Sugarloaf Key Vacations from $493

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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 $1,073, price is now $493 per person
$493
per person
Feb 24 - Feb 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (1,001 reviews)
Perfect location and great bonus with beach towels and two free chairs on the beach.

Reviewed on Dec 27, 2025

Creekside Inn

Creekside Inn

2.5 out of 5
Price was $1,738, price is now $662 per person
$662
per person
Feb 1 - Feb 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8/10 Very Good! (1,004 reviews)
It is an awesome experience with wonderful views, the location is a big advantage for this hotel

Reviewed on Jan 1, 2026

Flow Miami Hotel

Flow Miami Hotel

3.5 out of 5
Downtown Miami
Price was $2,778, price is now $1,200 per person
$1,200
per person
Mar 7 - Mar 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9.2/10 Wonderful! (172 reviews)
Beautiful. Whole building smelled great.

Reviewed on Dec 29, 2025

The Shelborne By Proper, a Member of Design Hotels

The Shelborne By Proper, a Member of Design Hotels

4 out of 5
South Beach
Price was $1,763, price is now $791 per person
$791
per person
Feb 24 - Feb 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9.4/10 Exceptional! (56 reviews)
Excellent amenities and great location

Reviewed on Dec 31, 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 $11,980, price is now $5,468 per person
$5,468
per person
Feb 24 - Feb 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8/10 Very Good! (1 review)
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Discover the most popular places to visit in Sugarloaf Key

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

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

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
$322 nightly
The price is $363 total per night from Jan 19 to Jan 20
$363 total
Jan 19 - Jan 20
Total with taxes and fees
8.4/10 Very Good! (1,858 reviews)
The grounds are beautiful. Our room was a smaller room and it was nice but some things didn’t work properly. The toilet didn’t flush well, the shower head would turn on when filling the bathtub, tv would turn off randomly and the floors were dirty. Reasonably price in comparison to other places in ...

Reviewed on Jan 1, 2026

Beachside Resort & Residences
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
$292 nightly
The price is $329 total per night from Jan 4 to Jan 5
$329 total
Jan 4 - Jan 5
Total with taxes and fees
8/10 Very Good! (1,803 reviews)
The room was very clean and comfortable. The $15.00 for parking your car was a little of the top tho! You should really give discounts for Florida Residence too, we drove 350 miles to come see Key West and to have to pay all the fees & parking fee is a bit much!

Reviewed on Dec 26, 2025

Blue Flamingo Resort Key West
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
$273 nightly
The price is $307 total per night from Jan 11 to Jan 12
$307 total
Jan 11 - Jan 12
Total with taxes and fees
8.8/10 Excellent! (1,763 reviews)
So many activities and amazing staff and service. The shuttle was very convenient. I would stay here again! Perfect for families. I felt safe. Very laid back environment.

Reviewed on Dec 26, 2025

Oceans Edge Key West Resort, Hotel & Marina
See all 3,553 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 $493 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.