Summerland Key vacation rentals

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Select from 469 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

Find out more about Summerland Key

Why visit Summerland Key

  1. Outdoor Adventures: Enjoy a variety of activities such as kayaking, fishing, and snorkeling in the stunning waters of the Florida Keys.
  2. Beautiful Beaches: Relax on picturesque beaches, perfect for sunbathing and swimming with family and friends.
  3. Charming Accommodations: Choose from delightful vacation rentals, including cottages and condos, offering comfort and convenience.
  4. Nearby Attractions: Explore the vibrant atmosphere of nearby Key West, known for its lively excursions and romantic spots.
  5. Family-Friendly Atmosphere: Experience a welcoming environment ideal for families and couples seeking adventure and tranquility.

Popular types of accommodation in Summerland Key

If you're considering a getaway to Summerland Key, you're in for a treat! Our most popular vacation rentals include houses, condos, and charming cottages, perfect for any traveller. Explore the beauty of the Florida Keys while enjoying the comfort and convenience of a well-appointed vacation home. With a variety of options available, you can find the ideal spot to relax and soak up the sun in Summerland Key.

  • Houses: The top choice for visitors in Summerland Key, offering spacious accommodations perfect for families or groups seeking a home-like atmosphere.
  • Condos: A popular option for those looking for a blend of comfort and convenience, ideal for couples or small families.
  • Cottages: Charming and cozy, these rentals provide a quaint escape for those wanting a more intimate setting.
  • Apartments: A practical choice for short stays, offering essential amenities in a compact space.
  • Villas: Luxurious and spacious, perfect for an upscale vacation experience with stunning views.**

Top attractions in Summerland Key

Summerland Key offers a perfect getaway for outdoor enthusiasts and families alike, featuring stunning beaches and picturesque islands. Visitors can explore various points of interest, including national and state parks, providing ample opportunities for adventure and relaxation. Whether you're seeking a beach day or an adventurous excursion, Summerland Key has something for everyone, making it an ideal destination for a memorable vacation.

  1. Florida Keys Beaches: A picturesque beach located 12.9km from Summerland Key, offering stunning views and a laid-back atmosphere. Enjoy sunbathing, swimming, and the refreshing ocean breeze.
  2. Upper Sugarloaf Key: This charming neighbourhood within Summerland Key boasts a vibrant community feel, with local shops and restaurants that reflect the unique culture of the Florida Keys.
  3. Upper Sugarloaf Sound: An idyllic island perfect for outdoor enthusiasts, featuring beautiful beaches and opportunities for kayaking, snorkeling, and enjoying the natural beauty of the area.

Things to do recommended for couples

For a romantic getaway in Summerland Key, consider a visit to Pigeon Key, located 112.9km away. Engage in exciting water sports together, surrounded by stunning outdoor scenery. It’s the perfect spot for couples seeking adventure and connection in a beautiful setting.

Things to do recommended for groups

Explore the vibrant Big Pine Key Flea Market for unique finds, enjoy a round of golf at the scenic Key West Golf Club, or immerse yourselves in culture at the Tennessee Williams Fine Art Center, all within a short drive from Summerland Key.

What do I need to keep in mind when booking a vacation in Summerland Key

When planning your trip—whether with a group, family, pets, or for an extended stay—it's important to prioritise your needs in the search. Here are some helpful Vrbo booking tips for you.

  • Traveling to Summerland Key with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor space for group gatherings. The good news is that you can easily filter for these options and many more on Vrbo.
  • Traveling to Summerland Key with young kids: Traveling with young children can present its difficulties. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, considering your closeness to family-friendly attractions is a wise choice.
  • Taking your pets with you to Summerland Key: For many families, a trip isn't truly fulfilling without their furry companion by their side. If this resonates with you, 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 searching for 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 accommodations. Don't forget to include options such as a parking spot, a well-equipped kitchen, or a private pool in your search criteria.

Where to stay in Summerland Key

Summerland Key offers a delightful blend of outdoor adventure and relaxation in the beautiful Florida Keys. Ideal for families and couples alike, you'll find stunning beaches and friendly locals welcoming you. Nearby, the vibrant atmosphere of Key West beckons with its lively excursions and romantic spots. This picturesque destination is the perfect getaway for those seeking both adventure and tranquility in a budget-friendly setting.

  • Cudjoe Key: Nestled in the beautiful Florida Keys, Cudjoe Key is a picturesque village known for its stunning natural surroundings. Located just a short drive from Summerland Key, this island paradise offers visitors a tranquil escape with a focus on outdoor activities and family-friendly experiences. Enjoy the local beaches and explore the vibrant archipelago, while indulging in recreational activities like fishing and kayaking. Shopping enthusiasts will also find several options, including local boutiques and a shopping mall centre that showcases the unique charm of the Keys.
  • Sugarloaf Key: A gem in the Florida Keys, Sugarloaf Key is famed for its serene atmosphere and family-oriented adventures. This quaint village, located near Summerland Key, provides easy access to stunning beaches and lush landscapes. Visitors can partake in various outdoor activities, from biking to snorkeling, while the local shopping areas and mall centre offer a chance to pick up unique souvenirs. Sugarloaf Key's proximity to the archipelago makes it a perfect spot for exploring the beauty of the surrounding waters and enjoying the laid-back island lifestyle.
  • Little Torch Key: Little Torch Key is a charming island village, perfectly situated close to Summerland Key. This destination is ideal for outdoor enthusiasts and families alike, with pristine beaches and recreational areas that invite relaxation and exploration. Visitors can enjoy various activities, including fishing, swimming, and picnicking, along the beautiful shoreline. The local shopping area and mall centre provide a variety of options for those looking to experience the local culture and find keepsakes from their trip, making Little Torch Key a delightful addition to your vacation itinerary.

