Sugarloaf Shores, FL

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.

Travel to Sugarloaf Shores for sun-drenched beaches, local charm, and engaging activities that showcase the area's unique character.

Sugarloaf Shores is an ideal destination for outdoor, beach travelers. You can explore the nearby Florida Keys Beaches for sun and sand, or visit Sugarloaf Beach, another nearby option for a relaxing day by the water. For those interested in local life, Upper Sugarloaf Key offers a glimpse into the nearby town's atmosphere. Additionally, engaging in water sports at Pigeon Key, golfing at the Key West Golf Club, or taking a tour of the Papa's Pilar Rum Distillery are all nearby activities that enhance your experience.

While you're in Sugarloaf Shores, take time to wander its nearby neighborhoods, each with its own character. Bay Point is known for outdoor, family experiences, offering various recreational opportunities. Big Coppitt Key also caters to outdoor, beach experiences, featuring places like Wilhelmina Harvey Park and nearby islands such as Shark Key and East Rockland Key. Cudjoe Gardens is another nearby area known for its city and family experiences, making it a great spot to explore.

The best time to visit Sugarloaf Shores is from June to September when the weather is warm, with temperatures averaging 83 to 84°F. During this period, the weather is mostly dry and often sunny, making it ideal for outdoor activities. Demand for accommodations remains fairly steady throughout the year, but it tends to be a little quieter from October to December, allowing for a more relaxed experience during those months.


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
$285 nightly
The price is $321 total per night from Nov 18 to Nov 19
$321 total
Nov 18 - Nov 19
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 ...
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
$171 nightly
The price is $192 total per night from Nov 29 to Nov 30
$192 total
Nov 29 - Nov 30
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 ...
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 Nov 15 to Nov 16
$197 total
Nov 15 - Nov 16
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 ...
8.6/10 Excellent! (2,797 reviews)
"Todo estaba en buenas condiciones y limpio. Valoración precio calidad ."

Reviewed on Nov 14, 2026

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. ...
Beachside Resort & Residences
Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
3101 N. Roosevelt Blvd Key West FL
$230 nightly
The price is $259 total per night from Dec 15 to Dec 16
$259 total
Dec 15 - Dec 16
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! (2,425 reviews)
"Good location, decent breakfast"

Reviewed on Nov 14, 2026

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
$165 nightly
The price is $186 total per night from Nov 29 to Nov 30
$186 total
Nov 29 - Nov 30
Total with taxes and fees
Book a stay at this business-friendly resort in Key West. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
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 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

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