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 $584 per night (USD)
VRBO
THE WRITER'S COTTAGE ~ Renovated 2 BR/2 Ba Home w/ Parking!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
NOSTALGIC AND INSPIRATIONAL HAVEN... History permeates and echoes through the classic Dade Pine details of this lovingly ...
From $584 per night (USD)
VRBO
From $1245 per night (USD)
Expedia
Luxe Designer Oasis + Guest House steps off Duval
Bedrooms:
6
Bathrooms:
6
Sleeps:
12
Discover unparalleled luxury at Autograph House, an exclusive private oasis just one block from the center of Key West. ...
From $1245 per night (USD)
Expedia
From $383 per night (USD)
VRBO
Southernmost Seclusion, central to Old Town hot spots. Pool, balconies, parking
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
- Two private outdoor spaces – greet the sunrise on the covered balcony, toast the sunset on a second, tree‑top perch. ...
From $383 per night (USD)
VRBO
From $333 per night (USD)
Expedia
10% Off Adv Rate-Upgraded Cottage-Steps to Famous Duval Street &Historic Seaport
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Offering an additional 10% off current advertised rate on all bookings. Located in the historic district of Key West thi ...
From $333 per night (USD)
Expedia
From $642 per night (USD)
VRBO
AZURE KEY WEST - Stunning New Home with Heated Pool - 4 Bedrooms Available
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Unwind in Key West at this lovely villa. Completely renovated top-to-bottom and completed in 2025, with 4 bedrooms inclu ...
From $642 per night (USD)
VRBO
From $784 per night (USD)
Expedia
NEW LISTING 4 ENSUITE BEDROOMS , OLD TOWN, PARKING, AC, POOL, BLOCK FROM DUVAL
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Discover Key West at its finest from your private luxury retreat just a block and a half off Duval Street. Newly renova ...
From $784 per night (USD)
Expedia
From $830 per night (USD)
VRBO
**BOHEMIA @ OLD TOWN** Fully Renovated 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! Welcome to BO ...
From $830 per night (USD)
VRBO
From $569 per night (USD)
Expedia
Blanco Luxury Villa | 4 bedrooms & 4 baths in the heart of Old Town
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Welcome to Blanco Luxury Villa, your dream getaway in the heart of Old Town Key West. Located near the waterfront in Ol ...
From $569 per night (USD)
Expedia
From $428 per night (USD)
VRBO
** FLIGHT OF THE FLAMINGO @ OLD TOWN ** Home & Private Pool + LAST KEY SERVICES.
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! After landing ...
From $428 per night (USD)
VRBO
Click For Pricing
Expedia
Bahari House | Key West Home w/ Balcony, & Steps to Ocean & Bars
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Top reasons to book: - Downtown Location - 3 Minute Walk to the beach - Grocery Store Nearby - Close to Bars & Rest ...
Click For Pricing
Expedia
From $309 per night (USD)
VRBO
Hyatt Vacation Club in Key West- Studio
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Key West at its best. Hyatt Sunset Harbor resort directly overlooking the gulf. Just 1 block to Mallory Square and the w ...
From $309 per night (USD)
VRBO
From $845 per night (USD)
VRBO
Historic Key West Hideaway – Walk to the Seaport! Outdoor Pool, Free Breakfast!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Enjoy vibrant Key West: steps to Duval Street's nightlife, historic sites, and serene beaches. Perfect for culture and s ...
From $845 per night (USD)
VRBO
From $4313 per night (USD)
VRBO
Luxe two 4BDR/4BA Suites
Bedrooms:
8
Bathrooms:
8
Sleeps:
20
Welcome to Old Harbor House, an exquisite vacation rental combining two spacious 4-bedroom suites in the heart of Key We ...
From $4313 per night (USD)
VRBO
From $1432 per night (USD)
Expedia
Passover Cottage | Private Pool & Ideal Key West Location
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Passover Cottage | Private Pool & Ideal Key West Location Passover Cottage is your ultimate retreat in the heart of Key ...
