Discover a selection of 1,500 vacation rentals in Old Town Key West, Key West that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and private pools. Prices start at $89 per night, and houses and cottages are popular options for a stay in Old Town Key West. Either way, you'll find a rental for everyone's needs.
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Top rated rentals — Old Town Key West
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What are the top vacation rentals in or near Old Town Key West?

The heart wants what the heart wants, and right now that's a vacation. Now's the time to pack your bags and take off to one of these top vacation rentals in or near Old Town Key West:

  • Around 4 miles from the center of Old Town Key West, you'll want to keep coming back to Casa Cove Beautiful Tropical Decorated 3 King Suites Pool 2 Mi Beach. It has 3 bedrooms and a host of amenities including children's toys and a washing machine.
  • Villa Josine ~ 4 B/4. 5 Ba Large Designer Home With Pool In A Great Location also promises a memorable getaway, offering 4 bedrooms, cable/satellite TV services, towels and more. It's around 0.1 miles from Old Town Key West.

For even more great options, use the search bar at the top of the page to find the perfect Old Town Key West vacation rental for you.

What are the top-rated vacation rentals for weekend getaways in or near Old Town Key West?

Forget about those chores, because weekends were made for fun. Head for one of these weekend getaways in and around Old Town Key West and take advantage of all the awesome things to do nearby:

  • Located 4 miles to the east of central Old Town Key West, Casa Cay West Beautiful Tropical House 3 Bedrooms 2 King Suites Pool 2 Mi Beach appeals to nature lovers and adventurous types. Get out and discover nearby outdoor attractions, such as Key West Wildlife Center and Upper Sugarloaf Sound. If you're up for some fun activities, try off-street parking options or an oven.
  • Alternatively, enjoy a more leisurely pace of life at Sunset And Ocean View In Key West's Truman Annex. About 1 mile west of Old Town Key West, fun activities around here include off-street parking options and beach sun loungers. More interested in sightseeing? Don't miss Boca Chica Beach and Sugarloaf Beach.

What are the best romantic weekend getaways in or near Old Town Key West?

Whether spent in a cabin, a cottage or a condo, a romantic weekend getaway is a perfect way to spice up your love life. Whisk your partner away for a couple of relaxing days at one of these escapes in or near Old Town Key West:

  • Located around 4 miles from Old Town Key West, Casa Cove Beautiful Tropical Decorated 3 King Suites Pool 2 Mi Beach is a perfect place for lovestruck couples. A heated pool and a music library are some of the amenities you'll find here.
  • Villa Josine ~ 4 B/4. 5 Ba Large Designer Home With Pool In A Great Location is another top option that's sure to impress. It's approximately 0.1 miles from Old Town Key West and has air conditioning and shopping.

Are there mansions for rent in or near Old Town Key West?

Nothing screams "Best. Vacation. Ever." like staying in a mansion. Treat the family to an unforgettable getaway at one of these mansions for rent in and around Old Town Key West:

  • Character, style and charm — Captiva" ~ , Historic Mansion Suite With Community Pool has it all. Around 0.1 miles northeast of Old Town Key West and offering an iron and ironing board and WiFi, this place is difficult to beat.
  • Alternatively, score major Brownie points and stay a while at Cortez" ~ , Poolview Suite In Azul Mansion. It's approximately 0.1 miles to the northeast of Old Town Key West and offers amenities like WiFi, a TV and more.

What's the best place to stay if you're looking to rent a house for a weekend in or near Old Town Key West?

Saltwater, sunshine, views of palm trees — you can't beat a weekend escape in Key West. Wake up to the sound of waves gently lapping in the distance, with hot spots like Smathers Beach mere moments away. This laid-back destination is situated 1 mile northwest of Old Town Key West.

What are the best large group vacation rentals in or near Old Town Key West?

