Sugarloaf Key vacation rentals

We found 667 vacation rentals — enter your dates for availability

your current months are March, 2024 and April, 2024.
March 2024
April 2024
Discover a selection of 51 homes and other vacation rentals in Sugarloaf Key that are perfect for your trip. Whether you're staying in a vacation rental with your kids or with friends, you'll find the best amenities for hanging out with the people that matter most, which might include WiFi and a pool. You'll be sure to find a rental that has what everyone needs, including options that are accessible or non-smoking.

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence guarantee gives you 24/7 support
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, yards and more
  • More for less
    More space, more privacy, more amenities — more value
  • A place for everyone
    We stand for diversity, inclusion and families everywhere.
    Learn more

Trendy Sugarloaf Key will entice you

Experience the unique character of Sugarloaf Key with a stay in a vacation home rental. Travelers to this trendy city praise the bars, fishing and boating. If you need more space to accommodate a family vacation or friends trip, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in Sugarloaf Key

Are you hoping to find attractions to see in the city? Venture out of your cozy vacation rental and experience everything that Sugarloaf Key has to offer. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Key West Golf Club (13 mi / 20.9 km)
  • Key West Visitors Center (13 mi / 20.9 km)
  • The Kite House (16.7 mi / 26.9 km)
  • Blue Hole (11.7 mi / 18.9 km)
  • MLK Community Pool & Community Center (17 mi / 27.3 km)

Exploring the natural landscape of Sugarloaf Key

Whether you're an active traveler or just want to take in the scenery, you'll be sure to find the perfect setting for your vacation in Sugarloaf Key. Here are a few of the area's noteworthy features, all within 30 miles (48.2 km) of the city center:

  • Florida Keys Beaches (1.2 mi / 1.9 km)
  • Sugarloaf Beach (1.5 mi / 2.4 km)
  • Upper Sugarloaf Key (2.5 mi / 4.1 km)
  • Boca Chica Beach (9.4 mi / 15.2 km)
  • Boca Chica Nude Beach (9.7 mi / 15.7 km)
  • Key West Tropical Forest and Botanical Garden (13.4 mi / 21.6 km)

How to get to and around Sugarloaf Key

The nearest airport is in Key West Intl. Airport (EYW), located 14.2 mi (22.8 km) from the city center. If you can't find a flight that's convenient for your trip, you can also fly into Marathon, FL (MTH-Florida Keys Marathon), which is 31.6 mi (50.9 km) away.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Sugarloaf Key?

The most in-demand types of vacation rentals in Sugarloaf Key are houses. After something a little different? Vrbo has plenty of options to match the unique needs of our guests, so you'll see properties in loads of shapes and sizes. The perfect fit is waiting for you — find yours today.

How much does it cost to rent a vacation rental in Sugarloaf Key?

Property type, season and length of stay are among the factors that can affect the price of a vacation home. Simply add your dates of travel to find your perfect escape. From cozy cabins to sprawling luxury villas, all Vrbo vacation rentals offer unbeatable value.

How much does it cost to rent a beach house in Sugarloaf Key?

The average price for a vacation home by the beach in Sugarloaf Key depends on when you're visiting the area and the style and size of property you're looking for. You can easily find prices on Vrbo by entering your dates of travel. Then use our filter tool to select the number of bedrooms and amenities that you prefer, such as WiFi, air conditioning and a pool.

Are there pet-friendly vacation rentals in Sugarloaf Key?

You're in luck! There are. You can choose from 31 vacation rentals that cater to pets in Sugarloaf Key. Some of our pet-friendly vacation rentals even come with space outdoors for your four-legged friend to play around in, dog beds, complimentary treats and proximity to parks. Apply the "Pets allowed" filter to find your pawfect digs on Vrbo.

Can I rent a house with a pool in Sugarloaf Key?

Grab your swimwear and inflatable unicorn, because there are 14 houses with a private pool in Sugarloaf Key. Book one of these terrific vacation rentals and let every day be a pool day. Simply enter your travel dates into Vrbo, then use the "pool" filter to find the ideal place for a splashing good time!

What are popular rental amenities in Sugarloaf Key?

The most popular rental amenities people search for in Sugarloaf Key include a water view, a fireplace and a swimming pool. Whether you're taking a trip with pals, family or even pets, Vrbo vacation homes have the best amenities for making epic memories with the people you cherish the most.

Are there large group vacation rentals in Sugarloaf Key?

With five vacation rentals that can sleep 10 people or more in Sugarloaf Key, there's no need to hold back on your invites. From vacations with the extended family to special events like Christmas or New Year's Eve parties, Vrbo will help you find a large group rental that fits the occasion.

Are there vacation rentals in Sugarloaf Key that welcome kids?

With 31 family-friendly vacation homes available in Sugarloaf Key, now is an awesome time to introduce your children to the wonders of travel. Simply check our "Properties good for families" filter to search for stays packed with amenities ideal for families on the move, like extra bedrooms, yards, bunk beds and hot tubs.

What are the top attractions for families in Sugarloaf Key?

Keeping the kids happy during your vacation in Sugarloaf Key is a breeze with these top family-friendly attractions:

  • Florida Keys Beaches
  • Sugarloaf Beach
  • Shark Key

Can I find two-bedroom vacation rentals in Sugarloaf Key?

Select from four two-bedroom vacation properties in Sugarloaf Key. Put your little ones in the second room or fill it with a couple of your best friends. There's plenty of space for whoever's lucky enough to be coming along.

Are there vacation rentals with WiFi in Sugarloaf Key?

You can pick from 13 vacation rentals with WiFi in Sugarloaf Key. If you'd like to disconnect from daily life during your escape, but still want to be connected to the internet, these properties have just what you need. Narrow your search by applying the WiFi filter on Vrbo.

How can I find vacation rentals with air conditioning in Sugarloaf Key?

You'll find 31 Vrbo vacation homes with air conditioning in Sugarloaf Key providing that gentle, cool breeze and extra comfort level. Enter your preferred dates of travel and then take advantage of our filter tool to search for stays with air conditioning.

More Vacation Rentals ideas