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 $226 per night (USD)
VRBO
Airy & Bright Home with Pool in Old Town
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
The perfect getaway for a long stay in Key West. A private pool and patio area lie behind a green gate on a quiet lane i ...
From $226 per night (USD)
VRBO
From $438 per night (USD)
Expedia
~ASHE HOUSE~ Renovated and relaxing with pool, porches, and privacy!
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 $438 per night (USD)
Expedia
From $154 per night (USD)
VRBO
ANCHORS AWAY ~ Cheerful 1 BR, 1 Ba Condo with Private Hot Tub in The Meadows!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
CLASSIC AND COZY... Exhale your worries away as you approach this delightful condo, one of four that are situated insid ...
From $154 per night (USD)
VRBO
From $254 per night (USD)
Expedia
Garden of Eden Cottage | 1 Bed, 1.5 Bath
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
Experience paradise at our Key West Cottage vacation rental - a hidden gem tucked away in a lush Garden of Eden. This ch ...
From $254 per night (USD)
Expedia
From $291 per night (USD)
VRBO
Old Town Key West Live like a local
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Live like a local! This vacation flat is located at Mile marker 1, and sits nestled above the street right on Truman Av ...
From $291 per night (USD)
VRBO
$BRIGHT SUNSHINY DAY ~ Renovated 3 BR, 4 Ba Home w\/ Pool, Spa & Exercise Room!$
From $458 per night (USD)
Expedia
BRIGHT SUNSHINY DAY ~ Renovated 3 BR, 4 Ba Home w\/ Pool, Spa & Exercise Room!
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
OLD TOWN CLASSIC... This beautifully redesigned Conch house is in the heart of Key West. Located in the outstanding loc ...
From $458 per night (USD)
Expedia
$**SOUL OF DUVAL @ DUVAL** Modern\/Centrally Located + LAST KEY SERVICES...$
From $593 per night (USD)
VRBO
**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 $593 per night (USD)
VRBO
$THE WEEKEND HOUSE ~ 3 Bedroom, 2 Bath Condo Centrally Located w\/ Pool!$
From $300 per night (USD)
Expedia
THE WEEKEND HOUSE ~ 3 Bedroom, 2 Bath Condo Centrally Located w\/ Pool!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
WHERE LIFE IS PURE… This dreamy 3 bedroom, 2 bathroom island getaway is sure to captivate the true essence of Key West c ...
From $300 per night (USD)
Expedia
From $118 per night (USD)
VRBO
Adorable gated loft studio two blocks from Duval in Old Town - Location Location
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The Sanctuary is tucked away on a quiet street just two blocks off Duval St. in Old Town Key West. This hidden gem is on ...
From $118 per night (USD)
VRBO
From $899 per night (USD)
VRBO
Stunning Views at The Galleon Resort in Beautiful Key West! Charming 2 Bed!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Concierge Realty is proud to present luxury villas at The Galleon Resort! **Reservations are available in weekly (7 nig ...
From $899 per night (USD)
VRBO
From $294 per night (USD)
VRBO
Ultimate Escape-2 bed 2 bath Old Town home, parking, open layout, Mid-century
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
AGE REQUIREMENT: Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their ...
From $294 per night (USD)
VRBO
From $501 per night (USD)
Expedia
Cozy Houseboat “Wild One”
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
We invite you to stay at our unique houseboat “Wild One”. Wild One is anchored minutes (by boat) from Garrison Bight Mar ...
From $501 per night (USD)
Expedia
From $874 per night (USD)
VRBO
**THE GILDED PINEAPPLE @ THE SEAPORT** Gorgeous Home & Pool + LAST KEY SERVICES…
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! THE GILDED PI ...
From $874 per night (USD)
VRBO
From $382 per night (USD)
Expedia
Conch Cottage Retreat in the heart of Old Town Key West
Bedrooms:
3
Bathrooms:
2
Sleeps:
5
Experience Old Town Key West in a classic conch home! This home is only steps from shopping, restaurants, the historic s ...
From $382 per night (USD)
Expedia
From $524 per night (USD)
VRBO
Two fully independent units in a Duplex, with independent entrances. One Rent!
