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 $330 per night (USD)
VRBO
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. Perfect monthly r ...
From $330 per night (USD)
VRBO
From $282 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 $282 per night (USD)
Expedia
From $288 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 $288 per night (USD)
VRBO
From $288 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 $288 per night (USD)
Expedia
From $291 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 $291 per night (USD)
VRBO
From $291 per night (USD)
Expedia
King Bed + Sleeper Sofa & Balcony -James House
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: - The historic James House sits on Caroline street, just one home away from Duval street and its coveted attrac ...
From $291 per night (USD)
Expedia
From $284 per night (USD)
VRBO
King Suite with Balcony - 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 $284 per night (USD)
VRBO
From $288 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 $288 per night (USD)
Expedia
From $282 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 $282 per night (USD)
VRBO
From $291 per night (USD)
Expedia
King Bed + Sleeper Sofa & Balcony -James House
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: - The historic James House sits on Caroline street, just one home away from Duval street and its coveted attrac ...
From $291 per night (USD)
Expedia
From $291 per night (USD)
VRBO
King Suite + 2 Twins & Balcony – The James House
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: - The historic James House sits on Caroline street, just one home away from Duval street and its coveted attrac ...
From $291 per night (USD)
VRBO
From $291 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 $291 per night (USD)
Expedia
From $291 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 $291 per night (USD)
VRBO
From $284 per night (USD)
Expedia
King Suite with Balcony - 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 $284 per night (USD)
Expedia
From $265 per night (USD)
VRBO
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 $265 per night (USD)
VRBO
From $284 per night (USD)
Expedia
King Suite with Balcony - 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 $284 per night (USD)
Expedia
From $265 per night (USD)
VRBO
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 $265 per night (USD)
VRBO
From $282 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 $282 per night (USD)
Expedia
From $282 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 $282 per night (USD)
VRBO
From $291 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 $291 per night (USD)
Expedia
From $284 per night (USD)
VRBO
King Suite with Balcony - 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 $284 per night (USD)
VRBO
From $282 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 $282 per night (USD)
Expedia
From $291 per night (USD)
VRBO
King Suite + 2 Twins & Balcony – The James House
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: - The historic James House sits on Caroline street, just one home away from Duval street and its coveted attrac ...
From $291 per night (USD)
VRBO
From $1051 per night (USD)
Expedia
**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 $1051 per night (USD)
Expedia
From $753 per night (USD)
VRBO
CEASAR'S PARADISE - A MODERN LUXURY RETREAT W/ 4+ Bedrooms/ 5.5 Baths
Bedrooms:
5
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 $753 per night (USD)
VRBO
From $506 per night (USD)
Expedia
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 $506 per night (USD)
Expedia
From $481 per night (USD)
VRBO
Paradise on White Street
Bedrooms:
3
Bathrooms:
4
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 $481 per night (USD)
VRBO
From $413 per night (USD)
VRBO
Colony Poolside: A charming bungalow near Duval Street
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Located in The Colony, a secluded compound just steps from Duval Street, Colony Poolside is a peaceful retreat. Enter th ...
From $413 per night (USD)
VRBO
From $506 per night (USD)
VRBO
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 $506 per night (USD)
VRBO
From $585 per night (USD)
VRBO
CONCH CASA @ The Colony ~ the perfect monthly escape
Bedrooms:
2
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 $585 per night (USD)
VRBO
From $371 per night (USD)
VRBO
Sweet Caroline Historic Seaport Key West Home Rental Floor 1
Bedrooms:
3
Bathrooms:
3
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)
VRBO
From $335 per night (USD)
Expedia
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 $335 per night (USD)
Expedia
From $915 per night (USD)
VRBO
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 $915 per night (USD)
VRBO
From $450 per night (USD)
Expedia
Sweet Caroline Historic Seaport Key West Home Rental Floor 2
Bedrooms:
2
Bathrooms:
2
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)
Expedia
Click For Pricing
VRBO
Indoor / Outdoor Living in Old Key West
Bedrooms:
2
Bathrooms:
2
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
VRBO
From $172 per night (USD)
Expedia
GILLEY'S PLACE ~ Fully Renovated 1 Bedroom, 1 Bath Cottage in Old Town!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
AN ESCAPE LIKE NO OTHER… Disconnect from the real world and reconnect with each other in this picture perfect, quaint co ...
From $172 per night (USD)
Expedia
From $759 per night (USD)
VRBO
~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 $759 per night (USD)
VRBO
From $1100 per night (USD)
Expedia
LOST SHAKER OF SALT ~ 3 Bed, 2 Bath Pet Friendly with 40' Private Heated Pool
Bedrooms:
2
Bathrooms:
3
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 $1100 per night (USD)
Expedia
From $920 per night (USD)
VRBO
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 $920 per night (USD)
VRBO
From $358 per night (USD)
Expedia
ISLAND TIME ~ Fully Renovated Conch Home in a Great Old Town Location!
