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 $493 per night (USD)
VRBO
ABSOLUTE TRUMAN ANNEX in Key West
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
This Private home is located in the historic Truman Annex of old town Key West, where you can get away from it all while ...
From $493 per night (USD)
VRBO
$Paradise Island suite-2 bedroom 1 bath, a block off Duval St w\/pool, parking$
From $667 per night (USD)
Expedia
Paradise Island suite-2 bedroom 1 bath, a block off Duval St w\/pool, parking
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
AGE REQUIREMENT: ALL guests staying at the property MUST be 25 years of age or older at this property- NO EXCEPTIONS P ...
From $667 per night (USD)
Expedia
$Bimini suite-3 bedroom 3 bath, a block off Duval St w\/pool, parking$
From $763 per night (USD)
VRBO
Bimini suite-3 bedroom 3 bath, a block off Duval St w\/pool, parking
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
AGE REQUIREMENT: ALL guests staying at the property MUST be 25 years of age or older at this property- NO EXCEPTIONS P ...
From $763 per night (USD)
VRBO
From $524 per night (USD)
Expedia
Washer & Dryer, Near Downtown - Mesa House, Dos
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Summary: Whether you're lounging on the front porch or enjoying a seafood dinner inside, this 2-Bedroom Suite at The Mes ...
From $524 per night (USD)
Expedia
$Grand Bahama suite-3 bedroom 2 bath, a block off Duval St w\/pool, parking$
From $828 per night (USD)
VRBO
Grand Bahama suite-3 bedroom 2 bath, a block off Duval St w\/pool, parking
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
AGE REQUIREMENT: ALL guests staying at the property MUST be 25 years of age or older at this property- NO EXCEPTIONS P ...
From $828 per night (USD)
VRBO
$Nassau suite-2 bedroom 2 bath, a block off Duval St w\/pool, parking$
From $621 per night (USD)
Expedia
Nassau suite-2 bedroom 2 bath, a block off Duval St w\/pool, parking
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
AGE REQUIREMENT: ALL guests staying at the property MUST be 25 years of age or older at this property- NO EXCEPTIONS P ...
From $621 per night (USD)
Expedia
$Key West Retreat Near Duval Street | Scenic Resort w\/ Outdoor Pool$
From $871 per night (USD)
VRBO
Key West Retreat Near Duval Street | Scenic Resort w\/ Outdoor Pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $871 per night (USD)
VRBO
From $3040 per night (USD)
Expedia
Private Heated Pool & Near Duval - The Curry House
Bedrooms:
9
Bathrooms:
9
Sleeps:
18
Summary: "Curry House" provides three stories full of historic charm that take you back in time. This guesthouse has pr ...
From $3040 per night (USD)
Expedia
From $310 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 $310 per night (USD)
VRBO
From $470 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 $470 per night (USD)
Expedia
From $366 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 $366 per night (USD)
VRBO
From $345 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 $345 per night (USD)
Expedia
From $360 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 $360 per night (USD)
VRBO
From $386 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 $386 per night (USD)
Expedia
From $353 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 $353 per night (USD)
VRBO
From $321 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 $321 per night (USD)
Expedia
From $687 per night (USD)
VRBO
Sweet Caroline | Banana's Foster Guesthouse
Bedrooms:
3
Bathrooms:
3
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 $687 per night (USD)
VRBO
From $399 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 $399 per night (USD)
Expedia
From $367 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 $367 per night (USD)
VRBO
From $362 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 $362 per night (USD)
Expedia
From $453 per night (USD)
VRBO
Banana Split | Banana's Foster Guesthouse
Bedrooms:
1
Bathrooms:
2
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 $453 per night (USD)
VRBO
From $403 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 $403 per night (USD)
Expedia
From $798 per night (USD)
VRBO
Exquisite Elegance in Old Town Key West: Your Stylish Sanctuary Awaits
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
This stylish Conch home is tucked away on a quiet lane in Old Town Key West. Newly remodeled, impressively decorated 3 B ...
From $798 per night (USD)
VRBO
From $281 per night (USD)
Expedia
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 $281 per night (USD)
Expedia
From $362 per night (USD)
VRBO
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 $362 per night (USD)
VRBO
From $362 per night (USD)
Expedia
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 $362 per night (USD)
Expedia
From $220 per night (USD)
VRBO
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 $220 per night (USD)
VRBO
$Colorful cottage w\/shared pool, central AC, washer\/dryer$
Click For Pricing
Expedia
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
Expedia
From $855 per night (USD)
VRBO
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)
VRBO
$Seafarer's Refuge: 3 Story spacious conch style home w\/ private pool & dock!$
From $1375 per night (USD)
Expedia
Seafarer's Refuge: 3 Story spacious conch style home w\/ private pool & dock!