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
Welcome to "Old Key West". Our Classic Old Town style duplex, with two independent fully renovated homes in the same pro ...
From $524 per night (USD)
VRBO
$ELIZABETH'S SECRET: 3\/2 In Old Town Key West, with a Private pool and Parking$
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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 ...
Click For Pricing
Expedia
From $604 per night (USD)
VRBO
Private Parking & Pool, Pet Friendly - Casa Azul
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
Summary: Casa Azul is a luxe modern cottage with an open-concept living area that ends up filled with natural sunlight. ...
From $604 per night (USD)
VRBO
From $158 per night (USD)
Expedia
The Oasis: Stylishly Updated 1BR Home Convenient to Duval St & Beaches, Shared Pool & Pet-Friendly!
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
City of Key West zoning requires a minimum rental period of 30 days, and no exceptions can be made. Please review additi ...
From $158 per night (USD)
Expedia
$KALI ZOI HOUSE ~ Charming 3 BR\/3 Ba Home in Old Town w\/ Pool!$
From $344 per night (USD)
VRBO
KALI ZOI HOUSE ~ Charming 3 BR\/3 Ba Home in Old Town w\/ Pool!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
THE GOOD LIFE AWAITS... Kali Zoi is Greek for 'good life" and that is what you'll experience in this island retreat in t ...
From $344 per night (USD)
VRBO
From $883 per night (USD)
VRBO
SEAPORT SAILING at Galleon Resort-Beach-Pool-King Suite-BBQ-near Mallory Square
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 $883 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
$Ashe St Serenade: 3BD\/3.5BA Luxury Retreat, Private Pool in an Island Oasis.$
From $442 per night (USD)
Expedia
Ashe St Serenade: 3BD\/3.5BA Luxury Retreat, Private Pool in an Island Oasis.
Bedrooms:
4
Bathrooms:
4
Sleeps:
6
Welcome to your dream getaway in the charming Old Town Key West, where the tranquility of island living meets the excite ...
From $442 per night (USD)
Expedia
From $358 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 60 days prior to your arrival! PERFECT HARMO ...
From $358 per night (USD)
VRBO
$Lavender on White - 3 BD \/2 BA House w\/ Private Heated Pool and great Kitchen$
From $772 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 $772 per night (USD)
Expedia
$Priced to Book! 1BR\/1BA Walking distance to Duval St.$
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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
Click For Pricing
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 ...
Click For Pricing
VRBO
$Private Heated Pool-2BR\/2BA-Great OldTown Location-88 steps to Duval-Weekly Maid$
From $838 per night (USD)
Expedia
Private Heated Pool-2BR\/2BA-Great OldTown Location-88 steps to Duval-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 $838 per night (USD)
Expedia
From $150 per night (USD)
VRBO
THE HIDDEN GEM ~ Charming Renovated Studio with Large Community Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
HIDDEN GARDEN STUDIO… This charming 340 sq.ft. escape in the exclusive Lionsgate Condominium community will delight your ...
From $150 per night (USD)
VRBO
$AMBER COTTAGE ~ Renovated 3 Bedroom, 3.5 Bathroom Home w\/ Pool!$
From $405 per night (USD)
Expedia
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 $405 per night (USD)
Expedia
From $364 per night (USD)
VRBO
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 $364 per night (USD)
VRBO
$JEWEL BOX COTTAGES ~ Lush Compound with 2 Renovated Homes w\/ Private Pools!$
From $812 per night (USD)
Expedia
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 $812 per night (USD)
Expedia
From $200 per night (USD)
VRBO
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 $200 per night (USD)
VRBO
From $800 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 $800 per night (USD)
Expedia
$The Caroline Suite | 1 bed, 1 bath condo w\/shared pool$
From $399 per night (USD)
VRBO
The Caroline Suite | 1 bed, 1 bath condo w\/shared pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The Caroline Suite is in The Bayview House, a completely remodeled historic house built in 1928. The 4 units and shared ...
