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 $819 per night (USD)
VRBO
**PERFECT HARMONY @ MIDTOWN** Home & Pool + LAST KEY SERVICES…
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! PERFECT HARMO ...
From $819 per night (USD)
VRBO
$Lavender on White - 3 BD \/2 BA House w\/ Private Heated Pool and great Kitchen$
From $345 per night (USD)
Expedia
Lavender on White - 3 BD \/2 BA House w\/ Private Heated Pool and great Kitchen
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Nestled in a prime location, Lavender on White offers the perfect blend of tranquility and accessibility. Situated in th ...
From $345 per night (USD)
Expedia
$Priced to Book! 1BR\/1BA Walking distance to Duval St.$
Click For Pricing
VRBO
Priced to Book! 1BR\/1BA Walking distance to Duval St.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Great location in Key West. The Galleon is Walking distance to shopping, bars, dining, trolley, marina, Duval st., Mallo ...
Click For Pricing
VRBO
Click For Pricing
Expedia
Key West “Blue Zone” Oasis with Pool, Pet Friendly
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
Unwind and reconnect with nature at our tranquil VRBO property. As you enter the serene sanctuary, you'll be enveloped b ...
Click For Pricing
Expedia
From $888 per night (USD)
VRBO
The Crystalmarine Suite – Rustic Luxury on the Sea
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Romantic getaway on the sea with panoramic views of the ocean. Capture each sunrise and sunset on board this one-of-a-ki ...
From $888 per night (USD)
VRBO
From $685 per night (USD)
VRBO
Angela’s Conch Cottage - Old Town “Extraordinary home & heated pool”
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Angela’s Conch Cottage, as seen on HG TV's House Hunters, is located in the heart of Old Town Key West, across from the ...
From $685 per night (USD)
VRBO
From $295 per night (USD)
VRBO
Peaceful and relaxing setting with the feel of the island!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
$6,000 per month in Summer If Key West is on your itinerary, make this welcoming, conveniently located one-bedroom home ...
From $295 per night (USD)
VRBO
From $450 per night (USD)
Expedia
Beautiful Two-Bed, Two-Bath Suite at Galleon Resort Overlooking Harbor
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Our space is a lovely two-bedroom, two-bathroom serviced apartment with harbor views located on the second floor of The ...
From $450 per night (USD)
Expedia
From $1419 per night (USD)
VRBO
Bayview Manor at Paradise Harbor with Private Pool and Dock!
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Enjoy casual elegance with a view of famous Garrison Bight and centrally located on the edge of Old Town. This home boas ...
From $1419 per night (USD)
VRBO
From $1724 per night (USD)
Expedia
Kemp House in Key West
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
FALL DISCOUNTS!This Civil War Era home sits in Key West's most desirable Historic Seaport District, less than a block fr ...
From $1724 per night (USD)
Expedia
From $579 per night (USD)
VRBO
LUXURY Retreat in Old Town, Key West!
Bedrooms:
3
Bathrooms:
1
Sleeps:
4
Historic 1880's home awarded by the Historic Florida Keys Foundation in a prime old town location. A mere 5 blocks from ...
From $579 per night (USD)
VRBO
Click For Pricing
Expedia
Adorable Cottage Retreat in the Heart of Old Town - Steps from Duval - Pool!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Escape to the heart of Old Town Key West and experience the perfect blend of historic charm and modern comfort. This bea ...
Click For Pricing
Expedia
From $894 per night (USD)
VRBO
SEAPORT SAILING at Galleon Resort—Southernmost Regatta-Marina-Beach-Pool-BBQ
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
OCEANFRONT CASUAL LUXURY MARINA PENTHOUSE CONDO RENTAL WITH BREATHTAKING VIEWS OF KEY WEST HARBOR AND THE GULF OF MEXICO ...
From $894 per night (USD)
VRBO
$Dog-friendly downtown home & casita with patio, W\/D, & central\/partial AC$
Click For Pricing
Expedia
Dog-friendly downtown home & casita with patio, W\/D, & central\/partial AC
Bedrooms:
5
Bathrooms:
6
Sleeps:
12
Sunshine Stunner & Casita Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ent ...
Click For Pricing
Expedia
From $1233 per night (USD)
VRBO
**TRUMAN’S TROVE @ THE ANNEX** Private Home & Pool + LAST KEY SERVICES…
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Hunting for t ...
