FLORIDA KEY WEST VACATION RENTALS
Finest Luxury Vacations offers you a variety of hand selected Florida Key West vacation rentals. Choose beach houses, condos and cottages in Key West Florida. Florida Luxury Vacation Rentals offers you the opportunity to explore the wonderful keys, a tropical beach paradise from coast to coast.
Direct information is provided to you as a directory. Enjoy browsing through all our wonderful Key West vacation homes, condo's, cottages and villas. You have the opportunity to see all we have to offer, so you can contact the provider directly for information, availability, reservations, special deals.
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EXCLUSIVE SHOWCASE COLLECTION:
FUN IN THE FLORIDA KEYS and KEY WEST...
Above & BELOW ADVENTURES - Florida Keys Fishing Charters
WHERE ADVENTURE STARTS – FISH FLORIDA'S BEST!
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HISTORIC KEY WEST VACATION RENTALS - EXPLORE KEY WEST
Explore the vibrant charm of Key West with our comprehensive area guide. From sun-soaked beaches and water adventures to iconic festivals and historic landmarks, this island paradise offers something for everyone. Discover the best places to eat, drink, and explore, and stay up-to-date with local events and insider tips.
KEY WEST EXCLUSIVE SHOWCASE PROVIDER - VACATION HOMES OF KEY WEST...
VACATION HOMES OF KEY WEST - KHKW
Vacation Homes of Key West is well established as a premier vacation rental management company. We continue to offer what our founder envisioned as, “authentic Key West vacation rentals, where you can really live your Key West vacation island style.” We are constantly adding inventory to our curated assortment of one-of-a-kind island homes. BOOK DIRECT & SAVE!
KEY WEST PROPERTIES...
Ashe House - Monthly Rental
Sleeps 6 | 3 Bedrooms | 3.5 Bathrooms | Historic Vacation Home
CLICK HERE for Rates & Availability
As you enter the home via its white picket fence and comfortable front porch, you will be uplifted by sunshine. Hardwood floors and high-end finishes are reflected in this home while a bit of Key West charm is revealed…
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“HISTORIC KEY WEST VACATION RENTALS”
The Conch House Heritage Inn
Stay in the Main House, Poolside Cabana or 2 Story Cottage
CLICK HERE for Rates & Availability
All of the elegant grandeur of an Historic Key West Inn. Guests can choose from spacious and elegant bedrooms in the main house, furnished with individually selected antiques, the Caribbean inspired guest rooms in the two-story poolside cottage, or our cozy poolside cabana …
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“THE CONCH HOUSE HERITAGE INN”
Mango Cottage
6 Guests | 2 Bedrooms | 2 Bathrooms | Cottage with Private Saltwater Pool
CLICK HERE for Rates & Availability
This historic conch house is an excellent vacation home which has been thoughtfully remodeled to provide the best in modern comfort while carefully preserving the home's historic Key West architecture. Outdoor living is perhaps the best part of Key West life…
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Havana Lane
4 Guests | 2 Bedrooms | 2 Bathrooms | Pet Friendly Cottage with Pool
CLICK HERE for Rates & Availability
Welcome to this Pet Friendly Havana Lane Paradise! Enter the private courtyard of the home, to a lush tropical oasis. The large, free form pool with coral stone patio makes you ready to dive right in and relax poolside amongst the tropical foliage…
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Tropical Tee Time Villa
4 Guests | 2 Bedrooms | 2 Bathrooms | Cozy Villa in Tropical Haven
Starting at $4590 per Month
Escape to a stunning vacation rental in Key West, nestled on a picturesque golf course within an amazing resort. This prime location offers a tropical haven, perfect for those seeking relaxation and adventure…
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“KEEZY VACATION RENTALS”
Changes In Latitude
8 Guests | 4 Bedrooms | 3 Bathrooms | Waterfront Retreat with Private Pool
Starting at $12,000 per Month
Escape to coastal perfection at this upscale waterfront retreat in Key Haven, just minutes from Old Town Key West and Duval Street. Relax in the spacious, sun-filled living and dining areas, which open onto the outdoor patio with a covered porch and private pool…
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Azur Palm - Monthly Rental
Sleeps 4 | 2 Bedrooms | 2 Bathrooms | Ocean Front Vacation Home
Starting at $10,371 per Month
As you open the door to this amazing home via its tiled, arched portico you will be greeted by seas of blue! Off the entry hall is a stunning white kitchen with tray ceiling, upgraded appliances, quartz countertops and counter seating for four…
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Hibiscus Cottage
Sleeps 4 | 1 Bedrooms | 2 Bathrooms | Adult Only Setting
CLICK HERE for Rates & Availability
Welcome to your private rocking chair front porch and tropical, Adult Only setting! As you enter your quaint cottage, you can sit back and relax in the comfortable living room with ample seating for you and your guests…
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Margarita Cottage
Sleeps 2 | 1 Bedrooms | 1 Bathrooms | Studio Cottage
CLICK HERE for Rates & Availability
Stroll down the brick path to your Conch style studio cottage with an ensuite bath. This newly acquired and improved charming home sits in a quiet, residential part of Old Town yet remains close to so many Key West attractions…
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Robinson Crusoe Cottage
Sleeps 4 | 1 Bedrooms | 1 Bathrooms | Quaint Conch Cottage