From $1432 per night (USD)
Expedia
From $1151 per night (USD)
VRBO
Newport Getaway! Pool, Spa, Onsite Dining, & Easy Access to Attractions!
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 $1151 per night (USD)
VRBO
From $1518 per night (USD)
VRBO
Pet-Friendly Stay, Pool, Spa, Fitness Center! Historic Sights Nearby
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 $1518 per night (USD)
VRBO
From $651 per night (USD)
VRBO
Lux Waterfront Suite w/ Pool, Spa, & Walk to Newport Marina & Attractions
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $651 per night (USD)
VRBO
From $648 per night (USD)
VRBO
Pet-Friendly Waterfront Escape w/ Pool, Near Cliff Walk & Newport Fun
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $648 per night (USD)
VRBO
From $1325 per night (USD)
VRBO
Spacious Oceanfront Stay! Spa, Fitness, & Steps to the Beach!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $1325 per night (USD)
VRBO
From $645 per night (USD)
VRBO
Chic Stay Near Newport Harbor & Cliff Walk! Pool, Spa, Fitness Center!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $645 per night (USD)
VRBO
From $645 per night (USD)
VRBO
Spacious Lanai Suite! Pool, Marina Access, Walk to Dining Spots & Museums
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $645 per night (USD)
VRBO
From $1325 per night (USD)
VRBO
Stylish Suite w/ Oceanfront View, Pool, Spa, & Steps to Historic Newport
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $1325 per night (USD)
VRBO
From $955 per night (USD)
VRBO
Pet-Friendly Ocean View Stay! Pool, Spa, Historic Sights Nearby!
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 $955 per night (USD)
VRBO
From $1518 per night (USD)
VRBO
Lux Gulf View Suite! Pool, Marina Access, Walk to Dining Spots & Museums!
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 $1518 per night (USD)
VRBO
From $919 per night (USD)
VRBO
Charming 2BR Stay, Ella’s | Garden Retreat w/ Pool Access and Free Breakfast!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Discover the heart of Old Town Key West! This hotel is located steps from Duval Street and Hemingway's home. Stroll to S ...
From $919 per night (USD)
VRBO
From $1305 per night (USD)
Expedia
~CONCH COTTAGES~ Enjoy your next island vacation with friends right here!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
THE PROPERTY: Enjoy your stay with us at the quaint ‘Conch Cottages’ property, which includes 3 separate rentable units: ...
From $1305 per night (USD)
Expedia
From $329 per night (USD)
VRBO
~ROBINSON CRUSOE COTTAGE~ Delight in island vibes in this home with a pool.
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
THE PROPERTY: Enjoy your stay with us at Robinson Crusoe Cottage, part of the quaint Conch Cottages property, which incl ...
From $329 per night (USD)
VRBO
From $508 per night (USD)
Expedia
**BARBUDA SUITE @ SEAPORT INN** Guest Suite w/ Pool Access + LAST KEY SERVICES..
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Looking for a ...
From $508 per night (USD)
Expedia
From $194 per night (USD)
VRBO
**MATECUMBE SUITE @ SEAPORT INN** Guest Suite w/ Pool Access + LAST KEY SERVICES
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! If you’d like ...
From $194 per night (USD)
VRBO
From $239 per night (USD)
Expedia
**ANTIGUA SUITE @ SEAPORT INN** Guest Suite w/ Pool Access + LAST KEY SERVICES..
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! If the allure ...
From $239 per night (USD)
Expedia
From $556 per night (USD)
VRBO
Cozy home with private pool, BBQ, central AC, enclosed yard
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Key to Paradise Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $556 per night (USD)
VRBO
From $1592 per night (USD)
Expedia
SEVENTH HEAVEN~Waterfront 5 BR, 4 Ba Townhome with Pool, Elevator & Dockage!
