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 luxury vacation rentals for tropical villas, beach condos, secluded cabins. Don’t forget about our exciting All Inclusive Packages, Wedding Destinations, Resort Vacation Packages, Family Vacations 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.
FLORIDA KEYS VACATIONS
KEY WEST PROPERTIES...
Ashe House - Monthly Rental
Sleeps 6 | 3 Bedrooms | 3.5 Bathrooms | Historic Vacation Home
Starting at $8433 per Month
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
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 …
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“THE CONCH HOUSE HERITAGE INN”
SUNSET HARMONY
Sleep 4 | 2 Bedrooms | 2 Bathrooms | Luxury Waterfront Vacation Home
Starting at $4400 per Month
Sunset Harmony is exactly that! A gorgeous home on open water with spectacular views of the sunset over lower Sugarloaf Key. With just 14 miles to Key West, you are only a short ride away from all the fun and attractions the southernmost city has to offer…
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“ACTION KEYS REALTY”
Vintage Luxury Cottage On Duval
4 Guests | 1 Bedrooms | 1 Bathrooms | Cottage with Private Heated Pool
Starting at $546 per Night
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 …
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“VACATION HOMES OF KEY WEST”
The Green Goddess
8 Guests | 4 Bedrooms | 3 Bathrooms | Secluded Peaceful Vacation Home
Starting at $9595 per Month
Experience the beauty of Key West's famous sunsets from the comfort of your own vacation home at The Green Goddess. This secluded and peaceful property is located just off Whitehead Street, less than a block from the Southernmost Point…
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Mango Cottage
6 Guests | 2 Bedrooms | 2 Bathrooms | Cottage with Private Saltwater Pool
Starting at $396 per Night
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…
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“RENT KEY WEST”
Havana Lane
4 Guests | 2 Bedrooms | 2 Bathrooms | Pet Friendly Cottage with Pool
Starting at $1000 per Night
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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“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…
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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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“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…
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“HISTORIC KEY WEST VACATION RENTALS”
Bahari House - Monthly Rental
Sleeps 6 | 2 Bedrooms | 3 Bathrooms | Vacation Home in Old Town
Starting at $9450 per Month
Walk to the harbor from this 2-bedroom, 3 full bath home in Old Town. From its white picket fence and second story balcony to its Dade County pine walls and covered patio, this home will have you feeling like a local in no time…
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“HISTORIC KEY WEST VACATION RENTALS”
Bohemian House - Monthly Rental
Sleeps 4 | 2 Bedrooms | 2 Bathrooms | Historic Vacation Home
Starting at $5902 per Month
The Bohemian House is a restored treasure full of delightful surprises. Its front porch is perfect for people watching or casting your cares away on the swing. As you enter the home you will be enveloped in the beauty of its coveted Dade County Pine…
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“HISTORIC KEY WEST VACATION RENTALS”
Key West Sunset Sojourn
6 Guests | 3 Bedrooms | 4 Bathrooms | Dream Home on Private Island
Starting at $18,000 per Month
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 …
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“VACATION HOMES OF KEY WEST”
Private Pool Garden Villa
6 Guests | 3 Bedrooms | 2.5 Bathrooms | Private Garden Oasis Home
Starting at $800.75 per Night
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…
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Havana Moon Over Duval
6 Guests | 2 Bedrooms | 2 Bathrooms | Cottage on Upper Duval Street
Starting at $575 per Night
Originally built in the late 1800's as a cigar makers' cottage the authentic exterior of this turn-of-the-century cottage is protected by historic preservation rules and today stands renovated to form…
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“VACATION HOMES OF KEY WEST”
The Green Goddess
8 Guests | 4 Bedrooms | 3 Bathrooms | Secluded Peaceful Vacation Home
Starting at $9595 per Month
Experience the beauty of Key West's famous sunsets from the comfort of your own vacation home at The Green Goddess. This secluded and peaceful property is located just off Whitehead Street, less than a block from the Southernmost Point…
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Tranquility
6 Guests | 3 Bedrooms | 3 Bathrooms | Luxury Pool Home
Starting at $10,432 per Month
Welcome to Tranquility, a luxurious vacation rental nestled in a tropical setting. This stunning 3 bedroom, 3 bathroom home is the perfect escape for those seeking peace and relaxation. Just seven blocks from the “Famous” Duval Street…
