Summerland Key vacation rentals

We found 729 vacation rentals — enter your dates for availability

Select from 466 homes, 52 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.
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Find out more about Summerland Key

Why visit Summerland Key

  • Stunning Beaches: Summerland Key boasts beautiful beaches perfect for sunbathing, swimming, and relaxing.
  • Outdoor Adventures: Engage in activities like kayaking to explore the breathtaking waters and marine life.
  • Charming Local Atmosphere: Experience the friendly locals and laid-back vibe of this tropical paradise.
  • Vacation Rentals: Choose from a variety of accommodations, including cozy cottages and stylish condos.
  • Proximity to National Parks: Explore the nearby lower Florida Keys and enjoy unique natural attractions.

Popular types of accommodation in Summerland Key

Planning a getaway to Summerland Key? You're in for a treat. This stunning destination offers a variety of vacation rentals, including houses, cozy cottages, and stylish condos. Whether you're seeking a relaxing retreat or an adventure-filled escape, you'll find the perfect summerland key vacation rental to suit your needs. Explore key house rentals and discover your ideal vacation home in Summerland Cove for an unforgettable experience.

  • Houses: The top choice for visitors, these homes offer spacious accommodations perfect for families or groups seeking privacy and comfort.
  • Condos: These units provide a balance of convenience and amenities, ideal for couples or small families wanting easy access to local attractions.
  • Cottages: Quaint and charming, cottages in Summerland Key offer a cozy retreat for those looking for a more intimate vacation experience.
  • Apartments: A practical option for travelers seeking affordable stays with essential amenities in a home-like setting.
  • Villas: These luxurious properties provide a lavish experience, complete with upscale features and stunning views.**

Top attractions in Summerland Key

Summerland Key offers a perfect getaway for outdoor and beach enthusiasts, making it ideal for family vacations. Visitors can enjoy various attractions, including beautiful beaches, scenic islands, and nearby national parks. For adventure seekers, kayaking is a popular activity to explore the stunning waters around Summerland Key. Whether you're traveling solo or with loved ones, there's plenty to discover in this tropical paradise.

  • Sugarloaf Beach: Enjoy the serene beach vibes at Sugarloaf Beach, where soft sands and gentle waves create the perfect setting for relaxation and sunbathing.
  • Upper Sugarloaf Sound: Explore the outdoor paradise of Upper Sugarloaf Sound, an island offering stunning views and a tranquil atmosphere, ideal for kayaking and fishing.
  • Upper Sugarloaf Key: Experience the charm of Upper Sugarloaf Key, a vibrant neighborhood with a local feel, featuring shops, dining, and a welcoming community vibe.

Things to do recommended for couples

Summerland Key offers a perfect romantic getaway for couples. Enjoy a sunset picnic on the beach, indulge in a candlelit dinner at a waterfront restaurant, or explore the vibrant coral reefs together while snorkeling. Create unforgettable memories in this idyllic tropical paradise.

Things to do recommended for families

Families can explore the beautiful beaches of Summerland Key, enjoy kayaking through mangroves, or take a snorkeling trip to see vibrant marine life. Don't miss the chance to visit local parks for picnics and play, creating unforgettable memories together.

Things to do recommended for groups

Groups visiting Summerland Key can enjoy snorkeling in the crystal-clear waters of the Florida Keys National Marine Sanctuary and embark on a fun-filled fishing charter. Don't miss a sunset cruise to witness the breathtaking views and vibrant colors of the Gulf of Mexico.

*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 traveling with a group, enjoying a family getaway, bringing along your pets, or planning an extended stay, be sure to refine your search based on what matters most to you. Here are some helpful booking tips for using Vrbo.

  • Traveling to Summerland Key with a group: Think about how many bedrooms you'll require, along with additional features like a full kitchen or outdoor area for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Summerland Key with young kids: Traveling with young kids can be quite demanding. It’s important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, thinking about your closeness to family-friendly attractions is a wise choice.
  • Taking your pets with you to Summerland Key: For many, a family vacation isn't truly fulfilling without their furry companion by their side. If this resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and cozy 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 that offer 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 as well.