CLICK HERE for Rates & Availability
This newly acquired and improved one-bedroom cottage has all you need to relax and unwind. Whether walking to Duval Street, Mallory Square, or nearby restaurants, you will enjoy a comfortable stay in an ideal location…
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The Conch Cottages
Sleeps 8 | 3 Bedrooms | 3 Bathrooms | Quaint Cottages with Pool
CLICK HERE for Rates & Availability
Plan your next group vacation in these quaint cottages with a pool. Located in Old Town, only a few blocks from Duval Street, this walkable residential neighborhood offers easy access to shops, bars, and restaurants…
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Colony Poolside
2 Guests | 1 Bedrooms | 1 Bathrooms | Bungalow in Historic Old Town
CLICK HERE for Rates & Availability
A charming 1 bedroom bungalow located in Historic Old Town Key West. This cottage has an open living/dining area, full kitchen and spacious bedroom with king size bed. Located in a compound with a large shared pool…
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Casa Amor
8 Guests | 3 Bedrooms | 3.5 Bathrooms | Modern Pool Home
CLICK HERE for Rates & Availability
A contemporary island gem that was formerly used as a bottling plant, this modern and spacious home is now a desirable tropical retreat located in the heart of Key West. A captivating historic essence luring you in with the finest of amenities…
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Casa Loca
8 Guests | 3 Bedrooms | 2.5 Bathrooms | Modern Pool Home
CLICK HERE for Rates & Availability
Casa Loca is perfect for guests who want to enjoy the finest that Key West has to offer! The perfect location, less than one block from Duval Street, this 3 bedroom, 2.5 bathroom house will amaze you with its extraordinary decor and attention to detail…
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Butterfly Cottage - Nightly Rental
Sleeps 4 | 2 Bedrooms | 2.5 Bathrooms | Cozy Cottage on Quiet Lane
CLICK HERE for Rates & Availability
Enjoy your coffee on the front porch or listen to the birds while gliding on the swing. Either way, you will acclimate to the Key West vibe in no time. Located on a teeny tiny quiet lane, this beautifully renovated home is trimmed with a white picket fence…
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Casablanca - Nightly Rental
Sleeps 4 | 1 Bedrooms | 1 Bathrooms | Pet Friendly Pool Home
CLICK HERE for Rates & Availability
Between the welcoming front porch and the private pool, you will be sure to enjoy fresh air and sunshine during your stay. This unpretentious home is comfortably furnished and ready to welcome you and your fur baby…
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Casablanca Too - Nightly Rental
Sleeps 2 | 1 Bedrooms | 1 Bathrooms | Pet Friendly Pool Home
CLICK HERE for Rates & Availability
Half Duplex. Enjoy fresh air and sunshine from your front porch or backyard hot tub at Casablanca Too. This unpretentious home has been beautifully updated and is ready to welcome you. The living room looks out to the covered front porch…
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Casablanca Grande - Nightly Rental
Sleeps 6 | 2 Bedrooms | 2 Bathrooms | Spacious Pet Friendly Pool Home
CLICK HERE for Rates & Availability
Both Sides of Duplex- Enjoy fresh air and sunshine from your front porch, private pool or hot tub at Casablanca Grande. You are not far from the excitement of Duval Street in this home but far enough away to enjoy peace and quiet…
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California Dreaming - Monthly Rental
Sleeps 7 | 4 Bedrooms | 3 Bathrooms | Luxury Pool Home
CLICK HERE for Rates & Availability
From its people watching front porch to its private heated pool, this home will surround you in tranquility. On the right side of the home’s entrance is a comfortably furnished living room with plenty of natural light…
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Casa Loca
4 Guests | 2 Bedrooms | 2 Bathrooms | Key West Style Cottage
CLICK HERE for Rates & Availability
Catherine House is a two bedroom two bathroom Key West style cottage located only 1/2 block from the quieter end of Duval Street. The covered front porch, small conversation pool, open floor plan and high ceilings create an inviting ambience…
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Coconut Cabana
6 Guests | 3 Bedrooms | 2 Bathrooms | Pool Home in Historic District
CLICK HERE for Rates & Availability
This one and a half story home with 3 bedrooms and 2 baths is beautifully decorated with warm tropical colors and light wood tone floors. The living room opens to the private deck, garden and lagoon style dip pool…
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Namaste
2 Guests | 1 Bedrooms | 2 Bathrooms | Cottage by Duval Street
CLICK HERE for Rates & Availability
Hidden away in an inviting compound. This one bedroom, two bath cottage has a private courtyard for a restful vacation experience. It is secluded in an inviting, tropical compound which is tranquil, but steps from Duval Street…
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Pilars Secret
8 Guests | 3 Bedrooms | 2 Bathrooms | Old Town Pool Home
CLICK HERE for Rates & Availability
Pilar’s Secret is hidden away in the heart of Old Town Key West just half a block off the famous Duval Street. This secluded oasis is the perfect spot for you to truly discover the ultimate Key West experience. Well appointed luxury amenities throughout…
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MANSION @ The Watson House
14 Guests | 7 Bedrooms | 7 Bathrooms | 3 Story Victorian Mansion
