Summerland Key vacation rentals
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Old Florida Style, wrap around porch, boat basin for dockage, open water
Top rated rentals - Summerland Key
GIRLS TRIP -- (ran out of room below, would give this place 10 stars if I could!)
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All the privacy of homeEnjoy full kitchens, laundry, pools, yards and more
More for lessMore space, more privacy, more amenities — more value
Find out more about Summerland Key
Find out more about Summerland Key
Why visit Summerland Key
- Stunning Beaches: Enjoy beautiful beaches like Sunset Beach, perfect for family outings and romantic sunsets.
- Outdoor Adventures: Dive into vibrant underwater life with snorkeling gear and explore the natural beauty of the area.
- Rich Local Culture: Immerse yourself in the history and culture of Summerland Key through various excursions.
- Variety of Accommodations: Choose from spacious vacation homes, cozy cottages, and modern condos for your stay.
- Family-Friendly Activities: Engage in a range of activities that cater to both families and outdoor enthusiasts.
Popular types of accommodation in Summerland Key
Planning a getaway to Summerland Key? Exciting times await as you choose your perfect home away from home! Explore a range of popular vacation rentals, including charming cottages, spacious houses, and luxurious villa rentals. Don't miss the chance to stay at Sailfish Manor for a truly memorable experience. Dive into the options and find the ideal accommodation that suits your needs for a fantastic vacation!
- Condos: These are highly sought-after accommodations, accounting for 32% of vacation rentals in Summerland Key, ideal for those seeking a blend of comfort and amenities.
- Cottages: Charming and cozy, cottages make up 23% of rentals, perfect for a quaint getaway in a picturesque setting.
- Houses: Comprising 17% of options, these homes offer spacious living, great for families or groups wanting privacy.
- House Boats: Unique and adventurous, house boats represent 13% of rentals, allowing you to experience life on the water.
- Apartments: Making up 12% of accommodations, apartments provide a convenient stay, often in vibrant areas.**
Top attractions in Summerland Key
Summerland Key offers a perfect blend of outdoor adventures and family-friendly activities, making it an ideal vacation spot. Visitors can enjoy beautiful beaches, explore historic houses, and immerse themselves in local culture. For those seeking adventure, snorkeling gear is available to discover the vibrant underwater life. With a variety of attractions catering to beach lovers and outdoor enthusiasts, Summerland Key promises an unforgettable getaway for everyone.
- Florida Keys Beaches: A stunning beach located 8 miles from Summerland Key, offering pristine sands, crystal-clear waters, and a laid-back atmosphere perfect for sunbathing and swimming.
- Upper Sugarloaf Key: A charming neighborhood within Summerland Key, showcasing a vibrant community feel with local shops, dining options, and a welcoming ambiance that reflects the island lifestyle.
- Upper Sugarloaf Sound: A beautiful island featuring outdoor activities, ideal for kayaking, paddleboarding, and enjoying scenic beach vibes amidst nature's tranquility.
Things to do recommended for couples
For a romantic getaway in Summerland Key, consider a visit to Pigeon Key, located 18 miles away. Enjoy exhilarating water sports and embrace the outdoor adventure vibes together. It's the perfect blend of excitement and romance for couples looking to create lasting memories.
Things to do recommended for groups
Groups visiting Summerland Key can explore the vibrant Big Pine Key Flea Market for local treasures, enjoy a round of golf at the scenic Key West Golf Club, and immerse themselves in culture at the Tennessee Williams Fine Art Center, perfect for entertainment and family bonding.
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, family, pets, or seeking extended stays, it's important to prioritize your preferences. Here are some helpful tips for booking on Vrbo.
- Traveling to Summerland Key with a group: Think about how many bedrooms you require, along with features like a full kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for all these options and more on Vrbo.
- Traveling to Summerland Key with young kids: Traveling with young kids can be difficult. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, thinking about how close you are to family-friendly attractions can make a big difference in your experience.
- Taking your pets with you to Summerland Key: For many, a family vacation isn't truly fulfilling without their furry companions. If this resonates with you, take a look at Vrbo listings that welcome pets. Many of these pet-friendly accommodations offer amenities like 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 in search of vacation rentals that offer special rates 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 amenities 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 tranquil island getaway perfect for outdoor enthusiasts and families alike. Explore pristine shores and enjoy the breathtaking sunsets at Sunset Beach, where the atmosphere is romantic and family-friendly. This hidden gem invites you to experience the beauty of nature while indulging in excursions that highlight the area's rich history. Discover the charm of Summerland Key and create unforgettable memories in this tropical paradise.
