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

$**OLD TOWN OASIS @ THE ANNEX** Oceanside 2BR\/2BA Condo & Pool + LAST KEY SERVICE$
From $876 per night (USD)
VRBO
**OLD TOWN OASIS @ THE ANNEX** Oceanside 2BR\/2BA Condo & Pool + LAST KEY SERVICE
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! OLD TOWN OASI ...
From $876 per night (USD)
VRBO
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Expedia
Cozy studio cottage in Old Town Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Cute Studio cottage with additional sleeping loft. Nicely landscaped shared pool and outside area. Walking distance to ...
Click For Pricing
Expedia
From $1006 per night (USD)
VRBO
Heart of Key West - 2BR Waterfront at the Galleon Resort
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Located in the heart of Old Town Key West. This resort overlooks the Gulf of Mexico with a private marina, private beach ...
From $1006 per night (USD)
VRBO
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Expedia
Little Casita: Key West Monthly rental Close to Duval - RealKeyWest
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
WELCOME TO LITTLE CASITA! If looking for the perfect couple’s retreat, look no further! This one bedroom, one bath hi ...
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Expedia
From $469 per night (USD)
VRBO
Welcome to the Shady Palms - Private Pool - RealKeyWest
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Step into this beautifully restored and redecorated 1933 Key West home. This first-floor home has Bahama shutters throug ...
From $469 per night (USD)
VRBO
$ISLAND TIME - 5 Bed\/3 Bath OldTown Complex - MONTHLY - Private pool$
From $779 per night (USD)
Expedia
ISLAND TIME - 5 Bed\/3 Bath OldTown Complex - MONTHLY - Private pool
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
WELCOME TO ISLAND TIME! Key West Island Time is a rare find in old town Key West. It is a total of 5 bedrooms and three ...
From $779 per night (USD)
Expedia
From $374 per night (USD)
VRBO
TROPICAL PROPERTIES VACATION RENTAL - KEY WEST
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
****This property requires a minimum stay of 28 nights in the same calendar month**** ***Brand New Pool with waterfall, ...
From $374 per night (USD)
VRBO
$Tropical Jewel: Historic Seaport Oldtown - 2BR\/2BA - Pool - RealKeyWest$
From $308 per night (USD)
Expedia
Tropical Jewel: Historic Seaport Oldtown - 2BR\/2BA - Pool - RealKeyWest
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
WELCOME TO TROPICAL JEWEL! Near all the action of the historic seaport and Duval Street, you can get out into the cit ...
From $308 per night (USD)
Expedia
$Getaway in Key West: Tranquil Room w\/ Balcony | Resort w\/ Pool Access$
From $686 per night (USD)
VRBO
Getaway in Key West: Tranquil Room w\/ Balcony | Resort w\/ Pool Access
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 $686 per night (USD)
VRBO
$Old Town Key West Family Retreat | Spacious Room w\/ Balcony | Parking Onsite$
From $848 per night (USD)
VRBO
Old Town Key West Family Retreat | Spacious Room w\/ Balcony | Parking Onsite
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $848 per night (USD)
VRBO
From $693 per night (USD)
VRBO
Casa Verde - Perfection in a monthly rental - private pool - RealKeyWest
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
As you step through the door, you are enveloped in a serene atmosphere highlighted by soothing tropical colors and impre ...
From $693 per night (USD)
VRBO
From $473 per night (USD)
Expedia
**SEAPORT SENSATION @ OLD TOWN VILLAS** Condo & Pool + LAST KEY SERVICES...
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! It is not so ...
From $473 per night (USD)
Expedia
From $515 per night (USD)
VRBO
**COASTAL LOVING @ OLD TOWN** Chic 4BR 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! If you’re loo ...
From $515 per night (USD)
VRBO
From $514 per night (USD)
Expedia
Runaway Bills | 3 Bed, 1 Bath
Bedrooms:
1
Bathrooms:
4
Sleeps:
6
This stylish Conch Home is tucked away on a quiet lane in Old Town Key West. Surrounded by distinctive neighborhoods thi ...