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Colony Poolside
2 Guests | 1 Bedrooms | 1 Bathrooms | Bungalow in Historic Old Town
Starting at $208 per Night
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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“RENT KEY WEST”
Casa Amor
8 Guests | 3 Bedrooms | 3.5 Bathrooms | Modern Pool Home
Starting at $700 per Night
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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“RENT KEY WEST”
Casa Loca
8 Guests | 3 Bedrooms | 2.5 Bathrooms | Modern Pool Home
Starting at $800 per Night
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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Heavenly Hideaway
6 Guests | 3 Bedrooms | 1.5 Bathrooms | Luxury Pool Home
Starting at $11,070 per Month
Welcome to our Heavenly Hideaway, a serene oasis nestled in the heart of Key West. This enchanting 3-bedroom, 1.5-bath property comfortably sleeps 6, offering a divine blend of comfort and convenience…
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Thirsty Mermaid
8 Guests | 4 Bedrooms | 3 Bathrooms | Luxury Pool Home
Starting at $10,220 per Month
Thirsty Mermaid is located in the Casa Marina area just minutes from the Atlantic Ocean.
This beautiful property has 2 floors. Walk into the front door, and you will be greeted with a bright and spacious living room that also contains a wet bar…
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Tropical Jewel
6 Guests | 2 Bedrooms | 2 Bathrooms | Pool Home in Downtown
Please Call for Best Rates: 305-294-3040
Discover the eclectic charm of this Key West home, just two blocks from the Historic Seaport. This unique property is a perfect blend of colorful, quirky elements that embody the spirit of island living…
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Butterfly Cottage - Nightly Rental
Sleeps 4 | 2 Bedrooms | 2.5 Bathrooms | Cozy Cottage on Quiet Lane
Starting at $575 per Night
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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“HISTORIC KEY WEST VACATION RENTALS”
Casablanca - Nightly Rental
Sleeps 4 | 1 Bedrooms | 1 Bathrooms | Pet Friendly Pool Home
Starting at $500 per Night
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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“HISTORIC KEY WEST VACATION RENTALS”
Casablanca Too - Nightly Rental
Sleeps 2 | 1 Bedrooms | 1 Bathrooms | Pet Friendly Pool Home
Starting at $467 per Night
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
Starting at $577 per Night
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
Please Call for Best Rates: 305-296-1010 Option 1
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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Heavenly Hideout at Rainbow's End
8 Guests | 4 Bedrooms | 4 Bathrooms | Tropical Style Penthouse Vacation Rental
Starting at $925 per Night
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…
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“VACATION HOMES OF KEY WEST”
Garden Suite
6 Guests | 2 Bedrooms | 2 Bathrooms | Boho Style Poolside Garden Suite
Starting at $550 per Night
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…
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Coco's Poolside Retreat
8 Guests | 3 Bedrooms | 2.5 Bathrooms | 3 Story Townhome
Starting at $550 per Night
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…
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Key West Dreamin'
6 Guests | 2 Bedrooms | 2 Bathrooms | Private Historic Vacation Home
Starting at $625 per Night
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…
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“VACATION HOMES OF KEY WEST”
Casa Loca
4 Guests | 2 Bedrooms | 2 Bathrooms | Key West Style Cottage
Starting at $500 per Night
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
Starting at $623 per Night
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
Starting at $357 per Night
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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“RENT KEY WEST”
Pilars Secret
8 Guests | 3 Bedrooms | 2 Bathrooms | Old Town Pool Home
Starting at $763 per Night
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…
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MANSION @ The Watson House
14 Guests | 7 Bedrooms | 7 Bathrooms | 3 Story Victorian Mansion
Starting at $1198 per Night
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…
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Amanda's Dream Suites
10 Guests | 4 Bedrooms | 3 Bathrooms | Charming Historic Vacation Home
Starting at $1019.25 per Night
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…
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“VACATION HOMES OF KEY WEST”
Governor's Retreat
4 Guests | 2 Bedrooms | 2 Bathrooms | Luxury Vacation Rental Cottage
