Sugarloaf Shores
Summerland Key
Visit Sugarloaf Shores
Things to do
Discover US East Coast Self Guided Audio Tour
CA $203
per traveller
Private Sandbar Adventure in Key West Backcountry
CA $699
per traveller
Luxury Sandbar and Snorkeling trip in Key West
CA $1,678
per traveller
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
CA $78
per adult
88% of travellers recommend
Sugarloaf Shores Hotel Deals
Margaritaville Beach House Key West
2001 South Roosevelt Blvd Key West FL
The price is CA $297 per night from Oct 12 to Oct 13
CA $297
CA $424 total
Oct 12 - Oct 13
includes taxes & fees
Book a 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 ...
8.8/10 Excellent! (1,792 reviews)
"Staff was great! Rooms were clean! Had a great stay!"
Reviewed on Oct 6, 2026
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
The price is CA $168 per night from Oct 11 to Oct 12
CA $168
CA $269 total
Oct 11 - Oct 12
includes taxes & fees
Book a stay at this family-friendly hotel in Key West. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff ...
Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
The price is CA $133 per night from Oct 8 to Oct 9
CA $133
CA $286 total
Oct 8 - Oct 9
includes taxes & fees
Book a stay at this beach hotel in Key West. Enjoy free WiFi, 2 restaurants, and a private beach. Our guests praise the pool and the helpful staff in our reviews. ...
Havana Cabana at Key West
3420 N. Roosevelt Blvd Key West FL
The price is CA $214 per night from Oct 8 to Oct 9
CA $214
CA $331 total
Oct 8 - Oct 9
includes taxes & fees
Book a stay at this business-friendly hotel in Key West. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the helpful ...
9/10 Wonderful! (1,870 reviews)
"The only thing that I didn’t like was the bar staff"
Reviewed on Oct 7, 2026
Ibis Bay Beach Resort
3101 N. Roosevelt Blvd Key West FL
The price is CA $177 per night from Oct 8 to Oct 9
CA $177
CA $245 total
Oct 8 - Oct 9
includes taxes & fees
Book a stay at this beach hotel in Key West. Enjoy free breakfast, free WiFi, and a private beach. Our guests praise the breakfast and the pool in our reviews. ...
8.2/10 Very good! (2,406 reviews)
"Very nice and staff was great."
Reviewed on Oct 6, 2026
Casa Marina Key West, Curio Collection by Hilton
1500 Reynolds Street Key West FL
The price is CA $308 per night from Oct 25 to Oct 26
CA $308
CA $443 total
Oct 25 - Oct 26
includes taxes & fees
Book a 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 South Beach ...
8.4/10 Very good! (955 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 Oct 7, 2026
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 and neighborhoods for the activities you enjoy most.
Cutthroat Harbor Estates
While Cutthroat Harbor Estates isn't home to many top sights, Venture Key and Venture Out Keys are some notable places to visit nearby.
Cudjoe Gardens
When in Cudjoe Gardens, you can plan a visit to Upper Sugarloaf Key and Florida Keys Beaches, some noteworthy sights in the nearby area.
Bay Point
Bay Point might not have many top sights, but Lower Sugarloaf Sound and Florida Keys Beaches are two attractions nearby that you can check out.
Breezeswept Beach Estates
While Breezeswept Beach Estates isn't home to many top sights, Cook Island and Big Pine Key Flea Market are some notable places to visit nearby.
