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 $467 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 $467 per night (USD)
VRBO
Click For Pricing
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 $650 per night (USD)
VRBO
Heart of Key West - 2BR Waterfront at the Galleon Resort
Bedrooms:
2
Bathrooms:
2
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 $650 per night (USD)
VRBO
From $467 per night (USD)
Expedia
Welcome to the Shady Palms - Private Pool - RealKeyWest
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Step into this beautifully restored and redecorated 1933 Key West home. This first-floor home has Bahama shutters throug ...
From $467 per night (USD)
Expedia
From $310 per night (USD)
VRBO
TROPICAL PROPERTIES VACATION RENTAL - KEY WEST
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
****This property requires a minimum stay of 28 nights in the same calendar month**** ***Brand New Pool with waterfall, ...
From $310 per night (USD)
VRBO
From $271 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 $271 per night (USD)
Expedia
From $784 per night (USD)
VRBO
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 $784 per night (USD)
VRBO
From $341 per night (USD)
Expedia
**SEAPORT SENSATION @ OLD TOWN VILLAS** Condo & Pool + 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! It is not so ...
From $341 per night (USD)
Expedia
From $628 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 $628 per night (USD)
VRBO
From $356 per night (USD)
Expedia
Runaway Bills | 3 Bed, 1 Bath
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
This stylish Conch Home is tucked away on a quiet lane in Old Town Key West. Surrounded by distinctive neighborhoods thi ...
From $356 per night (USD)
Expedia
From $379 per night (USD)
VRBO
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 $379 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 $931 per night (USD)
VRBO
Waterfront 4 Bed, 4-Bath Condo @ 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 $931 per night (USD)
VRBO
From $793 per night (USD)
Expedia
Waterfront 4-Bedroom 3-Bath 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 $793 per night (USD)
Expedia
From $707 per night (USD)
VRBO
3-Bedroom 3-Bath 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 $707 per night (USD)
VRBO
From $820 per night (USD)
Expedia
Waterfront 4-Bed, 4-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 $820 per night (USD)
Expedia
From $799 per night (USD)
VRBO
4-Bed 4.5 Bath Condo @ Bayfront Suites & Marina Non-Waterfront
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $799 per night (USD)
VRBO
From $714 per night (USD)
Expedia
3 Bedroom Condo at Bayfront Suites & Marina - Non-Waterfront
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $714 per night (USD)
Expedia
From $812 per night (USD)
VRBO
4-Bed, 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 $812 per night (USD)
VRBO
From $803 per night (USD)
Expedia
4-Bed, 4.5 Bath Condo at Bayfront Suites & Marina Non-Waterfront
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $803 per night (USD)
Expedia
From $689 per night (USD)
VRBO
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 $689 per night (USD)
VRBO
From $148 per night (USD)
Expedia
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 $148 per night (USD)
Expedia
From $311 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 $311 per night (USD)
VRBO
From $392 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 $392 per night (USD)
Expedia
From $215 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 $215 per night (USD)
VRBO
From $286 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 $286 per night (USD)
Expedia
From $333 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 $333 per night (USD)
VRBO
From $216 per night (USD)
Expedia
Old Town! Spacious Condo in Historic Home w/Pool!
Bedrooms:
2
Bathrooms:
1
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 $216 per night (USD)
Expedia
From $313 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 $313 per night (USD)
VRBO
From $660 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 $660 per night (USD)
Expedia
From $691 per night (USD)
VRBO
**THE CONTENTED CRANE @ OLD TOWN** Home & Pool Near Duval + LAST KEY SERVICES...
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Traveling to ...
From $691 per night (USD)
VRBO
From $1651 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 $1651 per night (USD)
Expedia
From $844 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 $844 per night (USD)
VRBO
From $340 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 $340 per night (USD)
Expedia
From $948 per night (USD)
VRBO
**AMERICANA TROPICALE @ OLD TOWN** Home & Pool by Duval + LAST KEY SERVICES...
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! For the ultim ...
From $948 per night (USD)
VRBO
From $1993 per night (USD)
Expedia
**THE IBIS & THE CRANE @ OLD TOWN** Compound Near Duval + LAST KEY SERVICES...
Bedrooms:
7
Bathrooms:
6
Sleeps:
16
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Dreaming of a ...
From $1993 per night (USD)
Expedia
From $846 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 $846 per night (USD)
VRBO
From $605 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 $605 per night (USD)
Expedia
From $1314 per night (USD)
VRBO
**CASA VICTORIA @ OLD TOWN** Historic 5BR 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! CASA VICTORIA ...
From $1314 per night (USD)
VRBO
From $461 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 $461 per night (USD)
Expedia
From $724 per night (USD)
VRBO
**THE SMILING IBIS @ OLD TOWN** Home & Pool Near Duval + LAST KEY SERVICES...
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Traveling to ...
