Fleming Key Rentals
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VRBO
Steps from Duval, Tropical Paradise at Hyatt Sunset Harbor Studio Apt
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Imbibe the relaxed Key West lifestyle from a coveted location in the heart of Old Town. Perfectly situated on the wester ...
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VRBO
Charming Bungalow with 3 Pools, Complimentary Breakfast & Cozy Turkish Robes
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the charm of Old Town in our vibrant retreat, steps away from Duval's delights. Dive into history at Hemingway' ...
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VRBO
Key West Coastal Escape: Modern Unit, Daily Housekeeping, Tiki Bar
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
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VRBO
Duval Street Retreat: Modern Unit, Daily Housekeeping, On-Site Dining
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 12
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
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VRBO
Seaside Sanctuary: Modern Design, Bicycle Rentals, 3 Pools
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 12
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
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- From $224 per night (USD)
Expedia
MIMOSAS ON PINE ~ 3 Bedroom, 2.5 Bath Home w\/ Pool & Spa in The Meadows!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
YOUR STORYBOOK COTTAGE... This island delight is tucked away on a vibrant and secluded street of The Meadows neighborhoo ...
From $224 per night (USD)Expedia
- From $400 per night (USD)
VRBO
Newly built house in old town Key West, part of a 3 unit compound.
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Relax in this new home with shared amenities. Modern design with a beautiful pool in old town key West. Walking distance ...
From $400 per night (USD)VRBO
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VRBO
Cozy old town appartment.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
We can accommodate 4 guest comfortably in this spacious apartment. Its located in old town Key West which is walking dis ...
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- From $499 per night (USD)
VRBO
3 Bedroom Key West Home with Perfect Location & Private Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The historic William Skelton Home is ideally located on Eaton Street in Old Town Key West, steps from Duval Street, hund ...
From $499 per night (USD)VRBO
- From $374 per night (USD)
VRBO
Bring your umbrella drinks! Shipyard 2bed\/2bath
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to your perfect tropical retreat in the heart of Key West, Florida! Nestled within the renowned Shipyard condomi ...
From $374 per night (USD)VRBO
- From $120 per night (USD)
VRBO
STUNNING! HEART OF OLD TOWN!: Walk to Duval and Historic Seaport in minutes.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Live like a local in this unique loft apartment in the heart of Key West's Old Town historic district. Walk to Duval Str ...
From $120 per night (USD)VRBO
- From $300 per night (USD)
VRBO
TURTLE HOUSE a dream come true!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 3
Turtle House. A Key West Artist's oasis. Now available for March 2023. Easter in Key West! Delight in the uniquene ...
From $300 per night (USD)VRBO
- From $908 per night (USD)
VRBO
Sophisticated home large enough for the entire family! Three streets from Duval!
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 12
The Blue Pineapple Estate combines a sophisticated blend of cosmopolitan tropical style with a touch of nostalgia, seaml ...
From $908 per night (USD)VRBO
- From $529 per night (USD)
VRBO
Heart of Key West - 2BR Waterfront at the Galleon Resort
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Minimum Age: 25 years old Pet Policy: No Pets An ID and credit card for a refundable security deposit will be required. ...
From $529 per night (USD)VRBO
- From $600 per night (USD)
VRBO
Recently Relisted 2BR\/2BA with Private Heated Pool - 188 steps to Duval
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Charming house in Old town near the cemetery and 3 blocks from Duval. Complete renovation with Central Air, full design ...
From $600 per night (USD)VRBO
- From $231 per night (USD)
VRBO
Limelight Cottage on Southard
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to your dream vacation rental at the Limelight Cottage in Old Town Key West! This stunning two-bedroom, one-bath ...
From $231 per night (USD)VRBO
- From $304 per night (USD)
VRBO
AMBER COTTAGE ~ Renovated 3 Bedroom, 3.5 Bathroom Home w\/ Pool!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
AN ISLAND STUNNER... This is the back cottage of the delightful Jewel Box Cottages compound, located in Old Town, just s ...
