Summerland Key holiday rentals

We found 734 holiday rentals — enter your dates for availability

Select from 467 homes, 53 cottages and other holiday rentals in Summerland Key to find one that's perfect for your trip. Whether you're travelling with family, friends or just your furry companion, holiday rentals have the amenities that you expect for your stay, which might include Wi-Fi and a hot tub. Whatever you're looking for, you'll be able to choose a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

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, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

Book a holiday rental for your Summerland Key getaway

Learn about the unique charm of Summerland Key with a stay in a holiday home rental. This city has something for everyone. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday 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

Do you want to discover top things to see and do in the area? Venture out of your holiday home and experience everything that Summerland Key has to offer. These are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Key West Golf Club (19.6 mi / 31.6 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 adventurous traveller or just want to appreciate the scenery, Summerland Key is a great place to get outside. These are some of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

  • Florida Keys Beaches (7.7 mi / 12.4 km)
  • Sugarloaf Beach (8.1 mi / 13 km)
  • Calusa Beach (10.4 mi / 16.7 km)
  • Boca Chica Beach (16.1 mi / 25.9 km)
  • Boca Chica Nude Beach (16.4 mi / 26.4 km)
  • Pigeon Key (18.4 mi / 29.7 km)

Transport options to and around Summerland Key

The nearest airport is in Key West, FL (EYW-Key West Intl.), located 20.9 mi (33.6 km) from the city centre. 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 25.1 mi (40.3 km) away.

Frequently asked questions

What is the most popular type of holiday home accommodation in Summerland Key?
According to our research, houses are considered the most popular holiday home type in Summerland Key. But naturally, everyone’s idea of an awesome stay isn’t going to be the same. Stayz has holiday homes in a variety of shapes and sizes, so you’re bound to find your perfect match.
How much does it cost to rent a holiday home in Summerland Key?
Length of stay, season and property type are some things that can influence the price of a holiday home. Simply click on your dates of travel to find the ultimate escape. From comfy cabins to expansive luxury villas, all Stayz holiday homes provide unbeatable value.
How much does it cost to rent a beach house in Summerland Key?
The average price for a holiday 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 Stayz 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 holiday homes in Summerland Key?
Pack a bone and a squeezy toy for the pup in your life because Summerland Key has 29 holiday homes 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 holiday homes on Stayz. 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 Stayz. Morning dip, sunset soak or midnight swim? Downtime is up to you when your holiday home comes with its own swimming pool.
What are popular home amenities in Summerland Key?
A firepit, a swimming pool and a barbecue grill are rated the most popular home amenities in Summerland Key. Whether you’re taking to the road on your own, with your significant other or a group of friends, Stayz can help you find a holiday home that matches your tastes with all the features you need.
Are there large group holiday homes in Summerland Key?
There are nine holiday 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 holiday homes 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 favourite 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 Centre

Are there one-bedroom holiday homes in Summerland Key?
Yes, there are two one-bedroom properties in Summerland Key to select from. A one-bedroom holiday property is a wonderful choice if it’s just you and your sweetheart or if you’re travelling 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 holiday homes in Summerland Key?
Pick from six two-bedroom holiday homes 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 holiday homes with WiFi in Summerland Key?
Pick from nine holiday homes 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 Stayz.
How can I find holiday homes with air conditioning in Summerland Key?
You can choose from 28 Stayz holiday homes with air conditioning in Summerland Key offering that cooling breeze and extra touch of comfort. Enter your travel dates and then use our filter tool to find properties with air conditioning.
How old do you have to be to rent a holiday home in Summerland Key?
The age limit can differ across properties on Stayz, so check the rules of the holiday home in Summerland Key you want to book. But in general, it’s 16, 18 or 21.
How long can I rent a holiday home in Summerland Key for?
It really depends on the Summerland Key property. To browse a list of options offering extended stays, simply enter your travel dates and guest number into Stayz. Look forward to having the entire place to yourself, along with comforts such as a full kitchen, air conditioning and outdoor spaces where the kids can burn off energy. Keep your eyes open for long-term stays that offer discounted weekly or monthly prices.

People also search for

Beach holiday rentals in Siesta Key
Standard Link for Siesta Key
Beach holiday rentals in Destin
Standard Link for Destin

More Holiday Rentals ideas

Marathon Holiday Rentals
Standard Link for Marathon
Daytona Beach Holiday Rentals
Standard Link for Daytona Beach
Delray Beach Holiday Rentals
Standard Link for Delray Beach
Melbourne Beach Holiday Rentals
Standard Link for Melbourne Beach
Boca Raton Holiday Rentals
Standard Link for Boca Raton
West Palm Beach Holiday Rentals
Standard Link for West Palm Beach
Davenport Holiday Rentals
Standard Link for Davenport
Melbourne Holiday Rentals
Standard Link for Melbourne
Silver Springs Holiday Rentals
Standard Link for Silver Springs
Clermont Holiday Rentals
Standard Link for Clermont
The Villages Holiday Rentals
Standard Link for The Villages
Marco Island Holiday Rentals
Standard Link for Marco Island
Key Largo Holiday Rentals
Standard Link for Key Largo
Santa Rosa Beach Holiday Rentals
Standard Link for Santa Rosa Beach
Destin Holiday Rentals
Standard Link for Destin
Cocoa Beach Holiday Rentals
Standard Link for Cocoa Beach
Palm Beach Holiday Rentals
Standard Link for Palm Beach
Islamorada Holiday Rentals
Standard Link for Islamorada
Siesta Key Holiday Rentals
Standard Link for Siesta Key
Lakeland Holiday Rentals
Standard Link for Lakeland
Panama City Beach Holiday Rentals
Standard Link for Panama City Beach
Anna Maria Holiday Rentals
Standard Link for Anna Maria
Osprey Holiday Rentals
Standard Link for Osprey
Key West Holiday Rentals
Standard Link for Key West
Naples Holiday Rentals
Standard Link for Naples
Palm Beach Gardens Holiday Rentals
Standard Link for Palm Beach Gardens
St. Augustine Holiday Rentals
Standard Link for St. Augustine
Miramar Beach Holiday Rentals
Standard Link for Miramar Beach