CLICK HERE for Rates & Availability
The Mansion, circa 1840’s is a lovingly restored and renovated three story Classic Folk Victorian home with seven bedrooms and seven bathrooms. A nice size pool area and off street parking enhance this classic home. The exterior also offers outdoor living at its tropical finest…
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Chavez House - Nightly Rental
Sleeps 6 | 3 Bedrooms | 2 Bathrooms | Pet Friendly Pool Home
CLICK HERE for Rates & Availability
By bringing the outdoors in, this home allows you to live like a true Floridian. The fenced yard provides you with privacy to enjoy your pool. Sun yourself on the lounge chairs or dine under the stars…
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Chick-a-Pea Cottage - Nightly Rental
Sleeps 8 | 4 Bedrooms | 2.5 Bathrooms | Pet Friendly Pool Home
CLICK HERE for Rates & Availability
Come enjoy the Key West cottage lifestyle where you can people watch from your front porch or take a dip in your pool. Whether you lounge in the cabana or enjoy dinner under the stars, this home has it all!…
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Cloud 9 - Nightly Rental
Sleeps 7 | 3 Bedrooms | 3 Bathrooms | Luxury Pool Home
CLICK HERE for Rates & Availability
If you are looking for a peaceful retreat that is close to everything, this is the ultimate home for you. As you enter your portal to paradise via the custom iron gecko gate, you will immediately feel as if you have left all your cares behind…
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Tropical Cottage @ Tropical Village
6 Guests | 2 Bedrooms | 2 Bathrooms | Pet Friendly Cottage
CLICK HERE for Rates & Availability
Tropical Cottage is a quintessential 1930s-era Conch bungalow, lovingly renovated with contemporary island elegance. This charming cottage is set back from the street in a quiet, upscale, gated enclave of six historic Old Key West vacation rentals…
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Toon Hall @ Tropical Village
10 Guests | 3 Bedrooms | 2 Bathrooms | Pet Friendly Cottage
CLICK HERE for Rates & Availability
Spacious 3BR/2BA 1930s-era Conch cottage w/ a storied past! Toon Hall was the winter retreat of Pulitzer Prize cartoonist Jeff MacNelly, illustrator of the comic strip Shoe. Private decks w/ alfresco dining. The common area (pool, deck w/ grill, picnic table…
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Royal Escape
10 Guests | 3 Bedrooms | 3 Bathrooms | Key West Hideaway
CLICK HERE for Rates & Availability
Royal Escape offers tropical seclusion and easy access to all of the night life, shopping, and grand dining of Old Town Key West. Surrounded by bamboo and palm trees, the Royal Escape features a completely private heated pool and Jacuzzi…
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Villa Paradiso
6 Guests | 3 Bedrooms | 3 Bathrooms | Beautiful Pool Home
CLICK HERE for Rates & Availability
This three bedroom three bathroom home is beautifully decorated with outdoor access from nearly every room. The outdoor dining room sits steps from the private pool and the house is near mid-town beaches and White Street Pier…
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Eyebrow Suite @ Eyebrow House
4 Guests | 2 Bedrooms | 1.5 Bathrooms | Spacious Suite by Duval Street
CLICK HERE for Rates & Availability
Eyebrow Suite is a spacious two-bedroom suite with one of the best locations on the island. Its large front porch and palm tree-filled fenced-in yard invite you to a private oasis on Olivia street, just a half block from Duval Street…
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Copa Cabana - Monthly Rental
Sleeps 4 | 2 Bedrooms | 2 Bathrooms | Quaint Pool Home
CLICK HERE for Rates & Availability
This home’s white picket fence and rocking chair front porch beckon you to come inside. Explore the uniqueness of this updated property including its location in Bahama Village, private pool, and pool house…
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Dreaming on Duval - Nightly Rental
Sleeps 10 | 5 Bedrooms | 4.5 Bathrooms | Spacious Pool Home
CLICK HERE for Rates & Availability
Dreams do come true in Key West! As you enter the front gate of this luxury property, you arrive in a private wonderland on the quieter end of Duval Street. Enjoy morning coffee or people watching on the elevated, partially covered front porch…
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Fair Winds at the Foundry - Weekly Rental
Sleeps 6 | 2 Bedrooms | 2.5 Bathrooms | 3 Story Townhome
CLICK HERE for Rates & Availability
As you open the white picket gate to this three-story townhouse, your tropical courtyard and outdoor dining area will delight you. Whether you spend a day at the pool or a night on Duval Street, you won’t be disappointed with this townhouse…
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Fleming-O
6 Guests | 2 Bedrooms | 1 Bathrooms | Cottage in Historic Old Town
CLICK HERE for Rates & Availability
located on one-way Fleming Street in the middle of historic Old Town Key West and only two blocks from world famous Duval Street and its restaurants, bars, art galleries, and shops. This completely upgraded conch cottage has all the modern amenities you would need…
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Casa Caribe
8 Guests | 4 Bedrooms | 4 Bathrooms | Spacious Family Vacation Home
CLICK HERE for Rates & Availability
When you think of the Caribbean, you think of tranquil blue green waters and a fun vibe and that's the feel when you walk into the garden of Casa Caribe. This wonderful four bedroom, four bath home is perfect for a couples or family getaway…
