Fleming Key, Florida Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Fleming Key, Florida on RentalSaver.com!

Fleming Key Rentals

From $479 per night (USD)
VRBO
Steps from Duval, Shared Pool – Sky Loft Downtown
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Experience the best of Key West from Sky Loft, your perfect weekend getaway! Just one block from the iconic Duv ...
From $479 per night (USD)
VRBO
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Expedia
The Queens Villa
Bedrooms:
4
Bathrooms:
2
Sleeps:
4
Former Fantasy Fest Queens private residence. I also own the number one hotel in Key West. Best location at the END of ...
Click For Pricing
Expedia
$CORAZON: Old Town MONTHLY - Private Pool - LARGE 2BD\/2.5BA - RealKeyWest$
From $352 per night (USD)
VRBO
CORAZON: Old Town MONTHLY - Private Pool - LARGE 2BD\/2.5BA - RealKeyWest
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
Description: Welcome to Corazon, a stunning 2-bedroom vacation rental in the heart of Key West's Old Town neighborhood. ...
From $352 per night (USD)
VRBO
From $3557 per night (USD)
Expedia
Takeover at the Grand Maloney
Bedrooms:
7
Bathrooms:
6
Sleeps:
16
Summary: The Grand Maloney Hotel is a boutique hotel located in the heart of downtown Key West. Our signature red brick, ...
From $3557 per night (USD)
Expedia
$PINEAPPLE COTTAGE: 2BR\/2BA-Pvt Pool -1\/2 block to Duval- RealKeyWest$
From $1043 per night (USD)
VRBO
PINEAPPLE COTTAGE: 2BR\/2BA-Pvt Pool -1\/2 block to Duval- RealKeyWest
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
WELCOME TO PINEAPPLE COTTAGE! The Pineapple Cottage is a charming two-bedroom, two-bathroom home located in Old Town K ...
From $1043 per night (USD)
VRBO
$Cottage in Old Town Key West w\/ Pool, Parking and Privacy. One block from Duval!$
From $235 per night (USD)
VRBO
Cottage in Old Town Key West w\/ Pool, Parking and Privacy. One block from Duval!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Down a hidden lane in the heart of Old Town Key West you will find Loco Court Cottages.The compound is located one block ...
From $235 per night (USD)
VRBO
$Cottage in Old Town Key West w\/ Pool, Parking and Privacy. One block from Duval!$
From $293 per night (USD)
VRBO
Cottage in Old Town Key West w\/ Pool, Parking and Privacy. One block from Duval!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Down a hidden lane in the heart of Old Town Key West you will find Loco Court Cottages.The compound is located one block ...
From $293 per night (USD)
VRBO
From $1162 per night (USD)
Expedia
Key West Wabi Sabi - Authentic Downtown Cottage w Pool - Steps Off Duval
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Undeniably adorable, Key West Wabi Sabi vacation rental is a celebration of authentic Key West cottage style island livi ...
From $1162 per night (USD)
Expedia
$Classic Key West Estate - 7BR Mansion off Duval St w\/Pool & Guesthouse Sleeps 16$
From $2399 per night (USD)
VRBO
Classic Key West Estate - 7BR Mansion off Duval St w\/Pool & Guesthouse Sleeps 16
Bedrooms:
6
Bathrooms:
7
Sleeps:
16
Featured on HGTV House Hunters on Vacation, the timeless charm of this distinguished Classic Key West Estate vacation re ...
From $2399 per night (USD)
VRBO
From $1324 per night (USD)
Expedia
Pavilion Villa – A Key West Private Paradise 1 Block Off Duval w Pool
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
A Private Tropical Paradise ... is the feeling you get when you enter the pavilion of this award winning villa just a ha ...
From $1324 per night (USD)
Expedia
From $2186 per night (USD)
VRBO
Features.Key West Suites Hotel has an outdoor pool and fitness center
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Key West Suites Hotel Welcome to your charming private studio apartment right on Duval street! Built in 1919, it used ...
