Discover a selection of 385 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 $130 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.
Destination guide

The Key to your perfect vacation rental

Few places in the world have a reputation like the Florida Keys, and Summerland Key is one of the most chilled-out of them all. It's a place to leave your worries behind and settle down on the porch with a beer. Somewhere you'll want to slink out of bed nice and early so you can watch the sun rise. You're within easy reach of hubs like Marathon and Key West, but chances are you probably won't want to leave your Summerland Key vacation rental. Kick back and carve yourself a slice of key lime pie.

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

How to get to and around Summerland Key

Fly into Key West, FL (EYW-Key West Intl.), the closest airport, located 20.7 mi (33.3 km) from the city center. If you're unable to find a flight that fits your schedule, you might consider flying into Marathon, FL (MTH-Florida Keys Marathon), which is 25.3 mi (40.7 km) away.

How many vacation rentals are available around Summerland Key, FL?

Our 2020 property listings offer a large selection of 385 vacation rentals around Summerland Key. From 361 house rentals to 30 cottage rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

What is the best area to stay when traveling to Summerland Key?

Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Summerland Key:

  • Breezeswept Beach Estates: 21 vacation rentals
  • Sugarloaf Shores: 21 vacation rentals
  • Cudjoe Gardens: 42 vacation rentals
  • Cutthroat Harbor Estates: 137 vacation rentals
  • Doctor's Arm: 17 vacation rentals

For other neighborhoods, please use our search bar to access the selection of vacation rentals available.

What are the popular point of interests near where I can stay when traveling to Summerland Key?

Vrbo offers a large selection of vacation rentals near lovely places in Summerland Key. From Vrbo travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Reel Deal Fishing Charters: 503 vacation rentals
  • MiLo Watersports: 462 vacation rentals
  • Bahia Honda State Park and Beach: 1,413 vacation rentals
  • Key West Harbour: 1,749 vacation rentals
  • Robbie's: 1,714 vacation rentals

But there are many other points of interest around Summerland Key listed on Vrbo where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent Houses in Summerland Key?

Yes, of course. Vrbo has 361 Houses in Summerland Key. Our other popular types of vacation rentals in Summerland Key include:

  • Cottages: 30 rentals available
  • Cabins: 30 rentals available
  • Bungalows: 30 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Caravans and more.

Can I find a vacation rental with pool in Summerland Key?

Yes, you can select your preferred vacation rental with pool among our 228 vacation rentals with pool available in Summerland Key. Please use our search bar to access the selection of vacation rentals available.