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 $529 per night (USD)
VRBO
**MODERN IN THE MEADOWS @ THE MEADOWS** Chic Private Home & Pool + LAST KEY SERV
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! MODERN IN THE ...
From $529 per night (USD)
VRBO
From $619 per night (USD)
Expedia
Luxury Waterfront Stay @ The Galleon, Mins from Downtown
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Imagine waking up every morning in Paradise. With Balconies that overlook the marina and ocean. Private marina, private ...
From $619 per night (USD)
Expedia
From $2427 per night (USD)
VRBO
CLASSIC KEY WEST - Grand home in Old Town location
Bedrooms:
7
Bathrooms:
7
Sleeps:
14
The Mansion, circa 1840’s is a lovingly restored and renovated three story Classic Folk Victorian home with seven bedroo ...
From $2427 per night (USD)
VRBO
From $1131 per night (USD)
VRBO
PERFECTION...STEPS FROM DUVAL ~
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
The Villa is a newer built poolside home, situated steps away from famous Duval Street, the historic seaport and everyth ...
From $1131 per night (USD)
VRBO
From $273 per night (USD)
VRBO
Downtown Conch House-Historic Old Town 3 bedroom, 3 bath home w/private pool
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
AGE REQUIREMENT: Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their ...
From $273 per night (USD)
VRBO
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Expedia
The Queens Villa
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
Former Fantasy Fest Queens private residence. I also own the number one hotel in Key West. Best location at the END of ...
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Expedia
From $394 per night (USD)
VRBO
Unlock your Paradise Adventure - Between Sloppy Joe's and the Harbor
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This 4 story Townhouse is in "Old Town Villas". A Caribbean inspired community in the heart of Key West. Built in 2017. ...
From $394 per night (USD)
VRBO
$Two-bedroom townhouse overlooking the harbor.\n \nONLY AVAILABLE Nov. 9 - Nov 16$
From $900 per night (USD)
Expedia
Two-bedroom townhouse overlooking the harbor.\n \nONLY AVAILABLE Nov. 9 - Nov 16
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Two story townhouse with two bedrooms, pull out couch, full kitchen, three bathrooms. Overlooking the harbor with full ...
From $900 per night (USD)
Expedia
From $400 per night (USD)
VRBO
TROPICAL PROPERTIES VACATION RENTAL-KEY WEST
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
****This property requires a minimum stay of 28 nights in the same calendar month**** Tropical Properties Vacation Rent ...
From $400 per night (USD)
VRBO
From $3586 per night (USD)
VRBO
WATSON HOUSE GRAND ESTATE on Simonton St
Bedrooms:
11
Bathrooms:
11
Sleeps:
22
The Grand Estate is comprised of the Mansion and the Villa offering 11 bedrooms and baths. It is ideal for family gather ...
From $3586 per night (USD)
VRBO
$LOVE IS IN THE AIR - Charming Home-On private lane w\/pool sleeps 6$
From $406 per night (USD)
VRBO
LOVE IS IN THE AIR - Charming Home-On private lane w\/pool sleeps 6
Bedrooms:
3
Bathrooms:
3
Sleeps:
7
Enjoy a month-long stay or longer in this beautiful Three-bedroom Key West Home. Hidden in the heart of Old-Town Key W ...
From $406 per night (USD)
VRBO
From $748 per night (USD)
Expedia
**SOUTHERNMOST BLISS @ OLD TOWN** Newly Renovated Home & Pool + LAST KEY SERVICE
Bedrooms:
4
Bathrooms:
4
Sleeps:
9
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! SOUTHERNMOST ...
From $748 per night (USD)
Expedia
From $314 per night (USD)
VRBO
ESCAPE ON FLEMING - A charming 2 bedroom home
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
28 DAY MINIMUM RENTAL ... This property is not allowed to accept pets. Break away from it all at Escape on Fleming. Thi ...
From $314 per night (USD)
VRBO
From $416 per night (USD)
Expedia
The Conch Chateau: Stylishly Renovated Conch House in the Heart of Key West, Heated/Chilled Pool!
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
City of Key West zoning requires a minimum rental period of 30 days, and no exceptions can be made. Please review additi ...
From $416 per night (USD)
Expedia
From $248 per night (USD)
VRBO
Cottage in Old Town Key West w/ Pool, Parking and Privacy. One block from Duval!
Bedrooms:
2
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 $248 per night (USD)
VRBO
From $579 per night (USD)
VRBO
CONCH CASA @ The Colony ~ the perfect monthly escape
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
The property features a beautiful, heated community pool and one reserved off-street parking space (a coveted old town r ...
