Fleming Key Rentals
From $207 per night (USD)VRBO
**BARBUDA SUITE @ SEAPORT INN** Guest Suite w\/ Pool Access + LAST KEY SERVICES..
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Looking for a ...
From $207 per night (USD)VRBO
From $222 per night (USD)Expedia
**MATECUMBE SUITE @ SEAPORT INN** Guest Suite w\/ Pool Access + LAST KEY SERVICES
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! If you’d like ...
From $222 per night (USD)Expedia
From $209 per night (USD)VRBO
**ANTIGUA SUITE @ SEAPORT INN** Guest Suite w\/ Pool Access + LAST KEY SERVICES..
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! If the allure ...
From $209 per night (USD)VRBO
From $612 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 $612 per night (USD)Expedia
From $1933 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 $1933 per night (USD)VRBO
From $366 per night (USD)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 ...
From $366 per night (USD)Expedia
From $339 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 $339 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:
- 3
- 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 $548 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 $548 per night (USD)VRBO
From $667 per night (USD)Expedia
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 $667 per night (USD)Expedia
From $456 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 $456 per night (USD)VRBO
From $648 per night (USD)Expedia
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 $648 per night (USD)Expedia
From $385 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 $385 per night (USD)VRBO
From $966 per night (USD)Expedia
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 $966 per night (USD)Expedia
From $485 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 $485 per night (USD)VRBO
From $428 per night (USD)Expedia
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 $428 per night (USD)Expedia
From $483 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 $483 per night (USD)VRBO
From $489 per night (USD)Expedia
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 $489 per night (USD)Expedia
From $513 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 $513 per night (USD)VRBO
From $1449 per night (USD)Expedia
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 $1449 per night (USD)Expedia
From $486 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 $486 per night (USD)VRBO
From $458 per night (USD)Expedia
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 $458 per night (USD)Expedia
From $519 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 $519 per night (USD)VRBO
From $1534 per night (USD)Expedia
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 $1534 per night (USD)Expedia
From $996 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 $996 per night (USD)VRBO
From $1055 per night (USD)Expedia
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 $1055 per night (USD)Expedia
From $1025 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 $1025 per night (USD)VRBO
From $531 per night (USD)Expedia
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 $531 per night (USD)Expedia
From $770 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 $770 per night (USD)VRBO
From $1506 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 $1506 per night (USD)Expedia
From $285 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 $285 per night (USD)VRBO
From $440 per night (USD)Expedia
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 $440 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 $3804 per night (USD)Expedia
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)Expedia
From $569 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 $569 per night (USD)VRBO
From $1057 per night (USD)Expedia
Modern Elegance at Windsor Townhomes #5
- Bedrooms:
- 4
- 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 $1057 per night (USD)Expedia
From $1423 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 $1423 per night (USD)VRBO
From $692 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 $692 per night (USD)Expedia
From $837 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 $837 per night (USD)VRBO
From $795 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 $795 per night (USD)Expedia
From $921 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 $921 per night (USD)VRBO
Click For PricingExpedia
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 PricingExpedia
From $174 per night (USD)VRBO
Quaint Pool Cottage in Old Town Key West Great value
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Perfectly situated in Old Town Key West. This quaint pool cottage is perfect for a couple with occasional visitors. beau ...
From $174 per night (USD)VRBO
From $707 per night (USD)Expedia
FERNWOOD ~ Dreamy, Lush Estate with Incredible Outdoor Space with Pool & Spa!
- Bedrooms:
- 4
- 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 $707 per night (USD)Expedia
From $2508 per night (USD)VRBO
Old Town Caribbean Estate Key West - Great for Groups - Private Pool - Sleeps 21
- Bedrooms:
- 8
- 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 $2508 per night (USD)VRBO
From $1737 per night (USD)Expedia
Harbor House Suite A | 4 Bed, 4 Bath
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Welcome to Luxury Harbor House Suites, an exceptional NIGHTLY vacation rental property located in the heart of Key West' ...