Big groups mean big-time fun. They also mean finding a place that'll easily fit your whole squad. Check out our large group vacation rentals in or around Old Town Key West and get everyone together under the same roof:

  • There's plenty of space to move around at New Photos: Drive To Your Getaway. Around 0.1 miles south of Old Town Key West, this sizable retreat has 5 bedrooms that sleep up to 12 guests. It comes with a host of amenities, including optional golf privileges and a stovetop.
  • Invite up to 14 of your dearest friends to William Skelton Home - Heart Of Key West and fill the place with love and laughter. This option has 6 bedrooms and is around 1 mile to the northwest of central Old Town Key West. It's crammed with features to keep large groups happy and comfortable, including nearby birdwatching activities and a kitchen.

What are the best houses for rent with a pool in or near Old Town Key West?

A pool is often a key feature of any unforgettable vacation. Enjoy hours of entertainment splashing around or simply unwinding by the water at one of these refreshing retreats in or near Old Town Key West:

  • Leading our list of cool pool escapes is Casa Cay West Beautiful Tropical House 3 Bedrooms 2 King Suites Pool 2 Mi Beach. Traveling groups will feel at home here, with useful amenities like a hair dryer and optional golf privileges also at hand.
  • Casa Calypso - Beautiful Tropical Style House 3 King Beds Pool 2 Mi To Beach is another top option. After you've enjoyed a dip with the fam, take advantage of other conveniences like a pool and an iron and ironing board.

What are the best large family vacation rentals in or near Old Town Key West?

You'll always have more fun sharing those special memories with the folks closest to your heart. Whether you're planning a family break or spending time with your best friends, we'll have a large vacation rental that's perfect for you. These are two of our best in and around Old Town Key West:

  • Sleeping as many as 8 guests in 3 bedrooms, Casa Cove Beautiful Tropical Decorated 3 King Suites Pool 2 Mi Beach is the ideal place to spend quality time with the family. This top-rated retreat is 4 miles to the east of Old Town Key West and has amenities such as a hair dryer and books.
  • Villa Josine ~ 4 B/4. 5 Ba Large Designer Home With Pool In A Great Location also offers the space you need to make memories with loved ones. This property is around 0.1 miles to the north of central Old Town Key West and accommodates 8 guests in its 4 bedrooms. Air conditioning and a microwave oven will help keep everyone content and comfortable.

If you're eager to visit some family-friendly attractions in the area, you're spoiled for choice. Duval Street, Key West Aquarium and Key West Wildlife Center promise lots of fun for both kids and grown-ups.

Can I find family cabin rentals in or near Old Town Key West?

Escape the busyness of life and treat your loved ones to a vacation of a different sort. Stay in one of these family cabins in or near Old Town Key West and get the camping experience — but with all the creature comforts!

  • Cabin - Orange Blossom Suite | 1 Bedroom 1 Bath In Steps Off Duval - This popular getaway offers air conditioning and a pool and is located approximately 0.1 miles to the west of the center of Old Town Key West.
  • Cabin - Hidden Treasure - 2 Bedroom 2 Bath With Shared Pool - Round up the troops and spend a few nights at this inviting property, which is around 0.1 miles to the north of Old Town Key West. You'll have access to cable/satellite TV services, a dryer and much more.

For more options, use the search bar at the top of the page and adjust the filters to find the Old Town Key West vacation rental that's perfect for your needs.

Are there one-bedroom vacation rentals in or near Old Town Key West?

Romantic getaways, work trips or solo adventures — a one-bedroom vacation property suits a multitude of occasions. One of our options in or near Old Town Key West is sure to fit the bill:

  • It's true! Great things come in small packages, and Condo In Old Town Key West's Truman Annex is a fantastic example of this. This one-bedroom vacation property is just a short distance from the center and includes amenities like nearby birdwatching activities and a microwave oven.
  • Also within easy reach of all the delights of Old Town Key West, Your Condo By The Beach With Ocean View is another popular one-bedroom option. After a big day of seeing the sights, return and enjoy WiFi and a stovetop.