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 upcoming journey? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, you can enjoy considerable savings by opting for an extended stay. To discover a Vrbo property that suits your budget, feel free to utilise our filters to sort by price, location, and type of vacation rental.

Vrbo Trips: Planning made easy

Vrbo's cutting-edge Trip Board offers you a convenient platform to plan new getaways, pick up right where you left off, or effectively manage your travel arrangements. You can easily locate properties you've saved or booked under Potential, Upcoming, or Current Trips. To explore the Trip Boards, simply visit: https://www.vrbo.com/en-ca/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, Vrbo 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.

Activities and attractions in and around Summerland Key

Are you hoping to find attractions to visit in the city? Venture out of your cozy vacation rental and experience everything that makes Summerland Key a fun place to get away. These are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • 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 active traveler or just want to take in the scenery, Summerland Key is a great place to get outside. These are some of the area's most stunning features, all within 30 miles (48.2 km) of the city center:

  • 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)
  • Boca Chica Nude Beach (16.4 mi / 26.4 km)
  • Key West Tropical Forest and Botanical Garden (20 mi / 32.3 km)

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 most popular type of vacation rental accommodation in Summerland Key?
According to our research, houses are considered the most popular vacation rental type in Summerland Key. But naturally, everyone’s idea of an awesome stay isn’t going to be the same. Vrbo has vacation rentals in a variety of shapes and sizes, so you’re bound to find your perfect match.
How much does it cost to rent a vacation rental in Summerland Key?
Length of stay, season and property type are some things that can influence the price of a vacation home. Simply click on your dates of travel to find the ultimate escape. From comfy cabins to expansive luxury villas, all Vrbo vacation rentals provide unbeatable value.
How much does it cost to rent a beach house in Summerland Key?
The average price for a vacation home close to the beach in Summerland Key will depend on when you’re going and the size and type of property you’re looking for. Find prices quickly and easily on Vrbo by entering your destination and travel dates. Then use the filters to pick the number of bedrooms and amenities important to you, like air conditioning, WiFi and a hot tub.
Are there pet-friendly vacation rentals in Summerland Key?
Pack a bone and a squeezy toy for the pup in your life because Summerland Key has 29 vacation rentals that roll out the welcome mat to pets. Let your four-legged friend get in on the family fun at one of our pet-friendly vacation rentals on Vrbo. Simply enter your dates then check the “Pets allowed” filter box.
Can I rent a house with a pool in Summerland Key?
Tick the “pool” box in our filter tool and pick from 23 houses with private pools in Summerland Key on Vrbo. Morning dip, sunset soak or midnight swim? Downtime is up to you when your vacation home comes with its own swimming pool.
What are popular rental amenities in Summerland Key?
A firepit, a swimming pool and a barbecue grill are rated the most popular rental amenities in Summerland Key. Whether you’re taking to the road on your own, with your significant other or a group of friends, Vrbo can help you find a vacation rental that matches your tastes with all the features you need.
Are there large group vacation rentals in Summerland Key?
There are nine vacation homes in Summerland Key that can accommodate a group of 10 or more guests. Whether you’re planning time away with the family or an event like an anniversary, there’s enough space to get your group together under one roof.
Are there vacation rentals in Summerland Key that welcome kids?
Gather your entire family for an epic adventure in Summerland Key at one of our 29 family-friendly properties. A lot of these stays come with amenities that are great for getaways with children, such as laundry facilities, multiple bedrooms and entertainment units. Just check the “Properties good for families” filter and choose your favorite option.
What are the top attractions for families in Summerland Key?
Keeping the kids amused during your stay in Summerland Key is a snap with these fabulous family-friendly attractions:

  • Florida Keys Beaches
  • Sugarloaf Beach
  • National Key Deer Refuge Visitor Center

Are there one-bedroom vacation rentals in Summerland Key?
Yes, there are two one-bedroom properties in Summerland Key to select from. A one-bedroom vacation property is a wonderful choice if it’s just you and your sweetheart or if you’re traveling alone. Toss in more privacy, convenience and space compared to a regular hotel, and you’ve got yourself an unforgettable trip.
Can I find two-bedroom vacation rentals in Summerland Key?
Pick from six two-bedroom vacation rentals in Summerland Key. Settle the kids into the second room or fill it with a couple of your nearest and dearest friends. There’s a comfy spot for whoever’s lucky enough to be joining in on the fun.
Are there vacation rentals with WiFi in Summerland Key?
Pick from nine vacation rentals with WiFi in Summerland Key. If you’d like to disconnect from daily life during your break, but still need to be connected to the web, these properties have just what you need. Narrow your search by applying the WiFi filter on Vrbo.
How can I find vacation rentals with air conditioning in Summerland Key?
You can choose from 28 Vrbo vacation homes with air conditioning in Summerland Key offering that cooling breeze and extra touch of comfort. Enter your travel dates and then use our filter tool to find properties with air conditioning.
How old do you have to be to rent a vacation rental in Summerland Key?
The age limit can differ across properties on Vrbo, so check the rules of the vacation rental in Summerland Key you want to book. But in general, it’s 16, 18 or 21.
How long can I rent a vacation rental in Summerland Key for?
It really depends on the Summerland Key property. To browse a list of options offering extended stays, simply enter your travel dates and guest number into Vrbo. Look forward to having the entire place to yourself, along with comforts such as a full kitchen, air conditioning and outdoor spaces where the kids can burn off energy. Keep your eyes open for long-term stays that offer discounted weekly or monthly prices.

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