From $1737 per night (USD)Expedia
From $285 per night (USD)VRBO
UPTOWN FUNK ~ Newly Renovated 3 BR Townhome in Old Town with Parking!
- Bedrooms:
- 3
- 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 $285 per night (USD)VRBO
From $494 per night (USD)Expedia
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 $494 per night (USD)Expedia
From $280 per night (USD)VRBO
Old Town cottage
- Bedrooms:
- 2
- 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 $280 per night (USD)VRBO
From $1474 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 $1474 per night (USD)Expedia
From $351 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 $351 per night (USD)VRBO
From $156 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 $156 per night (USD)Expedia
From $305 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 $305 per night (USD)VRBO
From $382 per night (USD)Expedia
Conch Cottage Retreat in the heart of Old Town Key West
- Bedrooms:
- 3
- 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:
- 4
- 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
Click For PricingExpedia
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 ...
Click For PricingExpedia
From $469 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 $469 per night (USD)VRBO
From $460 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 $460 per night (USD)Expedia
From $242 per night (USD)VRBO
Garden of Eden Cottage | 1 Bed, 1.5 Bath
- Bedrooms:
- 2
- 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 $242 per night (USD)VRBO
From $355 per night (USD)Expedia
524 Elizabeth St. #2
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Enjoy a stylish experience at this centrally-located place. Located just blocks from duval and many of it's restaurants ...
From $355 per night (USD)Expedia
From $355 per night (USD)VRBO
613 Fleming. St. Unit 1
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Great location in the heart of it all. Short walk to Duval Street, bars, shops and restaurants. Quiet enough to have a p ...
From $355 per night (USD)VRBO
From $577 per night (USD)Expedia
The Leonella, Old Town Key West.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Leonella is an Imaginative and impeccable restoration of a Key West conch house mixing contemporary style and histor ...
From $577 per night (USD)Expedia
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 $641 per night (USD)Expedia
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)Expedia
From $302 per night (USD)VRBO
Classic King & Private Balcony - Curry Mansion Inn
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...
From $302 per night (USD)VRBO
From $1738 per night (USD)Expedia
Key West Suites Hotel #201 on Duval
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Key West Suites Hotel #201 Welcome to your charming private studio apartment right on Duval street! Built in 1919, it u ...
From $1738 per night (USD)Expedia
From $433 per night (USD)VRBO
Old Town Bali Hideaway For 2, Just Steps From Duval
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Perfect for two, this Bali style, studio cottage has it all... COMFORT and LOCATION. Located on an Ann Street compound j ...
From $433 per night (USD)VRBO
From $329 per night (USD)Expedia
Hidden Treasure in Old Town: 3BR Home with Pool in Peaceful Gated Enclave
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 5
Your Key West Hideaway home is located in the heart of Old Town. Key West landmarks, attractions, Duval St, restaurants, ...
From $329 per night (USD)Expedia
From $299 per night (USD)VRBO
Private Home in Heart of Old Town (Shared Pool!)
- Bedrooms:
- 2
- 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 $299 per night (USD)VRBO
From $277 per night (USD)Expedia
The Rex, a Key West Monthly Rental
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Enjoy a stylish experience at this centrally-located apartment. Just a short walk from some of Key West best restaurants ...
From $277 per night (USD)Expedia
From $337 per night (USD)VRBO
The Maria Luz, a Key West Monthly Rental
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The Maria Luz a is located in a Historic Conch house from the early 1900’s updated and decorated by its owner. Feature ...
From $337 per night (USD)VRBO
From $276 per night (USD)Expedia
The Gisela, a Key West Monthly Rental
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 1
The Gisela is located in the rear of an adorable Conch Cottage. Finished with a soft and neutral color scheme that will ...