From $579 per night (USD)
VRBO
From $460 per night (USD)
VRBO
**ANGELA’S ECLECTIC GALLERY @ SOLARIS HILL** Exceptional Home & Pool + LAST KEY
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! On an island ...
From $460 per night (USD)
VRBO
From $363 per night (USD)
Expedia
Tranquility by AvantStay | Close to Duval St w/ BBQ & Shared Pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Settled in a small community in Old Town, only a short walk to Duval Street, this lovely cottage offers everything you c ...
From $363 per night (USD)
Expedia
From $383 per night (USD)
VRBO
Paradise Place by AvantStay | Key West Old Town Condo w/ Shared Pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Cozy apartment within biking distance to The Historic Seaport, Cuban Coffee Queen, local grocery store Fausto's, and eve ...
From $383 per night (USD)
VRBO
From $211 per night (USD)
Expedia
Key Lime Pie by AvantStay | Ideal Location w/ Splash Pool & Out Door Dining
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
*Please note that this home is available for 28+ night stays only.* Key Lime Pie is a private cottage that perfectly en ...
From $211 per night (USD)
Expedia
From $252 per night (USD)
VRBO
Land Of Love by AvantStay | Pets Allowed! Shared Pool! Great Location!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
*Please note that this home is available for 28+ night stays only.* Your perfect escape to Key West awaits you in the L ...
From $252 per night (USD)
VRBO
From $186 per night (USD)
Expedia
Boat House by AvantStay | Character Cottage | Central Location Month Long Stays
Bedrooms:
2
Bathrooms:
1
Sleeps:
2
*Please note that this home is available for 28+ night stays only.* Step into a tranquil community on a quiet lane and ...
From $186 per night (USD)
Expedia
From $193 per night (USD)
VRBO
Ibis by AvantStay | Close to Duval Street w/ Shared Pool | Month Long Stays Only
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
*Please note that this home is available for 28+ night stays only.* Enjoy your private front porch in this quiet neighb ...
From $193 per night (USD)
VRBO
From $943 per night (USD)
Expedia
Easy Livin' by AvantStay | Key West Home w/ Pool & BBQ | Week Long Stays Only
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
*Please note that this home is available for stays of 7+ days only. Starting January 1, 2026, it will be available for s ...
From $943 per night (USD)
Expedia
From $461 per night (USD)
VRBO
Artist Garden by AvantStay | Great Location w/ Balcony, Shared Pool & BBQ!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
*Please note that this home is available for stays of 7+ days only. Starting January 1, 2026, it will be available for s ...
From $461 per night (USD)
VRBO
From $181 per night (USD)
Expedia
Paradise Palms by AvantStay | Great Location w/ Outdoor Dining, BBQ
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
*Please note that this home is available for 28+ night stays only.* Make your next Florida vacation something special w ...
From $181 per night (USD)
Expedia
From $308 per night (USD)
VRBO
First Breath by AvantStay | Close to Old Town w/ Pool | Month Long Stays Only
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
*Please note that this home is available for 28+ night stays only.* Bring the family to this 3 bed, 2 bath private conc ...
From $308 per night (USD)
VRBO
From $288 per night (USD)
Expedia
Casa de Rosalie by AvantStay | Great Location w/ Pool, BBQ & Outdoor Dining
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
*Please note that this home is available for 28+ night stays only.* Built-in 1889 with original Dade County Pine, histo ...
From $288 per night (USD)
Expedia
From $225 per night (USD)
VRBO
Lazy Gecko by AvantStay | Walk to Duval St in Key West! | Month Long Stays Only
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
*Please note that this home is available for 28+ night stays only.* Grab your bike and head for some fresh seafood at t ...
From $225 per night (USD)
VRBO
Click For Pricing
Expedia
Priced to book! Sleeps 4- Walking Distance to Duval!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Great location in Key West. The Galleon is Walking distance to shopping, bars, dining, trolley, marina, Duval st., Mallo ...
Click For Pricing
Expedia
$\Abaco\ Key West • 2/2 End Unit Waterfront+Dockage$
From $547 per night (USD)
VRBO
\"Abaco\" Key West • 2/2 End Unit Waterfront+Dockage
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Time to relax & fish! Bring your family & friends to this 1350 sqft Waterfront corner home. Boat slips availabl ...
From $547 per night (USD)
VRBO
From $959 per night (USD)
Expedia
Three Condos w/ Entertainment, Private Parking & Beach Nearby - Great for Groups
Bedrooms:
4
Bathrooms:
4
Sleeps:
14
Three Flowers Guesthouse Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ente ...
