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 $439 per night (USD)
VRBO
Key West Comfort | Bungalow with Patio, 3 Pools! Free Breakfast
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $439 per night (USD)
VRBO
From $465 per night (USD)
VRBO
Central Key West Stay | 3 Pools, Free Daily Breakfast, Pet-Friendly
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $465 per night (USD)
VRBO
From $458 per night (USD)
VRBO
Tropical Bungalow, 3 Pools, Breakfast Included, Pets Allowed, Near Shops & Bars
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $458 per night (USD)
VRBO
From $483 per night (USD)
VRBO
Peaceful & Relaxing Key West Bungalow, Near Famous Duval Street, Free Breakfast!
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' ...
From $483 per night (USD)
VRBO
From $446 per night (USD)
VRBO
Pet-Friendly & Cozy Bungalow, Daily Breakfast & Poolside Lounging!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $446 per night (USD)
VRBO
From $433 per night (USD)
VRBO
Bungalow in Heart of Key West | 3 Pool, Free Breakfast, Shops & Bars Nearby
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $433 per night (USD)
VRBO
From $479 per night (USD)
VRBO
Key West Charm | 3 Pools, Complimentary Breakfast, Near Duval Street!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $479 per night (USD)
VRBO
From $528 per night (USD)
VRBO
Key West Getaway | Romantic Bungalow, Pools, Free Breakfast & Pets Allowed
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $528 per night (USD)
VRBO
From $1649 per night (USD)
VRBO
The Penthouse at Custom House Inn | New! Coastal Escape on Duval Street!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
The Penthouse at Custom House Inn | Serene Coastal Escape on Duval Street! Immerse yourself in the calm and comfort of ...
From $1649 per night (USD)
VRBO
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Expedia
Most Beautiful View on Key West?
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Make yourself at home in this 2-bedroom Key West retreat. This cool condo features a beautiful view from every room. Spa ...
Click For Pricing
Expedia
From $599 per night (USD)
VRBO
Upscale 2-bdrm Lock-off villa in the heart of Old Town. Close to Mallory Square
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to this upscale condo in Key West. This terrific property features a one-bedroom villa with plush queen bed, ful ...
From $599 per night (USD)
VRBO
From $454 per night (USD)
Expedia
Charming island cottage with sunny patio, modern kitchen, AC & dog friendly yard
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Casa Sirena Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $454 per night (USD)
Expedia
From $359 per night (USD)
VRBO
COCKTAILS ON THE CORNER- 2 Bedroom / 1 Bathroom W/ Pool - Old Town Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Welcome to Cocktails on the Corner — Your Tropical Oasis in Old Town Key West! Step into the perfect blend of historic ...
From $359 per night (USD)
VRBO
From $835 per night (USD)
Expedia
Sandbar Suite | 2 bed/2 bath apartment with patio overlooking Front Street
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The Sandbar Suite – 2BR/2BA Island Getaway with Front Street views Welcome to The Sandbar Suite, a bright and breezy 2 ...
From $835 per night (USD)
Expedia
From $611 per night (USD)
VRBO
The Conchtail Club a Tropical Oasis in the Heart of Old Town – Shipyard Complex
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The Conchtail Club a Tropical Oasis in the Heart of Old Town – Shipyard Condo in Truman Annex Welcome to your sunny esc ...
From $611 per night (USD)
VRBO
From $330 per night (USD)
Expedia
Key Lime Hideaway- Traditional Key West Style House in Downtown
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Your Old Key West Oasis! Experience the charm of Old Key West in this stunning traditional Conch-style home. ...
From $330 per night (USD)
Expedia
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VRBO
Charming studio in Key West -Close to Duval. Beautiful Pool area.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Tropical Key West welcomes you to a classic Florida studio condominium, offering a plush king-size bed, casual living ar ...
