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.
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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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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 PROPERTIES...
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
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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
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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
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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
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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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Tree Tops
4 Guests | 2 Bedrooms | 1 Bathrooms | Down Home Island Suite
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The Tree Tops Suite vacation rental is has a classic undying Key West bohemian charm that exudes a real down-island vacation feel that I love. Nestled in the tree tops it gives off the feeling of part ‘tree house’ and part old fashioned lodge…
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Tropical ~ Tranquility
8 Guests | 4 Bedrooms | 3.5 Bathrooms | Secluded Tranquil Villa w/ Pool
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Few places exist where you can ride the fine line separating a secluded tranquil luxury villa, and the Heart of Old Town Key West. This vacation rental is a special slice of Key West you would never find on your own. Trickling waterfall that gently spills to the pool…
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The Caroline House Estate
10 Guests | 5 Bedrooms | 3.5 Bathrooms | Classic Key West Estate w/ Pool
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The Caroline House Estate vacation rental is comprised of two dwellings – a classic 2-story Key West Victorian house, and a hidden 1 ½ story Caribbean bungalow. Located in Key West’s famous Old Town Historic Seaport neighborhood…
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Key West Wabi Sabi
8 Guests | 4 Bedrooms | 3.5 Bathrooms | Authentic Key West Cottage
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Undeniably adorable, Key West Wabi Sabi vacation rental is a celebration of authentic Key West cottage style island living. Built in 1930, the front of the historic wooden plank house is held to vintage form with loads of original details…
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Paradise on Porter
4 Guests | 2 Bedrooms | 2.5 Bathrooms | Townhome with Pool
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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
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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
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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
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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
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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
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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
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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
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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
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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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Caribbean Cottage ~ Duval Street Key West
5 Guests | 2 Bedrooms | 2 Bathrooms | Historic Duval Street Vacation Home
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Brimming with genuine island charm, our Caribbean Cottage, with private pool, was originally built in the early 1900’s. Artistically renovated to maintain the original wood planked polished floors and vintage hand-hewed beams…
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Island Rendezvous
12 Guests | 6 Bedrooms | 5 Bathrooms | Vacation Pool Home in Old Town
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Island Rendezvous offers the perfect solution for a gathering of family or friends who desire to be in the heart of Old Town Key West. Here you will enjoy a completely private retreat with an atmosphere of wonderfully unchanged Caribbean charm…
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Villa Deja vu Key West
10 Guests | 4 Bedrooms | 3 Bathrooms | Vacation Pool Home in Upper Duval
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Villa Déjà vu Key West is ideal for family, groups or friends. The floor plan provides 2 spacious separate floors which are adjoined with a covered indoor/outdoor staircase, with a large indoor living room, and pool garden with large deck for all to gather…
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By The Beautiful Sea
6 Guests | 3 Bedrooms | 2 Bathrooms | Key West Beachfront Condo Rental
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If you’re craving a Key West beach front accommodation with a bona fide front-line view to the sea, you know that Key West beach front rentals not easy to come by. By The Beautiful Sea, you can instantly gratify this need for sensational vistas . . . life in paradise is good…
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Key West Mile Zero Suite
4 Guests | 2 Bedrooms | 2 Bathrooms | Charming Island Suite
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When taking a selfie at the iconic Key West Mile Marker 0 isn’t enough, now you can luxuriously live right next to this landmark! This stylish 2 bedroom is discretely perched above the Mile 0 location, above the island bustle…
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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
CLICK HERE for Rates & Availability
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
CLICK HERE for Rates & Availability
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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Amelia's Hideaway
10 Guests | 4 Bedrooms | 4 Bathrooms | One-of-a-Kind Vacation Villa
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This one-of-a-kind vacation villa is perfectly situated just off Upper Duval, and it is well hidden from public view. Unless you've stayed in this villa before, there's no-way you'd ever know it's just steps off Upper Duval Street…
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Little Digs Key West
2 Guests | 1 Bedrooms | 1 Bathrooms | Historic Luxury Cottage
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Diminutive in size but huge in style, ‘Little Digs Key West,’ authenticates how ‘big things’ really do happen in small spaces. Key West was centuries ahead of its time in the modern day ‘tiny house movement…
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Sunset Serenade
6 Guests | 2 Bedrooms | 2.5 Bathrooms | Luxury Villa
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At Sunset Serenade life becomes even a little more relaxing, and evening sunsets take a different direction. Here you’re softly serenaded with the sounds of the surrounding sea and rustling fronds of the palm trees, while you chill-out on your own private rooftop deck…
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Private Island Key West Beach House
6 Guests | 3 Bedrooms | 4 Bathrooms | Luxury Beach House
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Nestled on the exclusive 27-acre Sunset Key island, the Private Island Key West Beach House offers a luxurious and serene retreat. This stately 3-bedroom, 4-bathroom residence epitomizes tropical elegance with its classic American Colonial architecture and breathtaking views…
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A Bit of Heaven
6 Guests | 3 Bedrooms | 3 Bathrooms | Pool Home in Historic District
CLICK HERE for Rates & Availability
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
CLICK HERE for Rates & Availability
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
CLICK HERE for Rates & Availability
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
CLICK HERE for Rates & Availability
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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Cockadoodle Cottage On Duval
6 Guests | 2 Bedrooms | 2 Bathrooms | Luxury Key West Cottage
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Key West cottage architecture has been thoroughly time-tested in island life and culture in this somewhat infamous little wooden cigar maker's cottage located on famous Duval Street, at the classier upper-end…
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Flower Power House
15 Guests | 6 Bedrooms | 4 Bathrooms | Luxury Vacation Home
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Boho beautiful, the free-spirited presence of the Key West Flower Power House vacation rental, has much more in common with the real Key West than the shiny hotels around town. Here, charm comes from bespoke creativity and the joy of offbeat island treasures….