From $959 per night (USD)
Expedia
From $872 per night (USD)
VRBO
SEAPORT SAILING-Beach-Pool-King-BBQ-Hot Tub-Race Week!
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 $872 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
From $385 per night (USD)
VRBO
Ashe St Serenade: 3BD/3.5BA Luxury Retreat, Private Pool in an Island Oasis.
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Welcome to your dream getaway in the charming Old Town Key West, where the tranquility of island living meets the excite ...
From $385 per night (USD)
VRBO
From $310 per night (USD)
Expedia
**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 $310 per night (USD)
Expedia
From $363 per night (USD)
VRBO
Lavender on White - 3 BD /2 BA House w/ Private Heated Pool and great Kitchen
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Nestled in a prime location, Lavender on White offers the perfect blend of tranquility and accessibility. Situated in th ...
From $363 per night (USD)
VRBO
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Expedia
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 ...
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Expedia
Click For Pricing
VRBO
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
VRBO
From $506 per night (USD)
Expedia
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 $506 per night (USD)
Expedia
From $293 per night (USD)
VRBO
Conch Republic Retreat
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This historic conch home, circa 1890, is your dream vacation spot. The welcoming property has been completely renovated ...
From $293 per night (USD)
VRBO
From $409 per night (USD)
Expedia
Old Town Classic with plenty of charm, porch swing and parking
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Beautiful home with covered porch and swing! Full kitchen, washer/dryer, TV, Internet, A/C, separate patio area with twi ...
From $409 per night (USD)
Expedia
$\A Bird's Eye View\ at The Truman Annex in Key West$
From $396 per night (USD)
VRBO
\"A Bird's Eye View\" at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Stunning, Modern 2 bedroom, 1 bathroom second floor condo in the Truman Annex Shipyard Complex completely renovated. Ful ...
From $396 per night (USD)
VRBO
From $579 per night (USD)
Expedia
4-bedroom vacation home in Key West - steps to Duval St & Florida Keys Beaches
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Escape to the heart of Key West's historic district and immerse yourself in the vibrant island lifestyle. This 4-bedroom ...
From $579 per night (USD)
Expedia
From $202 per night (USD)
VRBO
Fabulous Home with Private Saltwater Pool, Central AC, & High-Speed WiFi
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Keys Please Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $202 per night (USD)
VRBO
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Expedia
Single home with pool, center of Old Town
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Beautiful, newly renovated single home of corner lot in the center of old town. 4 blocks from Duval and 4 blocks from se ...
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Expedia
$The Jasmine House\nJust a 2 minute walk to Duval and restaurants and bars$
From $548 per night (USD)
VRBO
The Jasmine House\nJust a 2 minute walk to Duval and restaurants and bars
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Enjoy your tropical vacation, whether work-free or not, in this Old Town home only a couple of minutes from Duval and Wh ...
From $548 per night (USD)
VRBO
$Waterfront \St. Croix\ Penthouse, Pool, Dock, Pet$
From $1755 per night (USD)
VRBO
Waterfront \"St. Croix\" Penthouse, Pool, Dock, Pet
Bedrooms:
4
Bathrooms:
4
Sleeps:
15
Summary: Bring your family and friends to this 2,400 sqft waterfront penthouse in downtown Key West! 4BR/4BA + loft slee ...
From $1755 per night (USD)
VRBO
From $1649 per night (USD)
VRBO
Downtown Penthouse•Waterviews•Pool, Dock, Parking
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
Summary: Welcome to St. Kitts—a spacious 2,000 sqft waterfront penthouse condo in historic downtown Key West! 4BR/4BA + ...
From $1649 per night (USD)
VRBO
From $405 per night (USD)
Expedia
Sunshine Siesta Cottage~Great Old Town Location, Pool, Private Hot Tub!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
BOOK NOW! Walk down the secluded brick path of the 4-unit compound, past the tropical foliage to Unit B, adjacent to the ...
From $405 per night (USD)
Expedia
From $409 per night (USD)
VRBO
**MARGARET’S MAGIC COMPOUND @ SOLARIS HILL** Old Town Compound & Pool + LAST KEY
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Travelers fro ...
From $409 per night (USD)
VRBO
From $707 per night (USD)
Expedia
Eliza's Secret - Elegant Tropical Oasis with Private Pool & Guest House
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Enjoy all of Key West's exciting activities from the privacy and comfort of your own two-story, historic home in Old Tow ...