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
OLD KEY WEST ELEGANCE WITH AN ELEVATOR, PRIVATE POOL AND BOAT DOCKAGE... Indulge in island chic as you approach this lux ...
From $1592 per night (USD)
Expedia
Click For Pricing
VRBO
Large Penthouse suite in the charming Bayan Resort in beautiful Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The Banyan Resort Key West, Florida In the heart of historic Old Town Key West, The Banyan Resort boasts a storied hist ...
Click For Pricing
VRBO
From $303 per night (USD)
Expedia
**KOKOMO SUITE @ SEAPORT INN** Historic Charm & Community Pool + LAST KEY SERVIC
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! You can skip ...
From $303 per night (USD)
Expedia
From $325 per night (USD)
VRBO
ISLAND IN THE SUN ~ Newly Renovated 3 BR Townhome in Old Town with Parking!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
EXCEPTIONAL SANCTUARY IN OLD TOWN... Lose yourself in this light and airy upscale retreat in a prime location, just 1.5 ...
From $325 per night (USD)
VRBO
From $668 per night (USD)
VRBO
Partial Harbor View King Room at Marker Key West Harbor Resort – Pet-friendly
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This listing is for a room within a hotel. ✦ Your room is 400 sq. ft, equipped with complimentary toiletries, high defi ...
From $668 per night (USD)
VRBO
From $777 per night (USD)
VRBO
Harbor View King w/ Balcony at Marker Harbor Resort – Your Waterfront Oasis
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This listing is for a room within a hotel. ✦ Your room is 400 sq. ft, equipped with complimentary toiletries, high defi ...
From $777 per night (USD)
VRBO
From $511 per night (USD)
VRBO
Marker Key West Harbor, Classic Queen Room, 3 Swimming Pools & Pet-friendly
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This listing is for a room within a hotel. ✦ Your room is 400 sq. ft, equipped with complimentary toiletries, high defi ...
From $511 per night (USD)
VRBO
From $777 per night (USD)
VRBO
Relax by the Water with Stunning Pools and Access to Watersports Activities
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This listing is for a room within a hotel. ✦ Your room is 400 sq. ft, equipped with complimentary toiletries, high defi ...
From $777 per night (USD)
VRBO
From $668 per night (USD)
VRBO
Waterfront Living with Private Pools, Calm Waters, and Poolside Dining
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This listing is for a room within a hotel. ✦ Your room is 400 sq. ft, equipped with complimentary toiletries, high defi ...
From $668 per night (USD)
VRBO
From $1095 per night (USD)
VRBO
Marker Key West Harbor, 2 Classic 2 Queens, 3 Onsite Pools & Pets are Welcome
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms. ✦ Each room is ...
From $1095 per night (USD)
VRBO
From $531 per night (USD)
VRBO
Classic 2 Queen Room at Marker Key West Harbor - Minutes from the Ocean
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This listing is for a room within a hotel. ✦ Your room is 400 sq. ft, equipped with complimentary toiletries, high defi ...
From $531 per night (USD)
VRBO
From $523 per night (USD)
VRBO
Pool & Garden View 2 Queen Room at Marker Key West Harbor - Pet-friendly!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This listing is for a room within a hotel. ✦ Your room is 400 sq. ft, equipped with complimentary toiletries, high defi ...
From $523 per night (USD)
VRBO
From $510 per night (USD)
VRBO
Perfect Key West Hideaway with 3 Pools, Poolside Dining, and a Peaceful Setting
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This listing is for a room within a hotel. ✦ Your room is 400 sq. ft, equipped with complimentary toiletries, high defi ...
From $510 per night (USD)
VRBO
From $581 per night (USD)
VRBO
Marker Key West Harbor, Pool & Garden View Room, 3 Outdoor Swimming Pools
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This listing is for a room within a hotel. ✦ Your room is 400 sq. ft, equipped with complimentary toiletries, high defi ...
