Explore top 2026 4 Star Hotels in Lower Sugarloaf Key

Name: Winslow's Bungalows - Key West Historic Inns
Price range: $568 total
Rating: 9.2

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Top Lower Sugarloaf Key 4 Star hotels

Blue Flamingo Resort Key West

3820 North Roosevelt Boulevard Key West FL

Fully refundableReserve now, pay when you stay

$418 nightly

$470 total

Jan 25 - Jan 26

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 an arcade/game room, and families will appreciate ...

8/10 Very Good! (1,876 reviews)

First time staying here and would stay again! Came in to do 1/2 marathon, and have to stay, staff, shuttle, and the comfy room they sold me! Do you give repeat stay discounts?

Reviewed on Jan 20, 2026

Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL

Fully refundable

$511 nightly

$574 total

Jan 26 - Jan 27

Total with taxes and fees

This hotel features a full-service spa, 3 outdoor pools, and a restaurant. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Traveling ...

8.6/10 Excellent! (3,025 reviews)

Excellent location and outstanding service

Reviewed on Jan 15, 2026

Hyatt Centric Key West Resort and Spa

601 Front St Key West FL

$502 nightly

$564 total

Jan 25 - Jan 26

Total with taxes and fees

This smoke-free resort features a full-service spa, a marina, and a restaurant. Enjoy the outdoor pool and perks like free WiFi. Enjoy the 24-hour gym and unwind ...

8.8/10 Excellent! (1,002 reviews)

Clean room, nice staff

Reviewed on Jan 18, 2026

Oceans Edge Key West Resort, Hotel & Marina

5950 Peninsular Avenue Key West FL

Fully refundableReserve now, pay when you stay

$560 nightly

$630 total

Feb 8 - Feb 9

Total with taxes and fees

A marina, 6 outdoor pools, and a 24-hour gym are all featured at this smoke-free hotel. Business travelers can take advantage of the free WiFi in public areas. ...

8.8/10 Excellent! (1,780 reviews)

Had a wonderful view from our room. Shuttle is super convenient to Key West! Pools are very clean and live music was fantastic. Already booked for next year 😊

Reviewed on Jan 20, 2026

Margaritaville Beach House Key West

2001 South Roosevelt Boulevard Key West FL

$581 nightly

$654 total

Feb 10 - Feb 11

Total with taxes and fees

This hotel features a restaurant, an outdoor pool, and a bar/lounge. If you want to take your pet along, this pet-friendly property offers everything you'll ...

8.6/10 Excellent! (1,780 reviews)

Room was clean, staff was very friendly, bartenders were outstanding and Johnny, our shuttle driver was awesome.

Reviewed on Jan 16, 2026

The Perry Hotel & Marina Key West

7001 Shrimp Road Key West FL

Fully refundableReserve now, pay when you stay

$424 nightly

$477 total

Jan 26 - Jan 27

Total with taxes and fees

A marina, 2 restaurants, and 2 outdoor pools are all featured at this smoke-free hotel. Traveling for business? Take advantage of the free WiFi in public areas, ...

9.4/10 Exceptional! (1,196 reviews)

It was a nice place and the staff was super nice. The Champagne was a nice touch. Room had a few older things that need fixing but no big deal.

Reviewed on Jan 17, 2026

DoubleTree Resort by Hilton Grand Key - Key West

3990 S Roosevelt Blvd Key West FL

Fully refundableReserve now, pay when you stay

$379 nightly

$426 total

Jan 25 - Jan 26

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 ...

8/10 Very Good! (1,008 reviews)

Great Place

Reviewed on Jan 19, 2026

Parrot Key Hotel & Villas

2801 N Roosevelt Blvd Key West FL

Fully refundableReserve now, pay when you stay

$430 nightly

$484 total

Jan 28 - Jan 29

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, ...

8.8/10 Excellent! (1,241 reviews)

This is our favorite hotel in Key West. The staff is AMAZING! The rooms are spacious. Pools are heated. It's close to everything.

Reviewed on Jan 20, 2026

Winslow's Bungalows - Key West Historic Inns

725 Truman Avenue Key West FL

$505 nightly

$568 total

Jan 26 - Jan 27

Total with taxes and fees

This smoke-free hotel features 3 outdoor pools, a bar/lounge, and a poolside bar. Guests will appreciate free perks like continental breakfast and WiFi in public ...

9.2/10 Wonderful! (1,123 reviews)

Outstanding place. Great location minutes from Duval Street, walkable to everything. Room was safe, clean, updated, great shower and three pools all heated! Breakfast was a feast of so many options you have to limit yourself or you won't eat again that day. We didn't have a car but they had two big ...

Reviewed on Jan 19, 2026

Casa Marina Key West, Curio Collection by Hilton

1500 Reynolds Street Key West FL

Fully refundableReserve now, pay when you stay

$409 nightly

$460 total

Jan 22 - Jan 23

Total with taxes and fees

A private beach, a full-service spa, and 2 outdoor pools are all featured at this smoke-free resort. Relax with sun loungers and beach umbrellas, and cool off ...

8.2/10 Very Good! (515 reviews)

Friendly staff!

Reviewed on Jan 18, 2026

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4 Star Hotels Lower Sugarloaf 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 Lower Sugarloaf 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 Lower Sugarloaf 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 Lower Sugarloaf 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.