From $707 per night (USD)
Expedia
From $147 per night (USD)
VRBO
Campbell Cottage in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Location...Location...Location! Campbell Cottage is perfectly located to walk to almost everything Key West has to offer ...
From $147 per night (USD)
VRBO
From $416 per night (USD)
Expedia
The Courtyard in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Vacation ever so comfortably in this well-designed one bedroom, one-full-bath courtyard unit at Campbell Court. You can ...
From $416 per night (USD)
Expedia
From $185 per night (USD)
VRBO
Anchor's Away in Key West
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Need a refresher course in relaxation? Find it behind the brass seahorse knocker on the front door of this three-bedroom ...
From $185 per night (USD)
VRBO
From $222 per night (USD)
Expedia
La Hacienda in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Looking as though it were plucked from the glossy pages of Spanish literature, La Hacienda is one of Key West's most dis ...
From $222 per night (USD)
Expedia
From $395 per night (USD)
VRBO
Campbell Suite in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Let your rendezvous with paradise begin at the Campbell Courtyard compound in the heart of Old Town Key West. Campbell S ...
From $395 per night (USD)
VRBO
From $92 per night (USD)
Expedia
Bay's Hideaway in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Just the mere idea of planning a vacation puts a smile on most faces. If your vacation includes a stay in the Conch Repu ...
From $92 per night (USD)
Expedia
From $590 per night (USD)
VRBO
Quilted Giraffe in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Your space. Your vacation lifestyle. The Quilted Giraffe provides both. This two-bedroom, two full bath home welcomes yo ...
From $590 per night (USD)
VRBO
From $235 per night (USD)
Expedia
MONTHLY - 1 block from the Seaport and 2 blocks from Duval Street
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This beautifully decorated property has soaring ceilings with a lovely outdoor dining & bbq area and is walking distance ...
From $235 per night (USD)
Expedia
From $155 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 $155 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 $181 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 $181 per night (USD)
VRBO
From $755 per night (USD)
Expedia
**TRUMAN’S TROVE @ THE ANNEX** Private Home & Pool + LAST KEY SERVICES…
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Hunting for t ...
From $755 per night (USD)
Expedia
From $986 per night (USD)
VRBO
Kemp House in Key West
Bedrooms:
3
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 $986 per night (USD)
VRBO
From $643 per night (USD)
Expedia
NEW MONTHLY LISTING! Seacret Paradise: Desirable Oasis in the Heart of Old Town
Bedrooms:
3
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 $643 per night (USD)
Expedia
From $2808 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 $2808 per night (USD)
VRBO
From $1139 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 $1139 per night (USD)
Expedia
From $333 per night (USD)
VRBO
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 $333 per night (USD)
VRBO
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Expedia
Experience The Galleon – A 5-Star Timeshare Resort in Charming Old Key West, Fl
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 ...
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Expedia
From $374 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 $374 per night (USD)
VRBO
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Expedia
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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Expedia
From $180 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 $180 per night (USD)
VRBO
From $1033 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 $1033 per night (USD)
Expedia
$ALL INCLUSIVE! Snorkel/Sail/Spear Fish/Fishing/Fun\n$
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VRBO
ALL INCLUSIVE! Snorkel/Sail/Spear Fish/Fishing/Fun\n
Bedrooms:
1
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 ...
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VRBO
$Amazing Location 3bed/2bath & Swim Spa\n\n$
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Expedia
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 ...
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Expedia
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VRBO
OLD TOWN LUXURY HOME - completely remodeled, updated, steps to Duval Street.
Bedrooms:
3
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 ...
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VRBO
From $199 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 $199 per night (USD)
Expedia
From $402 per night (USD)
VRBO
Snowbird-friendly oasis with private heated pool, lush yard, & ample parking
Bedrooms:
3
Bathrooms:
3
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)
VRBO
From $373 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 $373 per night (USD)
Expedia
From $296 per night (USD)
VRBO
LA CASITA EN CIMA~ Enjoy Key West in this lovely gem with a heated pool.
Bedrooms:
2
Bathrooms:
2
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 $296 per night (USD)
VRBO
From $308 per night (USD)
Expedia
**THE WICKED TUNA @ THE SEAPORT** Private Home & Pool + LAST KEY SERVICES…
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Get ready to ...
From $308 per night (USD)
Expedia
From $349 per night (USD)
VRBO
**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 60 days prior to your arrival! CASA AVILA co ...
From $349 per night (USD)
VRBO
From $416 per night (USD)
Expedia
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 $416 per night (USD)
Expedia
From $509 per night (USD)
VRBO
THREE ARCHES IN PARADISE~ A Mediterranean marvel in a walkable location!
