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...
Maryann's Place
2 Guests | Studio | 1 Bathrooms | Studio Cottage
Starting at $7788 per Month
This colorful, cheerful studio is located in the lively Casa Marina neighborhood of Key West, just a short walk from the White Street Pier and the beach. The property is surrounded by lush gardens and a private walkway, creating an energetic and fun atmosphere…
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Conch Cottage
2 Guests | 1 Bedrooms | 1 Bathrooms | Cottage in Heart of Old Town
Starting at $465 per Night
In the heart of Old Town with traditional architecture, this home serves as a perfect luxury and vacation. This home is exactly what you would imagine! From the gingerbread features to the porch seating area and colorful paint…
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Secret Casita
4 Guests | 2 Bedrooms | 2 Bathrooms | Pet Friendly Apartment
Starting at $4596 per Month
This hidden gem is a wonderful way to embrace the Key West laid-back lifestyle. This first-floor apartment is your secret gateway to relaxation. You will feel as if you have found a special piece of paradise…
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Hidden Gem
6 Guests | 3 Bedrooms | 2 Bathrooms | Old Town Pool Home
Starting at $11,801 per Month
Stroll down Higgs Lane to arrive at your Old Town Key West vacation home. Unpack and unwind at this Gem of a house which has 3 Bedrooms(2 kings/1 full) and 2 baths. This home has a refreshing soaker pool…
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Caroline On My Mind
4 Guests | 2 Bedrooms | 2 Bathrooms | Beautifully Restored Home
Starting at $10,061 per Month
This beautifully restored, remodeled second-floor 1933 Key West home on Caroline Street offers a unique and inviting experience. The location is highlighted as a key factor, emphasizing the significance of its surroundings…
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Corazon
4 Guests | 2 Bedrooms | 2.5 Bathrooms | Old Town Pool Home
Starting at $9927 per Month
Welcome to Corazon, a stunning 2-bedroom vacation rental in the heart of Key West's Old Town neighborhood. With its open floor plan, fully equipped kitchen, and private pool steps from the living area, this is the perfect home for entertaining and relaxation…
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Inn Cogneato Cottage - Monthly Rental
4 Guests | 2 Bedrooms | 2 Bathrooms | Beautiful Pool Home
Please Call for Best Rates: 305.296.1010, Opt 1
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
Starting at $4732 per Month
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
Starting at $439 per Night
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
Starting at $1098 per Night
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
Starting at $3360 per Night
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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Miss Sunshine-Monthly Rental
6 Guests | 3 Bedrooms | 3.5 Bathrooms | 2 Story Pool Home
Starting at $8135 per Month
You will find serenity in this lustrous, two-story, updated home. As you enter this attractive space, you will immediately feel its peaceful vibe. Built with an abundance of windows, sunshine envelopes this happy place…
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Tree Tops
4 Guests | 2 Bedrooms | 1 Bathrooms | Down Home Island Suite
Starting at $475 per Night
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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A Tropical Tradition (Gallup Arms)
6 Guests | 3 Bedrooms | 2.5 Bathrooms | 3 Story Key West Town Home w/ Pool
Starting at $600 per Night
Nestled in one of Key West's original gated “mini-compounds,” the Tropical Tradition vacation rental is a spacious 1990's 3 story Key West town home providing an island living experience in a traditional tropical style-both inside and out…
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Tropical ~ Tranquility
8 Guests | 4 Bedrooms | 3.5 Bathrooms | Secluded Tranquil Villa w/ Pool
Starting at $925 per Night
Tropical ~ Tranquility vacation rental is a special slice of Key West you would never find on your own. While most of the colorful cottages along this charming Old Town lane face right up to the curb…
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The Caroline House Estate
10 Guests | 5 Bedrooms | 3.5 Bathrooms | Classic Key West Estate w/ Pool
Starting at $1250 per Night
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
Starting at $875 per Night
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
Starting at $294 per Night
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…
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Sunrise Suite 203
6 Guests | 2 Bedrooms | 2.5 Bathrooms | Private Condo
Starting at $200 per Night
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
Starting at $167 per Night
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…
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La Casa de Luces
6 Guests | 2 Bedrooms | 2 Bathrooms | Private Pool Home
Starting at $267 per Night
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
Starting at $512 per Night
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
Starting at $395 per Night
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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Booty Caye
4 Guests | 2 Bedrooms | 1.5 Bathrooms | Golf Villa
Starting at $7858 per Month
Nestled within the exclusive enclave of the Key West Golf Club. This beautifully appointed 2-bedroom, 1.5-bath condominium offers a lively retreat for those seeking a longer stay amidst the lush landscapes of a golfer's paradise…
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Gumbo Limbo Cottage
4 Guests | 2 Bedrooms | 2.5 Bathrooms | Charming Key West Cottage