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Absolutely Paradise
8 Guests | 3 Bedrooms | 2.5 Bathrooms | 3 Story Pool Home
CLICK HERE for Rates & Availability
This newly redecorated town home is the perfect place to enjoy the tranquility of an island paradise vacation while still located in the heart of Old Town Key West. Absolutely Paradise is a hidden oasis perfect for relaxing after a fun time on Duval Street…
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Louisas Hideaway
6 Guests | 3 Bedrooms | 3 Bathrooms | Stylish Pool Home
CLICK HERE for Rates & Availability
Hidden near the upper end of Duval Street you'll find this stylish, newly renovated three bedroom, three bath home. Thoughtful details are luxuriously appointed to suit the vacation guest looking for privacy and high design…
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Porchside Paradise @ Conch Republic Cottage
4 Guests | 1 Bedrooms | 1 Bathrooms | Beautiful Home away from Home
CLICK HERE for Rates & Availability
Porchside Paradise is located in the front section of the Conch Republic Cottages. This beautiful home-away-from-home features an inviting and spacious front porch—great for people watching…
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Grand Maison - Nightly Rental
Sleeps 8 | 4 Bedrooms | 4.5 Bathrooms | Historic Pool Home
CLICK HERE for Rates & Availability
This home’s Key West charm and modern amenities make for a wonderful stay. From the Adirondack chair front porch to the private backyard pool, you will quickly fall into the island vibe in this home…
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Horse Conch - Nightly Rental
Sleeps 4 | 1 Bedrooms | 1 Bathrooms | Cozy Compound Unit
CLICK HERE for Rates & Availability
Enjoy your stay in the tropics at Horse Conch, part of the highly touted “Queen Conch” complex, which includes 3 separate rentable units: Horse Conch, Rooster Conch, and Sea Conch. You can rent each unit separately or rent “Queen Conch” to enjoy all 3 units …
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Rooster Conch - Nightly Rental
Sleeps 4 | 1 Bedrooms | 1 Bathrooms | Cozy Compound Unit
CLICK HERE for Rates & Availability
Enjoy your stay in the tropics at Rooster Conch, part of the highly touted “Queen Conch” complex, which includes 3 separate rentable units: Horse Conch, Horse Conch, and Sea Conch. You can rent each unit separately or rent “Queen Conch” to enjoy all 3 units …
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Sea Conch - Nightly Rental
Sleeps 6 | 2 Bedrooms | 2 Bathrooms | Cozy Compound Unit
CLICK HERE for Rates & Availability
Enjoy your stay in the tropics at Sea Conch, part of the highly touted “Queen Conch” complex, which includes 3 separate rentable units: Sea Conch, Horse Conch, and Rooster Conch. You can rent each unit separately or rent “Queen Conch” to enjoy all 3 units…
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Royal Poinciana Cottage
2 Guests | 1 Bedrooms | 1 Bathrooms | Beautiful Studio Cottage
CLICK HERE for Rates & Availability
Just beyond the white picket fence and rocking chair front porch, our newly acquired and improved studio cottage awaits you! This quiet residential area is the ideal place to relax and then walk or bike to the excitement on Duval Street…
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Queen Conch - Nightly Rental
Sleeps 14 | 4 Bedrooms | 4 Bathrooms | Spacious Pool Home
CLICK HERE for Rates & Availability
Enjoy your stay in the tropics at the highly touted “Queen Conch” complex, which includes 3 separate rentable units: Horse Conch, Rooster Conch, and Sea Conch. You can rent each unit individually, but by renting “Queen Conch” you will enjoy all 3 units…
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A Slice of Paradise -Shipyard Palms
4 Guests | 2 Bedrooms | 1.5 Bathrooms | Condo in Gated Community
CLICK HERE for Rates & Availability
This two bedroom one-and-a-half bath condo is located in the gated community of the Shipyard close to Duval Street and Fort Zachary Taylor State Park Beach. Enjoy the large deck with ample sun or venture to the community pool for a dip…
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Sea Orchid @ La Brisa 405E
4 Guests | 2 Bedrooms | 1.5 Bathrooms | Condo by the Beach
CLICK HERE for Rates & Availability
Sea Orchid is a two bedroom two bathroom condo at La Brisa residential condominiums. Located opposite of Key West's largest beach, La Brisa offers many amenities including a large pool, hot tub, tennis courts, dry saunas and off street parking…
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Duval Square Penthouse
10 Guests | 4 Bedrooms | 4.5 Bathrooms | Luxury Penthouse in Old Town
CLICK HERE for Rates & Availability
This 4 bedroom, 4.5 bath condo has enough luxurious square footage for your whole crew to gather, relax, and make lasting memories together. Located in the heart of old town, but securely and quietly hidden on the rooftop above the restaurants, galleries…
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Vista Fresco
6 Guests | 2 Bedrooms | 2 Bathrooms | Oceanside Luxury Condo
CLICK HERE for Rates & Availability
Vista Fresco is a two bedroom two bathroom condo located in the 1800 Atlantic Condominiums complex which sits on 400 feet of oceanfront property. Enjoy the expansive pool and spa Oceanside, plan a picnic in the beautiful gardens or relax on your balcony…
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Island Style @ Colony
4 Guests | 1 Bedrooms | 1 Bathrooms | Pet Friendly Luxury Condo
CLICK HERE for Rates & Availability
