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.
BOOK YOUR FLORIDA KEY WEST VACATION RENTALS DIRECT & SAVE!
Direct information is provided to you as a directory. Enjoy browsing through all our wonderful destinations for tropical villas, beach condos, secluded cabins. Don't forget about our exciting All Inclusive Packages, Wedding Destinations, Adult Only Getaways, Dude Ranches and so much more! You have the opportunity to see all we have to offer, so you can contact the provider directly for information, availability, reservations, special deals.
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!
Reel in an Unforgettable Fishing Adventure with Capt. Jose at Above & Below Adventures – Your Go-To for Florida Key’s Best Outdoor Adventures! Discover the best fishing charter in Florida with Above & Below Adventures: Our expert guides, top-quality equipment, and picturesque surroundings guarantee the ultimate fishing experience.
Get ready to experience the trip of a lifetime – from family-friendly outings to thrilling trophy catches, we have the perfect fishing adventure for you!
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.
Whether you’re planning a family vacation, a romantic getaway, or an adventure with friends, our guide is here to help you uncover the magic of Key West. Dive into curated recommendations, expert blogs, and must-see attractions to make your trip unforgettable.
KEY WEST FLORIDA SHOWCASE PROVIDER...
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…
brought to you by
“HISTORIC KEY WEST VACATION RENTALS”
The Conch House Heritage Inn
Stay in the Main House, Poolside Cabana or 2 Story Cottage
Starting at $298 per Night
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 …
brought to you by
“THE CONCH HOUSE HERITAGE INN”
Vintage Luxury Cottage On Duval
4 Guests | 1 Bedrooms | 1 Bathrooms | Cottage with Private Heated Pool
CLICK HERE for Rates & Availability
One of the rarest private Key West luxury cottage rentals available. Situated in one of the most requested locations in Old Town Key West, this luxury renovated turn-of-the-century Vintage Luxury Cottage vacation rental is hidden just off upper Duval Street in Old Town…
brought to you by
“VACATION HOMES OF KEY WEST”
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…
brought to you by
“RENT KEY WEST”
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…
brought to you by
“RENT KEY WEST”
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…
brought to you by
“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…
brought to you by
“KEEZY VACATION RENTALS”
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…
brought to you by
“HISTORIC KEY WEST VACATION RENTALS”
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…
brought to you by
“HISTORIC KEY WEST VACATION RENTALS”
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…
brought to you by
“HISTORIC KEY WEST VACATION RENTALS”
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…
brought to you by
“HISTORIC KEY WEST VACATION RENTALS”
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…
brought to you by
“HISTORIC KEY WEST VACATION RENTALS”
Key West Sunset Sojourn
6 Guests | 3 Bedrooms | 4 Bathrooms | Dream Home on Private Island
CLICK HERE for Rates & Availability
Imagine the ultimate Key West dream home on a private island surrounded by sparkling turquoise waters and balmy breezes. Someplace elegant yet relaxed, where you can watch crowning tropical sunsets from a private rooftop lookout deck …
brought to you by
“VACATION HOMES OF KEY WEST”
Private Pool Garden Villa
6 Guests | 3 Bedrooms | 2.5 Bathrooms | Private Garden Oasis Home
CLICK HERE for Rates & Availability
Experience true tropical Key West living as the locals do in this spacious mid-century private garden oasis home with large swimming pool and trickling waterfall. Located just one block from the beach…
brought to you by
“VACATION HOMES OF KEY WEST”
Havana Moon Over Duval
6 Guests | 2 Bedrooms | 2 Bathrooms | Cottage on Upper Duval Street
CLICK HERE for Rates & Availability
Ideally located right at the top of Upper Duval Street and just down from Key West’s South Beach this historic residential cottage received a beautiful renovation and now offers 5-Star resort quality amenities. Catch a view of the ocean where the full moon rises with a soft salt southern breeze…
brought to you by
“VACATION HOMES OF KEY WEST”
Maison Soleil
6 Guests | 3 Bedrooms | 3 Bathrooms | Luxury Pool Home
CLICK HERE for Rates & Availability
If you’re looking for bright, beautiful sophistication for your Key West vacation, your search ends at Maison Soleil. This gorgeous, newly renovated Sunset Key villa features plentiful space, serene, clean design, a lovely outdoor area with a private pool, and so much more…