From $2186 per night (USD)
VRBO
$SEA-NIC VIEW ~ 2 BR\/2Ba Water-front views, Heated Pool Access and Dockage!$
From $220 per night (USD)
Expedia
SEA-NIC VIEW ~ 2 BR\/2Ba Water-front views, Heated Pool Access and Dockage!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
IT'S A SWELL LIFE… Endless island treasures engulf this oceanfront haven which is your one stop destination for a comple ...
From $220 per night (USD)
Expedia
Click For Pricing
VRBO
Beautiful views and close to Duval Street festivities and boat docks. Wks 29-30.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Two bedroom condo units in the premier Galleon Resort with unique access to dockage and rental boats. The units include ...
Click For Pricing
VRBO
$Pearl in Paradise-Charming 2bed 2bath Old Town home w\/ shared pool, parking$
From $179 per night (USD)
VRBO
Pearl in Paradise-Charming 2bed 2bath Old Town home w\/ shared pool, parking
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
AGE REQUIREMENT: Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their ...
From $179 per night (USD)
VRBO
$Antigua Retreat- 2BR 2BA waterfront condo w\/ pool & boat slip$
From $548 per night (USD)
VRBO
Antigua Retreat- 2BR 2BA waterfront condo w\/ pool & boat slip
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
AGE REQUIREMENT: Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their ...
From $548 per night (USD)
VRBO
From $497 per night (USD)
VRBO
Ann Street Cottage: A bright and airy home near Duval Street
Bedrooms:
2
Bathrooms:
1
Sleeps:
2
Tucked away in an inviting compound you'll find the perfect hideaway called Ann Street Cottage; a charming one bedroom c ...
From $497 per night (USD)
VRBO
From $504 per night (USD)
VRBO
Come stay in an amazing house close to everything! Duvall! North Seaport!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
We love this home, and we just know you will too!! A fully renovated conch home with amazing finishes and 3 great bedro ...
From $504 per night (USD)
VRBO
From $350 per night (USD)
Expedia
The Bolivar, Old Town Key West Monthly vacation rental
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Tuck upstairs in the back of a historic Conch house is a home away from home with private back porch. 1 Block walk from ...
From $350 per night (USD)
Expedia
From $678 per night (USD)
VRBO
~ SOLARIS PAIR-A-DISE ~ A garden lover’s dream on a quiet Key West lane.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
THE PROPERTY: If you are looking for that tropical island vibe, look no further! Both sections of this casual home are ...
From $678 per night (USD)
VRBO
From $455 per night (USD)
Expedia
The Patricia, 1 BR, 1 BA monthly vacation rental home
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Located in the heart of Old Town Key West is a quaint Key West Home that offers a crisp palette of blue, lime and white ...
From $455 per night (USD)
Expedia
From $384 per night (USD)
VRBO
Deluxe Queen & Pet Friendly - Curry Mansion Inn
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...
From $384 per night (USD)
VRBO
From $385 per night (USD)
Expedia
Deluxe Queen & Pet Friendly - Curry Mansion Inn
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...
From $385 per night (USD)
Expedia
From $299 per night (USD)
VRBO
Deluxe Queen & Pet Friendly - Curry Mansion Inn
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...
From $299 per night (USD)
VRBO
From $299 per night (USD)
Expedia
Deluxe Queen & Pet Friendly - Curry Mansion Inn
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...
From $299 per night (USD)
Expedia
From $369 per night (USD)
VRBO
Classic King & Private Balcony - Curry Mansion Inn
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...
From $369 per night (USD)
VRBO
From $332 per night (USD)
Expedia
Deluxe Queen & Pet Friendly - Curry Mansion Inn
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...
From $332 per night (USD)
Expedia
From $355 per night (USD)
VRBO
Classic King, Pool - Curry Mansion Inn
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...
From $355 per night (USD)
VRBO
From $347 per night (USD)
Expedia
Tropical oasis in a former author’s retreat. Sleeps 4.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Former residence of an author and decorated accordingly, this cute cottage is quintessential Key West. Perfectly maintai ...
From $347 per night (USD)
Expedia
From $377 per night (USD)
VRBO
Classic King, Pool - Curry Mansion Inn
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...
From $377 per night (USD)
VRBO
From $369 per night (USD)
Expedia
Classic King & Private Balcony - Curry Mansion Inn
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...