From $514 per night (USD)
Expedia
From $480 per night (USD)
VRBO
Sunset South: First Floor 2 Bedroom 1 Bath Condo at Bayfront Suites & Marina
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $480 per night (USD)
VRBO
From $433 per night (USD)
Expedia
Sunset views at the Galleon
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
You will be back year after year! Unit features full kitchen with Master King, Guest Twin Beds, and Pull out Sleeper Sof ...
From $433 per night (USD)
Expedia
From $988 per night (USD)
VRBO
Upper Bayview North: Waterfront 4 Bedroom Condo at Bayfront Suites & Marina
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $988 per night (USD)
VRBO
From $547 per night (USD)
Expedia
~HORSE CONCH~ Amazing location with shared pool and covered balcony!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
THE PROPERTY: Enjoy your stay in the tropics at Horse Conch, part of the highly touted "Queen Conch" complex, which incl ...
From $547 per night (USD)
Expedia
From $1097 per night (USD)
VRBO
Upper Bayview South: Waterfront 4 Bedroom Condo at Bayfront Suites & Marina
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $1097 per night (USD)
VRBO
From $830 per night (USD)
Expedia
Middle Sunset: 3 Bedroom 3 Bath Luxury Condo at Bayfront Suites & Marina
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $830 per night (USD)
Expedia
From $972 per night (USD)
VRBO
Bayview North One: Waterfront 4 Bedroom 4 Bath Condo at Bayfront Suites
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $972 per night (USD)
VRBO
From $782 per night (USD)
Expedia
Sunset North: Luxury 4 Bedroom 4.5 Bath Condo at Bayfront Suites & Marina
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $782 per night (USD)
Expedia
From $841 per night (USD)
VRBO
Upper Sunset South: Luxury 3 Bedroom Condo at Bayfront Suites & Marina
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $841 per night (USD)
VRBO
From $958 per night (USD)
Expedia
Bayview South: 4 Bedroom 3 Bath Waterfront Condo at Bayfront Suites & Marina
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $958 per night (USD)
Expedia
From $854 per night (USD)
VRBO
Upper Sunset North: Luxury 4 Bedroom Condo at Bayfront Suites & Marina
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $854 per night (USD)
VRBO
From $931 per night (USD)
Expedia
Bayview Middle: Waterfront 3 Bedroom Condo at Bayfront Suites & Marina
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $931 per night (USD)
Expedia
From $178 per night (USD)
VRBO
coral stone
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Our apartment offers all the comforts of home, 120 paces to Duval Street - shopping, restaurants and nightlife. Near Hem ...
From $178 per night (USD)
VRBO
From $320 per night (USD)
VRBO
Seaport Walkabout- the best location in town
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Open to annual rental at lower rate Two hundred yards from Schooner Wharf and the seaport and steps from Pepe’s in the ...
From $320 per night (USD)
VRBO
From $233 per night (USD)
VRBO
Lush Gardens-Pool-Jacuzzi-No Contact Check-In
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
This 3 bedroom home is located one block from where Tennessee Williams home was located. The home has a true historic fl ...
From $233 per night (USD)
VRBO
From $306 per night (USD)
Expedia
Petite Pearl! Spacious 1 Bedroom, 1 Bath Pool Condo- RealKeyWest
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to Petite Pearl, your hidden gem nestled in the heart of the coveted Meadows district in Key West. A stone's thr ...
From $306 per night (USD)
Expedia
From $556 per night (USD)
VRBO
~POINCIANA GARDEN~ Casual 1st floor duplex 2 blocks from Duval Street!
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
THE PROPERTY: Located on a teeny tiny quiet lane, this comfortably furnished first-floor duplex home comes with Key West ...
From $556 per night (USD)
VRBO
From $382 per night (USD)
Expedia
**HAVANA HOUSE @ OLD TOWN** Elegant Cottage Near Duval + LAST KEY SERVICES...
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Located on So ...
From $382 per night (USD)
Expedia
From $1926 per night (USD)
VRBO
**AMERICANA TROPICALE @ OLD TOWN** Home & Pool by Duval + LAST KEY SERVICES...
Bedrooms:
5
Bathrooms:
4
Sleeps:
10
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! For the ultim ...