- Key West: Key West, located 24 miles from Summerland Key, is a vibrant island city known for its lively atmosphere and rich history. Travelers flock here for a mix of family, city, and business experiences. Key West boasts an array of attractions, including beautiful beaches, bustling shopping areas, and charming streets filled with local art and culture. Don't miss the iconic Southernmost Point buoy, historic landmarks like Ernest Hemingway's home, and the breathtaking sunset celebrations at Mallory Square. With excellent dining options and a laid-back vibe, Key West is a must-visit destination for anyone exploring the Florida Keys.
- Sugarloaf Shores: Nestled around Summerland Key, Sugarloaf Shores is a serene neighborhood perfect for outdoor and beach enthusiasts. This picturesque area offers a relaxed atmosphere with opportunities for family-friendly activities. Visitors can explore nearby beaches, indulge in recreational activities, and browse local shopping areas. The neighborhood is known for its stunning waterfront views and proximity to natural attractions, making it ideal for a day of sun and fun. Whether enjoying a beach picnic or taking a stroll along the shore, Sugarloaf Shores provides a peaceful escape in the Florida Keys.
- Cutthroat Harbor Estates: Located near Summerland Key, Cutthroat Harbor Estates is a delightful neighborhood that caters to adventure seekers and beach lovers. The area offers plenty of outdoor activities, including water sports and recreational areas to explore. Visitors can enjoy beautiful beaches and stunning island views, as well as various shopping options. With its inviting atmosphere and focus on outdoor adventures, Cutthroat Harbor Estates is an excellent choice for those looking to immerse themselves in the natural beauty of the Florida Keys while enjoying exciting activities.
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 Month |  Temperature |  Precipitation |  Cloudiness |  Occupancy |  Pricing |
| January | 71.1°F (21.7°C) | No Rain (Dry) | Mostly Sunny | Average | Average |
| February | 72.1°F (22.3°C) | No Rain (Dry) | Mostly Sunny | Average | Slightly High |
| March | 73.2°F (22.9°C) | No Rain (Dry) | Mostly Sunny | Slightly High | Slightly High |
| April | 76.8°F (24.9°C) | No Rain (Dry) | Mostly Sunny | Slightly High | Slightly High |
| May | 79.3°F (26.3°C) | Light Rain | Mostly Sunny | Slightly Low | Average |
| June | 82.6°F (28.1°C) | Light Rain | Mostly Sunny | Average | Average |
| July | 84.0°F (28.9°C) | Light Rain | Mostly Sunny | Slightly High | Average |
| August | 84.4°F (29.1°C) | Light Rain | Mostly Sunny | Average | Slightly Low |
| September | 83.7°F (28.7°C) | Light Rain | Mostly Sunny | Average | Slightly Low |
| October | 80.8°F (27.1°C) | Light Rain | Mostly Sunny | Slightly Low | Average |
| November | 76.6°F (24.8°C) | Light Rain | Mostly Sunny | Slightly Low | Slightly Low |
| December | 73.8°F (23.2°C) | No Rain (Dry) | Mostly Sunny | Average | Average |
Booking with Vrbo is simple
Are you hoping to save on your upcoming trip? Flexibility with your travel dates can lead to significant savings, as prices can vary. Additionally, booking a longer stay often results in greater discounts. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to narrow down your options by price, location, and type of vacation rental.
Save more with One Key
Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash™ on your total booking amount. Being the planner truly has its rewards! When you join our travel rewards program, One Key, you’ll gain access to exclusive member discounts and earn OneKeyCash™ on eligible bookings. Sign up today and begin enjoying your savings!
Vrbo Trips: Effortless planning
Vrbo’s Trip Board offers an easy and organized way to plan your trips, allowing you to start new adventures, continue from where you paused, or keep track of your travel plans. You can easily access your saved or booked properties, which are neatly categorized as Potential, Upcoming, or Current Trips. To begin utilizing Trip Boards, simply visit: https://www.vrbo.com/trips.
**Percentages are based on Vrbo properties booked during 2023 and 2024.
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.