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 $799 per night (USD)
VRBO
Charming 4-bedroom house with pool - 10 MIN. WALK TO DUVAL STREET
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
Welcome to 1015 Eaton Street, nestled in the heart of the Historic Seaport neighborhood. Renovated in 2024, this 4-bedro ...
From $799 per night (USD)
VRBO
$First Mate's Escape | Historic Apartment Near Duval w\/ Pool!$
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Expedia
First Mate's Escape | Historic Apartment Near Duval w\/ Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Step back in time and embrace the enchanting history of Key West with a stay at First Mate's Escape, a stunning loft apa ...
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Expedia
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VRBO
Peaceful & Relaxing Key West Bungalow, Near Famous Duval Street, Shops
Bedrooms:
1
Bathrooms:
1
Sleeps:
1
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
From $265 per night (USD)
Expedia
The Secret Garden - Quaint 2 Bedroom / 2 Bath Cottage with Shared Pool & Hot Tub
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
THE SECRET GARDEN – Charming 2 Bedroom / 2 Bathroom Cottage located in the Center of Old Town - 4 Guests - 2 Spaciou ...
From $265 per night (USD)
Expedia
$NEW! - The Jolly Rooster Cottage\nSteps to Duval - Prime and Quiet Location$
From $569 per night (USD)
VRBO
NEW! - The Jolly Rooster Cottage\nSteps to Duval - Prime and Quiet Location
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Coming July 1! UNDER RENOVATION - From the owners of the Dancing Rooster, this newly renovated 2BR/2BA home sleeps 6 and ...
From $569 per night (USD)
VRBO
From $358 per night (USD)
Expedia
**SUNFLOWER MELODIES @ MIDTOWN** Modern Private Home & Pool + LAST KEY SERVICES…
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! SUNFLOWER MEL ...
From $358 per night (USD)
Expedia
From $747 per night (USD)
VRBO
Paradise Awaits @ SOLEIL CHALET
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Your own private paradise awaits in this peaceful neighborhood just steps away from the buzz of Duval Street. “Soleil Ch ...
From $747 per night (USD)
VRBO
From $208 per night (USD)
VRBO
KEY LIME COTTAGE - an adorable Monthly rental
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
Located on the edge of Old Town near the art district on White Street, Key Lime Cottage offers great accommodations for ...
From $208 per night (USD)
VRBO
From $272 per night (USD)
VRBO
CONCH EASY LIVING -1 block to Duval-Monthly rental
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 $272 per night (USD)
VRBO
From $327 per night (USD)
VRBO
KNOT A WORRY so close to Duval at this monthly rental
Bedrooms:
2
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, you' ...
From $327 per night (USD)
VRBO
From $1168 per night (USD)
VRBO
Casa Loca - so close to Duval 3bd/2ba private home
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Casa Loca is perfect for guests who want to enjoy the finest that Key West has to offer! The perfect location, less than ...
From $1168 per night (USD)
VRBO
From $363 per night (USD)
Expedia
OSPREY STUDIO @ The Colony-Sleeps up to 4
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to Osprey—a beautiful studio in the heart of Old Town Key West! Perfectly located at the Colony on Olivia Street ...
From $363 per night (USD)
Expedia
From $1008 per night (USD)
VRBO
3 Bedroom Key West Home - 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 $1008 per night (USD)
VRBO
From $699 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 $699 per night (USD)
VRBO
From $389 per night (USD)
VRBO
MIMOSAS ON PINE ~ 3 Bedroom 2.5 Bath Home w/Pool & Great Spring/Summer Deals!
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
YOUR STORYBOOK COTTAGE... This island delight is tucked away on a vibrant and secluded street of The Meadows neighborhoo ...
From $389 per night (USD)
VRBO
From $156 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 $156 per night (USD)
VRBO
From $749 per night (USD)
VRBO
Sophisticated 5 Bedroom Home With Cocktail Pool. 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 $749 per night (USD)
VRBO
From $1664 per night (USD)
VRBO
Galleon Resort, Pool, Hot Tub, In Town, Pool, Marina
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The Galleon Resort offers a multitude of accommodations in studio, one-bedroom and two-bedroom configurations. Studios h ...
From $1664 per night (USD)
VRBO
From $1698 per night (USD)
VRBO
Banyon Resort, Beach, Pool, Hot Tub, In Town
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
In the heart of historic Old Town Key West, The Banyan Resort boasts a storied history and sits on a historic, mid-1800' ...
From $1698 per night (USD)
VRBO
From $775 per night (USD)
VRBO
Everything Key West has to offer @ Mango Cottage
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This historic Conch house is an excellent vacation home which has been thoughtfully remodeled to provide the best in mod ...
From $775 per night (USD)
VRBO
From $275 per night (USD)
VRBO
A Bit of Heaven is the perfect monthly rental in Key West
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This quintessential Key West eyebrow home is located in Old Town's prime Historic District, sitting just blocks away fro ...
From $275 per night (USD)
VRBO
From $356 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 $356 per night (USD)
VRBO
From $405 per night (USD)
VRBO
Bring your umbrella drinks @Tiki Beach Too! 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 $405 per night (USD)
VRBO
From $167 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 $167 per night (USD)
VRBO
From $237 per night (USD)
VRBO
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 $237 per night (USD)
VRBO
From $454 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 $454 per night (USD)
VRBO
From $376 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 $376 per night (USD)
VRBO
From $381 per night (USD)
Expedia
PEARL COTTAGE ~ 3 Bedroom, 3.5 Bathroom Home with Pool!