From $1926 per night (USD)
VRBO
From $2741 per night (USD)
Expedia
**THE IBIS & THE CRANE @ OLD TOWN** Compound Near Duval + 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! Dreaming of a ...
From $2741 per night (USD)
Expedia
From $987 per night (USD)
VRBO
Find Sanity in the Heart of Key West
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Experience the charm of this fantastic Old Town location surrounded by local businesses and restaurants, allowing you to ...
From $987 per night (USD)
VRBO
From $1345 per night (USD)
Expedia
**PUERTA CORALINA @ OLD TOWN** Cottage Near Duval + LAST KEY SERVICE...
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! This precious ...
From $1345 per night (USD)
Expedia
From $2708 per night (USD)
VRBO
**CASA VICTORIA @ OLD TOWN** Historic 5BR Home & Pool + LAST KEY SERVICES...
Bedrooms:
6
Bathrooms:
5
Sleeps:
12
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! CASA VICTORIA ...
From $2708 per night (USD)
VRBO
From $555 per night (USD)
Expedia
**THE ARTISTS' MUSE @ LOVE LANE** Immaculate 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! For many, the ...
From $555 per night (USD)
Expedia
From $1479 per night (USD)
VRBO
**THE SMILING IBIS @ OLD TOWN** Home & Pool Near Duval + LAST KEY SERVICES...
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Traveling to ...
From $1479 per night (USD)
VRBO
From $899 per night (USD)
Expedia
ROOFTOP PENTHOUSE- | 2 Bed, 1.5 Bath
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The high-end sophisticated Rooftop Penthouse is located directly above the famous Wyland Gallery on Duval Street. Enjoy ...
From $899 per night (USD)
Expedia
From $463 per night (USD)
VRBO
**MAISON TROPICALE @ OLD TOWN** Historic Home + LAST KEY SERVICES...
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Imagine a tra ...
From $463 per night (USD)
VRBO
From $546 per night (USD)
Expedia
**VILLA OLIVIETTA @ SOLARES HILL** Upscale 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! This ultimate ...
From $546 per night (USD)
Expedia
From $1498 per night (USD)
VRBO
**THE CONTENTED CRANE @ OLD TOWN** Home & Pool Near Duval + LAST KEY SERVICES...
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Traveling to ...
From $1498 per night (USD)
VRBO
From $2783 per night (USD)
Expedia
**STAR OF THE SEAPORT @ OLD TOWN** Huge Home & Pool + LAST KEY SERVICES...
Bedrooms:
5
Bathrooms:
5
Sleeps:
12
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! For a truly o ...
From $2783 per night (USD)
Expedia
From $634 per night (USD)
VRBO
**CASA OLIVIANA @ SOLARES HILL** Grand Home & Pool + LAST KEY SERVICES...
Bedrooms:
5
Bathrooms:
6
Sleeps:
12
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Finally, a la ...
From $634 per night (USD)
VRBO
From $660 per night (USD)
Expedia
Bright Condo with Homey Feel, Entertainment & Private Parking - Beach Nearby
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Jasmine Suite Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $660 per night (USD)
Expedia
From $250 per night (USD)
VRBO
Breezy Florida Home with Shared Pool, Dog & Snowbird-Friendly - Walk to Beach
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
The Headquarters Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $250 per night (USD)
VRBO
$Dog-friendly home w\/ large private pool only a short walk to Historic Seaport$
From $337 per night (USD)
Expedia
Dog-friendly home w\/ large private pool only a short walk to Historic Seaport
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Seaport Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $337 per night (USD)
Expedia
$Old Town! Spacious Condo in Historic Home w\/Pool!$
From $259 per night (USD)
VRBO
Old Town! Spacious Condo in Historic Home w\/Pool!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Tony's Conch Retreat is a spacious updated condo is located in a historic home on William Street that was converted into ...
From $259 per night (USD)
VRBO
$Little Paradise, Historic Harbor Old Town Key West 2\/1.5$
From $551 per night (USD)
Expedia
Little Paradise, Historic Harbor Old Town Key West 2\/1.5
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Come enjoy Island Living at it’s finest, Your own “Little Paradise”. This Two Bedroom One and a half bath home is nestl ...