Starting at $7137 per Month
Escape to the laid-back charm of Key West with The Gumbo Limbo Cottage, a beautiful and beachy vacation rental. Nestled in the heart of the island, this charming 1933 shotgun house has been impeccably restored and uniquely decorated…
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Ashe Street Serenade
6 Guests | 3 Bedrooms | 3.5 Bathrooms | Luxury Pool Home
Starting at $11,852 per Month
Welcome to your dream getaway in the charming Old Town Key West, where the tranquility of island living meets the excitement of tropical adventures. Enchanting 3 bedroom, 3.5 bathroom monthly vacation rental…
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Island Pearls
4 Guests | 2 Bedrooms | 2.5 Bathrooms | Luxury Pool Home
Starting at $12,397 per Month
An embodiment of sophistication and luxury in the heart of Key West on Fleming Street. This top-tier, 2-bedroom, 2-bathroom vacation rental is poised a mere whisper away(1 Block) from the lively Duval Street…
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Love is in the Air
7 Guests | 3 Bedrooms | 2.5 Bathrooms | Luxury Pool Home
Starting at $11,248 per Month
Enjoy a month-long stay or longer in this beautiful Three-bedroom Key West Home. Hidden in the heart of Old-Town Key West, ‘Love Is in the Air’ on Love Lane is off the beaten path affording the guest privacy and relaxation…
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Mulligan's Place
6 Guests | 3 Bedrooms | 2 Bathrooms | Tropical Charmer
Starting at $9315 per Month
This pleasant, bright and spacious townhome comes with a large backyard space for entertaining or just lounging around and is located on a quiet cul de sac. This townhome has a wide front porch with two, large screened-in and covered porches for your relaxation…
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My Happy Place-Monthly Rental
4 Guests | 2 Bedrooms | 2 Bathrooms | Quaint Home with Dip Pool
Starting at $6578 per Month
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
Starting at $511 per Night
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
Starting at $343 per Night
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
Starting at $343 per Night
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
Starting at $535 per Night
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
Starting at $1084 per Night
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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Dancing Palms Villa
4 Guests | 2 Bedrooms | 2 Bathrooms | Historic Key West Vacation Home
Starting at $450 per Night
Nestled in the small exclusive gated Windward Park, this renovated home sits in the back with lots of privacy. It has the architectural allure of a historic design, with all the advantages of a modern interior layout and luxury amenities…
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Caribbean Cottage ~ Duval Street Key West
5 Guests | 2 Bedrooms | 2 Bathrooms | Historic Duval Street Vacation Home
Starting at $550 per Night
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
Starting at $1657 per Night
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
Starting at $950 per Night
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
Starting at $571.50 per Night
By The Beautiful Sea, you can instantly gratify this need for sensational vistas from your own vacation rental terrace right across the street from the beach. Ahhhh . . . life in paradise is good…
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Key West Mile Zero Suite
4 Guests | 2 Bedrooms | 2 Bathrooms | Charming Island Suite
Starting at $564.50 per Night
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
Starting at $260 per Night
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
Starting at $341 per Night
Escape the stress and cares of your daily life with a vacation to the wonderful Cuban Paradise! 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
Starting at $324 per Night
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
Starting at $308 per Night
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
Starting at $300 per Night
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
Starting at $6334 per Month
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
Starting at $12,474 per Month
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
Starting at $7897 per Month
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
Starting at $2517 per Week
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
Starting at $4380 per Week
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
Starting at $975 per Night
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
Starting at $4100 per Month
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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Family Reunion
28 Guests | 12 Bedrooms | 8.5 Bathrooms | 3 Homes for Events
Starting at $2210 per Night
Family Reunion Key West vacation rental includes: The Flower Power House, a 2-story house with attached cottage suite, plus two 3-story town homes – A Tropical Tradition and Coco's Poolside Retreat…
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Sunset Serenade
6 Guests | 2 Bedrooms | 2.5 Bathrooms | Luxury Villa
Starting at $9500 per Month
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
Starting at $20,700 per Month
Everyone dreams of a private island beach house with an epic view from the pool to the beach. This 3 BR 4 BA Private Island Key West Beach House – Sunset Key ~ VIP, is all those things and more…
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Island Cosmopolitan Cottage
6 Guests | 3 Bedrooms | 2 Bathrooms | Luxury Key West Cottage
Starting at $7600 per Month