From $1233 per night (USD)
VRBO
From $208 per night (USD)
Expedia
Blue Heron by AvantStay | Pool & BBQ in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
*This condo is available for 28+ day stays only, and the pool area is shared with 3 other condos.* Welcome to our charm ...
From $208 per night (USD)
Expedia
Click For Pricing
Expedia
Waterfront resort where you can enjoy restaurants &more within walking distance
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Nestled in the heart of Old Town Key West, The Galleon Resort & Marina has been the vacation choice of many families and ...
Click For Pricing
Expedia
From $2433 per night (USD)
Expedia
Combined Bayview Manor and Bayview Retreat, accommodating up to 22 guests!
Bedrooms:
7
Bathrooms:
9
Sleeps:
22
Enjoy the comfort of accommodating up to 22 guests, in beds, over two luxury waterfront homes on Garrison Bight! Central ...
From $2433 per night (USD)
Expedia
From $614 per night (USD)
VRBO
NEW MONTHLY LISTING! Seacret Paradise: Desirable Oasis in the Heart of Old Town
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Charming Key West Oasis - Perfect Blend of Tranquility and Vibrancy! Escape to a hidden gem nestled on a serene lane be ...
From $614 per night (USD)
VRBO
$Hyatt Vacation Club at Sunset Harbor\n2 Bedroom$
From $1278 per night (USD)
Expedia
Hyatt Vacation Club at Sunset Harbor\n2 Bedroom
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
Tropical Key West welcomes you to a classic Florida villa offering a primary room with a plush king bed and connecting b ...
From $1278 per night (USD)
Expedia
$Quaint Key West Getaway: Historic Knowles House w\/Private Pool & Rooftop Deck$
From $3314 per night (USD)
VRBO
Quaint Key West Getaway: Historic Knowles House w\/Private Pool & Rooftop Deck
Bedrooms:
8
Bathrooms:
7
Sleeps:
16
Short walk to famous Duval Street. Central location. Restaurants nearby. Surrounded by charm of Key West. Convenience of ...
From $3314 per night (USD)
VRBO
From $2306 per night (USD)
Expedia
1983 65 foot Hatteras Motor Yacht
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
You and your friends and family will Spend your days like royalty aboard a fully refurbished Hatteras Motor Yacht. Exper ...
From $2306 per night (USD)
Expedia
From $1464 per night (USD)
VRBO
Truman House in Key West
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
The Keys have some of the most charming, top-rated vacation residences in the world. Truman House, a 1920's Conch home w ...
From $1464 per night (USD)
VRBO
From $408 per night (USD)
Expedia
Bohemian island home full of color and modern amenities - in a great location
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Casa Del Sol Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $408 per night (USD)
Expedia
Click For Pricing
VRBO
5 Star Timeshare Resort - The Galleon located in Old Key West, Florida
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The Galleon, in the heart of "Old Town Key West" located on the historic Seaport/Marina and a short walk to world famous ...
Click For Pricing
VRBO
From $669 per night (USD)
VRBO
Harrison's Hideaway-Sleeps up to 4, K & F Sl Sofa!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Historic Harrison's Hideaway is in an 1880's Cigar Maker's cottage renovated in 2010. It features a K size Pottery Barn ...
From $669 per night (USD)
VRBO
Click For Pricing
VRBO
Beautifully decorated home located in the White Street Gallery District.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
On The Rocks is a beautifully renovated and decorated home located in the White Street Gallery District. It combines the ...
Click For Pricing
VRBO
From $283 per night (USD)
Expedia
Windsor Cottage | Quaint Old Town Home
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Perfectly located in the heart of Old Town, this contemporary cottage offers an ideal and central location. New ...
From $283 per night (USD)
Expedia
From $267 per night (USD)
VRBO
NEW! Treasure Trove | One-of-a-Kind Key West Loft
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Dating back to 1919, Casa Antigua has a rich history as a one-of-a-kind property in downtown Key West. As one o ...
From $267 per night (USD)
VRBO
From $402 per night (USD)
Expedia
Snowbird-friendly oasis with private heated pool, lush yard, & ample parking
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
The Orchid House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $402 per night (USD)
Expedia
Click For Pricing
VRBO
OLD TOWN LUXURY HOME - completely remodeled, updated, steps to Duval Street.
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Located in the heart of Old Town, this rare home has 3 Bedrooms with 3.5 Baths in the Main House. New in 2021 to the hig ...
Click For Pricing
VRBO
From $338 per night (USD)
Expedia
Downtown Sunset Harbor Studio!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This is a great studio unit at Hyatt Sunset Harbor in downtown Key West. Walk along the boardwalk or head to Duval Stree ...
