Sugarloaf Key Vacations from $485
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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.
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
$5,714
per person
Nov 17 - Nov 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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 Local House
South Beach
$927
per person
Oct 17 - Oct 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9.2/10 Wonderful! (1,000 reviews)
Great location on Ocean Drive, few mins walk to the main restaurants/bars. Rooftop pool was lovely after a day at the beach. Great to have sunbeds/towels provided for the beach which is a 5 minute walk across the road.
Room was really nice with coffee machine and great view from the balcony.
Check in was easy, 100$ security deposit for each night n weed to be paid which I don’t know about. Would 10000% stay again.
Reviewed on Aug 29, 2026
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View all tripsWhat to do in Sugarloaf Key
Luxury Sandbar and Snorkeling trip in Key West
$1,200
per traveler
Sugarloaf Key Hotel Deals
Sugarloaf Key Hotel at KOA Resort
251 Co Rd 939 Summerland Key FL
Sugarloaf Key RV Resort & Cottages
311 Johnson Rd Summerland Key FL
9.4/10 Exceptional! (29 reviews)
"It was close to Key West and the price was fair. The room was clean. Although I would put blinds on the windows, it's too bright in the morning for sleeping in. And although it showed the tiki bar area open at 4pm. It wasn't opened either night we were there which was very disappointing."
Reviewed on Aug 28, 2026
Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Fully refundableReserve now, pay when you stay
$210 nightly
$237 total
Sep 8 - Sep 9
Total with taxes and fees
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 $485 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?
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
Explore a world of travel with Expedia
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- Flights from Indianapolis (IND) to Key West (EYW)
- Flights from Nashville (BNA) to Key West (EYW)
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- Flights from Jacksonville (JAX) to Key West (EYW)
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- Flights from Key West Intl.
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- Flights from Boston (BOS) to Key West (EYW)
- Flights from Florida Keys Marathon
- Visit Sugarloaf Key
- Ernest Hemingway Home and Museum
- Key West Butterfly and Nature Conservatory
- Museum of Art & History at the Custom House
- Mallory Dock
- Key West Vacations
- Key West Tropical Forest and Botanical Garden
- Fort Zachary Taylor Historic State Park
- Key West Firehouse Museum
- Clarence S. Higgs Memorial Beach Park
- Stock Island Yacht Club & Marina
- Key West Shipwreck Museum
- Jackson Square
- San Carlos Institute - Casa Cuba
- Bahama Village Vacations
- Tennessee Williams Key West Exhibit
- Visit Downtown Key West
- Waterfront Playhouse
- Schooner Western Union
- The Kite House
- Old Town Key West Vacations
- All inclusive Vacation Packages Key West
- Sombrero Beach
- Sails To Rails Museum at Flagler Station
- Looe Key National Marine Sanctuary
- Cook Island
- Key West Historic District Vacations
- Summerland Key Vacations
- Visit Big Pine Key
- Duval Street
- Fort East Martello Museum and Gallery
- Seven Mile Bridge
- Boca Chica Nude Beach
- Upper Sugarloaf Sound
- Robbie's
- Mallory Square
- Key West National Wildlife Refuge
- Big Pine Key Flea Market
- Smathers Beach
- Key West Burlesque Theater
- Southernmost Point
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