From $304 per night (USD)VRBO
- From $529 per night (USD)
Expedia
PEARL COTTAGE ~ 3 Bedroom, 3.5 Bathroom Home with Pool!
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
CONCH STYLE CHARM... This is the front cottage of the delightful Jewel Box Cottage compound, located in Old Town, just a ...
From $529 per night (USD)Expedia
- From $786 per night (USD)
VRBO
JEWEL BOX COTTAGES ~ Lush Compound with 2 Renovated Homes w\/ Private Pools!
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 16
BEDAZZLING COMPOUND... Two delightful conch style island homes are situated on one glorious parcel in Old Town, just a s ...
From $786 per night (USD)VRBO
- From $292 per night (USD)
Expedia
**SOUL OF DUVAL @ DUVAL** Modern\/Centrally Located + LAST KEY SERVICES...
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! There’s no do ...
From $292 per night (USD)Expedia
- From $500 per night (USD)
VRBO
Stunning tropical home in Old Town Key West with private pool and hot tub
- Bedrooms:
- 7
- Bathrooms:
- 7
- Sleeps:
- 8
Spacious home with open floor plan. Completely renovated in 2018. Large heated pool and hot tub in a quiet tropical oasi ...
From $500 per night (USD)VRBO
- From $385 per night (USD)
Expedia
A beautiful cottage for rent in old town Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
A beautiful historic cottage, in the complex of Sirena Blue=Blue Mermaid, located in a great area of old town Key West, ...
From $385 per night (USD)Expedia
- From $144 per night (USD)
VRBO
Old Town condo on beautiful Frances Street. Walk to Seaport
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Complete renovation in modern/industrial style. 2 bedroom. Total of only 3 condos on property. Unit has its own washe ...
From $144 per night (USD)VRBO
- From $700 per night (USD)
Expedia
Key West Paradise Returns - Gorgeous 3br 3.5ba in the Meadows, Old Town Key West
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
This gorgeous 3br/3.5ba home is very private with a pool and spa, outdoor grill, three ensuite baths, chef's kitchen wit ...
From $700 per night (USD)Expedia
- From $699 per night (USD)
VRBO
Historic Mansion in Old Town Key West with Private Pool - Sleeps 16!
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 16
The historic William Skelton Home is ideally located on Eaton Street in Old Town Key West, steps from Duval Street, hund ...
From $699 per night (USD)VRBO
- From $867 per night (USD)
VRBO
The Cathouse, an Old Town tropical poolside oasis with ample room for everyone!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Relax in this tropical poolside townhouse in the heart of Key West. Wake up surrounded by lush tropical landscaping and ...
From $867 per night (USD)VRBO
- From $980 per night (USD)
VRBO
Pure Bliss
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This wonderful restoration is located in the heart of Old Town Key West. A 3 bd/3BA home just 3 blocks from Duval. Meti ...
From $980 per night (USD)VRBO
- From $164 per night (USD)
Expedia
DREAM ON ~ Perfectly Located and Renovated 3 BR, 2 Ba Home w\/ Outdoor Shower!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
FREE YOUR ISLAND SOUL… This ultimate classic Key West beauty is the poetic essence of authentic island living. Nestled i ...
From $164 per night (USD)Expedia
- From $265 per night (USD)
VRBO
Soleil Chalet - 3 bedroom - private pool- Luxury living in Old Town Key West
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Your own private paradise awaits in this peaceful district just steps away from the buzz of Duval Street. “Soleil Chalet ...
From $265 per night (USD)VRBO
- From $350 per night (USD)
VRBO
Paradise found! 2 br\/1 bth restored Old Town home with private cocktail pool
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Fully renovated and furnished 2 bedroom,1 bath cottage in a lovely tropical setting across from the cemetery in Old Town ...
