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 $2026 per night (USD)
VRBO
Meadows Manor | Elegant Oasis with Private Pool & Parking!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Meadows Manor | Elegant Oasis with Private Pool & Parking --- 3-Night Minimum Stay Required --- Discover the perfect b ...
From $2026 per night (USD)
VRBO
From $344 per night (USD)
Expedia
African Queen | Perfect Suite Near Historic Seaport, Shared Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to African Queen Cottage, a charming retreat within the serene Harbor Walk Hideaways complex in Key West's Histo ...
From $344 per night (USD)
Expedia
From $396 per night (USD)
VRBO
Atocha Cottage at Harbor Walk Hideaways | 2 Blocks From Duval! Shared Pool
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Atocha Cottage at Harbor Walk Hideaways Welcome to Atocha Cottage, a serene getaway nestled within the charming Harbor ...
From $396 per night (USD)
VRBO
From $301 per night (USD)
Expedia
Pilar Cottage | Spectacular Studio w/ Shared Pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to Pilar Cottage, a charming studio located within the peaceful Harbor Walk Hideaways complex in Key West's Hist ...
From $301 per night (USD)
Expedia
From $923 per night (USD)
VRBO
Harbor Walk Hideaways | Group Compound In Old Town!
Bedrooms:
3
Bathrooms:
4
Sleeps:
14
Welcome to Harborwalk Hideaways! Overview: Discover Harbor Walk Hideaways, a beautifully renovated vacation rental comp ...
From $923 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 $259 per night (USD)
VRBO
HEMINGWAY SUITE @ Inn on Fleming~ADULTS ONLY 2nd Lvl King 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 $259 per night (USD)
VRBO
From $268 per night (USD)
Expedia
CORNISH SUITE @ Inn on Fleming ADULTS ONLY 3rd Floor 2 BR /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 $268 per night (USD)
Expedia
From $413 per night (USD)
VRBO
SIMONTON ROOM @ Inn on Fleming~ADULTS ONLY 1st Lvl King w/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 $413 per night (USD)
VRBO
From $321 per night (USD)
Expedia
GATO ROOM @ Inn on Fleming~ADULTS ONLY 2nd Floor Queen w/ 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 $321 per night (USD)
Expedia
From $224 per night (USD)
VRBO
FLAGLER ROOM @ Inn on Fleming~ADULTS ONLY 1st Floor King w/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 $297 per night (USD)
Expedia
WHITEHEAD ROOM @ Inn on Fleming~ADULTS ONLY 2nd Lvl 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 $297 per night (USD)
Expedia
From $439 per night (USD)
VRBO
MALLORY SUITE @ Inn on Fleming~ADULTS ONLY 1st Lvl King w/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 $439 per night (USD)
VRBO
Click For Pricing
Expedia
Waterfront Resort, Songwriter’s Fest, Old Town, Sleeps 4, Swimming Pool, Hot Tub
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Have I mentioned that this listing is for the Songwriter’s Festival in sunny Key West, FL? You will be staying at the Hy ...
Click For Pricing
Expedia
From $606 per night (USD)
VRBO
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)
VRBO
From $224 per night (USD)
Expedia
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)
Expedia
From $758 per night (USD)
VRBO
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)
VRBO
From $1168 per night (USD)
Expedia
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)
Expedia
From $522 per night (USD)
VRBO
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)
VRBO
From $973 per night (USD)
Expedia
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)
Expedia
From $1171 per night (USD)
VRBO
Charming 4-bedroom house with pool - 10 MIN. WALK TO DUVAL STREET
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
Welcome to 1015 Eaton Street, nestled in the heart of the Historic Seaport neighborhood. Renovated in 2024, this 4-bedro ...
From $1171 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 $631 per night (USD)
VRBO
Poolside Hide-Away @ Palm Gardens offered by Rent Key West Vacations
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Poolside Hide-Away is a first floor one bedroom, one bath historic condo, that can accommodate up to 4 people, with wrap ...
From $631 per night (USD)
VRBO
From $258 per night (USD)
Expedia
**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)
Expedia
From $561 per night (USD)
VRBO
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)
VRBO
From $949 per night (USD)
Expedia
~Hibiscus Cottage~ Adults Only cottage near Duval with shared pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
THE PROPERTY: Welcome to your private rocking chair front porch and tropical, Adult Only setting! As you enter your quai ...
