Sugarloaf Key Vacations from $586

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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.
Hawks Cay Resort

Hawks Cay Resort

4 out of 5
Price was $1,506, price is now $586 per person
$586
per person
Feb 5 - Feb 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
16/10 Exceptional! (1,003 reviews)
Enjoyed a few days with the kids gere

Reviewed on Nov 15, 2025

Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
Price was $1,553, price is now $636 per person
$636
per person
Jan 27 - Jan 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
16.8/10 Exceptional! (1,001 reviews)
The room was not well soundproofed. Too much noise late at night and early in the morning made it difficult to rest.

Reviewed on Nov 22, 2025

Bay Breeze Premium Apartments By Eskape Collection

Bay Breeze Premium Apartments By Eskape Collection

4 out of 5
Price was $2,076, price is now $883 per person
$883
per person
Feb 12 - Feb 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
17.2/10 Exceptional! (189 reviews)
Will be nice if the hotel can think about what a new hotel guest will be going through. They will usually drive up to the hotel and look for parking. Then they will look into how to check-in and how to get to their room. It will be nice to mention in the welcome text to fill out the registration and the credit card authorization, AND also mention if we have a vehicle, what shall we do. Also will be helpful if the text will let us know the office in the building will be closed on Saturdays (and Sundays?) We were trying to figure all these out while carrying our luggages under strong winds, lucky it didn't rain. Will also be helpful to text us that we need to submit those 2 forms, then we will receive our gate and door codes. Restroom didn't smell fresh. Other than the aforementioned, the stay was good.

Reviewed on Oct 27, 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 $2,541, price is now $1,091 per person
$1,091
per person
Jan 28 - Feb 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
18.8/10 Exceptional! (56 reviews)
Quiet, modern, and luxurious are what I would describe this beautiful resort. Even in the heart of south beach, you feel like you're

Reviewed on Nov 21, 2025

AKA Hotel by Palermo Home 29 floor

AKA Hotel by Palermo Home 29 floor

3 out of 5
Brickell
Price was $2,087, price is now $909 per person
$909
per person
Feb 14 - Feb 21
found 4 hours ago
Roundtrip flight included
New York (NYC) to Miami (MIA)
18/10 Exceptional! (7 reviews)
The property was a great value with a pool and a full Kitchen was a definite plus

Reviewed on Jul 8, 2025

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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

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

Sugarloaf Beach

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

Sugarloaf Beach

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

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 $164 total per night from Nov 30 to Dec 1
$164 total
Nov 30 - Dec 1
Total with taxes and fees
7.8/10 Good! (1,708 reviews)
Good location, nice property with outdoor games and etc. Would recommend this stay.

Reviewed on Nov 19, 2025

Blue Flamingo Resort Key West
Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection

3.5 out of 5
3850 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$112 nightly
The price is $126 total per night from Dec 1 to Dec 2
$126 total
Dec 1 - Dec 2
Total with taxes and fees
7.8/10 Good! (1,129 reviews)
Parking was easy

Reviewed on Nov 21, 2025

Hilton Garden Inn Key West / The Keys Collection
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
$217 nightly
The price is $244 total per night from Dec 1 to Dec 2
$244 total
Dec 1 - Dec 2
Total with taxes and fees
8.8/10 Excellent! (1,740 reviews)
We thoroughly enjoyed our stay at Oceans Edge. It was a beautiful relaxing oasis for us to spend a few days. The weather was not great (windy & a little chilly) so we couldn't use the paddleboards or kayaks. The food at the restaurant was delicious and we ended up eating there for almost all our ...

Reviewed on Nov 18, 2025

Oceans Edge Key West Resort, Hotel & Marina
See all 3,517 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 $586 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.