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 $641 per night (USD)
VRBO
Deluxe Key West Ocean Front Condo Week - April 22 - 29, 2025
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Deluxe Ocean Front Condo in Key West Florida with a spectacular 3rd Floor balcony view of the Marina and Ocean. One Full ...
From $641 per night (USD)
VRBO
From $2125 per night (USD)
Expedia
Harbor House Suite A | 4 Bed, 4 Bath
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
Welcome to Luxury Harbor House Suites, an exceptional NIGHTLY vacation rental property located in the heart of Key West' ...
From $2125 per night (USD)
Expedia
From $261 per night (USD)
VRBO
UPTOWN FUNK ~ Newly Renovated 3 BR Townhome in Old Town with Parking!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
IMMACULATE UPSCALE DELIGHT… Embrace the island vibes and immerse yourself in the Key West spirit in this enchanting 3 st ...
From $261 per night (USD)
VRBO
From $508 per night (USD)
VRBO
Ann Street Tranquility: A cozy and peaceful cottage
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This charming one bedroom cottage is the perfect hideaway. The quiet compound is located just one block from Duval Stre ...
From $508 per night (USD)
VRBO
From $270 per night (USD)
VRBO
Old Town cottage
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The newly remodeled home is located in the middle of Old Town down a private lane just a block from Duval Street. One of ...
From $270 per night (USD)
VRBO
From $382 per night (USD)
Expedia
Conch Cottage Retreat in the heart of Old Town Key West
Bedrooms:
2
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:
3
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
From $2324 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 $2324 per night (USD)
Expedia
From $428 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 $428 per night (USD)
VRBO
Click For Pricing
Expedia
The Sandy Beach House in Historic Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Spend time in Key West and live like a local in a true Conch Home! The Sandy Beach Cottage, a fully-renovated first floo ...
Click For Pricing
Expedia
From $158 per night (USD)
VRBO
Garden of Eden Cottage | 1 Bed, 1.5 Bath
Bedrooms:
1
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 $158 per night (USD)
VRBO
From $380 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 $380 per night (USD)
Expedia
From $413 per night (USD)
VRBO
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 $413 per night (USD)
VRBO
From $348 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 $348 per night (USD)
Expedia
From $321 per night (USD)
VRBO
Classic King & Private Balcony - Curry Mansion Inn
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...
From $321 per night (USD)
VRBO
From $1738 per night (USD)
Expedia
Key West Suites Hotel #201 on Duval
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Key West Suites Hotel #201 Welcome to your charming private studio apartment right on Duval street! Built in 1919, it u ...
From $1738 per night (USD)
Expedia
From $534 per night (USD)
VRBO
Old Town Bali Hideaway For 2, Just Steps From Duval
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Perfect for two, this Bali style, studio cottage has it all... COMFORT and LOCATION. Located on an Ann Street compound j ...
From $534 per night (USD)
VRBO
From $210 per night (USD)
Expedia
Hidden Treasure in Old Town: 3BR Home with Pool in Peaceful Gated Enclave
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Your Key West Hideaway home is located in the heart of Old Town. Key West landmarks, attractions, Duval St, restaurants, ...
From $210 per night (USD)
Expedia
From $217 per night (USD)
VRBO
Private Home in Heart of Old Town (Shared Pool!)
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Come escape to paradise in this newly updated and available home steps from Duval! Equipped with all the amenities for a ...
From $217 per night (USD)
VRBO
Click For Pricing
Expedia
SEAPORT SKYLINE-Beach-Pool-King-BBQ-Hot Tub-Rooftop views!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
OCEANFRONT CASUAL LUXURY CONDO RENTAL WITH BREATHTAKING VIEWS OF KEY WEST HARBOR AND THE GULF OF MEXICO. PENTHOUSE COND ...
Click For Pricing
Expedia
From $234 per night (USD)
VRBO
Caroline On My Mind-New Listing-Light, Bright and Airy!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This beautifully restored, remodeled second-floor 1933 Key West home on Caroline Street offers a unique and inviting exp ...
From $234 per night (USD)
VRBO
From $674 per night (USD)
VRBO
Heart of Key West - 2BR Waterfront at the Galleon Resort
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Located in the heart of Old Town Key West. This resort overlooks the Gulf of Mexico with a private marina, private beach ...
From $674 per night (USD)
VRBO
From $237 per night (USD)
VRBO
WINDSONG DELIGHT - Cute house on Windsor Ln
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This two story townhome has both location and amenities for a wonderful month long visit to Key West. Secluded at the r ...
From $237 per night (USD)
VRBO
From $336 per night (USD)
VRBO
little bodega in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Very nice 1 br/bath house on Solaris Hill centered 2 blks off Duvall St. in Old Town Key West. Enjoy bustling Duvall wi ...
From $336 per night (USD)
VRBO
From $535 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 $535 per night (USD)
VRBO
From $416 per night (USD)
Expedia
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 $416 per night (USD)
Expedia
From $619 per night (USD)
VRBO
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)
VRBO
From $2560 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 $2560 per night (USD)
VRBO
From $1111 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 $1111 per night (USD)
VRBO
From $271 per night (USD)
Expedia
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 $271 per night (USD)
Expedia
$Two-bedroom townhouse overlooking the harbor.\n \nONLY AVAILABLE Nov. 9 - Nov 16$
From $900 per night (USD)
VRBO
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)
VRBO
From $394 per night (USD)
Expedia
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)
Expedia
Click For Pricing
VRBO
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 ...
Click For Pricing
VRBO
From $3588 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 $3588 per night (USD)
VRBO