From $369 per night (USD)
Expedia
From $369 per night (USD)
VRBO
Classic King & Private Balcony - Curry Mansion Inn
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...
From $369 per night (USD)
VRBO
From $372 per night (USD)
Expedia
Deluxe King, Pet Friendly & - Curry Mansion Inn
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...
From $372 per night (USD)
Expedia
From $384 per night (USD)
VRBO
King Suite with Balcony - The James House
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: - The historic James House sits on Caroline street, just one home away from Duval street and its coveted attrac ...
From $384 per night (USD)
VRBO
From $396 per night (USD)
Expedia
Deluxe King with Balcony - The James House
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Summary: - The historic James House sits on Caroline street, just one home away from Duval street and its coveted attrac ...
From $396 per night (USD)
Expedia
From $383 per night (USD)
VRBO
Classic King & Private Balcony - Curry Mansion Inn
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...
From $383 per night (USD)
VRBO
From $377 per night (USD)
Expedia
Classic King, Pool - Curry Mansion Inn
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...
From $377 per night (USD)
Expedia
From $389 per night (USD)
VRBO
King Suite with Balcony - The James House
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: - The historic James House sits on Caroline street, just one home away from Duval street and its coveted attrac ...
From $389 per night (USD)
VRBO
From $385 per night (USD)
Expedia
King Suite with Balcony - The James House
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: - The historic James House sits on Caroline street, just one home away from Duval street and its coveted attrac ...
From $385 per night (USD)
Expedia
From $364 per night (USD)
VRBO
King Suite, Pet Friendly & Shared Pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...
From $364 per night (USD)
VRBO
From $369 per night (USD)
Expedia
King Suite, Pet Friendly & Shared Pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...
From $369 per night (USD)
Expedia
From $404 per night (USD)
VRBO
Classic King Balcony, Parking - The James House
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: - The historic James House sits on Caroline street, just one home away from Duval street and its coveted attrac ...
From $404 per night (USD)
VRBO
From $346 per night (USD)
Expedia
Classic Queen, Pet Friendly - Curry Mansion Inn
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...
From $346 per night (USD)
Expedia
From $408 per night (USD)
VRBO
Classic King Balcony, Parking - The James House
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: - The historic James House sits on Caroline street, just one home away from Duval street and its coveted attrac ...
From $408 per night (USD)
VRBO
From $347 per night (USD)
Expedia
Classic Queen, Pet Friendly - Curry Mansion Inn
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...
From $347 per night (USD)
Expedia
From $377 per night (USD)
VRBO
Classic King, Pool - Curry Mansion Inn
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...
From $377 per night (USD)
VRBO
From $377 per night (USD)
Expedia
Classic King, Pool - Curry Mansion Inn
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...
From $377 per night (USD)
Expedia
From $374 per night (USD)
VRBO
Deluxe King, Pet Friendly & - Curry Mansion Inn
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...
From $374 per night (USD)
VRBO
From $396 per night (USD)
Expedia
Deluxe King with Balcony - The James House
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Summary: - The historic James House sits on Caroline street, just one home away from Duval street and its coveted attrac ...
From $396 per night (USD)
Expedia
From $377 per night (USD)
VRBO
Classic King, Pool - Curry Mansion Inn
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...
From $377 per night (USD)
VRBO
From $385 per night (USD)
Expedia
King Suite with Balcony - The James House
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: - The historic James House sits on Caroline street, just one home away from Duval street and its coveted attrac ...
From $385 per night (USD)
Expedia
From $858 per night (USD)
VRBO
**DARLING OF DUVAL @ OLD TOWN** Estate Cottage + Spa + LAST KEY SERVICES…
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Don't miss an ...
From $858 per night (USD)
VRBO
$CEASAR'S PARADISE - A MODERN LUXURY RETREAT W\/ 4+ Bedrooms\/ 5.5 Baths$
From $888 per night (USD)
VRBO
CEASAR'S PARADISE - A MODERN LUXURY RETREAT W\/ 4+ Bedrooms\/ 5.5 Baths
Bedrooms:
6
Bathrooms:
5
Sleeps:
10
Modern sophistication is the design aesthetic in this newer built home in Old Town Key West with designer touches throug ...