Bedrooms:
4
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 $1375 per night (USD)
Expedia
From $394 per night (USD)
VRBO
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)
VRBO
From $304 per night (USD)
Expedia
Anchors Away - Old Town Key West
Bedrooms:
1
Bathrooms:
3
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)
Expedia
From $336 per night (USD)
VRBO
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 $336 per night (USD)
VRBO
From $334 per night (USD)
Expedia
**CASITA OLIVIETTA @ SOLARES HILL** Brand New Home & Private Pool + LAST KEY SER
Bedrooms:
5
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)
Expedia
$Captain's Daughter: Oversized home for the whole family w\/private pool & dock$
From $1464 per night (USD)
VRBO
Captain's Daughter: 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 $1464 per night (USD)
VRBO
From $1081 per night (USD)
Expedia
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 $1081 per night (USD)
Expedia
From $686 per night (USD)
VRBO
**THE ADMIRAL'S ESTATE** Grand Home & Pool + LAST KEY SERVICES...
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Like many hig ...
From $686 per night (USD)
VRBO
From $462 per night (USD)
Expedia
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 $462 per night (USD)
Expedia
From $3515 per night (USD)
VRBO
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 $3515 per night (USD)
VRBO
From $509 per night (USD)
Expedia
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 $509 per night (USD)
Expedia
From $350 per night (USD)
VRBO
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)
VRBO
From $638 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 $638 per night (USD)
Expedia
From $455 per night (USD)
VRBO
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)
VRBO
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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 $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
From $805 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 $805 per night (USD)
Expedia
$CEASAR'S PARADISE - A MODERN LUXURY RETREAT W\/ 4+ Bedrooms\/ 5.5 Baths$
From $667 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 $667 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 $696 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 $696 per night (USD)
VRBO
From $953 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 $953 per night (USD)
Expedia
$Casa Rosa: 4BR\/4BA house, pool, near Duval$
From $733 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 $733 per night (USD)
VRBO
From $450 per night (USD)
Expedia
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)
Expedia
$Indoor \/ Outdoor Living in Old Key West$
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VRBO
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
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 $1084 per night (USD)
VRBO
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 $1084 per night (USD)
VRBO
From $915 per night (USD)
Expedia
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 $915 per night (USD)
Expedia
$SCARLET ~ Adult Only, 2nd Floor Suite, 1 Bedroom Unit w\/ Shared Pool!$
From $519 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 $519 per night (USD)
VRBO
Click For Pricing
Expedia
Fantasy Festival October 20, 2022-October 23, 2022 Studio Downtown Sunset Harbor
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Hyatt Residence Club Key West Sunset Harbor Fantasy Fest 2022 Location......Location, Location, Location....In the hear ...
Click For Pricing
Expedia
$**CASA SERENDIPITY @ OLD TOWN** Historic 3BR\/2BA Home & Pool + LAST KEY SERVICE$
From $1119 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 $1119 per night (USD)
VRBO
From $265 per night (USD)
Expedia
PEAK OF DUVAL | 2 Bed, 2 Bath
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This Elegant & Spacious Apartment is located directly in the center of the Famous Duval Street. Enjoy Dining, Shopping, ...
From $265 per night (USD)
Expedia
From $1249 per night (USD)
VRBO
Eisenhower Retreat: Conch style home in Oldtown with private pool AND dock!
Bedrooms:
4
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 $1249 per night (USD)
VRBO
From $1205 per night (USD)
Expedia
Bayview Retreat: Spacious Luxury Waterfront Home with Private Pool and Dock!
Bedrooms:
5
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 $1205 per night (USD)
Expedia
$NEWLY Redecorated as of 4-15-25. The current pics. do not reflect the changes\n$
From $177 per night (USD)
VRBO
NEWLY Redecorated as of 4-15-25. The current pics. do not reflect the changes\n
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
NEWLY REDECORATED AS OF APRIL 15. 2025 all dark natural wood walls and cabinets gone instead painted off-white color th ...
From $177 per night (USD)
VRBO
From $723 per night (USD)
Expedia
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)
Expedia
$Spec. 4-29 &4-30 169.00 lodg. + extras Close to beach plus kitchen\n$
From $209 per night (USD)
VRBO
Spec. 4-29 &4-30 169.00 lodg. + 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 $209 per night (USD)
VRBO
From $786 per night (USD)
Expedia
The Gideon Lowe House - Old Town Key West
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Elegance, Sophistication, Perfection! Nothing compares to this extraordinary Old Town Key West residence. It exudes ch ...
From $786 per night (USD)
Expedia
From $975 per night (USD)
VRBO
Island Chic: Luxury 3-Bedroom Waterfront Home with Private Pool AND Dock!