From $581 per night (USD)
VRBO
From $531 per night (USD)
VRBO
Island Hideaway with Three Pools and Easy Access to Watersports Rentals
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This listing is for a room within a hotel. ✦ Your room is 400 sq. ft, equipped with complimentary toiletries, high defi ...
From $531 per night (USD)
VRBO
From $1617 per night (USD)
VRBO
3 Classic 2 Queen Rooms at Marker Key West Harbor - Pet-friendly Property
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
This listing is for 3 separate rooms within a hotel. The price shown in the listing covers all 3 rooms. ✦ Each room is ...
From $1617 per night (USD)
VRBO
From $502 per night (USD)
VRBO
Tranquil Island Getaway with Three Pools, Resort Dining, and Watersports
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This listing is for a room within a hotel. ✦ Your room is 400 sq. ft, equipped with complimentary toiletries, high defi ...
From $502 per night (USD)
VRBO
From $502 per night (USD)
VRBO
Classic King Room at Marker Key West Harbor - 3 Onsite Pools & Pet-Friendly
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This listing is for a room within a hotel. ✦ Your room is 400 sq. ft, equipped with complimentary toiletries, high defi ...
From $502 per night (USD)
VRBO
From $581 per night (USD)
VRBO
Perfect Getaway with Pools, Relaxing Atmosphere, and Resort Amenities
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This listing is for a room within a hotel. ✦ Your room is 400 sq. ft, equipped with complimentary toiletries, high defi ...
From $581 per night (USD)
VRBO
From $1617 per night (USD)
VRBO
Relaxing Key West Getaway with 3 Onsite Swimming Pools, Minutes to Beaches
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
This listing is for 3 separate rooms within a hotel. The price shown in the listing covers all 3 rooms. ✦ Each room is ...
From $1617 per night (USD)
VRBO
From $1045 per night (USD)
VRBO
2 Queen Rooms at Marker Key West Harbor - 3 Onsite Pools & Pet-friendly
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms. ✦ Each room is ...
From $1045 per night (USD)
VRBO
From $1045 per night (USD)
VRBO
Relaxing Key West Retreat with Resort Pool, Minutes to Beaches & Attractions
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms. ✦ Each room is ...
From $1045 per night (USD)
VRBO
From $1095 per night (USD)
VRBO
Tropical Key West Retreat with 3 Swimming Pools, Steps from Dining & Shops
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms. ✦ Each room is ...
From $1095 per night (USD)
VRBO
From $523 per night (USD)
VRBO
Escape to Paradise with Relaxing Pools and Watersports Right at Your Door
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This listing is for a room within a hotel. ✦ Your room is 400 sq. ft, equipped with complimentary toiletries, high defi ...
From $523 per night (USD)
VRBO
From $363 per night (USD)
Expedia
Charming pet friendly 2 bed/2 bath cottage 3 blocks from Duval
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Consider this cottage your home away from home while you visit Key West. This pet friendly property features 2 bedrooms ...
From $363 per night (USD)
Expedia
Click For Pricing
VRBO
Magnificent views of the Gulf, Sunset Harbor is the ultimate island retreat.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Nestled in Key West, this delightful resort offers 2 bedrooms with a king and queen bed, 2 bathrooms with luxurious amen ...
Click For Pricing
VRBO
From $696 per night (USD)
Expedia
BELLE MAISON ~ 5 BR/3 Ba Home w/ Pool/Spa in The Meadows!
Bedrooms:
3
Bathrooms:
5
Sleeps:
14
A LEGACY OF TIMELESS BEAUTY... This exquisite grand dame of quintessential Key West is a world of dreams! Yours is comin ...
From $696 per night (USD)
Expedia
From $409 per night (USD)
VRBO
Pet Friendly / Hot Tub / Close to Everything
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Located in Historic Old Town Monthly Rental La Cala is Situated on a Corner Lot within Walking Distance to Everything yo ...