From $888 per night (USD)
VRBO
From $886 per night (USD)
VRBO
Two Bedroom Two Bath Balcony Villa Steps from Duval!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The Two Bedroom Balcony Villa is a gracious two story Key West rental decorated in a tropical style with a living room, ...
From $886 per night (USD)
VRBO
From $487 per night (USD)
VRBO
Paradise on White Street
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
After spending your day out on the water or strolling down Duval St., come relax at this Charming 2-Story Historic Home. ...
From $487 per night (USD)
VRBO
From $365 per night (USD)
VRBO
Colony Poolside: A charming bungalow near Duval Street
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
Located in The Colony, a secluded compound just steps from Duval Street, Colony Poolside is a peaceful retreat. Enter th ...
From $365 per night (USD)
VRBO
From $886 per night (USD)
Expedia
Two Bedroom Two Bath Poolside Villa Steps from Duval!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
We have the perfect accommodation for a family vacation or friends getaway in Old Town Key West, Florida. Our Two-Bedroo ...
From $886 per night (USD)
Expedia
From $461 per night (USD)
VRBO
CONCH CASA @ The Colony ~ the perfect monthly escape
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
The property features a beautiful, heated community pool and one reserved off-street parking space (a coveted old town r ...
From $461 per night (USD)
VRBO
From $371 per night (USD)
Expedia
Sweet Caroline Historic Seaport Key West Home Rental Floor 1
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
The unit located on the first floor has three-dimensional ceilings throughout with indirect LED lighting. The kitchen is ...
From $371 per night (USD)
Expedia
From $561 per night (USD)
VRBO
Studio Near Downtown - The Bartlum
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Welcome to the Bartlum, a historic and luxurious studio apartment just steps to Duval Street. This studio, lo ...
From $561 per night (USD)
VRBO
$Casa Rosa: 4BR\/4BA house, pool, near Duval$
From $876 per night (USD)
Expedia
Casa Rosa: 4BR\/4BA house, pool, near Duval
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Welcome to Casa Rosa, your tropical sanctuary nestled in the vibrant heart of Key West, Florida. *Saturday-to-Saturday ...
From $876 per night (USD)
Expedia
From $450 per night (USD)
VRBO
Sweet Caroline Historic Seaport Key West Home Rental Floor 2
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This fully renovated house is located in the historic seaport with many highly rated restaurants and shops. A quick 5-mi ...
From $450 per night (USD)
VRBO
$Indoor \/ Outdoor Living in Old Key West$
Click For Pricing
Expedia
Indoor \/ Outdoor Living in Old Key West
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Our home is down a quiet lane in the heart of Key West. Walk to Duval Street, organic “fast food,” yoga, beer, fishin ...
Click For Pricing
Expedia
From $163 per night (USD)
VRBO
GILLEY'S PLACE ~ Fully Renovated 1 Bedroom, 1 Bath Cottage in Old Town!
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
AN ESCAPE LIKE NO OTHER… Disconnect from the real world and reconnect with each other in this picture perfect, quaint co ...
From $163 per night (USD)
VRBO
From $1008 per night (USD)
Expedia
~Butterfly Cottage~ Enjoy a hot tub, gourmet kitchen, and 2 king ensuites.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
PROPERTY: Enjoy your coffee on the front porch or listen to the birds while gliding on the swing. Either way, you will a ...
From $1008 per night (USD)
Expedia
From $1198 per night (USD)
VRBO
LOST SHAKER OF SALT ~ 3 Bed, 2 Bath Pet Friendly with 40' Private Heated Pool
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
THE HEART OF OLD TOWN... Charming Old Town home in the heart of Key West. Located on Southard Street just steps from Du ...
From $1198 per night (USD)
VRBO
$CONCH HEAVEN ~ Stylish 2B\/2Ba, Sleeps 6 in Old Town w\/ Heated Cocktail Pool!$
From $956 per night (USD)
Expedia
CONCH HEAVEN ~ Stylish 2B\/2Ba, Sleeps 6 in Old Town w\/ Heated Cocktail Pool!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
OLD TOWN LOCATION... A beautifully furnished and comfortable home, located just 5 short blocks to Duval Street. Have bi ...
