Sugarloaf Key Vacation Packages

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Your Sugarloaf Key Vacation

From its highlights to its hidden gems, this city is best explored with a Sugarloaf Key vacation package. Check out hotels located in Sugarloaf Shores, which is good for families, fishing and views. Make your trip to Sugarloaf Key even more exciting by including some sightseeing. Florida Keys Beaches, Sugarloaf Beach and Upper Sugarloaf Sound are among the major attractions you'll want to explore. No matter your travel plans or budget, putting together the ultimate tailored Sugarloaf Key vacation is simple with Expedia.

Top Sugarloaf Key Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Casablanca Miami Beach

Casablanca Miami Beach

3 out of 5
North Beach
Save 100% on your flight
per person
Jun. 19 - Jun. 24
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
5.8/10 (292 reviews)
The pool was nice, the condo was very basic but was fine. Until the pest control came to spray for roaches. We did not see any roaches during our stay but that did worry us for the rest of our stay. The building is aged but is in a good location.

Reviewed on Mar. 17, 2025

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. 14 - Jul. 18
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Miami (MIA)
8/10 Very Good! (1 review)
Amara Cay Resort

Amara Cay Resort

4 out of 5
Matecumbe
Save 100% on your flight
per person
Jun. 19 - Jun. 24
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
8.8/10 Excellent! (1,216 reviews)
Absolutely breath taking experience. The only thing I would recommend is for the property to have coffe and water available around the clock and for the pool to stay open past sun down.

Reviewed on Apr. 30, 2025

1 Hotel South Beach

1 Hotel South Beach

5 out of 5
South Beach
Save 100% on your flight
per person
Jul. 21 - Jul. 28
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Miami (MIA)
9.2/10 Wonderful! (1,097 reviews)
Great people and beautiful resort

Reviewed on Apr. 30, 2025

Hawks Cay Resort

Hawks Cay Resort

4 out of 5
Save 100% on your flight
per person
Jun. 19 - Jun. 24
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
7.8/10 Good! (1,006 reviews)
It was a great family resort

Reviewed on Apr. 23, 2025

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Sugarloaf Key Hotel Deals

Southernmost Beach Resort
Southernmost Beach Resort
4 out of 5
1319 Duval Street, Key West, FL
Fully refundableReserve now, pay when you stay
The price is CA $396 per night from May 11 to May 12
CA $396
CA $539 total
includes taxes & fees
May 11 - May 12
8.6/10 Excellent! (2,452 reviews)
"Great place to stay. Has it all. 3 pools, beach and more."

Reviewed on Apr. 29, 2025

Southernmost Beach Resort
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 CA $332 per night from May 18 to May 19
CA $332
CA $461 total
includes taxes & fees
May 18 - May 19
8.6/10 Excellent! (1,709 reviews)
"Had a great time thanks"

Reviewed on Apr. 29, 2025

Margaritaville Beach House Key West
Fairfield Inn and Suites by Marriott Key West
Fairfield Inn and Suites by Marriott Key West
3 out of 5
2400 N Roosevelt Blvd, Key West, FL
Fully refundableReserve now, pay when you stay
The price is CA $256 per night from May 26 to May 27
CA $256
CA $327 total
includes taxes & fees
May 26 - May 27
7.8/10 Good! (1,095 reviews)
"I was very excited about visiting this property and hanging out by the pool. However, we weren’t impressed with the friendliness of the staff who drove the shuttle and the pool bartender who closed the bar early with my husband standing there ready to order drinks during Spring Break week. The housekeeping ..."

Reviewed on Apr. 20, 2025

Fairfield Inn and Suites by Marriott Key West
See all 3,565 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

Family Vacations

Family 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 CA $753. 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.

What to do in Sugarloaf Key

Private Sandbar Adventure in Key West Backcountry

Private Sandbar Adventure in Key West Backcountry

CA $692
per traveller
Private Sandbar Adventure in Key West Backcountry
Photograph endangered Key Deer

Full-Day Tour of Florida Keys Including Aquarium Encounters from Key West

CA $206
per adult
Full-Day Tour of Florida Keys Including Aquarium Encounters from Key West
Marathon Backcountry Permit

Marathon Backcountry Fishing Charter

CA $923
per traveller
Marathon Backcountry Fishing Charter
See all activities in Sugarloaf Key
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.