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.

Things to do


Top hotels in Sugarloaf Shores

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
The price is S$343 per night from 28 Sept to 29 Sept
S$343
28 Sept - 29 Sept
includes taxes & fees
Stay at this spa 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! (3,606 reviews)
"The property was very confusing to get around. The main pool was closed and so was the beach. The hotel was nice , clean, the pool at the pineapple bar was covered in film. Needed cleaned."

Reviewed on 16 Sept, 2026

Southernmost Beach Resort and Guesthouses
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard Key West FL
The price is S$228 per night from 20 Sept to 21 Sept
S$228
20 Sept - 21 Sept
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 ...
8.6/10 Excellent! (2,674 reviews)
"It was a nice hotel. It was very clean quiet they had two Swimming Pool pools so that made it nice for the kids at one pool primarily and the adults at the other the walk-up bars were nice and close."

Reviewed on 16 Sept, 2026

Blue Flamingo Resort Key West
Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Blvd Key West FL
The price is S$334 per night from 7 Oct to 8 Oct
S$334
7 Oct - 8 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
Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
3101 N. Roosevelt Blvd Key West FL
The price is S$186 per night from 17 Sept to 18 Sept
S$186
17 Sept - 18 Sept
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 ...
8.2/10 Very good! (2,385 reviews)
"Had a great time here."

Reviewed on 16 Sept, 2026

Ibis Bay Beach Resort
Havana Cabana at Key West

Havana Cabana at Key West

4 out of 5
3420 N. Roosevelt Blvd Key West FL
The price is S$238 per night from 1 Oct to 2 Oct
S$238
1 Oct - 2 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 ...
Havana Cabana at Key West
Pier House Resort & Spa

Pier House Resort & Spa

4 out of 5
1 Duval St Key West FL
The price is S$374 per night from 30 Sept to 1 Oct
S$374
30 Sept - 1 Oct
includes taxes & fees
Stay at this beach resort in Key West. Enjoy a full-service spa, a private beach and 2 bars/lounges. Our guests praise the pool and the helpful staff in their ...
Pier House Resort & Spa
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.

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.

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.

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.

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 Pye Key.



Sugarloaf Shores