From $956 per night (USD)
Expedia
From $332 per night (USD)
VRBO
ISLAND TIME ~ Fully Renovated Conch Home in a Great Old Town Location!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
ISLAND TIME... Award-winning, fully-renovated 1924 traditional conch style home. Relax and watch the world pass by from ...
From $332 per night (USD)
VRBO
From $1362 per night (USD)
Expedia
CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
HISTORIC OLD-WORLD CHARM WITH MODERN AMENITIES AND A LAGOON-STYLE POOL.... Once you step through the threshold of this O ...
From $1362 per night (USD)
Expedia
$STRIPES ~ Delightful Condo w\/Shared Pool in the Heart of Old Town Key West!$
From $1285 per night (USD)
VRBO
STRIPES ~ Delightful Condo w\/Shared Pool in the Heart of Old Town Key West!
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
When you don't need the entire compound but still want to enjoy this magnificent property in the heart of Old Town Key W ...
From $1285 per night (USD)
VRBO
From $2326 per night (USD)
Expedia
SOUTHERNMOST BELLE~ Heated Pool, Gourmet Kitchen & Elegant Large Bedrooms!
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
LUXURY IN OLD TOWN... Grand home in the Historic Seaport area of Old Town Key West. Tucked behind a canopy of palms this ...
From $2326 per night (USD)
Expedia
$SAPODILLA HOUSE ~ Spectacular 3B\/3.5Ba Annex Home w\/Private Heated Pool!$
From $1179 per night (USD)
VRBO
SAPODILLA HOUSE ~ Spectacular 3B\/3.5Ba Annex Home w\/Private Heated Pool!
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
PREMIER TROPICAL RETREAT... Come spoil yourself in this conveniently located two-story home tucked away on a quiet lane ...
From $1179 per night (USD)
VRBO
From $1067 per night (USD)
Expedia
STARS ~ 4 bedroom, 2 Bath Condo, Shared Heated Pool, Downtown Location!
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
When you do not need the entire compound but still want to enjoy this magnificent property in the heart of Old Town Key ...
From $1067 per night (USD)
Expedia
From $278 per night (USD)
VRBO
HEMINGWAY'S HIDEOUT ~ Historic Old Town Cottage with Pool!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
ISLAND TIME AWAITS… Step up to this serene, tropical cottage inviting you in with a multitude of swaying palms, a privat ...
From $278 per night (USD)
VRBO
$Key West Island Rendezvous - Private Compound Steps Off Duval w\/Pool - Sleeps 12$
From $2273 per night (USD)
Expedia
Key West Island Rendezvous - Private Compound Steps Off Duval w\/Pool - Sleeps 12
Bedrooms:
5
Bathrooms:
7
Sleeps:
14
Island Rendezvous vacation rental offers the perfect solution for a gathering of family or friends who desire to be in t ...
From $2273 per night (USD)
Expedia
From $511 per night (USD)
VRBO
**ANGELA’S ECLECTIC GALLERY @ SOLARIS HILL** Exceptional Home & Pool + LAST KEY
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! On an island ...
From $511 per night (USD)
VRBO
$Tranquility by AvantStay | Close to Duval St w\/ BBQ & Shared Pool$
From $534 per night (USD)
Expedia
Tranquility by AvantStay | Close to Duval St w\/ BBQ & Shared Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Settled in a small community in Old Town, only a short walk to Duval Street, this lovely cottage offers everything you c ...
From $534 per night (USD)
Expedia
$Paradise Place by AvantStay | Key West Old Town Condo w\/ Shared Pool$
From $473 per night (USD)
VRBO
Paradise Place by AvantStay | Key West Old Town Condo w\/ Shared Pool
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Cozy apartment within biking distance to The Historic Seaport, Cuban Coffee Queen, local grocery store Fausto's, and eve ...
From $473 per night (USD)
VRBO
From $543 per night (USD)
VRBO
The Most Perfect Old Town Key West Location for a Retreat!
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
The home (also known as Margaux's Hideaway) was built in 1890's, with a farmhouse charm, and porches off of every bedroo ...