Starting at $7900 per Month
This gentle Governor's Retreat in the Key West Meadows is an immaculate luxury vacation rental cottage in an elegant and very quiet garden setting for those with discerning tastes…
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Seaport Treasure Estate
12 Guests | 6 Bedrooms | 6.5 Bathrooms | Luxury Vacation Rental Estate
Starting at $19,000 per Month
While you won’t need a treasure map to find this luxury vacation rental estate, you’ll know you’ve discovered a rare island gem from the moment you walk through the private gates…
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Breezy Retreat
4 Guests | 2 Bedrooms | 2 Bathrooms | Townhome in Gated Community
Starting at $2710 per Week
The Breezy Retreat is situated in the Windward Park gated community, offering a convenient location within walking distance to the Historic Southernmost Point and one block away from the famous Duval Street, known for its vibrant atmosphere and attractions…
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Lavender on White
6 Guests | 3 Bedrooms | 2.5 Bathrooms | Pool Home in Heart of Key West
Starting at $8925 per Month
Nestled in a prime location, Lavender on White offers the perfect blend of tranquility and accessibility. Situated in the heart of Key West, this charming haven is conveniently located just a 10-minute stroll away from the vibrant energy of Duval Street…
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Sweet Tee
4 Guests | 2 Bedrooms | 1.5 Bathrooms | Quaint Home with Shared Pool
Starting at $6252 per Month
As you make your way into The Sweet Tee, an immediate sense of relaxation and vacation mode envelops you. The carefully chosen soft muted colors and decor create an inviting ambiance that sets the stage for a tranquil getaway…
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Golf Villa
4 Guests | 2 Bedrooms | 2 Bathrooms | Villa in Golf Neighborhood
Starting at $4957 per Month
Your perfect Key West getaway in the highly sought-after Key West Golf Club neighborhood! Immerse yourself in the island lifestyle in this charming and well-maintained bungalow with 2spacious bedrooms and 2 en suite bathrooms…
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Peachy Keen
7 Guests | 4 Bedrooms | 3.5 Bathrooms | Private Heated Pool
Starting at $11,397 per Month
This beautiful home has 3 bedrooms and 3 baths in the main house with a bonus cabana. There is a private and heated pool, a separate entrance for one of the bedrooms, and a pool cabana that houses the 4th bedroom…
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Chavez House - Nightly Rental
Sleeps 6 | 3 Bedrooms | 2 Bathrooms | Pet Friendly Pool Home
Starting at $1138 per Night
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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“HISTORIC KEY WEST VACATION RENTALS”
Chick-a-Pea Cottage - Nightly Rental
Sleeps 8 | 4 Bedrooms | 2.5 Bathrooms | Pet Friendly Pool Home
Starting at $1051 per Night
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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“HISTORIC KEY WEST VACATION RENTALS”
Cloud 9 - Nightly Rental
Sleeps 7 | 3 Bedrooms | 3 Bathrooms | Luxury Pool Home
Starting at $1444 per Night
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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Elegant Key West Tree House
4 Guests | 2 Bedrooms | 1 Bathrooms | Quaint Old Town Vacation Rental
Starting at $4500 per Month
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…
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Belle Maison du Port
6 Guests | 3 Bedrooms | 3.5 Bathrooms | 2 Story Victorian Vacation Home
Starting at $15,500 per Month
This extraordinary French Caribbean style home, Belle Maison du Port (Fine Harbor House), is available as a monthly vacation rental from May through October. Comprised of a stunningly renovated 2 – Story Victorian home…
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Island Interlude
4 Guests | 2 Bedrooms | 2.5 Bathrooms | Luxurious 2 Story Town Home
Starting at $4800 per Month
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…
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Tropical Chill
4 Guests | 2 Bedrooms | 2 Bathrooms | 2 Story Cottage Style Flat
Starting at $449.50 per Night
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…
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Ocean View Luxury Villa
8 Guests | 3 Bedrooms | 4 Bathrooms | Ocean View Luxury Vacation Home
Starting at $8185 per Week
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…
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Tropical Cottage @ Tropical Village
6 Guests | 2 Bedrooms | 2 Bathrooms | Pet Friendly Cottage
Starting at $314 per Night
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
Starting at $425 per Night
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
Starting at $650 per Night
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
Starting at $750 per Night
