Midtown, FL

Key West

A street with a historic building, parked bicycles, and a clear blue sky.
An aerial view of a mangrove forest with a winding waterway.
A colorful house with a porch, a person sitting on a bench, and a dog on the ground.
A white building with a green window and a sign that reads "Old Town Bakery".
A tree-lined street with buildings on either side, a bicycle, and a red car in the distance.

Things to do

Aerial view of people snorkeling in Key West

Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast

￥6,797
per adult
94% of travellers recommend
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
Key West Parasailing Downtown

Bucket-List Parasailing In Downtown Key West - Highest & Longest Rides

￥10,879
per traveler
92% of travellers recommend
Bucket-List Parasailing In Downtown Key West - Highest & Longest Rides
Family navigating the sea on the glass bottom boat in Key West

Key West Sunset Cruise & Glass Bottom Eco Tour

￥11,198
per adult
76% of travellers recommend
Key West Sunset Cruise & Glass Bottom Eco Tour
Key West Premium Sunset Sail with Champagne, Wine & Tapas

Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar

￥12,647
per adult
94% of travellers recommend
Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar
Aboard the trolley in Key West

Historic Key West Old Town Trolley Hop-On Hop-Off Tour

￥8,901
per adult
88% of travellers recommend
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
Passengers enjoying the shade on the Conch Tour Train in Key West

Key West Conch Tour Train

￥6,498
per adult
88% of travellers recommend
Key West Conch Tour Train
See all activities in Key West

Midtown Hotel Deals

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
The price is ￥24,932 per night from Sep 30 to Oct 1
￥24,932
￥39,453 total
Sep 30 - Oct 1
includes taxes & fees
Book a stay at this spa hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
Southernmost Beach Resort and Guesthouses
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard Key West FL
The price is ￥17,100 per night from Sep 23 to Sep 24
￥17,100
￥28,009 total
Sep 23 - Sep 24
includes taxes & fees
Book a stay at this family-friendly hotel in Key West. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff ...
Blue Flamingo Resort Key West
Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Blvd Key West FL
The price is ￥27,759 per night from Oct 4 to Oct 5
￥27,759
￥41,014 total
Oct 4 - Oct 5
includes taxes & fees
Book a stay at this beach hotel in Key West. Enjoy breakfast (surcharge), a free airport shuttle, and room service. Our guests praise the pool and the restaurant ...
8.8/10 Excellent! (1,789 reviews)
"Loved this property. The pool area is very nice. You can order drinks and food at the pool. The staff is great and very friendly. They have a shuttle that takes you right down to Mallory Square and Duvall street. Definitely staying here again."

Reviewed on Sep 17, 2026

Margaritaville Beach House Key West
Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
3101 N. Roosevelt Blvd Key West FL
The price is ￥15,814 per night from Sep 24 to Sep 25
￥15,814
￥22,823 total
Sep 24 - Sep 25
includes taxes & fees
Book a stay at this beach hotel in Key West. Enjoy free breakfast, free WiFi, and a private beach. Our guests praise the breakfast and the pool in our reviews. ...
Ibis Bay Beach Resort
Havana Cabana at Key West

Havana Cabana at Key West

4 out of 5
3420 N. Roosevelt Blvd Key West FL
The price is ￥18,558 per night from Oct 4 to Oct 5
￥18,558
￥30,736 total
Oct 4 - Oct 5
includes taxes & fees
Book a stay at this business-friendly hotel in Key West. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the helpful ...
Havana Cabana at Key West
Pier House Resort & Spa

Pier House Resort & Spa

4 out of 5
1 Duval St Key West FL
The price is ￥34,551 per night from Sep 28 to Sep 29
￥34,551
￥49,771 total
Sep 28 - Sep 29
includes taxes & fees
Book a stay at this beach resort in Key West. Enjoy a full-service spa, a private beach, and 2 bars/lounges. Our guests praise the pool and the helpful staff ...
Pier House Resort & Spa
See all 2,709 properties in Midtown
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Where to stay in Midtown

Find the best Midtown areas and neighborhoods for the activities you enjoy most. Learn more about Midtown
Learn more about Midtown
A large red brick building with arched windows and a prominent entrance.

Old Town Key West

If you're spending some time in Old Town Key West, Duval Street and Florida Keys Beaches are top sights worth seeing.

A two-story colonial-style building with a balcony, surrounded by lush greenery and palm trees.

Downtown Key West

If you're spending some time in Downtown Key West, Duval Street and Ernest Hemingway Home and Museum are top sights worth seeing.

A white lighthouse surrounded by lush greenery and a white picket fence.

Key West Historic District

Travelers to Key West Historic District praise its fantastic nightlife. If you've got some more time to explore, be sure to make a stop by Duval Street and Florida Keys Beaches.

A row of pastel-colored houses with white railings and a clear blue sky.

New Town

Though New Town might not have many top sights, you can venture to the surrounding area to see attractions like Smathers Beach and Key West Tropical Forest and Botanical Garden.

Midtown, FL

Explore a world of travel with Expedia