From $543 per night (USD)
VRBO
From $470 per night (USD)
VRBO
THE SEASHELL ~ Classic, Luxury Old Town Gem with Private Pool & Gardens!
Bedrooms:
3
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 $470 per night (USD)
VRBO
From $1132 per night (USD)
Expedia
Downtown Duval Street Penthouse- Private Pool-Parking-Roof Deck- Walk Everywhere
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
• Luxury 2nd & 3rd floor Penthouse • 3 Bedrooms with private porches & 2 1/2 Baths • 2200 square feet of living space • ...
From $1132 per night (USD)
Expedia
From $1142 per night (USD)
VRBO
Washer & Dryer, Near Downtown - The Mesa House
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
Summary: Family-friendly home with a huge front lounging porch, two kitchens, steps from the ocean and everything else t ...
From $1142 per night (USD)
VRBO
$Key Lime Pie by AvantStay | Ideal Location w\/ Splash Pool & Out Door Dining$
From $254 per night (USD)
Expedia
Key Lime Pie by AvantStay | Ideal Location w\/ Splash Pool & Out Door Dining
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
*Please note that this home is available for 28+ night stays only.* Key Lime Pie is a private cottage that perfectly en ...
From $254 per night (USD)
Expedia
$SCARLET ~ Adult Only, 2nd Floor Suite, 1 Bedroom Unit w\/ Shared Pool!$
From $595 per night (USD)
VRBO
SCARLET ~ Adult Only, 2nd Floor Suite, 1 Bedroom Unit w\/ Shared Pool!
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
Exquisite 2nd floor king suite... DELIGHT IN OLD WORLD ALLURE... Bask in the charming ambience of the adults-only Scarl ...
From $595 per night (USD)
VRBO
$GOLDEN NUGGET ~ Adult Only, 1st Floor Queen Bedroom w\/ Shared Pool!$
From $424 per night (USD)
Expedia
GOLDEN NUGGET ~ Adult Only, 1st Floor Queen Bedroom w\/ Shared Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Beautiful 1st floor queen room just off the pool for easy access... DELIGHT IN OLD WORLD ALLURE... Bask in the charming ...
From $424 per night (USD)
Expedia
$NumberEleven ~ Charming Adult Only, 1 Bedroom, 1 Bath w\/ Shared Pool!$
From $404 per night (USD)
VRBO
NumberEleven ~ Charming Adult Only, 1 Bedroom, 1 Bath w\/ Shared Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Charming 1st Floor King for Convenience... DELIGHT IN OLD WORLD ALLURE... Bask in the charming ambience of the adults-o ...
From $404 per night (USD)
VRBO
$HONEY~ Adult Only, 2nd Floor 1 King Bedroom Unit w\/ Shared Pool!$
From $449 per night (USD)
Expedia
HONEY~ Adult Only, 2nd Floor 1 King Bedroom Unit w\/ Shared Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Gorgeous 2nd floor king room and ample balcony space... DELIGHT IN OLD WORLD ALLURE... Bask in the charming ambience of ...
From $449 per night (USD)
Expedia
$KEITT ~ Adult Only, 2nd Floor 1 Bedroom w\/ Shared Pool, Scarlet Mango Inn!$
From $412 per night (USD)
VRBO
KEITT ~ Adult Only, 2nd Floor 1 Bedroom w\/ Shared Pool, Scarlet Mango Inn!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Bright and airy 2nd floor king room... DELIGHT IN OLD WORLD ALLURE... Bask in the charming ambience of the adults-only ...
From $412 per night (USD)
VRBO
$JULIE ~ Adult Only, 1st Floor King Bedroom w\/ Shared Pool, Scarlet Mango Inn!$
From $427 per night (USD)
Expedia
JULIE ~ Adult Only, 1st Floor King Bedroom w\/ Shared Pool, Scarlet Mango Inn!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Lovely 1st floor king room steps from the pool for easy access... DELIGHT IN OLD WORLD ALLURE... Bask in the charming a ...
From $427 per night (USD)
Expedia
$BONITA EN ROSA ~ Charming 2 Bedroom, 1 Bathroom Home w\/ Pool!$
From $206 per night (USD)
VRBO
BONITA EN ROSA ~ Charming 2 Bedroom, 1 Bathroom Home w\/ Pool!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
**Please note that this rental only allows for payment by check/E-check. Credit card payment will be subject to additio ...
