Discover a selection of 461 vacation rentals in Uptown - Upper Duval, 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 $159 per night, and houses and cottages are popular options for a stay in Uptown - Upper Duval. Either way, you'll find a rental for everyone's needs.
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Top rated rentals — Uptown - Upper Duval
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What are the top vacation rentals in or near Uptown - Upper Duval?

The heart wants what it wants, and right now it wants to take a vacation. It's time to pack your bags and escape to one of these top vacation rentals in or near Uptown - Upper Duval:

  • Make use of conveniences like a nearby laundromat and nearby ecotour services at "Key West Oasis, Seperate Cottage". Situated around 1 mile from Uptown - Upper Duval, this vacation rental has 2 bedrooms and is a hit with guests.
  • "Cloud 9 ~ It's Heaven On Earth In This 3b" is another top-notch choice, offering 3 bedrooms, a nearby hospital, nearby ecotour services and more. It's around 1 mile from Uptown - Upper Duval.

For even more great options, use the search bar at the top of the page to find the perfect Uptown - Upper Duval vacation rental for you.

What are the top-rated vacation rentals for weekend getaways in or near Uptown - Upper Duval?

There's nothing quite like a short break to reset your batteries. If you're ready for some good old-fashioned R&R, these popular weekend getaways in and near Uptown - Upper Duval make the perfect base for a mini break:

  • If spending time in the outdoors is a top priority for you, book a day or two at "Casa Cove Beautiful Tropical Decorated 3 King Suites Pool 2 Mi Beach". Around 4 miles northeast of Uptown - Upper Duval, it's close to Sugarloaf Beach and Higgs Beach. Amenities at this property include a fitness facility and an oven.
  • Another terrific option is "Starfish - Sunny Townhome In Quiet Truman Annex Two Blocks From Duval St", which is around 1 mile northwest of Uptown - Upper Duval. When you're not relaxing in your rental making the most of cable/satellite TV services and golf, check out some of the area's highlights like Key West Butterfly and Nature Conservatory and Curry Mansion Museum.

Can I find studio apartments for rent in and around Uptown - Upper Duval?

Typically small in size, easy on the wallet and well located, it's hard not to succumb to the charms of a studio apartment. Make yourself comfortable in one of these vacation rentals and appreciate Uptown - Upper Duval up close:

  • Wake up, go exploring and then do it all over again at "Condo In Old Town Key West's Truman Annex". This property is a superb base for seeing the sights and comes with amenities including a nearby beach and nearby ecotour services.
  • Another appealing choice is "Your Condo By The Beach With Ocean View". Take advantage of cable/satellite TV services, a barbecue grill and other conveniences during your stay.

When you're ready to step out of your studio apartment and cross off the sights, there's loads to keep you amused around Uptown - Upper Duval. Interested in cultural attractions? Plan a visit to Red Barn Theatre and Red Barn Theater.

Can I find short term rentals in or near Uptown - Upper Duval?

Now and then, you've just got to get away from it all, even if it's only for a few days or so. Experience a pleasant mix of rest and recreation at one of these short-term rentals in or around Uptown - Upper Duval:

  • "Casa Capri Beautiful Tropical Style House With 3 King Suites Pool 2 Mi To Beach" is near the center of Uptown - Upper Duval, which means you'll have loads of things to keep you busy. Make your way to cool attractions like Ernest Hemingway Home and Museum and Audubon House and Tropical Gardens when you're not making the most of your cozy rental.
  • Sleep, relax and explore from "Villa Josine ~ 4 B/4. 5 Ba Large Designer Home With Pool In A Great Location", another popular option. Smathers Beach and Southernmost Point should be on your to-do list when you're ready to go sightseeing.

What are the best romantic weekend getaways in or near Uptown - Upper Duval?

Nothing says "I love you" quite like a romantic weekend trip. If you'd like to spend a couple of evenings away with your honey, we've got some romantic getaways in and around Uptown - Upper Duval that will set your heart aflutter:

  • Around 1 mile from Uptown - Upper Duval, "Key West Oasis, Seperate Cottage" is the perfect place for lovestruck couples. Beauty services and a swimming pool are just some of the amenities here.
  • "Cloud 9 ~ It's Heaven On Earth In This 3b" is another terrific option that'll woo you. It's around 1 mile from Uptown - Upper Duval and has a nearby marina and a swimming pool.

