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 $274 per night (USD)
VRBO
Balcony, Pool, & Near Duval - Curry House Room 6
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Curry House offers three stories of historic Conch house charm, perfect for your getaway. This guesthouse featu ...
From $274 per night (USD)
VRBO
From $438 per night (USD)
Expedia
Balcony, Pool, Near Duval - Curry House Room 3 + 4
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Curry House offers three stories of historic charm, transporting you back in time. The guesthouse features priv ...
From $438 per night (USD)
Expedia
From $293 per night (USD)
VRBO
Balcony, Pool, & Near Duval - Curry House Room 1
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: "Curry House" provides three stories full of historic conch house charm that take you back in time. This guesth ...
From $293 per night (USD)
VRBO
From $274 per night (USD)
Expedia
Balcony, Pool, & Near Duval - Curry House Room 8
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: "Curry House" provides three stories full of historic charm that take you back in time. This guesthouse has pr ...
From $274 per night (USD)
Expedia
From $446 per night (USD)
VRBO
Balcony, Pool, & Near Duval - Curry House Room 7
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: "Curry House" provides three stories full of historic charm that take you back in time. This guesthouse has pr ...
From $446 per night (USD)
VRBO
From $283 per night (USD)
Expedia
Balcony, Pool, & Near Duval - Curry House Room 2
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: "Curry House" provides three stories full of historic charm that take you back in time. This guesthouse has pr ...
From $283 per night (USD)
Expedia
From $240 per night (USD)
VRBO
Balcony, Pool, & Near Duval - Curry House Room 9
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: "Curry House" provides three stories full of historic charm that take you back in time. This guesthouse has pr ...
From $240 per night (USD)
VRBO
From $275 per night (USD)
Expedia
Curry House | Heated Pool, King Bed, 1st Floor
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: "Curry House" provides three stories full of historic charm that take you back in time. This guesthouse has pr ...
From $275 per night (USD)
Expedia
From $796 per night (USD)
VRBO
Sweet Caroline | Banana's Foster Guesthouse
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
Summary: Banana's Foster Guest House is a charming historic conch home in the heart of Key West, just steps from the his ...
From $796 per night (USD)
VRBO
From $372 per night (USD)
Expedia
KeyLime Cottage | Banana's Foster Guesthouse
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Banana's Foster Guest House is a charming historic conch home in the heart of Key West, just steps from the his ...
From $372 per night (USD)
Expedia
From $308 per night (USD)
VRBO
Sugar Pie Suite | Banana's Foster Guesthouse
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Banana's Foster Guest House is a charming historic conch home in the heart of Key West, just steps from the his ...
From $308 per night (USD)
VRBO
From $360 per night (USD)
Expedia
Honeybun Hideaway at Banana's Foster Guesthouse
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Banana's Foster Guest House is a charming historic conch home in the heart of Key West, just steps from the his ...
From $360 per night (USD)
Expedia
From $433 per night (USD)
VRBO
Banana Split | Banana's Foster Guesthouse
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Banana's Foster Guest House is a charming historic conch home in the heart of Key West, just steps from the his ...
From $433 per night (USD)
VRBO
From $404 per night (USD)
Expedia
Creme Brulee Suite | Banana's Foster Guesthouse
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Banana's Foster Guest House is a charming historic conch home in the heart of Key West, just steps from the his ...
From $404 per night (USD)
Expedia
From $323 per night (USD)
VRBO
Heart of Old Town on QUIET Peacon Lane. Historic Seaport. Duval St. PETS WELCOME
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Single family home. (Not a condo.) We welcome kids, pets, partners, friends. Free off street parking for 2-3 vehicles. ...