Where to stay in Summerland Key

Summerland Key, a charming island city in the Florida Keys, offers a tropical paradise perfect for outdoor adventures and family vacations. Explore the nearby lower Florida Keys, where friendly locals create a relaxing atmosphere. Enjoy excursions to stunning beaches and discover the unique character of this vibrant region. Whether you're seeking budget-friendly activities or unforgettable experiences, Summerland Key and its surroundings have something for everyone.

  • Cudjoe Key: Nestled in the scenic Florida Keys, Cudjoe Key is a charming village that offers a delightful island experience, just a short drive from Summerland Key. Known for its beautiful beaches and outdoor activities, this locale is perfect for families looking to enjoy nature. Visitors can explore shopping areas and recreational venues, making it a great spot for both relaxation and adventure. Local attractions include pristine beaches and the enchanting island landscape, which is part of the stunning archipelago of the Keys.
  • Sugarloaf Key: Sugarloaf Key is another idyllic island village located near Summerland Key, known for its serene beaches and family-friendly atmosphere. This destination is ideal for outdoor enthusiasts and beach lovers alike. Visitors can enjoy various recreational activities, along with convenient access to shopping areas and local markets. The key's highlights include beautiful sandy beaches and family-oriented beach spots, providing ample opportunities for sun-soaked fun and relaxation.
  • Little Torch Key: Located just a stone's throw from Summerland Key, Little Torch Key is a picturesque village renowned for its natural beauty and outdoor experiences. Families will appreciate the recreational areas and shopping spots available, making it a well-rounded destination for visitors. The local attractions include stunning beaches and family-friendly beach areas, ensuring a memorable time in this tranquil island setting. Engage in various outdoor activities, soak up the sun, or explore the vibrant island life that characterizes Little Torch Key.

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 cut costs on your upcoming trip? One effective strategy is to remain flexible with your travel dates, as prices can vary significantly. Additionally, booking a longer stay often leads to substantial savings. To help you discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental.

Vrbo Trips: Planning made easy

Vrbo's Trip Board offers a user-friendly platform for planning your next adventure. You can easily start new trips, resume planning from where you last stopped, or manage your existing itineraries. All the properties you've saved or booked are neatly organized under categories like Potential, Upcoming, or Current Trips. To begin exploring 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, Florida, United States of America when booking a vacation rental?
When considering a vacation rental in Summerland Key, a popular area to stay is along the waterfront. This neighborhood offers stunning views and easy access to the beautiful waters of the Florida Keys, making it an ideal spot for those who enjoy boating, fishing, or simply relaxing by the shore.

In this area, you can find a variety of properties, with many boasting private docks and outdoor spaces great for enjoying the warm sunshine. Nearby, you can explore the charming local attractions, such as the serene beaches and vibrant natural surroundings, which are great for outdoor activities like kayaking and snorkeling. Additionally, the nearby Looe Key Reef is a top destination for divers, featuring some of the most breathtaking underwater scenery in the region.
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, travelers should focus on the serene waterfront neighborhoods that offer direct access to the stunning waters of the Florida Keys. The area around the Summerland Key Marina is particularly appealing, where properties often feature private docks, making it easy for boating enthusiasts to enjoy the surrounding waters. Many beach houses in this locale come equipped with outdoor spaces such as spacious decks, swimming pools, and barbecue areas, ideal for entertaining and enjoying the tropical climate.

Another great area to consider is the vicinity of the Summerland Key Nature Preserve, where visitors can find charming homes with lush landscaping and proximity to tranquil beaches. Properties here typically offer amenities like kayaks or paddleboards for exploring the nearby mangroves and calm bays, as well as comfortable living areas with large windows to take in the picturesque views.

Travelers can also explore the neighborhoods closer to the Atlantic coastline, where beachfront rentals may feature private beach access, outdoor showers, and hammock setups for relaxing by the shore. The local area includes various dining options and grocery stores, ensuring convenience for families and groups.
What is the most popular type of vacation rental accomodation in Summerland Key?
In Summerland Key, vacation houses are the predominant type of rental, with about 449 available throughout the area. These homes often feature spacious layouts, multiple bedrooms, fully equipped kitchens, and outdoor spaces such as decks or patios, great for enjoying the tropical climate. Many properties are situated near the waterfront, providing easy access to beautiful views and recreational activities like boating and fishing.

