Summerland Key holiday lettings

We found 733 holiday rentals — enter your dates for availability

Select from 483 homes, 55 cottages and other holiday rentals in Summerland Key to find one that's perfect for your trip. Whether you're travelling with family, friends or just your furry companion, holiday rentals have the amenities that you expect for your stay, which might include Wi-Fi and a hot tub. Whatever you're looking for, you'll be able to choose a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts - Summerland Key

Showing deals for:12 Dec - 19 Dec

Image gallery for Newly renovated cozy and spacious beach house with breathtaking ocean front

Dock at night
9.8 out of 10 rating
Exceptional
(12 reviews)

Newly renovated cozy and spacious beach house with breathtaking ocean front

Big Pine Key, FL

7% off
Price is £4,254
for 7 nights, 1 home
£608 per night
includes taxes & fees
Newly renovated cozy and spacious beach house with breathtaking ocean front

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Find out more about Summerland Key

Find out more about Summerland Key

Why visit Summerland Key

  • Stunning beaches: Enjoy the beautiful sandy shores perfect for sunbathing and swimming.
  • Outdoor activities: Engage in various adventures such as snorkelling, kayaking, and fishing in the crystal-clear waters.
  • Local charm: Experience the friendly atmosphere and welcoming locals that make Summerland Key unique.
  • Budget-friendly accommodation: Choose from a range of holiday rentals including cottages and condos that cater to all budgets.
  • Natural beauty: Explore nearby national parks and islands offering breathtaking landscapes and wildlife.

Popular types of accommodation in Summerland Key

Explore a variety of holiday rentals in Summerland Key, including houses, cosy cottages, and modern condos. Whether you're travelling with family or friends, our selection of vacation rentals caters to every need. Enjoy the sun-soaked beaches and vibrant local culture while saving money and gaining peace of mind with our transparent booking process. Discover the perfect home away from home for your next getaway in Summerland Key.

  • Houses: The top choice for visitors to Summerland Key, these homes offer spacious and comfortable retreats for families or groups.
  • Condos: A popular option for those seeking a blend of convenience and amenities, providing a home-like atmosphere with resort-style facilities.
  • Cottages: Ideal for a charming and quaint experience, these delightful abodes are perfect for a romantic getaway or a peaceful escape.
  • Apartments: A practical choice for shorter stays, offering the essentials for a comfortable visit in a more urban setting.
  • Villas: Luxurious and spacious, these properties are perfect for an indulgent holiday experience in Summerland Key.**

Top attractions in and around Summerland Key

Summerland Key is ideal for outdoor and family beach holidays, offering a range of attractions including beaches, islands, and national parks. Visitors can enjoy a variety of outdoor activities and adventure experiences, with highlights such as Paradise Summerland Key and popular local attractions. Whether you're seeking friendly activities or simply wish to bask in the natural beauty, Summerland Key provides an unforgettable holiday experience for everyone.

  • Florida Keys Beaches: Located 5.0km from Summerland Key, this beach offers a quintessential tropical experience with golden sands and vibrant beach vibes, perfect for relaxation and sunbathing.
  • Upper Sugarloaf Key: Nestled within Summerland Key, this charming neighbourhood boasts a friendly community atmosphere and city vibes, making it ideal for exploring local shops and culture.
  • Upper Sugarloaf Sound: This picturesque island features stunning outdoor settings and beach vibes, inviting visitors to enjoy kayaking, fishing, and breathtaking sunsets.

Things to do recommended for couples

For a romantic getaway in Summerland Key, explore the thrilling water sports at Pigeon Key, situated 11.2km away. Enjoy adventurous activities together while soaking up the stunning outdoor atmosphere, making unforgettable memories as a couple amidst the beautiful Florida Keys.

Things to do recommended for families

Families visiting Summerland Key can experience the thrill of snorkelling at the nearby John Pennekamp Coral Reef State Park, explore the delightful wildlife at the Dolphin Research Center, and enjoy a sunny day at the beautiful beaches perfect for building sandcastles and relaxing together.

