Summerland Key vacation rentals

We found 676 vacation rentals — enter your dates for availability

your current months are March, 2024 and April, 2024.
March 2024
April 2024
Select from 451 homes, 55 cottages, and other vacation rentals in Summerland Key to find one that's perfect for your trip. Whether you're traveling with family, friends, or just your furry companion, vacation rentals have the amenities you need and want for your stay, which might include parking and a fireplace. No matter what you're looking for, you'll be sure to find a rental for everyone's needs, including a place that is accessible or non-smoking.

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, yards and more
  • More for less
    More space, more privacy, more amenities — more value

Book a vacation rental for your Summerland Key getaway

Learn about the unique charm of Summerland Key with a stay in a private vacation home. You'll find plenty to explore during your stay in the area. Whether you're planning a family vacation, friends trip or romantic retreat, HomeAway has a great selection of vacation homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Activities and attractions in and around Summerland Key

Are you hoping to find attractions to visit in the city? Venture out of your cozy vacation rental and experience everything that makes Summerland Key a fun place to get away. These 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 (19.6 mi / 31.6 km)
  • Key West Visitors Center (6.4 mi / 10.4 km)
  • Blue Hole (5.1 mi / 8.2 km)
  • The Kite House (23.3 mi / 37.6 km)
  • MLK Community Pool & Community Center (23.6 mi / 38.1 km)

Exploring the natural landscape of Summerland Key

Whether you're an active traveler or just want to take in the scenery, Summerland Key is a great place to get outside. These are some of the area's most stunning features, all within 30 miles (48.2 km) of the city center:

  • Florida Keys Beaches (7.7 mi / 12.4 km)
  • Calusa Beach (10.4 mi / 16.7 km)
  • Bahia Honda State Park (11.5 mi / 18.4 km)
  • Boca Chica Nude Beach (16.4 mi / 26.4 km)
  • Smathers Beach (22.1 mi / 35.6 km)
  • Clarence S. Higgs Memorial Beach Park (22.8 mi / 36.7 km)

Transportation options to and around Summerland Key

The nearest airport is in Key West Intl. Airport (EYW), located 20.9 mi (33.6 km) from the city center. If you can't find a flight that's convenient for your trip, you could also fly into Marathon, FL (MTH-Florida Keys Marathon), which is 25.1 mi (40.3 km) away.

Frequently asked questions

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

According to our research, houses are considered the most popular vacation rental type in Summerland Key. But naturally, everyone's idea of an awesome stay isn't going to be the same. Vrbo has vacation rentals in a variety of shapes and sizes, so you're bound to find your perfect match.

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

Length of stay, season and property type are some things that can influence the price of a vacation home. Simply click on your dates of travel to find the ultimate escape. From comfy cabins to expansive luxury villas, all Vrbo vacation rentals provide unbeatable value.

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

The average price for a vacation home close to the beach in Summerland Key will depend on when you're going and the size and type of property you're looking for. Find prices quickly and easily on Vrbo by entering your destination and travel dates. Then use the filters to pick the number of bedrooms and amenities important to you, like air conditioning, WiFi and a hot tub.

Are there pet-friendly vacation rentals in Summerland Key?

Pack a bone and a squeezy toy for the pup in your life because Summerland Key has 29 vacation rentals that roll out the welcome mat to pets. Let your four-legged friend get in on the family fun at one of our pet-friendly vacation rentals on Vrbo. Simply enter your dates then check the "Pets allowed" filter box.

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

Tick the "pool" box in our filter tool and pick from 23 houses with private pools in Summerland Key on Vrbo. Morning dip, sunset soak or midnight swim? Downtime is up to you when your vacation home comes with its own swimming pool.

What are popular rental amenities in Summerland Key?

A firepit, a swimming pool and a barbecue grill are rated the most popular rental amenities in Summerland Key. Whether you're taking to the road on your own, with your significant other or a group of friends, Vrbo can help you find a vacation rental that matches your tastes with all the features you need.

Are there large group vacation rentals in Summerland Key?

There are nine vacation homes in Summerland Key that can accommodate a group of 10 or more guests. Whether you're planning time away with the family or an event like an anniversary, there's enough space to get your group together under one roof.

Are there vacation rentals in Summerland Key that welcome kids?

Gather your entire family for an epic adventure in Summerland Key at one of our 29 family-friendly properties. A lot of these stays come with amenities that are great for getaways with children, such as laundry facilities, multiple bedrooms and entertainment units. Just check the "Properties good for families" filter and choose your favorite option.

What are the top attractions for families in Summerland Key?

Keeping the kids amused during your stay in Summerland Key is a snap with these fabulous family-friendly attractions:

  • Florida Keys Beaches
  • Sugarloaf Beach
  • National Key Deer Refuge Visitor Center

Are there one-bedroom vacation rentals in Summerland Key?

Yes, there are two one-bedroom properties in Summerland Key to select from. A one-bedroom vacation property is a wonderful choice if it's just you and your sweetheart or if you're traveling alone. Toss in more privacy, convenience and space compared to a regular hotel, and you've got yourself an unforgettable trip.

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

Pick from six two-bedroom vacation rentals in Summerland Key. Settle the kids into the second room or fill it with a couple of your nearest and dearest friends. There's a comfy spot for whoever's lucky enough to be joining in on the fun.

Are there vacation rentals with WiFi in Summerland Key?

Pick from nine vacation rentals with WiFi in Summerland Key. If you'd like to disconnect from daily life during your break, but still need to be connected to the web, these properties have just what you need. Narrow your search by applying the WiFi filter on Vrbo.

More Vacation Rentals ideas

People also search for