Summerland Key vacation rentals

We found 756 vacation rentals — enter your dates for availability

Select from 494 homes, 56 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, relaxing beaches ideal for sunbathing and family fun.
  • Outdoor Adventures: Explore nearby national parks and islands, perfect for hiking, kayaking, and wildlife viewing.
  • Family-Friendly Atmosphere: Enjoy a welcoming community with activities suitable for all ages, ensuring memorable family vacations.
  • Charming Accommodations: Choose from a variety of vacation rentals, including cozy cottages and stylish condos, to suit your budget.
  • Tropical Ambiance: Immerse yourself in the vibrant natural surroundings and laid-back lifestyle of the Florida Keys.

Popular types of accommodation in Summerland Key

Vrbo offers a variety of vacation rentals in Summerland Key, perfect for any Canadian traveller. Choose from houses, cozy cottages, or stylish condos to suit your needs. Whether you’re seeking a relaxing getaway or a fun-filled adventure, you’ll find the right fit among our Summerland Key accommodations. With key amenities and transparent pricing, planning your ideal vacation has never been easier.

  • Houses: The top choice for visitors seeking a spacious and comfortable stay in Summerland Key, ideal for families or groups.
  • Condos: A popular option that combines convenience and style, perfect for those wanting amenities and a home-like atmosphere.
  • Cottages: These delightful and quaint accommodations offer a charming escape for those seeking a cozy retreat.
  • Apartments: A practical choice for solo travellers or couples, providing all the essentials in a compact space.
  • Villas: Luxurious and spacious, villas are perfect for travellers looking for a lavish getaway with stunning views.**

Top attractions in and around Summerland Key

Summerland Key is an ideal destination for outdoor and family vacations, offering beautiful beaches and vibrant natural surroundings. Visitors can enjoy a variety of attractions, such as nearby islands and national parks, perfect for those seeking adventure and relaxation. Activities abound in Summerland Key, making it a fantastic spot to explore the natural beauty of the Florida Keys while enjoying quality time with loved ones.

  • Florida Keys Beaches: Located 12.9km from Summerland Key, this beach offers a laid-back atmosphere with soft sands and crystal-clear waters, perfect for sunbathing and swimming.
  • Upper Sugarloaf Sound: This stunning island within Summerland Key boasts outdoor adventures and picturesque beaches, ideal for kayaking and relaxing in nature.
  • Upper Sugarloaf Key: A charming neighbourhood within Summerland Key, it features a vibrant local scene with shops, dining, and a friendly community vibe.

Things to do recommended for couples

Ready for a romantic getaway in Summerland Key? Experience the thrill of water sports at Pigeon Key, located 29.0km away. Embrace the adventure and outdoor vibes, creating unforgettable memories with your partner amidst stunning scenery.

Things to do recommended for families

Families can explore the beautiful waters of Looe Key National Marine Sanctuary, perfect for snorkeling and spotting vibrant marine life. Additionally, enjoy a leisurely day at the nearby beaches or take a scenic bike ride along the Keys, creating lasting memories together.

Things to do recommended for groups

In Summerland Key, your group can enjoy a round of golf at the Key West Golf Club, shop for unique finds at the Big Pine Key Flea Market, and appreciate art and culture at the Tennessee Williams Fine Art Center, all while soaking up the vibrant local atmosphere.

*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 it's with friends, family, or pets, or if you're seeking extended stays, be sure to prioritize your preferences with the right filters. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Summerland Key with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and much more on Vrbo.
  • Traveling to Summerland Key with young kids: Traveling with little ones can present its own set of challenges. It's important to prioritize their comfort and safety, along with ensuring access to suitable amenities, like a private swimming pool. Additionally, keeping in mind your distance to family-friendly attractions can make your trip even more enjoyable.
  • Taking your pets with you to Summerland Key: For many families, a trip isn’t truly a getaway without their furry companion. If this resonates with you, explore Vrbo listings 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 searching for vacation rentals that offer discounts for month-long stays, 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 amenities like a parking spot, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in Summerland Key

Summerland Key offers a picturesque retreat for those seeking outdoor adventures and family-friendly vacations. With its tropical atmosphere and welcoming community, you’ll find yourself immersed in the beauty of the Lower Florida Keys. Explore the charming Summerland Cove and enjoy the relaxing beaches, perfect for excursions and creating lasting memories. Whether you’re on a budget or seeking a luxurious getaway, this stunning island destination has something for everyone.