From $551 per night (USD)
Expedia
$Charming Condo w\/ Entertainment & Private Parking - Great In-Town Location$
From $672 per night (USD)
VRBO
Charming Condo w\/ Entertainment & Private Parking - Great In-Town Location
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Gardenia Getaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $672 per night (USD)
VRBO
From $495 per night (USD)
Expedia
Elegant Condo with Entertainment & Private Parking - Great Central Location
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Orchid Suite Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $495 per night (USD)
Expedia
From $318 per night (USD)
VRBO
Welcoming & Conveniently Located Dog-Friendly Home - Walk to Everything
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Olivia Street Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $318 per night (USD)
VRBO
From $482 per night (USD)
Expedia
Dog-friendly condo in prime location - walk to dining & sights, near the beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
The Frontier Suite Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $482 per night (USD)
Expedia
Click For Pricing
VRBO
Dante's Marina Townhouse 2 bed 1.5 bath unit with a 5 minute walk to Duval!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
A short walk, just blocks away from all the sought-after action on Duval Street and near the infamous Dante's Pool at th ...
Click For Pricing
VRBO
$Modern 2BR Condo Old Town\/Balcony & Pool$
From $194 per night (USD)
Expedia
Modern 2BR Condo Old Town\/Balcony & Pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
*28 day min stay* Come enjoy this fully updated 2/BR condo in the heart of Old Town. The perfect balance of being close ...
From $194 per night (USD)
Expedia
From $1079 per night (USD)
VRBO
Balcony on Duval - Duval Dream Loft
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Summary: Located right in the heart of the World Famous Duval Street, enjoy a true downtown Key West experience! This un ...
From $1079 per night (USD)
VRBO
From $892 per night (USD)
Expedia
Balcony on Duval - The Collins on Duval
Bedrooms:
1
Bathrooms:
3
Sleeps:
10
Summary: Located right in the heart of the World Famous Duval Street, enjoy a true downtown Key West experience! The Col ...
From $892 per night (USD)
Expedia
$7 Nights - Hyatt Sunset Harbor 2 bed\/2bath\/Kitchen\/Sleeps 6. Fantastic Location$
Click For Pricing
VRBO
7 Nights - Hyatt Sunset Harbor 2 bed\/2bath\/Kitchen\/Sleeps 6. Fantastic Location
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Fantastic location!!! Sunday to Sunday 7 night rental at HYATT SUNSET HARBOR 2 bedrooms 2 bath full kitchen and common a ...
Click For Pricing
VRBO
$Sunny Condo w\/ Entertainment, Balcony, & Great Location Near Beach - Dogs OK$
From $624 per night (USD)
Expedia
Sunny Condo w\/ Entertainment, Balcony, & Great Location Near Beach - Dogs OK
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The Frontier Flat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $624 per night (USD)
Expedia
From $2317 per night (USD)
VRBO
Balcony on Duval - Duval's Duet on Duval
Bedrooms:
2
Bathrooms:
6
Sleeps:
18
Summary: Located right in the heart of the World Famous Duval Street, enjoy a true downtown Key West experience! Duval's ...
From $2317 per night (USD)
VRBO
$Old Town home a short walk to Duval\/Couples Oasis$
From $301 per night (USD)
Expedia
Old Town home a short walk to Duval\/Couples Oasis
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summary: Add this listing to your wishlist by clicking the ♥ in the upper right hand corner. This 1 bedroom/1.5 bathroom ...
From $301 per night (USD)
Expedia
$Relaxing island home\/Great location\/Stylish$
From $357 per night (USD)
VRBO
Relaxing island home\/Great location\/Stylish
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summary: Only 4 short blocks to Duval, this 1 bedroom/1.5 bathroom home is walking distance to your favorite Key West sp ...
From $357 per night (USD)
VRBO
From $394 per night (USD)
Expedia
The Emelina, Key West Monthly Rental
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The Emelina is located in a beautiful historic home. This unit is luxuriously appointed with elegant materials and impe ...