Additionally, there are around 48 cottages for those seeking a cozier option, typically equipped with essential amenities and often located in quieter, picturesque settings. For a great experience, about 30 campsites and 20 mobile homes offer travelers a more rustic stay, allowing guests to immerse themselves in nature while still enjoying basic comforts. Meanwhile, several villas provide a touch of luxury with upscale amenities and private pools, suiting those looking for an elegant getaway.
Can I rent a vacation home with a pool or hot tub in Summerland Key?
In Summerland Key, there are many vacation homes available for rent that include pools and hot tubs, with approximately 383 options to choose from. This beautiful Florida Keys location is known for its stunning waterfront properties and relaxed island atmosphere. Travelers can find homes in various neighborhoods, including those directly on the water with private docks, making them superb for boating enthusiasts.

Many of these rentals feature private pools and hot tubs, outdoor patios for sunbathing, and fully equipped kitchens for convenient meal preparation. Additionally, travelers can expect amenities such as air conditioning, Wi-Fi, and spacious living areas designed for relaxation and family gatherings.
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, travelers will find a wide selection of pet-friendly house rentals, with approximately 292 options available. Many of these vacation homes are situated along the scenic waterfront, providing stunning views and easy access to the water for activities like kayaking and fishing. Expect amenities such as private pools, outdoor patios, and fully equipped kitchens, superb for families or groups traveling with pets.

The area also offers pet-friendly points of interest, including nearby parks and beaches where pets can enjoy the sunshine and outdoor activities.
Are there any remote work vacation rentals in Summerland Key?
In Summerland Key, there are numerous vacation rentals suited for remote work, with around 473 options available. This picturesque area in the Florida Keys offers a great blend of relaxation and productivity. Many properties come equipped with essential amenities such as high-speed Wi-Fi, dedicated office spaces, and desks, ensuring a comfortable work environment.

You can expect to find a variety of accommodations, including waterfront homes with beautiful views, outdoor spaces for breaks, and fully equipped kitchens to prepare meals during your workdays. The serene surroundings, with nearby attractions like the National Key Deer Refuge and local beaches, provide an ideal backdrop for balancing work and leisure. 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, vacation rentals commonly feature amenities that cater to a comfortable and enjoyable stay. Travelers can expect properties equipped with kitchens, allowing for convenient meal preparation. Many rentals also boast decks or patios, great for soaking up the sun and enjoying the beautiful surroundings. Onsite parking is typically available, making it easy for guests to explore the area. Additionally, rentals often include coffee and tea makers for those cozy mornings. Many units also offer balconies, providing a lovely spot to relax and take in the scenic views of this picturesque Florida destination.
When is the best time to visit Summerland Key for a vacation rental?
The peak travel season in Summerland Key typically runs from July to September, making it the most vibrant time to experience the area. July, in particular, stands out as a popular month, drawing visitors eager to soak up the sun, enjoy water sports, and explore the stunning natural beauty of the Florida Keys. The warm temperatures, averaging in the high 80s to low 90s Fahrenheit, create an inclusive setting for outdoor activities such as snorkeling, kayaking, and fishing in the crystal-clear waters.

During the summer months, tourists flock to the region for its lively ambiance and numerous events, particularly the summer festivals that celebrate local culture and cuisine. This bustling environment is great for travelers who thrive on excitement and want to connect with fellow adventurers.

If you're looking for a more budget-friendly option, consider visiting in October. This month offers a delightful opportunity to enjoy the pleasant weather while avoiding the peak crowds. You can still partake in various outdoor activities, relish the serene beaches, and appreciate the beautiful sunsets without the hustle and bustle of the summer season.

Ultimately, the best time to book a vacation rental in Summerland Key depends on your preferences for activity level and atmosphere.
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, Florida, United States of America?
In Summerland Key, travelers can enjoy a variety of attractions that highlight the natural beauty and laid-back lifestyle of the Florida Keys. One of the main draws is the stunning waterfront scenery, with opportunities for fishing, kayaking, and paddleboarding. The area is known for its beautiful beaches, such as the nearby Sombrero Beach, where visitors can relax and soak up the sun.

For those interested in marine life, the John Pennekamp Coral Reef State Park in Key Largo, a short drive away, offers snorkeling and diving experiences among vibrant coral reefs. The nearby National Key Deer Refuge provides a chance to see the endangered Key deer in their natural habitat, along with scenic walking trails.
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 cabin or a beach condo, 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 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.
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 like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, 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 organizing 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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