From $949 per night (USD)
Expedia
From $303 per night (USD)
VRBO
WASTIN' A WAYLAND ~ Renovated 2 BR/2 Ba Home in Old Town!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
OLD TOWN GEM... This 2 bedroom, 2 bathroom cutie resides down a charming lane surrounded by historic residences and is a ...
From $303 per night (USD)
VRBO
From $1590 per night (USD)
Expedia
**The Three Mermaids @ Solaris Hill** New Construction Compound + Last Key Servi
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Finding a com ...
From $1590 per night (USD)
Expedia
From $317 per night (USD)
VRBO
Cozy on Caroline - Key West Seaport
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
Experience the quintessential Key West lifestyle in this charming one-bedroom, two-bathroom apartment that perfectly bal ...
From $317 per night (USD)
VRBO
From $255 per night (USD)
Expedia
Seaport Serenity Cottage - Quiet and Quaint
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This charming 2BR/2BA rental is located in the Historic Seaport District offering off-street parking and a prime locatio ...
From $255 per night (USD)
Expedia
From $531 per night (USD)
VRBO
Welcome Matt's - Truman @ Duval | Ideal One-Bedroom Retreat
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Truman @ Duval Unit B | Ideal One-Bedroom Retreat for Couples Escape to a charming one-bedroom apartment in the heart o ...
From $531 per night (USD)
VRBO
From $407 per night (USD)
VRBO
Tropical Island Retreat Near Florida Beaches with Pool & Views! Free Breakfast
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This listing is for a room within a hotel. ✦ Your room is 420 sq. ft, equipped with complimentary toiletries, standard ...
From $407 per night (USD)
VRBO
From $695 per night (USD)
VRBO
Charming Hideaway with Pool Access – Walk to Duval St! Free Breakfast!
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Enjoy vibrant Key West: steps to Duval Street's nightlife, historic sites, and serene beaches. Perfect for culture and s ...
From $695 per night (USD)
VRBO
From $482 per night (USD)
VRBO
Cozy Key West Escape – Near Shops, Bars & Famous Duval Street! Free Breakfast
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $482 per night (USD)
VRBO
From $704 per night (USD)
VRBO
**GRENN TURTLE COTTAGE @ THE ANNEX** Stunning Private Home + LAST KEY SERVICES…
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! GREEN TURTLE ...
From $704 per night (USD)
VRBO
From $731 per night (USD)
VRBO
Dos Casas - 2 House Compound in Old Town Key West - A Monthly Rental
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Dos Casas can be the answer to your fabulous Old Town Key West vacation. We've been renting to discerning travelers for ...
From $731 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 $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
Click For Pricing
Expedia
Charming condo in awesome Key West - great location!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Your cozy getaway awaits in Key West at this wonderful condo. With amenities like King Size Bed, Private Front Porch, Pr ...
Click For Pricing
Expedia
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
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 $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
$\Dominica\ Key West 2BR • Dock, Pool, Pet-Friendly$
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 $265 per night (USD)
Expedia
The Secret Garden - Quaint 2 Bedroom / 2 Bath Cottage with Shared Pool & Hot Tub
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
THE SECRET GARDEN – Charming 2 Bedroom / 2 Bathroom Cottage located in the Center of Old Town - 4 Guests - 2 Spaciou ...
From $265 per night (USD)
Expedia
From $340 per night (USD)
VRBO
**CALUSA SUITE @ SEAPORT INN ** Historic w/ Community Pool + LAST KEY SERVICES..
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 $340 per night (USD)
VRBO
From $626 per night (USD)
Expedia
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 $626 per night (USD)
Expedia
$NEW! - The Jolly Rooster Cottage\nSteps to Duval - Prime and Quiet Location$
From $506 per night (USD)
VRBO
NEW! - The Jolly Rooster Cottage\nSteps to Duval - Prime and Quiet Location
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to the Jolly Rooster! We’re thrilled to welcome you to our newly renovated, standalone cottage—proudly presente ...
From $506 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 $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 $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)
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 $1305 per night (USD)
VRBO
From $329 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 $329 per night (USD)
Expedia

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