Things to do recommended for groups

Explore the Big Pine Key Flea Market for a taste of local culture, only 3.1km from Summerland Key. Enjoy a round of golf at the Key West Golf Club, 12.4km away, or immerse yourselves in the arts at the Tennessee Williams Fine Art Center, also 12.4km distant.

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

If you’re travelling with a group, family, pets, or planning an extended stay, it’s important to apply the right filters to meet your needs. Here are some helpful Vrbo booking tips for you.

  • Traveling to Summerland Key with a group: Think about the number of bedrooms you'll require, as well as amenities like a fully-equipped kitchen or outdoor space for group gatherings. Thankfully, you can easily apply filters for all of these features, and more, on Vrbo.
  • Traveling to Summerland Key with young kids: Travelling with young children can present its own set of challenges. It's important to prioritise their comfort and safety, alongside ensuring access to suitable amenities like a private swimming pool. Additionally, it's wise to think about your closeness to attractions that are suitable for families.
  • Taking your pets with you to Summerland Key: For many, a family holiday isn’t truly complete without their four-legged companion. If this resonates with you, consider exploring Vrbo properties 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 in search of holiday rentals that offer discounts for stays of a month or more, you’ve come to the perfect destination. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include features such as a parking space, a well-equipped kitchen, or even a private pool in your search criteria.

Where to stay in Summerland Key

Summerland Key, a picturesque island city in the Florida Keys, offers an idyllic setting for outdoor family vacations. With its stunning sandy beaches and a welcoming atmosphere, visitors can indulge in tropical excursions and enjoy a laid-back vibe. Explore nearby attractions and discover the charm of this region, where friendly locals and budget-friendly options make for a memorable getaway. Your next vacation in the tropical keys promises relaxation and adventure in equal measure.

  • Cudjoe Key: Cudjoe Key is a charming village nestled within the Florida Keys, located just a short distance from Summerland Key. This scenic island destination is a haven for outdoor enthusiasts and families, offering a tranquil beach experience. Visitors can indulge in various activities, from exploring the local recreational areas to enjoying shopping at nearby centres. The island's picturesque beaches and stunning archipelago views are perfect for leisurely days spent soaking up the sun or engaging in water sports.
  • Sugarloaf Key: Sugarloaf Key is a delightful village that boasts the same idyllic island charm found throughout the Florida Keys. Situated conveniently near Summerland Key, it attracts visitors seeking outdoor adventures and family-friendly activities. The local shopping areas and recreational venues provide ample opportunities for exploration and enjoyment. The Key’s beautiful beaches and surrounding islands are ideal for families looking to relax or partake in exciting water activities, making it a memorable stop on your vacation.
  • Little Torch Key: Little Torch Key is a picturesque village that offers visitors an authentic island experience, located in close proximity to Summerland Key. Known for its family-friendly atmosphere, this island is perfect for outdoor activities and beach relaxation. The local recreational areas and shopping centres ensure that guests have everything they need for a fun-filled day. With its stunning beaches and inviting family beach spots, Little Torch Key provides a delightful escape into the natural beauty of the Florida Keys.

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

Looking to save on your next holiday? Consider being flexible with your travel dates, as prices can fluctuate. Moreover, opting for a longer stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, utilise our filters to search by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board offers a handy platform for organising your travel plans, allowing you to create new trips, resume from where you last stopped, or review your existing arrangements. You can easily access and sort your saved or booked properties under the categories of Potential, Upcoming, or Current Trips. To begin using Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Book a holiday rental for your Summerland Key getaway

Learn about the unique charm of Summerland Key with a stay in a holiday home rental. This city has something for everyone. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday 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

Do you want to discover top things to see and do in the area? Venture out of your holiday home and experience everything that Summerland Key has to offer. These are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • 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 adventurous traveller or just want to appreciate the scenery, Summerland Key is a great place to get outside. These are some of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

  • 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)
  • Pigeon Key (18.4 mi / 29.7 km)

Transport options to and around Summerland Key

The nearest airport is in Key West, FL (EYW-Key West Intl.), located 20.9 mi (33.6 km) from the city centre. If you can't find a flight that's convenient for your trip, you can 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 holiday rental?
When considering a holiday rental in Summerland Key, the neighbourhood of Summerland Cove is an excellent choice. This area offers a serene and picturesque setting, great for those looking to unwind amidst natural beauty. With its stunning waterfront views and easy access to the ocean, it is ideal for water sports enthusiasts and offers plentiful opportunities for boating and fishing.