From $338 per night (USD)
Expedia
$Casa Tranquila-2 bedroom 2 bath Old Town home w\/ jacuzzi, outdoor grill$
Click For Pricing
Expedia
Casa Tranquila-2 bedroom 2 bath Old Town home w\/ jacuzzi, outdoor grill
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their parents and prim ...
Click For Pricing
Expedia
$ALL INCLUSIVE! Snorkel\/Sail\/Spear Fish\/Fishing\/Fun\n$
Click For Pricing
Expedia
ALL INCLUSIVE! Snorkel\/Sail\/Spear Fish\/Fishing\/Fun\n
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
You will love staying on this 45' GulfStar Sloop. The boat boasts 2 BR, 1.5 bath with shower, full working galley, A/C t ...
Click For Pricing
Expedia
From $194 per night (USD)
VRBO
Bird of Paradise | Cute cottage built for 2 in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Immerse yourself in the pinnacle of refined island living at The Bird of Paradise, gracefully positioned along the estee ...
From $194 per night (USD)
VRBO
From $255 per night (USD)
Expedia
Lazy Lane Cottage in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
A picturesque lane plus a charming 2 bedroom, 2 full bath conch cottage set the scene for your best vacation ever. Wheth ...
From $255 per night (USD)
Expedia
From $258 per night (USD)
VRBO
Cozy 2-bedroom cottage in Old Town Key West, with shared pool
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This memorable cottage is the perfect home base for your trip to Key West. With 2 bedrooms, including 1 king bed and 1 q ...
From $258 per night (USD)
VRBO
From $957 per night (USD)
Expedia
THREE ARCHES IN PARADISE~ A Mediterranean marvel in a walkable location!
Bedrooms:
4
Bathrooms:
3
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 $957 per night (USD)
Expedia
From $624 per night (USD)
VRBO
Traditional Two Queen, Pier House, Comfortable Ambiance, next to Nightlife Sight
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $624 per night (USD)
VRBO
From $301 per night (USD)
Expedia
LA CASITA EN CIMA~ Enjoy Key West in this lovely gem with a heated pool.
Bedrooms:
2
Bathrooms:
3
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 $301 per night (USD)
Expedia
From $411 per night (USD)
VRBO
**THE WICKED TUNA @ THE SEAPORT** Private Home & Pool + LAST KEY SERVICES…
Bedrooms:
3
Bathrooms:
2
Sleeps:
5
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Get ready to ...
From $411 per night (USD)
VRBO
From $1068 per night (USD)
Expedia
**CASA AVILA @ OLD TOWN** Private Home & 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! CASA AVILA co ...
From $1068 per night (USD)
Expedia
$\t\nBeautiful 2-bedroom resort in Key West Florida with AC, WiFi. spa tub, pool$
From $1019 per night (USD)
VRBO
\t\nBeautiful 2-bedroom resort in Key West Florida with AC, WiFi. spa tub, pool
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Discover the beauty of Key West from this 2-bedroom resort. The spacious bedrooms feature a king and queen bed, perfect ...
From $1019 per night (USD)
VRBO
From $458 per night (USD)
Expedia
Hollinsed House Studio - Great Location!!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Welcome to Harvey's Haven—a beautiful studio in the heart of Old Town Key West! Conveniently located at the Hollinsed Ho ...
From $458 per night (USD)
Expedia
From $1434 per night (USD)
VRBO
**SPIRIT OF KEY WEST @ OLD TOWN** Exquisite Home & Pool + LAST KEY SERVICES…
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! SPIRIT OF KEY ...
From $1434 per night (USD)
VRBO
From $1356 per night (USD)
Expedia
1-Bedroom Suite at a 4⭐️ Hotel
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
1 King Bed600-sq-foot (56-sq-meter) room, balcony with ocean viewsLayout - Bedroom Internet - Free WiFi Entertainment - ...
From $1356 per night (USD)
Expedia
$Dog-friendly condo near beach with pool, grill, outdoor shower, W\/D, AC$
From $229 per night (USD)
VRBO
Dog-friendly condo near beach with pool, grill, outdoor shower, W\/D, AC
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Paradise on Packer Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $229 per night (USD)
VRBO
From $802 per night (USD)
Expedia
The Perch on Duval- Hip & Modern Duval Suite
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Welcome to Perch on Duval, an elegant and charming 2-bedroom vacation rental situated in the heart of downtown Key West. ...
