Sugarloaf Key Vacations from $245

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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.
Barcelona Studios Guesthouse

Barcelona Studios Guesthouse

2 out of 5
South Beach
Price was $507, price is now $245 per person
$245
per person
Sep 26 - Sep 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
9.4/10 Exceptional! (228 reviews)
Your staying here for the location. Very old Florida. The a/c was very loud and hard to sleep through and the bed was flimsey and uncomfortable. All the toiletries are in the lobby which if you dont know that can be annoying. There are two cats that roam around very cute. And an adorable area in the back perfect for reading or having a glass of wine.

Reviewed on Jul 13, 2026

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 $8,834, price is now $4,060 per person
$4,060
per person
Sep 22 - Sep 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
8/10 Very Good! (1 review)
Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....

Reviewed on Jun 22, 2016

The Marlin Hotel

The Marlin Hotel

4 out of 5
South Beach
Price was $1,006, price is now $478 per person
$478
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
9.2/10 Wonderful! (1,002 reviews)
Perfect location for South Beach. One block off Ocean Drive with bars, restaurants, clubs, etc. all within walking distance & a great Italian restaurant on-property too.

Reviewed on Jul 13, 2026

The Local House

The Local House

3.5 out of 5
South Beach
Save 100% on your flight
Price was $757, price is now $381 per person
$381
per person
Sep 26 - Sep 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
9.2/10 Wonderful! (1,002 reviews)
We only stayed for one night before driving down to the keys for my birthday but we really enjoyed our stay at The Local House. All of the staff were incredibly kind and they even blew up balloons and decorated our room for my birthday. Considering how busy the area was, the rooms were incredibly quiet and the bed was super comfortable. The only complaint we would have is that the bathrooms are slightly outdated in comparison to the bedrooms but other than that, we really enjoyed our stay and would recommend The Local House to anyone looking to stay in South Beach.

Reviewed on Jul 5, 2026

Bay Breeze Premium Apartments By Eskape Collection

Bay Breeze Premium Apartments By Eskape Collection

4 out of 5
Save 100% on your flight
Price was $956, price is now $482 per person
$482
per person
Aug 15 - Aug 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
8.8/10 Excellent! (227 reviews)
Debería haber una atención al huesped más directa y dar facilidades a entregas como Amazon, FedEx, UPS, et.

Reviewed on Jul 10, 2026

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What to do in Sugarloaf Key

Private Luxury Sandbar Excursion

Private Luxury Sandbar Excursion

$1,200
per traveler
Private Luxury Sandbar Excursion
Marathon Backcountry Permit

Marathon Backcountry Fishing Charter

$667
per traveler
Marathon Backcountry Fishing Charter
Luxury Sandbar and Snorkeling trip in Key West

Luxury Sandbar and Snorkeling trip in Key West

$1,200
per traveler
Luxury Sandbar and Snorkeling trip in Key West
See all activities in Sugarloaf Key

Sugarloaf Key Hotel Deals

Sugarloaf Key Hotel at KOA Resort

Sugarloaf Key Hotel at KOA Resort

3 out of 5
251 Co Rd 939 Summerland Key FL
9.8/10 Exceptional! (597 reviews)
"everything was awesome except the water amenities rental, until 3:00pm is too early."

Reviewed on Jul 14, 2026

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Sugarloaf Key Hotel at KOA Resort
Sugarloaf Key RV Resort & Cottages

Sugarloaf Key RV Resort & Cottages

3 out of 5
311 Johnson Rd Summerland Key FL
9.4/10 Exceptional! (19 reviews)
"The cabins were pretty much new. Beautiful views. Also the cabins are separate from RV area. Cant wait to go back. Lass that 1/2 hour to Key West. Way better price base foe better rooms and amenities."

Reviewed on Jul 14, 2026

Get rates
Sugarloaf Key RV Resort & Cottages
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
$216 nightly
The price is $243 total per night from Aug 3 to Aug 4
$243 total
Aug 3 - Aug 4
Total with taxes and fees
8.6/10 Excellent! (2,344 reviews)
"Great location, great service and very clean."

Reviewed on Jul 14, 2026

Beachside Resort & Residences
See all 3,435 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 $245 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.