Sugarloaf Shores

Summerland Key

A waterfront property with a pool, palm trees, and a building with a white roof.
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.
A waterfront property with multiple houses, palm trees, and a calm sea.
A boat docked near a waterfront with a house and palm trees in the background.

Things to do


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 RM929 per night from 18 Nov to 19 Nov
RM929
RM1,303 total
18 Nov - 19 Nov
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
Havana Cabana at Key West

Havana Cabana at Key West

4 out of 5
3420 N. Roosevelt Blvd Key West FL
The price is RM572 per night from 29 Nov to 30 Nov
RM572
RM901 total
29 Nov - 30 Nov
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! (1,908 reviews)
"Excellent everything was fantastic staff and pool"

Reviewed on 9 Nov 2026

Havana Cabana at 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 RM508 per night from 15 Nov to 16 Nov
RM508
RM799 total
15 Nov - 16 Nov
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! (2,788 reviews)
"They have open passes for non paying people/locals on the weekend. Couldn't get a pool chair very crowed and screaming kids running around. Bill is incorrect too. Room didn't get cleaned Not happy ."

Reviewed on 10 Nov 2026

Blue Flamingo Resort Key West
Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
3841 N Roosevelt Blvd Key West FL
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. ...
Beachside Resort & Residences
Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
3101 N. Roosevelt Blvd Key West FL
The price is RM611 per night from 11 Nov to 12 Nov
RM611
RM818 total
11 Nov - 12 Nov
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
DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

4 out of 5
3990 S Roosevelt Blvd Key West FL
The price is RM565 per night from 29 Nov to 30 Nov
RM565
RM773 total
29 Nov - 30 Nov
includes taxes & fees
Stay at this business-friendly resort in Key West. Enjoy free Wi-Fi, breakfast (surcharge) and a free airport shuttle. Our guests praise the helpful staff and ...
DoubleTree Resort by Hilton Grand Key - Key West
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.

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.

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.

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