FLORIDA KEYS
KEY WEST LUXURY VACATIONS
Key West Luxury Vacations – Finest Luxury Vacations offers you a variety of hand selected Key West Vacation Rentals. Our Featured Provider: VACATION HOMES OF KEY WEST. Vacation Homes of Key West is well established as a premier vacation rental management company. We continue to offer what our founder envisioned as, “authentic Key West vacation rentals, where you can really live your Key West vacation island style.”
VHKW lives and breathes Key West. We love our island and sharing it with the world. We’re committed to remaining a family business, focused solely on Key West, and holding onto Key West’s true character and charm. Access the Best of Key West! Find an amazing Key West Vacation Rentals with “Vacation Homes of Key West”.
Book Direct and Save Money with VHKW. Booking your Key West Vacation through our website eliminates the fees from 3rd party travel agents.
EXPERIENCE KEY WEST..
OUR KEY WEST PROPERTIES...
Ultimate Key West Beach House
12 Guests | 5 Bedrooms | 7 Bathrooms
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Sunset Key ~ VIP – Perfectly positioned on Sunset Key, this exclusive waterfront estate is just 500 yards offshore from the main island of Key West…
Family Reunion Compound
21 Guests | 8 Bedrooms | 6.5 Bathrooms
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Flower Power House + Coco’s Poolside Retreat – This one-of-kind gated Key West vacation rental compound is the perfect place for family reunion in Authentic Old Town Key West…
The Blue Llama Estate Compound
14 Guests | 7 Bedrooms | 7.5 Bathrooms
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Designed for luxurious living, s the perfect Old Town Key West place to settle in and have a great time for a month or more…
Island Rendezvous
14 Guests | 6 Bedrooms | 5 Bathrooms
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Here you will enjoy a completely private retreat with an atmosphere of wonderfully unchanged Caribbean charm. 2 private swimming pools, two sun decks, a roof top deck…
The Green Hour
10 Guests | 5 Bedrooms | 5 Bathrooms
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Set behind a gate on a quiet residential street in Key West’s Casa Marina district, The Green Hour is a private vacation retreat designed for privacy, and the ease of indoor-outdoor living…
Old Town Caribbean Estate
21 Guests | 10 Bedrooms | 7.5 Bathrooms
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The Old Town Caribbean Estate is a masterful combination of a classic Key West Victorian home with an exotic Caribbean-style guest house. Gated with a pool, decks, and tropical gardens…
Classic Key West Estate
16 Guests | 5 Bedrooms | 5.5 Bathrooms
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The timeless charm of this Classic Key West Estate vacation rental historic and exotic. The location of this estate property is where you’ll find some of the most iconic destinations on the island…
Duval Street Fantasy Resort Villa
8 Guests | 3 Bedrooms | 3 Bathrooms
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This one-of-a-kind Fantasy Resort Villa vacation rental perfectly blends two charming historic cottages right into a little bit of island heaven…
Ultimate Sunset Guest House
4 Guests | 2 Bedrooms | 2 Bathrooms
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Enjoy the luxury of the grounds, outdoor kitchen, pool and waterslide, and views without the need to book the entire property, guaranteeing your privacy and private enjoyment…
Tropical ~ Tranquility
8 Guests | 4 Bedrooms | 3.5 Bathrooms
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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…
The Caroline House Estate
10 Guests | 5 Bedrooms | 3.5 Bathrooms
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This gorgeous classical Key West Estate property is quite possibly the most stylish blend of historic Victorian-Caribbean with stunning island-modern that we have seen…
Amanda’s Dream Suites
10 Guests | 4 Bedrooms | 3 Bathrooms
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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…
Flower Power House
13 Guests | 5 Bedrooms | 4 Bathrooms
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Immerse yourself in this one-of-a-kind tropical wonderland! Welcome to the Flower Power House, where Key West’s free spirit lives on in every colorful corner…
Amelia’s Hideaway
10 Guests | 4 Bedrooms | 4 Bathrooms
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Amelia’s Hideaway vacation rental is a one-of-a-kind vacation villa, and is perfectly situated just off Upper Duval. Boasting a beautiful courtyard with a crystal clear swimming pool…
Villa Deja vu Key West
10 Guests | 4 Bedrooms | 3 Bathrooms