brought to you by
“VACATION HOMES OF KEY WEST”
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…
brought to you by
“RENT KEY WEST”
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…
brought to you by
“RENT KEY WEST”
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…
brought to you by
“RENT KEY WEST”
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…
brought to you by
“HISTORIC KEY WEST VACATION RENTALS”
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…
brought to you by
“HISTORIC KEY WEST VACATION RENTALS”
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…
brought to you by
“HISTORIC KEY WEST VACATION RENTALS”
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…
brought to you by
“HISTORIC KEY WEST VACATION RENTALS”
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…
brought to you by
“HISTORIC KEY WEST VACATION RENTALS”
Heavenly Hideout at Rainbow's End
8 Guests | 4 Bedrooms | 4 Bathrooms | Tropical Style Penthouse Vacation Rental
CLICK HERE for Rates & Availability
There aren’t many places in the world where you can say you’re both beginning and ending your journey at the same time. But when you rent this Heavenly Hideout at Rainbow’s End, you’re spot on, and you can do exactly that…
brought to you by
“VACATION HOMES OF KEY WEST”
Garden Suite
6 Guests | 2 Bedrooms | 2 Bathrooms | Boho Style Poolside Garden Suite
CLICK HERE for Rates & Availability
The allure of the boho style Garden Suite vacation rental comes from its one-of-a-kind architectural design, the original wood it is built with, the fun decor, and its authentic Key West pool garden setting. A creative decor in this fun and funky pool-side setting…
brought to you by
“VACATION HOMES OF KEY WEST”
Coco's Poolside Retreat
8 Guests | 3 Bedrooms | 2.5 Bathrooms | 3 Story Townhome
CLICK HERE for Rates & Availability
Coco’s Poolside Retreat is a 3-story Key West vacation rental townhouse situated in a one-of-a-kind private tropical pool garden compound. The townhouse is on the pool side of the complex. a tropical wonderland of a yard and walks right out to a huge, sparkling 40’ swimming pool…
brought to you by
“VACATION HOMES OF KEY WEST”
Key West Dreamin'
6 Guests | 2 Bedrooms | 2 Bathrooms | Private Historic Vacation Home
CLICK HERE for Rates & Availability
Key West Dreamin' vacation rental is a private historic home that is beautifully furnished and offers all the amenities of a luxury accommodation situated in a genuine Old Town Key West location. Located just off Duval on Catherine Street…
brought to you by
“VACATION HOMES OF KEY WEST”
The Kaleidoscope House
6 Guests | 3 Bedrooms | 3.5 Bathrooms | Private Key West Hideaway
CLICK HERE for Rates & Availability
A camera roll full of the best family vacation memories is inevitable at The Kaleidoscope House: A Colorful Key West Hideaway. Tucked away on a quiet, foliage-lined street in Old Town, this vibrant tropical retreat is nestled in and amongst the best of Key West…
brought to you by
“VACATION HOMES OF KEY WEST”
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…
brought to you by
“RENT KEY WEST”
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…
brought to you by
“RENT KEY WEST”
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…
brought to you by
“RENT KEY WEST”
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…
brought to you by
“RENT KEY WEST”
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…
brought to you by
“RENT KEY WEST”
Amanda's Dream Suites
10 Guests | 4 Bedrooms | 3 Bathrooms | Charming Historic Vacation Home
CLICK HERE for Rates & Availability
Amanda's Dream Suites vacation rental is a charming large wooden home offering two full stories with deep porches which overlook the garden and pool. An exterior stair case on one end of the building join the first and second floor…
brought to you by
“VACATION HOMES OF KEY WEST”
Governor's Retreat
4 Guests | 2 Bedrooms | 2 Bathrooms | Luxury Vacation Rental Cottage
CLICK HERE for Rates & Availability
If you’ve ever had the pleasure of wandering the historic streets and by-ways of downtown Key West, then you know how time seems to stand still. The Governor’s Retreat, offers all the modern-day amenities one could desire in an upscale island home…
brought to you by
“VACATION HOMES OF KEY WEST”
Blue Porch Cottage
4 Guests | 1 Bedrooms | 1.5 Bathrooms | Luxury Cottage with Pool
CLICK HERE for Rates & Availability
Check into the Blue Porch Cottage and waste no time getting settled into the true spirit of Key West. Situated snugly in Old Town, you’ll get all the historic charm yet all the modern amenities and style of this luxe rental. Make memories in beautiful Key West…
brought to you by
“VACATION HOMES OF KEY WEST”
Island Sunshine Bungalow
