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 $1510 per night (USD)
VRBO
CASA MARGARITA Steps to the Historic Seaport
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Casa Margarita is the ideal for outdoor dining, relaxing, and entertaining, with its spacious covered patio, ample seati ...
From $1510 per night (USD)
VRBO
From $823 per night (USD)
Expedia
Find your zen at HIDDEN TREASURE
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Hidden from sight, among a colony of freestanding conch cottages and surrounded by lush tropical landscaping, you will f ...
From $823 per night (USD)
Expedia
From $772 per night (USD)
VRBO
Get your ISLAND STLYE on!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This quaint property offers resort-style accommodations at an affordable price! Nestled among a colony of freestanding C ...
From $772 per night (USD)
VRBO
From $651 per night (USD)
Expedia
HIDDEN OASIS 3 blocks from Duval
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Tucked among a colony of freestanding Conch style cottages and lush tropical landscaping sits the newly renovated Hidden ...
From $651 per night (USD)
Expedia
From $3646 per night (USD)
VRBO
Key West, Galleon Resort, Marina, In Town, Pool, Hot Tub
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Enjoy the glamour of this stylish, upscale place. Overlooking the shimmering span of Gulf of Mexico in historic Old Tow ...
From $3646 per night (USD)
VRBO
From $944 per night (USD)
VRBO
𝐅𝐢𝐧𝐝𝐢𝐧𝐠𝐌𝐞𝐢𝐥𝐢 Waterfront Sunset Harbor Resort, DUVAL STREET+Amenities
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to 𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢🌴 Experience Paradise at Hyatt Vacation Club at Sunset Harbor! Additional $500-$1 ...
From $944 per night (USD)
VRBO
From $396 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 $396 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 $1044 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 $1044 per night (USD)
Expedia
From $253 per night (USD)
VRBO
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 $253 per night (USD)
VRBO
From $2118 per night (USD)
Expedia
Luxury 4BDR/4BA Penthouse | 4 Bed, 4 Bath
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Welcome to the Luxury Harbor House Suites! We proudly offer you a newly renovated 2,400SF, 4BDR/4BA Penthouse in the Cit ...
From $2118 per night (USD)
Expedia
From $411 per night (USD)
VRBO
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 $411 per night (USD)
VRBO
From $544 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 $544 per night (USD)
Expedia
Click For Pricing
VRBO
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
VRBO
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 $254 per night (USD)
VRBO
Old Town Elegance with Island Breezes and Poolside Bliss
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Charming Pool Cottage in the Heart of Old Town Key West Perfectly situated in historic Old Town Key West, this quaint a ...
From $254 per night (USD)
VRBO
From $705 per night (USD)
Expedia
FERNWOOD ~ Dreamy, Lush Estate with Incredible Outdoor Space with Pool & Spa!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
THERE'S NO PLACE LIKE YOUR ISLAND HOME... Located in the highly sought-after area of The Meadows and beneath peaceful sw ...
From $705 per night (USD)
Expedia
From $3350 per night (USD)
VRBO
Old Town Caribbean Estate Key West - Great for Groups - Private Pool - Sleeps 21
Bedrooms:
7
Bathrooms:
10
Sleeps:
21
The Old Town Caribbean Estate is a masterful combination of a classic Key West Victorian home with an exotic Caribbean-s ...
From $3350 per night (USD)
VRBO
From $2496 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 $2496 per night (USD)
Expedia
From $282 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 $282 per night (USD)
VRBO
From $683 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 $683 per night (USD)
VRBO
From $350 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 $350 per night (USD)
VRBO
From $468 per night (USD)
Expedia
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 $468 per night (USD)
Expedia
From $1751 per night (USD)
VRBO
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 $1751 per night (USD)
VRBO
From $534 per night (USD)
Expedia
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)
Expedia
Click For Pricing
VRBO
Hyatt Sunset Harbor on the Water-Luxury Key West 2 Bedroom Condo Dec 21-Dec 28.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This is the luxury boutique resort you and your family and friends deserve. A few steps to famous Mallory Square and all ...
Click For Pricing
VRBO
From $310 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 $310 per night (USD)
Expedia
From $238 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 $238 per night (USD)
VRBO
From $208 per night (USD)
Expedia
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 $208 per night (USD)
Expedia
From $849 per night (USD)
VRBO
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 ...
From $849 per night (USD)
VRBO
From $516 per night (USD)
Expedia
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 $516 per night (USD)
Expedia
From $650 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 $650 per night (USD)
VRBO
From $267 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 $267 per night (USD)
Expedia
From $405 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 $405 per night (USD)
VRBO
From $930 per night (USD)
Expedia
**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 $930 per night (USD)
Expedia
From $510 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 $510 per night (USD)
VRBO
From $4150 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 $4150 per night (USD)
VRBO