Bedrooms:
3
Bathrooms:
2
Sleeps:
8
ISLAND TIME... Award-winning, fully-renovated 1924 traditional conch style home. Relax and watch the world pass by from ...
From $358 per night (USD)
Expedia
From $1472 per night (USD)
VRBO
CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
HISTORIC OLD-WORLD CHARM WITH MODERN AMENITIES AND A LAGOON-STYLE POOL.... Once you step through the threshold of this O ...
From $1472 per night (USD)
VRBO
From $1047 per night (USD)
Expedia
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 $1047 per night (USD)
Expedia
From $2287 per night (USD)
VRBO
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 $2287 per night (USD)
VRBO
From $725 per night (USD)
Expedia
SAPODILLA HOUSE ~ Spectacular 3B/3.5Ba Annex Home w/Private Heated Pool!
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 $725 per night (USD)
Expedia
From $1300 per night (USD)
VRBO
STARS ~ 4 bedroom, 2 Bath Condo, Shared Heated Pool, Downtown Location!
Bedrooms:
2
Bathrooms:
4
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 $1300 per night (USD)
VRBO
From $266 per night (USD)
Expedia
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 $266 per night (USD)
Expedia
From $1895 per night (USD)
VRBO
Key West Island Rendezvous - Private Compound Steps Off Duval w/Pool - Sleeps 12
Bedrooms:
5
Bathrooms:
6
Sleeps:
14
Island Rendezvous vacation rental offers the perfect solution for a gathering of family or friends who desire to be in t ...
From $1895 per night (USD)
VRBO
From $471 per night (USD)
Expedia
**ANGELA’S ECLECTIC GALLERY @ SOLARIS HILL** Exceptional Home & Pool + LAST KEY
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! On an island ...
From $471 per night (USD)
Expedia
From $404 per night (USD)
VRBO
Tranquility by AvantStay | Close to Duval St w/ BBQ & Shared Pool
Bedrooms:
1
Bathrooms:
1
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 $404 per night (USD)
VRBO
From $407 per night (USD)
Expedia
Paradise Place by AvantStay | Key West Old Town Condo w/ Shared Pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Cozy apartment within biking distance to The Historic Seaport, Cuban Coffee Queen, local grocery store Fausto's, and eve ...
From $407 per night (USD)
Expedia
From $463 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 $463 per night (USD)
VRBO
From $663 per night (USD)
Expedia
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 $663 per night (USD)
Expedia
From $668 per night (USD)
VRBO
Downtown Duval Street Penthouse- Private Pool-Parking-Roof Deck- Walk Everywhere
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
• Luxury 2nd & 3rd floor Penthouse • 3 Bedrooms with private porches & 2 1/2 Baths • 2200 square feet of living space • ...
From $668 per night (USD)
VRBO
From $909 per night (USD)
Expedia
Washer & Dryer, Near Downtown - The Mesa House
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Summary: Family-friendly home with a huge front lounging porch, two kitchens, steps from the ocean and everything else t ...
From $909 per night (USD)
Expedia
From $252 per night (USD)
VRBO
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 $252 per night (USD)
VRBO
From $341 per night (USD)
Expedia
SCARLET ~ Adult Only, 2nd Floor Suite, 1 Bedroom Unit w/ Shared Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Exquisite 2nd floor king suite... DELIGHT IN OLD WORLD ALLURE... Bask in the charming ambience of the adults-only Scarl ...
From $341 per night (USD)
Expedia
From $297 per night (USD)
VRBO
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 $297 per night (USD)
VRBO
From $297 per night (USD)
Expedia
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 $297 per night (USD)
Expedia
From $303 per night (USD)
VRBO
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 $303 per night (USD)
VRBO
From $303 per night (USD)
Expedia
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 $303 per night (USD)
Expedia
From $302 per night (USD)
VRBO
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 $302 per night (USD)
VRBO
From $235 per night (USD)
Expedia
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 $235 per night (USD)
Expedia
From $170 per night (USD)
VRBO
LA PUERTA PEQUENA ~ Charming 1 Bedroom, 1 Bathroom w/ Loft in Old Town!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
**Please note that this rental only allows for payment by check/E-check. Credit card payment will be subject to additio ...
From $170 per night (USD)
VRBO
From $234 per night (USD)
Expedia
Land Of Love by AvantStay | Pets Allowed! Shared Pool! Great Location!
