Summerland Key vacation rentals

We found 733 vacation rentals — enter your dates for availability

Select from 483 homes, 55 cottages, and other vacation rentals in Summerland Key to find one that's perfect for your trip. Whether you're traveling with family, friends, or just your furry companion, vacation rentals have the amenities you need and want for your stay, which might include parking and a fireplace. No matter what you're looking for, you'll be sure to find a rental for everyone's needs, including a place that is accessible or non-smoking.

Vacation rentals with weekly discounts - Summerland Key

Showing deals for:Dec 12 - Dec 19

Find out more about Summerland Key

Find out more about Summerland Key

Why visit Summerland Key

  • Stunning Beaches: Summerland Key features pristine beaches perfect for relaxation and family fun.
  • Outdoor Adventures: The area offers numerous outdoor activities, including kayaking, fishing, and snorkeling.
  • Charming Accommodations: Visitors can choose from cozy cottages to spacious vacation homes tailored to various preferences.
  • Scenic Natural Parks: Explore nearby national parks that showcase the unique flora and fauna of the Florida Keys.
  • Local Excursions: Engage with friendly locals on guided tours to discover hidden gems and local culture.

Popular types of accommodation in Summerland Key

Discover the charm of Summerland Key with a variety of vacation rentals to suit your needs. From cozy cottages and comfortable condos to spacious houses, there’s something for everyone. Enjoy the convenience of outdoor freezers for your catch of the day and friendly staff ready to assist you. Whether you’re seeking a relaxing getaway or an adventurous trip, Summerland Key has the perfect accommodation for your stay.

  • Houses: The top choice among travelers, these spacious homes offer a perfect setting for families and groups to relax and enjoy their stay in Summerland Key.
  • Condos: A popular option for vacationers, condos provide convenient amenities and often stunning views of the surrounding area.
  • Cottages: These charming retreats offer a cozy atmosphere, ideal for a romantic getaway or a peaceful solo escape.
  • Apartments: A great choice for budget-conscious travelers, apartments provide essential comforts and easy access to local attractions.
  • Villas: Luxurious and spacious, villas are perfect for those seeking an upscale experience in a tropical paradise.**

Top attractions in and around Summerland Key

Summerland Key is perfect for outdoor enthusiasts and families looking for a beach vacation. The area boasts a variety of attractions, including beautiful beaches, picturesque islands, and nearby national parks, making it an ideal destination for those seeking adventure and relaxation. Whether you're exploring the stunning coastline or enjoying outdoor activities, Summerland Key offers memorable experiences for all types of travelers.

  • Florida Keys Beaches: Located 8 miles from Summerland Key, this beach offers a quintessential tropical vibe with soft sands and crystal-clear waters, perfect for sunbathing and relaxation.
  • Upper Sugarloaf Sound: Nestled within Summerland Key, this scenic island features beautiful beaches and outdoor opportunities, making it ideal for kayaking, fishing, and enjoying the natural surroundings.
  • Upper Sugarloaf Key: A charming neighborhood within Summerland Key, it boasts a vibrant community atmosphere, with local shops and eateries that offer a taste of island life.

Things to do recommended for couples

For a romantic getaway in Summerland Key, consider water sports at Pigeon Key, located 18 miles away. Enjoy thrilling adventures and the great outdoors together, creating unforgettable memories in this picturesque setting.

Things to do recommended for families

Families visiting Summerland Key can explore the beautiful waters with a snorkeling adventure at John Pennekamp Coral Reef State Park and enjoy a fun day at the nearby Dolphin Research Center, where kids can learn about marine life and even interact with dolphins.

Things to do recommended for groups

In Summerland Key, groups can shop for unique finds at the Big Pine Key Flea Market, enjoy a round of golf at the Key West Golf Club, or experience culture and entertainment at the Tennessee Williams Fine Art Center, all within a short drive from your location.

*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

When planning your trip—whether you're traveling with a group, enjoying a family getaway, bringing your pets along, or seeking extended stays—it's important to prioritize your preferences. Here are some helpful booking tips for Vrbo to assist you.