From $700 per night (USD)
VRBO
**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 $700 per night (USD)
VRBO
From $261 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 $261 per night (USD)
VRBO
From $391 per night (USD)
VRBO
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 $391 per night (USD)
VRBO
From $135 per night (USD)
Expedia
Prime Old Town Location w/ Pool, Walk to Duval Steet | Blue Heron by AvantStay
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.* Located at 906-2 Tru ...
From $135 per night (USD)
Expedia
From $984 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 $984 per night (USD)
VRBO
From $415 per night (USD)
Expedia
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 $415 per night (USD)
Expedia
From $391 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 $391 per night (USD)
VRBO
From $363 per night (USD)
Expedia
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)
Expedia
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 $506 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 $506 per night (USD)
VRBO
$\Abaco\ Key West • 2/2 End Unit Waterfront+Dockage$
From $646 per night (USD)
Expedia
\"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 $646 per night (USD)
Expedia
From $976 per night (USD)
VRBO
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 $976 per night (USD)
VRBO
From $255 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 $255 per night (USD)
Expedia
From $751 per night (USD)
VRBO
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 $751 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 $426 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 $426 per night (USD)
VRBO
From $345 per night (USD)
Expedia
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 $345 per night (USD)
Expedia
Click For Pricing
VRBO
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 ...
Click For Pricing
VRBO
$The Jasmine House\nJust a 2 minute walk to Duval and restaurants and bars$
From $578 per night (USD)
Expedia
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 $578 per night (USD)
Expedia
From $468 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 $468 per night (USD)
VRBO
From $378 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 $378 per night (USD)
Expedia
From $358 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 $358 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 $256 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 $256 per night (USD)
VRBO
From $235 per night (USD)
Expedia
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 $235 per night (USD)
Expedia
From $169 per night (USD)
VRBO
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 $169 per night (USD)
VRBO
From $200 per night (USD)
Expedia
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 $200 per night (USD)
Expedia
From $854 per night (USD)
VRBO
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 $854 per night (USD)
VRBO
From $419 per night (USD)
Expedia
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 $419 per night (USD)
Expedia
From $217 per night (USD)
VRBO
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 $217 per night (USD)
VRBO
From $363 per night (USD)
Expedia
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 $363 per night (USD)
Expedia
From $319 per night (USD)
VRBO
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 $319 per night (USD)
VRBO
From $230 per night (USD)
Expedia
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 $230 per night (USD)
Expedia
Click For Pricing
VRBO
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
VRBO
$Waterfront \St. Croix\ Penthouse, Pool, Dock, Pet$
From $1619 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 $1619 per night (USD)
VRBO
From $1420 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 $1420 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 $439 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 $439 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 $269 per night (USD)
VRBO
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 $269 per night (USD)
VRBO
From $248 per night (USD)
Expedia
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 $248 per night (USD)
Expedia
From $275 per night (USD)
VRBO
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 $275 per night (USD)
VRBO
From $308 per night (USD)
Expedia
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 $308 per night (USD)
Expedia
From $88 per night (USD)
VRBO
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 $88 per night (USD)
VRBO
From $574 per night (USD)
Expedia
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 $574 per night (USD)
Expedia
From $235 per night (USD)
VRBO
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)
VRBO
From $361 per night (USD)
Expedia
Hollinsed House Studio - Great Location!!
Bedrooms:
1
Bathrooms:
2
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 $361 per night (USD)
Expedia
From $631 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 $631 per night (USD)
VRBO
From $187 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 $187 per night (USD)
Expedia
From $1030 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 $1030 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:
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 ...
Click For Pricing
Expedia
Click For Pricing
VRBO
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 ...
Click For Pricing
VRBO
From $507 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 $507 per night (USD)
VRBO
From $236 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 $236 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 $772 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 $772 per night (USD)
VRBO
From $730 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 $730 per night (USD)
Expedia
From $1009 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 $1009 per night (USD)
VRBO
From $324 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 $324 per night (USD)
Expedia
Click For Pricing
VRBO
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 ...
Click For Pricing
VRBO
From $358 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 $358 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 $1359 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 $1359 per night (USD)
VRBO

Search Your Destination Now!

Fleming Key Rentals

Rental Rates ($USD weekly)

Guests

Check Rates & Availability:

Results: 780 Rentals