Midtown Travel Guide

Tourist Guide

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.

Activities


Our pick of the best Midtown Hotel Deals

Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard Key West FL
The price is NZ$349 per night from 29 June to 30 June
NZ$349
29 June - 30 June
includes taxes & fees
Stay at this family-friendly hotel in Key West. Enjoy free Wi-Fi, 2 outdoor pools and 2 restaurants. Our guests praise the pool and the helpful staff in their ...
8.4/10 Very good! (2,453 reviews)
"This was such a fun place! It was hard to leave to go touring because there was the huge beautiful pool out our door, also yard games outside all day, foosball and pool and other games. We enjoyed doing many of the activities in the evenings, even got to the karaoke airstream! The staff is available ..."

Reviewed on 27 June 2026

Blue Flamingo Resort Key West
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
The price is NZ$512 per night from 29 June to 30 June
NZ$512
29 June - 30 June
includes taxes & fees
Stay at this beach hotel in Key West. Enjoy free Wi-Fi, 3 outdoor pools and a full-service spa. Our guests praise the pool and the helpful staff in their reviews. ...
8.8/10 Excellent! (3,403 reviews)
"Love it !"

Reviewed on 26 June 2026

Southernmost Beach Resort and Guesthouses
Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection

3.5 out of 5
3850 N Roosevelt Blvd Key West FL
The price is NZ$315 per night from 30 June to 1 July
NZ$315
30 June - 1 July
includes taxes & fees
Stay at this business-friendly hotel in Key West. Enjoy 2 restaurants, breakfast (surcharge) and a free local area shuttle. Our guests praise the pool and the ...
8/10 Very good! (1,250 reviews)
"This property is write down and was traditionally over priced for the stay. The gives run down Dexter vibes and was less than fabulous in its remodeling. One sad elevator and just a general sad run down hotel that might have been nice several decades ago even with the location. Parking was 100% full ..."

Reviewed on 26 June 2026

Hilton Garden Inn Key West / The Keys Collection
Pier House Resort & Spa

Pier House Resort & Spa

4 out of 5
1 Duval St Key West FL
The price is NZ$646 per night from 8 July to 9 July
NZ$646
8 July - 9 July
includes taxes & fees
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 in their ...
9/10 Wonderful! (1,198 reviews)
"Our stay was amazing. I’ve wanted to stay at the Pier House for a long time for a few reasons. The location on the water and the history the property has with the late Jimmy Buffett. The Chart Room bar is a must visit for all who like old fashioned bars that haven’t changed in 55 years. The beach ..."

Reviewed on 26 June 2026

Pier House Resort & Spa
Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Boulevard Key West FL
The price is NZ$569 per night from 5 July to 6 July
NZ$569
5 July - 6 July
includes taxes & fees
Stay at this beach hotel in Key West. Enjoy breakfast (surcharge), room service and a 24-hour fitness centre. Our guests praise the pool and the restaurant in ...
8.8/10 Excellent! (1,813 reviews)
"Beautiful property! Very well maintained. Rooms are spacious, clean and very quiet. Very friendly staff. Excellent restaurant. We loved the pool as the beach had sargassum and was unusable. We booked this hotel bc of the proximity to the beach. We were still happy that we booked it as it is very ..."

Reviewed on 26 June 2026

Margaritaville Beach House Key West
Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
3841 N Roosevelt Blvd Key West FL
The price is NZ$423 per night from 1 July to 2 July
NZ$423
1 July - 2 July
includes taxes & fees
Stay at this beach hotel in Key West. Enjoy free Wi-Fi, 2 restaurants and a private beach. Our guests praise the pool and the helpful staff in their reviews. ...
8.6/10 Excellent! (2,310 reviews)
"The elevator was broken my whole stay and the beach it’s dirty and very small. The pool was good and the food at the pool area was excellent."

Reviewed on 26 June 2026

Beachside Resort & Residences
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.

Our guide on where to stay in Midtown

Find the best Midtown areas for the activities you enjoy most. Learn more about Midtown
Learn more about Midtown

Old Town Key West

While visiting Old Town Key West, you might make a stop by sights like Florida Keys Beaches and Duval Street.

Key West Historic District

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

Downtown Key West

While visiting Downtown Key West, you might make a stop by sights like Duval Street and Ernest Hemingway Home and Museum.

New Town

While there might not be top attractions in New Town, you can explore the larger area and discover places like Smathers Beach and Key West Tropical Forest and Botanical Garden.



Midtown Travel Guide

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