4 Guests | 2 Bedrooms | 1 Bathrooms | Historic Key West Cottage
CLICK HERE for Rates & Availability
Historic and designer at once, this imaginative one-and-a-half-story shot-gun cottage is ideally situated in the Heart of Old Town Key West. Enchanting as can be, feng shui elements were also used in both the renovation and decorating, to achieve a calming and relaxing ambience…
brought to you by
“VACATION HOMES OF KEY WEST”
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…
brought to you by
“HISTORIC KEY WEST VACATION RENTALS”
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!…
brought to you by
“HISTORIC KEY WEST VACATION RENTALS”
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…
brought to you by
“HISTORIC KEY WEST VACATION RENTALS”
Elegant Key West Tree House
4 Guests | 2 Bedrooms | 1 Bathrooms | Quaint Old Town Vacation Rental
CLICK HERE for Rates & Availability
Discretely built back off the street to quietly overlook an historic tropical garden, this Elegant Key West Tree House, encompasses the entire 2nd floor of a beautifully renovated 1930’s building. Today the large historic property is filled with tall giant white birds of paradise…
brought to you by
“VACATION HOMES OF KEY WEST”
Island Interlude
4 Guests | 2 Bedrooms | 2.5 Bathrooms | Luxurious 2 Story Town Home
CLICK HERE for Rates & Availability
Aspirational, luxurious, well appointed, and whimsical, are four attributes that best define this Key West courtyard townhome. Island Interlude, this 2-story property is situated in one of the most popular transitional urban scenes of Key West…
brought to you by
“VACATION HOMES OF KEY WEST”
Tropical Chill
4 Guests | 2 Bedrooms | 2 Bathrooms | 2 Story Cottage Style Flat
CLICK HERE for Rates & Availability
If you’re looking for a place to chill-out in the tropical warmth of Key West, this cottage-style flat is a wonderful place to relax and take a breather from everyday life. Situated in the elegant gated condominium community of Truman Annex…
brought to you by
“VACATION HOMES OF KEY WEST”
Ocean View Luxury Villa
8 Guests | 3 Bedrooms | 4 Bathrooms | Ocean View Luxury Vacation Home
CLICK HERE for Rates & Availability
Fashionably tucked behind a white picket fence on a quiet cal-de-sac street, this “beach-style” vacation house combines island living with luxury and minimalism in precisely the right way. Drawing from classic Key West architecture…
brought to you by
“VACATION HOMES OF KEY WEST”
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…
brought to you by
“RENT KEY WEST”
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…
brought to you by
“RENT KEY WEST”
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…
brought to you by
“RENT KEY WEST”
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…
brought to you by
“RENT KEY WEST”
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…
brought to you by
“RENT KEY WEST”
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…
brought to you by
“HISTORIC KEY WEST VACATION RENTALS”
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…
brought to you by
“HISTORIC KEY WEST VACATION RENTALS”
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…
brought to you by
“HISTORIC KEY WEST VACATION RENTALS”
Sweet Sunshine Garden Flat
4 Guests | 2 Bedrooms | 1 Bathrooms | Caribbean Cottage-style flat by the beach
CLICK HERE for Rates & Availability
Ever dream of vacationing in a sun-kissed Caribbean Cottage-style flat close to the beach, nestled behind a white picket fence in a landscaped tropical garden? Sweet Sunshine Garden Flat can make that dream come true…
brought to you by
“VACATION HOMES OF KEY WEST”
Hidden Story-Book Cottage
2 Guests | 1 Bedrooms | 1 Bathrooms | Luxury Cottage in Old Town Key West
CLICK HERE for Rates & Availability
Hidden Story-Book Cottage in the Old Town Key West. A gated walking path connects this hidden little cottage with Windsor Lane at the highest point of Key West. This quaint neighborhood in the middle of the island, is a testimony…
brought to you by
“VACATION HOMES OF KEY WEST”
Island Elegance
6 Guests | 3 Bedrooms | 3 Bathrooms | Luxury Corner Lot Vacation Home
CLICK HERE for Rates & Availability
Strikingly set in the oft-missed Key West mid-town neighborhood, we find Island Elegance, making a classical curbside statement with its craftsman-colonial architecture, lush mature tropical landscaping, and white picket fencing…
brought to you by
“VACATION HOMES OF KEY WEST”
Classic Key West Estate
14 Guests | 7 Bedrooms | 5.5 Bathrooms | Grand Historic Key West Pool Home
CLICK HERE for Rates & Availability
Featured on HGTV House Hunters on Vacation, the timeless charm of this distinguished Classic Key West Estate vacation rental is at once authentic and magnificent. This is a grand wooden Key West historic home…