Bedrooms:
3
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 $381 per night (USD)
Expedia
From $511 per night (USD)
VRBO
JEWEL BOX COTTAGES ~ Lush Compound with 2 Renovated Homes w/ Private Pools!
Bedrooms:
6
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 $511 per night (USD)
VRBO
From $1288 per night (USD)
VRBO
The Cathouse, an Old Town tropical poolside oasis with huge, heated pool
Bedrooms:
2
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 $1288 per night (USD)
VRBO
From $552 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 $552 per night (USD)
VRBO
From $1855 per night (USD)
Expedia
Historic Mansion in Old Town Key West with Private Pool - Sleeps 16!
Bedrooms:
4
Bathrooms:
6
Sleeps:
16
The iconic William Skelton Home in downtown Key West offers an ideal retreat for your group of 16 guests. The six bedroo ...
From $1855 per night (USD)
Expedia
From $710 per night (USD)
VRBO
Florida | Waterfront 2BR/2BA w/ Pool + Dock Access
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Bring friends and family to this updated 1,350 sqft waterfront corner condo in historic downtown Key West! Just ...
From $710 per night (USD)
VRBO
From $321 per night (USD)
VRBO
Casa Bella Petite le Bleu - Luxury Key West Cottage w Pool - 2 Blocks Off Duval
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 $321 per night (USD)
VRBO
From $955 per night (USD)
VRBO
Bella Grand Premier Estate Key West - 2 Blocks off Duval w Private Pool
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Inspired by romantic turn-of-the-century architecture, Bella Grand Premier Estate is a unique Old Town Key West estate w ...
From $955 per night (USD)
VRBO
From $1677 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 $1677 per night (USD)
VRBO
From $886 per night (USD)
VRBO
Private Heated Pool-2BR/2BA-OldTown Location-Avail Jan 1 -March 31 -Weekly Maid
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 $886 per night (USD)
VRBO
From $368 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 $368 per night (USD)
VRBO
From $891 per night (USD)
VRBO
Designer Octagon House of Key West - w Private Pool - Blocks off Duval
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 $891 per night (USD)
VRBO
From $442 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 $442 per night (USD)
Expedia
From $237 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 $237 per night (USD)
VRBO
From $235 per night (USD)
VRBO
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 $235 per night (USD)
VRBO
From $1822 per night (USD)
VRBO
Key West Island Rendezvous - Private Compound Steps Off Duval w/Pool - Sleeps 12
Bedrooms:
5
Bathrooms:
6
Sleeps:
14
Island Rendezvous vacation rental offers the perfect solution for a gathering of family or friends who desire to be in t ...
From $1822 per night (USD)
VRBO
From $474 per night (USD)
VRBO
Paradise on White Street
Bedrooms:
3
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 $474 per night (USD)
VRBO
From $668 per night (USD)
VRBO
Down Island Digs - 2BR Cottage 1 Block off Duval Street Key West w/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 $668 per night (USD)
VRBO
$\Island Time\ in Old Town$
From $363 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 $363 per night (USD)
VRBO
From $145 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 $145 per night (USD)
VRBO
From $235 per night (USD)
VRBO
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 $235 per night (USD)
VRBO
From $1135 per night (USD)
VRBO
Pavilion Villa – A Key West Private Paradise 1 Block Off Duval w Pool
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 $1135 per night (USD)
VRBO
From $958 per night (USD)
Expedia
Key West Wabi Sabi - Authentic Downtown Cottage w Pool - Steps Off Duval
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Undeniably adorable, Key West Wabi Sabi vacation rental is a celebration of authentic Key West cottage style island livi ...
From $958 per night (USD)
Expedia
From $484 per night (USD)
VRBO
Key West Cottage Located in Old Town Key West. Available March 2025!!!!!
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 $484 per night (USD)
VRBO
From $1325 per night (USD)
Expedia
Tropical Tranquility - 4BR Luxury Villa In Old Town Key West w Pool
Bedrooms:
3
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 $1325 per night (USD)
Expedia
From $959 per night (USD)
VRBO
Heavenly Hideout at Rainbows End Key West - Steps from Duval w Private Pool
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 $959 per night (USD)
VRBO
From $811 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 $811 per night (USD)
VRBO
From $609 per night (USD)
VRBO
Town Home with King Bed, Full Kitchen, and Pullout Sofa
Bedrooms:
0
Bathrooms:
0
Sleeps:
4
This is a two-story Victorian Town Home with 1st and 2nd floor private verandas overlooking historic Fleming Street. It ...
From $609 per night (USD)
VRBO
From $549 per night (USD)
VRBO
Tropical Suite sleeps 4
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This newly renovated 2nd story unit features a living room with soaring lofted ceilings, a modern kitchenette and a top ...
From $549 per night (USD)
VRBO
From $188 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 $188 per night (USD)
VRBO
From $609 per night (USD)
VRBO
Poolside Suite with 1 Bedroom, 1 Bath with Kitchen and Pullout Sofa
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
A beautifully renovated suite featuring a living room with a queen sofa bed, a modern kitchenette and a spacious master ...
From $609 per night (USD)
VRBO

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Fleming Key Rentals

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Results: 758 Rentals