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 $125 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 it wants, and right now it's longing for a vacation. It's time to pack your bags and retreat to one of these top vacation rentals in or near Old Town Key West:

  • Around 1 mile from the center of Old Town Key West, it's hard to top "Key West Oasis, Seperate Cottage". It has 2 bedrooms and a range of conveniences like a video library and a separate dining area.
  • Alternatively, make a booking at "Cloud 9 ~ It's Heaven On Earth In This 3b". Located around 1 mile from the heart of Old Town Key West, it has 3 bedrooms and features a nearby marina and an iron and ironing board.

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?

If you're longing to completely switch off for a few nights, you'll find some amazing weekend getaways in and around Old Town Key West. Rest and recharge your batteries at one of these popular options:

  • Around 4 miles to the east of Old Town Key West, "Casa Cove Beautiful Tropical Decorated 3 King Suites Pool 2 Mi Beach" has everything you need for a short weekend break, including heating and an oven. When you're ready to head out and explore, there are lots of outdoor attractions to discover like Sugarloaf Beach and Shark Key.
  • Another terrific option is "Starfish - Sunny Townhome In Quiet Truman Annex Two Blocks From Duval St", which is around 1 mile west of Old Town Key West. When you're not chilling in your rental taking advantage of coffee and tea making facilities and a washing machine, check out some of the area's highlights like Key West Butterfly and Nature Conservatory and National Key Deer Refuge Visitor Center.

Can I find studio apartments for rent in and around Old Town Key West?

Studio apartments are a hard act to beat when it comes to location and convenience. Take a look at these studio apartments for rent in or near Old Town Key West and experience a taste of the local culture:

  • Make "Condo In Old Town Key West's Truman Annex" your home for a week or more. This great vacation rental features amenities including an ocean view and a boat.
  • Alternatively, get into vacation mode at "Your Condo By The Beach With Ocean View", which comes with conveniences such as a nearby laundromat and an iron and ironing board.

When you're ready to walk out of your studio apartment and go exploring, there's loads to entertain you around Old Town Key West. Passionate about culture? Visit Waterfront Playhouse and Key West Art and Historical Society.

Can I find short term rentals in or near Old Town Key West?

Every now and then, you've just got to take some time out, even if it's only for a few short days. Experience a delightful combination of sightseeing and relaxation at one of these short-term rentals in or around Old Town Key West:

  • "Casa Capri Beautiful Tropical Style House With 3 King Suites Pool 2 Mi To Beach" is close to the heart of Old Town Key West, which means you'll have loads of things to keep you on the go. Find your way to well-known sights like Ernest Hemingway Home and Museum and Audubon House and Tropical Gardens when you're not enjoying your cozy digs.
  • Wake up, pour yourself a coffee and then plan what to explore around "Villa Josine ~ 4 B/4. 5 Ba Large Designer Home With Pool In A Great Location". Smathers Beach and Southernmost Point should be on your radar if you stay at this vacation rental.

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

Nothing says "I love you" quite like a romantic weekend trip. If you're longing to spend a couple of relaxing nights away with your honey, we've got some romantic getaways in and around Old Town Key West that will sweep you off your feet:

  • Sneak off on Friday afternoon for a couple of passion-filled nights at "Key West Oasis, Seperate Cottage". Located approximately 1 mile from Old Town Key West, this place comes with lots of nice touches, like beauty services and a swimming pool.
  • Otherwise, spend your break enjoying each other's company at "Cloud 9 ~ It's Heaven On Earth In This 3b", around 1 mile from Old Town Key West. A balcony and a swimming pool will help set the mood.

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

We've got some impressive mansions for rent in and around Old Town Key West. If you're on the lookout for somewhere with lots of room as well as a big dollop of wow factor, these architectural stunners will not disappoint:

  • Located approximately 1 mile to the west of Old Town Key West, "Noona's Mansion @ The Annex Grand Home And Pool + Last Key Services" is the perfect place to put your feet up in the lap of luxury. Amenities offered here include beauty services and golf.
  • Alternatively, score Brownie points with your crew and settle into "Captiva" ~ , Historic Mansion Suite With Community Pool". It's about 0.1 miles to the northeast of Old Town Key West and comes with a swimming pool, concierge services and more.

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

Share your stay and boost your odds of having fun. Whether you're planning an action-packed getaway with friends or a big family get-together, you'll have your choice of large group vacation rentals in and around Old Town Key West:

  • Providing space, privacy and comfort, you'll get your guests' seal of approval at "New Photos: Drive To Your Getaway". Up to 12 people can be accommodated at this property which has 5 bedrooms, a swimming pool and a garden. This group getaway is around 0.1 miles to the south of Old Town Key West.
  • Invite as many as 14 of your friends to "William Skelton Home - Heart Of Key West" and fill its spaces with love and laughter. This popular option has 6 bedrooms and is around 1 mile to the northwest of Old Town Key West. It's crammed with features to keep a large group happy and comfortable, including a swimming pool and a garden.

Are there large vacation rentals that sleep 30 or more in or near Old Town Key West?

Whether you're arranging a big event like a wedding or a getaway with the special people in your life, we can help you find a space to fit your group. Send invites out to your gang and explore these large vacation rentals in or near Old Town Key West:

  • "All Together Now @ Old Town Three Homes And Pools + Last Key Services": The more guests you bring along the merrier to this popular vacation home. It has 13 bedrooms, accommodates up to 32 people and features a host of amenities, such as a swimming pool and a balcony.
  • "Six Dog - Friendly Homes In Quiet Neighborhood With Private Pool And Hot Tub": Offering the trifecta of space, privacy and comfort, this property houses up to 34 people in its 12 bedrooms. A kitchen and a swimming pool are among the features that'll help keep your guests content.

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

Having access to a pool is always a nice bonus when you're vacationing, especially if you're traveling with youngsters. Stay, play and splash the days away at one of these houses with a pool in or near Old Town Key West:

  • Pack your swimming gear and enjoy a fun stay at "Casa Capri Beautiful Tropical Style House With 3 King Suites Pool 2 Mi To Beach". Other amenities here include a porch and books.
  • "Casa Cay West Beautiful Tropical House 3 Bedrooms 2 King Suites Pool 2 Mi Beach" is another top-rated option. After you've enjoyed a dip with the fam, make use of a living room and nearby ecotour services.

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

It's always more fun to share the good times with the folks that are closest to your heart. Whether you're planning a family escape or taking time out with friends, Vrbo has a large vacation rental that's just right for you. These are two of our best in and around Old Town Key West:

  • Get everyone together at "Cloud 9 ~ It's Heaven On Earth In This 3b", which has 3 bedrooms that sleep up to 7 guests. This escape is located 1 mile to the northwest of Old Town Key West and comes with amenities such as a microwave oven and a toaster.
  • "Casa Cove Beautiful Tropical Decorated 3 King Suites Pool 2 Mi Beach" is another popular option. It's around 4 miles to the east of Old Town Key West, has 3 bedrooms and can accommodate up to 8 people. Handy amenities here include a fridge and childrens activities.

When you're ready to venture outside and explore, there are lots of family-friendly attractions in the area to keep everyone happy and entertained. Duval Street, Key West Aquarium and Key West Wildlife Center should be on your itinerary.