From $323 per night (USD)
VRBO
From $342 per night (USD)
Expedia
Carriage House 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 $342 per night (USD)
Expedia
From $377 per night (USD)
VRBO
Bunk 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 $377 per night (USD)
VRBO
From $224 per night (USD)
Expedia
Old Town Key West classic with private saltwater pool & enclosed patio- by shops
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Petronia Paradise Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $224 per night (USD)
Expedia
$Colorful cottage w\/shared pool, central AC, washer\/dryer$
Click For Pricing
VRBO
Colorful cottage w\/shared pool, central AC, washer\/dryer
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
Grinnell Street Getaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
Click For Pricing
VRBO
From $855 per night (USD)
Expedia
Luxury Waterfront at Galion Resort in Old Town
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This condo is a 2BR/2BA Penthouse Loft on the 5th floor overlooking the marina. On the first floor is a full sized, ful ...
From $855 per night (USD)
Expedia
From $954 per night (USD)
VRBO
3-Story spacious conch style home w/ private pool & dock!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
"Seafarer’s Refuge” is a spacious home with the ability to sleep a large group comfortably, a private pool and tropicall ...
From $954 per night (USD)
VRBO
From $394 per night (USD)
Expedia
The Galleon Resort Best Resort Location in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
June unit 1bd 1ba with pull out sofa-sleeps 4, 5th floor with large balcony, great marina views. The Galleon Resort has ...
From $394 per night (USD)
Expedia
From $304 per night (USD)
VRBO
Anchors Away - Old Town Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Anchors Away offers traditional Conch style living and is located in the coveted Old Town Key West. This home is unbeata ...
From $304 per night (USD)
VRBO
From $379 per night (USD)
Expedia
Red 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 $379 per night (USD)
Expedia
From $334 per night (USD)
VRBO
**CASITA OLIVIETTA @ SOLARES HILL** Brand New Home & Private Pool + LAST KEY SER
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! You don’t oft ...
From $334 per night (USD)
VRBO
From $1185 per night (USD)
Expedia
Oversized home for the whole family w/private pool & dock
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
"Captain's Daughter” is a spacious home with the ability to sleep a large group comfortably, a private pool and tropical ...
From $1185 per night (USD)
Expedia
From $1141 per night (USD)
VRBO
Spacious home with pool & balcony - 1 block from Duval Street
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Last Minute Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $1141 per night (USD)
VRBO
From $744 per night (USD)
Expedia
**THE ADMIRAL'S ESTATE** Grand Home & Pool + LAST KEY SERVICES...
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Like many hig ...
From $744 per night (USD)
Expedia
From $465 per night (USD)
VRBO
Steps from Duval, Shared Pool – Sky Loft Downtown
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Experience the best of Key West from Sky Loft, your perfect weekend getaway! Just one block from the iconic Duv ...
From $465 per night (USD)
VRBO
From $3474 per night (USD)
Expedia
Takeover at the Grand Maloney
Bedrooms:
6
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 $3474 per night (USD)
Expedia
From $368 per night (USD)
VRBO
NEW LISTING 2nd Fl Condo w/private outdoor deck overlooking historic Fleming St.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Airy sun-filled apartment above an art gallery in 100 year old Old Town Conch home. Private cozy quiet & romantic hideaw ...
From $368 per night (USD)
VRBO
Click For Pricing
Expedia
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
Expedia
From $419 per night (USD)
VRBO
Come stay in an amazing house close to everything! Duvall! North Seaport!
Bedrooms:
2
Bathrooms:
3
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 $419 per night (USD)
VRBO
From $513 per night (USD)
Expedia
~ 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 $513 per night (USD)
Expedia
From $1751 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 $1751 per night (USD)
VRBO
From $653 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 $653 per night (USD)
Expedia
From $608 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 $608 per night (USD)
VRBO
From $696 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 $696 per night (USD)
Expedia
From $693 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 $693 per night (USD)
VRBO
From $689 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 $689 per night (USD)
Expedia
From $721 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 $721 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 $371 per night (USD)
Expedia
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)
Expedia
From $654 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 $654 per night (USD)
VRBO
From $1005 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 $1005 per night (USD)
Expedia
From $368 per night (USD)
VRBO
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 $368 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 ...