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A carefree beachiness permeates every room of this two-story wooden house and it had taken me right back to bliss. Spacious private backyard that showcases a tropical pool garden…
Villa Porta del Sole
6 Guests | 3 Bedrooms | 3.5 Bathrooms
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For unmatched sunset watching from your private sandy beach or king suite balcony, tropical birds visiting your tranquil backyard, and slow mornings by the pool, welcome to Villa Porta del Sole…
Pavilion Villa
10 Guests | 4 Bedrooms | 3 Bathrooms
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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. with a pool, spacious deck, and lushly landscaped garden…
Twice as Nice on Duval Street
8 Guests | 4 Bedrooms | 4 Bathrooms
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The Twice As Nice vacation rental is a perfect solution for a discerning group who want to lodge together in luxury and yet require the maximum privacy offered with four separate upscale suites…
Garden Suite
6 Guests | 2 Bedrooms | 2 Bathrooms
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The allure of the boho styleGarden Suite vacation rental comes from its one-of-a-kind architectural design, the fun decor, and its authentic Key West pool garden setting…
Key West Mile Zero Suite
4 Guests | 2 Bedrooms | 2 Bathrooms
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This stylish 2 bedroom, 2 bathroom suite, is discretely perched above the Mile 0 location, above the island bustle, yet with an enviable birds-eye view of the famous scene below…
Designer Octagon House
8 Guests | 4 Bedrooms | 4 Bathrooms
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This iconic Designer Octagon House of Key West, makes a grand architectural statement. Truly a home of fine distinction, featuring 5-Star Quality Resort Amenities standards…
Private Island Key West Beach House
6 Guests | 3 Bedrooms | 4 Bathrooms
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Sunset Key ~ VIP– Nestled on the exclusive 27-acre Sunset Key island, this Private Island Beach House offers a luxurious and serene retreat…
Key West Sunset Sojourn
8 Guests | 4 Bedrooms | 4 Bathrooms
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The ultimate Key West dream home on a private island surrounded by turquoise waters and balmy breezes. Elegant yet relaxed. Watch tropical sunsets from a private rooftop lookout deck…
Tree Tops
4 Guests | 2 Bedrooms | 1 Bathrooms
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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. Down home island charm, nicely decorated…
Private Pool Garden Villa
6 Guests | 3 Bedrooms | 2.5 Bathrooms
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Experience true tropical Key West living as the locals do in this spacious mid-century private garden oasis home with large swimming pool and poolside entertainment cabana…
Heavenly Hideout at Rainbow’s End
8 Guests | 4 Bedrooms | 4 Bathrooms
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A unique penthouse where you can experience a wonderful journey. This tropical retreat is the ultimate destination…
Key West Wabi Sabi
8 Guests | 4 Bedrooms | 3.5 Bathrooms
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This thoughtfully renovated retreat preserves the home’s original character and vintage Key West vibe while embracing an ideal indoor-outdoor feel. It is perfect choice for your trip…
Key West Dreamin’
6 Guests | 2 Bedrooms | 2 Bathrooms
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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…
Bella Grand Premier Estate
10 Guests | 5 Bedrooms | 5.5 Bathrooms
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Bella Grand Premier Estate is an extraordinary Old Town Key West Luxury Estate, available as an exclusive monthly rental. Inspired by romantic turn-of-the-century architecture…
Admirals Gold
8 Guests | 4 Bedrooms | 3.5 Bathrooms
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Private Key West Luxury Villa – The perfect destination for those seeking a spacious and luxurious escape for the entire family. This entire 3-Story home is filled with natural light…
Caribbean Cottage
8 Guests | 2 Bedrooms | 2 Bathrooms
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If you are looking for a truly authentic Key West experience, this cottage could be the perfect one for you. This charming property is located in the Upper-Duval Street historic neighborhood…
Down Island Digs
6 Guests | 2 Bedrooms | 2 Bathrooms
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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 are just steps to Duval St…
Ocean View Luxury Villa
8 Guests | 3 Bedrooms | 4 Bathrooms
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Ocean View Luxury Villa offers an exceptional vacation experience with stunning ocean views and easy beach access. This property combines classic Key West charm with modern luxury…