This quaint property offers resort-style accommodations at an affordable price! Nestled among a colony of freestanding Conch style cottages, amid lush tropical landscaping, sits Island Style, the sister cottage of Hidden Treasure…
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Blue Haven - Monthly Rental
Sleeps 8 | 4 Bedrooms | 3 Bathrooms | Private Key West Home
CLICK HERE for Rates & Availability
When you need Chaos Interrupted, this attractive home with a private, bougainvillea-adorned gate and a fenced yard welcomes you. The main entrance leads to the open concept family room and dining area…
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Palm Hideaway - Monthly Rental
Sleeps 6 | 3 Bedrooms | 2 Bathrooms | Single Story Pool Home
CLICK HERE for Rates & Availability
A private gate provides entry to this single-story home and your very own carport. From here you will walk into the beautiful open-concept family room and kitchen. Don’t wait until it’s sold out, book your Key West vacation at Palm Hideaway now!…
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Sunset Cove - Monthly Rental
Sleeps 5 | 2 Bedrooms | 3 Bathrooms | Waterfront Townhome with Pool
Starting at $7420 per Month
This townhome on the water is a rare find in Key West. Enjoy indoor-outdoor living as you saunter out the oversized French doors onto your lanai. From there you can entertain friends, take a dip in the pool, or walk out to the water and launch your kayak!…
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Inn Cogneato Cottage - Monthly Rental
4 Guests | 2 Bedrooms | 2 Bathrooms | Beautiful Pool Home
CLICK HERE for Rates & Availability
Step inside the white picket fence and enjoy your private escape. Surrounded by lush greenery and palm trees, this home with modern amenities is tucked into a charming, historic neighborhood. From here you can walk to many attractions Key West …
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La Casita en Cima - Monthly Rental
6 Guests | 2 Bedrooms | 2 Bathrooms | Pet Friendly Vacation Home
CLICK HERE for Rates & Availability
Located less than two blocks from Duval Street, this fully renovated home in Historic Old Town is walkable to many of the island’s attractions, including restaurants, bars, and shops. A 2016 recipient of The Historic Florida Keys Foundation’s Preservation Award…
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La Maisonnette - Nightly Rental
4 Guests | 1 Bedrooms | 1.5 Bathrooms | Pet Friendly Condo
CLICK HERE for Rates & Availability
This quiet residential oasis is in the middle of everything Key West. Vacationing in this gated community, surrounded by lush foliage, will give you a taste of what it might be like to live here…
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Lilly's Pad - Nightly Rental
6 Guests | 3 Bedrooms | 3.5 Bathrooms | Stunning Pool Home
CLICK HERE for Rates & Availability
Awarded the Florida Keys Preservation Star, this stunning home and outdoor space will entice you to live like a local. From its covered front porch to its rear entertaining area, you won’t want to leave…
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Maisons de Luxe - Nightly Group Rental
12 Guests | 6 Bedrooms | 6.5 Bathrooms | Large 2 Story Pool Home
CLICK HERE for Rates & Availability
With plenty of space in an ideal location, Maisons de Luxe combines a large two-story home with a stylish two-story cottage. Family, friends, or wedding guests will appreciate being together yet apart in this smart setting…
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Paradise on Porter
4 Guests | 2 Bedrooms | 2.5 Bathrooms | Townhome with Pool
CLICK HERE for Rates & Availability
Paradise on Porter is a wonderful vacation townhome located in the desirable Truman Annex area of downtown Key West. This townhome is very convenient to all there is to do in downtown Key West. Enjoy the quaintness of this fabulous neighborhood on your next visit to Key West…
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Sunrise Suite 203
6 Guests | 2 Bedrooms | 2.5 Bathrooms | Private Condo
CLICK HERE for Rates & Availability
A quiet alternative to the bustling noise of downtown Key West. Located just a 10-minute drive from all of the nightlife, shopping, restaurants, and activities of world-famous Duval Street, Sunrise Suite is your own private condo in our island paradise…
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Orchid Suite
4 Guests | 1 Bedrooms | 1 Bathrooms | Bi-level Suite
CLICK HERE for Rates & Availability
The Orchid Suite is a bi-level suite decorated in a rich contemporary Danish style. The bedroom is located upstairs with a bookcase divider separating two different sleeping areas, each with a queen bed. Orchid Suite is a half-block from the famous Duval Street…
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La Casa de Luces
6 Guests | 2 Bedrooms | 2 Bathrooms | Private Pool Home
CLICK HERE for Rates & Availability
Come relax or play while enjoying the spectacular sunsets and blue waters of Key West! This spacious ground-level two-bedroom, two-bathroom property is located in the heart of Key West right off of Duval Street. A private, enclosed patio…
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Beach Club Shangra La #206
6 Guests | 3 Bedrooms | 2 Bathrooms | Waterfront Corner Condo
CLICK HERE for Rates & Availability
Enjoy endless views just feet away from the tranquil waters of the Atlantic Ocean. Condo 206 is a serene waterfront oasis located in the Key West Beach Club, an upscale gated community with two oceanfront pools, pavilion area, workout room and tennis court…
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Beach Club Seabreeze #103