brought to you by
“VACATION HOMES OF KEY WEST”
Truman Treasure
5 Guests | 3 Bedrooms | 2 Bathrooms | 2 Story Truman Annex Vacation Rental
CLICK HERE for Rates & Availability
The home has two entrances. The main entrance is through a manicured garden pathway leading to the front porch, and the back entrance is off the wooden deck and garden adjoining the kitchen…
brought to you by
“VACATION HOMES OF KEY WEST”
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…
brought to you by
“RENT KEY WEST”
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…
brought to you by
“RENT KEY WEST”
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…
brought to you by
“RENT KEY WEST”
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…
brought to you by
“RENT KEY WEST”
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…
brought to you by
“RENT KEY WEST”
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…
brought to you by
“HISTORIC KEY WEST VACATION RENTALS”
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 …
brought to you by
“HISTORIC KEY WEST VACATION RENTALS”
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 …
brought to you by
“HISTORIC KEY WEST VACATION RENTALS”
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…
brought to you by
“HISTORIC KEY WEST VACATION RENTALS”
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…
brought to you by
“HISTORIC KEY WEST VACATION RENTALS”
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…
brought to you by
“HISTORIC KEY WEST VACATION RENTALS”
Down Island Digs
6 Guests | 2 Bedrooms | 2 Bathrooms | Private Garden Cottage
CLICK HERE for Rates & Availability
Everything about this historic Key West tropical gem adds up to make a precious private garden cottage. Sitting in the mature tropical tree garden in the hidden back yard, you would never know you're just 1/2 block off Duval Street…
brought to you by
“VACATION HOMES OF KEY WEST”
Pavilion Villa
10 Guests | 4 Bedrooms | 3 Bathrooms | Prestigious Garden Home in Old Town
CLICK HERE for Rates & Availability
A Private Tropical Paradise … is the feeling you get when you enter the pavilion of this award winning villa just a half-block off Duval St. in Old Town Key West. Spectacular indoor and outdoor multi-level living space…
brought to you by
“VACATION HOMES OF KEY WEST”
Exclusive Key West Beach Front
6 Guests | 2 Bedrooms | 3 Bathrooms | Designer Oceanfront Luxury Condo Rental
CLICK HERE for Rates & Availability
Rare, one-of-a kind designer luxury condominium located in an exclusive gated Key West beachfront property. The Exclusive Key West Beachfront vacation rental has breath taking views overlooking the ocean…
brought to you by
“VACATION HOMES OF KEY WEST”
Duval Street Fantasy Resort Villa
8 Guests | 3 Bedrooms | 3 Bathrooms | Charming Cottage with Pool
CLICK HERE for Rates & Availability
This one-of-a-kind vacation rental perfectly blends two charming historic cottages right into a little bit of island heaven. Your own private tropical resort is the feeling you get when you enter the bricked courtyard of this extraordinary property…
brought to you by
“VACATION HOMES OF KEY WEST”
Twice as Nice on Duval Street
8 Guests | 4 Bedrooms | 4 Bathrooms | Twin-Cigar Maker's Cottages
CLICK HERE for Rates & Availability
Two is definitely better than One”! A rare set of early 1900's “twin-cigar maker's cottages” perched on the southern end of famous Duval Street. This vacation rental is adorable and elegant and a perfect solution for those who want to lodge together in luxury …
brought to you by
“VACATION HOMES OF KEY WEST”
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…
brought to you by
“RENT KEY WEST”
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…
brought to you by
“RENT KEY WEST”
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…
brought to you by
“RENT KEY WEST”
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…
brought to you by
“RENT KEY WEST”
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…
brought to you by
“RENT KEY WEST”
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…
brought to you by
“HISTORIC KEY WEST VACATION RENTALS”
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!…
brought to you by
“HISTORIC KEY WEST VACATION RENTALS”
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!…
brought to you by
“HISTORIC KEY WEST VACATION RENTALS”
Romance on William Street
8 Guests | 3 Bedrooms | 3.5 Bathrooms | Charming Pool Home
CLICK HERE for Rates & Availability
Discover the perfect blend of classic Key West charm and modern elegance at “Romance on William.” This stunning 3 to 3.5-bedroom vacation rental, nestled at 528 William St, invites you to experience a refined getaway that captures the essence of island living.
