Midtown Travel Guide

Key West

Photo by Graciela Arena
Photo by Graciela Arena
Photo by Ronald Wilson
Photo by Renee Shipley
Photo by Kevin Pauletti


Top hotels in Midtown

Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
3841 N Roosevelt Blvd Key West FL
The price is ฿7,634 per night from 4 Jan to 5 Jan
฿7,634
฿10,191 total
4 Jan - 5 Jan 2026
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! (1,835 reviews)
Pool and hot tub were very nice,chicken walk was excellent! Great staff!!!!

Reviewed on 26 Dec 2025

Beachside Resort & Residences
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard Key West FL
The price is ฿7,378 per night from 4 Jan to 5 Jan
฿7,378
฿10,080 total
4 Jan - 5 Jan 2026
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 ...
8/10 Very Good! (1,803 reviews)
The room was very clean and comfortable. The $15.00 for parking your car was a little of the top tho! You should really give discounts for Florida Residence too, we drove 350 miles to come see Key West and to have to pay all the fees & parking fee is a bit much!

Reviewed on 26 Dec 2025

Blue Flamingo Resort Key West
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
5950 Peninsular Avenue Key West FL
The price is ฿7,476 per night from 8 Jan to 9 Jan
฿7,476
฿10,346 total
8 Jan - 9 Jan 2026
includes taxes & fees
Stay at this luxury hotel in Key West. Enjoy free Wi-Fi, 6 outdoor pools and a marina. Our guests praise the pool and the restaurant in their reviews. Popular ...
8.8/10 Excellent! (1,765 reviews)
Staff was amazing

Reviewed on 29 Dec 2025

Oceans Edge Key West Resort, Hotel & Marina
DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

4 out of 5
3990 S Roosevelt Blvd Key West FL
The price is ฿7,833 per night from 4 Jan to 5 Jan
฿7,833
฿9,880 total
4 Jan - 5 Jan 2026
includes taxes & fees
Stay at this business-friendly resort in Key West. Enjoy free Wi-Fi, breakfast (surcharge) and a free airport shuttle. Our guests praise the helpful staff and ...
8/10 Very Good! (1,001 reviews)
Dinner menu ok, food below average, eat in town! Tram services ok, frequently over loaded requiring a wait for second vehicle. Hotel had no hot water for showering or our last day. Complimentary coffee had coffee grounds and staff didn’t seem to care when notified. Place was clean, well kept.

Reviewed on 25 Dec 2025

DoubleTree Resort by Hilton Grand Key - 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 ฿8,877 per night from 13 Jan to 14 Jan
฿8,877
฿12,301 total
13 Jan - 14 Jan 2026
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. ...
8.6/10 Excellent! (2,956 reviews)
The rooms were very clean and staff was helpful.. We switched rooms and forgot a coat in it that was not returned by housekeeping. The tv in the room was not a smart tv so we had to watch games on our tablet. Otherwise everything else was great

Reviewed on 28 Dec 2025

Southernmost Beach Resort and Guesthouses
Havana Cabana at Key West

Havana Cabana at Key West

4 out of 5
3420 N. Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
The price is ฿12,216 per night from 27 Jan to 28 Jan
฿12,216
฿16,041 total
27 Jan - 28 Jan 2026
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 ...
8.8/10 Excellent! (1,708 reviews)
What a super fun place. Definitely going back.

Reviewed on 26 Dec 2025

Havana Cabana at Key West
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.

Other neighbourhoods around Midtown

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White St. Gallery

If you're looking for some top things to see and do in White St. Gallery and surrounding area, you can visit Duval Street and Clarence S. Higgs Memorial Beach Park.

White St. Gallery
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White Street Gallery District

If you're looking for some top things to see and do in White Street Gallery District and surrounding area, you can visit Duval Street and Clarence S. Higgs Memorial Beach Park.

White Street Gallery District
Smathers Beach which includes a bay or harbour, tropical scenes and a sandy beach

Beachside

If you're spending some time in Beachside, Smathers Beach and Florida Keys Beaches are top sights worth seeing.

Beachside
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Casa Marina

While visiting Casa Marina, you might make a stop by sights like Clarence S. Higgs Memorial Beach Park and Florida Keys Beaches.

Casa Marina
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Meadows

Meadows might not have many top sights, but Duval Street and Key West Cemetery are two attractions nearby that you can check out.

Meadows
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The Meadows

While The Meadows isn't home to many top sights, Duval Street and Key West Cemetery are some notable places to visit nearby.

The Meadows


Midtown Travel Guide