Coco’s Poolside Retreat
8 Guests | 3 Bedrooms | 2.5 Bathrooms
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Coco’s Poolside Retreat is a cheerful three-story townhome tucked inside a private, gated mini-compound in Old Town Key West. This laid-back retreat is situated in a tropical wonderland…
Casa Serena
10 Guests | 3 Bedrooms | 4 Bathrooms
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Private Courtyard Vacation Home in Casa Marina, Key West – Designed for extended stays that prioritize comfort, privacy, and an easy island rhythm. This home livable Key West experience…
The Grand Marshall
10 Guests | 5 Bedrooms | 4.5 Bathrooms
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The focal point of this combined property of 2 homes, is the indoor/outdoor island living space combining the back yards with 2 swimming pools, spacious decks, and covered porches…
Vintage Luxury Cottage On Duval
4 Guests | 1 Bedrooms | 1 Bathrooms
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This luxury renovated turn-of-the-century Vintage Luxury Cottage vacation rental is hidden just off upper Duval Street in Old Town…
By The Beautiful Sea
6 Guests | 3 Bedrooms | 2 Bathrooms
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A Key West Beach Front Condo. 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 are not easy to come by…
Exclusive Key West Beach Front
6 Guests | 2 Bedrooms | 3 Bathrooms
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Rare one-of-a-kind Key West Beachfront vacation rental has breath taking views overlooking the ocean and natural aquatic bird sanctuary…
Havana Moon Over Duval
4 Guests | 2 Bedrooms | 2 Bathrooms
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Inside the Havana Mooncottage on Duval Street you find a complete transformation with a decidedly upscale minimalist renovation design and decorum that is understated and elegant…
Romance on William Street
8 Guests | 3 Bedrooms | 3.5 Bathrooms
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Discover the perfect blend of classic Key West charm and modern elegance at “Romance on William.” Experience a refined getaway that captures the essence of island living…
The Kaleidoscope House
6 Guests | 3 Bedrooms | 3.5 Bathrooms
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A Colorful Key West Hideaway. Tucked away on a quiet, foliage-lined street in Old Town, this vibrant tropical retreat is nestled in and amongst the best of Key West…
Sunset Sonnet Luxury Villa
4 Guests | 2 Bedrooms | 3 Bathrooms
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Covered roof-top deck viewing tower with private sunset view, covered wrap around veranda porches with pool garden views, mature tropical landscaping, shared oasis style swimming…
Sunset Serenade
6 Guests | 2 Bedrooms | 2.5 Bathrooms
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Sunset Serenade vacation rental, is nestled around an oasis style swimming pool, with lavish tropical gardens. Enjoy the the 5 star amenities in your own private custom home…
Cockadoodle Cottage On Duval
4 Guests | 2 Bedrooms | 2 Bathrooms
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Keeping with modern minimalist renovation design & decorum, this cottage is appointed with modern island furnishings and art work…
Truman Treasure
5 Guests | 3 Bedrooms | 2 Bathrooms
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The interior designer takes full advantage of every inch of space of this wonderful home. The private resort-style swimming pool is steps away. The poolside garden setting is immaculate…
Casa Bella Petite le Bleu
4 Guests | 2 Bedrooms | 2 Bathrooms
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From the front curb this cottage is a picture of perfection. Nestled amongst a remarkable collection of authentic structures, its historic characteristics are captivating…
Governor’s Retreat
6 Guests | 3 Bedrooms | 2.5 Bathrooms
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A celebration of the tropical Key West style is made imminent throughout the interior of the house with a perfect mixture of coastal and rustic furnishings. The feel is cheerful and relaxing…
Key of Blue
8 Guests | 4 Bedrooms | 3 Bathrooms
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Monthly Key West Retreat with Boat Parking. Set in the easygoing rhythm of New Town, Key of Blue is a relaxed rental designed for guests who want space, simplicity, and a deeper stay on the island…
Island Elegance
8 Guests | 3 Bedrooms | 3 Bathrooms
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The Island Elegance rental is strikingly set in the oft-missed Key West mid-town neighborhood. This corner lot home makes a classical curbside statement with a contemporary twist…