brought to you by
“VACATION HOMES OF KEY WEST”
Family Reunion Compound
21 Guests | 8 Bedrooms | 6.5 Bathrooms | 3 Story Pool Home
CLICK HERE for Rates & Availability
Thinking about getting your extended family or friends together for a Key West family reunion vacation? This one-of-kind gated Key West vacation rental compound, with a large shared swimming pool in spacious landscaped tropical garden setting, could be the perfect place…
brought to you by
“VACATION HOMES OF KEY WEST”
Villa Porta del Sole – Sunset Key
6 Guests | 3 Bedrooms | 3.5 Bathrooms | Luxurious Pool Home
CLICK HERE for Rates & Availability
Staying on Sunset Key is always magical—but even more so when you’re in one of the few homes with a completely unobstructed view of the western horizon. The outdoor space is where 10 Sunset Key truly shines. The heated pool invites gathering, play, and relaxation…
brought to you by
“VACATION HOMES OF KEY WEST”
The Grand Marshall
10 Guests | 5 Bedrooms | 4.5 Bathrooms | Luxury Family Retreat
CLICK HERE for Rates & Availability
This perfect combo of two upscale renovated homes, On Hemingway’s Rounds, and Governor’s Retreat, are ideally situated on separate lots with fenced backyards that border with each other. When you rent both, you get twice the space, double the privacy…
brought to you by
“VACATION HOMES OF KEY WEST”
Sunset Sonnet Luxury Villa
4 Guests | 2 Bedrooms | 3 Bathrooms | True Tropical Paradise
CLICK HERE for Rates & Availability
No other private Caribbean Island resort presents its exclusive homes with such enchanting elegance as Sunset Key. Rooftop Deck:Just outside the master bedroom, a custom spiral staircase takes you even higher to the intimate outdoor rooftop room…
brought to you by
“VACATION HOMES OF KEY WEST”
Ultimate Sunset Guest House
4 Guests | 2 Bedrooms | 2 Bathrooms | Key West Beach House
CLICK HERE for Rates & Availability
Enjoy the luxury of the grounds, outdoor kitchen, pool and waterslide, and views without the need to book the entire property. When the guest house is booked alone, no guests will be in the main house, guaranteeing your privacy and private enjoyment…
brought to you by
“VACATION HOMES OF KEY WEST”
Ultimate Key West Beach House – Sunset Key ~ VIP
12 Guests | 5 Bedrooms | 7 Bathrooms | Key West Family Beach Retreat
CLICK HERE for Rates & Availability
Perfectly positioned on Sunset Key, this exclusive waterfront estate is just 500 yards offshore from the main island of Key West. 27-acre tropical resort island. Here, you’ll find 5-star amenities including award-winning dining and a full-service luxury spa…
brought to you by
“VACATION HOMES OF KEY WEST”
Admirals Gold – Private Key West Luxury Villa
8 Guests | 4 Bedrooms | 3.5 Bathrooms | 3 Story Family Pool Home
CLICK HERE for Rates & Availability
Welcome to Admirals Gold, a luxurious weekly vacation rental nestled in the prestigious Truman Annex neighborhood. This 4-bedroom, 3.5-bathroom home is the perfect destination for those seeking a spacious and luxurious escape for the entire family…
brought to you by
“VACATION HOMES OF KEY WEST”