  • Cudjoe Key: Nestled near Summerland Key, Cudjoe Key is a charming village characterized by its stunning island landscapes. This destination is perfect for outdoor and family experiences, offering a variety of activities such as beach outings and recreational areas. Visitors can explore local shopping venues and enjoy the beauty of nearby beaches and the unique archipelago. Whether you're relaxing by the shore or indulging in some retail therapy, Cudjoe Key promises a delightful getaway.
  • Little Torch Key: Another picturesque village close to Summerland Key, Little Torch Key is known for its inviting beaches and family-friendly atmosphere. This island haven provides excellent opportunities for outdoor adventures and relaxation. Guests can enjoy various recreational areas and shopping centers, making it a convenient escape for all ages. With its charming beaches and serene environment, Little Torch Key is an ideal spot for creating unforgettable family memories.
  • Sugarloaf Key: Just a short distance from Summerland Key, Sugarloaf Key is a delightful village that showcases the natural beauty of the Florida Keys. This island retreat is a haven for outdoor enthusiasts and families alike, providing ample options for recreation and leisure. Visitors can explore shopping malls and local shops while enjoying the picturesque beaches and remarkable archipelago nearby. Sugarloaf Key is a perfect blend of relaxation and adventure, ensuring a memorable vacation experience.

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 simple

Are you eager to save on your upcoming trip? Being adaptable with your travel dates can really help, as prices tend to vary. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental. We're here to assist you every step of the way.

Vrbo Trips: Planning made easy

Vrbo’s unique Trip Board offers you a dedicated space to plan new adventures, pick up right where you left off, or manage your travel arrangements seamlessly. You can easily access the properties you've saved or booked, now categorized under Potential, Upcoming, or Current Trips. To explore the features of 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)
  • The Kite House (23.3 mi / 37.6 km)
  • Blue Hole (5.1 mi / 8.2 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:

  • Upper Sugarloaf Key (5.2 mi / 8.3 km)
  • Florida Keys Beaches (7.7 mi / 12.4 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)
  • Pigeon Key (18.4 mi / 29.7 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 best area to stay in Summerland Key when booking a vacation rental?
When considering a vacation rental in Summerland Key, the area known as the "Summerland Key Isles" comes highly recommended. This picturesque neighbourhood offers a tranquil atmosphere with stunning waterfront views and easy access to the open waters of the Florida Keys. With a range of properties available, from charming cottages to luxurious villas, visitors can find accommodations that suit various preferences and budgets.

One of the top attractions nearby is the beautiful Looe Key Reef, which is a protected marine sanctuary ideal for snorkelling and diving. The vibrant underwater ecosystem is sure to delight nature enthusiasts and adventure seekers alike. Additionally, the Summerland Key Park provides a lovely space for picnicking and enjoying the natural surroundings, making it a superb spot for families.
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 travelling 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.
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, the area around the picturesque waterfront is ideal, offering stunning views of the turquoise waters and easy access to sandy beaches. Properties along the coastline often feature private docks, making them great for boating enthusiasts, along with spacious outdoor decks for enjoying the mild weather. Many of these homes come equipped with modern amenities such as fully stocked kitchens, air conditioning, and outdoor grills, making them suitable for families or groups looking for a relaxing beach getaway.

