Discover a selection of 500 vacation rentals in Summerland Key, FL that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and private pools. Prices start at $174 per night, and houses and cottages are popular options for a stay in Summerland Key. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Summerland Key
Destination guide

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.

Things to do

Where the cats have too many toes

Pick a key, any key. Summerland Key is a quiet, residential kinda place, so excursions might be on the menu. It's towards the western end of the Keys, meaning larger towns like Marathon and Key West are both around a half hour drive away. Macho literature aficionados will want to visit the Ernest Hemingway House in Key West, and see if they can count the toes on his resident mutant cats. While you're out that way, tour Harry S. Truman's Little White House, or take in some art at the Gallery on Greene and the Key West Historical Society.


The easiest Marathon you'll ever encounter

For such a laid-back place, a Summerland Key vacation rental gives you a lot of options. Fishermen can head over to the nearby sport-fishing capital of Marathon, or you could just stroll down to the water's edge and drop a line in. If you prefer to watch fish from a distance, then the snorkeling possibilities round here are immense. Try Looe Key marine sanctuary for something a bit special. Wildlife-watchers want to drive the 10 minutes to Big Pine Key, home to the dog-sized Key deer, or you could head a bit further out to the Dolphin Research Center.


Well they don't call it "Winterland," do they?

How does that saying go? Wherever you are in the world, the weather is probably better in the Keys. A Summerland Key vacation rental dishes up weather that you can only describe as tropical. The winter runs between November and May, though all "winter" means in the Florida Keys is that it doesn't rain as much. Otherwise it's still going to be balmy. You won't see a flake of snow, and in fact the temperature hasn't dropped below freezing since records began. As for summer, it'll be hot, and it'll pour with rain each afternoon. Bring a raincoat.

Natural features

There's a reason those Key deer never leave

The Florida Keys are an archipelago off the coast of Florida, between the Gulf of Mexico and the Atlantic Ocean. They're actually the above-water bits of a massive coral reef that started forming more than a 100,000 years ago. Because the climate's so mild, all kinds of stuff thrives here that doesn't exist further north. Hell, some of it doesn't even exist outside the Keys, like Key deer and the Key Largo woodrat. And then there are the creatures that live in the water. Marine life is bountiful, but the crocodiles and the dolphins are the real celebrities.

How to get there

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.

What are the top vacation rentals in or near Summerland Key?

Whether you want a cozy escape for you and your special someone or somewhere spacious to fit the family, you'll find some top vacation rentals in and around Summerland Key. Here are a couple to get your inspiration flowing:

  • Take advantage of conveniences like cookware, dishware and utensils and towels at "Sombrero Beach Home On Canal With Private Dock And Heated Pool". Situated around 25 miles from Summerland Key, this vacation rental has 3 bedrooms and is a hit with guests.
  • Another enticing choice is "Key West Oasis, Seperate Cottage", which is around 25 miles from Summerland Key. With 2 bedrooms, a nearby marina and a video library, it has everything you need to keep you comfortable and content.

For even more great options, use the search bar at the top of the page to find the perfect Summerland Key vacation rental for you.

What are the top-rated vacation rentals for weekend getaways in or near Summerland Key?

Get far away from the busyness of everyday life at one of our weekend getaways in or near Summerland Key. Whether you'd like to hang out with buddies or spend valued time with the family, there'll be something to suit your style. These top-rated options are hard to beat:

  • "Kayak Boot Key Harbor, 75ft Canal Home" is around 25 miles east of Summerland Key and the perfect place to relax and unwind. You'll like the range of amenities here, including games and a boat.
  • Otherwise, create memories with your favorite people at "Wow Private Pool, Ocean Front", which is around 25 miles to the east of Summerland Key. You'll have use of cable/satellite TV services, a beach and more here.

Can I find studio apartments for rent in and around Summerland Key?

Studio apartments are a simple yet stylish option, ideally suited for traveling sweethearts or solo stays. Spend your days getting acquainted with your surroundings and your nights chilling out in your cozy hideaway. These getaways in or near Summerland Key will tick all the boxes:

  • Chill by yourself or take a friend along to "Waterfront Luxury Living Inside And Out". You'll have lots of amenities at your fingertips, including an iron and ironing board and nearby birdwatching activities.
  • "Condo In Old Town Key West's Truman Annex" is another top choice, providing all you need for a heavenly Summerland Key escape. Convenient amenities here include internet services and a bicycle.

Can I find short term rentals in or near Summerland Key?

From funky studio apartments to sprawling vacation homes, Vrbo has your whirlwind escape sorted. Here are two of our favorite stays in and around Summerland Key:

  • Within easy reach of central Summerland Key, "Coconut Sunsets And Open Water Views" lays out the welcome mat for short-term guests. When you're not chilling out in your comfortable digs, get out and explore the area's best sights.
  • "Cloud 9 ~ It's Heaven On Earth In This 3b" is also well located. Bunk down here and discover why many guests rate this getaway highly.

