Summerland Key holiday lettings

We found 771 holiday rentals — enter your dates for availability
Select from 488 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.

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Why visit Summerland Key

  • Stunning Beaches: Enjoy pristine beaches perfect for relaxation and sunbathing, offering breathtaking views of the Gulf.
  • Water Sports: Engage in exciting activities like kayaking and snorkelling in vibrant coral reefs teeming with marine life.
  • Outdoor Exploration: Discover serene nature trails and parks ideal for hiking and wildlife observation in the surrounding natural beauty.
  • Charming Accommodations: Experience delightful private vacation rentals, cottages, and condos that enhance your stay.
  • Mesmerising Sunsets: Witness spectacular sunsets that create a picturesque atmosphere over the Gulf waters.

Popular types of accommodation in Summerland Key

Welcome to Summerland Key, a picturesque gem in the Florida Keys, where sun-kissed shores and vibrant marine life await. Immerse yourself in the natural beauty with stunning waterfront views, perfect for boating and fishing. Explore local attractions like the serene nature trails and charming parks, or simply unwind in one of the delightful houses, condos, or cottages. Experience the warmth and charm of Summerland Key with a vacation rental that suits your needs.

  • Houses: The top choice for visitors to Summerland Key, offering spacious living and the comforts of home.
  • Condos: A popular second option, these provide modern amenities and often stunning views of the surroundings.
  • Cottages: Quaint and charming, cottages are perfect for a snug getaway amidst nature.
  • Apartments: A practical choice for those seeking convenience and ease of access to local attractions.
  • Villas: Luxurious and spacious, villas offer a lavish retreat for larger groups or families.**

Top attractions in and around Summerland Key

Summerland Key, Florida, is a delightful destination for outdoor enthusiasts and families seeking a beachside getaway. Visitors can explore its stunning beaches and idyllic islands, perfect for relaxation and scenic experiences. The area also boasts access to nearby national parks, offering opportunities for hiking and wildlife observation. For a truly memorable stay, consider indulging in a vacation rental that allows you to immerse yourself in the natural beauty of this charming locale.

  • Sugarloaf Beach: A tranquil stretch of sand within Summerland Key, Sugarloaf Beach offers a laid-back atmosphere perfect for sunbathing, swimming, and picnicking. The crystal-clear waters are ideal for snorkelling and spotting marine life.
  • Cook Island: A picturesque island just 8km away, Cook Island is a hidden gem featuring beautiful beaches and lush landscapes. It's perfect for outdoor exploration, relaxation, and enjoying the natural beauty of the Florida Keys.
  • Bahia Honda State Park: Located nearby, this stunning park boasts pristine beaches, scenic trails, and opportunities for kayaking and birdwatching. Its breathtaking views and diverse ecosystems make it a must-visit for nature enthusiasts.

Things to do recommended for couples

Seeking romance in Summerland Key? Enjoy a sunset kayak tour through the mangroves, indulge in a candlelit dinner at a waterfront restaurant, or relax on a secluded beach. Don't forget to explore the stunning coral reefs while snorkelling together for an unforgettable experience.

Things to do recommended for families

Families visiting Summerland Key can enjoy a day of adventure at the nearby Dolphin Research Centre, where kids can interact with dolphins, and explore the beautiful beaches perfect for building sandcastles and swimming in the warm waters of the Florida Keys.

Things to do recommended for groups

Groups visiting Summerland Key can enjoy a thrilling day of snorkelling at Looe Key National Marine Sanctuary and explore the vibrant marine life. In the evening, a sunset kayak tour offers a serene experience, allowing you to admire the stunning Florida Keys scenery together.

*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 travelling with a group, family, pets, or seeking longer stays, it's essential to filter based on your key priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Summerland Key with a group: Think about how many bedrooms you require, along with features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for all these options and more on Vrbo.
  • Traveling to Summerland Key with young kids: Travelling with young children can present its challenges. It's essential to prioritise their comfort and safety, along with ensuring access to 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 holiday isn’t truly finished without their furry companion by their side. If this resonates with you, be sure to explore Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of the family feels comfortable and at home.
  • Planning for a long term stay visiting Summerland Key: If you're seeking holiday rentals with special offers 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 such as a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in Summerland Key

Summerland Key offers a delightful tropical escape, perfect for outdoor enthusiasts and families alike. Explore its stunning beaches and indulge in water sports, from kayaking to snorkelling in the vibrant coral reefs. The island's laid-back atmosphere is complemented by friendly locals, creating a welcoming environment for all visitors. Don't miss the chance to experience the breathtaking sunsets that paint the sky over the Gulf, making Summerland Key a memorable destination in the Florida Keys.

  • Cudjoe Key: Nestled conveniently near Summerland Key, Cudjoe Key is a charming village surrounded by the stunning waters of the Florida Keys. This island locale is perfect for families seeking outdoor adventures, with a natural landscape that invites exploration. Visitors can enjoy a variety of activities, from shopping at local boutiques to unwinding at recreational areas. Notable attractions include pristine beaches and the breathtaking archipelago that characterises the region, making it an ideal spot for a relaxed yet engaging getaway.
  • Sugarloaf Key: Located just a stone's throw from Summerland Key, Sugarloaf Key is another island village that offers a delightful beach experience. Known for its family-friendly atmosphere, this destination is perfect for those looking to soak up the sun and enjoy outdoor activities. Sugarloaf Key features multiple shopping areas and recreational venues, ensuring visitors have ample opportunities for leisure. With its beautiful beaches and inviting family beach spots, Sugarloaf Key is a picturesque retreat for both relaxation and adventure.
  • Little Torch Key: Just a short drive from Summerland Key, Little Torch Key is a serene village ideal for those wanting to immerse themselves in nature. With its inviting outdoor spaces and beach access, it is a favourite among families. The area boasts several recreational facilities and shopping options, catering to diverse interests. Visitors can explore local beaches and family-friendly recreational areas, making it a perfect location for those seeking a balance of relaxation and outdoor fun amidst the enchanting landscape 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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
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

Booking with Vrbo is simple

Are you hoping to save on your next getaway? Being flexible with your travel dates can be beneficial, as prices often vary. Additionally, opting for a longer stay can lead to significant savings. To discover the ideal Vrbo property that fits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo's cutting-edge Trip Board offers you a convenient way to plan new trips, pick up from where you last left off, or manage and organise your travel plans. You can easily access the properties you’ve saved and booked, now sorted into categories such as Potential, Upcoming, or Current Trips. To start 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)
  • The Kite House (23.3 mi / 37.6 km)
  • Blue Hole (5.1 mi / 8.2 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.
How much does it cost to rent a holiday home in Summerland Key?
Prices for holiday rentals 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Summerland Key to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Summerland Key holiday house rentals?
You can find great discounts on house rentals in Summerland Key on Vrbo, 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.
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.
Can I find long-stay holiday rentals in Summerland Key?
A long-stay holiday rental 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 travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
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 Vrbo.
Are there any Summerland Key holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals 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 on Vrbo 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.
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.
How early should I book a Summerland Key holiday rental?
Book your Summerland Key holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price. *Based on analysis of Vrbo booking and occupancy data for 2024 stays.
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.
Can I change or cancel my Summerland Key home rental booking on Vrbo?
To find Summerland Key holiday rentals with free cancellation, just use Vrbo'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". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo 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, Vrbo 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 Vrbo handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Summerland Key holiday rental prices shown on Vrbo?
Vrbo 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way. Vrbo 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.
Can I plan a group trip on Vrbo?
Vrbo'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 favorites, and build the perfect itinerary together.

More holiday ideas