Explore top 2026 4 Star Hotels in Sugarloaf Shores

Name: Winslow's Bungalows - Key West Historic Inns
Price range: $482 total
Rating: 9.2

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Top Sugarloaf Shores 4 Star hotels

Blue Flamingo Resort Key West

3820 North Roosevelt Boulevard Key West FL

Fully refundableReserve now, pay when you stay

$409 nightly

$460 total

Jan 20 - Jan 21

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! (1,851 reviews)

No free breakfast

Reviewed on Jan 13, 2026

Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL

$530 nightly

$596 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

$662 nightly

$744 total

Jan 21 - Jan 22

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! (1,008 reviews)

Lovely location and goodnbreakfast

Reviewed on Jan 9, 2026

Oceans Edge Key West Resort, Hotel & Marina

5950 Peninsular Avenue Key West FL

Fully refundableReserve now, pay when you stay

$329 nightly

$370 total

Jan 20 - Jan 21

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! (1,772 reviews)

Although not a lot of amenities you didn't need to pay for, we enjoyed the option to be away from the craziness of Key West and still be able to enjoy it via the very convenient shuttle. Gorgeous resort - we will be back!

Reviewed on Jan 13, 2026

Margaritaville Beach House Key West

2001 South Roosevelt Boulevard Key West FL

$528 nightly

$594 total

Feb 9 - Feb 10

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

$419 nightly

$471 total

Jan 20 - Jan 21

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! (1,010 reviews)

Beautiful room

Reviewed on Jan 14, 2026

Parrot Key Hotel & Villas

2801 N Roosevelt Blvd Key West FL

Fully refundableReserve now, pay when you stay

$430 nightly

$484 total

Jan 20 - Jan 21

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! (1,230 reviews)

Beutiful place, friendly staff and great amenities. I would highly recommend this place to anyone. I would stay here again in the future.

Reviewed on Jan 14, 2026

Winslow's Bungalows - Key West Historic Inns

725 Truman Avenue Key West FL

Fully refundableReserve now, pay when you stay

$429 nightly

$482 total

Jan 20 - Jan 21

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! (1,116 reviews)

Clean room, all areas of property. Staff very accommodating, with exception of bar tender. Clean pools, tools always available. Nice breakfast area.

Reviewed on Jan 15, 2026

Casa Marina Key West, Curio Collection by Hilton

1500 Reynolds Street Key West FL

Fully refundableReserve now, pay when you stay

$569 nightly

$640 total

Jan 21 - Jan 22

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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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.