Start Your Escape

Discover your next Key West Vacation

Vacation Rentals
Old Town
Bayview Retreat

5 bd / 4 ba

Sleeps
12
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Old Town
Eisenhower Retreat

4 bd / 3 ba

Sleeps
12
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Old Town
Seafarer’s Refuge

4 bd / 3.5 ba

Sleeps
12
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Old Town
Captains Daughter

4 bd / 3.5 ba

Sleeps
12
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Old Town
Hemingway’s Hideaway

4 bd / 3 ba

Sleeps
10
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Key Cove
Paris Mango

4 bd / 4 ba

Sleeps
9
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Key Cove
Banana Breeze

4 bd / 3.5 ba

Sleeps
10
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Key Cove
Southern Comfort

4 bd / 3.5 ba

Sleeps
10
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Key Cove
Havana Daydream

4 bd / 4 ba

Sleeps
10
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Key Cove
Nautical Wheeler

4 bd / 3 ba

Sleeps
8
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Key Cove
Coastal Comfort

4 bd / 3.5 ba

Sleeps
10
View Rental
Our Difference
stunning views
Stunning Views

Key West is unlike any place you’ll ever see. Why not see it the right way? Awake to dazzling daybreaks and wind down with sensational sunsets in your own private paradise. Many of our vacation rentals offer sweeping balconies and airy floor plans so you can enjoy the island view.

docks included
Docks Included

Living like a local doesn’t just happen on land. That’s why most of our Key West vacation homes come with a private boat slip. So you can accent your escape with fishing adventures, snorkeling expeditions or deep dives for dinner. Or just dock your boat and soak in the sunset.

easy breezy
Easy Breezy

Key West is a unique and different place. Shoes and schedules are shunned here. Which is why we accommodate different lengths of stays. From weekend getaways to month-long immersions, our flexibility is practically unheard of in this part of paradise. Let us know exactly what you want, and we’ll make it happen.

white glove service
White Glove Service

Come unwind with us, and discover an immersive and all-inclusive experience that’s every bit as remarkable as your location. Want a fresh meal delivered to your door? Need your laundry cleaned? Curious about local hangouts? Our “white glove” concierge service gives you whatever you want. Whenever you need it.

renew and refresh
Renew & Refresh

There’s something special about your own private oasis. Most of our Key West vacation rentals feature an expansive pool. So you can wash off from your ocean adventure. Or just chill by the water with a fresh drink. Whatever your style, we’ll provide you with plenty of beach towels and sun rays.

perfect balance
Perfect Balance

Our spacious homes are both modern and charming. Enjoy full kitchens, expansive balconies and wide-open rooms. Enveloped in lush natural surroundings. From bachelorette parties to weddings, from family vacations to corporate retreats, we offer something for everyone. All accented and elevated by a higher level of personal service.

Quick Connect
IMPORTANT: You may have seen ads on AirBnB or Craigslist that appear to be about our properties or seem to have been placed by us. Please note that Key West Vacation Homes does NOT advertise on either AirBnB or Craigslist – and your response to any fraudulent “ad” for a Key West Vacation Homes property on either of these sites is NEVER received by us. These are fake ads run by scammers who have NO intention of honoring your reservation. All of us here at Key West Vacation Homes take pride in the security of all our guests. To further protect your valuable personal and financial information and ensure you are renting and communicating with Key West Vacation Homes, contact us directly by phone, email, or via our HomeAway listings.