Click For Pricing
VRBO
From $1451 per night (USD)
VRBO
Perfect for Families! 2BR Suite with Balconies, Onsite Pool, Private Beach!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $1451 per night (USD)
VRBO
From $1451 per night (USD)
VRBO
Sea Breeze 2 Bedroom Oceanfront Suite at The Pier House Resort & Spa
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $1451 per night (USD)
VRBO
From $1527 per night (USD)
VRBO
Pet-friendly Accommodation with Balcony, Outdoor Pool, Private White Sand Beach!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $1527 per night (USD)
VRBO
From $1527 per night (USD)
VRBO
Havana Heights Two Bedroom Suite at The Pier House Resort & Spa
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $1527 per night (USD)
VRBO
From $679 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 $679 per night (USD)
Expedia
From $154 per night (USD)
VRBO
The Ivy Cottage - Private Home in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Tucked away on a quiet street in the heart of Old Town Key West you will find the quaint and comfortable Ivy Cottage. Th ...
From $154 per night (USD)
VRBO
From $1350 per night (USD)
Expedia
Premier resort overlooking the Gulf. Walk to Mallory Square, restaurants, beach.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Imbibe the relaxed Key West lifestyle from a coveted location in the heart of Old Town. Perfectly situated on the wester ...
From $1350 per night (USD)
Expedia
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VRBO
KEY WEST- Amazing 3 rd floor corner unit overlooking Florida Bay and Yacht Club.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Consider this 3rd floor corner condo overlooking the Florida Bay and Yacht Club as your next vacation destination. Enjoy ...
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VRBO
From $376 per night (USD)
Expedia
LONE PALM COTTAGE ~ 3 BR, 2 Ba Home w/ 2 Cottages, Pool & Parking!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
OLD TOWN AMBIENCE.... This home with 2 mini cottages captures the essence of time-honored Key West living from the mome ...
From $376 per night (USD)
Expedia
From $561 per night (USD)
VRBO
Coral Reef Suite | 1 bed, 1 bath monthly rental near Key West's historic waterfront
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Experience the Heart of Key West from This Charming Monthly Vacation Retreat! Stay just steps from the action in this b ...
From $561 per night (USD)
VRBO
From $141 per night (USD)
VRBO
Apartment in historical hotel/home downtown Key West, one block off Duval St.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
A beautiful loft style apartment in a historical hotel/home in the heart of Key West awaits you! There is an 8ft deep pr ...
From $141 per night (USD)
VRBO
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VRBO
Check out Hemmingway's 1st residence in the heart of downtown Key West!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Want to live in paradise on a beautiful island for a month? Check out Hemmingway's 1st residence in the heart of downtow ...
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VRBO
From $222 per night (USD)
Expedia
Margaretaville in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This 2 bedroom, 2 bath home instantly transports you into the Key West lifestyle with its living space, balcony, and dec ...
From $222 per night (USD)
Expedia
From $908 per night (USD)
VRBO
OLD TOWN: 4 EN SUITES, POOL, PRIVATE PARKING STEPS TO DUVAL
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
Just a block and half from iconic Duval Street, this beautifully renovated home blends classic Conch style charm with mo ...
From $908 per night (USD)
VRBO
From $225 per night (USD)
Expedia
Charming 2 Bedroom Cottage in Old Town Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Tucked away in a quiet Old Town Key West neighborhood you'll find Nauti's Nest, a cozy and comfortable two bedroom cotta ...
From $225 per night (USD)
Expedia
From $428 per night (USD)
VRBO
** FLIGHT OF THE FLAMINGO @ OLD TOWN ** Home & Private Pool + LAST KEY SERVICES.
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! After landing ...
From $428 per night (USD)
VRBO
From $568 per night (USD)
VRBO
The Meadows Retreat
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Your Island Escape Awaits – Tropical Luxury in the Heart of Key West Welcome to your dream getaway in the Florida Keys— ...
From $568 per night (USD)
VRBO
From $251 per night (USD)
VRBO
Southard Quarter at Truman Annex | Walk to Duval
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Welcome to one of the most sought-after neighborhoods in Key West—Truman Annex. This quiet, gated community is known for ...