From $802 per night (USD)
Expedia
From $1356 per night (USD)
VRBO
1-Bedroom Suite at a 4⭐️ Hotel
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
1 King Bed600-sq-foot (56-sq-meter) room, balcony with ocean viewsLayout - Bedroom Internet - Free WiFi Entertainment - ...
From $1356 per night (USD)
VRBO
From $710 per night (USD)
Expedia
Ann Street Gardens in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
The cottage is a cozy hideaway. The poolside area is picture-postcard perfect. The location is in the very heart of Key ...
From $710 per night (USD)
Expedia
From $433 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 $433 per night (USD)
VRBO
From $529 per night (USD)
VRBO
KNOT A WORRY so close to Duval at this monthly rental
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, you' ...
From $529 per night (USD)
VRBO
$Casa Loca - so close to Duval 3bd\/2ba private home$
From $1541 per night (USD)
VRBO
Casa Loca - so close to Duval 3bd\/2ba private home
Bedrooms:
3
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 $1541 per night (USD)
VRBO
From $606 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 $606 per night (USD)
VRBO
From $235 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 $235 per night (USD)
VRBO
From $475 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 $475 per night (USD)
Expedia
From $1977 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 $1977 per night (USD)
VRBO
From $1741 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 $1741 per night (USD)
VRBO
From $1006 per night (USD)
VRBO
Everything Key West has to offer @ Mango Cottage
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This historic Conch house is an excellent vacation home which has been thoughtfully remodeled to provide the best in mod ...
From $1006 per night (USD)
VRBO
From $508 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 $508 per night (USD)
VRBO
From $1147 per night (USD)
VRBO
Heart of Key West - 2BR Waterfront at the Galleon Resort
Bedrooms:
2
Bathrooms:
3
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 $1147 per night (USD)
VRBO
From $1013 per night (USD)
Expedia
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 $1013 per night (USD)
Expedia
From $1117 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 $1117 per night (USD)
VRBO
$MIMOSAS ON PINE ~ 3 Bedroom, 2.5 Bath Home w\/ Pool & Spa in The Meadows!$
From $429 per night (USD)
Expedia
MIMOSAS ON PINE ~ 3 Bedroom, 2.5 Bath Home w\/ Pool & Spa in The Meadows!
Bedrooms:
3
Bathrooms:
4
Sleeps:
7
YOUR STORYBOOK COTTAGE... This island delight is tucked away on a vibrant and secluded street of The Meadows neighborhoo ...
From $429 per night (USD)
Expedia
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
$Bring your umbrella drinks @Tiki Beach Too! Shipyard 2bed\/2bath$
From $471 per night (USD)
Expedia
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 $471 per night (USD)
Expedia
From $135 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 $135 per night (USD)
VRBO
From $799 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 $799 per night (USD)
Expedia
From $1860 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 $1860 per night (USD)
VRBO
From $1024 per night (USD)
Expedia
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 $1024 per night (USD)
Expedia
$DREAM ON ~ Perfectly Located and Renovated 3 BR, 2 Ba Home w\/ Outdoor Shower!$
From $229 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 $229 per night (USD)
VRBO
$Paradise found! 2 br\/1 bth restored Old Town home with private cocktail pool$
From $459 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 $459 per night (USD)
VRBO
From $1392 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 $1392 per night (USD)
VRBO
From $370 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 $370 per night (USD)
VRBO
$AMBER COTTAGE ~ Renovated 3 Bedroom, 3.5 Bathroom Home w\/ Pool!$
From $477 per night (USD)
VRBO
AMBER COTTAGE ~ Renovated 3 Bedroom, 3.5 Bathroom Home w\/ Pool!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
AN ISLAND STUNNER... This is the back cottage of the delightful Jewel Box Cottages compound, located in Old Town, just s ...
From $477 per night (USD)
VRBO
From $492 per night (USD)
Expedia
PEARL COTTAGE ~ 3 Bedroom, 3.5 Bathroom Home with Pool!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
CONCH STYLE CHARM... This is the front cottage of the delightful Jewel Box Cottage compound, located in Old Town, just a ...
From $492 per night (USD)
Expedia
$JEWEL BOX COTTAGES ~ Lush Compound with 2 Renovated Homes w\/ Private Pools!$
From $852 per night (USD)
VRBO
JEWEL BOX COTTAGES ~ Lush Compound with 2 Renovated Homes w\/ Private Pools!
