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 $1771 per night (USD)
VRBO
Commodore's Cove by Brightwild | Epic Location!
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
Summary: Commodore's Cove offers the best of Key West: a prime location and all the amenities of home. Up to 12 can stay ...
From $1771 per night (USD)
VRBO
From $2247 per night (USD)
Expedia
Commodore's Compound by Brightwild | HUGE Home!
Bedrooms:
7
Bathrooms:
8
Sleeps:
24
Summary: Welcome to Commodore's Compound, an incredible 8 bed, 7 bath home in prime location situated just one short blo ...
From $2247 per night (USD)
Expedia
From $1765 per night (USD)
VRBO
Seaport Suite by Brightwild | 2nd Story Hideaway!
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Summary: Situated in the heart of Old Town Key West, Seaport Suite is the perfect vacation spot for large groups of up t ...
From $1765 per night (USD)
VRBO
From $1857 per night (USD)
Expedia
Conch Cove | Heated Pool & Prime Location!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Summary: Conch Cove is a true Key West oasis! Nestled away off of Simonton St, this 3 bed 3 bath home sits just 1 short ...
From $1857 per night (USD)
Expedia
From $360 per night (USD)
VRBO
Conch House in the Historic District
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Discover a piece of paradise with a beautiful conch home located in the historic district of Key West. 4-bedrooms, 2 ba ...
From $360 per night (USD)
VRBO
$Luxury Galleon Resort & Marina 2 Bed\/2 Bath Marina View$
Click For Pricing
Expedia
Luxury Galleon Resort & Marina 2 Bed\/2 Bath Marina View
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The Galleon Resort is located in the heart of Old Town Key West and the Marina is one of the most desired harbors in the ...
Click For Pricing
Expedia
$**THE LIME & THE COCONUT @ OLD TOWN** 6BR\/6BA Compound + LAST KEY SERVICES..$
From $1792 per night (USD)
VRBO
**THE LIME & THE COCONUT @ OLD TOWN** 6BR\/6BA Compound + LAST KEY SERVICES..
Bedrooms:
8
Bathrooms:
6
Sleeps:
16
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! According to ...
From $1792 per night (USD)
VRBO
From $1715 per night (USD)
Expedia
**GRAND KEY OASIS @ THE ANNEX** Magnificent Estate & Pool + LAST KEY SERVICES…
Bedrooms:
6
Bathrooms:
5
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! The vacation ...
From $1715 per night (USD)
Expedia
From $137 per night (USD)
VRBO
The Estela, Old Town Key West Monthly Rental
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Tucked away just 1 block from the action of Duval Street lies our newest space located at 613 Fleming Street. Find your ...
From $137 per night (USD)
VRBO
From $394 per night (USD)
Expedia
Conch Republic Consul General's Cottage.-Historic District
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Stay in the Conch Republic Consul General's Cottage. Historic Carriage House is located a few blocks from famous Duval S ...
From $394 per night (USD)
Expedia
From $369 per night (USD)
VRBO
Conch Republic Consul General's Cottage.-Pool-No Contact Check-In
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Stay in the Conch Republic Consul General's Cottage. This one bedroom cottage is located in the historic district and o ...
From $369 per night (USD)
VRBO
From $583 per night (USD)
Expedia
ABSOLUTE KEY WEST in Truman Annex
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 $583 per night (USD)
Expedia
$Paradise Island suite-2 bedroom 1 bath, a block off Duval St w\/pool, parking$
From $685 per night (USD)
VRBO
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 must be 25 years of age or older at this property- NO EXCEPTIONS RESTRICTIONS: We do not ...
From $685 per night (USD)
VRBO
$Bimini suite-3 bedroom 3 bath, a block off Duval St w\/pool, parking$
From $1296 per night (USD)
Expedia
Bimini suite-3 bedroom 3 bath, a block off Duval St w\/pool, parking
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
AGE REQUIREMENT: All guests must be 25 years of age or older at this property- NO EXCEPTIONS RESTRICTIONS: We do not ...
From $1296 per night (USD)
Expedia
From $899 per night (USD)
VRBO
Mesa House, Dos by Brightwild | Unreal Location
Bedrooms:
1
Bathrooms:
2
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 $899 per night (USD)
VRBO
$Grand Bahama suite-3 bedroom 2 bath, a block off Duval St w\/pool, parking$
From $1243 per night (USD)
Expedia
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 must be 25 years of age or older at this property- NO EXCEPTIONS RESTRICTIONS: We do not ...