From $251 per night (USD)
VRBO
From $558 per night (USD)
Expedia
Hyatt Sunset Harbor Key West 1 Bedroom
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Hyatt Residence Club Sunset Harbor has the best location in the heart of Key West’s famed Old Town. Walk to Mallory Squa ...
From $558 per night (USD)
Expedia
From $755 per night (USD)
VRBO
Hyatt Sunset Harbor Key West 2 Bedroom
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Hyatt Residence Club Sunset Harbor has the best location in the heart of Key West’s famed Old Town. Walk to Mallory Squa ...
From $755 per night (USD)
VRBO
From $204 per night (USD)
VRBO
Rooftop Renaissance - Upscale Condo in Old Town Key West. Perfect for Couples.
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
Rooftop Renaissance vacation rental falls into a distinctive design category of Heritage Victorian - Meets Modern Luxury ...
From $204 per night (USD)
VRBO
From $900 per night (USD)
VRBO
Hemingway Retreat Suite at Suite Dreams Inn
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
1 king bedroom with en suite bath, 1 queen bedroom with en suite bath, Full Kitchen, Dining Room, Living Room with Comfo ...
From $900 per night (USD)
VRBO
From $612 per night (USD)
VRBO
Key West Sunset Suite at Suite Dreams Inn
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
1 Queen Bedroom, 1 California King Bedroom, 1 Bathroom, Full Kitchen with dishwasher, Living Room with Double Trundle S ...
From $612 per night (USD)
VRBO
From $413 per night (USD)
VRBO
Charming two floor 1-bedroom bed & breakfast in fantastic Key West with AC
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Key West is waiting for you at this 1-bedroom bed & breakfast. A brilliant king bed awaits guests in this peaceful retre ...
From $413 per night (USD)
VRBO
From $410 per night (USD)
Expedia
**THE ARTIST’S AVIARY @ OLD TOWN** Newly Renovated Home & Pool + LAST KEY SERVIC
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! There’s no be ...
From $410 per night (USD)
Expedia
From $736 per night (USD)
VRBO
Waterfront Condo with FREE Slip & Pool 2B/2B in Key West with AC
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Key West Waterfront Paradise – FREE Boat Slip Included! Wake up to breathtaking marina views, unwind in the heated pool ...
From $736 per night (USD)
VRBO
From $1856 per night (USD)
Expedia
Hyatt Sunset Harbor Resort- 2 Bedroom Villa- Old Town Key West- Walk Everywhere
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This is a great OCEANFRONT villa with a large balcony to watch sunsets! Hyatt Sunset Harbor is perfectly located in down ...
From $1856 per night (USD)
Expedia
From $538 per night (USD)
VRBO
Luxury Mansion in Old Town Key West – Four Bedrooms, Private Pool
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Island Dreaming – Your Luxury Key West Getaway Welcome to Paradise Discover the ultimate island retreat at Island Dream ...
From $538 per night (USD)
VRBO
From $1206 per night (USD)
Expedia
ELIZABETH'S SECRET: 3/2 In Old Town Key West, with a Private pool and Parking
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Elizabeth's Secret! You have found your secret! A very private and secluded tropical oasis awaits you behin ...
From $1206 per night (USD)
Expedia
From $719 per night (USD)
VRBO
Key West Condo 2B/2B with Pool & Boat FREE Slip
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Key West Waterfront Paradise – Dockage Included! Escape to our charming Key West condo, where relaxation and adventure ...
From $719 per night (USD)
VRBO
From $336 per night (USD)
Expedia
The Conch Republic Cooler
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to The Conch Republic Cooler! Nestled in the heart of quiet downtown Key West on the tranquil One Way Street, th ...
From $336 per night (USD)
Expedia
From $1350 per night (USD)
VRBO
Escape to Luxe 2BR Hyatt Sunset Harbor Villa! Dec 21-26, 3-Night Min Stay
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Your Key West Paradise at Hyatt Vacation Club at Sunset Harbor. All fees included! Discover an unforgettable escape in ...
From $1350 per night (USD)
VRBO
From $317 per night (USD)
VRBO
Charming bed & breakfast suite by the pool in lovely Key West.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Nestled in Key West, this delightful bed & breakfast features a cozy bedroom with a king bed, a bathroom with a refreshi ...