From $350 per night (USD)VRBO
- From $795 per night (USD)
VRBO
SEAPORT SUMMIT at Galleon Resort near Mallory Square—King Suite-Beach-Pool-BBQ
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
GALLEON RESORT LUXURY WATERFRONT PENTHOUSE with LOFT + GREAT VIEWS OF THE MARINA, OCEAN & HISTORIC SEAPORT 5th FLOOR M ...
From $795 per night (USD)VRBO
- From $282 per night (USD)
Expedia
Cottage in Old Town Key West w\/ Pool, Parking and Privacy. One block from Duval!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Down a hidden lane in the heart of Old Town Key West you will find Loco Court Cottages. The compound is located one blo ...
From $282 per night (USD)Expedia
- From $553 per night (USD)
VRBO
Spacious Updated Waterfront Condo, 2\/2 Pool, Dock
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Time to relax! Bring your family & friends to this 1350 sqft Waterfront condo home. Boat slips available on sit ...
From $553 per night (USD)VRBO
- From $327 per night (USD)
VRBO
Casa Bella Petite le Bleu
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
First impressions are everything. And it's love at first sight with the charming 2BR 2BA Casa Bella Petite le Bleu. This ...
From $327 per night (USD)VRBO
- From $1344 per night (USD)
VRBO
Waterfront Penthouse sleeps 16 w\/Pool & Boat Dock
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Summary: Gorgeous completely renovated 2400sqft waterfront Penthouse condo in downtown Key West. Boat slips available on ...
From $1344 per night (USD)VRBO
- From $250 per night (USD)
VRBO
Key West Dollhouse with private parking
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Great 2 bedroom, 2 1/2 bath private home ready to start your Key West adventure. Also has a private hot tub and off str ...
From $250 per night (USD)VRBO
- From $650 per night (USD)
VRBO
Waterfront Retreat, Old Town, Hyatt, 4 Nights, Sleeps 6, Swimming Pool, Hot Tub
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Imbibe in the relaxed Key West lifestyle from a coveted location nestled in the heart of Key West’s famed Old Town at th ...
From $650 per night (USD)VRBO
- From $915 per night (USD)
VRBO
Designer Octagon House of Key West
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Standing prominently in the sought-after Key West Historic Seaport Neighborhood, this iconic Designer Octagon House of K ...
From $915 per night (USD)VRBO
- From $106 per night (USD)
VRBO
NEWTON'S NEST ~ Adult Only, 1 Bedroom, 1 Bath Condo w\/ Shared Pool!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
SIMPLISTIC ELEGANCE... Enjoy easy tropical living in this quiet refuge located within Old Town where you can roost and i ...
From $106 per night (USD)VRBO
- From $601 per night (USD)
VRBO
Down Island Digs ~ Downtown with Private Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Everything about this historic Key West tropical gem adds up to make a precious private garden cottage. Sitting in the m ...
From $601 per night (USD)VRBO
- From $2000 per night (USD)
VRBO
Exclusive, 5 bedroom, private mansion with heated pool, just off Duval St.
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 14
If you are looking to spend relaxing, yet entertaining, quality time with family and friends, then you have found the pe ...
From $2000 per night (USD)VRBO
- From $133 per night (USD)
Expedia
Cottage in Old Town Key West w\/ Pool, Parking and Privacy. One block from Duval!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Down a hidden lane in the heart of Old Town Key West you will find Loco Court Cottages.The compound is located one block ...
From $133 per night (USD)Expedia
- From $1092 per night (USD)
VRBO
Pavilion Villa ~ A Private Paradise
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
A Private Tropical Paradise ... is the feeling you get when you enter the pavilion of this award winning villa just a ha ...
From $1092 per night (USD)VRBO
- From $953 per night (USD)
VRBO
Key West Wabi Sabi ~ Authentic Key West Cottage
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Undeniably adorable, Key West Wabi Sabi vacation rental is a celebration of authentic Key West cottage style island livi ...
