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


Midtown Hotel Deals

Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Blvd Key West FL
The price is ¥30,830 per night from Oct 29 to Oct 30
¥30,830
¥44,636 total
Oct 29 - Oct 30
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! (1,793 reviews)
"It is such a convenient location and beautiful place to stay. Beds are comfy! Wish they had a little more to offer on their menu though."

Reviewed on Oct 15, 2026

Margaritaville Beach House Key West
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard Key West FL
The price is ¥19,776 per night from Oct 25 to Oct 26
¥19,776
¥31,140 total
Oct 25 - Oct 26
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
Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
3841 N Roosevelt Blvd Key West FL
The price is ¥18,492 per night from Oct 28 to Oct 29
¥18,492
¥35,921 total
Oct 28 - Oct 29
includes taxes & fees
Book a stay at this beach hotel in Key West. Enjoy free WiFi, 2 restaurants, and a private beach. Our guests praise the pool and the helpful staff in our reviews. ...
8.6/10 Excellent! (2,617 reviews)
"We were very happy with how nice, clean and comfortable our 1 bedroom was. The staff was very helpful via text messages for anything we needed like coffee. The pool was clean and well kept. The shuttle bus to Duval street was a very pleasant surprise and the drivers were really prompt."

Reviewed on Oct 15, 2026

Beachside Resort & Residences
Havana Cabana at Key West

Havana Cabana at Key West

4 out of 5
3420 N. Roosevelt Blvd Key West FL
Fully refundable
The price is ¥22,922 per night from Nov 1 to Nov 2
¥22,922
¥35,827 total
Nov 1 - Nov 2
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 ...
9/10 Wonderful! (1,878 reviews)
"pool was the best with food and bar right next. shuttle service to town was excellent can't wait to go back!"

Reviewed on Oct 15, 2026

Havana Cabana at 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 ¥21,511 per night from Oct 18 to Oct 19
¥21,511
¥29,300 total
Oct 18 - Oct 19
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
Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

4 out of 5
1500 Reynolds Street Key West FL
The price is ¥34,129 per night from Oct 25 to Oct 26
¥34,129
¥49,066 total
Oct 25 - Oct 26
includes taxes & fees
Book a stay at this beach resort in Key West. Enjoy 2 outdoor pools, a full-service spa, and a private beach. Popular attractions Duval Street and Southernmost ...
8.4/10 Very Good! (971 reviews)
"Great property"

Reviewed on Oct 15, 2026

Casa Marina Key West, Curio Collection by Hilton
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

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.

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.

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.

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 Fort East Martello Museum and Gallery.



Midtown, FL

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