Sugarloaf Key Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

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.
Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
Save 100% on your flight
per person
Aug 13 - Aug 20
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Miami (MIA)
8.4/10 Very Good! (1,000 reviews)
Perfectly located on Ocean Drive with an old-school Art Deco vibe that feels both historic and fresh. The room was spotless, the A/C was ice cold, and the bed was genuinely comfortable. Staff was friendly and helpful. You’re across from the beach, but it still feels like a quiet escape. Would absolutely stay here again.

Reviewed on Jul. 1, 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
Sep 11 - Sep 16
found 1 day ago
Roundtrip flight included
Toronto (YYZ) 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
per person
Aug 11 - Aug 18
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Miami (MIA)
8.6/10 Excellent! (1,119 reviews)
The beach was beautiful

Reviewed on Jul. 11, 2025

The Shelborne By Proper

The Shelborne By Proper

4 out of 5
South Beach
Save 100% on your flight
per person
Sep 17 - Sep 23
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Miami (MIA)
9.6/10 Exceptional! (4 reviews)
Wonderful hotel. Beautiful design and very attentive staff.

Reviewed on Jul. 7, 2025

President Hotel

President Hotel

3.5 out of 5
South Beach
Save 100% on your flight
per person
Aug 13 - Aug 20
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Miami (MIA)
8.4/10 Very Good! (1,596 reviews)
It was good, the one who attended us at check in was quite friendly and at breakfast anyway everything was good, very kind... I didn't like it was that we tried to get a glass of hot water and although it was only a "question" she replied "right now I'm very busy, come back in 10 minutes". On the day of cleaning, the one who was going to clean looked at me super badly "I knew that we can't be in the room when they go to do cleaning" but she was not nice at all and we were just about to leave the room...

Reviewed on Jul. 11, 2025

Ready to book your vacation to Sugarloaf Key?

 

Choose your dates

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 $193 per night from Jul 20 to Jul 21
CA $193
CA $287 total
Jul 20 - Jul 21
includes taxes & fees
8.4/10 Very Good! (1,307 reviews)
"Everything was great"

Reviewed on Jul. 9, 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 $272 per night from Aug 4 to Aug 5
CA $272
CA $398 total
Aug 4 - Aug 5
includes taxes & fees
8.6/10 Excellent! (2,611 reviews)
"Love this property; property is bigger than I thought but had so much to offer; had fun activities if you wanted to be involved; a block from southern most point; everything is so close to stay"

Reviewed on Jul. 9, 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 11 to Aug 12
CA $167
CA $264 total
Aug 11 - Aug 12
includes taxes & fees
7.6/10 Good! (1,454 reviews)
"This resort was great. Staff was very helpful and accommodating. Irina at the bar was incredible! The shuttle service was perfect for an easy ride down to Duval. Would definitely stay here again!"

Reviewed on Jul. 11, 2025

Blue Flamingo Resort Key West
See all 3,504 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

A fun-filled adventure for the whole family

Guided Clear Kayak Eco-Tour Near Key West

CA $109
per adult
Guided Clear Kayak Eco-Tour Near Key West
Private Sandbar Adventure in Key West Backcountry

Private Sandbar Adventure in Key West Backcountry

CA $687
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 $779. 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.