From $409 per night (USD)
VRBO
From $258 per night (USD)
Expedia
SUNNY OUTLOOK~2 BR/2Ba 2nd FL, Waterfront views, Pool Access & Dockage!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This home is currently listed for sale and has been priced to offset showings that may be requested during your stay. ...
From $258 per night (USD)
Expedia
From $258 per night (USD)
VRBO
**SOUTHARD PEARL @ OLD TOWN** Condo & Community Pool + LAST KEY SERVICES…
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Among the man ...
From $258 per night (USD)
VRBO
From $561 per night (USD)
Expedia
Hyatt Sunset Harbor 1-bedroom suite w/AC, WiFi, Pool, Walk to Duval & Mallory
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Experience Key West in this enchanting 1-bedroom sleep4 suite with kitchen, living area with a queen sofa bed. Perfect f ...
From $561 per night (USD)
Expedia
From $1543 per night (USD)
VRBO
Conch Cove - 3br/3ba with private heated pool and private parking
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Conch Cove | Heated Pool & Prime Location! Conch Cove is your private oasis in Old Town Key West! This 3-bedroom, 3-bat ...
From $1543 per night (USD)
VRBO
From $146 per night (USD)
Expedia
Charming 1-bedroom/1-bath apartment in historical home with pool in Key West, FL
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Your cozy getaway awaits in Key West at this amazing apartment. Nestled in a beautiful private historical home in the he ...
From $146 per night (USD)
Expedia
From $368 per night (USD)
VRBO
~SUNNY DAZE COTTAGE~ A private, newly constructed home in best location.
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 $368 per night (USD)
VRBO
From $606 per night (USD)
Expedia
GEIGER SUITE @ Inn on Fleming~ADULTS ONLY 2 BR 3rd Floor & Shared Heated Pool
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
CAPTIVATING CLASSIC REVIVAL CHARM... Built in 1894, the delightful Inn on Fleming is an 11 room boutique hotel that was ...
From $606 per night (USD)
Expedia
From $224 per night (USD)
VRBO
TRUMAN ROOM @ Inn on Fleming~ADULTS ONLY 2nd Floor Queen & Shared Heated Pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
CAPTIVATING CLASSIC REVIVAL CHARM... Built in 1894, the delightful Inn on Fleming is an 11 room boutique hotel that was ...
From $224 per night (USD)
VRBO
From $758 per night (USD)
Expedia
Southern Escape at Truman Annex - 2 Bed / 2.5 Bath with Parking & Shared Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Southern Escape — Your Perfect Key West Getaway! Nestled in the heart of the Truman Annex Foundry building, ...
From $758 per night (USD)
Expedia
From $1168 per night (USD)
VRBO
Pool, Laundry, and grilling area
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
Upscale historic cigar barons mansion in walking distance to everything you desire in Key West. 3 spacious 1Br’s with o ...
From $1168 per night (USD)
VRBO
From $522 per night (USD)
Expedia
New Listing! Truman Show - Private, heated pool and chef's kitchen
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Truman Show combines a rich history, a modern renovation and a desirable Old Town location. This beautiful home is con ...
From $522 per night (USD)
Expedia
From $973 per night (USD)
VRBO
Sailfish Suite on Duval
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to the Sailfish Suite, your tropical retreat located in the heart of Key West! Situated on lively Duval Street, ...
From $973 per night (USD)
VRBO
From $622 per night (USD)
Expedia
Sunshine State at Custom House Inn | Bright Studio on Duval Street!
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Sunshine State at Custom House Inn | Bright Studio on Duval Street! Welcome to Sunshine State, your vibrant Key West es ...
From $622 per night (USD)
Expedia
From $1189 per night (USD)
VRBO
Two Vibrant Suites on Duval - Custom House Inn
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Feather Queen at Custom House Inn: A Key West Gem on Duval Street Located in the vibrant heart of Duval Street, Feather ...
