Summerland Key holiday homes

We found 751 holiday rentals — enter your dates for availability
Select from 471 homes, 51 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.

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Why visit Summerland Key

  • Stunning Beaches: Summerland Key boasts beautiful sandy shores perfect for sunbathing and relaxation.
  • Outdoor Adventures: Engage in water sports, fishing, and nature walks to fully immerse yourself in the natural beauty.
  • Scenic Islands: Explore the picturesque islands that surround Summerland Key, offering breathtaking views and experiences.
  • Family-Friendly Environment: This destination is ideal for families, with activities suitable for all ages.
  • Laid-Back Atmosphere: Enjoy the friendly locals and the relaxed vibe that defines the Florida Keys experience.

Top attractions in and around Summerland Key

Summerland Key, Florida, offers a delightful escape for families and outdoor enthusiasts alike. Visitors can enjoy stunning beaches, explore scenic islands, and immerse themselves in the natural beauty of local state parks. This charming destination is perfect for those seeking adventure and relaxation, with opportunities for water sports, fishing, and nature walks. Additionally, there are various options for holiday rentals, providing a comfortable base to experience all that Summerland Key has to offer.

  • Florida Keys Beaches: Enjoy the authentic beach vibes at this sandy escape, located 13km away from Summerland Key, where you can soak in the sun and unwind by the surf.
  • Bahia Honda State Park: Embrace outdoor adventures at this national state park, 19km from Summerland Key, offering pristine scenery and thrilling activities.
  • Upper Sugarloaf Sound: Experience an island getaway within Summerland Key, where beach and outdoor vibes blend perfectly for a unique holiday adventure.

Things to do recommended for couples

Discover Summerland Key's charm with romantic walks along its pristine beaches and intimate waterfront dining. Enjoy a scenic boat ride at sunset, creating unforgettable memories with your partner in this tropical paradise.

Things to do recommended for families

Families will love exploring the clear waters of Florida Keys National Marine Sanctuary, where snorkelling and swimming with colourful fish is a must. Additionally, a visit to the nearby Crane Point is perfect for nature walks and discovering local wildlife, making for an unforgettable holiday.

Things to do recommended for groups

Explore the stunning waters on a group kayak tour through the mangroves, or enjoy a day of fishing chartering out to the vibrant coral reefs. Don’t miss the chance to relax together at the beautiful beaches or indulge in fresh seafood at local eateries.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Summerland Key

Whether you're journeying with a group, travelling as a family, bringing your pets along, or planning an extended stay, be sure to refine your search with the right criteria. Here are some Vrbo booking suggestions for you.

  • Traveling to Summerland Key with a group: Consider how many bedrooms you'll require, along with features like a complete kitchen or a backyard for group get-togethers. Luckily, Vrbo allows you to refine your search to include all these and more.
  • Traveling to Summerland Key with young kids: Traveling with young children presents its challenges. It’s important to prioritise their comfort and safety, while also seeking out amenities suited to their age, like a private swimming pool. Additionally, it’s wise to think about how close you are to attractions that cater to families.
  • Taking your pets with you to Summerland Key: For many, a family holiday wouldn’t be the same without their furry companion. If this resonates with you, explore Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Summerland Key: If you're seeking holiday rentals with discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in Summerland Key

Discover Summerland Key, Florida, a tropical island gem perfect for outdoor, beach, and family holidays. Enjoy the laid-back atmosphere, friendly locals, and budget-friendly excursions that capture the essence of a Florida Keys holiday. From relaxing days on the beach to exploring local landmarks, Summerland Key offers a unique island experience for every traveller seeking a slice of paradise in the Florida Keys.

  • Cudjoe Key: Cudjoe Key is a delightful island village nestled in the vicinity of Summerland Key. With its scenic natural setting, this destination is perfect for travellers seeking a blend of outdoor adventures, beach leisure, and family-friendly activities. The area offers access to a variety of recreational spaces, shopping centres, and a bustling shopping mall. The local landmarks, including pristine beaches, a charming island atmosphere, and a cluster of archipelagos, invite visitors to immerse themselves in nature and enjoy a day out with the family.
  • Sugarloaf Key: Sugarloaf Key is an inviting island village that promises a refreshing beach experience surrounded by outdoor adventures and family pursuits. Located near Summerland Key, its natural coastal charm is enhanced by accessible shopping areas, a vibrant shopping mall centre, and recreational spots. The nearby landmarks, featuring stunning beaches, a captivating island vibe, and a family-oriented beach scene, make Sugarloaf Key an appealing destination for those looking to balance relaxation with a bit of exploration.
  • Little Torch Key: Little Torch Key is a welcoming island village that offers an idyllic mix of outdoor activities, beachside relaxation, and family fun. Set in close proximity to Summerland Key, visitors can enjoy convenient access to recreational areas, shopping centres, and a bustling shopping mall. The local attractions, highlighted by sandy beaches, a family-friendly beach environment, and a picturesque island setting, provide plenty of opportunities for memorable outdoor adventures and laid-back days by the sea.

Best time to go to Summerland Key

If you're planning a trip to Summerland Key, it's a good idea to check both the weather and property rates. The warmest month is August.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January71.1°F (21.7°C)No Rain (Dry)Mostly SunnyAverage
February72.1°F (22.3°C)No Rain (Dry)Mostly SunnyAverage
March73.2°F (22.9°C)No Rain (Dry)Mostly SunnySlightly High
April76.8°F (24.9°C)No Rain (Dry)Mostly SunnySlightly High
May79.3°F (26.3°C)Light RainMostly SunnySlightly Low
June82.6°F (28.1°C)Light RainMostly SunnyAverage
July84.0°F (28.9°C)Light RainMostly SunnySlightly High
August84.4°F (29.1°C)Light RainMostly SunnyAverage
September83.7°F (28.7°C)Light RainMostly SunnyAverage
October80.8°F (27.1°C)Light RainMostly SunnySlightly Low
November76.6°F (24.8°C)Light RainMostly SunnySlightly Low
December73.8°F (23.2°C)No Rain (Dry)Mostly SunnyAverage

Booking with Vrbo is simple

Looking to trim costs on your next getaway? Being flexible with your travel dates might just do the trick, since prices can fluctuate. You could also unlock great savings by booking a longer stay. To discover a Vrbo property that fits your budget, simply use our filters to sort by price, location, and the type of holiday rental you’re after.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board offers a handy space where you can start planning new trips, pick up on previous plans, or organise your upcoming adventures. Properties that you’ve saved or booked are neatly categorised as Potential, Upcoming, or Current Trips. To begin using Trip Boards, please visit: https://www.bookabach.co.nz/trips.

**Based on Vrbo properties bookings.

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)
  • Southernmost Point (23.5 mi / 37.9 km)
  • Upper Sugarloaf Key (5.2 mi / 8.3 km)
  • Sugarloaf Beach (8.1 mi / 13 km)
  • Looe Key National Marine Sanctuary (8.2 mi / 13.2 km)
  • Calusa Beach (10.4 mi / 16.7 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. Bookabach 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 Bookabach 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 Bookabach 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 Bookabach. 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 Bookabach. 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, Bookabach 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 Bookabach.
How can I find holiday homes with air conditioning in Summerland Key?
You can choose from 28 Bookabach 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 Bookabach, 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 Bookabach. 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.

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