From $953 per night (USD)VRBO
- From $149 per night (USD)
VRBO
Oceanfront condo in the heart of Key West. Boat slip available!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy gorgeous waterfront views in one of the most quiet and serene area of Key West while being 5 min away from the ic ...
From $149 per night (USD)VRBO
- From $200 per night (USD)
VRBO
Historic Apartment On The Waterfront
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Newly renovated historic apartment in the heart of Key West. 10 foot ceilings and huge windows allow bright, natural lig ...
From $200 per night (USD)VRBO
- From $1829 per night (USD)
VRBO
Island Rendezvous - A Family Gathering
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
Island Rendezvous vacation rental offers the perfect solution for a gathering of family or friends who desire to be in t ...
From $1829 per night (USD)VRBO
- From $400 per night (USD)
VRBO
Paradise on White Street
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
After spending your day out on the water or strolling down Duval St., come relax at this Charming 2-Story Historic Home. ...
From $400 per night (USD)VRBO
- From $877 per night (USD)
VRBO
Heavenly Hideout at Rainbow's End
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to the end (and the beginning) of the road. There aren’t many places in the world where you can say you’re both ...
From $877 per night (USD)VRBO
- From $700 per night (USD)
VRBO
Old Town Key West Compound with Pool, Parking and Privacy One Block Off Duval!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Down a hidden lane in the heart of Old Town Key West you will find Loco Court. The compound is located one block off Duv ...
From $700 per night (USD)VRBO
- From $379 per night (USD)
VRBO
Old Town Key West Condo - MONTHLY RENTALS ONLY
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Our condo is located is in the heart of Key West's Old Town. This neighborhood is filled with historic homes dating fro ...
From $379 per night (USD)VRBO
- From $299 per night (USD)
VRBO
Cottage in Paradise, Old Town. Walk to Duval & beaches. Hot tub, Pet Friendly.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Our home is in Old Town Key West, within walking distance of Duval Street, White Street art galleries, restaurants, bars ...
From $299 per night (USD)VRBO
- From $1071 per night (USD)
VRBO
Tropical ~ Tranquility
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Few places exist where you can ride the fine line separating a secluded tranquil luxury villa, and the Heart of Old Town ...
From $1071 per night (USD)VRBO
- From $300 per night (USD)
VRBO
\"Island Time\" in Old Town
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to "Island Time" located in the heart of Old Town! This 2nd floor condo is perfect home base for your adventure ...
From $300 per night (USD)VRBO
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VRBO
BEAUTIFUL NEW MONTHLY RENTAL - Old Town Key West - top of the line furnishings
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Old Town Villas is a Caribbean inspired community of only 20 units in the heart of Key West This luxurious townhome is l ...
Click For PricingVRBO
- From $474 per night (USD)
VRBO
Knot A Worry Monthly Vacation Home
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Knot A Worry is a monthly vacation home in the heart of Old Town Key West! Just one block from famous Duval Street wher ...
From $474 per night (USD)VRBO
- From $241 per night (USD)
VRBO
Conch Easy Livin` Monthly Vacation Home
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Discover Conch Easy LIvin' at this monthly vacation home in the heart of Old Town Key West! You'll get a real feel of th ...
From $241 per night (USD)VRBO
- From $335 per night (USD)
VRBO
Key West Cottage Located in Old Town Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Key West Cottage. Located in the Historic Seaport Area of Old Town. 2 BR. 2 BR. Three HD TV's. Streaming on every TV. W ...
From $335 per night (USD)VRBO
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VRBO
2BR Condo - Galleon Resort & Marina - Walk to Mallory Square and Duval Street
- 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 ...
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- Click For Pricing
VRBO
Townhouse Suite with 1 Bed, 1 Bath, Kitchen, and Pullout Sofa
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This two story town house features a first floor living room with queen sofa bed, full kitchen and double French doors o ...
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