From $399 per night (USD)
VRBO
From $1176 per night (USD)
VRBO
The Cathouse, an Old Town tropical poolside oasis with huge, heated pool
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 $1176 per night (USD)
VRBO
From $775 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 $775 per night (USD)
VRBO
From $1646 per night (USD)
Expedia
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 $1646 per night (USD)
Expedia
From $796 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 $796 per night (USD)
VRBO
$DREAM ON ~ Perfectly Located and Renovated 3 BR, 2 Ba Home w\/ Outdoor Shower!$
From $284 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 $284 per night (USD)
Expedia
$Paradise found! 2 br\/1 bth restored Old Town home with private cocktail pool$
From $421 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 $421 per night (USD)
VRBO
From $1061 per night (USD)
Expedia
Kemp House in Key West
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
This Civil War Era home sits in Key West's most desirable Historic Seaport District, less than a block from the Gulf of ...
From $1061 per night (USD)
Expedia
From $184 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 $184 per night (USD)
VRBO
From $190 per night (USD)
Expedia
Charming + Circa 1889 Historic Eyebrow Home
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
28 Night Minimum. Welcome to "The Saltbox"! Featured in design magazines. 710 Ashe Street is a charming house circa 18 ...
From $190 per night (USD)
Expedia
From $355 per night (USD)
VRBO
524 Elizabeth St. #2
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Enjoy a stylish experience at this centrally-located place. Located just blocks from duval and many of it's restaurants ...
From $355 per night (USD)
VRBO
From $355 per night (USD)
Expedia
613 Fleming. St. Unit 1
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Great location in the heart of it all. Short walk to Duval Street, bars, shops and restaurants. Quiet enough to have a p ...
From $355 per night (USD)
Expedia
From $577 per night (USD)
VRBO
The Leonella, Old Town Key West.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The Leonella is an Imaginative and impeccable restoration of a Key West conch house mixing contemporary style and histor ...
From $577 per night (USD)
VRBO
From $989 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 $989 per night (USD)
VRBO
From $215 per night (USD)
VRBO
Peaceful and relaxing setting with the feel of the island!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
If Key West is on your itinerary, make this welcoming, conveniently located one-bedroom home yours and enjoy comfort an ...
From $215 per night (USD)
VRBO
From $894 per night (USD)
VRBO
SEAPORT PANORAMA at Galleon Resort-Beach-Pool-King Suite-BBQ-near Mallory Square
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
GALLEON RESORT LUXURY OCEANFRONT CONDO RENTAL 45 FT FROM THE WATER WITH BREATHTAKING 180 DEGREE FRONT & CORNER BALCONY V ...
From $894 per night (USD)
VRBO
$The Elizabeth Suite | 1 bed, 1 bath w\/shared pool$
From $398 per night (USD)
VRBO
The Elizabeth Suite | 1 bed, 1 bath w\/shared pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
We are pleased to introduce The Elizabeth Suite at The Bayview House, a nightly rental with shared pool. One of 4 units ...
From $398 per night (USD)
VRBO
$The Fleming Suite | 1 bed, 1 bath condo w\/shared pool$
From $398 per night (USD)
Expedia
The Fleming Suite | 1 bed, 1 bath condo w\/shared pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
We are pleased to introduce The Fleming Suite at The Bayview House, a 1-bedroom, 1-bathroom nightly rental with a shared ...
From $398 per night (USD)
Expedia
$Breezy Key West First-Floor Condo w\/ Pool Access$
From $152 per night (USD)
VRBO
Breezy Key West First-Floor Condo w\/ Pool Access
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Experience your next seaside vacation in style at this 2-bedroom, 2-bathroom Key West vacation rental. This 1st-floor co ...
From $152 per night (USD)
VRBO
From $1550 per night (USD)
Expedia
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 $1550 per night (USD)
Expedia
From $767 per night (USD)
VRBO
Key West Andros 2BR•Waterfront, Pool, Dock&Pet OK
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Time to fish & relax! Bring your family & friends to this 1350 sqft waterfront corner condo home. Boat slip a ...
From $767 per night (USD)
VRBO
From $405 per night (USD)
Expedia
Our Piece of Paradise-
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Welcome to your ideal Key West getaway! Perfect for families and ideally situated between Old Town, New Town, and Duval ...
