Sugarloaf Shores, FL

Summerland Key

Sugarloaf Shores featuring a bay or harbor
Sugarloaf Shores showing a bay or harbor and a sunset
Sugarloaf Shores featuring a sunset and tropical scenes
Sugarloaf Shores which includes a bay or harbor and a house
Sugarloaf Shores showing a house, a sunset and a bay or harbor

Sugarloaf Shores Hotel Deals

Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
3841 N Roosevelt Blvd Key West FL
The price is ￥21,820 per night from Dec 2 to Dec 3
￥21,820
￥32,453 total
Dec 2 - Dec 3
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. ...
8.6/10 Excellent! (1,720 reviews)
Great room, restaurant, and shuttle!

Reviewed on Nov 26, 2025

Beachside Resort & Residences
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard Key West FL
The price is ￥14,900 per night from Nov 30 to Dec 1
￥14,900
￥25,547 total
Nov 30 - Dec 1
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 ...
7.8/10 Good! (1,730 reviews)
Everything was beautiful and it was a pleasure to stay there. Will stay again.

Reviewed on Nov 25, 2025

Blue Flamingo Resort Key West
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
5950 Peninsular Avenue Key West FL
The price is ￥23,139 per night from Nov 30 to Dec 1
￥23,139
￥35,428 total
Nov 30 - Dec 1
includes taxes & fees
Book a stay at this luxury hotel in Key West. Enjoy free WiFi, 6 outdoor pools, and a marina. Our guests praise the pool and the restaurant in our reviews. Popular ...
8.8/10 Excellent! (1,748 reviews)
The property was beautiful. The staff was welcoming and helpful. The room and accommodations were wonderful. Enjoyed the convenience of the concierge services as well as the shuttle. Everyone from the bellmen Sam to the shuttle drivers were friendly and made the time spent on property a joy.

Reviewed on Nov 25, 2025

Oceans Edge Key West Resort, Hotel & Marina
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
The price is ￥25,295 per night from Dec 2 to Dec 3
￥25,295
￥39,885 total
Dec 2 - Dec 3
includes taxes & fees
Book a stay at this beach hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
8.6/10 Excellent! (2,881 reviews)
A1

Reviewed on Nov 24, 2025

Southernmost Beach Resort and Guesthouses
Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Boulevard Key West FL
The price is ￥30,924 per night from Dec 17 to Dec 18
￥30,924
￥44,625 total
Dec 17 - Dec 18
includes taxes & fees
Book a stay at this beach hotel in Key West. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the pool and the restaurant ...
8.6/10 Excellent! (1,789 reviews)
Property was very clean and maintained. The restaurant and bars offered great drinks and food, room service was also very nice to have. Access to the nicest beach on key west was perfect. Far enough out of town yet close enough to get into the nightlife. Would definitely stay again.

Reviewed on Nov 19, 2025

Margaritaville Beach House Key West
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
7001 Shrimp Road Key West FL
The price is ￥20,100 per night from Dec 14 to Dec 15
￥20,100
￥31,625 total
Dec 14 - Dec 15
includes taxes & fees
Book a stay at this business-friendly hotel in Key West. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff ...
9.4/10 Exceptional! (1,159 reviews)
Great Hotel will, clean, great staff, wonderful view in the am. The shuttle service to downtown Key West is the a game changer. Will repeat again.

Reviewed on Nov 26, 2025

The Perry Hotel & Marina Key West
See all 3,520 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.

Other neighborhoods around Sugarloaf Shores

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Cudjoe Gardens

When in Cudjoe Gardens, you can plan a visit to Upper Sugarloaf Key and Venture Out Keys, some noteworthy sights in the nearby area.

Cudjoe Gardens
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Cutthroat Harbor Estates

While Cutthroat Harbor Estates isn't home to many top sights, Venture Out Keys and Upper Sugarloaf Key are some notable places to visit nearby.

Cutthroat Harbor Estates
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Breezeswept Beach Estates

While Breezeswept Beach Estates isn't home to many top sights, Cook Island and Venture Out Keys are some notable places to visit nearby.

Breezeswept Beach Estates

Sugarloaf Shores, FL