Tucked behind an alluring tall white-picket fence, this elegantly renovated Island Cosmopolitan Cottage reflects an upscale blend of contemporary with historic architectural design…
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A Bit of Heaven
6 Guests | 3 Bedrooms | 3 Bathrooms | Pool Home in Historic District
Starting at $200 per Night
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
Starting at $232 per Night
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
Starting at $190 per Night
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
Starting at $262 per Night
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
Starting at $293 per Night
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
Starting at $386 per Night
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
Starting at $299 per Night
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
Starting at $308 per Night
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
Starting at $451 per Night
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
Starting at $740 per Night
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
Starting at $10,322 per Month
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
Starting at $6285 per Month
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
Starting at $475 per Night
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…
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Flower Power House
15 Guests | 6 Bedrooms | 4 Bathrooms | Luxury Vacation Home
Starting at $1250 per Night
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…
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Key West Island Village Cottage
6 Guests | 2 Bedrooms | 1.5 Bathrooms | Luxury Cottage
Starting at $4700 per Month
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…
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“VACATION HOMES OF KEY WEST”
The Grand Marshall House
10 Guests | 4 Bedrooms | 3 Bathrooms | Luxury Historic Estate
Starting at $14,400 per Month
The historic gingerbread exterior was completely restored, a pool and in-ground Jacuzzi were added in the back yard, and the interior was modernized as a masterpiece of handsome design…
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Designer Octagon House of Key West
8 Guests | 4 Bedrooms | 4 Bathrooms | Luxury Vacation Home
Starting at $22,000 per Month
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
Starting at $21,000 per Month
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
Starting at $250 per Night (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
Starting at $325 per Night
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
Starting at $124 per Night
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
Starting at $197 per Night (monthly rental)
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! THIS IS A MONTHLY RENTAL…
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Aloha
10 Guests | 4 Bedrooms | 4 Bathrooms | Pet Friendly Pool Home
Starting at $300 per Night (monthly rental)
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
Starting at $14,032 per Month
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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“HISTORIC KEY WEST VACATION RENTALS”
Tropical Dream - Monthly Rental
8 Guests | 4 Bedrooms | 4.5 Bathrooms | Luxury Pool Home
Starting at $9465 per Month
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
Starting at $7346 per Month
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
Starting at $2036 per Night
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 Luxe - Nightly Rental
7 Guests | 3 Bedrooms | 3.5 Bathrooms | Stunning Pool Home
Starting at $1218 per Night
Villa Luxe has a sexy vibe that can be felt inside and out. Imagine fashion models lounging poolside? Well, you can too! This ‘Adults Only’ property is however not suitable for children under the age of 12 years…
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Villa Corazon
8 Guests | 3 Bedrooms | 4 Bathrooms | Luxury Vacation Home
Starting at $8000 per Month
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
Starting at $4950 per Month
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
Starting at $2300 per Night
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
Starting at $4725 per Month
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
Starting at $6900 per Month
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
Starting at $6000 per Month
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
Starting at $6200 per Month
This luxury townhome vacation rental stands on a serene street, in a tiny, gated enclave called Key West Porter Court. A bit of a secret, it’s nicely hidden within the stunning neighborhood of Truman Annex…
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Debonair Victorian Estate
10 Guests | 5 Bedrooms | 5 Bathrooms | Luxury Victorian Estate
Starting at $17,000 per Month
Located in the Historic Seaport neighborhood of Old Town Key West, the curb-side view of this 1900’s wooden Victorian displays treasured traditional characteristics. But inside and poolside, it offers all the luxurious amenities of an upscale modern home…
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Mediterranean Caribbean Villa
6 Guests | 3 Bedrooms | 2.5 Bathrooms | Garden Cottage with Pool
Starting at $7200 per Month
Located along one of Key West's most desirable residential streets this “Casa el Paradiso” most certainly offers a private slice of paradise complete with mature native tropical gardens, Mediterranean style courtyards, and free form swimming pool…
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Casa Bella Petite le Bleu
4 Guests | 2 Bedrooms | 2 Bathrooms | Charming Cottage with Pool
Starting at $5500 per Month
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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