Summerland Key holiday lettings

We found 745 holiday rentals — enter your dates for availability

Select from 478 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.

Holiday rentals with weekly discounts - Summerland Key

Showing deals for:3 Oct - 10 Oct
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Why visit Summerland Key

  • Stunning beaches: Enjoy the beautiful sandy shores perfect for sunbathing and swimming.
  • Outdoor activities: Engage in various adventures such as snorkelling, kayaking, and fishing in the crystal-clear waters.
  • Local charm: Experience the friendly atmosphere and welcoming locals that make Summerland Key unique.
  • Budget-friendly accommodation: Choose from a range of holiday rentals including cottages and condos that cater to all budgets.
  • Natural beauty: Explore nearby national parks and islands offering breathtaking landscapes and wildlife.

Popular types of accommodation in Summerland Key

Explore a variety of holiday rentals in Summerland Key, including houses, cosy cottages, and modern condos. Whether you're travelling with family or friends, our selection of vacation rentals caters to every need. Enjoy the sun-soaked beaches and vibrant local culture while saving money and gaining peace of mind with our transparent booking process. Discover the perfect home away from home for your next getaway in Summerland Key.

  • Houses: The top choice for visitors to Summerland Key, these homes offer spacious and comfortable retreats for families or groups.
  • Condos: A popular option for those seeking a blend of convenience and amenities, providing a home-like atmosphere with resort-style facilities.
  • Cottages: Ideal for a charming and quaint experience, these delightful abodes are perfect for a romantic getaway or a peaceful escape.
  • Apartments: A practical choice for shorter stays, offering the essentials for a comfortable visit in a more urban setting.
  • Villas: Luxurious and spacious, these properties are perfect for an indulgent holiday experience in Summerland Key.**

Top attractions in and around Summerland Key

Summerland Key is ideal for outdoor and family beach holidays, offering a range of attractions including beaches, islands, and national parks. Visitors can enjoy a variety of outdoor activities and adventure experiences, with highlights such as Paradise Summerland Key and popular local attractions. Whether you're seeking friendly activities or simply wish to bask in the natural beauty, Summerland Key provides an unforgettable holiday experience for everyone.

  • Florida Keys Beaches: Located 5.0km from Summerland Key, this beach offers a quintessential tropical experience with golden sands and vibrant beach vibes, perfect for relaxation and sunbathing.
  • Upper Sugarloaf Key: Nestled within Summerland Key, this charming neighbourhood boasts a friendly community atmosphere and city vibes, making it ideal for exploring local shops and culture.
  • Upper Sugarloaf Sound: This picturesque island features stunning outdoor settings and beach vibes, inviting visitors to enjoy kayaking, fishing, and breathtaking sunsets.

Things to do recommended for couples

For a romantic getaway in Summerland Key, explore the thrilling water sports at Pigeon Key, situated 11.2km away. Enjoy adventurous activities together while soaking up the stunning outdoor atmosphere, making unforgettable memories as a couple amidst the beautiful Florida Keys.

Things to do recommended for families

Families visiting Summerland Key can experience the thrill of snorkelling at the nearby John Pennekamp Coral Reef State Park, explore the delightful wildlife at the Dolphin Research Center, and enjoy a sunny day at the beautiful beaches perfect for building sandcastles and relaxing together.

Things to do recommended for groups

Explore the Big Pine Key Flea Market for a taste of local culture, only 3.1km from Summerland Key. Enjoy a round of golf at the Key West Golf Club, 12.4km away, or immerse yourselves in the arts at the Tennessee Williams Fine Art Center, also 12.4km distant.

Booking with Vrbo is a breeze

Looking to save on your next holiday? Consider being flexible with your travel dates, as prices can fluctuate. Moreover, opting for a longer stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, utilise our filters to search by price, location, and type of holiday rental.

Where to stay in Summerland Key

Summerland Key, a picturesque island city in the Florida Keys, offers an idyllic setting for outdoor family vacations. With its stunning sandy beaches and a welcoming atmosphere, visitors can indulge in tropical excursions and enjoy a laid-back vibe. Explore nearby attractions and discover the charm of this region, where friendly locals and budget-friendly options make for a memorable getaway. Your next vacation in the tropical keys promises relaxation and adventure in equal measure.

