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.

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$334 per night from 28 Sept to 29 Sept
NZ$334
28 Sept - 29 Sept
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 ...
8.6/10 Excellent! (2,687 reviews)
"The Blue Flamingo was clean. The staff was kind and helpful. Anything we needed was handled very well."

Reviewed on 26 Sept 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$455 per night from 28 Sept to 29 Sept
NZ$455
28 Sept - 29 Sept
includes taxes & fees
Stay at this spa 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. ...
Southernmost Beach Resort and Guesthouses
Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Blvd Key West FL
The price is NZ$527 per night from 28 Sept to 29 Sept
NZ$527
28 Sept - 29 Sept
includes taxes & fees
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 in ...
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 NZ$258 per night from 27 Sept to 28 Sept
NZ$258
27 Sept - 28 Sept
includes taxes & fees
Stay at this beach hotel in Key West. Enjoy free breakfast, free Wi-Fi and a private beach. Our guests praise the breakfast and the pool in their reviews. Popular ...
8.2/10 Very good! (2,389 reviews)
"If your looking for an a good resort for a value price this is your place. It is full of character!! The staff is friendly, even let us check in early. Beautiful location on the water with lots of outdoor space, just to lounge around. Loved all the hammocks. Do yourself a favor and pay a little extra ..."

Reviewed on 25 Sept 2026

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 NZ$332 per night from 28 Sept to 29 Sept
NZ$332
28 Sept - 29 Sept
includes taxes & fees
Stay at this business-friendly hotel in Key West. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the pool and the helpful staff ...
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 NZ$532 per night from 4 Oct to 5 Oct
NZ$532
4 Oct - 5 Oct
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 ...
Pier House Resort & Spa
See all 2,689 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.

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
A large red brick building with arched windows and a prominent entrance.

Old Town Key West

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

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

Downtown Key West

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

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

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 Duval Street and Florida Keys Beaches.

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

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 Fort East Martello Museum and Gallery.

Midtown Travel Guide

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