5 Guests | 2 Bedrooms | 2 Bathrooms | Waterfront Luxury Condo
CLICK HERE for Rates & Availability
This spacious two bedroom two bath condo sits 65′ from the Atlantic in the secured Beach Club complex. Enjoy your large private Oceanfront balcony, shared Oceanside pool, tennis court, BBQs, workout room and sauna…
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My Happy Place-Monthly Rental
4 Guests | 2 Bedrooms | 2 Bathrooms | Quaint Home with Dip Pool
CLICK HERE for Rates & Availability
From its delightful mosaic-tiled, covered front porch to its back yard dip pool, this Key West home will surprise you! Petite yet grand, this home is walkable to many attractions. The backyard area is secluded and beautifully landscaped…
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Petite Maison - Nightly Rental
4 Guests | 2 Bedrooms | 2 Bathrooms | Second Floor Vacation Rental
CLICK HERE for Rates & Availability
An open staircase leading to the second floor is where your vacation begins! The reverse floor plan, tres chic décor, and open living room with vaulted ceiling are dazzling. Relax and mingle with guests in this beautiful, functional space…
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Poinciana Garden - Nightly Rental
3 Guests | 1 Bedrooms | 1 Bathrooms | First Floor Duplex
CLICK HERE for Rates & Availability
Located on a teeny tiny quiet lane, this comfortably furnished first-floor duplex home comes with Key West charm and contemporary touches. To explore the second-floor home, search for “Poinciana Treetop,” or book “Poinciana Paradise” to reserve the entire home for family or friends…
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Poinciana Treetop - Nightly Rental
3 Guests | 1 Bedrooms | 1 Bathrooms | First Floor Duplex
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Located on a teeny tiny quiet lane, this comfortably furnished second-floor duplex home comes with Key West charm and contemporary touches. To explore the second-floor home, search for “Poinciana Garden,” or book “Poinciana Paradise” to reserve the entire home for family or friends…
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Poinciana Paradise - Group Rental
6 Guests | 2 Bedrooms | 2 Bathrooms | Full Duplex Group Rental
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Located on a teeny tiny quiet lane, this comfortably furnished duplex home comes with Key West charm and contemporary touches. Walkable to many shops and attractions, you will feel like a local in no time. Only two blocks to Duval Street…
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Potter's Cottage - Nightly Rental
5 Guests | 2 Bedrooms | 2 Bathrooms | Charming Pool Home
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Enjoy the walkable location of this charming property. As you enter the home from its covered rocking chair front porch, you are in the open concept living room and kitchen. Ideal for a small family or two couples, this home provides a bedroom and full bath on each level…
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Moondance @ La Brisa
6 Guests | 2 Bedrooms | 2 Bathrooms | Luxury Beach Condo
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Escape to the luxury of Moondance at La Brisa, a gated Condo community, just steps from the beach on Key West's Atlantic coast. This condo will provide a getaway you won't forget. Walk into the tranquil setting…
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Cuban Paradise @ Cuban Club
6 Guests | 2 Bedrooms | 2 Bathrooms | Condo on Duval Street
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Escape the stress and cares of your daily life with a vacation to the wonderful Cuban Paradise @ Cuban Club! This roomy two-bedroom condo has a private balcony to enjoy all the hustle and energy of the famous Duval Street…
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A Cuban Club Suite
8 Guests | 2 Bedrooms | 2 Bathrooms | Luxury Suite on Duval Street
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The Cuban Club Suite stands as an award-winning historical landmark converted to a gorgeous two-bedroom suite filled with all the amenities needed for comfortable living. Enjoy your very own private balcony overlooking Duval Street…
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Hidden Treasure @ Colony
6 Guests | 2 Bedrooms | 2 Bathrooms | Pet Friendly Cottage
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Hidden from sight, among a colony of freestanding conch cottages and surrounded by lush tropical landscaping, you will find Hidden Treasure. Truly a treasure, it is the sister cottage of Island Style, owned by two sisters who share a passion for Key West…
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Tranquility On Ann Street
2 Guests | 1 Bedrooms | 1 Bathrooms | Charming Cottage with Shared Pool
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This charming one bedroom one bathroom cottage is in a tropical compound with a shared pool. Located steps off Duval next to The Curry Mansion. King sized bed, spa bath and private deck will make this a pleasant Key West vacation…
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Colony Conch Casa
6 Guests | 3 Bedrooms | 2.5 Bathrooms | Large 2 Story Home
Starting at $187 per Night (monthly rental)
This monthly rental is a large two-story home that feels like a single family, but it is part of The Colony of Key West Condominiums, an exclusive community just two short blocks from Duval Street…
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Reel Paradise - Monthly Rental
5 Guests | 3 Bedrooms | 2.5 Bathrooms | Town Home with Pool
