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 $267 per night (USD)
VRBO
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 $267 per night (USD)
VRBO
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Expedia
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
Expedia
From $537 per night (USD)
VRBO
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 $537 per night (USD)
VRBO
From $399 per night (USD)
Expedia
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 $399 per night (USD)
Expedia
From $453 per night (USD)
VRBO
Historic Key West Hideaway – Walk to the Seaport! Outdoor Pool, Pets Allowed!
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 $453 per night (USD)
VRBO
From $4667 per night (USD)
Expedia
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 $4667 per night (USD)
Expedia
From $571 per night (USD)
VRBO
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 $571 per night (USD)
VRBO
From $1204 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 $1204 per night (USD)
VRBO
From $1557 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 $1557 per night (USD)
VRBO
From $515 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 $515 per night (USD)
VRBO
From $677 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 $677 per night (USD)
VRBO
From $1370 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 $1370 per night (USD)
VRBO
From $484 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 $484 per night (USD)
VRBO
From $685 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 $685 per night (USD)
VRBO
From $1105 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 $1105 per night (USD)
VRBO
From $947 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 $947 per night (USD)
VRBO
From $1152 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 $1152 per night (USD)
VRBO
From $870 per night (USD)
VRBO
Charming 2BR Stay, Ella’s | Garden Retreat w/ Pool Near Attractions & Eats
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 $870 per night (USD)
VRBO
From $841 per night (USD)
VRBO
~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 $841 per night (USD)
VRBO
From $325 per night (USD)
Expedia
~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 $325 per night (USD)
Expedia
From $204 per night (USD)
VRBO
**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 $204 per night (USD)
VRBO
From $166 per night (USD)
Expedia
**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 $166 per night (USD)
Expedia
From $204 per night (USD)
VRBO
**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 $204 per night (USD)
VRBO
From $609 per night (USD)
Expedia
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 $609 per night (USD)
Expedia
From $1266 per night (USD)
VRBO
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 $1266 per night (USD)
VRBO
Click For Pricing
Expedia
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
Expedia
From $306 per night (USD)
VRBO
**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 $306 per night (USD)
VRBO
From $325 per night (USD)
Expedia
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)
Expedia
From $380 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 $380 per night (USD)
VRBO
From $376 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 $376 per night (USD)
VRBO
From $334 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 $334 per night (USD)
VRBO
From $386 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 $386 per night (USD)
VRBO
From $429 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 $429 per night (USD)
VRBO
From $688 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 $688 per night (USD)
VRBO
From $348 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 $348 per night (USD)
VRBO
From $352 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 $352 per night (USD)
VRBO
From $353 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 $353 per night (USD)
VRBO
From $341 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 $341 per night (USD)
VRBO
From $369 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 $369 per night (USD)
VRBO
From $1033 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 $1033 per night (USD)
VRBO
From $367 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 $367 per night (USD)
VRBO
From $348 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 $348 per night (USD)
VRBO
From $363 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 $363 per night (USD)
VRBO
From $1093 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 $1093 per night (USD)
VRBO
From $699 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 $699 per night (USD)
VRBO
From $743 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 $743 per night (USD)
VRBO
From $729 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 $729 per night (USD)
VRBO
From $373 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 $373 per night (USD)
VRBO
From $248 per night (USD)
VRBO
Charming studio in Key West -Close to Duval. Beautiful Pool area.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Tropical Key West welcomes you to a classic Florida studio condominium, offering a plush king-size bed, casual living ar ...
From $248 per night (USD)
VRBO
From $1392 per night (USD)
VRBO
Perfect for Families! 2BR Suite with Balconies, Onsite Pool, Private Beach!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $1392 per night (USD)
VRBO
From $1392 per night (USD)
VRBO
Sea Breeze 2 Bedroom Oceanfront Suite at The Pier House Resort & Spa
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $1392 per night (USD)
VRBO
From $1760 per night (USD)
VRBO
Pet-friendly Accommodation with Balcony, Outdoor Pool, Private White Sand Beach!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $1760 per night (USD)
VRBO
From $1760 per night (USD)
VRBO
Havana Heights Two Bedroom Suite at The Pier House Resort & Spa
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $1760 per night (USD)
VRBO
From $296 per night (USD)
Expedia
**CALUSA SUITE @ SEAPORT INN ** Historic Charm & Community Pool + LAST KEY SERVI
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Want to be in ...