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
Starting at $414 per Night
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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Casita in the Cloud
4 Guests | 2 Bedrooms | 2 Bathrooms | 3 Story Apartment in Dowtown
Starting at $5187 per Month
WELCOME TO CASITA IN THE CLOUD! Your search for the perfect island getaway has ended! This large 3 story, two bedrooms, two bath apartment boasts all the amenities you’d expect from your island home…
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Little Casita
2 Guests | 1 Bedrooms | 1 Bathrooms | Historic Apartment in Downtown
Starting at $3493 per Month
If looking for the perfect couple’s retreat, look no further! This one bedroom, one bath historic apartment is located just blocks from Key West’s famous Duval Street & Historic Seaport where you’ll find restaurants, shops, and bars…
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Casa Verde
6 Guests | 3 Bedrooms | 3.5 Bathrooms | Heated Pool & Hot Tub
Starting at $9385 per Month
The moment you walk thru the door you are greeted by soothing tropical colors and high vaulted ceilings. All the sliding doors open up to the Waterfall pool so you can extend your party outside and enjoy the heated pool and spa…
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Petite Pearl
2 Guests | 1 Bedrooms | 1 Bathrooms | Shared Heated Pool
Starting at $9385 per Month
Welcome to Petite Pearl, your hidden gem nestled in the heart of the coveted Meadows district in Key West. A stone's throw away from the pulsating rhythm of Duval Street and the island's most mesmerizing beaches…
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Island Time
12 Guests | 5 Bedrooms | 3 Bathrooms | Family Pool Home
Starting at $15,932 per Month
Key West Island Time is a rare find in old town Key West. It is a total of 5 bedrooms and three bathrooms in 2 separate cottages with full amenities that has just been renovated and tastefully updated…
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Four Palms
8 Guests | 3 Bedrooms | 4.5 Bathrooms | 2 Story Pool Home
Please Call for Best Rates: 305-294-3040
Welcome to Four Palms, a luxurious 2-story home located in the prestigious neighborhood of Casa Marina, Key West. This idyllic location offers an abundance of opulent amenities, including gated parking, a private pool, and a guest cottage…
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Copa Cabana - Monthly Rental
Sleeps 4 | 2 Bedrooms | 2 Bathrooms | Quaint Pool Home
Starting at $5350 per Month
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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“HISTORIC KEY WEST VACATION RENTALS”
Dreaming on Duval - Nightly Rental
Sleeps 10 | 5 Bedrooms | 4.5 Bathrooms | Spacious Pool Home
Starting at $1365 per Night
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
Starting at $2694 per Week
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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Sweet Sunshine Garden Flat
4 Guests | 2 Bedrooms | 1 Bathrooms | Caribbean Cottage-style flat by the beach
Starting at $1800 per Week
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…
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Hidden Story-Book Cottage
2 Guests | 1 Bedrooms | 1 Bathrooms | Luxury Cottage in Old Town Key West
Starting at $3700 per Month
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…
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Island Elegance
6 Guests | 3 Bedrooms | 3 Bathrooms | Luxury Corner Lot Vacation Home
Starting at $6350 per Month
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…
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Classic Key West Estate
14 Guests | 7 Bedrooms | 5.5 Bathrooms | Grand Historic Key West Pool Home
Starting at $1700 per Night
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…
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Butterfly Garden
2 Guests | 1 Bedrooms | 1 Bathrooms | Romantic Garden Villa
Starting at $3900 per Month
Completely hidden from the street, this authentic Butterfly Garden Flat, provides you with two private entrances off a large gated manicured garden. Your own private expansive covered bricked front porch…
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Truman Treasure
5 Guests | 3 Bedrooms | 2 Bathrooms | 2 Story Truman Annex Vacation Rental
Starting at $5267 per Week
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…
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Fleming-O
6 Guests | 2 Bedrooms | 1 Bathrooms | Cottage in Historic Old Town
Starting at $225 per Night
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
Starting at $714 per Night
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
Starting at $777 per Night
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
Starting at $850 per Night
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
Starting at $850 per Night
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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Foundry 7
