Luxury Vacation Rentals in Key West

Never book a bad vacation home again. Every Wander comes with hotel-grade amenities, inspiring views, pristine cleaning and 24/7 concierge service.

We found 1 vacation rentals – enter your dates for availability.

Top-rated vacation rentals in Key West

Home in Key West

2 bedrooms•2.5 baths

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Welcome to Key West

Escape to a private island state of mind with Wander's luxury vacation rentals in Key West. Our handpicked homes deliver the polish of a five-star stay with the privacy of a Keys hideaway. Each residence is professionally operated and always as stunning as the photos.

Think breezy indoor-outdoor living, refined coastal design, spa-like suites, and spaces made for both work and unwinding. Many offer private pools, sunlit terraces, and panoramic water or sunset views, plus ultra fast WiFi and thoughtfully stocked chef kitchens. With pristine cleaning and 24/7 concierge, every detail is handled from arrival to checkout.

Destinations near Key West

All homes in Key West

Home in Key West

2 bedrooms•2.5 baths

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View all homes

Highlights in Key West

Discover a vibrant island paradise where historic charm, legendary sunset celebrations, and tropical adventures create an unforgettable coastal escape.

The Ernest Hemingway Home and Museum

Mallory Square

Southernmost Point of the Continental U.S.

Fort Zachary Taylor Historic State Park

Key West Butterfly & Nature Conservatory

Harry S. Truman Little White House

IT'S A VACATION HOME, BUT BETTER

The Wander difference

Wander is different because we combine the quality of a luxury hotel with the comfort of a private vacation home. Your best trip ever is just a few clicks away.

Only the best homes

We’ll never not look like the pictures. Every Wander is beautiful and expertly operated, so you can leave any stress at the door.

Hotel-grade amenities

We’ll never leave you with nothing to do. From ultra fast WiFi to gyms and pools, our homes make it easy to blend work and play.

24/7 concierge service

We’ll never leave you hanging. Our chat-based Concierge is always available to help – from trip questions to special requests.

Inspiring and stunning views

We’ll never leave you uninspired. Every Wander has stunning views to refresh and inspire your soul. Adventure awaits.

Meticulous cleaning

We’ll never have you check in to a dirty house. Our cleaning teams are meticulous, and there are no chores at checkout.

Safety and security

We’ll never pass you off to a stranger. Every Wander location meets our industry-leading safety standards to give you peace of mind.

Most popular amenities for vacation rentals in Key West

Ev charger (1)

Outdoor pool (1)

Exercise equipment (1)

Dedicated workspace (1)

Iron (1)

Hair dryer (1)

Extra pillows (1)

Other popular amenities & vacation types in Key West

Family vacation rentals in Key West

Discover more of Key West

Sun drenched and storied, Key West blends Caribbean color with Florida ease. Pastel conch houses and royal poinciana trees frame lanes filled with galleries and music. The island’s compact size keeps everything close, while its personality feels boundless.

By day, snorkel the Florida Keys National Marine Sanctuary, bike to Fort Zachary Taylor’s beach, or chart a trip to the remote Dry Tortugas. By night, candlelit patios, lively bars, and legendary sunsets set an irresistible rhythm. With warm breezes year round and water at every turn, this is why Wander's luxury vacation rentals in Key West are the perfect choice, whether you're traveling for work or leisure.

FAQs: Vacation Rentals in Key West

Why should I book a Wander in Key West over other vacation rentals?

Wander offers a level of consistency and quality you won’t find with most vacation rentals.

Every home in Key West delivers the quality of a luxury hotel, paired with the comfort and space of a private vacation home. You get hotel-grade amenities, meticulous cleaning, stunning views, and 24/7 concierge support in every stay. Why would you want to stay anywhere else?

Which are Wander’s most popular vacation rentals in Key West?

Some of our most popular vacation rentals in Key West include Stunning Townhouse * Full kitchen! * Sleeps 6 and Stunning Townhouse * Full kitchen! * Sleeps 6. Guests love the quality of a luxury hotel, the comfort of a private vacation home, and the consistently exceptional experience Wander is known for. Explore the full collection to find the perfect home for your next stay.

How many different vacation rentals does Wander have available in Key West?

Wander offers 1 vacation rentals in Key West, each carefully designed and expertly operated. Browse the full collection to see what’s available for your trip.

What time is check-in and check-out at Wander’s vacation rentals in Key West?

You can check-in to Wander vacation rentals in Key West after 4.00pm and check-out before 10.00am.

Do Wander’s vacation rentals in Key West have WiFi access?

Yes. Every Wander home in Key West has ultra fast, reliable WiFi so you can stay connected throughout your stay.

What is Wander’s cancellation policy?

You can cancel your reservation within 24 hours of booking for a full refund.

For stays of less than 15 nights, you can cancel or reschedule up to 14 days before check-in for a full refund. For stays of 15 nights or longer, the cancellation window is 60 days.

For some homes, a 30-day deadline applies; this will be clearly shown before you book.