Click For Pricing
Expedia
From $710 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 $710 per night (USD)
VRBO
From $213 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 $213 per night (USD)
Expedia
$Spec.@159.+ 5-14 to 16 and 5-19 to 21 + extras Close to beach plus kitchen\n$
From $180 per night (USD)
VRBO
Spec.@159.+ 5-14 to 16 and 5-19 to 21 + extras Close to beach plus kitchen\n
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
ALSO WE'VE GOT YOUR BACK----ASK ABOUT OUR COVID & STORM POLICIES ...
From $180 per night (USD)
VRBO
From $788 per night (USD)
Expedia
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 $788 per night (USD)
Expedia
From $845 per night (USD)
VRBO
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 $845 per night (USD)
VRBO
From $936 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 $936 per night (USD)
Expedia
From $1098 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 $1098 per night (USD)
VRBO
$June Spec 129.+\n6-15 til 6-19 NEWLY Redone. Not shown in current pics\n$
From $172 per night (USD)
Expedia
June Spec 129.+\n6-15 til 6-19 NEWLY Redone. Not shown in current pics\n
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
New Pics coming soon. GREAT LOCATION Close to beach and All! REASONABLE RATES. W. KITCHEN AND PATIO Come splash in ...
From $172 per night (USD)
Expedia
From $723 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 $723 per night (USD)
VRBO
From $651 per night (USD)
Expedia
Curaçao Key West 2BR Condo w/ Pool&Waterfront Dock
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Time to relax! Bring your family & friends to this 1200 sqft Waterfront home - Stay spacious in Key West. Boat ...
From $651 per night (USD)
Expedia
$Downtown Key West 2BR/2BA•Pool, Dock, Pet \Aruba\$
From $656 per night (USD)
VRBO
Downtown Key West 2BR/2BA•Pool, Dock, Pet \"Aruba\"
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Enjoy true space in Key West! This 1,200 sq ft waterfront condo offers a full kitchen, dining area, living room ...
From $656 per night (USD)
VRBO
From $1615 per night (USD)
Expedia
St. Johns Waterfront 4BR Penthouse•Pool•Dock•Park
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
Summary: Bring the whole crew to this 2200 sqft waterfront penthouse—perfect for families & large groups! With 4 bedroom ...
From $1615 per night (USD)
Expedia
$Old Town \Eleuthera\ • 2BR Waterfront Corner Condo$
From $650 per night (USD)
VRBO
Old Town \"Eleuthera\" • 2BR Waterfront Corner Condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Bring friends and family to this updated 1,350 sqft waterfront corner condo in historic downtown Key West! Just ...
From $650 per night (USD)
VRBO
From $406 per night (USD)
Expedia
Our Piece of Paradise-
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Welcome to your ideal Key West getaway! Perfect for families and ideally situated between Old Town, New Town, and Duval ...
From $406 per night (USD)
Expedia
From $398 per night (USD)
VRBO
Midnight Cowboy by AvantStay | 3 Artistic Spaces
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
*Please note that this home is available for 28+ night stays only.* Midnight Cowboy is a one-of-a-kind Key West escape ...
From $398 per night (USD)
VRBO
From $207 per night (USD)
Expedia
Tennessee Williams by AvantStay | Funky Design + Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
*Please note that this home is available for 28+ night stays only.* Tennessee Williams is a one-of-a-kind Key West esca ...
From $207 per night (USD)
Expedia
From $904 per night (USD)
VRBO
Rooftop Penthouse, Walk to Duval - KAMP
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Stay in this one-of-a-kind penthouse and Jimmy Buffet's former Margaritaville Headquarters as well as David "Mr ...
From $904 per night (USD)
VRBO
From $376 per night (USD)
Expedia
The Elizabeth Suite | 1 bed, 1 bath w/shared pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
We are pleased to introduce The Elizabeth Suite at The Bayview House, a nightly rental with shared pool. One of 4 units ...
From $376 per night (USD)
Expedia
From $396 per night (USD)
VRBO
The Fleming Suite | 1 bed, 1 bath condo w/shared pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
We are pleased to introduce The Fleming Suite at The Bayview House, a 1-bedroom, 1-bathroom nightly rental with a shared ...