From $405 per night (USD)
Expedia
From $461 per night (USD)
VRBO
Midnight Cowboy by AvantStay | 3 Artistic Spaces
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
*Please note that this home is available for 28+ night stays only.* Midnight Cowboy is a one-of-a-kind Key West escape ...
From $461 per night (USD)
VRBO
From $213 per night (USD)
Expedia
Tennessee Williams by AvantStay | Funky Design + Pool
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
*Please note that this home is available for 28+ night stays only.* Tennessee Williams is a one-of-a-kind Key West esca ...
From $213 per night (USD)
Expedia
From $962 per night (USD)
VRBO
Rooftop Penthouse, Walk to Duval - KAMP
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Stay in this one-of-a-kind penthouse and Jimmy Buffet's former Margaritaville Headquarters as well as David "Mr ...
From $962 per night (USD)
VRBO
From $389 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 $389 per night (USD)
Expedia
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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 $507 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 $507 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 ...
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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
$Amazing Location 3bed\/2bath & Swim Spa\n\n$
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VRBO
Amazing Location 3bed\/2bath & Swim Spa\n\n
Bedrooms:
2
Bathrooms:
3
Sleeps:
9
Fully furnished ground floor cottage with 3 bedrooms (queen bed in each), 2 full bathrooms, plus a loft with an addition ...
Click For Pricing
VRBO
From $4210 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 $4210 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 $610 per night (USD)
Expedia
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 $610 per night (USD)
Expedia
$Quaint Key West Getaway: Historic Knowles House w\/Private Pool & Rooftop Deck$
From $2978 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 Duval Street. Central location. Restaurants nearby. Surrounded by charm of Key West. 7 to 8 rooms with ens ...
From $2978 per night (USD)
VRBO
From $1204 per night (USD)
Expedia
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 $1204 per night (USD)
Expedia
$Bring your umbrella drinks @Tiki Beach Too! Shipyard 2bed\/2bath$
From $379 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 $379 per night (USD)
VRBO
Click For Pricing
Expedia
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
Expedia
$MIMOSAS ON PINE ~ 3 Bedroom 2.5 Bath Home w\/Pool & Great Spring\/Summer Deals!$
From $383 per night (USD)
VRBO
MIMOSAS ON PINE ~ 3 Bedroom 2.5 Bath Home w\/Pool & Great Spring\/Summer Deals!
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 $383 per night (USD)
VRBO
From $202 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 $202 per night (USD)
Expedia
From $650 per night (USD)
VRBO
Heart of Key West - 2BR Waterfront at the Galleon Resort
Bedrooms:
2
Bathrooms:
3
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 $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
From $1003 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 $1003 per night (USD)
VRBO
From $693 per night (USD)
Expedia
**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 60 days prior to your arrival! SPIRIT OF KEY ...
From $693 per night (USD)
Expedia
From $450 per night (USD)
VRBO
The Cozy Little Cottage!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Welcome to The Cozy Little Cottage !!! A REAL ISLAND GATAWAY IN KEY WEST!!! Nested in the heart of Key West, The Cozy L ...
From $450 per night (USD)
VRBO
From $331 per night (USD)
Expedia
Beautiful Old Town 2 bedroom Cottage on a Private Lane
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Located in the heart of Key West's historic district on a quiet lane with parking directly in front of the private gated ...
From $331 per night (USD)
Expedia
From $426 per night (USD)
VRBO
Spend your Holidays at Frogmore on Fleming in Downtown Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to your dream residence in the heart of Key West, Florida! Nestled in a prime location, this 2-bedroom apartment ...
From $426 per night (USD)
VRBO
$ALL INCLUSIVE! Snorkel\/Sail\/Spear Fish\/Fishing\/Fun\n$
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 $905 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 $905 per night (USD)
VRBO
$Dog-friendly condo near beach with pool, grill, outdoor shower, W\/D, AC$
From $175 per night (USD)
Expedia
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 $175 per night (USD)
Expedia
From $1033 per night (USD)
VRBO
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 $1033 per night (USD)
VRBO
From $130 per night (USD)
Expedia
Large 1 bedroom condo in the historic area of Key West!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Enjoy your Key West vacation in this spacious 623 square foot condo located on the second floor of this classical reviva ...