From $724 per night (USD)
VRBO
From $770 per night (USD)
Expedia
ROOFTOP PENTHOUSE- | 2 Bed, 1.5 Bath
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
The high-end sophisticated Rooftop Penthouse is located directly above the famous Wyland Gallery on Duval Street. Enjoy ...
From $770 per night (USD)
Expedia
From $334 per night (USD)
VRBO
Bright Condo with Homey Feel, Entertainment & Private Parking - Beach Nearby
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Jasmine Suite Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $334 per night (USD)
VRBO
From $175 per night (USD)
Expedia
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 $175 per night (USD)
Expedia
Click For Pricing
VRBO
Dog-friendly home w/ large private pool only a short walk to Historic Seaport
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Seaport Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
Click For Pricing
VRBO
From $542 per night (USD)
Expedia
Little Paradise, Historic Harbor Old Town Key West 2/1.5
Bedrooms:
1
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 $542 per night (USD)
Expedia
Click For Pricing
VRBO
7 Nights - Hyatt Sunset Harbor 2 bed/2bath/Kitchen/Sleeps 6. Fantastic Location
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Fantastic location!!! Sunday to Sunday 7 night rental at HYATT SUNSET HARBOR 2 bedrooms 2 bath full kitchen and common a ...
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VRBO
$Sunny Condo w\/ Entertainment, Balcony, & Great Location Near Beach - Dogs OK$
Click For Pricing
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 ...
Click For Pricing
Expedia
From $476 per night (USD)
VRBO
Charming Condo w/ Entertainment & Private Parking - Great In-Town Location
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Gardenia Getaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $476 per night (USD)
VRBO
From $335 per night (USD)
Expedia
Elegant Condo with Entertainment & Private Parking - Great Central Location
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Orchid Suite Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $335 per night (USD)
Expedia
From $170 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 $170 per night (USD)
VRBO
Click For Pricing
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 ...
Click For Pricing
Expedia
Click For Pricing
VRBO
Dante's Marina Townhouse 2 bed 1.5 bath unit with a 5 minute walk to Duval!
Bedrooms:
1
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
From $194 per night (USD)
Expedia
Modern 2BR Condo Old Town/Balcony & Pool
Bedrooms:
1
Bathrooms:
2
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 $776 per night (USD)
VRBO
Balcony on Duval - Duval Dream Loft
Bedrooms:
1
Bathrooms:
2
Sleeps:
8
Summary: Located right in the heart of the World Famous Duval Street, enjoy a true downtown Key West experience! This un ...
From $776 per night (USD)
VRBO
From $770 per night (USD)
Expedia
Balcony on Duval - The Collins on Duval
Bedrooms:
1
Bathrooms:
2
Sleeps:
8
Summary: Located right in the heart of the World Famous Duval Street, enjoy a true downtown Key West experience! The Col ...
From $770 per night (USD)
Expedia
From $1629 per night (USD)
VRBO
Balcony on Duval - Duval's Duet on Duval
Bedrooms:
2
Bathrooms:
4
Sleeps:
16
Summary: Located right in the heart of the World Famous Duval Street, enjoy a true downtown Key West experience! Duval's ...
From $1629 per night (USD)
VRBO
From $301 per night (USD)
Expedia
Old Town home a short walk to Duval/Couples Oasis
Bedrooms:
1
Bathrooms:
1
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
From $253 per night (USD)
VRBO
Relaxing island home/Great location/Stylish
Bedrooms:
1
Bathrooms:
1
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 $253 per night (USD)
VRBO
From $146 per night (USD)
Expedia
NEW MONTHLY RENTAL, Old Town Duplex, SUMMER DEALS, private backyard, pets welcom
Bedrooms:
2
Bathrooms:
2
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 $146 per night (USD)
Expedia
Click For Pricing
VRBO
Conch Cottage | 'Old Town' Home w/ Shared Pool
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Escape to this charming Key West cottage, the perfect home base for your island getaway. Whether you relax by t ...
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VRBO
From $692 per night (USD)
Expedia
Enjoy Old Town Key West in this Beautifully furnished house
Bedrooms:
2
Bathrooms:
2
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)
Expedia
From $535 per night (USD)
VRBO
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 $535 per night (USD)
VRBO
From $398 per night (USD)
Expedia
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 $398 per night (USD)
Expedia
From $407 per night (USD)
VRBO
Green 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 $407 per night (USD)
VRBO
From $386 per night (USD)
Expedia
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 $386 per night (USD)
Expedia
From $334 per night (USD)
VRBO
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 $334 per night (USD)
VRBO
From $460 per night (USD)
Expedia
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 $460 per night (USD)
Expedia
From $147 per night (USD)
VRBO
MONTHLY RENTAL, Old Town Duplex, private backyd, SUMMER DEALS, 2 BR/2 BA,pets ok
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
ou must cancel.Welcome to Sea Monkey and The Mermaid! Our home is a duplex located in Old Town and full of Key West ch ...