Bedrooms:
1
Bathrooms:
2
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 $234 per night (USD)
Expedia
From $169 per night (USD)
VRBO
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 $169 per night (USD)
VRBO
From $199 per night (USD)
Expedia
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 $199 per night (USD)
Expedia
From $856 per night (USD)
VRBO
Easy Livin' by AvantStay | Key West Home w/ Pool & BBQ | Week Long Stays Only
Bedrooms:
4
Bathrooms:
3
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 $856 per night (USD)
VRBO
From $415 per night (USD)
Expedia
Artist Garden by AvantStay | Great Location w/ Balcony, Shared Pool & BBQ!
Bedrooms:
2
Bathrooms:
2
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 $415 per night (USD)
Expedia
From $222 per night (USD)
VRBO
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 $222 per night (USD)
VRBO
From $370 per night (USD)
Expedia
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 $370 per night (USD)
Expedia
From $323 per night (USD)
VRBO
Casa de Rosalie by AvantStay | Great Location w/ Pool, BBQ & Outdoor Dining
Bedrooms:
2
Bathrooms:
3
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)
VRBO
From $230 per night (USD)
Expedia
Lazy Gecko by AvantStay | Walk to Duval St in Key West! | Month Long Stays Only
Bedrooms:
1
Bathrooms:
2
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 $230 per night (USD)
Expedia
Click For Pricing
VRBO
Priced to book! Sleeps 4- Walking Distance to Duval!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Great location in Key West. The Galleon is Walking distance to shopping, bars, dining, trolley, marina, Duval st., Mallo ...
Click For Pricing
VRBO
From $443 per night (USD)
Expedia
PINEAPPLE BREEZE ~ JUST RENOVATED Home in The Meadows with Pool!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
PICTURE PERFECT PARADISE... This newly renovated retreat is nestled in the highly sought-after neighborhood of The Meado ...
From $443 per night (USD)
Expedia
From $140 per night (USD)
VRBO
SEAPORT SANCTUARY ~ Come and Enjoy this Romantic & Lovely Couples Hideaway!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
A QUIET BUNGALOW IN THE HISTORIC SEAPORT... Private one bedroom home in the heart of Old Town. A great place for a coup ...
From $140 per night (USD)
VRBO
From $682 per night (USD)
Expedia
SEAHORSE COVE ~ Tropical Luxury Located In The Heart Of Old Town Key West!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
FLAWLESS SETTING, PERFECT LOCATION… Tucked away on a hidden lane right in the middle of Old Town, this luxurious private ...
From $682 per night (USD)
Expedia
From $220 per night (USD)
VRBO
Historic Apartment On The Waterfront
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Newly renovated historic apartment in the heart of Key West. 10 foot ceilings and huge windows allow bright, natural lig ...
From $220 per night (USD)
VRBO
Click For Pricing
Expedia
Fantasy Festival October 20, 2022-October 23, 2022 Studio Downtown Sunset Harbor
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Hyatt Residence Club Key West Sunset Harbor Fantasy Fest 2022 Location......Location, Location, Location....In the hear ...
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Expedia
From $1152 per night (USD)
VRBO
**CASA SERENDIPITY @ OLD TOWN** Historic 3BR/2BA Home & Pool + LAST KEY SERVICE
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Sometimes in ...
From $1152 per night (USD)
VRBO
From $243 per night (USD)
Expedia
PEAK OF DUVAL | 2 Bed, 2 Bath
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This Elegant & Spacious Apartment is located directly in the center of the Famous Duval Street. Enjoy Dining, Shopping, ...
From $243 per night (USD)
Expedia
From $2137 per night (USD)
VRBO
Location In Down Town Key West W/ 2 Pools, Huge Private Roof Deck & Parking
Bedrooms:
6
Bathrooms:
6
Sleeps:
16
Perfect location and great for entertaining! In the heart of Old Town Key West just steps from restaurants, bars, theate ...
From $2137 per night (USD)
VRBO
From $272 per night (USD)
VRBO
Mojitoville: 3 bedroom pet-friendly, Old Town, Private Pool, Historic Seaport
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Mojitoville is perfect for the discriminating guest who wants to enjoy close proximity to Key West's Historic Seaport wi ...
From $272 per night (USD)
VRBO
$\Tranquility \ At Ann Street Gardens Steps From Duval$
From $564 per night (USD)
VRBO
\"Tranquility \" At Ann Street Gardens Steps From Duval
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Location is ideal for this wonderful one bedroom retreat. A lush, inviting compound created so owners and guests could e ...
From $564 per night (USD)
VRBO
From $234 per night (USD)
Expedia
Key West Hideaway, ½ Mile to Beach,Walkable, Peaceful, Well-Equipped!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
ALSO WE'VE GOT YOUR BACK----ASK ABOUT OUR STORM POLICIES ...