From $1189 per night (USD)
VRBO
From $4265 per night (USD)
Expedia
Custom House Inn | 8 BR Suite Compound on Duval!
Bedrooms:
8
Bathrooms:
8
Sleeps:
25
Custom House Inn | Colorful Suites & Rooftop Vibes on Duval Street! Experience the ultimate group getaway at Custom Hou ...
From $4265 per night (USD)
Expedia
From $515 per night (USD)
VRBO
Two Modern Suites on Duval - Custom House Inn
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Chicken Water Cabana at Custom House Inn Located in the heart of vibrant Duval Street, Chicken Water Cabana at Custom H ...
From $515 per night (USD)
VRBO
From $305 per night (USD)
Expedia
Underwater Cabana at Custom House Inn | Right In The Heart, On Duval!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Underwater Cabana at Custom House Inn | Stay on Duval Street! Experience the heart of Key West with a stay at the Under ...
From $305 per night (USD)
Expedia
From $593 per night (USD)
VRBO
Birds of a Feather at Custom House Inn | Perfect Spot On Duval!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Birds of a Feather at Custom House Inn | Vibrant Stay on Duval Street! Discover the heart of Key West at Birds of a Fea ...
From $593 per night (USD)
VRBO
From $626 per night (USD)
Expedia
Chicken Run at Custom House Inn | Unbeatable Location On Duval!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Chicken Run at Custom House Inn | Stay on Duval Street! Welcome to Chicken Run, a vibrant and uniquely themed studio lo ...
From $626 per night (USD)
Expedia
From $662 per night (USD)
VRBO
Citrus Queen at Custom House Inn | Ideal Location On Duval!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Citrus Queen at Custom House Inn | On Duval St! | Bright & Modern Studio Welcome to Citrus Queen, your vibrant, modern ...
From $662 per night (USD)
VRBO
From $744 per night (USD)
Expedia
Penthouse Near Downtown - The Maloney
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Woven throughout this 2,000+ square foot luxury penthouse is a story that can only be revealed by experience. ...
From $744 per night (USD)
Expedia
From $373 per night (USD)
VRBO
This cottage is a 1 bedroom(s), 1 bathrooms, located in Key West, FL.
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to 734 Passover Lane, a charming one-bedroom cottage nestled in the heart of Key West’s historic district. This ...
From $373 per night (USD)
VRBO
From $700 per night (USD)
VRBO
Coral Palms Spacious 1BR Condo, King, Queen, Sofa Bed, Pool, Block to Duval
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Escape to this charming 1BR, 2nd-floor condo in the heart of Historic Key West. Sleep soundly in a plush king bed with r ...
From $700 per night (USD)
VRBO
$\Dominica\ Key West 2BR • Dock, Pool, Pet-Friendly$
From $731 per night (USD)
VRBO
\"Dominica\" Key West 2BR • Dock, Pool, Pet-Friendly
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Summary: Relax in this 1,200 sq. ft. waterfront home in historic Downtown Key West! Walk or bike less than 1 mile to Duv ...
From $731 per night (USD)
VRBO
From $436 per night (USD)
VRBO
Windsor Blue Your Island Hideaway in the Heart of Old Town Key West with a Private Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Windsor Blue— Your Island Hideaway in the Heart of Old Town Key West Tucked away on charming Windsor Lane an ...
From $436 per night (USD)
VRBO
From $374 per night (USD)
VRBO
The Kaleidoscope House - A Colorful Key West Hideaway w Pool & Jacuzzi
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
A camera roll full of the best family vacation memories is inevitable at The Kaleidoscope House: A Colorful Key West Sta ...
From $374 per night (USD)
VRBO
From $568 per night (USD)
VRBO
The Meadows Retreat
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Your Island Escape Awaits – Tropical Luxury in the Heart of Key West Welcome to your dream getaway in the Florida Keys— ...
