Summerland Key holiday homes

We found 761 holiday rentals — enter your dates for availability
Select from 479 homes, 48 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)

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)
  • Upper Sugarloaf Key (5.2 mi / 8.3 km)
  • Calusa Beach (10.4 mi / 16.7 km)
  • Boca Chica Beach (16.1 mi / 25.9 km)
  • Pigeon Key (18.4 mi / 29.7 km)
  • Key West Tropical Forest and Botanical Garden (20 mi / 32.3 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 best area to stay in Summerland Key when booking a holiday rental?
When considering the best area to stay in Summerland Key, Florida, for a holiday rental, the picturesque neighbourhoods along the waterfront are particularly appealing. The serene atmosphere and stunning views make it an ideal choice for those looking to unwind.One of the highlights of this area is the proximity to the beautiful beaches, where you can indulge in sunbathing or various water sports. Additionally, the nearby nature parks offer excellent opportunities for kayaking and birdwatching, allowing you to immerse yourself in the local flora and fauna.Summerland Key boasts a variety of holiday rental properties that cater to different tastes and budgets, ensuring visitors can find a suitable option that meets their needs. The charm of the area, combined with its attractions, makes it a wonderful place to create lasting holiday memories.
Where are the best areas for renting a beach house in Summerland Key?
For renting a beach house in Summerland Key, the area along the waterfront offers a picturesque setting ideal for a relaxing getaway. Properties in this region typically feature direct ocean access, allowing guests to enjoy activities like swimming, kayaking, and fishing right from their doorstep. Many beach houses come equipped with amenities such as private pools, spacious outdoor decks, and barbecue grills, superb for those who enjoy alfresco dining in a tropical environment.The neighbourhoods close to the Summerland Key Marina are particularly appealing, as they provide convenient access to local boat rentals and charter services for exploring the surrounding waters. Here, you can find charming homes that often include features like updated kitchens, outdoor showers, and ample parking for boats. The proximity to shops and restaurants in the nearby area adds to the convenience for travellers.Additionally, the scenic views of the Florida Keys' sunsets are a highlight, with several properties boasting large windows or balconies for enjoying the stunning vistas.
What is the most popular type of holiday rental accomodation in Summerland Key?
In Summerland Key, holiday houses are the most prevalent type of holiday rental, with around 1,796 available throughout the area. These properties typically feature spacious layouts, multiple bedrooms, fully equipped kitchens, and outdoor spaces such as decks or patios, superb for enjoying the warm Florida weather. Many of these houses are situated near the picturesque coastline, allowing easy access to activities like fishing and boating.Additionally, there are approximately 192 cottages, which provide a charming and more intimate accommodation option, often equipped with kitchens and cosy living spaces. For those looking for a great experience, about 120 campsites and 80 mobile homes are also available, suiting travellers seeking a more adventurous stay. Villas, while less common with only 28 options, offer a touch of luxury and are generally equipped with upscale amenities.
Are there any family house rentals in Summerland Key?
In Summerland Key, Florida, families will find a wealth of holiday rentals, with around 347 options available. This picturesque area is known for its beautiful waterfront properties and close-knit community atmosphere, making it an ideal getaway for those with children. Many of these homes offer spacious living areas, fully equipped kitchens superb for family meals, and outdoor spaces where kids can play and adults can relax.Some properties feature private pools, BBQ grills, and easy access to the stunning beaches and local parks, ensuring that families can enjoy both relaxation and outdoor activities. The nearby Looe Key National Marine Sanctuary provides opportunities for snorkelling and diving, while the vibrant setting of Key West is just a short drive away, offering additional attractions and dining options.
Can I rent a holiday home with a pool or hot tub in Summerland Key?
In Summerland Key, there are plenty of holiday homes available for rent that come with pools and hot tubs, with around 383 options to choose from. This idyllic location in the Florida Keys offers a range of waterfront properties, many of which are situated directly on the canals or have stunning ocean views. Travellers can expect amenities such as private swimming pools, relaxing hot tubs, spacious outdoor patios for dining al fresco, and fully equipped kitchens, great for preparing meals after a day of exploring.Many homes also feature additional comforts like barbecues, sun loungers, and easy access to water activities such as boating and fishing.
Are there pet-friendly house rentals in Summerland Key?