From $130 per night (USD)
Expedia
$PAGITT HOUSE - 3\/ 2 - OLD TOWN KEY WEST WITH POOL$
From $1572 per night (USD)
VRBO
PAGITT HOUSE - 3\/ 2 - OLD TOWN KEY WEST WITH POOL
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
NEW LISTINGS APRIL - 2024! Welcome to the Pagitt House built in 1933 and located on Elizabeth Street just steps to all ...
From $1572 per night (USD)
VRBO
Click For Pricing
Expedia
Studio Unit in quiet resort adjacent to Old Town Key West!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
With a coveted location in the heart of Old Town and magnificent views of the Gulf of Mexico, Sunset Harbor is the ultim ...
Click For Pricing
Expedia
$Escape to \Casa Escondida\$
From $439 per night (USD)
VRBO
Escape to \"Casa Escondida\"
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Escape to the enchanting "Casa Escondida," a historic Conch Style home with a modern twist, nestled on a tranquil, seclu ...
From $439 per night (USD)
VRBO
From $2140 per night (USD)
VRBO
Key West, Galleon Resort, Marina, In Town, Pool, Hot Tub
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to The Galleon Resort in Key West, where paradise meets luxury at the southernmost tip of the United States. In ...
From $2140 per night (USD)
VRBO
From $1596 per night (USD)
VRBO
Old Town Key West Retreat | Seaport Paradise Room with Pool Access | 3 Rooms
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $1596 per night (USD)
VRBO
$Spacious Key West Room w\/ Balcony | Outdoor Pools | Seaport Proximity$
From $600 per night (USD)
VRBO
Spacious Key West Room w\/ Balcony | Outdoor Pools | Seaport Proximity
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $600 per night (USD)
VRBO
$Family Old Town Key Getaway | Four Rooms w\/ Balcony & Outdoor Pools$
From $1939 per night (USD)
VRBO
Family Old Town Key Getaway | Four Rooms w\/ Balcony & Outdoor Pools
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $1939 per night (USD)
VRBO
$Vibrant Key West Stay w\/ Outdoor Pools | Four Rooms w\/ Balcony$
From $2124 per night (USD)
VRBO
Vibrant Key West Stay w\/ Outdoor Pools | Four Rooms w\/ Balcony
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $2124 per night (USD)
VRBO
$Two Relaxing Rooms w\/ Balcony | Waterfront Resort w\/ Access to Outdoor Pools$
From $1071 per night (USD)
VRBO
Two Relaxing Rooms w\/ Balcony | Waterfront Resort w\/ Access to Outdoor Pools
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $1071 per night (USD)
VRBO
$2 BR Spacious Suite w\/ Living Area and Balcony | Outdoor Pools$
From $3121 per night (USD)
VRBO
2 BR Spacious Suite w\/ Living Area and Balcony | Outdoor Pools
Bedrooms:
1
Bathrooms:
2
Sleeps:
8
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $3121 per night (USD)
VRBO
From $1717 per night (USD)
VRBO
Seaport Paradise Room with Pools | Old Town Key West Retreat | 3 Rooms
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $1717 per night (USD)
VRBO
$Seaport Proximity | Resort w\/ Outdoor Pools | Spacious Key West Room w\/ Balcony$
From $636 per night (USD)
VRBO
Seaport Proximity | Resort w\/ Outdoor Pools | Spacious Key West Room w\/ Balcony
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $636 per night (USD)
VRBO
$Spacious 2 BR Suite w\/ Living Area and Balcony | Onsite Parking Available$
From $2475 per night (USD)
VRBO
Spacious 2 BR Suite w\/ Living Area and Balcony | Onsite Parking Available
Bedrooms:
1
Bathrooms:
2
Sleeps:
8
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $2475 per night (USD)
VRBO
$Two Bedrooms Family Suite with Balcony | Idyllic Resort w\/ Outdoor Pools$
From $3121 per night (USD)
VRBO
Two Bedrooms Family Suite with Balcony | Idyllic Resort w\/ Outdoor Pools
Bedrooms:
1
Bathrooms:
2
Sleeps:
8
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $3121 per night (USD)
VRBO

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