From $317 per night (USD)
VRBO
From $695 per night (USD)
VRBO
Hyatt Sunset Harbor - 1 bedroom sleep 4 condo steps from Duval & Mallory Square
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Hyatt Sunset Harbor Resort is located right on the water in the heart of Key West. Steps away is the famous Mallory Squa ...
From $695 per night (USD)
VRBO
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Expedia
Bahari House | Key West Home w/ Balcony, & Steps to Ocean & Bars
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Top reasons to book: - Downtown Location - 3 Minute Walk to the beach - Grocery Store Nearby - Close to Bars & Rest ...
Click For Pricing
Expedia
From $309 per night (USD)
VRBO
Hyatt Vacation Club in Key West- Studio
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Key West at its best. Hyatt Sunset Harbor resort directly overlooking the gulf. Just 1 block to Mallory Square and the w ...
From $309 per night (USD)
VRBO
From $374 per night (USD)
VRBO
The Kaleidoscope House - A Colorful Key West Hideaway w Pool & Jacuzzi
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
A camera roll full of the best family vacation memories is inevitable at The Kaleidoscope House: A Colorful Key West Sta ...
From $374 per night (USD)
VRBO
From $584 per night (USD)
VRBO
THE WRITER'S COTTAGE ~ Renovated 2 BR/2 Ba Home w/ Parking!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
NOSTALGIC AND INSPIRATIONAL HAVEN... History permeates and echoes through the classic Dade Pine details of this lovingly ...
From $584 per night (USD)
VRBO
From $1245 per night (USD)
Expedia
Luxe Designer Oasis + Guest House steps off Duval
Bedrooms:
6
Bathrooms:
6
Sleeps:
12
Discover unparalleled luxury at Autograph House, an exclusive private oasis just one block from the center of Key West. ...
From $1245 per night (USD)
Expedia
From $383 per night (USD)
VRBO
Southernmost Seclusion, central to Old Town hot spots. Pool, balconies, parking
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
- Two private outdoor spaces – greet the sunrise on the covered balcony, toast the sunset on a second, tree‑top perch. ...
From $383 per night (USD)
VRBO
From $333 per night (USD)
Expedia
10% Off Adv Rate-Upgraded Cottage-Steps to Famous Duval Street &Historic Seaport
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Offering an additional 10% off current advertised rate on all bookings. Located in the historic district of Key West thi ...
From $333 per night (USD)
Expedia
From $642 per night (USD)
VRBO
AZURE KEY WEST - Stunning New Home with Heated Pool - 4 Bedrooms Available
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Unwind in Key West at this lovely villa. Completely renovated top-to-bottom and completed in 2025, with 4 bedrooms inclu ...
From $642 per night (USD)
VRBO
From $784 per night (USD)
Expedia
NEW LISTING 4 ENSUITE BEDROOMS , OLD TOWN, PARKING, AC, POOL, BLOCK FROM DUVAL
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Discover Key West at its finest from your private luxury retreat just a block and a half off Duval Street. Newly renova ...
From $784 per night (USD)
Expedia
From $830 per night (USD)
VRBO
**BOHEMIA @ OLD TOWN** Fully Renovated Home & 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! Welcome to BO ...
From $830 per night (USD)
VRBO
From $569 per night (USD)
Expedia
Blanco Luxury Villa | 4 bedrooms & 4 baths in the heart of Old Town
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Welcome to Blanco Luxury Villa, your dream getaway in the heart of Old Town Key West. Located near the waterfront in Ol ...
From $569 per night (USD)
Expedia
From $799 per night (USD)
VRBO
Old Town 3/3 Home, Private Pool, Off Street Parking, Outdoor Dining, Balconies
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Welcome to paradise in Old Town Key West! This spacious 3BR/3BA home features gorgeous hardwood floors, a huge dining ro ...
From $799 per night (USD)
VRBO

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Fleming Key Rentals

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Results: 763 Rentals