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.
iCoconutGrove Vacation Rentals

iCoconutGrove Vacation Rentals

4 out of 5
Coconut Grove
Save 100% on your flight
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
9.2/10 Wonderful! (1,000 reviews)
The property was in a very populated area with lots of shops, restaurants and nightlife (if that’s your thing). The studio was very clean and there were no issues at all. Unlike hotel rooms, I could not hear what was happening right next door, so it was quiet as well. I would stay here again.

Reviewed on Jul. 12, 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
Aug 24 - Aug 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
8/10 Very Good! (1 review)
Pelican Grand Beach Resort - A Noble House Resort

Pelican Grand Beach Resort - A Noble House Resort

4 out of 5
East Fort Lauderdale
Save 100% on your flight
per person
Sep 28 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Miami (MIA)
8.6/10 Excellent! (1,119 reviews)
My family and I loved it , perfect place to vacation!

Reviewed on Jul. 16, 2025

Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
Save 100% on your flight
per person
Sep 28 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Miami (MIA)
8.4/10 Very Good! (1,001 reviews)
Great location and friendly staff

Reviewed on Jul. 18, 2025

1 Hotel South Beach

1 Hotel South Beach

5 out of 5
South Beach
Save 100% on your flight
per person
Sep 28 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Miami (MIA)
9.4/10 Exceptional! (1,212 reviews)
Miami Beach as it is supposed to be.

Reviewed on Jul. 18, 2025

Ready to book your vacation to Sugarloaf Key?

 

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Sugarloaf Key Hotel Deals

Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
3841 N Roosevelt Blvd, Key West, FL
Fully refundableReserve now, pay when you stay
The price is CA $184 per night from Jul 20 to Jul 21
CA $184
CA $277 total
Jul 20 - Jul 21
includes taxes & fees
8.4/10 Very Good! (1,348 reviews)
"Like the resort.a little mixed with residential residents & hotel. Over all very well. My dislike that there's nothing walkable distance during the hot temperatures"

Reviewed on Jul. 18, 2025

Beachside Resort & Residences
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street, Key West, FL
Fully refundable
The price is CA $273 per night from Aug 4 to Aug 5
CA $273
CA $400 total
Aug 4 - Aug 5
includes taxes & fees
8.6/10 Excellent! (2,613 reviews)
"Enjoyed our stay very much."

Reviewed on Jul. 18, 2025

Southernmost Beach Resort and Guesthouses
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard, Key West, FL
Fully refundableReserve now, pay when you stay
The price is CA $167 per night from Aug 17 to Aug 18
CA $167
CA $265 total
Aug 17 - Aug 18
includes taxes & fees
7.6/10 Good! (1,468 reviews)
"Pools little bus"

Reviewed on Jul. 17, 2025

Blue Flamingo Resort Key West
See all 3,500 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

What to do in Sugarloaf Key

Private Sandbar Adventure in Key West Backcountry

Private Sandbar Adventure in Key West Backcountry

CA $683
per traveller
Private Sandbar Adventure in Key West Backcountry
Sandbar Fun - Tiki Style

Key West Tiki Bar Boat Cruise to Popular Sand Bar

CA $771
per traveller
Key West Tiki Bar Boat Cruise to Popular Sand Bar
See all activities in Sugarloaf Key

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 $785. 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.