What are the best romantic weekend getaways in or near Summerland Key?

Nothing says "I love you" quite like planning a romantic weekend together. If you'd like to spend a couple of relaxing nights away with your honey, we've got some romantic getaways in and around Summerland Key that will get your heart racing:

  • Sneak off on Friday afternoon for a couple of passion-filled nights at "Sombrero Beach Home On Canal With Private Dock And Heated Pool". Located around 25 miles from Summerland Key, this place comes with plenty of nice touches, like a balcony and air conditioning.
  • Otherwise, spend your escape drinking wine and canoodling at "Key West Oasis, Seperate Cottage", around 25 miles from Summerland Key. Beauty services and a nearby marina will help set the scene for romance.

Are there mansions for rent in or near Summerland Key?

Nothing says "best vacation evvv-er" like staying in a mansion. Treat your family to a memorable escape at one of these mansions for rent in and around Summerland Key:

  • Located around 25 miles to the west of Summerland Key, "Noona's Mansion @ The Annex Grand Home And Pool + Last Key Services" is the ideal place for a luxurious escape. Nice touches here include beauty services and a swimming pool.
  • With golf, a swimming pool and loads of other awesome amenities, "Captiva" ~ , Azul Historic Mansion Suite With Community Pool" will dazzle you and your guests. This opulent retreat is roughly 25 miles to the west of Summerland Key.

What are the best large group vacation rentals in or near Summerland Key?

Share your vacation and have even more fun. Whether you're planning an epic getaway with your besties or a big family gathering, you'll have your pick of large group vacation rentals in and around Summerland Key:

  • Providing privacy, comfort and space, you'll get everyone's tick of approval at "New Photos: Drive To Your Getaway". Up to 12 people can be accommodated at this retreat which has 5 bedrooms, a garden and a beach view. This group favorite is around 25 miles to the west of Summerland Key.
  • Invite as many as 14 of your dearest friends to "Spectacular Waterfront Estate" and fill its spaces with love and laughter. This popular option has 6 bedrooms and is around 25 miles to the east of central Summerland Key. It's crammed with features to keep a large group comfortable, such as a kitchen and a garden.

What are the best houses for rent with a pool in or near Summerland Key?

Nothing says fun like a pool does. Pull out your inflatable unicorn and check out these rental houses in or near Summerland Key that come with this vacation essential:

  • Pack your swim gear and make a booking at "Casa Capri Beautiful Tropical Style House With 3 King Suites Pool 2 Mi To Beach". There are plenty of other great amenities here, including a barbecue grill and a kitchen.
  • Alternatively, recharge your batteries at "Casa Cay West Beautiful Tropical House 3 Bedrooms 2 King Suites Pool 2 Mi Beach". In addition to its inviting pool, you'll also have use of a separate dining area and a video library.

Curious what the weather is like in Summerland Key? It has a tropical savanna climate, with average summertime temperatures ranging from 80 ºF to 85 ºF. If you're after a little more inspiration on places to stay in this popular destination, use the search bar at the top of the page and adjust the filters to browse through our entire selection of Summerland Key vacation rentals.

What are the best large family vacation rentals in or near Summerland Key?

A family get-together should be a memorable one. Whether you're organizing some time off with the kids or a long-overdue family reunion, our large family vacation rentals in or near Summerland Key offer a home away from home with enough space for everyone:

  • Around 25 miles to the west of Summerland Key, "Cloud 9 ~ It's Heaven On Earth In This 3b" has 3 bedrooms and can sleep up to 7 guests. It comes with a host of amenities, including cable/satellite TV services and a nearby coin laundry.
  • "Casa Cove Beautiful Tropical Decorated 3 King Suites Pool 2 Mi Beach" also offers the space you need to share special moments with loved ones. This rental is around 19 miles to the west of central Summerland Key and accommodates 8 guests in its 3 bedrooms. A kitchen and a balcony will help keep everyone comfortable and content.

If you're after family-friendly attractions in the area, you won't have to look far. Dolphin Research Center, The Turtle Hospital and Great White Heron National Wildlife Refuge promise lots of fun for young and old.

Can I find family cabin rentals in or near Summerland Key?

Spending time with family is important, which is why we'll help you find a place where you can truly connect. Rent one of these family cabin rentals in or near Summerland Key and make wonderful new memories with the ones you love:

  • "Cabin - Sand Is The New Snow - New 4bedroom W" - This sought-after getaway offers books and a TV and is about 25 miles east of central Summerland Key.
  • "Cabin - Orange Blossom Suite | 1 Bedroom 1 Bath In Steps Off Duval" - This stay is another favorite with families and is around 25 miles west of Summerland Key. Offering coffee and tea making facilities, a microwave oven and more, it'll get your group's nod of approval.

For more options, use the search bar at the top of the page and adjust the filters to find the Summerland Key vacation rental that's perfect for your needs.