From $147 per night (USD)
VRBO
From $539 per night (USD)
Expedia
Galleon Resort beach hotel luxury in Old Town Key West
Bedrooms:
1
Bathrooms:
1
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 $539 per night (USD)
Expedia
From $737 per night (USD)
VRBO
**THE ZESTY LIME @ OLD TOWN** Beautifully Restored Home + LAST KEY SERVICES…
Bedrooms:
3
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 $737 per night (USD)
VRBO
From $1788 per night (USD)
Expedia
Private Parking & Pool, Near Duval - Contra House
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
Summary: This captivating modern home with a striking exterior and vaulted ceilings makes for the perfect vacation home. ...
From $1788 per night (USD)
Expedia
From $470 per night (USD)
VRBO
Island Time Hideaway at Old Town Key West Historic Seaport - 3 Blocks to Duval
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
LOCATION, LOCATION, LOCATION! Located on a picturesque Old Town street, in one of the most desirable areas of the hist ...
From $470 per night (USD)
VRBO
From $888 per night (USD)
Expedia
**GOOD VIBRATIONS @ OLD TOWN** Unique Villa & Pool + LAST KEY SERVICES…
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Key West has ...
From $888 per night (USD)
Expedia
From $2433 per night (USD)
VRBO
Banana's Foster Guesthouse | 1 Block to Duval St
Bedrooms:
7
Bathrooms:
7
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 $2433 per night (USD)
VRBO
From $359 per night (USD)
Expedia
~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 $359 per night (USD)
Expedia
From $729 per night (USD)
VRBO
**THE TOASTED COCONUT @ OLD TOWN** Fully Restored + Pool + LAST KEY SERVICES…
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Throughout Ke ...
From $729 per night (USD)
VRBO
From $292 per night (USD)
Expedia
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 $292 per night (USD)
Expedia
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VRBO
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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VRBO
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Expedia
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 ...
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Expedia
From $279 per night (USD)
VRBO
Historic House, Gorgeous Porch, Great Location, See 5 Star Reviews
Bedrooms:
3
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 $279 per night (USD)
VRBO
From $307 per night (USD)
Expedia
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 $307 per night (USD)
Expedia
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VRBO
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 ...
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VRBO
From $299 per night (USD)
Expedia
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 $299 per night (USD)
Expedia
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VRBO
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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VRBO
From $2396 per night (USD)
Expedia
**THE LIME & THE COCONUT @ OLD TOWN** 6BR/6BA Compound + LAST KEY SERVICES..
Bedrooms:
7
Bathrooms:
6
Sleeps:
16
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! According to ...
From $2396 per night (USD)
Expedia
From $1024 per night (USD)
VRBO
Commodore's Cove - Epic Location 1 Block to Duval
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 $1024 per night (USD)
VRBO
From $1861 per night (USD)
Expedia
Commodore's Compound - Epic Location Near Duval
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 $1861 per night (USD)
Expedia
From $1077 per night (USD)
VRBO
Steps from Duval, Private Hot Tub - Seaport Suite
Bedrooms:
3
Bathrooms:
4
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 $1077 per night (USD)
VRBO
From $1306 per night (USD)
Expedia
**GRAND KEY OASIS @ THE ANNEX** Magnificent Estate & Pool + LAST KEY SERVICES…
Bedrooms:
5
Bathrooms:
5
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! The vacation ...
From $1306 per night (USD)
Expedia
From $332 per night (USD)
VRBO
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 $332 per night (USD)
VRBO
From $284 per night (USD)
Expedia
Conch Republic Consul General's Cottage.-Pool-Historic District-Assigned Parking
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 $284 per night (USD)
Expedia
From $501 per night (USD)
VRBO
ABSOLUTE TRUMAN ANNEX in Key West
Bedrooms:
2
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 $501 per night (USD)
VRBO
From $565 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 $565 per night (USD)
Expedia
From $649 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 $649 per night (USD)
VRBO
From $591 per night (USD)
Expedia
Washer & Dryer, Near Downtown - Mesa House, Dos
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 $591 per night (USD)
Expedia
From $761 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 $761 per night (USD)
VRBO
From $575 per night (USD)
Expedia
Nassau suite-2 bedroom 2 bath, a block off Duval St w/pool, parking
Bedrooms:
2
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 $575 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 $2068 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 $2068 per night (USD)
Expedia

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Results: 758 Rentals