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 $2921 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 $2921 per night (USD)
VRBO
From $1227 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 $1227 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
From $679 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 $679 per night (USD)
VRBO
From $233 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 $233 per night (USD)
VRBO
From $400 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 $400 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
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 $293 per night (USD)
Expedia
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 $293 per night (USD)
Expedia
From $882 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 $882 per night (USD)
VRBO
From $304 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 $304 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 $619 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 $619 per night (USD)
Expedia
$\Abaco\ Key West • 2/2 End Unit Waterfront+Dockage$
From $837 per night (USD)
VRBO
\"Abaco\" Key West • 2/2 End Unit Waterfront+Dockage
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Summary: Time to relax & fish! Bring your family & friends to this 1350 sqft Waterfront corner home. Boat slips availabl ...
From $837 per night (USD)
VRBO
From $511 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 $511 per night (USD)
Expedia
$\A Bird's Eye View\ at The Truman Annex in Key West$
From $451 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 $451 per night (USD)
VRBO
From $218 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 $218 per night (USD)
Expedia
From $857 per night (USD)
VRBO
Old Town Key West Luxury 4BR – Private Pool by Historic Seaport - Monthly Rental
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 $857 per night (USD)
VRBO
From $984 per night (USD)
Expedia
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)
Expedia
From $449 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 $449 per night (USD)
VRBO
From $366 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 $366 per night (USD)
Expedia
From $669 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 $669 per night (USD)
VRBO
Click For Pricing
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 ...
Click For Pricing
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 $426 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 $426 per night (USD)
Expedia
From $746 per night (USD)
VRBO
**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 $746 per night (USD)
VRBO
From $167 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 $167 per night (USD)
Expedia
From $1164 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 $1164 per night (USD)
VRBO
$Waterfront \St. Croix\ Penthouse, Pool, Dock, Pet$
From $1716 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 $1716 per night (USD)
VRBO
From $1758 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 $1758 per night (USD)
VRBO
From $334 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 $334 per night (USD)
Expedia
From $948 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 $948 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 $450 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 $450 per night (USD)
VRBO
From $217 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 $217 per night (USD)
Expedia
From $257 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 $257 per night (USD)
VRBO
From $561 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 $561 per night (USD)
Expedia
From $163 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 $163 per night (USD)
VRBO
From $814 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 $814 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 $585 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 $585 per night (USD)
VRBO
From $195 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 $195 per night (USD)
VRBO
From $231 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 $231 per night (USD)
Expedia
From $197 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 $197 per night (USD)
VRBO
From $983 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 $983 per night (USD)
Expedia
From $502 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 $502 per night (USD)
VRBO
From $242 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 $242 per night (USD)
Expedia
From $317 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 $317 per night (USD)
VRBO
From $543 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 $543 per night (USD)
Expedia
From $292 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 $292 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
From $512 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 $512 per night (USD)
VRBO
From $590 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 $590 per night (USD)
Expedia
From $446 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 $446 per night (USD)
VRBO
From $606 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 $606 per night (USD)
VRBO
From $413 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 $413 per night (USD)
VRBO
From $837 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 $837 per night (USD)
Expedia
From $557 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 $557 per night (USD)
VRBO
From $415 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 $415 per night (USD)
Expedia
From $1217 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 $1217 per night (USD)
VRBO
From $660 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 $660 per night (USD)
Expedia

Search Your Destination Now!

Fleming Key Rentals

Rental Rates ($USD weekly)

Guests

Check Rates & Availability:

Results: 782 Rentals