Summerland Key holiday lettings

We found 741 holiday rentals — enter your dates for availability

Select from 472 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.

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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.

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.

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

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.

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)
  • 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.

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