Let "the breeze" of La Brisa cool you as you relax on your balcony overlooking the salt ponds, a ...
From $428 per night (USD)
VRBO
From $666 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 $666 per night (USD)
Expedia
From $483 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 $483 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 $494 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 $494 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 $353 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 $353 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 $499 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 $499 per night (USD)
VRBO
From $1932 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 $1932 per night (USD)
Expedia
From $520 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 $520 per night (USD)
VRBO
From $286 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 $286 per night (USD)
VRBO
From $327 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 $327 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 $162 per night (USD)
VRBO
Seaside Condo, 2 pools, close to Old Town
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 $162 per night (USD)
VRBO
From $432 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 $432 per night (USD)
VRBO
From $1238 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 $1238 per night (USD)
VRBO
From $546 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 $546 per night (USD)
Expedia
From $203 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 $203 per night (USD)
VRBO
From $504 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 $504 per night (USD)
Expedia
$Perfect Location, \nPrivate Heated Pool,\nPristine Luxury Home!$
From $1832 per night (USD)
VRBO
Perfect Location, \nPrivate Heated Pool,\nPristine Luxury Home!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Octopus’s Garden — Top-Rated Key West Rental with 150+ 5-Star Reviews! Location: Steps from Duval Street & Ernest Hemin ...
From $1832 per night (USD)
VRBO
From $809 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 $809 per night (USD)
Expedia
From $809 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 $809 per night (USD)
VRBO
From $185 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 $185 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 $998 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 $998 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 $2811 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 $2811 per night (USD)
Expedia
From $582 per night (USD)
VRBO
Island Time Hideaway at Old Town Key West Historic Seaport - 3 Blocks to Duval
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Charming Historic Bungalow with Private Pool & Detached Cottage – Steps from Duval Street! Experience the best of Key W ...
From $582 per night (USD)
VRBO
From $474 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
Experience the Best of Key West at Key West Cabana — Your Charming 2-Bedroom, 2-Bathroom Retreat in Old Town Welcome to ...
From $474 per night (USD)
Expedia
From $581 per night (USD)
VRBO
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 $581 per night (USD)
VRBO
From $242 per night (USD)
Expedia
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 $242 per night (USD)
Expedia
From $319 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 $319 per night (USD)
VRBO
From $501 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 $501 per night (USD)
VRBO
From $145 per night (USD)
VRBO
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 $145 per night (USD)
VRBO
From $1634 per night (USD)
Expedia
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 $1634 per night (USD)
Expedia
From $161 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 $161 per night (USD)
VRBO
From $163 per night (USD)
Expedia
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)
Expedia

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