Key West vacation homes in Florida

Key West Vacation Rentals

Indulge in the ultimate Florida getaway, with our curated selection of luxury Key West vacation rentals - where sophistication meets the sun-soaked shores of this tropical paradise. Our exquisitely designed homes redefine the art of relaxation and southern living. Accommodating up to 12 guests for an intimate retreat or memorable reunion, our Key West-style retreats promise an exclusive dose of home comfort and freedom whilst away in Sunshine State.

Elevate your Key West vacation experience with private pool access, or the convenience of pet-friendly facilities, allowing every member of your entourage to experience Key West living at its best. Prepare to be captivated by a world of refined southern elegance, tropical charm, and optional Concierge Services designed to create an unforgettable escape.

Things to do

  • Aerial view of the laidback coastal city of Key West
    Enjoy the buzz of Key West Historic Seaport
    Explore some of the best-loved local attractions and enjoy the unique bars and boating, fishing charter and watersport opportunities on offer in Key West.

  • View of Key West Beach in Florida
    Soak up the captivating Key West beaches
    Bask in the island's tropical warmth and romantic sunsets at nearby Smathers Beach, or enjoy snorkeling adventures around its vibrant coral reefs - for the perfect beach-lovers' paradise!

  • Daytime Duval Street scene in Key West Florida
    Explore Duval Street
    This vibrant street is lined with colorful shops and buzzing bars. Take in the lively atmosphere, the entertaining street performers, and snap away at the iconic Southernmost Point buoy.

  • A tourist looks at shop display of rattan bags
    Make for Mallory Square
    Mallory Square in Key West's historic Old Town offers plenty of touristic appeal, with its eclectic mix of shops, renowned local restaurants and picturesque sunsets to take in.

  • A view of the Southernmost Point in Key West
    Visit the Southernmost Point
    Enjoy a classic vacation photo moment and capture your Key West break by the the iconic Southernmost Point buoy - marking the southernmost point in the continental United States.

  • A wooden board with two glasses of rum and coke
    Tour a local Rum Distillery
    Touring a Key West rum distillery is a truly sensory adventure, where the sweet aroma of fermenting molasses mingles with the salty sea breeze. Enjoy sampling the rum neat, or in a regional signature cocktail.

  • View of the Dry Tortugas National Park
    Explore Dry Tortugas National Park
    From the historic 19th century Fort Jefferson to the pristine coral reefs, the journey to this remote national park is an unforgettable experience - as is the snorkeling in the crystal-clear waters!

  • A woman sitting in a chair with a cup of tea and a book in front of a roaring fireplace
    Visit Ernest Hemingway’s House
    Discover where Hemingway wrote his enduring American classics. Wander through historic rooms, landscaped gardens, and meet descendants of his six-toed cats!

  • A diver in the waters off Florida Keys
    Go Reef Swimming & Snorkeling
    Hop aboard a catamaran and sail off the Key West coast, to North America's only living coral barrier reef! Experience an unforgettable moment swimming and snorkeling in this unique marine environment.

Luxury Vacation Rentals

A curated portfolio of the best vacation homes and villas in the world’s top destinations

Travel Planners

Experienced vacation rental and villa experts to help you find the perfect home

Concierge & Support

Enjoy 5-star hotel concierge services and dedicated local support with every stay

A chef prepares vegetables in a private kitchen

Key West Vacation Rentals with Concierge

Elevate your Key West experience with our dedicated Concierge Services. Designed to ensure you enjoy a seamless and indulgent stay, our team are here to arrange everything from car hire, personalized excursions, restaurant reservations, in-home spa services, private chef and more. With our luxury vacation rentals and optional Concierge Services, you can savor the best the island has to offer, all while basking in the comfort and privacy of your exclusive Key West retreat. Welcome to a world where every detail is tailored to exceed your expectations, making your Key West vacation a truly extraordinary experience.

Poolside of Key West 38 in Florida

Key West Vacation Rentals with pools

Discover the epitome of tropical indulgence with our handpicked selection of Key West vacation rentals, each adorned with a refreshing pool to elevate your stay. Dive into the lap of luxury as you explore our award-winning vacation homes, each boasting a unique blend of comfort and style. Picture yourself lounging by the poolside, sipping on a cool beverage, whilst soaking up the year-round Key West sun. Our Key West rentals with pools redefine the vacation experience, offering not just a place to stay, but a sanctuary where relaxation and exclusivity combine.

Whether you're planning a romantic retreat, a classic family escape, or a getaway with pals, our Key West vacation homes provide the ideal backdrop for creating lasting memories. Imagine lazy mornings by the pool, followed by afternoons exploring the lively streets of Key West, before spending evenings unwinding or entertaining in the comfort of your private retreat. Whether you prefer a quaint cottage with plunge pool or a Key West-style home with large pool the whole family will love, our beautiful collection caters to all tastes and preferences.

Book with Confidence

With over 100,000 happy guests every year, you can book your next stay with us with total confidence.

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Scenic balcony view from Key West 17 condo

Key West Condo Rentals

Indulge in a carefree Key West vacation, with our upscale collection of condo rentals. Our Key West condos offer more than just a place to stay – they're an invitation to embrace the laid-back southern charm of the island and enjoy the comfort and luxury of a home-away-from-home. It's an exclusive bolthole where you can soak up the sun, unwind, entertain and embrace all that Key West has to offer.

Looking to be by the beach? Our beachfront condos invite you to step into a world of breathtaking ocean views. Our selection of Key West condos with pool access also promise the prospect of a daily swim, whilst our charming condo rentals in coveted communities provide an effortless way to experience the old world charm of Key West. In fact, you'll find our condos strategically located to offer you the perfect balance – a private haven just moments away from the marina and vibrant energy of Key West's famous attractions. Immerse yourself in the local culture by day and return to the tranquility of your carefree condo rental by night. Offering an affordable way for couples and small groups to experience this famous Florida destination ensures everyone can experience the laid-back charms and captivating coastline of Key West.