Summerland Key holiday homes

We found 736 holiday rentals — enter your dates for availability

Select from 472 homes, 55 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.

Holiday rentals with weekly discounts - Summerland Key

Showing deals for:19 Dec - 26 Dec
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Why visit Summerland Key

  • Stunning beaches: Relax on beautiful beaches like Sugarloaf Beach, perfect for swimming and soaking up the sun.
  • Outdoor adventures: Enjoy kayaking in the crystal-clear waters and explore the natural beauty of the Florida Keys.
  • Tropical gardens: Immerse yourself in vibrant tropical gardens that enhance the island's natural charm.
  • Family-friendly activities: Engage in a range of family-friendly activities, making it an ideal destination for all ages.
  • Laid-back atmosphere: Experience the friendly, relaxed vibe that epitomises the Keys' lifestyle.

Top attractions in and around Summerland Key

Summerland Key is perfect for outdoor and family getaways, offering stunning beaches and national parks to explore. Enjoy kayaking in the crystal-clear waters, visit nearby Rockland Key, and relax at Sugarloaf Beach. With a range of activities and attractions, this idyllic spot caters to those seeking adventure and natural beauty in the heart of the Florida Keys.

  • Florida Keys Beaches: A delightful beach experience awaits just 12.9km from Summerland Key, with stunning views, soft sands, and a relaxed vibe perfect for sunbathing and swimming.
  • Bahia Honda State Park: Located 19.3km away, this national park offers breathtaking scenery, outdoor adventures like hiking and kayaking, and opportunities to connect with nature.
  • Upper Sugarloaf Sound: Situated within Summerland Key, this picturesque island features serene beaches and lush outdoor areas, ideal for relaxation and exploration.

Things to do recommended for couples

For a romantic getaway in Summerland Key, consider an adventure at Pigeon Key, just 29.0km away. Enjoy thrilling water sports and immerse yourselves in the outdoor vibes, making unforgettable memories together while soaking up the sun and stunning views.

Things to do recommended for families

Families visiting Summerland Key can explore the stunning Florida Keys National Marine Sanctuary, perfect for snorkelling and spotting colourful marine life. Additionally, enjoy a relaxed day at the beach, and visit the nearby Dolphin Research Center for an unforgettable encounter with dolphins.

Things to do recommended for groups

Explore the vibrant Big Pine Key Flea Market for a taste of local culture, or hit the greens at Key West Golf Club for some outdoor fun. Don't miss the Tennessee Williams Fine Art Center for a dose of arts and entertainment, perfect for groups.

*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

If you're planning a trip with friends, family, pets, or looking for extended stays, be sure to adjust your filters according to your key priorities. Here are some helpful Vrbo booking tips to consider.

  • Traveling to Summerland Key with a group: Think about how many bedrooms you'll require, as well as features like a complete kitchen or outdoor area for group get-togethers. Luckily, you can easily refine your search for all these options and more on Vrbo.
  • Traveling to Summerland Key with young kids: Travelling with young kids can be quite a task. It's important to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Summerland Key: For many families, a getaway wouldn’t feel complete without their furry companion by their side. If this resonates with you, be sure to explore Vrbo listings that welcome pets. Many of these pet-friendly homes come equipped with feeding bowls and cozy beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Summerland Key: If you're on the lookout for holiday rentals that offer great deals for stays of a month or more, you've come to the right spot. By using the appropriate filters, you'll be able to effortlessly discover and save on long-term rentals. Don’t forget to think about including extras like a parking space, a well-equipped kitchen, or even a private pool in your search.

Where to stay in Summerland Key

Summerland Key is a tropical paradise perfect for beach-loving families and outdoor enthusiasts. Explore the stunning Florida Keys beaches, soak in the beauty of the vibrant tropical gardens, and enjoy the friendly atmosphere. Nearby, you can visit Fort Lauderdale for a taste of city life, while the surrounding regions offer excursions that will create lasting memories. Embrace the laid-back vibe and budget-friendly options that make this destination a true gem in the Keys.

  • Cudjoe Key: Cudjoe Key is a charming village located just a stone's throw from Summerland Key, offering a delightful island experience. This picturesque destination is ideal for families and outdoor enthusiasts alike. Visitors can enjoy a variety of activities, from exploring the stunning beaches to engaging in recreational areas perfect for fun-filled family outings. The local shopping areas and malls provide ample opportunities for a bit of retail therapy. Notable landmarks include the surrounding beaches and the beautiful archipelago, making it a perfect spot for those seeking both relaxation and adventure.
  • Little Torch Key: Little Torch Key is another delightful village in close proximity to Summerland Key, renowned for its serene atmosphere and beautiful beaches. A favourite among families, it’s a fantastic place to enjoy outdoor activities, whether it’s lounging on the sandy shores or engaging in fun water sports. The village boasts several shopping areas and recreational spots, ensuring a well-rounded visit. With its inviting family beaches and stunning natural landscapes, Little Torch Key offers a tranquil escape into Florida's beautiful Keys.
  • Sugarloaf Key: Sugarloaf Key is a lovely village that promises an idyllic island getaway near Summerland Key. Known for its outdoor appeal, this destination attracts families looking for adventure and relaxation. With a variety of recreational areas and shopping options, visitors can easily fill their days with activities. The nearby beaches and picturesque islands contribute to the area's charm, while the surrounding archipelago beckons exploration. Sugarloaf Key is a wonderful spot for those wanting to enjoy Florida’s natural beauty while creating lasting memories.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
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 a breeze

Are you hoping to save on your next adventure? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, consider booking a longer stay to unlock even greater savings. To discover a Vrbo property that aligns with your budget, feel free to use our filters to sort by price, location, and the type of holiday rental that suits you best.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board provides a convenient area for you to plan new trips, manage your ongoing arrangements, or review your bookings. Your saved or reserved properties are neatly categorized into Potential, Upcoming, or Current Trips. To check out Trip Boards, head over to: 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)
  • 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. 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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