From $1243 per night (USD)
Expedia
$Nassau suite-2 bedroom 2 bath, a block off Duval St w\/pool, parking$
From $701 per night (USD)
VRBO
Nassau suite-2 bedroom 2 bath, a block off Duval St w\/pool, parking
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
AGE REQUIREMENT: All guests must be 25 years of age or older at this property- NO EXCEPTIONS RESTRICTIONS: We do not ...
From $701 per night (USD)
VRBO
From $549 per night (USD)
VRBO
Dream Vacation! Near The Famous Duval Street!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $549 per night (USD)
VRBO
Click For Pricing
VRBO
Amazing Vacation for 16 Guests! 3 Pools, Onsite Dining Pets Allowed!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
Click For Pricing
VRBO
From $641 per night (USD)
Expedia
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 $641 per night (USD)
Expedia
From $3707 per night (USD)
VRBO
The Curry House by Brightwild | Historic Guesthome
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 $3707 per night (USD)
VRBO
From $329 per night (USD)
Expedia
Curry House #6 by Brightwild | King Bed, Pool
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 guest ...
From $329 per night (USD)
Expedia
From $588 per night (USD)
VRBO
Curry House by Brightwild | Balcony & Pool -Rm 3&4
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: "Curry House" provides three stories full of historic charm that take you back in time. This guesthouse has pr ...
From $588 per night (USD)
VRBO
From $357 per night (USD)
Expedia
Curry House Room 1 | Heated Pool & Balcony
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 $357 per night (USD)
Expedia
From $343 per night (USD)
VRBO
Curry House #8 by Brightwild | King Bed, Balcony
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 $343 per night (USD)
VRBO
From $363 per night (USD)
Expedia
Curry House #7 by Brightwild | King Bed, Balcony
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 $363 per night (USD)
Expedia
From $351 per night (USD)
VRBO
Curry House #2 by Brightwild | Balcony & Pool
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 $351 per night (USD)
VRBO
From $309 per night (USD)
Expedia
Curry House by Brightwild | Heated Pool - Rm #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 $309 per night (USD)
Expedia
From $370 per night (USD)
VRBO
Curry House Room 5 | 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 $370 per night (USD)
VRBO
From $668 per night (USD)
Expedia
Sweet Caroline by Brightwild | Pool & Parking
Bedrooms:
3
Bathrooms:
2
Sleeps:
7
Summary: Banana's Foster Guest House is a charming, historic home situated in the heart of Key West. This unique old con ...
From $668 per night (USD)
Expedia
From $405 per night (USD)
VRBO
Key Lime Cottage | Pool, Parking, Steps to Duval!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Banana's Foster Guest House is a charming, historic home situated in the heart of Key West. This unique old con ...
From $405 per night (USD)
VRBO
From $342 per night (USD)
Expedia
Sugar Pie Suite by Brightwild | Pool & Grill
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Banana's Foster Guest House is a charming, historic home situated in the heart of Key West. This unique old con ...
From $342 per night (USD)
Expedia
From $287 per night (USD)
VRBO
Honey Bun Hideaway | Heated Pool, Steps to Duval!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Banana's Foster Guest House is a charming, historic home situated in the heart of Key West. This unique old con ...
From $287 per night (USD)
VRBO
From $477 per night (USD)
Expedia
Banana Split by Brightwild | Pool & Grill
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Banana's Foster Guest House is a charming, historic home situated in the heart of Key West. This unique old con ...
From $477 per night (USD)
Expedia
From $365 per night (USD)
VRBO
Creme Brulee Suite | Steps to Duval, Pvt Parking!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Banana's Foster Guest House is a charming, historic home situated in the heart of Key West. This unique old con ...
From $365 per night (USD)
VRBO
From $303 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 $303 per night (USD)
Expedia
From $603 per night (USD)
VRBO
Carriage House at Grand Maloney by Brightwild
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 $603 per night (USD)
VRBO
From $552 per night (USD)
Expedia
Bunk Room at the Grand Maloney by Brightwild
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 $552 per night (USD)
Expedia
From $300 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 $300 per night (USD)
VRBO
$Colorful cottage w\/shared pool, central AC, washer\/dryer$
From $310 per night (USD)
Expedia
Colorful cottage w\/shared pool, central AC, washer\/dryer
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Grinnell Street Getaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $310 per night (USD)
Expedia
From $703 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 $703 per night (USD)
VRBO
$Seafarer's Refuge: 3 Story spacious conch style home w\/ private pool & dock!$
From $1761 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 $1761 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:
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)
Expedia
From $357 per night (USD)
VRBO
Red Room at Grand Maloney Hotel with Pool!