  • Cudjoe Key: Cudjoe Key is a charming village nestled within the Florida Keys, located just a short distance from Summerland Key. This scenic island destination is a haven for outdoor enthusiasts and families, offering a tranquil beach experience. Visitors can indulge in various activities, from exploring the local recreational areas to enjoying shopping at nearby centres. The island's picturesque beaches and stunning archipelago views are perfect for leisurely days spent soaking up the sun or engaging in water sports.
  • Sugarloaf Key: Sugarloaf Key is a delightful village that boasts the same idyllic island charm found throughout the Florida Keys. Situated conveniently near Summerland Key, it attracts visitors seeking outdoor adventures and family-friendly activities. The local shopping areas and recreational venues provide ample opportunities for exploration and enjoyment. The Key’s beautiful beaches and surrounding islands are ideal for families looking to relax or partake in exciting water activities, making it a memorable stop on your vacation.
  • Little Torch Key: Little Torch Key is a picturesque village that offers visitors an authentic island experience, located in close proximity to Summerland Key. Known for its family-friendly atmosphere, this island is perfect for outdoor activities and beach relaxation. The local recreational areas and shopping centres ensure that guests have everything they need for a fun-filled day. With its stunning beaches and inviting family beach spots, Little Torch Key provides a delightful escape into the natural beauty of the Florida Keys.

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. Peak season runs in March to April and July, while off-peak times, like May and October to November tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January71.1°F (21.7°C)No Rain (Dry)Mostly SunnyAverageAverage
February72.1°F (22.3°C)No Rain (Dry)Mostly SunnyAverageAverage
March73.2°F (22.9°C)No Rain (Dry)Mostly SunnySlightly HighSlightly High
April76.8°F (24.9°C)No Rain (Dry)Mostly SunnySlightly HighSlightly High
May79.3°F (26.3°C)Light RainMostly SunnySlightly LowAverage
June82.6°F (28.1°C)Light RainMostly SunnyAverageAverage
July84.0°F (28.9°C)Light RainMostly SunnySlightly HighAverage
August84.4°F (29.1°C)Light RainMostly SunnyAverageSlightly Low
September83.7°F (28.7°C)Light RainMostly SunnyAverageSlightly Low
October80.8°F (27.1°C)Light RainMostly SunnySlightly LowSlightly Low
November76.6°F (24.8°C)Light RainMostly SunnySlightly LowAverage
December73.8°F (23.2°C)No Rain (Dry)Mostly SunnyAverageSlightly High

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

If you’re travelling with a group, family, pets, or planning an extended stay, it’s important to apply the right filters to meet your needs. Here are some helpful Vrbo booking tips for you.

  • Traveling to Summerland Key with a group: Think about the number of bedrooms you'll require, as well as amenities like a fully-equipped kitchen or outdoor space for group gatherings. Thankfully, you can easily apply filters for all of these features, and more, on Vrbo.
  • Traveling to Summerland Key with young kids: Travelling with young children can present its own set of challenges. It's important to prioritise their comfort and safety, alongside ensuring access to suitable amenities like a private swimming pool. Additionally, it's wise to think about your closeness to attractions that are suitable for families.
  • Taking your pets with you to Summerland Key: For many, a family holiday isn’t truly complete without their four-legged companion. If this resonates with you, consider exploring 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 in search of holiday rentals that offer discounts for stays of a month or more, you’ve come to the perfect destination. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include features such as a parking space, a well-equipped kitchen, or even a private pool in your search criteria.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board offers a handy platform for organising your travel plans, allowing you to create new trips, resume from where you last stopped, or review your existing arrangements. You can easily access and sort your saved or booked properties under the categories of Potential, Upcoming, or Current Trips. To begin using Trip Boards, simply visit: https://www.vrbo.com/en-gb/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 rental accommodation in Summerland Key?
According to our research, houses are considered the most popular holiday rental type in Summerland Key. But naturally, everyone's idea of an awesome stay isn't going to be the same. Vrbo has holiday rentals 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 rental 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 Vrbo holiday rentals 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 Vrbo 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 rentals in Summerland Key?
Pack a bone and a squeezy toy for the pup in your life because Summerland Key has 29 holiday rentals 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 rentals on Vrbo. 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 Vrbo. 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 rental amenities in Summerland Key?
A firepit, a swimming pool and a barbecue grill are rated the most popular rental amenities in Summerland Key. Whether you're taking to the road on your own, with your significant other or a group of friends, Vrbo can help you find a holiday rental that matches your tastes with all the features you need.
Are there large group holiday rentals 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 rentals 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 rentals 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 rentals in Summerland Key?
Pick from six two-bedroom holiday rentals 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 rentals with WiFi in Summerland Key?
Pick from nine holiday rentals 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 Vrbo.
How can I find holiday rentals with air conditioning in Summerland Key?
You can choose from 28 Vrbo 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 rental in Summerland Key?
The age limit can differ across properties on Vrbo, so check the rules of the holiday rental in Summerland Key you want to book. But in general, it's 16, 18 or 21.
How long can I rent a holiday rental 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 Vrbo. 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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