Bedrooms:
5
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 $975 per night (USD)
VRBO
$Curaçao Key West 2BR Condo w\/ Pool&Waterfront Dock$
From $395 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 $395 per night (USD)
Expedia
$Downtown Key West 2BR\/2BA•Pool, Dock, Pet \Aruba\$
From $622 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 $622 per night (USD)
VRBO
From $1925 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 $1925 per night (USD)
Expedia
$Old Town \Eleuthera\ • 2BR Waterfront Corner Condo$
From $703 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 $703 per night (USD)
VRBO
From $405 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 $405 per night (USD)
Expedia
From $461 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 $461 per night (USD)
VRBO
From $213 per night (USD)
Expedia
Tennessee Williams by AvantStay | Funky Design + Pool
Bedrooms:
3
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 $213 per night (USD)
Expedia
From $920 per night (USD)
VRBO
Rooftop Penthouse, Walk to Duval - KAMP
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Stay in this one-of-a-kind penthouse and Jimmy Buffet's former Margaritaville Headquarters as well as David "Mr ...
From $920 per night (USD)
VRBO
$The Elizabeth Suite | 1 bed, 1 bath w\/shared pool$
From $401 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 $401 per night (USD)
Expedia
$The Fleming Suite | 1 bed, 1 bath condo w\/shared pool$
From $401 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 $401 per night (USD)
VRBO
$Breezy Key West First-Floor Condo w\/ Pool Access$
From $158 per night (USD)
Expedia
Breezy Key West First-Floor Condo w\/ Pool Access
Bedrooms:
2
Bathrooms:
3
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 $1674 per night (USD)
VRBO
4 Traditional Two Queen, Pier House Resort, Island Elegance, Duval St. Access
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $1674 per night (USD)
VRBO
From $594 per night (USD)
VRBO
One Bedroom Suite Queens, Pier House, Roomy Elegance, Beachside Bliss, Key West
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 $594 per night (USD)
VRBO
From $486 per night (USD)
VRBO
Serene Resort Room with Private Beach & Spa - Perfect Key West Escape
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 $486 per night (USD)
VRBO
From $610 per night (USD)
VRBO
One Bedroom Suite King, Pier House, Spacious Comfort, Spa Access, Ocean Breeze
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 $610 per night (USD)
VRBO
From $764 per night (USD)
VRBO
Oceanfront King, Pier House, Stunning Ocean Views, Plush King Bed, Duval Locale
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $764 per night (USD)
VRBO
From $480 per night (USD)
VRBO
Family-Friendly Key West Resort with Private Beach on Duval St.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $480 per night (USD)
VRBO
From $791 per night (USD)
VRBO
Inviting Key West Paradise Perfect for Couples - Spa & Oceanfront Views
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 $791 per night (USD)
VRBO
From $594 per night (USD)
VRBO
Relaxing Key West Haven with Full-Service Spa and Legendary Dining
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 $594 per night (USD)
VRBO
From $486 per night (USD)
VRBO
Lanai Two Queen, Pier House, Tropical Views, Beachfront Access, Key West Charm
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 $486 per night (USD)
VRBO
From $1256 per night (USD)
VRBO
3 Traditional Two Queen, Pier House Resort, Fine Dining, Near Mallory Square
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $1256 per night (USD)
VRBO
From $2052 per night (USD)
VRBO
3 Charming Resort Stays with Private Beach & Spa Treatments - Key West Retreat
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $2052 per night (USD)
VRBO
From $843 per night (USD)
VRBO
2 Traditional Two Queen, Pier House Resort, Beachside, Key West Vibe
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $843 per night (USD)
VRBO
From $655 per night (USD)
VRBO
Oceanfront Two Queen, Pier House, Beach Panorama, Custom Decor, Pet-Friendly
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 $655 per night (USD)
VRBO
From $1405 per night (USD)
VRBO
2 Oceanfront Two Queen, Pier House Resort, Beach Access, Pet-Friendly, Duval St.
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $1405 per night (USD)
VRBO
From $568 per night (USD)
VRBO
Key West Beachfront Accommodation - Ideal for Family Vacation Fun!
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $568 per night (USD)
VRBO
From $937 per night (USD)
VRBO
2 Serene Beachside Accommodations with Enhanced Spa Experience in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $937 per night (USD)
VRBO
From $1295 per night (USD)
VRBO
2 Sophisticated Resort Rooms Perfect for Family Relaxation! Spa Access
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $1295 per night (USD)
VRBO
From $522 per night (USD)
VRBO
Traditional King, Pier House, Classic Island Style, Fine Dining, Duval Street Proximity
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $522 per night (USD)
VRBO
From $596 per night (USD)
VRBO
Pure Wellness Spa Junior Suite, Pier House, Private Beach Access, Duval St.
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $596 per night (USD)
VRBO
From $422 per night (USD)
VRBO
Beachfront Bliss with Water Activities & Next to Vibrant Nightlife Attractions
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 $422 per night (USD)
VRBO
From $711 per night (USD)
VRBO
Unique Island-Style Rooms with Custom Furniture & Art in Key West
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 $711 per night (USD)
VRBO
From $663 per night (USD)
VRBO
Pet-Friendly Coastal Retreat in Key West with Private Beach Access
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 $663 per night (USD)
VRBO

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