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Key West Island Village Cottage
6 Guests | 2 Bedrooms | 1.5 Bathrooms | Luxury Cottage
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Ideally situated on famous Southard St., in the Historic Seaport side of Old Town, this historic Key West cottage is nestled in one of the island’s most charming and interesting residential neighborhoods. This unique home will bring you to the heart-and-soul…
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Designer Octagon House of Key West
8 Guests | 4 Bedrooms | 4 Bathrooms | Luxury Vacation Home
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Standing prominently in the sought-after Key West Historic Seaport Neighborhood, this iconic Designer Octagon House of Key West, makes a grand architectural statement. Truly a home of fine distinction…
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Bella Grand Premier Estate
10 Guests | 5 Bedrooms | 5 Bathrooms | Luxury Vacation Home
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Deluxe Old Town Key West estate with a new twist on history. Premier custom design reflects the historic neighborhood, while reinventing the Key West luxury lifestyle. Zen-garden swimming pool, trickling tiled waterfalls and a spa…
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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
CLICK HERE for Rates & Availability
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
CLICK HERE for Rates & Availability
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
CLICK HERE for Rates & Availability
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
CLICK HERE for Rates & Availability
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
CLICK HERE for Rates & Availability
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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Villa Corazon
8 Guests | 3 Bedrooms | 4 Bathrooms | Luxury Vacation Home
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There’s lots to love about the luxurious 3BR 4BA Villa Corazon … it even has a heart shaped pool. Experience ultimate resort style living in this private home retreat. A perfect pairing of a renovated Key West gingerbread cottage with an elegant free-standing cottage…
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Seaport Hideaway
4 Guests | 2 Bedrooms | 1.5 Bathrooms | Luxury 2 Story Condo
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Magic happened when this Key West wooden heritage building was redesigned. Now offers limited-edition condominiums. A case in point is this 2BR 1.5BA Seaport Hideaway. Architecturally intriguing. Epic historic atrium stairwell…
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Old Town Caribbean Estate
18-21 Guests | 10 Bedrooms | 7.5 Bathrooms | Luxury Home with Guest House
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Spacious. Luxurious. Exotic. Old Town Caribbean Estate is a masterful combination of a classic Key West Victorian home with an exotic Caribbean-style guest house. A remarkable place for family and friends to stay together in a Key West weekly rental…
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Key West Poolside Loft
4 Guests | 2 Bedrooms | 2 Bathrooms | Luxury Loft with Garden Pool View
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You know that adage … An unexpected turn can lead to hidden treasures. If there were ever a place that meets that description, it's this 2BR 2BA Key West Poolside Loft. Cleverly tucked away, here you’re in a unique loft-style Key West cottage, with a private deck…
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On Hemingway's Rounds
4 Guests | 2 Bedrooms | 2 Bathrooms | Luxury Bungalow with Pool
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On Hemingway's Rounds, is an inspired renovation of a classic circa 1920 American Bungalow redone Key West style. Private swimming pool garden and deck in the fenced back yard. Historic front porch with comfy chairs to relax and watch Key west go by…
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Rooftop Renaissance
4 Guests | 1 Bedrooms | 2 Bathrooms | Modern Victorian Condo
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Rooftop Renaissance vacation rental falls into a distinctive design category of Heritage Victorian – Meets Modern Luxury. This one-of-a-kind monthly rental is situated on two floors of one side of a grand historic home on Caroline Street. An exquisite 1BR 2BA luxury accommodation…
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Serenity Now
4 Guests | 2 Bedrooms | 2.5 Bathrooms | Luxury Townhome
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Imagine a perfect vacation in Old Town Key West, where luxury and convenience blend seamlessly. Serenity Now is a stunning 2-bedroom, 2.5-bathroom townhome available for monthly rental, offering an ideal blend of elegance and relaxation…
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Casa Bella Petite le Bleu
4 Guests | 2 Bedrooms | 2 Bathrooms | Charming Cottage with Pool
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First impressions are everything. And it’s love at first sight with the charming 2BR 2BA Casa Bella Petite le Bleu. This classic Key West cigar-maker's cottage was originally built in 1889, on a lazy little narrow lane. Luxurious charming pool-garden home…
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The Blue Llama Estate Compound
14 Guests | 7 Bedrooms | 7.5 Bathrooms | Luxury Pool Estate
Starting at $29,000 per Month
Designed for luxurious living, the 7BR 7.5BA Blue Llama Estate, is the perfect Old Town Key West place to settle in and have a great time for a month or more. This spacious property is Ideal for extended families or a group of friends…
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“VACATION HOMES OF KEY WEST”