Sugarloaf Key Vacations from $420
Book a Hotel + Flight or Car together to unlock savings
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
$6,856
per person
Nov 19 - Nov 22
found 1 day ago
Roundtrip 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
President Hotel Villa
South Beach
$902
per person
Dec 2 - Dec 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.2/10 Very Good! (1,004 reviews)
I love the room. I would definitely stay again. The only thing I would say is the showers are definitely not hot enough for me. I don’t know if I just like it too hot but that’s the only issue I really had.
Reviewed on Sep 7, 2026
Miami Vacation Rentals - District 225
Downtown Miami
$1,056
per person
Nov 7 - Nov 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9.6/10 Exceptional! (5 reviews)
The apartment had not been cleaned thoroughly. The bed sheets were not clean and the floor was dirty.
I would appreciate it if the cleaning could be done more carefully in the future.
Reviewed on Sep 7, 2026
Don't see what you're looking for?
See all available trips from Columbus to Sugarloaf Key
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
9.2/10 Wonderful! (31 reviews)
"Make sure to meet Lena and get the right place and deal from her"
Reviewed on Sep 10, 2026
Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Fully refundableReserve now, pay when you stay
$239 nightly
$269 total
Sep 28 - Sep 29
Total with taxes and fees
8.6/10 Excellent! (3,608 reviews)
"The check in staff was not friendly. The elevator in our building wasn’t working, the pool was closed and the beach was closed because of Scargasim. Also there was a $50.00 per night parking fee and none of these points were discussed with us beforehand and no discounts were offered. Two other couples ..."
Reviewed on Sep 16, 2026
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 |
More vacations you might like
Frequently asked questions
How much does a Sugarloaf Key vacation package cost?
Offering excellent value package deals from $420 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
- Flights from Tampa (TPA) to Key West (EYW)
- Flights from Orlando (MCO) to Key West (EYW)
- Flights to Big Pine Key
- Delta Air Lines Atlanta (ATL) to Key West (EYW) flights
- Flights to Cudjoe Key
- Flights to Summerland Key
- Flights to Sugarloaf Key
- Flights to Key West Intl.
- JetBlue Airways Boston (BOS) to Key West (EYW) flights
- Flights to Little Torch Key
- Lower Florida Keys All Inclusive Vacation Packages
- Big Pine Key Vacations
- Smathers Beach
- Where to stay in Marathon
- Where to stay in Lower Sugarloaf Key
- Visit Lower Florida Keys
- Sugarloaf Key All Inclusive Vacation Packages
- Where to stay in Little Torch Key
- Visit Downtown Key West
- Where to stay in Boca Chica Key
- Lower Florida Keys All Inclusive Vacation Packages
- Conch Key Vacations
- Visit New Town
- Old Town Key West Vacations
- Lower Florida Keys All Inclusive Vacation Packages
- Key West Vacations
- Lower Florida Keys All Inclusive Vacation Packages
- Visit Ramrod Key
- Visit Boca Chica Key
- Sugarloaf Key All Inclusive Vacation Packages
- Where to stay in Key Colony Beach
- Visit Big Pine Key
- Fort East Martello Museum
- Marathon Vacations
- Visit Cudjoe Key
- Visit Summerland Key
- Cow Key Vacations
- Where to stay in Lower Florida Keys
- Lower Florida Keys All Inclusive Vacation Packages
- Summerland Key Vacations
- Visit Sugarloaf Key
- Where to stay in Sugarloaf Key
- Lower Florida Keys All Inclusive Vacation Packages
- Where to stay in Cudjoe Key
- Clarence S. Higgs Memorial
- Cudjoe Key All Inclusive Vacation Packages
- Boca Chica Nude Beach
- Lower Florida Keys All Inclusive Vacation Packages
- Visit Cow Key
- Key Colony Beach Vacations
- Where to stay in Key West
- Long Key Vacations
- Lower Florida Keys All Inclusive Vacation Packages
- Where to stay in Big Pine Key
- Visit Little Torch Key
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.