Explore top 2026 4 Star Hotels in Fleming Key

Name: Winslow's Bungalows - Key West Historic Inns
Price range: $276 total

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Top Fleming Key 4 Star hotels

Blue Flamingo Resort Key West

3820 North Roosevelt Boulevard Key West FL

Fully refundableReserve now, pay when you stay

$166 nightly

$187 total

Nov 16 - Nov 17

Total with taxes and fees

This hotel features 2 restaurants, 2 outdoor pools, and a 24-hour gym. There's fun for all ages with mini golf and a playground, and families will appreciate ...

Margaritaville Beach House Key West

2001 South Roosevelt Blvd Key West FL

Fully refundableReserve now, pay when you stay

$285 nightly

$321 total

Nov 18 - Nov 19

Total with taxes and fees

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the 24-hour gym and perks like a free airport shuttle. You'll appreciate the hot tub, ...

8.8/10 Excellent! (1,816 reviews)

"Really enjoyed our brief stay and we wished we planned to stay longer. Definitely want to come back. Rooms are great. Property amenities like the shuttle to and from downtown, pool, and tin cup chalice restaurant are great! Staff super friendly and helpful. Loved the text check ins from the manager ..."

Reviewed on Nov 12, 2026

Havana Cabana at Key West

3420 N. Roosevelt Blvd Key West FL

Fully refundableReserve now, pay when you stay

$171 nightly

$192 total

Nov 29 - Nov 30

Total with taxes and fees

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Business travelers can take advantage of the free WiFi in public areas. Enjoy the hot tub ...

9/10 Wonderful! (1,904 reviews)

"The shuttle service is extremely helpful if you don’t have a car given it is quietly away from the heavy tourist area. The pool was wonderful with an array of floats. Nice temperature! Bar service and breakfast were great. Staff was very nice and informative about places to go and eat. They could ..."

Reviewed on Nov 11, 2026

Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL

Fully refundableReserve now, pay when you stay

$279 nightly

$314 total

Nov 30 - Dec 1

Total with taxes and fees

A full-service spa, 3 outdoor pools, and a restaurant are all featured at this hotel. Traveling on business? Take advantage of the 2 conference rooms, free WiFi ...

Parrot Key Hotel & Villas

2801 N Roosevelt Blvd Key West FL

Fully refundableReserve now, pay when you stay

$193 nightly

$217 total

Nov 30 - Dec 1

Total with taxes and fees

This smoke-free hotel features 4 outdoor pools, a gym, and a restaurant. Traveling on business? Take advantage of the business center, free WiFi in public areas, ...

9/10 Wonderful! (1,484 reviews)

"Very nice, spacious room with numerous convenience stores and restaurant choices nearby."

Reviewed on Nov 12, 2026

Hilton Key West Resort & Marina

5950 Peninsular Avenue Key West FL

Fully refundableReserve now, pay when you stay

$184 nightly

$208 total

Nov 15 - Nov 16

Total with taxes and fees

A marina, 6 outdoor pools, and a 24-hour gym are all featured at this smoke-free hotel. Traveling on business? Take advantage of the free WiFi in public areas ...

9/10 Wonderful! (1,795 reviews)

"Room was very nice size and clean. This hotel is tucked away and feels like a resort. Would definitely stay here again. Had dinner the last night in the hotel restaurant and food and service was great. Hourly free shuttles to the downtown area is super convenient."

Reviewed on Nov 13, 2026

Pier House Resort & Spa

1 Duval St Key West FL

Fully refundableReserve now, pay when you stay

$401 nightly

$451 total

Nov 28 - Nov 29

Total with taxes and fees

This smoke-free resort features a private beach, a full-service spa, and a restaurant. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. ...

Opal Key Resort & Marina, Key West

245 Front Street Key West FL

Fully refundableReserve now, pay when you stay

$294 nightly

$331 total

Nov 29 - Nov 30

Total with taxes and fees

A marina, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Enjoy the outdoor pool and visit the 3 bars/lounges and poolside bar for ...

DoubleTree Resort by Hilton Grand Key - Key West

3990 S Roosevelt Blvd Key West FL

Fully refundableReserve now, pay when you stay

$165 nightly

$186 total

Nov 29 - Nov 30

Total with taxes and fees

This resort features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public ...

Winslow's Bungalows - Key West Historic Inns

725 Truman Avenue Key West FL

Fully refundableReserve now, pay when you stay

$245 nightly

$276 total

Nov 17 - Nov 18

Total with taxes and fees

This smoke-free hotel features 3 outdoor pools, a bar/lounge, and a poolside bar. WiFi in public areas is free. Self parking, a garden, and luggage storage are ...

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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.

4 Star Hotels Fleming Key

Looking to live it up on your vacation with a bit of luxury? Or maybe you’ve decided that your boss can afford to put you up at a place of your choice on your next business trip?

Come on, you deserve it!

The best part about staying in Fleming Key 4 star hotels is that you’ll often be close to all the local sights and attractions. Whether you’re visiting the area for the first time or you’re back in town for more fun, a 4 star hotel is going to put you right in the heart of all the action.

Plus, you can rest easy knowing that you’re being well taken care of during your visit. Instead of worrying about where to eat or what to see, your friendly hotel staff will be happy to help you get whatever you need.

The best four star hotels in Fleming Key will also frequently include access to high-quality fitness centers and pools, so you’ll feel like you’re staying in an exclusive resort rather than a hotel. You won’t have any excuse for not keeping up with your workout routine!

If you’re looking for 4 star hotels in Fleming Key, you’ll find the most bang for your buck by booking your stay with Travelocity. Go explore a new city, and know you’re getting the best deal on a great hotel with the Travelocity Price Guarantee.