From $394 per night (USD)
Expedia
From $180 per night (USD)
VRBO
NEW MONTHLY RENTAL, Old Town, Duplex, private backyard, pets welcome
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Sea Monkey and The Mermaid. Our home is a duplex located in Old Town and full of Key West charm. Walk to a ...
From $180 per night (USD)
VRBO
$Conch Cottage | 'Old Town' Home w\/ Shared Pool$
From $286 per night (USD)
Expedia
Conch Cottage | 'Old Town' Home w\/ Shared Pool
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Escape to this cozy Key West Cottage and enjoy all the island has to offer! Whether you plan to stay in or go o ...
From $286 per night (USD)
Expedia
From $692 per night (USD)
VRBO
Enjoy Old Town Key West in this Beautifully furnished house
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
We recently bought this house because we LOVE Key West! It is a 2 story Key West style house. The bedrooms are upstair ...
From $692 per night (USD)
VRBO
From $601 per night (USD)
Expedia
Yellow 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 $601 per night (USD)
Expedia
From $632 per night (USD)
VRBO
Blue 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 $632 per night (USD)
VRBO
From $630 per night (USD)
Expedia
Green Room at the Grand Maloney
Bedrooms:
1
Bathrooms:
2
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 $630 per night (USD)
Expedia
From $628 per night (USD)
VRBO
Poolside King Room Steps from Duval!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The Poolside King Room is a hotel-style room adjacent to the pool. It can sleep up to four persons, two in the king-size ...
From $628 per night (USD)
VRBO
From $494 per night (USD)
Expedia
Poolside Queen Room Steps from Duval!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The Poolside Queen Room is a hotel-style bedroom and bath unit that offers the amenities of our Key West villas for thos ...
From $494 per night (USD)
Expedia
From $621 per night (USD)
VRBO
One Bedroom Deck Villa Steps from Duval!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Enjoy a wonderful Key West accommodation. Our One Bedroom Deck Villa features a living room, a separate bedroom with ki ...
From $621 per night (USD)
VRBO
$MONTHLY RENTAL, Old Town, Duplex, private yard, 2 BR\/2 BA$
From $181 per night (USD)
Expedia
MONTHLY RENTAL, Old Town, Duplex, private yard, 2 BR\/2 BA
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Sea Monkey and The Mermaid! Our home is a duplex located in Old Town and full of Key West charm. Both unit ...
From $181 per night (USD)
Expedia
From $619 per night (USD)
VRBO
Galleon Resort beach hotel luxury in Old Town Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
This is a large (1245 SF) 1BR/1BA condo on the 6th floor of the Galleon Resort & Marina.....and is a one of a kind. It ...
From $619 per night (USD)
VRBO
From $1455 per night (USD)
Expedia
**THE ZESTY LIME @ OLD TOWN** Beautifully Restored Home + LAST KEY SERVICES…
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Key West is k ...
From $1455 per night (USD)
Expedia
From $827 per night (USD)
VRBO
A BANANA REPUBLIC in Old Town Key West
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
A Banana Republic Gem. This Old Town house may be the nicest property in Key West. Totally redone and professionally dec ...
From $827 per night (USD)
VRBO
From $1380 per night (USD)
Expedia
**THE TOASTED COCONUT @ OLD TOWN** Fully Restored + Pool + LAST KEY SERVICES…
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Throughout Ke ...
From $1380 per night (USD)
Expedia
From $2676 per night (USD)
VRBO
Private Parking & Pool, Near Duval - Contra House
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
Summary: This captivating modern home with a striking exterior and vaulted ceilings makes for the perfect vacation home. ...
From $2676 per night (USD)
VRBO
From $473 per night (USD)
Expedia
Island Time Hideaway at Old Town Key West Historic Seaport - 3 Blocks to Duval
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
LOCATION, LOCATION, LOCATION! Located on a picturesque Old Town street, in one of the most desirable areas of the hist ...
From $473 per night (USD)
Expedia
From $1857 per night (USD)
VRBO
**GOOD VIBRATIONS @ OLD TOWN** Unique Villa & Pool + LAST KEY SERVICES…
Bedrooms:
5
Bathrooms:
4
Sleeps:
10
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Key West has ...
