Sugarloaf Key Vacations from $361

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Your Sugarloaf Key Vacation

When a city break is calling, answer it with a vacation package to Sugarloaf Key. The neighborhood of Breezeswept Beach Estates, which is good for watersports, adventure sports and fishing, makes a great base for your adventures. If sightseeing is on the cards during your trip to Sugarloaf Key, visit top attractions like Florida Keys Beaches, Sugarloaf Beach and Upper Sugarloaf Sound. Whatever your travel plans or budget, putting together a tailored Sugarloaf Key vacation is a cinch with Expedia.

The Latest Sugarloaf Key Vacation Packages

Price found within the past 48 hours. Click for updated prices.
May-Dee Suites

May-Dee Suites

2.5 out of 5
Hollywood Hills
Save 100% on your flight
per person
Aug 25 - Aug 31
found 22 hours ago
Roundtrip flight included
New York (JFK) to Miami (MIA)
9.2/10 Wonderful! (1,280 reviews)
Really spacious rooms/suites with a super nice staff!

Reviewed on Jun 7, 2024

1 Hotel South Beach

1 Hotel South Beach

5 out of 5
South Beach
per person
Aug 10 - Aug 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
9/10 Wonderful! (1,004 reviews)
Beautiful property, the rooftop pool steals the show.

Reviewed on Jun 6, 2024

Holiday Isle Yacht Club

Holiday Isle Yacht Club

2.5 out of 5
East Fort Lauderdale
per person
Jul 17 - Jul 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
9.2/10 Wonderful! (72 reviews)
I love this property, I will come back. They have everything that I need. I have a relaxing weekend.

Reviewed on Jun 1, 2024

The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
South Beach
per person
Jul 25 - Jul 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
8/10 Very Good! (1 review)
Beachcomber Resort & Club

Beachcomber Resort & Club

4 out of 5
Save 100% on your flight
per person
Aug 21 - Aug 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
9/10 Wonderful! (1,388 reviews)
We love it! First time here had a wonderful time! Will definitely come back!

Reviewed on Jun 4, 2024

Sugarloaf Key Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Key West Intl. Airport (EYW)
Max Temp Winter
75ºF
Max Temp Summer
85ºF
Top Sights
Florida Keys Beaches, Boca Chica Nude Beach and Sugarloaf Beach

Sugarloaf Key Hotel Deals

Sugarloaf Key Hotel at KOA Resort
Sugarloaf Key Hotel at KOA Resort
2 out of 5
251 Co Rd 939, Summerland Key, FL
9.6/10 Exceptional! (165 reviews)
"My family and i stayed at this property during Memorial day weekend. The rooms are amazing!! very clean and spacious. the pool was very nice, and they had live music and drinks. we had an issue during check-in where my card was accidentally charged twice, but the staff was very responsive and were ..."

Reviewed on Jun 6, 2024

Get rates
Sugarloaf Key Hotel at KOA Resort
Oceans Edge Key West Resort, Hotel & Marina
Oceans Edge Key West Resort, Hotel & Marina
4 out of 5
5950 Peninsular Avenue, Key West, FL
Fully refundableReserve now, pay when you stay
The price is $167 per night from Jun 10 to Jun 11
$167
$246 total
includes taxes & fees
Jun 10 - Jun 11
8.8/10 Excellent! (1,535 reviews)
Beautiful Resort
"It was the nicest hotel we’ve ever stayed in and we’ve been married for 30+ years. We stay in 6-8 hotels a year. The courtesy was like non other."

