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.

Things to do


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
$265 nightly
The price is $298 total per night from Oct 19 to Oct 20
$298 total
Oct 19 - Oct 20
Total with taxes and 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! (1,800 reviews)
"All perfect!! Nice place"

Reviewed on Oct 18, 2026

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
$200 nightly
The price is $225 total per night from Nov 3 to Nov 4
$225 total
Nov 3 - Nov 4
Total with taxes and 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! (1,882 reviews)
"So Pretty and clean the place"

Reviewed on Oct 16, 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
$175 nightly
The price is $197 total per night from Oct 25 to Oct 26
$197 total
Oct 25 - Oct 26
Total with taxes and 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
$202 nightly
The price is $227 total per night from Oct 27 to Oct 28
$227 total
Oct 27 - Oct 28
Total with taxes and 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. ...
Beachside Resort & Residences
Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
3101 N. Roosevelt Blvd Key West FL
$202 nightly
The price is $228 total per night from Oct 20 to Oct 21
$228 total
Oct 20 - Oct 21
Total with taxes and 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! (2,408 reviews)
"Todo maravillosamente genial"

Reviewed on Oct 18, 2026

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
$276 nightly
The price is $310 total per night from Nov 1 to Nov 2
$310 total
Nov 1 - Nov 2
Total with taxes and 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 ...
Casa Marina Key West, Curio Collection by Hilton
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. Learn more about Sugarloaf Shores
Learn more about Sugarloaf Shores

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.



Sugarloaf Shores, FL

Choose one or more items to build your trip:

Explore a world of travel with Expedia