Sugarloaf Shores, FL

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.

Sugarloaf Shores Hotel Deals

Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
The price is ₩303,558 per night from Nov 15 to Nov 16
₩303,558
₩425,447 total
Nov 15 - Nov 16
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 ...
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 ₩201,488 per night from Nov 16 to Nov 17
₩201,488
₩310,968 total
Nov 16 - Nov 17
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! (1,890 reviews)
"Muy bien staff, excelente la predisposición de Jazmin en el front desk"

Reviewed on Oct 27, 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 ₩153,900 per night from Oct 29 to Oct 30
₩153,900
₩247,702 total
Oct 29 - Oct 30
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 ...
Blue Flamingo Resort Key West
Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
3841 N Roosevelt Blvd Key West FL
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. ...
Get rates
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 ₩142,420 per night from Oct 29 to Oct 30
₩142,420
₩203,050 total
Oct 29 - Oct 30
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. ...
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
The price is ₩326,580 per night from Oct 29 to Oct 30
₩326,580
₩457,013 total
Oct 29 - Oct 30
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 Southernmost ...
8.4/10 Very Good! (993 reviews)
"Thoroughly enjoyed our stay!"

Reviewed on Oct 28, 2026

Casa Marina Key West, Curio Collection by Hilton
See all 3,465 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 and neighborhoods 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 Cutthroat Harbor Estates isn't home to many top sights, Venture Key and Venture Out Keys are some notable places to visit nearby.

An aerial view of a bridge over turquoise water.

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.

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

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.

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 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.

Sugarloaf Shores, FL