Additionally, the vicinity near the Summerland Key Fish Company provides a vibrant atmosphere with local dining options where travellers can savour fresh seafood. The neighbourhood is characterised by its laid-back vibe and proximity to various water activities, including kayaking and paddleboarding. Rentals in this area often include amenities like beach access, private pools, and outdoor seating areas for entertaining or simply taking in the spectacular sunsets.
What is the most popular type of vacation rental accomodation in Summerland Key?
In Summerland Key, vacation houses are the most popular type of rental, with around 450 available throughout the area. These spacious properties often feature multiple bedrooms, fully equipped kitchens, and outdoor patios or decks, providing ample space for families or groups to relax and enjoy their surroundings. Many houses are situated close to the beautiful waterfront, making it easy for guests to engage in activities like boating, fishing, or simply soaking up the sun. Additionally, there are about 52 cottages, offering a more quaint and intimate atmosphere, while around 29 campsites and 18 mobile homes cater to those looking for a more adventurous stay.
Are there any family house rentals in Summerland Key?
In Summerland Key, Florida, families will find an impressive selection of vacation rentals, with around 341 options available throughout the area. This charming locale offers a blend of relaxation and adventure, making it ideal for family getaways. Many properties feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces great for barbecues or enjoying the sunshine.

Visitors can expect amenities such as private pools, game rooms, and easy access to nearby beaches and water activities, ensuring both fun and convenience. The proximity to attractions like the Florida Keys National Marine Sanctuary and John Pennekamp Coral Reef State Park provides opportunities for snorkeling, boating, and exploring the stunning marine life.
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 feature pools and hot tubs, with around 376 options to choose from. This idyllic island location offers a unique blend of relaxation and outdoor adventure, making it a great choice for travellers seeking a tropical getaway.

Many of the properties come with private pools, and some even have hot tubs, great for unwinding after a day spent exploring the beautiful surroundings. Expect amenities such as spacious outdoor decks, fully equipped kitchens for self-catering, and comfortable living areas that make it easy to enjoy time with family and friends.
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. 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, making it an excellent destination for travellers with furry companions. The area features a variety of properties, including charming waterfront homes and spacious villas, often equipped with amenities such as private pools, outdoor grilling areas, and fully stocked kitchens. Many rentals also provide easy access to the stunning Florida Keys' natural beauty, allowing for enjoyable outdoor activities.
Are there any remote work vacation rentals in Summerland Key?
In Summerland Key, Florida, there are numerous remote work vacation rentals available, with around 465 options to choose from. This picturesque location, known for its stunning waterfront views and laid-back atmosphere, is ideal for those looking to combine work and leisure. Many properties offer dedicated workspaces, including desks and comfortable chairs, ensuring a productive environment. You'll also find amenities such as Wi-Fi, laptop workstations, and even some properties featuring computer monitors, making it easy to stay connected while enjoying the tropical surroundings. 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 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, which enable guests to prepare their own meals. Many properties also feature pools, including heated options for year-round enjoyment, creating a superb setting for relaxation. Additional amenities often found in these rentals include microwaves and refrigerators, ensuring that guests have everything they need for a comfortable stay.
When is the best time to visit Summerland Key for a vacation rental?
July marks the peak season for visiting Summerland Key, drawing travellers who are eager to embrace the sun-soaked paradise of the Florida Keys. This month is ideal for those seeking vibrant outdoor activities, from snorkeling in crystal-clear waters to enjoying leisurely beach days under the warm sun. The atmosphere is lively, with visitors indulging in the local cuisine and taking part in various water sports.

During this peak season, temperatures typically hover around the mid to high 30s Celsius, creating the great conditions for water-based adventures and relaxation. The summer months, from July through September, are particularly popular due to the inviting climate and the abundance of marine life, making it a haven for diving enthusiasts and nature lovers alike.

If you're considering a visit when the crowds are thinner and prices more budget-friendly, October is an excellent choice. This month offers a quieter experience, allowing you to explore the natural beauty of the Keys at a more leisurely pace. The weather remains warm, and while you may encounter occasional rain showers, the lush landscapes and fewer tourists make for a truly enjoyable getaway.
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.
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 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 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.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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