In Summerland Key, there are numerous pet-friendly house rentals available, offering travellers a variety of options for their stay. Many of these properties come equipped with amenities such as private pools, spacious outdoor areas, and fully equipped kitchens, making them ideal for families and those travelling with pets.The area is known for its beautiful waterfront views and easy access to the ocean, which is great for pet owners who enjoy spending time outdoors. Nearby, you can find parks and green spaces that welcome pets, allowing for enjoyable walks and playtime.
Are there any remote work holiday rentals in Summerland Key?
In Summerland Key, Florida, there are plenty of remote work holiday rentals available, with approximately 1,892 options to choose from. This idyllic location offers a serene environment superb for those looking to blend work and leisure. Many of the properties come equipped with essential amenities for remote work, including high-speed Wi-Fi, dedicated workspace, and comfortable desk areas, ensuring productivity during your stay.The area is known for its stunning waterfront views and proximity to various outdoor activities. Rentals may feature spacious living areas, fully equipped kitchens, and often outdoor spaces like patios or balconies, allowing guests to unwind after a day of work. To help narrow your search, insert your dates and apply the "WiFi" filter on Bookabach.
What are popular rental amenities in Summerland Key?
In Summerland Key, popular rental amenities include fully equipped kitchens, allowing guests to prepare their own meals. Many properties also feature outdoor decks or patios, ideal for enjoying the pleasant Florida weather. Onsite parking is commonly available, providing convenience for those travelling by car. Additionally, rentals often come with coffee and tea makers for a quick morning brew, and many units boast balconies, great for relaxing while taking in the stunning views of the surrounding area.
When is the best time to visit Summerland Key for a holiday rental?
July marks the peak season for visiting Summerland Key, a stunning destination known for its sun-soaked beaches and vibrant marine life. This month attracts holidaymakers eager to enjoy the warm, tropical climate, with temperatures typically ranging from 24 to 33 degrees Celsius, ideal for outdoor adventures and relaxation by the water.During the summer, particularly from July to September, visitors can partake in a variety of activities, including snorkelling, diving, and fishing in the crystal-clear waters. The lively option, combined with the opportunity to explore the enchanting natural beauty of the Florida Keys, makes this time particularly appealing for those seeking an unforgettable holiday experience.If you're looking for a more budget-friendly option, consider planning your visit in October. This month offers a unique charm with fewer crowds, allowing you to enjoy the serene beaches and local attractions at a more leisurely pace. The weather remains pleasant, making it a great time for scenic walks and enjoying the natural scenery without the hustle and bustle of peak season.Ultimately, the best time to book your holiday rental in Summerland Key depends on your preferences—whether you lean towards the vibrant summer atmosphere filled with activities or the tranquil beauty of autumn.
What are the top attractions in Summerland Key?
In Summerland Key, visitors can enjoy a variety of attractions that highlight the natural beauty and laid-back charm of the Florida Keys. The area is known for its stunning waterfront views and access to the ocean, making it a superb spot for water activities such as kayaking and paddleboarding. The nearby Looe Key National Marine Sanctuary is a popular destination for snorkelling and diving, where travellers can explore vibrant coral reefs and diverse marine life.For those seeking relaxation, the picturesque beaches along the key offer tranquil settings for sunbathing and picnicking. The local parks, such as the Summerland Key Park, provide opportunities for walking and enjoying the natural surroundings. Additionally, the vibrant local community hosts various events and festivals throughout the year, allowing visitors to experience the unique culture and hospitality of the area.
Are all fees included in the Summerland Key holiday homes prices shown on Bookabach?
Bookabach provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Summerland Key holiday homes with parking?
Bookabach offers a wide selection of holiday homes in Summerland Key with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Summerland Key holiday homes?
You can find great discounts on holiday homes in Summerland Key on Bookabach, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Summerland Key holiday home booking on Bookabach?
To find Summerland Key holiday rentals with free cancellation, just use Bookabach's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Summerland Key?
A long-stay holiday home in Summerland Key is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Bookabach?
Bookabach's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Summerland Key holiday home?
Book your Summerland Key holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Summerland Key?
Prices for holiday homes in Summerland Key vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Summerland Key to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Bookabach as a host?
Joining Bookabach as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Bookabach makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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