Sugarloaf Shores Holidays from AU$2,258

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Your Sugarloaf Shores Holiday

Your next big journey is calling out to you with a holiday package to Sugarloaf Shores. Excitement, fun and great times — you're bound to find it in this neighbourhood. When the time comes to see the sights, your trip to Sugarloaf Shores has to include a visit to Sugarloaf Beach and Upper Sugarloaf Sound. Expedia is here to help put your travel plans into action. Book your ultimate Sugarloaf Shores holiday today.

Top Holiday Package Deals in Sugarloaf Shores

Price found within the past 48 hours. Click for updated prices.
The Grayson Miami Downtown

The Grayson Miami Downtown

4.5 out of 5
Downtown Miami
Price was AU$2,872, price is now AU$2,258 per person
AU$2,258
per person
1 Oct - 8 Oct
found 15 hours ago
Return flight included
Sydney (SYD) to Miami (MIA)
8.8/10 Excellent! (1,947 reviews)

Fontainebleau Miami Beach

Fontainebleau Miami Beach

4.5 out of 5
Mid Beach
Price was AU$4,291, price is now AU$3,071 per person
AU$3,071
per person
1 Oct - 8 Oct
found 15 hours ago
Return flight included
Sydney (SYD) to Miami (MIA)
8.4/10 Very good! (8,482 reviews)
LOVE IT HERE! Cant wait to go back!!

Reviewed on 16 July 2026

Eden Roc Miami Beach

Eden Roc Miami Beach

4.5 out of 5
Mid Beach
Price was AU$3,886, price is now AU$2,863 per person
AU$2,863
per person
1 Oct - 8 Oct
found 15 hours ago
Return flight included
Sydney (SYD) to Miami (MIA)
8.6/10 Excellent! (3,309 reviews)

Unique Escape GameRoom! Bar, BBQ, Spacious, and Near Beach

Unique Escape GameRoom! Bar, BBQ, Spacious, and Near Beach

5 out of 5
Coral Way
Price was AU$4,085, price is now AU$3,174 per person
AU$3,174
per person
1 Oct - 8 Oct
found 15 hours ago
Return flight included
Sydney (SYD) to Miami (MIA)
10/10 Exceptional! (2 reviews)
Family of 10 for birthday celebration, ages from 1 to 51 this house had something for everyone. Backyard setup is next level and beds are very comfortable. Highly recommended.

Reviewed on 10 June 2025

4 to 23 Guests GameRoom 2 Kitchens BAR BBQ

4 to 23 Guests GameRoom 2 Kitchens BAR BBQ

3.5 out of 5
Coral Way
Price was AU$5,965, price is now AU$4,740 per person
AU$4,740
per person
1 Oct - 8 Oct
found 15 hours ago
Return flight included
Sydney (SYD) to Miami (MIA)
10/10 Exceptional! (1 review)
Awesome, well maintained property. We were group of 19ppl with ages from 12-80, and everyone had great time at the property. Kids had fun with the arcade, video games and poker table. Kitchen fully functional, very effective AC.

Reviewed on 24 June 2025

Our guide on 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
A calm lake with several white birds, including herons and pelicans, on the water's edge.

Cutthroat Harbor Estates

While there might not be top attractions in Cutthroat Harbor Estates, you can explore the larger area and discover places like Venture Out Keys and Upper Sugarloaf Key.

Find hotels in Cutthroat Harbor Estates

Our pick of the best Sugarloaf Shores 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 AU$325 per night from 17 Aug to 18 Aug
AU$325
17 Aug - 18 Aug
includes taxes & fees
8.6/10 Excellent! (2,348 reviews)
"Check in could have been better. We arrived early and was told we would be notified when our room was ready but no one notified us. I had to check again on my own after waiting for hours in the lobby. Room was clean, but the bathroom door handle came off when I tried to close the door, the sink had ..."

