Luxury Vacation Rentals with a Private Pool in Key West

Luxury Vacation Rentals with a Private Pool 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 2 private pool vacation rentals – enter your dates for availability.

Top-rated private pool vacation rentals in Key West

Stunning Townhouse Full kitchen property photo 1

Stunning Townhouse Full kitchen

2 bedrooms•2.5 baths
1,198 US dollars for 2 nights•

~$105 less than other sites

Key West House Private Pool Waterfront property photo 1

Key West House Private Pool Waterfront

3 bedrooms•2 baths
19,477 US dollars for 27 nights•
New

~$1,730 less than other sites

Welcome to private poolside luxury in Key West

Welcome to private poolside luxury in Key West

Soak up island living with luxury private-pool vacation rentals in Key West. Wander pairs hotel-grade polish with the privacy of a tropical home, giving you a serene pool all to yourself. Expect leafy courtyards, sunlit lounges, and effortless indoor to outdoor flow.
Each home is exactly as pictured, meticulously maintained, and supported by 24/7 concierge. Enjoy ultra fast WiFi, pristine cleaning, and thoughtful touches that make it easy to blend work and play.
From classic conch-style hideaways to sleek contemporary retreats, our Key West collection centers around private pools, alfresco lounging, and spaces designed for relaxed luxury.

All homes in Key West

Stunning Townhouse Full kitchen property photo 1

Stunning Townhouse Full kitchen

2 bedrooms•2.5 baths
1,198 US dollars for 2 nights•

~$105 less than other sites

Key West House Private Pool Waterfront property photo 1

Key West House Private Pool Waterfront

3 bedrooms•2 baths
19,477 US dollars for 27 nights•
New

~$1,730 less than other sites

View all homes

Highlights in Key West

Discover a vibrant island paradise where historic charm, legendary sunsets, and crystal-clear waters create the ultimate tropical escape.
Ernest Hemingway Home and Museum
Mallory Square
Southernmost Point Buoy
Dry Tortugas National Park
Duval Street
Key West Butterfly & Nature Conservatory
Fort Zachary Taylor Historic State Park

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 private pool vacation rentals in Key West

Ev charger (1)
Outdoor pool (2)
Exercise equipment (1)
Bbq area (1)
Garden (1)
Dryer (2)
Washer (2)
Oven (2)
Kitchen (2)
Tv (2)
Microwave (2)
Dishwasher (2)
Heating (2)
Coffee maker (2)
Bathtub (1)
Dedicated workspace (2)

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Discover more beyond the pool in Key West

Discover more beyond the pool in Key West

Key West sits where the Gulf meets the Atlantic, an island of technicolor water, swaying palms, and golden hour skies. Pastel cottages and wraparound porches hint at a storied maritime past, while streets pulse with creative energy and a come-as-you-are spirit.
Days drift from reef excursions to local galleries and sunset celebrations on the water. Warm weather makes it a year-round escape, and the compact layout keeps the sea within easy reach. This effortless rhythm is why Wander's luxury vacation rentals in Key West are the perfect choice, whether you are traveling for work or leisure.

FAQs: Vacation Rentals in Key West

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

Wander offers a level of consistency and quality you won’t find with most private pool 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 private pool vacation rentals in Key West?

Some of our most popular private pool vacation rentals in Key West include Stunning Townhouse * Full kitchen! * Sleeps 6, Key West House🌴Private Pool👙Waterfront🛥️, 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 private pool vacation rentals does Wander have available in Key West?

Wander offers 2 private pool 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 private pool vacation rentals in Key West?

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

Do Wander’s private pool 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.