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This townhouse invites its guests to enjoy the peace and serenity of island life with new hurricane doors and windows. This beautiful home, with new art and accessories, is so warm and inviting! As you enter the gate, you will pass by the shared pool and gardens…
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Sanctuary on South - Monthly Rental
8 Guests | 4 Bedrooms | 3.5 Bathrooms | Two Story Pool Home
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Amble through the portico entrance into this gorgeous two-story retreat. The covered front porch is an ideal place to enjoy your morning coffee and that is just the beginning! Upon entering the home, you will be greeted by upscale furnishings…
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Sea Vista - Monthly Rental
7 Guests | 3 Bedrooms | 2.5 Bathrooms | Waterfront Vacation Home
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Dreaming of putting your toes in the sand or sipping coffee on your dock? Then this is the vacation home for you! The lush backyard is gated and leads out to the warm Gulf of Mexico. Just steps from the water’s edge…
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Seas The Day! - Weekly Rental
4 Guests | 2 Bedrooms | 1 Bathrooms | Condo with Shared Pool
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This 2-bedroom 1 bathroom condo with an oversized shared pool is a wonderful place to kick back and relax after exploring the island. Located near the excitement of Duval Street yet tucked back near the water…
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Serene Lily - Weekly Rental
6 Guests | 2 Bedrooms | 2.5 Bathrooms | Upscale Pool Home
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Located where the Gulf meets the Atlantic, this is the upscale vacation home you have been looking for! Stroll down your private entrance in the Historic Truman Annex to this elegantly decorated single family home…
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A Bit of Heaven
6 Guests | 3 Bedrooms | 3 Bathrooms | Pool Home in Historic District
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Welcome to A Bit of Heaven! This quintessential Key West eyebrow home is located in Old Town's prime Historic District, sitting just blocks away from Duval Street, the Historic Seaport, the Art District, and all of the amazing things Key West has to offer…
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Reynolds Retreat
6 Guests | 3 Bedrooms | 3 Bathrooms | Pool Home just off Duval Street
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Reynolds Retreat is quintessential Key West living. Located just a few blocks off Duval Street, Reynolds Retreat is a delightful cottage filled with historic charm and modern convenience. The perfect spot to make your home-away-from-home in paradise…
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South St. Cottage
4 Guests | 2 Bedrooms | 2 Bathrooms | Pet Friendly Pool Home
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South Street Cottage is a sunny two bedroom, two bathroom with a large open kitchen, skylights and plenty of French doors for the ultimate indoor/outdoor living experience. The main bedroom suite opens to a private patio space with 6-person hot tub!…
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Soleil Chalet
8 Guests | 3 Bedrooms | 3 Bathrooms | Pet Friendly Pool Home
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Your own private paradise awaits in this peaceful neighborhood just steps away from the buzz of Duval Street. “Soleil Chalet” is a completely restored cottage delivering easy access to all Key West has to offer while still providing a quiet retreat from the nightly celebrations downtown…
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Living the Dream
6 Guests | 3 Bedrooms | 3 Bathrooms | Pet Friendly Pool Home in Old Town
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Steps from the Key West Seaport and just a few blocks from world famous Duval Street in Old Town Key West is this exquisitely renovated vacation home complete with a private backyard and a pool, providing plenty of space for lounging to soak up the Florida sun…
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Ceasar's Paradise
10 Guests | 5 Bedrooms | 4.5 Bathrooms | Luxury Home in Old Town
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Modern sophistication is the design aesthetic in this newer built 4 bedroom, 5.5 bath home in Old Town. The home includes bonus spaces of an office and an upstairs den with sofa sleeper, there is space for everyone in this home…
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Solaris Cottage - Nightly Rental
2 Guests | 1 Bedrooms | 1 Bathrooms | Quaint Duplex in Old Town
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This one bedroom, one bath, first-floor duplex is conveniently located in Old Town. Walkable to so many Key West activities, you won’t need a car, just a pair of sandals or a bicycle. Tucked down a quiet one-way lane, this casual home is comfortably furnished…
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Solaris Garden - Nightly Rental
2 Guests | 1 Bedrooms | 1 Bathrooms | Quaint Duplex in Old Town
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This unit in the duplex home comes with shared outdoor amenities including a deck under a giant Banyan tree, a grill, and an outdoor washer and dryer. Solaris Garden is ideal for the traveler looking for walkability as well as the desire to kick back and relax…
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Solaris Pair-A-Dise - Nightly Rental