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 $357 per night (USD)
VRBO
From $469 per night (USD)
Expedia
Harbor Walk Hideaways - African Queen Suite | Downtown
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: African Queen Cottage is part of the quiet complex called "Harbor Walk Hideaways," located in the Historic Seap ...
From $469 per night (USD)
Expedia
From $316 per night (USD)
VRBO
Harbor Walk Hideaways - The Pilar's Cottage | Downtown with Pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Pilar Cottage is part of the quiet complex called "Harbor Walk Hideaways," located in the Historic Seaport dist ...
From $316 per night (USD)
VRBO
From $1361 per night (USD)
Expedia
Harbor Walk Hideaways - Full Compound|Downtown with Pool
Bedrooms:
3
Bathrooms:
4
Sleeps:
14
Summary: Harborwalk Hideaways is a stunning, newly-renovated vacation rental complex tucked away in the Historic Seaport ...
From $1361 per night (USD)
Expedia
From $313 per night (USD)
VRBO
**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 30 days prior to your arrival! You don’t oft ...
From $313 per night (USD)
VRBO
$Captain's Daughter: Oversized home for the whole family w\/private pool & dock$
From $2213 per night (USD)
Expedia
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 $2213 per night (USD)
Expedia
From $1130 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 $1130 per night (USD)
VRBO
From $733 per night (USD)
Expedia
**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 30 days prior to your arrival! Like many hig ...
From $733 per night (USD)
Expedia
From $621 per night (USD)
VRBO
Sky Loft by Brightwild | Penthouse in Prime Spot!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: This gem of a top floor apartment is perfect for your weekend getaway. Sky Loft is located just one block away ...
From $621 per night (USD)
VRBO
From $4146 per night (USD)
Expedia
Takeover at the Grand Maloney by Brightwild
Bedrooms:
7
Bathrooms:
6
Sleeps:
16
Summary: The Grand Maloney Hotel is a new boutique hotel located in the heart of downtown Key West. Our signature red br ...
From $4146 per night (USD)
Expedia
Click For Pricing
Expedia
Banyan Resort - 2 Blocks to Sunset Celebration
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The Banyan Resort is the ultimate destination for a weekend get-a-way or long term accommodations in our well appointed ...
Click For Pricing
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
From $432 per night (USD)
VRBO
Come stay in an amazing house close to everything! Duvall! North Seaport!
Bedrooms:
3
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 $432 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 $899 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 $899 per night (USD)
VRBO
From $146 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 $146 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 $986 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 $986 per night (USD)
Expedia
$CEASAR'S PARADISE - A MODERN LUXURY RETREAT W\/ 4+ Bedrooms\/ 5.5 Baths$
From $750 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 $750 per night (USD)
VRBO
From $753 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 $753 per night (USD)
Expedia
From $820 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 $820 per night (USD)
VRBO
From $399 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 $399 per night (USD)
Expedia
From $571 per night (USD)
VRBO
1 BLOCK OFF DUVAL! PRIVATE POOL AND HOT TUB
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Enjoy one of Old Town's wonderful historic homes with private pool and hot tub. Casa Rosa one of only seventy five remai ...
From $571 per night (USD)
VRBO
$Sunny, Dog-Friendly Historical Home w\/ Private Hot Tub, Central AC, WiFi, & W\/D$
Click For Pricing
Expedia
Sunny, Dog-Friendly Historical Home w\/ Private Hot Tub, Central AC, WiFi, & W\/D
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Casa Eloise Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
Click For Pricing
Expedia
From $338 per night (USD)
VRBO
Sweet Caroline Historic Seaport Key West Home Rental Floor 2
Bedrooms:
3
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 $338 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:
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
Expedia
From $331 per night (USD)
VRBO
Dream Vacation! Near Famous Duval Street!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $331 per night (USD)
VRBO
From $743 per night (USD)
Expedia
~Butterfly Cottage~ Enjoy a hot tub, gourmet kitchen, and 2 king ensuites.
Bedrooms:
3
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 $743 per night (USD)
Expedia
From $176 per night (USD)
VRBO
Ella Varela: Gorgeous Conch Cottage in Key West's Heart, Close to Old Town & Beaches, Dog-Friendly!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to Ella Varela, a beautifully updated Conch Cottage nestled in the heart of Key West, where your furry friend is ...
From $176 per night (USD)
VRBO
$SCARLET ~ Adult Only, 2nd Floor Suite, 1 Bedroom Unit w\/ Shared Pool!$
From $774 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 $774 per night (USD)
Expedia
From $1778 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 $1778 per night (USD)
VRBO
From $2024 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 $2024 per night (USD)
Expedia
From $208 per night (USD)
VRBO
Varela Street Retreat. $99 spec.+ extras. some dates in Aug. +Sept.