Serenity Now
4 Guests | 2 Bedrooms | 2.5 Bathrooms
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Imagine a perfect vacation in Old Town Key West, where luxury and convenience blend seamlessly. Serenity Now is a stunning townhome offering an ideal blend of elegance and relaxation…
Blue Porch Cottage
4 Guests | 1 Bedrooms | 1.5 Bathrooms
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Situated snugly in Old Town, the neighborhood’s authenticity pairs perfectly with the owners’ evident passion and penchant for design: you’ll get all the historic charm yet all the modern amenities…
Sun, Sea, & Citrus
5 Guests | 2 Bedrooms | 2 Bathrooms
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Our guests are in for a treat at such a bright and beautiful entire first-floor unit in Key West. This inviting two-bedroom bungalow is perfectly situated on a calm and quiet street in Old Town…
On Hemingway’s Rounds
4 Guests | 2 Bedrooms | 2 Bathrooms
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This stylish vintage house is listed on the Key West National Register of Historic Places. Perfectly redesigned from top-to-bottom, with upscale fixtures, amenities, and luxurious outdoor living…
Island Interlude
4 Guests | 2 Bedrooms | 2.5 Bathrooms
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Island Interlude is an ideal home base for travelers looking to explore, unwind, and settle into island life. Around the corner from the iconic Blue Heaven and steps from Fort Zach’s beach and trails…
Key West Island Village Cottage
6 Guests | 2 Bedrooms | 1.5 Bathrooms
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This classic Key West cottage is nestled in one of the island’s most charming and interesting residential neighborhoods…
Rooftop Renaissance
4 Guests | 1 Bedrooms | 2 Bathrooms
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Rooftop Renaissance vacation rental design is a Heritage Victorian. This one-of-a-kind monthly rental is situated on two floors of one side of a grand historic home on Caroline Street…
Key West Poolside Loft
4 Guests | 2 Bedrooms | 2 Bathrooms
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Cleverly tucked away in the exclusive gated community of Key West Truman Annex, here you’re in an island cottage style condo, with a loft and private deck…
Sweet Sunshine Garden Flat
4 Guests | 2 Bedrooms | 1 Bathrooms
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Sweet Sunshine Garden Flat can make that dream come true. Set in the beautiful Key West Truman Annex Shipyard condominium complex. Welcome to your own slice of paradise…
Tropical Chill
4 Guests | 2 Bedrooms | 2 Bathrooms
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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…
Elegant Key West Tree House
4 Guests | 2 Bedrooms | 1 Bathrooms
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The Elegant Key West Tree House is a unique rental. Discretely built back off the street to quietly overlook an historic tropical garden, this Boho luxe rental encompasses the entire 2nd floor…
Seaport Hideaway
4 Guests | 2 Bedrooms | 1.5 Bathrooms
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Seaport Hideaway – Historic Condo in the Heart of Key West. This unique, limited-edition residence offers a perfect mix of history, charm, and tropical comfort…
Island Sunshine Bungalow
4 Guests | 2 Bedrooms | 1 Bathrooms
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Historic and designer at once, this imaginative one-and-a-half-story shot-gun cottage is ideally situated in the Heart of Old Town Key West. The porch exudes a welcoming charm…
Hidden Story-Book Cottage
2 Guests | 1 Bedrooms | 1 Bathrooms
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Tucked away down a garden path in the heart of Old Town, this colorful 1933 cottage is a true hidden gem—completely secluded from the street and surrounded by thriving plant life…
Little Digs Key West
2 Guests | 1 Bedrooms | 1 Bathrooms
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Delightfully designed, Little Digs Key West is the perfect home base for guests looking to settle into Old Town for a longer stay. Just steps from some of the island’s most beloved local spots…
Maison Soleil
6 Guests | 3 Bedrooms | 3 Bathrooms
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Welcome to Maison Soleil. This gorgeous, newly renovated Sunset Key villa features plentiful space, serene, clean design, a lovely outdoor area with a private pool, and so much more…
Villa Corazon
6 Guests | 3 Bedrooms | 3.5 Bathrooms
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A luxurious retreat featuring a heart-shaped pool and a blend of historic Key West charm with modern elegance, showcasing a blend of modern aesthetics and laid-back Caribbean vibes…