Sugarloaf Key Vacations from $480

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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.

The Latest Sugarloaf Key vacation packages

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
Price was $996, price is now $480 per person
$480
per person
Jan 8 - Jan 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (1,004 reviews)
We had a great stay at the Cavalier Hotel. The interior of the hotel is beautiful. They also have a bar area as well as breakfast, lunch, and dinner options for dine-in or take-out. The beach is only a few steps away! The hotel provided beach towels as well. Our room was clean and beds were comfortable. The bathroom doesn't have a proper door that locks. It's only a sliding door, which we found difficult for privacy. All the staff we met were also very friendly and helpful. The only note for anyone looking to stay at this property is that the hotel itself doesn't have any parking. There is a Municipal Parking Garage right around the corner from the hotel. We found it very convenient to park there (including overnight parking). It's open 24 hours, clean, has stairs and elevators to get to the street.

Reviewed on Oct 28, 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
Price was $16,772, price is now $7,504 per person
$7,504
per person
Jan 26 - Jan 30
found 20 hours ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8/10 Very Good! (1 review)
Park Central South Beach

Park Central South Beach

4 out of 5
South Beach
Price was $2,421, price is now $1,100 per person
$1,100
per person
Dec 3 - Dec 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.6/10 Excellent! (217 reviews)
The location is fabulous, the complimentary beach towels, chairs, + waters were very appreciated + a great added touch to the hotel! The front desk staff was all fantastic. Non-alcoholic drinks at the bar - 12$ USD for soda water, mint, + lime...not cool :( The guy at valet couldn't have been bothered in the least to look up from his phone to answer a question we had about parking, which is not a great look for this hotel either, and I would never oay 60$ USD a day when you can pat 25$ in a oarkade 2 blocks up. Air conditioning in room on the top floor is VERY loud. Showers need some sort of curtain.

Reviewed on Nov 2, 2025

The Penguin Hotel

The Penguin Hotel

3.5 out of 5
South Beach
Price was $1,544, price is now $741 per person
$741
per person
Dec 3 - Dec 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.2/10 Very Good! (1,491 reviews)
We had a quiet and pleasant stay at the Penguin it was very clean and accessible to the beach and the front desk personnel were all professional.

Reviewed on Nov 3, 2025

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Upper Sugarloaf Sound

Upper Sugarloaf Sound

Commune with nature and explore the great outdoors at Upper Sugarloaf Sound during your travels in Summerland Key.

Upper Sugarloaf Sound

Sugarloaf Beach

Why not spend a lazy afternoon at Sugarloaf Beach during your trip to Summerland Key?

Sugarloaf Beach

Upper Sugarloaf Key

4/5(21 reviews)

Commune with nature and explore the great outdoors at Upper Sugarloaf Key during your travels in Summerland Key.

Upper Sugarloaf Key

What to do in Sugarloaf Key

Marathon Backcountry Permit

Marathon Backcountry Fishing Charter

$667
per traveler
Marathon Backcountry Fishing Charter
See all activities in Sugarloaf Key

Sugarloaf Key Hotel Deals

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
$206 nightly
The price is $232 total per night from Nov 16 to Nov 17
$232 total
Nov 16 - Nov 17
Total with taxes and fees
8.8/10 Excellent! (1,733 reviews)
We’ve stayed here twice now. Staff is great, the shuttle into town is super convenient (hi Jeffrey!). We love that you can use the kayaks or paddleboards every day. The tiki hut crew is the best! The place is clean and I feel safe walking around there. It’s well lit and easy to navigate.

Reviewed on Nov 2, 2025

Oceans Edge Key West Resort, Hotel & Marina
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
$145 nightly
The price is $163 total per night from Dec 1 to Dec 2
$163 total
Dec 1 - Dec 2
Total with taxes and fees
7.8/10 Good! (1,648 reviews)
Beautiful room, great view, love the pools, bars and lawn games

Reviewed on Nov 3, 2025

Blue Flamingo Resort Key West
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
$196 nightly
The price is $220 total per night from Dec 1 to Dec 2
$220 total
Dec 1 - Dec 2
Total with taxes and fees
8.4/10 Very Good! (1,635 reviews)
A real nice hotel away from the crowds and real nice room decor .. Tavern n Town is an A+ restaurant

Reviewed on Oct 27, 2025

Beachside Resort & Residences
See all 3,544 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.

Find the Best Sugarloaf Key Vacation Packages

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

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Frequently asked questions

How much does a Sugarloaf Key vacation package cost?
Offering excellent value package deals from $480 on Expedia, you'll be thrilled with how little a vacation to Sugarloaf Key costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Sugarloaf Key?
April, September and October are great times to search for cheap Sugarloaf Key vacation packages. Choosing to travel in less busy periods means you can generally find lower prices on flights and accommodations.
How many days is enough for Sugarloaf Key?
For your Sugarloaf Key vacation, a few days will be enough to explore all the highlights. Be sure to visit Upper Sugarloaf Sound — it's one of the major sights in this destination. If you're looking for more activities, think about basing yourself here and venturing off on some day tours from Sugarloaf Key.
Is it worth booking a vacation package to Sugarloaf Key?
Sugarloaf Key has everything you need for a fantastic break — hiking, walking trails and nature are just the start. Whether you want to check out sights like Florida Keys Beaches and Sugarloaf Beach, or take the path less traveled, there's plenty to do on your Sugarloaf Key vacation.
How to find the best Sugarloaf Key package deals?
Start your search for a Sugarloaf Key package deal by entering your destination and preferred trip dates under our "Packages" tab. Then add a few filters, like "Popular locations" and "Amenities," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the ideal Sugarloaf Key package deal right away, just change your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Sugarloaf Key adventure off to a flying start.
Is it cheaper to book a Sugarloaf Key vacation as a package?
An Expedia vacation package could land you considerable savings when compared to booking flights and accommodations separately. Better still, you can customize your Sugarloaf Key getaway to match your exact style. Pick your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a vacation package to Sugarloaf Key?
If you're considering an impromptu Sugarloaf Key trip, browse our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can score sensational deals on your hotels and flights by booking ahead.
How to plan a trip to Sugarloaf Key?

  1. Choose when to go: Check your diary and pack your bags. Your favorite time of year and the available activities will also help you decide when to visit Sugarloaf Key.
  2. Calculate your budget: Make sure you have enough money to cover everything from food and transportation to airfares and activities. Your hotel will probably be the largest expense during your trip to Sugarloaf Key.
  3. Use our trip planning tool to explore Sugarloaf Key: Research every part of your trip to Sugarloaf Key with this handy planner. Invite your friends and family to collaborate on a group getaway, search for stays or things to do and make bookings.
  4. Work out your trip length: Consider how long you'd like to spend exploring Sugarloaf Key. Plan your itinerary so you can get to all the activities and attractions you're interested in without rushing.
  5. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. All that's left now is to find a Sugarloaf Key vacation package that brings all your bookings together.
  6. Book experiences or activities in advance: Whether it's a ticket to a major attraction or a walking tour, you won't have to worry about missing out on the highlights of Sugarloaf Key. Find all the incredible things to do in Sugarloaf Key with our dedicated travel guide.

Does Expedia offer Book Now, Pay Later Sugarloaf Key vacation packages?
Your Sugarloaf Key break is meant to be an escape from your daily routine, not a reason for money worries. So to allow you a little more flexibility, we've teamed up with online lender Affirm to offer you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and break down the cost over 3, 6 or 12 months. Plus, there aren't any late payment fees or hidden costs to worry about.

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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.