From $568 per night (USD)
VRBO
From $736 per night (USD)
VRBO
Waterfront Condo with FREE Slip & Pool 2B/2B in Key West with AC
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Key West Waterfront Paradise – FREE Boat Slip Included! Wake up to breathtaking marina views, unwind in the heated pool ...
From $736 per night (USD)
VRBO
From $799 per night (USD)
VRBO
Old Town 3/3 Home, Private Pool, Off Street Parking, Outdoor Dining, Balconies
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Welcome to paradise in Old Town Key West! This spacious 3BR/3BA home features gorgeous hardwood floors, a huge dining ro ...
From $799 per night (USD)
VRBO
From $317 per night (USD)
VRBO
Charming bed & breakfast suite by the pool in lovely Key West.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Nestled in Key West, this delightful bed & breakfast features a cozy bedroom with a king bed, a bathroom with a refreshi ...
From $317 per night (USD)
VRBO
From $695 per night (USD)
VRBO
Hyatt Sunset Harbor - 1 bedroom sleep 4 condo steps from Duval & Mallory Square
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Hyatt Sunset Harbor Resort is located right on the water in the heart of Key West. Steps away is the famous Mallory Squa ...
From $695 per night (USD)
VRBO
From $719 per night (USD)
VRBO
Key West Condo 2B/2B with Pool & Boat FREE Slip
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Key West Waterfront Paradise – Dockage Included! Escape to our charming Key West condo, where relaxation and adventure ...
From $719 per night (USD)
VRBO
From $413 per night (USD)
VRBO
Charming two floor 1-bedroom bed & breakfast in fantastic Key West with AC
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Key West is waiting for you at this 1-bedroom bed & breakfast. A brilliant king bed awaits guests in this peaceful retre ...
From $413 per night (USD)
VRBO
From $204 per night (USD)
VRBO
Rooftop Renaissance - Upscale Condo in Old Town Key West. Perfect for Couples.
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
Rooftop Renaissance vacation rental falls into a distinctive design category of Heritage Victorian - Meets Modern Luxury ...
From $204 per night (USD)
VRBO
From $141 per night (USD)
VRBO
Apartment in historical hotel/home downtown Key West, one block off Duval St.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
A beautiful loft style apartment in a historical hotel/home in the heart of Key West awaits you! There is an 8ft deep pr ...
From $141 per night (USD)
VRBO
From $154 per night (USD)
VRBO
The Ivy Cottage - Private Home in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Tucked away on a quiet street in the heart of Old Town Key West you will find the quaint and comfortable Ivy Cottage. Th ...
From $154 per night (USD)
VRBO
From $1343 per night (USD)
VRBO
Fantastic Location, Old Town Waterfront Galleon Resort+Amenities, 2-Bedroom
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to 𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢 !! Our Galleon Resort accommodations in Historic Old Town-Key West, Florida – Where ...
From $1343 per night (USD)
VRBO
From $2439 per night (USD)
VRBO
2 Hyatt Sunset Harbor Resort, In Town, Marina
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This stylish place is close to must-see destinations. Discover this relaxing oasis in the heart of Key West's famed Old ...
From $2439 per night (USD)
VRBO
From $894 per night (USD)
VRBO
SEAPORT PANORAMA-Beach-Pool-King-BBQ-Kitchen views!
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
From $769 per night (USD)
VRBO
FLEMING-O (Flamingo) Cottage is the perfect getaway
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Fleming-O (pronounced “flamingo”) is located on one-way Fleming Street in the middle of historic Old Town Key West and o ...
From $769 per night (USD)
VRBO
From $1579 per night (USD)
VRBO
Modern Elegance at Windsor Townhomes #5
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
These beautiful villas boast over 1700 sq ft. on two levels for your vacation destination, with it’s own private garden ...
From $1579 per night (USD)
VRBO

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