4 Guests | 2 Bedrooms | 2 Bathrooms | Tropical Island Vibe Duplex
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If you are looking for that tropical island vibe, look no further! Both sections of this casual home are comfortably furnished. Located on a teeny tiny quiet lane, you will find Bohemian bits indoors and lush landscaping outdoors…
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Southard Comfort - Nightly Rental
6 Guests | 3 Bedrooms | 2.5 Bathrooms | Enchanting Pool Home
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Enchanted 3-bedroom home. Live like a local in this unique Key West property. Designed for relaxation and indoor-outdoor living, this home exudes local architecture, art, and joie de vivre. From its welcoming front porch to its private back yard…
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The Escape at Sunset Key - Monthly Rental
6 Guests | 2 Bedrooms | 3 Bathrooms | Enchanting Pool Home
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Upon arriving at this private island, you will immediately notice the peaceful quiet that car-free, traffic-free living affords. The security and privacy that this island offers make this a great place for families, children, or couples…
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The Pink House - Monthly Rental
5 Guests | 2 Bedrooms | 3 Bathrooms | 2 Story Pool Home
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Enjoy beverages on the balconies or a splash in the pool, as you being to unwind and enjoy your vacation. Filled with sunshine and happiness, this two-story pink gem provides space and privacy for families or friends…
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Casa Blanca
8 Guests | 4 Bedrooms | 3 Bathrooms | Luxury Pool Home
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Welcome to Casa Blanca (monthly rental) – This single level, open floor plan home has four bedrooms, three full baths, a large open living room/dining room, beautiful kitchen, multiple outdoor living spaces, and custom pool. This is a monthly rental…
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Beach Club #104
6 Guests | 2 Bedrooms | 2 Bathrooms | Spacious Waterfront Condo
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Welcome to Beach Club #104! This spacious two bedroom two bath condo sits 65′ from the Atlantic in the secured Beach Club complex. Enjoy your large private Oceanfront balcony, shared Oceanside pool, tennis court, BBQs, workout room and sauna…
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Key Lime Cottage
4 Guests | 2 Bedrooms | 3 Bathrooms | Pet Friendly Pool Home
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Key Lime Cottage Paradise! Located on the edge of Old Town near the art district on White Street. Key Lime Cottage offers great accommodations for up to 4 people. This lovely cottage has a welcoming front porch worthy of morning coffee…
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Sans Souci
7 Guests | 3 Bedrooms | 3 Bathrooms | Private Pool Home
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Sans Souci is a gorgeous Key West vacation home with a pool and lush tropical foliage. Relax by your own private pool or go out on the town! Key West Seaport is only two blocks away! CASA BLANCA IS A MONTHLY RENTAL…
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Aloha
10 Guests | 4 Bedrooms | 4 Bathrooms | Pet Friendly Pool Home
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Aloha is a stunning private residence on corner lot in the Casa Marina District. Updated 2 years ago, this beautiful home features 4 bedrooms and 4 full baths with a chef's kitchen, living room, dining room, and family room all on one floor…
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Three Arches in Paradise - Monthly Rental
6 Guests | 3 Bedrooms | 3.5 Bathrooms | Luxury Pool Home
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Three arches in Paradise is where your holiday begins! Passing through the wrought iron gate you will be wowed by the home’s arched facade, hardscape, and tropical foliage. Your stay at Three Arches in Paradise will leave you wanting to spend the rest of your life here!…
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Tropical Dream - Monthly Rental
8 Guests | 4 Bedrooms | 4.5 Bathrooms | Luxury Pool Home
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You will be greeted by beautiful porches and tropical greenery. Drop your luggage at the door and go for a swim. Around back, a private pool with waterfall feature awaits you. Later, you can cozy up to a bedroom of your choice…
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Villa Azul - Monthly Rental
6 Guests | 3 Bedrooms | 3 Bathrooms | Pool Home in Old Town
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Located in the heart of Old Town Key West on a teeny tiny quiet lane, this two-story home with a first-floor bedroom is ideal for the entire family. Your guests or young adults may enjoy the privacy of their own pool house with an ensuite half bath and delightful outdoor shower…
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Villa Josine - Nightly Rental
8 Guests | 4 Bedrooms | 4.5 Bathrooms | Historic Pool Home
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Villa Josine not only has curb appeal but also is a stunning example of a Key West eyebrow house. Unlike those of the 1800’s, this home has been completely renovated with modern amenities and high-end designer finishes. It’s large enough for your entire family to enjoy…
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