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Midtown, Key West, Florida, United States of America
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Midtown vacation rentals

We found 1,417 vacation rentals — enter your dates for availability

Discover a selection of 1,500 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 $147 per night, and condos 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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Find spaces that suit your style

Condos/Apartments

View 593 Condos/Apartments

Bungalows

View 89 Bungalows

Houses

View 646 Houses

Cabins

View 89 Cabins

Townhouses

View 102 Townhouses

Cottages

View 89 Cottages

Studios

View 127 Studios

Resorts

View 33 Resorts

Hotels

View 134 Hotels

Find the best place to stay — Midtown

Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym

Sleeps 4 · 1 Bedroom · 1 Bathroom
$290 avg/night
(159)

SOUTHERNMOST SWIM AND SOCIAL CLUB - With 6 Passenger Gas Golf Cart & 6 Bikes!

Sleeps 6 · 3 Bedrooms
$300 avg/night
(2)

Island Hideway Minutes From Higgs Beach

Sleeps 8 · 3 Bedrooms · 2 Bathrooms
$245 avg/night
(1)

**LARGE PRIVATE HEATED POOL and PATIO**1/3 Mile from Beach

Sleeps 8 · 2 Bedrooms · 2 Bathrooms
$147 avg/night
(12)

Poolside Paradise // Large private home with luxury kitchen & outdoor space!

Sleeps 7 · 3 Bedrooms · 2 Bathrooms
$271 avg/night

THOMPSON'S COURT - Mid Town Getaway with pool & jacuzzi

Sleeps 6 · 3 Bedrooms · 2 Bathrooms
$264 avg/night
(3)

Search 1,417 vacation rentals

Top rated rentals — Midtown
Stayed Jul 2021

Key West is the Best!

I had the best trip of my life at this house with a bunch of close friends for my Bachelorette Party. The house was in the perfect location, about 5 minutes from the airport and very close to Duval Street! Our property Danny even came and personally ...

Bebe R.
Bebe R.
Stayed Jul 2021

Perfect Honeymoon

We couldn’t have asked for a better place for our honeymoon. The condo was perfect, the ocean view from the pool was amazing and the weather was awesome all week long (tropical storm included). Sherri was great to work with and we will totally come s...

Maggie H.
Maggie H.
Stayed May 2021

Quiet & Pleasant Friends Trip

Clean and pleasant! Master has everything and space is plentiful. Tip: Secondary king is nice but has no closet for hanging so use the one in the 3rd bedroom, and the shower & bathroom are small but functional. It's close to Higgs beach and far enoug...

Kathleen M.
Kathleen M.
Stayed Apr 2021

Spring Break/Senior Year Trip

My husband found this perfect location for us. Bc my oldest daughter didn’t have the usual Senior year this year we decided to give her a trip with a friend. Our two daughters each brought along a friend for the week. Four teenagers and two adults an...

Sean M.
Sean M.
Stayed Mar 2021

We loved our stay!

We absolutely loved our stay here. The house had everything we needed and more. The location was perfect for us as well. We were close to everything, but still in a family friendly neighborhood. We could easily walk to the beach and search for “treas...

Larae B.
Larae B.
Stayed Feb 2021

Kick back in Key West

Outstanding property. Beautifully decorated. Well supplied. Open concept for gathering. Lovely pool area. Shaded and relaxed seating by the pool. Wonderful Internet that supported the full-time remote workers online non-stop. Danny provides quick r...

Patricia B.
Patricia B.
Stayed Jul 2020

Fabulous House and Great Location!

My friends and I stayed here for a month during the COVID-19 Pandemic and absolutely loved this house. The house itself felt safe and secluded from the outside world with lots of palms trees and foliage. The outdoor areas were great! The tiki hut, th...

Peter A.
Peter A.
Stayed Jul 2020

Perfect!

This house was perfect for our family. The layout is very nice with the two bedrooms being on opposite sides of the house. There are also two sitting areas which is nice, as well. The front area was a perfect spot where I could do yoga or read away f...

Kelly M.
Kelly M.
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How many vacation rentals are available around Midtown, Key West?

Our 2021 property listings offer a large selection of 1,417 vacation rentals around Midtown. From 593 condo and apartment rentals to 89 bungalow rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Can I rent Condos/Apartments in Midtown?

Yes, of course. Vrbo has 593 Condos/Apartments in Midtown. Our other popular types of vacation rentals in Midtown include:

  • Bungalows: 89 rentals available
  • Houses: 646 rentals available
  • Cabins: 89 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Townhouses and more.

Can I find a vacation rental with pool in Midtown?

Yes, you can select your preferred vacation rental with pool among our 1,127 vacation rentals with pool available in Midtown. Please use our search bar to access the selection of vacation rentals available.