Bedrooms:
3
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 $509 per night (USD)
VRBO
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Expedia
Hyatt resort 2-bdr 2 bath Duvale St in Key West with kitchen washer/dryer pool
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Discover the beauty of Key West from this 2-bedroom 2 bath resort. The spacious bedrooms feature a king and queen bed, p ...
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Expedia
From $594 per night (USD)
VRBO
**SPIRIT OF KEY WEST @ OLD TOWN** Exquisite Home & Pool + LAST KEY SERVICES…
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! SPIRIT OF KEY ...
From $594 per night (USD)
VRBO
From $379 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 $379 per night (USD)
Expedia
From $238 per night (USD)
VRBO
THE FLAGLER ROOM @ The Inn on Fleming ~ 1st Floor King Room w/ Shared Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
CAPTIVATING CLASSIC REVIVAL CHARM... Built in 1894, the delightful Inn on Fleming was once the residence of Board of Edu ...
From $238 per night (USD)
VRBO
From $257 per night (USD)
Expedia
THE WHITEHEAD ROOM @ The Inn on Fleming ~ 2nd Floor Queen w/ Shared Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
CAPTIVATING CLASSIC REVIVAL CHARM... Built in 1894, the delightful Inn on Fleming was once the residence of Board of Edu ...
From $257 per night (USD)
Expedia
Click For Pricing
VRBO
Waterfront Resort, Songwriter’s Fest, Old Town, Sleeps 6, Swimming Pool, Hot Tub
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Have I mentioned that this listing is for the Songwriter’s Festival in sunny Key West, FL? You will be staying at the Hy ...
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VRBO
From $250 per night (USD)
Expedia
THE MALLORY SUITE @ the Inn on Fleming ~ 1st Floor King Suite w/ Shared Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
CAPTIVATING CLASSIC REVIVAL CHARM... Built in 1894, the delightful Inn on Fleming was once the residence of Board of Edu ...
From $250 per night (USD)
Expedia
Click For Pricing
VRBO
Waterfront Resort, Songwriter’s Fest, Old Town, Sleeps 4, Swimming Pool, Hot Tub
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Have I mentioned that this listing is for the Songwriter’s Festival in sunny Key West, FL? You will be staying at the Hy ...
Click For Pricing
VRBO
From $270 per night (USD)
Expedia
THE HEMINGWAY SUITE @ the Inn on Fleming ~ 2nd Floor King w/ Shared Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
CAPTIVATING CLASSIC REVIVAL CHARM... Built in 1894, the delightful Inn on Fleming was once the residence of Board of Edu ...
From $270 per night (USD)
Expedia
From $296 per night (USD)
VRBO
THE CORNISH SUITE @ Inn on Fleming ~ 3rd Floor 2 Bedroom w/Shared Pool!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
CAPTIVATING CLASSIC REVIVAL CHARM... Built in 1894, the delightful Inn on Fleming was once the residence of Board of Edu ...
From $296 per night (USD)
VRBO
From $237 per night (USD)
Expedia
THE SIMONTON ROOM @ The Inn on Fleming ~ 1st Floor King Room w/ Shared Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
CAPTIVATING CLASSIC REVIVAL CHARM... Built in 1894, the delightful Inn on Fleming was once the residence of Board of Edu ...
From $237 per night (USD)
Expedia
$Villa La Isla- Luxury Vacation Rental 1\/2 block from Duval$
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VRBO
Villa La Isla- Luxury Vacation Rental 1\/2 block from Duval
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Villa la Isla is a brand new, professionally designed luxury residence located in the heart of Old Town Key West. Walkin ...
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VRBO
From $706 per night (USD)
VRBO
Dos Casas - 2 House Compound in Old Town Key West - A Monthly Rental
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Dos Casas can be the answer to your fabulous Old Town Key West vacation. We've been renting to discerning travelers for ...
From $706 per night (USD)
VRBO
From $634 per night (USD)
VRBO
**GRENN TURTLE COTTAGE @ THE ANNEX** Stunning Private Home + LAST KEY SERVICES…
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! GREEN TURTLE ...
From $634 per night (USD)
VRBO
From $330 per night (USD)
Expedia
Welcome Matt's - Truman @ Duval | Ideal One-Bedroom Retreat
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Truman @ Duval Unit B | Ideal One-Bedroom Retreat for Couples Escape to a charming one-bedroom apartment in the heart o ...
From $330 per night (USD)
Expedia

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