Sugarloaf Key Vacations from $445

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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.
President Hotel Villa
Avi Lux Stay
The Retreat Collection at 1 Hotel & Homes South Beach
Henrosa Hotel
72 Park Miami Beach Boutique Residences by IliosRentals
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What to do 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
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
9.2/10 Wonderful! (41 reviews)
"Clean and quiet bungalow that is convenient to Key West but far enough away to enjoy the quiet."

Reviewed on Nov 4, 2026

Sugarloaf Key RV Resort & Cottages
Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$285 nightly
The price is $321 total per night from Nov 18 to Nov 19
$321 total
Nov 18 - Nov 19
Total with taxes and fees
8.8/10 Excellent! (1,814 reviews)
"Nice property"

Reviewed on Nov 4, 2026

Margaritaville Beach House Key West
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?
A Sugarloaf Key vacation package typically costs around $1,550 per adult for a week-long trip. Lower-priced options start around $900 per adult, while premium packages can reach up to $2,300.

*Package prices shown are the average total cost per adult across Expedia bookings over the past year and may change depending on availability, dates, and demand.
How can I save money on a Sugarloaf Key vacation package?
When you bundle, you can save up to 30%*. To save money on a Sugarloaf Key package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.
What's included in a Sugarloaf Key vacation package?
A Sugarloaf Key vacation package lets you combine flights, hotel stays, and rental cars. As a beach destination, Sugarloaf Key has many hotels that offer direct access to its beautiful beaches.

Exactly what's included will vary by hotel and package, so it's worth reviewing the details before you confirm your booking.
How do I find cheap Sugarloaf Key vacation package deals?
The cheapest Sugarloaf Key vacation package deals start around $830 per adult for weekend trips. Separately, March typically has the lowest average monthly prices, around $1,430 per adult, for a 4-day trip.

Bundling flights and hotel together can also help reduce the total compared with booking separately. Week-long Sugarloaf Key vacation package deals typically save around $200 per adult, with nearly all bookings seeing savings.

Browse cheap vacation packages in Sugarloaf Key on Expedia to compare current deals for your preferred dates.

*Package prices shown are the average total cost per adult across Expedia bookings over the past year and may change depending on availability, dates, and demand.
What is the best time to visit Sugarloaf Key?
The best time for a Sugarloaf Key vacation package is from January through March, which is its most popular period for travelers. This timeframe offers pleasant conditions for enjoying the area's outdoor activities and beaches.

Consider visiting in October for Fantasy Fest or November for the Key West Offshore World Championship, both of which add to the vibrant atmosphere of the Florida Keys.
What types of vacation packages are available in Sugarloaf Key?
Sugarloaf Key, primarily known for its beaches and outdoor activities, offers a variety of vacation package options to suit different travel styles:
  • Pet-friendly: For travelers bringing their furry companions, a Sugarloaf Key vacation package can include a stay at properties like Sugarloaf Key Hotel at KOA Resort, rated 9.4 out of 10 by travelers, which features pet-friendly accommodations, a game room, and an outdoor pool. Guests often highlight the welcoming staff here.
  • Family: Families can find suitable options such as Sugar Loaf Lodge, rated 7.8 out of 10 by travelers, which provides an outdoor pool and a restaurant, with guests often praising the great staff.
  • Budget: Nearly all hotels in Sugarloaf Key fall into the midrange pricing tier, offering good value for a comfortable stay.
  • Beach: Given the destination's focus on beaches, many packages are centered around easy access to the coastline, allowing travelers to enjoy the sun and sand.
Is Sugarloaf Key better suited for a beach vacation or a cultural trip?
Sugarloaf Key is primarily a beach destination, making it an excellent choice for a beach vacation. Its identity is deeply tied to the surrounding waters and keys, with attractions like Florida Keys Beaches and Sugarloaf Beach offering ample opportunities for sun, sand, and water activities.

While the area has some historical notes, such as the former Overseas Railroad station at Pirates Cove, these are secondary to its natural coastal appeal. A Sugarloaf Key vacation package is best for travelers seeking relaxation and outdoor adventures by the sea, with cultural elements being a minor part of the experience.
Which airport should I use for a Sugarloaf Key vacation?
For a Sugarloaf Key vacation, the most convenient gateway is Key West International Airport (EYW). This airport serves the Lower Florida Keys region, including Sugarloaf Key, and is the primary option for travelers flying into the area.

Another alternative is Florida Keys Marathon Airport (MTH), which offers additional flight options and serves the middle Keys.
What are the top things to do in Sugarloaf Key?
A Sugarloaf Key vacation is centered around its beautiful beaches and natural keys, offering plenty of outdoor activities:

Browse and book things to do in Sugarloaf Key on Expedia.
What is the best time to book a Sugarloaf Key vacation package?
Book your Sugarloaf Key vacation package around 5 weeks in advance. It gives you time to secure your preferred flights and hotel while rates are still competitive. Most travelers book between 2 and 12 weeks out.

January and from March to April, are the most popular months for Sugarloaf Key packages, so booking earlier is advisable if you're traveling during these times. If you're planning a spontaneous getaway, Expedia also offers last-minute Sugarloaf Key vacation packages.
How many days do you need for a Sugarloaf Key vacation?
Most Sugarloaf Key vacation packages last around 5 days. As a beach destination, Sugarloaf Key offers a relaxed atmosphere perfect for enjoying the Florida Keys. While most travelers opt for week-long trips, nearly a third choose shorter weekend getaways, and some stay longer to fully explore the area. This allows ample time to relax on the Florida Keys Beaches and enjoy the surrounding natural beauty.
Are Sugarloaf Key vacation package hotels conveniently located?
Sugarloaf Key vacation package hotels are generally well-situated for enjoying the area's natural beauty and outdoor activities. The destination is known for its beaches, with attractions like Florida Keys Beaches about 1 mile from central Sugarloaf Key, and Sugarloaf Beach about 2 miles away.

For your stay, Sugarloaf Key Hotel at KOA Resort, rated 9.4 out of 10 by travelers, offers amenities like a hot tub and game room, with guests often highlighting the welcoming staff. Another option, Sugar Loaf Lodge, rated 7.8 out of 10 by travelers, provides a restaurant and outdoor pool, and guests frequently praise its great location. Your Sugarloaf Key vacation package can be customized around these activities and convenient lodging options.
Can I change or cancel my Sugarloaf Key vacation package if my plans change?
Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.
Do One Key members get extra savings when booking Sugarloaf Key vacation packages?
Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.
Does Expedia offer Book Now, Pay Later Sugarloaf Key vacation packages?
Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Sugarloaf Key vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.
How do I find last-minute vacation packages to Sugarloaf Key?
To find last-minute vacation packages to Sugarloaf Key, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.
How does free cancellation work on Sugarloaf Key vacation packages?
Free cancellation on a Sugarloaf Key vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.
Is it cheaper to book a Sugarloaf Key vacation as a package or separately?
An Expedia vacation package could land you great savings when compared to arranging flights and hotels separately. Better still, you can tailor your Sugarloaf Key getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
Why should I book my Sugarloaf Key vacation package with Expedia?
Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

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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.