From $276 per night (USD)Expedia
From $894 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 $894 per night (USD)VRBO
From $220 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 $220 per night (USD)Expedia
From $920 per night (USD)VRBO
Heart of Key West - 2BR Waterfront at the Galleon Resort
- Bedrooms:
- 2
- Bathrooms:
- 3
- 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 $920 per night (USD)VRBO
From $246 per night (USD)Expedia
WINDSONG DELIGHT - Cute house on Windsor Ln
- Bedrooms:
- 3
- 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 $246 per night (USD)Expedia
From $471 per night (USD)VRBO
TROPICAL PROPERTIES VACATION RENTAL-KEY WEST
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
****This property requires a minimum stay of 28 nights in the same calendar month**** Tropical Properties Vacation Rent ...
From $471 per night (USD)VRBO
From $3331 per night (USD)Expedia
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 $3331 per night (USD)Expedia
From $844 per night (USD)VRBO
Luxury Waterfront Stay @ The Galleon, Mins from Downtown
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Imagine waking up every morning in Paradise. With Balconies that overlook the marina and ocean. Private marina, private ...
From $844 per night (USD)VRBO
From $2285 per night (USD)Expedia
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 $2285 per night (USD)Expedia
From $1120 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 $1120 per night (USD)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
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The Queens Villa
- Bedrooms:
- 4
- 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 PricingVRBO
From $406 per night (USD)Expedia
LOVE IS IN THE AIR - Charming Home-On private lane w\/pool sleeps 6
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Enjoy a month-long stay or longer in this beautiful Three-bedroom Key West Home. Hidden in the heart of Old-Town Key W ...
From $406 per night (USD)Expedia
From $845 per night (USD)VRBO
**SOUTHERNMOST BLISS @ OLD TOWN** Newly Renovated Home & Pool + LAST KEY SERVICE
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 9
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! SOUTHERNMOST ...
From $845 per night (USD)VRBO
From $314 per night (USD)Expedia
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 $314 per night (USD)Expedia
From $647 per night (USD)VRBO
The Conch Chateau: Stylishly Renovated Conch House in the Heart of Key West, Heated\/Chilled Pool!
- Bedrooms:
- 2
- Bathrooms:
- 5
- 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 $647 per night (USD)VRBO
From $394 per night (USD)Expedia
Unlock your Paradise Adventure - Between Sloppy Joe's and the Harbor
- Bedrooms:
- 4
- 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 $900 per night (USD)VRBO
Two-bedroom townhouse overlooking the harbor.\n \nONLY AVAILABLE Nov. 9 - Nov 16
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Two story townhouse with two bedrooms, pull out couch, full kitchen, three bathrooms. Overlooking the harbor with full ...
From $900 per night (USD)VRBO
From $409 per night (USD)Expedia
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 $409 per night (USD)Expedia
From $398 per night (USD)VRBO
**MODERN IN THE MEADOWS @ THE MEADOWS** Chic Private Home & Pool + LAST KEY SERV
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! MODERN IN THE ...
From $398 per night (USD)VRBO
From $267 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 $267 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 $414 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 $414 per night (USD)Expedia
From $241 per night (USD)VRBO
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 $241 per night (USD)VRBO
From $470 per night (USD)Expedia
**ANGELA’S ECLECTIC GALLERY @ SOLARIS HILL** Exceptional Home & Pool + LAST KEY
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! On an island ...
From $470 per night (USD)Expedia
From $460 per night (USD)VRBO
Tranquility by AvantStay | Close to Duval St w\/ BBQ & Shared Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- 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 $460 per night (USD)VRBO
From $437 per night (USD)Expedia
Paradise Place by AvantStay | Key West Old Town Condo w\/ Shared Pool
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Cozy apartment within biking distance to The Historic Seaport, Cuban Coffee Queen, local grocery store Fausto's, and eve ...
From $437 per night (USD)Expedia
From $461 per night (USD)VRBO
CONCH CASA @ The Colony ~ the perfect monthly escape
- Bedrooms:
- 3
- 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 $461 per night (USD)VRBO
From $1814 per night (USD)Expedia
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 $1814 per night (USD)Expedia