From $234 per night (USD)
Expedia
From $881 per night (USD)
VRBO
The Gideon Lowe House - Old Town Key West
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Elegance, Sophistication, Perfection! Nothing compares to this extraordinary Old Town Key West residence. It exudes ch ...
From $881 per night (USD)
VRBO
From $844 per night (USD)
Expedia
Luxury 3-Bedroom Waterfront Home with Pool AND Dock!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Traditional meets modern in an elegant way, right in the middle of one of Key West’s most historical districts. A stay a ...
From $844 per night (USD)
Expedia
From $403 per night (USD)
VRBO
JUST OFF DUVAL~ 2nd Floor Condo in Center of Duval St. with Parking Space!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
STEPS TO DUVAL ST… Take advantage of this premier opportunity to indulge in all your desired Key West bucket list items ...
From $403 per night (USD)
VRBO
From $732 per night (USD)
VRBO
Rose Lane Villas - Villa Aqua - 2 King Bedrooms - Downtown Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Nestled on a quiet lane in the heart of Old Town Key West, Rose Lane Villas is as close to the action as you'll get with ...
From $732 per night (USD)
VRBO
From $164 per night (USD)
VRBO
CABIN FEVER ~ First Floor 1 Bedroom, 1 Bathroom with Full Kitchen and Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
SIMPLISTIC ELEGANCE... Enjoy easy island living in this quaint and cozy Key West gem located in the attractive community ...
From $164 per night (USD)
VRBO
From $1042 per night (USD)
Expedia
Conch style home in Oldtown with private pool AND dock!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
A reflection of old Key West, Eisenhower's Retreat was designed and built with the architectural feel of an old "Conch H ...
From $1042 per night (USD)
Expedia
From $1078 per night (USD)
VRBO
Luxury Waterfront Home with Private Pool and Dock!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Enjoy casual elegance with a view of famous Garrison Bight and centrally located on the edge of Old Town. This home boas ...
From $1078 per night (USD)
VRBO
$Spec @107.lodg+ Aug & sept. \n10 min walk beach, close to all +\nfull kitch& patio$
From $196 per night (USD)
Expedia
Spec @107.lodg+ Aug & sept. \n10 min walk beach, close to all +\nfull kitch& patio
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
SUMMER SPECIAL August and September Most dates @ 107. lodging plus extras per night. With 4 night stay 5th night FREE ...
From $196 per night (USD)
Expedia
From $618 per night (USD)
VRBO
Key West Oasis, Seperate Cottage, Very Private Pool and Back Yard
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Please Note: Key West Oasis is NOT suitable for families with young children, as the 2nd bedroom is not attached to the ...
From $618 per night (USD)
VRBO
From $143 per night (USD)
VRBO
Mango Tree Key West Cottage
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
True Key West flavor! 1 Bedroom 1 Bathroom apartment newly remodeled and updated Conch House located on White St.with h ...
From $143 per night (USD)
VRBO
From $178 per night (USD)
VRBO
Cottage in Old Town Key West w/ Pool, Parking and Privacy. One block from Duval!
Bedrooms:
1
Bathrooms:
1
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 blo ...
From $178 per night (USD)
VRBO
From $751 per night (USD)
Expedia
Old Town Key West Luxury 4BR – Private Pool by Historic Seaport - Monthly Rental
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Escape to the heart of Key West's historic district and immerse yourself in the vibrant island lifestyle. This 4-bedroom ...
From $751 per night (USD)
Expedia
From $967 per night (USD)
VRBO
Bella Grand Premier Estate Key West - 2 Blocks off Duval w Private Pool
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Inspired by romantic turn-of-the-century architecture, Bella Grand Premier Estate is a unique Old Town Key West estate w ...
From $967 per night (USD)
VRBO
From $409 per night (USD)
Expedia
Old Town Classic with plenty of charm, porch swing and parking
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Beautiful home with covered porch and swing! Full kitchen, washer/dryer, TV, Internet, A/C, separate patio area with twi ...
From $409 per night (USD)
Expedia
$\A Bird's Eye View\ at The Truman Annex in Key West$
From $426 per night (USD)
VRBO
\"A Bird's Eye View\" at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Stunning, Modern 2 bedroom, 1 bathroom second floor condo in the Truman Annex Shipyard Complex completely renovated. Ful ...
From $426 per night (USD)
VRBO
From $1612 per night (USD)
VRBO
Waterfront Penthouse sleeps 16 w/Pool & Boat Dock
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
Summary: Gorgeous completely renovated 2400sqft waterfront Penthouse condo in downtown Key West. Boat slips available on ...
From $1612 per night (USD)
VRBO

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