Sugarloaf Shores

Summerland Key

A waterfront property with a pool, palm trees, and a building with a white roof.
A waterfront with a pier, calm water, and houses with palm trees in the background.
A cluster of palm trees with green fronds and some yellowing, under a partly cloudy sky.
A coastal property with a white and yellow house, surrounded by palm trees and a rocky shoreline.
A coastal view with houses and palm trees.

Top hotels in Sugarloaf Shores

Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Blvd Key West FL
The price is HK$1,640 per night from 12 Oct to 13 Oct
HK$1,640
HK$2,340 total
12 Oct - 13 Oct
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
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard Key West FL
The price is HK$927 per night from 12 Oct to 13 Oct
HK$927
HK$1,485 total
12 Oct - 13 Oct
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 ...
Blue Flamingo Resort Key West
Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
3841 N Roosevelt Blvd Key West FL
The price is HK$754 per night from 14 Oct to 15 Oct
HK$754
HK$1,598 total
14 Oct - 15 Oct
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! (2,592 reviews)
"Front desk people act like you bother them"

Reviewed on 8 Oct 2026

Beachside Resort & Residences
Havana Cabana at Key West

Havana Cabana at Key West

4 out of 5
3420 N. Roosevelt Blvd Key West FL
Fully refundable
The price is HK$1,107 per night from 25 Oct to 26 Oct
HK$1,107
HK$1,743 total
25 Oct - 26 Oct
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 ...
9/10 Wonderful! (1,870 reviews)
"Love it."

Reviewed on 8 Oct 2026

Havana Cabana at 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 HK$898 per night from 11 Oct to 12 Oct
HK$898
HK$1,264 total
11 Oct - 12 Oct
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 ...
Ibis Bay Beach Resort
Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

4 out of 5
1500 Reynolds Street Key West FL
Fully refundable
The price is HK$1,694 per night from 25 Oct to 26 Oct
HK$1,694
HK$2,436 total
25 Oct - 26 Oct
includes taxes & fees
Stay at this beach resort in Key West. Enjoy 2 outdoor pools, a full-service spa and a private beach. Popular attractions Duval Street and Southernmost Point ...
8.4/10 Very good! (957 reviews)
"I did hear roosters, but that's part of the charm of Key West. There was occasional chicken poop on the floors outside, so that's why I gave a 4 for cleanliness, but they do seem to clean it up fairly quickly. Overall I loved the stay. I will go again."

Reviewed on 7 Oct 2026

Casa Marina Key West, Curio Collection by Hilton
See all 3,428 properties in Sugarloaf Shores
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.

Where to stay in Sugarloaf Shores

Find the best Sugarloaf Shores areas for the activities you enjoy most.
A calm lake with several white birds, including herons and pelicans, on the water's edge.

Cutthroat Harbor Estates

While there might not be top attractions in Cutthroat Harbor Estates, you can explore the larger area and discover places like Venture Key and Venture Out Keys.

An aerial view of a bridge over turquoise water.

Cudjoe Gardens

While Cudjoe Gardens may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Upper Sugarloaf Key and Florida Keys Beaches.

An aerial view of a long bridge over turquoise waters with a few vehicles on it.

Bay Point

While Bay Point may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Lower Sugarloaf Sound and Florida Keys Beaches.

An aerial view of a coastal area with a long bridge connecting two landmasses, clear turquoise waters, and a clear blue sky with scattered clouds.

Breezeswept Beach Estates

While there might not be top attractions in Breezeswept Beach Estates, you can explore the larger area and discover places like Cook Island and Big Pine Key Flea Market.

Sugarloaf Shores