  • Traveling to Summerland Key with a group: Think about how many bedrooms you require, as well as additional features like a complete kitchen or outdoor areas for group gatherings. Thankfully, you can easily refine your search for all these options and more on Vrbo.
  • Traveling to Summerland Key with young kids: Traveling with young kids can be quite a task. It's important to prioritize their comfort and safety, along with ensuring access to suitable amenities like a private pool. Additionally, it's wise to think about how close you are to attractions that are family-friendly.
  • Taking your pets with you to Summerland Key: For many families, a trip just isn't the same without their furry companions. If that resonates with you, take a look at Vrbo listings that welcome pets. Many of these pet-friendly properties offer amenities like food 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 vacation rentals offering 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 rental options. 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

Summerland Key offers a delightful blend of outdoor adventures and family-friendly activities in the beautiful Lower Florida Keys. Visitors can explore the tropical atmosphere, relax on pristine beaches, and enjoy excursions led by friendly locals. With its budget-friendly options and serene environment, Summerland Key is the perfect destination for those looking to unwind and experience the charm of the Florida Keys. Don't miss the chance to discover the hidden gems nearby.

  • Cudjoe Key: Cudjoe Key is a charming village located in the Florida Keys, just a stone's throw from Summerland Key. This picturesque island is perfect for families looking to enjoy the outdoors. Visitors can explore stunning beaches, engage in water sports, or relax in the serene surroundings. Cudjoe Key offers convenient access to shopping areas and recreational venues, making it easy to find everything you need for a fun-filled day. The nearby natural landmarks, including beautiful beaches and the breathtaking archipelago, invite exploration and adventure.
  • Little Torch Key: Little Torch Key is another idyllic village situated near Summerland Key, known for its stunning natural beauty and family-friendly atmosphere. This island is ideal for beach lovers and outdoor enthusiasts, with ample opportunities for swimming, snorkeling, and sunbathing. Guests can visit local recreational areas and shopping centers, ensuring a well-rounded vacation experience. The family beach nearby provides a perfect spot for relaxation and fun, making Little Torch Key an excellent choice for families seeking memorable moments and quality time together.
  • Sugarloaf Key: Sugarloaf Key is a delightful village located just a short distance from Summerland Key, offering visitors a unique blend of adventure and relaxation. This island is perfect for families who enjoy spending time outdoors, with access to beautiful beaches and recreational areas. Sugarloaf Key features shopping options nearby, allowing travelers to find local treasures and souvenirs. With its stunning natural surroundings and proximity to the archipelago, Sugarloaf Key is an ideal base for exploring the beauty of the Florida Keys while enjoying a peaceful retreat.

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

Are you hoping to save money on your upcoming journey? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, consider booking a longer stay to take advantage of substantial discounts. To discover a Vrbo property that aligns with your budget, utilize our filters to narrow down options by price, location, and type of rental. We're here to help you find the perfect place for your getaway.

Save more with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on the full booking amount. Being the planner has its perks. When you join our travel rewards program, One Key, you'll gain access to exclusive discounts and earn OneKeyCash on qualifying reservations. Sign up today and begin enjoying your savings.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board offers a user-friendly platform for planning your trips. You can easily create new itineraries, continue from where you last stopped, or organize your travel plans all in one place. Your saved or booked properties are neatly organized into categories: Potential, Upcoming, or Current Trips. To get started with Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Book a vacation rental for your Summerland Key getaway

Learn about the unique charm of Summerland Key with a stay in a private vacation home. You'll find plenty to explore during your stay in the area. Whether you're planning a family vacation, friends trip or romantic retreat, HomeAway has a great selection of vacation homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Where the cats have too many toes

Pick a key, any key. Summerland Key is a quiet, residential kinda place, so excursions might be on the menu. It's towards the western end of the Keys, meaning larger towns like Marathon and Key West are both around a half hour drive away. Macho literature aficionados will want to visit the Ernest Hemingway House in Key West, and see if they can count the toes on his resident mutant cats. While you're out that way, tour Harry S. Truman's Little White House, or take in some art at the Gallery on Greene and the Key West Historical Society.

The easiest Marathon you'll ever encounter

For such a laid-back place, a Summerland Key vacation rental gives you a lot of options. Fishermen can head over to the nearby sport-fishing capital of Marathon, or you could just stroll down to the water's edge and drop a line in. If you prefer to watch fish from a distance, then the snorkeling possibilities round here are immense. Try Looe Key marine sanctuary for something a bit special. Wildlife-watchers want to drive the 10 minutes to Big Pine Key, home to the dog-sized Key deer, or you could head a bit further out to the Dolphin Research Center.

Well they don't call it "Winterland," do they?