5 Guests | 2 Bedrooms | 2.5 Bathrooms | 3 Story Townhome
Starting at $9079 per Month
Escape to the historic and luxurious neighborhood of Truman Annex in Key West, where you'll find Foundry 7 – a unique 3-story townhome built on the grounds of the former Fort Zachary Military Base…
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Sea La Vie
6 Guests | 3 Bedrooms | 3 Bathrooms | Oceanfront Beach House
Starting at $7190 per Month
Welcome to Sea La Vie, an elevated oceanfront paradise available for rent. Nestled in the picturesque Cudjoe Bay, this 3 bedroom, 3 bathroom home offers unparalleled views of the Atlantic that will take your breath away…
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Pineapple Cottage
5 Guests | 2 Bedrooms | 2 Bathrooms | Old Town Key West
Starting at $3784 per Week
The Pineapple Cottage is a charming two-bedroom, two-bathroom home located in Old Town Key West. It offers a private pool and is just half a block away from Duval Street, making it an ideal tropical oasis for your vacation…
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Shady Palms
6 Guests | 2 Bedrooms | 2.5 Bathrooms | Family Pool Home
Starting at $6883 per Week
Step into this beautifully restored and redecorated 1933 Key West home. This first-floor home has Bahama shutters throughout the house to open up and let in the Key West sun. The backyard has its own private pool…
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Jasmine Place
4 Guests | 2 Bedrooms | 2 Bathrooms | Historic Pool Home
Starting at $668 per Night
Jasmine Place is a beautiful and enchanting home located next door to the Ernest Hemingway Home and Museum. Across the street from the Key West Lighthouse. The backyard is landscaped with a tropical, local plants with deck and private pool…
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Grand Maison - Nightly Rental
Sleeps 8 | 4 Bedrooms | 4.5 Bathrooms | Historic Pool Home
Starting at $2302 per Night
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
Starting at $366 per Night
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
Starting at $366 per Night
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
Starting at $652 per Night
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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Queen Conch - Nightly Rental
Sleeps 14 | 4 Bedrooms | 4 Bathrooms | Spacious Pool Home
Starting at $1170 per Night
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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Island Brownstone
6 Guests | 2 Bedrooms | 2.5 Bathrooms | Tri-Level Historic Brownstone
Starting at $2600 per Week
An exclusive island style brownstone perfectly nestled in Key West’s most prominent gated waterfront neighborhood known as ‘Truman Annex’, this striking tri-level historic building…
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Down Island Digs
6 Guests | 2 Bedrooms | 2 Bathrooms | Private Garden Cottage
Starting at $575 per Night
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…
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Pavilion Villa
10 Guests | 4 Bedrooms | 3 Bathrooms | Prestigious Garden Home in Old Town
Starting at $975 per Night
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…
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Exclusive Key West Beach Front
6 Guests | 2 Bedrooms | 3 Bathrooms | Designer Oceanfront Luxury Condo Rental
Starting at $2700 per week
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…
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Duval Street Fantasy Resort Villa
8 Guests | 3 Bedrooms | 3 Bathrooms | Charming Cottage with Pool
Starting at $1164 per Night
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…
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Twice as Nice on Duval Street
8 Guests | 4 Bedrooms | 4 Bathrooms | Twin-Cigar Maker's Cottages
Starting at $906.25 per Night
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 …
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Royal Poinciana Cottage @ Conch Cottages
2 Guests | 1 Bedrooms | 1 Bathrooms | Beautiful Studio Cottage
Starting at $241 per Night
Royal Poinciana is a studio cottage with a queen bed, kitchen ,and private bath. The queen bed sleeps 2 people and the kitchen is fully equipped with refrigerator, microwave, toaster. and coffee maker…
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A Slice of Paradise -Shipyard Palms
4 Guests | 2 Bedrooms | 1.5 Bathrooms | Condo in Gated Community
Starting at $300 per Night
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
Starting at $269 per Night
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
Starting at $785 per Night
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
Starting at $230 per Night
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
Starting at $208 per Night
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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