Discover a selection of 2,000 vacation rentals in Midtown, 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 $207 per night, and houses and bungalows are popular options for a stay in Midtown. Either way, you'll find a rental for everyone's needs.
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Top rated rentals — Midtown
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What are the top vacation rentals in or near Midtown?

Whether you're searching for a cozy retreat for you and your honey or somewhere roomy to fit family and friends, you'll find some top vacation rentals in and around Midtown. Here are a couple to get you inspired:

  • Take advantage of conveniences like games and a porch at "Key West Oasis, Seperate Cottage". Situated around 1 mile from Midtown, this property has 2 bedrooms and is a hit with guests.
  • "Cloud 9 ~ It's Heaven On Earth In This 3b" is another top pick, offering 3 bedrooms, internet services, free WiFi and more. It's around 1 mile from Midtown.

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

What are the top-rated vacation rentals for weekend getaways in or near Midtown?

Your Monday to Friday will be much easier to face if you've got something wonderful planned for the weekend. Give yourself something to look forward to by reserving one of these top weekend getaways in or near Midtown:

  • Book a couple of nights at "Casa Cove Beautiful Tropical Decorated 3 King Suites Pool 2 Mi Beach", around 3 miles to the northeast of Midtown, and you've got yourself the best kind of weekend escape. You'll have outdoor attractions like Key West Tropical Forest and Botanical Garden and No Name Key nearby and conveniences like an outdoor pool and a heated pool at your fingertips.
  • Also look into "Starfish - Sunny Townhome In Quiet Truman Annex Two Blocks From Duval St", which you'll find around 1 mile west of Midtown. After a day of discovering nearby natural attractions like Fort Zachary Taylor Historic State Park and Nancy Forrester's Secret Garden, kick back in your rental and make use of nearby birdwatching activities, a microwave oven and more.

Can I find studio apartments for rent in and around Midtown?

Studio apartments are a tough act to follow when it comes to location, convenience and character. Get comfy in one of these studio apartments for rent in or near Midtown and take in the local vibe and energy:

  • Make "Condo In Old Town Key West's Truman Annex" your home away from home. This sought-after property comes with amenities including nearby birdwatching activities and a hair dryer.
  • Another tempting option is "Your Condo By The Beach With Ocean View". Take advantage of a TV, cable/satellite TV services and other convenient amenities during your vacation.

When it's time to leave your studio apartment and sightsee, there's loads to keep you amused around Midtown. Into art and culture? Pencil in a visit to Studios of Key West and Museum of Art & History at the Custom House.

Can I find short term rentals in or near Midtown?

Now and then, you just need to take a break from it all, even if it's only for a couple of days. Experience a nice combination of relaxation and sightseeing at one of these short-term rentals in or around Midtown:

  • If you're eager to be close to the action, "Casa Capri Beautiful Tropical Style House With 3 King Suites Pool 2 Mi To Beach" will suit your style. It's within reach of the heart of Midtown and a superb base to explore sights like Ernest Hemingway Home and Museum and Audubon House and Tropical Gardens.
  • "Villa Josine ~ 4 B/4. 5 Ba Large Designer Home With Pool In A Great Location" is another wonderful option. Remember to add Smathers Beach and Southernmost Point to your travel itinerary when you're ready to sightsee.

What are the best romantic weekend getaways in or near Midtown?

Whether spent in a cabin, a cottage or a houseboat, a romantic weekend getaway is a perfect way to add some fire to your relationship. Whisk your special someone away for a couple of days at one of these top escapes in or near Midtown:

  • Put on some soft music and slow dance the nights away at "Key West Oasis, Seperate Cottage". Around 1 mile from Midtown, this property has all you need for a romantic weekend away, including beauty services and a restaurant dining guide.
  • Another place where you can enjoy a few idyllic days together is "Cloud 9 ~ It's Heaven On Earth In This 3b". Located 1 mile from Midtown, a dining table and a balcony add to the atmosphere here.

Are there mansions for rent in or near Midtown?

We've got some magnificent mansions for rent in and around Midtown. If you're in search of somewhere with plenty of room as well as a serious dose of wow factor, these stunners will not disappoint:

  • Around 1 mile to the west of Midtown is "Noona's Mansion @ The Annex Grand Home And Pool + Last Key Services". As well as its awe-inspiring design, you'll also love its high-end amenities, such as golf and a swimming pool.
  • With golf, concierge services and a wealth of other high-end amenities, "Captiva" ~ , Historic Mansion Suite With Community Pool" will get your squad's stamp of approval. This opulent retreat is roughly 1 mile to the west of Midtown.

What are the best large group vacation rentals in or near Midtown?

Peep these large group vacation rentals in or near Midtown where you won't have to leave anyone off your invite list:

  • A host of amenities including a beach view and a kitchen make "New Photos: Drive To Your Getaway" a standout. This sprawling property has 5 bedrooms and accommodates up to 12 guests. From central Midtown, it's around 1 mile away to the southwest.
  • "William Skelton Home - Heart Of Key West" is another excellent option. It's around 1 mile to the west of Midtown, has 6 bedrooms and accommodates up to 14 guests. A swimming pool and a kitchen are just a couple of things that'll help make your visit even more memorable.

What are the best houses for rent with a pool in or near Midtown?

A pool is often a must-have feature of any good vacation. Enjoy hours of entertainment splashing about or simply chilling out by the water at one of these rejuvenating escapes in or near Midtown:

  • Every day can be a pool day at "Casa Capri Beautiful Tropical Style House With 3 King Suites Pool 2 Mi To Beach". Childrens activities and a fenced pool are a couple of the other amenities that help make this place so appealing.
  • Alternatively, make a booking at "Casa Cay West Beautiful Tropical House 3 Bedrooms 2 King Suites Pool 2 Mi Beach" and spend lazy days poolside. A swimming pool and a smart TV are other things your fam will love about this rental.

What are the best large family vacation rentals in or near Midtown?

Whether your ideal getaway is out in the country or near the beach, you'll have so much more fun if you share it with people you love. Check out these large family vacation rentals in or near Midtown and bring the whole crew:

  • Sleeping up to 7 guests in 3 bedrooms, "Cloud 9 ~ It's Heaven On Earth In This 3b" is the perfect place to vacation with the family. This top-rated getaway is 1 mile to the west of Midtown and has creature comforts that include nearby ecotour services and a nearby laundromat.
  • "Casa Cove Beautiful Tropical Decorated 3 King Suites Pool 2 Mi Beach" also has the space you need to make memories with loved ones. This property is around 3 miles to the northeast of central Midtown and accommodates 8 guests in its 3 bedrooms. A living room and a travel crib will help keep everyone happy and comfortable.

If you want to see some family-friendly attractions in the area, there's no shortage of choice. Duval Street, Key West Aquarium and Key West Wildlife Center promise lots of fun for all the gang.

Can I find family cabin rentals in or near Midtown?

Family time is the best time, which is why we'll help you find a space where you can truly connect. Book one of these family cabin rentals in or near Midtown and hang out with the people you love the most:

  • "Cabin - Orange Blossom Suite | 1 Bedroom 1 Bath In Steps Off Duval" - Located about 1 mile west of central Midtown, this family-friendly escape offers amenities like cable/satellite TV services and a TV.
  • "Cabin - Hidden Treasure - 2 Bedroom 2 Bath With Shared Pool" - Another awesome choice, this cabin comes with a barbecue grill, a kitchen and more. You'll find it around 1 mile to the west of Midtown.

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