Reviewed on Jun 5, 2024

Oceans Edge Key West Resort, Hotel & Marina
Margaritaville Beach House Key West
Margaritaville Beach House Key West
4 out of 5
2001 South Roosevelt Boulevard, Key West, FL
Fully refundableReserve now, pay when you stay
The price is $192 per night from Jun 27 to Jun 28
$192
$279 total
includes taxes & fees
Jun 27 - Jun 28
8.4/10 Very Good! (1,779 reviews)
"Staff was very welcoming and accommodating to our needs like late checkout etc"

Reviewed on Jun 6, 2024

Margaritaville Beach House Key West
See all 3,343 properties in Sugarloaf Key
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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does a Sugarloaf Key vacation package cost?
We make it simple to explore the world, with Sugarloaf Key vacation packages starting from just $361. You’ll have the flexibility to combine your preferred hotels, airlines and car rental. For the ultimate getaway, why not add a couple of experiences and tours to your itinerary?
How do I get a cheap travel package to Sugarloaf Key?
Bundle your hotels and flights with Expedia to save big bucks on your next exciting adventure. With more than 550 airlines and 1,000,000 hotels across the globe, your Sugarloaf Key vacation package can be customized exactly to suit your budget. With all that extra cash, why not add one or more awesome experiences and tours? It’s an easy way to unlock even more discounts. Your dream getaway to Sugarloaf Key is much closer than you thought!
Where should I stay in Sugarloaf Key?
It makes sense to stay near the action. Many travelers favor hotels around popular sights, like Florida Keys Beaches, Sugarloaf Beach and Upper Sugarloaf Sound.
What are the top hotels in Sugarloaf Key?
Sugar Loaf Lodge and Palms Resort - Green House are both well-liked options in the neighborhood of Sugarloaf Shores. If you want to stay in the Lower Sugarloaf Key area, consider getting a room at Paradise Found On Sugarloaf Key Please Call 704 or Tiki Palms - Amazing 4 Bedroom Sugarloaf Key Canal Home.
How far in advance should I book my Sugarloaf Key vacation?
Reserving your flight early with Expedia means one less thing to have to worry about. Many air carriers display prices up to 12 months in advance. Generally, this is the cheapest time to book. If circumstances have left you booking late, incredible deals to Sugarloaf Key are still known to appear in the weeks leading up to departure.
What does an Expedia Sugarloaf Key travel package include?
Expedia has everything you need to plan your Sugarloaf Key trip, but how you structure your package is your choice. Pick from any combination of rental cars, hotels and flights. After some tours or activities to keep you on the go? Once you’ve made your booking, you can add them too. Whatever your style or budget, there’s a package to match your needs.
What should I know before booking a Sugarloaf Key travel package?
Bundling your bookings into a Sugarloaf Key vacation package is the most convenient way to organize your trip. Not only that, you’ll save just for combining your flights, hotels and car rentals. Once you’ve booked, why not add on an activity or a tour?
If I'm not able to travel, can I cancel my Sugarloaf Key vacation package?
Don’t worry if you’re rethinking your Sugarloaf Key vacation package — you can cancel or change your booking. And if you’ve booked it within the last 24 hours, you may be able to do it at no cost. However, bookings made more than 24 hours ago may incur a fee from your hotel, airline or car rental company. We know life can sometimes throw a spanner in the works, so look up our Customer Service Portal if that occurs. When you’re ready to make changes, we’ll be here to help.

Discover the most popular places to visit in Sugarloaf Key

Image for Key West Golf Club

Key West Golf Club

4/5(52 reviews)

Play a round of golf in Key West at Key West Golf Club, and enjoy other activities such as boating. Amble around the area's seaside or seek out the biking trails.

Key West Golf Club
Image for Florida Keys Beaches

Florida Keys Beaches

4/5(519 reviews)

Why not spend a lazy afternoon at Florida Keys Beaches during your trip to Long Beach Estates?

Florida Keys Beaches
Image for Stock Island Yacht Club & Marina

Stock Island Yacht Club & Marina

4.5/5(2,254 reviews)

Explore the waterfront of Stock Island Yacht Club & Marina and enjoy activities such as boating in Key West. Discover the area's beautiful sunsets and lively bars.

Stock Island Yacht Club & Marina

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.