Reviewed on 16 July 2026

Beachside Resort & Residences
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
Fully refundableReserve now, pay when you stay
The price is AU$397 per night from 5 Aug to 6 Aug
AU$397
5 Aug - 6 Aug
includes taxes & fees
8.8/10 Excellent! (3,471 reviews)
"/"

Reviewed on 17 July 2026

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 AU$287 per night from 16 Aug to 17 Aug
AU$287
16 Aug - 17 Aug
includes taxes & fees
8.4/10 Very good! (2,539 reviews)
"Wonderful hotel! A lot of things to do there. Shuttle bus was a plus. The only thing that I had a problem with was housekeeping. I had to call consistently for towels and also for them to pick up the garbage. And it will take a long time for them to come to the room. They never clean the bathroom ..."

Reviewed on 16 July 2026

Blue Flamingo Resort Key West
See all 3,433 properties in Sugarloaf Shores
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 Holidays
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Frequently asked questions

How much does a Sugarloaf Shores holiday package cost?
From just AU$2,258, you can tailor your Sugarloaf Shores package the way you want. Simply bundle hotels, flights and car rentals and be rewarded with discounts.
How do I get a cheap travel package to Sugarloaf Shores?
One of the simplest ways to save money (and time) is to bundle your bookings with Expedia. Flights, rental cars, hotels and activities — we've got them all covered. Select the combination that best suits you and watch your savings pile up. We know a travel package is never one-size-fits-all. That's why Expedia offers over 550 air carriers and 1 000 000 properties throughout the world, which lets you customize your Sugarloaf Shores holiday.
Where should I stay in Sugarloaf Shores?
A holiday in Sugarloaf Shores isn't complete without seeing Sugarloaf Beach, Upper Sugarloaf Sound and Upper Sugarloaf Key. Spend your evenings close to these popular attractions and make sightseeing simple.
What are the top hotels in Sugarloaf Shores?
South Point Sunset - Florida Keys Waterfront 3 and Paradise Point - Amazing Views are among the most well-known properties in Sugarloaf Shores. Why not look up the rates and amenities at each and then decide?
How far in advance should I book my Sugarloaf Shores holiday?
While not all airlines advertise tickets early, you can usually start comparing international flights on Expedia up to 12 months in advance. This is the time when you'll score some incredible bargains. If you've left things to the last minute, you might get lucky. Discounted prices occasionally appear just weeks prior to departure.
What does an Expedia Sugarloaf Shores travel package include?
That mostly depends on you. You can pick from a variety of Sugarloaf Shores packages, such as a rental car, flight and hotel. You can also book a flight and a hotel, or a flight with a rental car. Once you've made your booking, you can add on the fun stuff like tours and activities. Whatever your perfect Sugarloaf Shores break looks like, you'll save!
What should I know before booking a Sugarloaf Shores travel package?
You'll score great savings when you combine your hotels, flights and rental cars into a package. Not only that, booking everything in one spot will make your trip planning easier. So why waste time or money? Whether you're putting together a fancy romantic getaway or a budget solo adventure, take a look at our holiday packages today.
Can I choose my airline with a Sugarloaf Shores Expedia holiday package?
With a holiday package, the choice is in your hands. Whether you're looking to fly to Sugarloaf Shores in business or coach, simply select from the available airline options. Expedia has access to more than 550 partner airlines around the world.
If I'm not able to travel, can I cancel my Sugarloaf Shores holiday package?
Yes, it's possible to cancel your Sugarloaf Shores booking if your travel plans have changed. Whether you'll incur a fee or not depends on your airline, hotel or car rental company. You may be able to change or cancel your booking free of charge if you booked in the last 24 hours. Visit our Customer Service Portal for more information.

Activities

Guided Clear Kayak Eco-Tour Near Key West

Guided Clear Kayak Eco-Tour Near Key West

AU$129
per adult
Guided Clear Kayak Eco-Tour Near Key West
Guided Mangrove Eco Tours Kayak or Paddleboard Adventure

Guided Mangrove Eco Tours Kayak or Paddleboard Adventure

AU$109
per adult
Guided Mangrove Eco Tours Kayak or Paddleboard Adventure
Private Sandbar Adventure in Key West Backcountry

Private Sandbar Adventure in Key West Backcountry

AU$795
per traveller
Private Sandbar Adventure in Key West Backcountry
See all activities in Summerland Key
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.