How does that saying go? Wherever you are in the world, the weather is probably better in the Keys. A Summerland Key vacation rental dishes up weather that you can only describe as tropical. The winter runs between November and May, though all "winter" means in the Florida Keys is that it doesn't rain as much. Otherwise it's still going to be balmy. You won't see a flake of snow, and in fact the temperature hasn't dropped below freezing since records began. As for summer, it'll be hot, and it'll pour with rain each afternoon. Bring a raincoat.

There's a reason those Key deer never leave

The Florida Keys are an archipelago off the coast of Florida, between the Gulf of Mexico and the Atlantic Ocean. They're actually the above-water bits of a massive coral reef that started forming more than a 100,000 years ago. Because the climate's so mild, all kinds of stuff thrives here that doesn't exist further north. Hell, some of it doesn't even exist outside the Keys, like Key deer and the Key Largo woodrat. And then there are the creatures that live in the water. Marine life is bountiful, but the crocodiles and the dolphins are the real celebrities.

Transportation options to and around Summerland Key

The nearest airport is in Key West Intl. Airport (EYW), located 20.9 mi (33.6 km) from the city center. If you can't find a flight that's convenient for your trip, you could 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 vacation rental?
When considering a vacation rental in Summerland Key, a popular area to stay is the Summerland Key Isles neighborhood. This picturesque community features a variety of waterfront properties, making it ideal for those who enjoy boating or fishing. With a good number of vacation rentals available, you can find charming homes that offer direct access to the water.

One of the top attractions nearby is the beautiful Looe Key National Marine Sanctuary, renowned for its stunning coral reefs and abundant marine life. This makes it a great spot for snorkeling and diving enthusiasts. Additionally, the relaxed atmosphere of the area allows you to unwind and enjoy the natural beauty of the Florida Keys.

Another appealing location within Summerland Key is the area around the iconic Summerland Key Park. This tranquil spot is great for leisurely walks, picnicking, and simply soaking in the views.
How much does it cost to rent a vacation home in Summerland Key?
Prices for vacation 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 vacation 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, Florida, travelers should explore the picturesque waterfront neighborhoods that offer direct access to the stunning Florida Keys waters. The area around the Summerland Key Canal is particularly appealing, where vacation rentals often come equipped with private boat docks, allowing for easy boating and fishing excursions. Many properties in this vicinity feature spacious outdoor decks, pools, and lush tropical landscaping, great for enjoying the warm climate and beautiful sunsets.

Another great option is the vicinity of the nearby Bahia Honda State Park, known for its pristine beaches and clear waters. Rentals here may offer amenities such as kayaks or paddleboards, providing guests with the opportunity to explore the natural beauty of the area. Properties in this area often have open-concept living spaces, modern kitchens, and large windows that bring in plenty of natural light, enhancing the vacation experience.

Additionally, the local area is rich in activities, with nearby attractions like the Looe Key Reef for snorkeling and diving, as well as various restaurants and shops that reflect the laid-back island lifestyle. Find your rental near the beach in Summerland Key.
What is the most popular type of vacation rental accomodation in Summerland Key?
In Summerland Key, vacation houses are the most popular type of accommodation, with approximately 457 options available throughout the area. These houses typically feature spacious layouts, multiple bedrooms, fully equipped kitchens, and outdoor patios or decks, ideal for enjoying the stunning waterfront views and the tropical climate. Many of these properties are located near the beach and offer easy access to local points of interest such as Looe Key National Marine Sanctuary and John Pennekamp Coral Reef State Park.

In addition to vacation houses, there are around 50 cottages that provide a charming, cozy atmosphere, often with quaint decor and essential amenities for a comfortable stay. For those seeking a great experience, about 28 campsites are available in the vicinity, allowing travelers to immerse themselves in nature. Mobile homes, although fewer in number at 19, also provide a budget-friendly option for visitors.
Are there any family house rentals in Summerland Key?
In Summerland Key, Florida, families will find an impressive selection of vacation rentals, with around 333 properties suiting group needs. This area is known for its stunning waterfront views and easy access to outdoor activities, making it an ideal spot for family getaways. Many of these homes offer spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces great for children to play or for family barbecues.

Visitors can enjoy amenities such as private pools, game rooms, and direct access to the water for fishing or kayaking, enhancing the overall experience. Nearby attractions include beautiful beaches and natural parks, which provide opportunities for hiking and exploring the unique Florida Keys ecosystem. See all family-friendly rentals in Summerland Key.
Can I rent a vacation home with a pool or hot tub in Summerland Key?
In Summerland Key, there are plenty of vacation homes available for rent that come equipped with pools and hot tubs, with around 363 options to choose from. This picturesque island community in the Florida Keys offers an inviting tropical atmosphere, superb for relaxation and recreation. Travelers can expect many amenities in these rentals, including private swimming pools, outdoor hot tubs, and spacious decks ideal for soaking up the sun. Many properties also feature fully equipped kitchens, providing the convenience of preparing meals after a day of exploration.