From $296 per night (USD)
Expedia
From $344 per night (USD)
VRBO
Heron Hideaway
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to our unique and charming VRBO in Key West, located just a short distance from downtown. This cozy retreat off ...
From $344 per night (USD)
VRBO
From $1350 per night (USD)
Expedia
Premier resort overlooking the Gulf. Walk to Mallory Square, restaurants, beach.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Imbibe the relaxed Key West lifestyle from a coveted location in the heart of Old Town. Perfectly situated on the wester ...
From $1350 per night (USD)
Expedia
From $103 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 $103 per night (USD)
VRBO
$\Dominica\ Key West 2BR • Dock, Pool, Pet-Friendly$
From $705 per night (USD)
VRBO
\"Dominica\" Key West 2BR • Dock, Pool, Pet-Friendly
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
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 $705 per night (USD)
VRBO
From $281 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 $281 per night (USD)
VRBO
From $471 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 $471 per night (USD)
VRBO
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 $1539 per night (USD)
Expedia
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 $1539 per night (USD)
Expedia
From $3804 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 $3804 per night (USD)
VRBO
From $530 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 $530 per night (USD)
VRBO
From $959 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 $959 per night (USD)
VRBO
From $1366 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 $1366 per night (USD)
VRBO
From $599 per night (USD)
VRBO
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 $599 per night (USD)
VRBO
From $333 per night (USD)
Expedia
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 $333 per night (USD)
Expedia
From $373 per night (USD)
VRBO
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 $373 per night (USD)
VRBO
From $151 per night (USD)
Expedia
THE HIDDEN GEM ~ Charming Renovated Studio with Large Community Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
HIDDEN GARDEN STUDIO… This charming 340 sq.ft. escape in the exclusive Lionsgate Condominium community will delight your ...
From $151 per night (USD)
Expedia
From $872 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 $872 per night (USD)
VRBO
From $203 per night (USD)
Expedia
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 $203 per night (USD)
Expedia
From $705 per night (USD)
VRBO
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)
VRBO
From $2541 per night (USD)
Expedia
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 $2541 per night (USD)
Expedia
From $1792 per night (USD)
VRBO
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 $1792 per night (USD)
VRBO
From $226 per night (USD)
Expedia
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 $226 per night (USD)
Expedia
From $438 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 $438 per night (USD)
VRBO
From $267 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 $267 per night (USD)
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 $1784 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 $1784 per night (USD)
Expedia
From $597 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 $597 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 $376 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 $376 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 $179 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 $179 per night (USD)
VRBO
From $412 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 $412 per night (USD)
Expedia
From $248 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 $248 per night (USD)
VRBO
From $288 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 $288 per night (USD)
Expedia
From $1738 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 $1738 per night (USD)
VRBO
From $501 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 $501 per night (USD)
Expedia
From $303 per night (USD)
VRBO
Historic Charm, Heart of Old Town, Tropical Paradise, Key West Quaint.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
3-Bedroom, 1.5-Bath Historic Conch House in the Heart of Old Town Key West This charming Conch house features a queen b ...
From $303 per night (USD)
VRBO
From $416 per night (USD)
Expedia
Paradise on Pine in Key West
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Paradise on Pine, is a picture perfect home that sits high above this lovely one way street with an inviting front porc ...
From $416 per night (USD)
Expedia
From $244 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 $244 per night (USD)
VRBO
From $219 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 $219 per night (USD)
Expedia
From $855 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 $855 per night (USD)
VRBO
From $215 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 $215 per night (USD)
Expedia
From $318 per night (USD)
VRBO
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 $318 per night (USD)
VRBO
From $466 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 $466 per night (USD)
VRBO

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