Bedrooms:
7
Bathrooms:
8
Sleeps:
16
BEDAZZLING COMPOUND... Two delightful conch style island homes are situated on one glorious parcel in Old Town, just a s ...
From $852 per night (USD)
VRBO
From $185 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 $185 per night (USD)
VRBO
From $447 per night (USD)
VRBO
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 $447 per night (USD)
VRBO
$Recently Relisted 2BR\/2BA with Private Heated Pool - 188 steps to Duval$
From $729 per night (USD)
Expedia
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 $729 per night (USD)
Expedia
From $1077 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 $1077 per night (USD)
VRBO
$**SOUL OF DUVAL @ DUVAL** Modern\/Centrally Located + LAST KEY SERVICES...$
From $881 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 $881 per night (USD)
Expedia
From $934 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 $934 per night (USD)
VRBO
From $207 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 $207 per night (USD)
VRBO
$Cottage in Old Town Key West w\/ Pool, Parking and Privacy. One block from Duval!$
From $243 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 $243 per night (USD)
VRBO
$Spacious Updated Waterfront Condo, 2\/2 Pool, Dock$
From $948 per night (USD)
VRBO
Spacious Updated Waterfront Condo, 2\/2 Pool, Dock
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
<p>Close to cycling, the sea, and more, this pet-friendly condo brings it all within reach. Studios of Key West is withi ...
From $948 per night (USD)
VRBO
From $398 per night (USD)
VRBO
Casa Bella Petite le Bleu - Luxury Key West Cottage w Pool - 2 Blocks Off Duval
Bedrooms:
2
Bathrooms:
3
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 $398 per night (USD)
VRBO
From $1094 per night (USD)
VRBO
Bella Grand Premier Estate Key West - 2 Blocks off Duval w Private Pool
Bedrooms:
6
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 $1094 per night (USD)
VRBO
$Waterfront Penthouse sleeps 16 w\/Pool & Boat Dock$
From $1392 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 $1392 per night (USD)
VRBO
From $305 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 $305 per night (USD)
VRBO
From $734 per night (USD)
VRBO
Paradise on White Street
Bedrooms:
4
Bathrooms:
5
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 $734 per night (USD)
VRBO
$Key West Island Rendezvous - Private Compound Steps Off Duval w\/Pool - Sleeps 12$
From $2016 per night (USD)
Expedia
Key West Island Rendezvous - Private Compound Steps Off Duval w\/Pool - Sleeps 12
Bedrooms:
5
Bathrooms:
7
Sleeps:
12
Island Rendezvous vacation rental offers the perfect solution for a gathering of family or friends who desire to be in t ...
From $2016 per night (USD)
Expedia
From $1924 per night (USD)
VRBO
Pavilion Villa – A Key West Private Paradise 1 Block Off Duval w Pool
Bedrooms:
3
Bathrooms:
5
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 $1924 per night (USD)
VRBO
$Down Island Digs - 2BR Cottage 1 Block off Duval Street Key West w\/Private Pool$
From $875 per night (USD)
Expedia
Down Island Digs - 2BR Cottage 1 Block off Duval Street Key West w\/Private Pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Everything about this historic Key West tropical gem adds up to make a precious private garden cottage. Sitting in the m ...
From $875 per night (USD)
Expedia
$\Island Time\ in Old Town$
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
$NEWTON'S NEST ~ Adult Only, 1 Bedroom, 1 Bath Condo w\/ Shared Pool!$
From $180 per night (USD)
Expedia
NEWTON'S NEST ~ Adult Only, 1 Bedroom, 1 Bath Condo w\/ Shared Pool!
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
SIMPLISTIC ELEGANCE... Enjoy easy tropical living in this quiet refuge located within Old Town where you can roost and i ...
From $180 per night (USD)
Expedia
From $1612 per night (USD)
VRBO
Key West Wabi Sabi - Authentic Downtown Cottage w Pool - Steps Off Duval
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 $1612 per night (USD)
VRBO
$Cottage in Old Town Key West w\/ Pool, Parking and Privacy. One block from Duval!$
From $279 per night (USD)
Expedia
Cottage in Old Town Key West w\/ Pool, Parking and Privacy. One block from Duval!
Bedrooms:
1
Bathrooms:
2
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 $279 per night (USD)
Expedia
From $2250 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 $2250 per night (USD)
VRBO
From $484 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 $484 per night (USD)
VRBO

Search Your Destination Now!

Fleming Key Rentals

Rental Rates ($USD weekly)

Guests

Check Rates & Availability:

Results: 805 Rentals