From $1857 per night (USD)
VRBO
From $4153 per night (USD)
Expedia
Balcony, & Pool, Near Duval - Bananas Foster
Bedrooms:
8
Bathrooms:
9
Sleeps:
19
Summary: Palm trees, sunsets, and the blissful pace of island time will all be yours when you stay at this large histori ...
From $4153 per night (USD)
Expedia
From $584 per night (USD)
VRBO
~Bahari House, Seaport~Walk to the harbor from this quintessential conch home
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local ...
From $584 per night (USD)
VRBO
From $633 per night (USD)
Expedia
Updated home with private pool, patio, & grill in enclosed tropical backyard
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Margaret Street Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $633 per night (USD)
Expedia
From $577 per night (USD)
VRBO
Charming Studio in Historic Key West, 5-Min Bike Ride to Beach & Bikes Included!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Location, location, location! Situated in the heart of the Cuban district, steps from arguably the best 'con leche' in ...
From $577 per night (USD)
VRBO
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Expedia
3 blocks from waterfront and 1 block off Duval in heart of Old Town Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Want to “ Get away from it all” but still be in the heart of Olde Town Key West with everything you need right there? Th ...
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Expedia
Click For Pricing
VRBO
3 blocks from waterfront and 1 block off Duval in Old Town Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Want to “ Get Away from it all” but still in the heart of Old Town Key West with everything you need within walking dist ...
Click For Pricing
VRBO
From $613 per night (USD)
Expedia
Historic House, Gorgeous Porch, Great Location, See 5 Star Reviews
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Treat yourself, your family and friends to a grand Key West home ideal for an extended stay on the island. This wonderfu ...
From $613 per night (USD)
Expedia
From $249 per night (USD)
VRBO
Galleon Resort efficiency
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This unit has a queen size bed. Updated ceramic stand up shower. The unit is an efficiency.It has a small refrigerator, ...
From $249 per night (USD)
VRBO
Click For Pricing
Expedia
Old Town Island House Near a grocery store, beach, bike rental shop, Restaurants
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Two Story Apartment in central Old Town Key West location. Only a 5 min bike ride to Duval. 1 King size bed on 3rd flo ...
Click For Pricing
Expedia
From $210 per night (USD)
VRBO
The Marguerite, 603 #3 Elizabeth Street, Old Town Key West monthly Rental
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
One bedroom, One Bathroom apartment in Old Key West. It is located upstairs with an outside entrance and has dormer ceil ...
From $210 per night (USD)
VRBO
From $1755 per night (USD)
Expedia
Parking, & Near Duval - Commodore's Cove
Bedrooms:
4
Bathrooms:
5
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 $1755 per night (USD)
Expedia
From $3477 per night (USD)
VRBO
Walk to Duval , Private Hot Tub - Commodore's Compound
Bedrooms:
7
Bathrooms:
10
Sleeps:
24
Summary: Welcome to Commodore's Compound, an incredible 8 bed, 7 bath home in prime location situated just one short blo ...
From $3477 per night (USD)
VRBO
From $1943 per night (USD)
Expedia
Steps from Duval, Private Hot Tub - Conch Cabin
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Summary: Located in the heart of Old Town Key West, Seaport Suite is the ideal getaway for large groups of up to 12 gues ...
From $1943 per night (USD)
Expedia
From $377 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 $377 per night (USD)
VRBO
$Luxury Galleon Resort & Marina 2 Bed\/2 Bath Marina View$
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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 ...
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Expedia
$**THE LIME & THE COCONUT @ OLD TOWN** 6BR\/6BA Compound + LAST KEY SERVICES..$
From $2629 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 $2629 per night (USD)
VRBO
From $2196 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 $2196 per night (USD)
Expedia
From $272 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 $272 per night (USD)
VRBO
From $344 per night (USD)
Expedia
Conch Republic Consul General's Cottage.-Historic District
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Stay in the Conch Republic Consul General's Cottage. Historic Carriage House is located a few blocks from famous Duval S ...
From $344 per night (USD)
Expedia

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