From $396 per night (USD)
VRBO
From $158 per night (USD)
Expedia
Breezy Key West First-Floor Condo w/ Pool Access
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Experience your next seaside vacation in style at this 2-bedroom, 2-bathroom Key West vacation rental. This 1st-floor co ...
From $158 per night (USD)
Expedia
From $389 per night (USD)
VRBO
Bohemian Retreat with Pool in Old Town Key West | Walk to Duval Street
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the heart of Old Town Key West! This hotel is located steps from Duval Street and Hemingway's home. Stroll to S ...
From $389 per night (USD)
VRBO
From $509 per night (USD)
Expedia
Romantic Key West Getaway with Heated Pool, Patio & Breakfast | Near Sunset Pier
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the heart of Old Town Key West! This hotel is located steps from Duval Street and Hemingway's home. Stroll to S ...
From $509 per night (USD)
Expedia
From $370 per night (USD)
VRBO
Quaint Bungalow w/ Private Outdoor Space Near Duval Street | Free Breakfast
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $370 per night (USD)
VRBO
From $515 per night (USD)
Expedia
Celebrate History in Key West: Tropical Bungalow Retreat Ideal for Relaxation
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $515 per night (USD)
Expedia
From $386 per night (USD)
VRBO
Serene Bungalow with Outdoor Pool Access | Near Historic Ernest Hemingway Museum
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $386 per night (USD)
VRBO
From $465 per night (USD)
Expedia
Romantic Getaway with Plush Turkish Robes & Inviting Pools Near Duval Street
Bedrooms:
1
Bathrooms:
1
Sleeps:
1
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $465 per night (USD)
Expedia
From $774 per night (USD)
VRBO
Key West Oasis: Retreat in Historical Bungalows with Pool Paradise
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $774 per night (USD)
VRBO
From $358 per night (USD)
Expedia
Serene Bungalow in Key West: Poolside Refreshers & Relaxing Amenities
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $358 per night (USD)
Expedia
From $455 per night (USD)
VRBO
Tranquil Bungalow w/ an Artistic Vibe in Vibrant Key West | Breakfast Included
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $455 per night (USD)
VRBO
From $386 per night (USD)
Expedia
Stylish Room in the Heart of Old Town w/ Access to Outdoor Pool | Free Breakfast
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $386 per night (USD)
Expedia
From $394 per night (USD)
VRBO
Historical Charm in a Room Surrounded by Key West's Best: Complimentary Breakfas
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $394 per night (USD)
VRBO
From $416 per night (USD)
Expedia
Bohemian Key West Boutique Inn with Pool & Free Breakfast | Near Sunset Pier
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the heart of Old Town Key West! This hotel is located steps from Duval Street and Hemingway's home. Stroll to S ...
From $416 per night (USD)
Expedia
From $861 per night (USD)
VRBO
Oceanfront Suite, Pier House, Serene Waterfront, Elegant Dining, Island Life
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $861 per night (USD)
VRBO
From $184 per night (USD)
Expedia
Southard Retreat- 2 bed 2 bath townhome downtown w/ 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 $184 per night (USD)
Expedia
Click For Pricing
VRBO
Studio Unit in quiet resort adjacent to Old Town Key West!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
With a coveted location in the heart of Old Town and magnificent views of the Gulf of Mexico, Sunset Harbor is the ultim ...
Click For Pricing
VRBO
From $281 per night (USD)
Expedia
Boomerang Boathouse in Key West
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Richley individual yet classic Key West are phrases that echo from Boomerang Boathouse, a 4 bedroom, 2.5 bath home with ...
From $281 per night (USD)
Expedia
From $534 per night (USD)
VRBO
Pool, Pet Friendly, & Near Duval - Coastal Rose
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Experience the charm of downtown Key West in this cozy 1-bedroom unit with an additional loft and a shared pool ...
From $534 per night (USD)
VRBO
From $462 per night (USD)
Expedia
Pet Friendly, Near Duval - Rose Petal Petite Suite
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Located in downtown Key West, the 'Rose Petal Petite Suite' offers a cozy and charming accommodation experience ...