Are there mansions for rent in or near Uptown - Upper Duval?

Nothing screams "best vacation evvv-er" like staying in a mansion. Spoil your loved ones with a memorable getaway at one of these mansions for rent in and around Uptown - Upper Duval:

  • Situated 1 mile to the northwest of Uptown - Upper Duval, "Noona's Mansion @ The Annex Grand Home And Pool + Last Key Services" is the ideal place to relax in the lap of luxury. Nice touches here include a swimming pool and beauty services.
  • Alternatively, score Brownie points with your crew and spend a week or two at "Captiva" ~ , Historic Mansion Suite With Community Pool". It's situated 1 mile to the north of Uptown - Upper Duval and offers amenities like golf, concierge services and more.

What are the best large group vacation rentals in or near Uptown - Upper Duval?

Sneak a peek at these large group vacation rentals in or near Uptown - Upper Duval where you won't have to leave anyone off your guest list:

  • Providing space, comfort and privacy, you'll get your guests' nod of approval at "New Photos: Drive To Your Getaway". Up to 12 people can stay at this escape which has 5 bedrooms, a kitchen and a chef. This group favorite is around 0.1 miles to the southeast of Uptown - Upper Duval.
  • Nothing's more important than being together with loved ones, and "William Skelton Home - Heart Of Key West" makes it easy to do that. Located around 1 mile to the northwest of Uptown - Upper Duval, as many as 14 people can stay in this vacation rental which has 6 bedrooms. A kitchen and a garden are among the many amenities you'll have at hand.

What are the best houses for rent with a pool in or near Uptown - Upper Duval?

From lively games of freeze tag to refreshing morning dips, a pool promises fun for both kids and adults. Earn some brownie points with the family by renting a house with a swimming space in or near Uptown - Upper Duval:

  • Every day can be a pool day at "Casa Capri Beautiful Tropical Style House With 3 King Suites Pool 2 Mi To Beach". A stair gate and a travel crib are a few of the other amenities that help make this place a favorite.
  • Another sought-after option is "Casa Cay West Beautiful Tropical House 3 Bedrooms 2 King Suites Pool 2 Mi Beach". There's a lot to love about this retreat apart from its pool, such as a microwave oven and a smart TV.

What are the best large family vacation rentals in or near Uptown - Upper Duval?

Whether your ideal escape is out in the country or by the beach, you'll enjoy it even more if you share it with those closest to you. Check out these large family vacation rentals in or near Uptown - Upper Duval and bring the entire crew along:

  • Get your nearest and dearest under the same roof 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 Uptown - Upper Duval and features amenities such as a kitchen and towels.
  • "Casa Cove Beautiful Tropical Decorated 3 King Suites Pool 2 Mi Beach" is another top pick for families. It's around 4 miles to the northeast of Uptown - Upper Duval, has 3 bedrooms and accommodates up to 8 people. Useful amenities here include a smart TV and childrens activities.

If you're hoping to visit some family-friendly attractions in the area, you won't have far to go. Duval Street, Key West Aquarium and Key West Wildlife Center offer fun for both kids and grown-ups.

Can I find family cabin rentals in or near Uptown - Upper Duval?

Vacation with the kiddos in a family cabin rental in or near Uptown - Upper Duval and get set to build some fantastic memories together. Here are a couple of favorites:

  • "Cabin - Orange Blossom Suite | 1 Bedroom 1 Bath In Steps Off Duval" - Enjoy precious time with your nearest and dearest at this getaway, which is around 1 mile northwest of the center of Uptown - Upper Duval. A fridge and coffee and tea making facilities are among its family-friendly amenities.
  • "Cabin - Hidden Treasure - 2 Bedroom 2 Bath With Shared Pool" - This property has also been designed with families in mind and is around 1 mile north of Uptown - Upper Duval. Offering a dishwasher, a barbecue grill and more, it'll get your group's stamp of approval.

For more options, use the search bar at the top of the page and adjust the filters to find the Uptown - Upper Duval vacation rental that's perfect for your needs.