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
GREAT LOCATION Close to beach and All! REASONABLE RATES. W. KITCHEN AND PATIO Come splash in the surf. Come soak up the ...
From $208 per night (USD)
VRBO
From $627 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 $627 per night (USD)
Expedia
Click For Pricing
VRBO
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
VRBO
$**CASA SERENDIPITY @ OLD TOWN** Historic 3BR\/2BA Home & Pool + LAST KEY SERVICE$
From $1092 per night (USD)
Expedia
**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 $1092 per night (USD)
Expedia
From $426 per night (USD)
VRBO
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 $426 per night (USD)
VRBO
$Key West Retreat $99.Spec.+extras some dates in Aug & Sept.\n$
From $194 per night (USD)
Expedia
Key West Retreat $99.Spec.+extras some dates in Aug & Sept.\n
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
ALSO WE'VE GOT YOUR BACK----ASK ABOUT OUR COVID & STORM POLICIES ...
From $194 per night (USD)
Expedia
From $833 per night (USD)
VRBO
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 $833 per night (USD)
VRBO
From $1497 per night (USD)
Expedia
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 $1497 per night (USD)
Expedia
From $1166 per night (USD)
VRBO
Authentic Key West Adventure! 3 Comfortable Units, 3 Pools, Pets Allowed!
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $1166 per night (USD)
VRBO
From $1588 per night (USD)
VRBO
Family and Friends Getaway! 4 Comfortable Units, 3 Pools, Onsite Dining!
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $1588 per night (USD)
VRBO
$Large 2\/2 Waterfront Condo Great View Pool & Dock$
From $690 per night (USD)
VRBO
Large 2\/2 Waterfront Condo Great View Pool & Dock
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Time to relax! Bring your family & friends to this 1200 sqft Waterfront home. Boat slips available on site with ...
From $690 per night (USD)
VRBO
$Aruba - Downtown Waterfront 2\/2 Dock, Pool, Pet$
From $703 per night (USD)
VRBO
Aruba - Downtown Waterfront 2\/2 Dock, Pool, Pet
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Time to relax! Bring your family & friends to this 1200 sqft Waterfront home. Boat slips available on site with ...
From $703 per night (USD)
VRBO
From $700 per night (USD)
VRBO
Downtown Waterfront Penthouse Pool, Parking, Dock
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
Summary: Bring your family & friends to this 2200sqft waterfront Penthouse condo. Endless water views from one of the t ...
From $700 per night (USD)
VRBO
$2\/2 Fully Updated Old Town Waterfront Corner Condo$
From $437 per night (USD)
VRBO
2\/2 Fully Updated Old Town Waterfront Corner Condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Time to relax! Bring your family & friends to this fully updated 1350sqft Waterfront corner condo home. Boat sl ...
From $437 per night (USD)
VRBO
From $1090 per night (USD)
VRBO
Downtown Duval Street Penthouse- Private Pool-Parking-Roof Deck- Walk Everywhere
Bedrooms:
3
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 $1090 per night (USD)
VRBO
From $1347 per night (USD)
Expedia
The Mesa House by Brightwild | Close to Duval!
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 $1347 per night (USD)
Expedia
From $153 per night (USD)
VRBO
Sunny Apartment with a Large Deck and Great View
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Charming 1 bedroom second floor apartment with a large deck space for dining, sunbathing or watching sunsets. In residen ...
From $153 per night (USD)
VRBO
From $433 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 $433 per night (USD)
Expedia
From $597 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 $597 per night (USD)
VRBO
From $244 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 $244 per night (USD)
Expedia
From $1036 per night (USD)
VRBO
KAMP by Brightwild | Rooftop Penthouse On Duval
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 $1036 per night (USD)
VRBO
From $395 per night (USD)
Expedia
The Elizabeth #1 Suite | 1 Bed, 1 Bath
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. Located in ...
From $395 per night (USD)
Expedia
From $799 per night (USD)
VRBO
The Fleming #3 Suite | 1 Bed, 1 Bath
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. Located in ...
From $799 per night (USD)
VRBO
$Breezy Key West First-Floor Condo w\/ Pool Access$
From $277 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 $277 per night (USD)
Expedia

Search Your Destination Now!

Fleming Key Rentals

Rental Rates ($USD weekly)

Guests

Check Rates & Availability:

Results: 864 Rentals