From $462 per night (USD)
Expedia
From $819 per night (USD)
VRBO
Pet Friendly, & Near Duval - Rose Key Cottage
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Escape to paradise with this luxurious Key West retreat, perfect for families and groups looking to unwind in s ...
From $819 per night (USD)
VRBO
From $229 per night (USD)
Expedia
Casa Tranquila - Fully-Renovated 2-bedroom Townhome in Old Town Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Casa Tranquila! This 2-bedroom townhome is perfect for your escape to Key West. Located in Old Town just five ...
From $229 per night (USD)
Expedia
From $447 per night (USD)
VRBO
Modern Lodge w/ Outdoor Pool Near Attractions Ideal for Family Fun
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Discover Old Town charm, plunge into vibrant Duval Street life, and dive deep into Key West's treasures. We're footsteps ...
From $447 per night (USD)
VRBO
From $903 per night (USD)
Expedia
2 Rooms for the whole family w/ Pool access! Near Duval St. and Museums
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Discover Old Town charm, plunge into vibrant Duval Street life, and dive deep into Key West's treasures. We're footsteps ...
From $903 per night (USD)
Expedia
From $740 per night (USD)
VRBO
2 Bedroom Suite w/ Outdoor Pool in Old Town Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Discover Old Town charm, plunge into vibrant Duval Street life, and dive deep into Key West's treasures. We're footsteps ...
From $740 per night (USD)
VRBO
From $2674 per night (USD)
Expedia
Pool & Parking, & Near Duval - The Rigby House
Bedrooms:
6
Bathrooms:
6
Sleeps:
12
Summary: Escape to paradise with this stunning 6-bedroom, 6.5 bathroom home nestled in the heart of historic Key West. W ...
From $2674 per night (USD)
Expedia
From $893 per night (USD)
VRBO
Charming 2 room guest house, access to Pool, A/C, & WiFi, Key West, near Duval
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Key West is waiting for you at this clean & spacious 2-bedroom guest house. Good for up to 6 people. This cozy retreat o ...
From $893 per night (USD)
VRBO
From $2125 per night (USD)
Expedia
Spacious 5-bdrm 5 bathroom house in charming Key West with AC, WiFi, Plunge Pool
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Short walk to Duval Street. Central location. Restaurants nearby. Surrounded by charm of Key West. Explore the city the ...
From $2125 per night (USD)
Expedia
From $199 per night (USD)
VRBO
Chic 1BR w/ Balcony in Old Town – Walk to Duval!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Galveston Porches – Stylish One-Bedroom in the Heart of Old Town Key West Welcome to Galveston Porches, your perfect ho ...
From $199 per night (USD)
VRBO
From $1034 per night (USD)
Expedia
Charming Bungalow Perfect for Families and Couples': Escape in Old Town
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $1034 per night (USD)
Expedia
From $348 per night (USD)
VRBO
Discover this cozy retreat in the charm of Old Town Key West at Poorhouse Lane!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This 3-bedroom house is perfect for your escape to Key West. This cozy retreat offers prime location near all the action ...
From $348 per night (USD)
VRBO
From $203 per night (USD)
Expedia
Charming 1-bedroom apartment with WiFi, AC in delightful Key West Old Town
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Your Key West adventure begins at this fabulous 1-bedroom apartment. The cozy bedroom features a queen bed, perfect for ...
From $203 per night (USD)
Expedia
From $354 per night (USD)
VRBO
**SOUTHERN STAR @ THE MEADOWS** Private Home & Pool + LAST KEY SERVICES...
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! SOUTHERN STAR ...
From $354 per night (USD)
VRBO
From $125 per night (USD)
Expedia
Serene Key West Studio with Poolside Peace
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Studio Apartment for Rent in Key West This cozy studio apartment is located in a quiet, gated community on Grinnell Str ...
From $125 per night (USD)
Expedia

Search Your Destination Now!

Fleming Key Rentals

Rental Rates ($USD weekly)

Guests

Check Rates & Availability:

Results: 758 Rentals