The area is known for its stunning waterfront views and easy access to activities such as boating, fishing, and snorkeling. Find your rental in Summerland Key with a pool or a hot tub.
Can I find long-stay vacation rentals in Summerland Key?
A long-stay vacation rental in Summerland Key is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* 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.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Summerland Key?
In Summerland Key, there are numerous pet-friendly house rentals available, with around 272 options to choose from. This beautiful community in the Florida Keys offers a range of vacation homes that often come with amenities such as private pools, outdoor patios, and fully equipped kitchens, making them great for families and groups traveling with pets.

Many of these rentals are situated close to the water, providing easy access to waterfront activities, and some properties even feature docks for boating enthusiasts. The serene environment and tropical landscapes enhance the experience, allowing guests to enjoy the outdoors with their furry companions.

Furthermore, nearby attractions like the National Key Deer Refuge offer scenic walking trails where pets are welcome, making it a great area for outdoor adventures. See all pet-friendly rentals in Summerland Key.
Are there any remote work vacation rentals in Summerland Key?
In Summerland Key, there are numerous vacation rentals that cater to remote work needs, with around 453 options available. This picturesque island destination offers a blend of tropical charm and modern amenities, making it great for those looking to work while enjoying a serene environment. Many properties come equipped with dedicated workspaces, including desks and ergonomic chairs, along with high-speed Wi-Fi to ensure reliable connectivity.

Travelers can expect amenities such as fully equipped kitchens, outdoor patios, and private pools, providing a comfortable and productive atmosphere. The area is known for its stunning waterfront views, making it easy to unwind after a day of work. Additionally, the proximity to local attractions like the nearby beaches and nature parks allows for a refreshing break during work hours. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Summerland Key vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Summerland Key with parking available—perfect for families or travelers 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 vacation rental amenities include WiFi, kitchens, and pools, making them ideal for travelers seeking comfort and convenience. Many rentals come equipped with a blender and a coffee/tea maker, allowing guests to prepare meals and enjoy coffee in the comfort of their accommodations.
When is the best time to visit Summerland Key for a vacation rental?
The best time to visit Summerland Key for a vacation rental is during the summer months, particularly in July. This is when the area truly comes alive, attracting sun-seekers and water enthusiasts eager to enjoy the warm, tropical climate. With temperatures typically hovering in the mid-80s to low 90s Fahrenheit, July provides great conditions for swimming, snorkeling, and exploring the vibrant marine life that the Florida Keys are famous for.

As you plan your adventure, keep in mind that the peak tourist season extends from July to September. This period offers a wealth of outdoor activities, including kayaking through the serene mangroves and soaking up the sun on pristine beaches. The lively atmosphere is enhanced by local events and festivities, making it an ideal time for those looking to connect with fellow travelers and experience the local culture.

For those seeking a more budget-conscious option, consider visiting in October. This month presents a wonderful opportunity to enjoy the area's natural beauty without the crowds, as the weather remains pleasant, with temperatures typically in the low 80s Fahrenheit. You can still partake in outdoor activities like fishing and hiking, all while benefiting from lower rental rates.

Ultimately, whether you choose the vibrant summer season or the quieter fall months, Summerland Key promises unforgettable experiences tailored to your preferences.
How early should I book a Summerland Key vacation rental?
Book your Summerland Key vacation 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 vacation 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 range of attractions within this beautiful island community. The area is known for its stunning waterfront views and access to various water activities, making it a prime spot for fishing, snorkeling, and kayaking. Vacation rentals near the Summerland Key Marina offer convenient access to boat rentals and fishing charters.

For those interested in nature, the nearby Florida Keys National Marine Sanctuary provides opportunities for eco-tourism and exploration of the vibrant marine life. The relaxed atmosphere of Summerland Key is complemented by local dining options, where visitors can savor fresh seafood and enjoy the laid-back island vibe. Additionally, the nearby Bahia Honda State Park offers beautiful beaches and hiking trails, appealing to outdoor enthusiasts.
Can I change or cancel my Summerland Key home rental booking on Vrbo?
To find Summerland Key vacation 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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Summerland Key vacation 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.

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