From $206 per night (USD)
VRBO
$LA PUERTA PEQUENA ~ Charming 1 Bedroom, 1 Bathroom w\/ Loft in Old Town!$
From $211 per night (USD)
Expedia
LA PUERTA PEQUENA ~ Charming 1 Bedroom, 1 Bathroom w\/ Loft in Old Town!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
**Please note that this rental only allows for payment by check/E-check. Credit card payment will be subject to additio ...
From $211 per night (USD)
Expedia
From $193 per night (USD)
VRBO
Land Of Love by AvantStay | Pets Allowed! Shared Pool! Great Location!
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
*Please note that this home is available for 28+ night stays only.* Your perfect escape to Key West awaits you in the L ...
From $193 per night (USD)
VRBO
From $203 per night (USD)
Expedia
Boat House by AvantStay | Character Cottage | Central Location Month Long Stays
Bedrooms:
2
Bathrooms:
1
Sleeps:
2
*Please note that this home is available for 28+ night stays only.* Step into a tranquil community on a quiet lane and ...
From $203 per night (USD)
Expedia
$Ibis by AvantStay | Close to Duval Street w\/ Shared Pool | Month Long Stays Only$
From $193 per night (USD)
VRBO
Ibis by AvantStay | Close to Duval Street w\/ Shared Pool | Month Long Stays Only
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
*Please note that this home is available for 28+ night stays only.* Enjoy your private front porch in this quiet neighb ...
From $193 per night (USD)
VRBO
$Easy Livin' by AvantStay | Key West Home w\/ Pool & BBQ | Week Long Stays Only$
From $1103 per night (USD)
Expedia
Easy Livin' by AvantStay | Key West Home w\/ Pool & BBQ | Week Long Stays Only
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
*Please note that this home is available for stays of 7+ days only. Starting January 1, 2026, it will be available for s ...
From $1103 per night (USD)
Expedia
$Artist Garden by AvantStay | Great Location w\/ Balcony, Shared Pool & BBQ!$
From $561 per night (USD)
VRBO
Artist Garden by AvantStay | Great Location w\/ Balcony, Shared Pool & BBQ!
Bedrooms:
3
Bathrooms:
3
Sleeps:
4
*Please note that this home is available for stays of 7+ days only. Starting January 1, 2026, it will be available for s ...
From $561 per night (USD)
VRBO
$Paradise Palms by AvantStay | Great Location w\/ Outdoor Dining, BBQ$
From $211 per night (USD)
Expedia
Paradise Palms by AvantStay | Great Location w\/ Outdoor Dining, BBQ
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
*Please note that this home is available for 28+ night stays only.* Make your next Florida vacation something special w ...
From $211 per night (USD)
Expedia
$First Breath by AvantStay | Close to Old Town w\/ Pool | Month Long Stays Only$
From $347 per night (USD)
VRBO
First Breath by AvantStay | Close to Old Town w\/ Pool | Month Long Stays Only
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
*Please note that this home is available for 28+ night stays only.* Bring the family to this 3 bed, 2 bath private conc ...
From $347 per night (USD)
VRBO
$Casa de Rosalie by AvantStay | Great Location w\/ Pool, BBQ & Outdoor Dining$
From $323 per night (USD)
Expedia
Casa de Rosalie by AvantStay | Great Location w\/ Pool, BBQ & Outdoor Dining
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
*Please note that this home is available for 28+ night stays only.* Built-in 1889 with original Dade County Pine, histo ...
From $323 per night (USD)
Expedia
From $228 per night (USD)
VRBO
Lazy Gecko by AvantStay | Walk to Duval St in Key West! | Month Long Stays Only
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
*Please note that this home is available for 28+ night stays only.* Grab your bike and head for some fresh seafood at t ...
From $228 per night (USD)
VRBO
Click For Pricing
Expedia
Priced to book! Sleeps 4- Walking Distance to Duval!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Great location in Key West. The Galleon is Walking distance to shopping, bars, dining, trolley, marina, Duval st., Mallo ...
Click For Pricing
Expedia

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