One of the top attractions nearby is the beautiful Looe Key National Marine Sanctuary, which is renowned for its vibrant coral reefs and diverse marine life, making it a fantastic spot for snorkelling and diving. Additionally, the nearby National Key Deer Refuge provides a unique opportunity to see the endangered Key deer in their natural habitat, offering delightful walking trails and scenic vistas.
How much does it cost to rent a holiday home in Summerland Key?
Prices for holiday 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 holiday 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, the area along the coastline offers stunning waterfront properties with direct access to the crystal-clear waters of the Florida Keys. The neighbourhoods near the Summerland Key Marina are particularly appealing, where you can find a variety of holiday rentals that come equipped with boat docks, making it ideal for those looking to engage in water activities such as fishing and boating. Many homes in this area feature amenities like spacious outdoor decks, private swimming pools, and modern kitchens, superb for enjoying the sunny Florida climate and entertaining family or friends.
What is the most popular type of holiday rental accomodation in Summerland Key?
In Summerland Key, holiday houses are the predominant type of rental accommodation, with around 450 available throughout the area. These properties often feature spacious layouts, multiple bedrooms, fully equipped kitchens, and outdoor spaces such as decks or patios for enjoying the beautiful Florida weather. Many holiday houses are situated near the waterfront, offering easy access to activities like fishing, boating, and snorkelling.
Are there any family house rentals in Summerland Key?
In Summerland Key, there are numerous family-friendly house rentals available, with around 341 options scattered throughout the area. This charming locale offers a variety of accommodations superb for families looking to enjoy the beautiful Florida Keys. Many of these homes come equipped with spacious living areas, full kitchens for preparing meals together, and outdoor spaces where children can play and explore.

The neighbourhoods in Summerland Key are known for their proximity to the water, making it easy for visitors to partake in activities such as fishing, kayaking, and snorkelling. Families can also find properties featuring amenities like private pools, game rooms, and easy access to nearby parks and beaches, superb for a fun-filled day under the sun.
Can I rent a holiday home with a pool or hot tub in Summerland Key?
In Summerland Key, there are plenty of holiday homes available for rent that feature pools and hot tubs, with around 376 options to choose from. This picturesque island community in the Florida Keys offers a relaxed atmosphere, superb for those looking to unwind by the water. Many properties come equipped with private pools, hot tubs, and spacious outdoor areas, allowing guests to enjoy the warm weather and stunning views of the surrounding waters.
Can I find long-stay holiday rentals in Summerland Key?
A long-stay holiday 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, providing a fantastic opportunity for travellers looking to enjoy a beachside getaway with their furry companions. The area is known for its stunning waterfront views and laid-back atmosphere, making it an ideal destination for families and groups. Many of the holiday rentals come equipped with modern amenities such as private pools, outdoor grills, and fully stocked kitchens, ensuring a comfortable stay.
Are there any remote work holiday rentals in Summerland Key?
In Summerland Key, Florida, there are numerous remote work holiday rentals available, with around 465 properties that cater to those seeking a conducive work environment. Travellers can expect a range of amenities designed for remote working, including reliable Wi-Fi, dedicated office spaces, ergonomic desks, and comfortable chairs. Many properties also feature additional conveniences such as safe storage for valuables and computer monitors, allowing for an efficient workspace away from home. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Summerland Key holiday rentals with parking?
Vrbo offers a wide selection of holiday 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 holiday rental?
The peak season for visiting Summerland Key is during the summer months from July to September, when the island comes alive with vibrant energy and an array of activities. This is an ideal time for travellers who seek sun-soaked days and opportunities for outdoor adventures such as snorkelling, diving, and kayaking in the crystal-clear waters of the Florida Keys.

July, in particular, stands out as the most popular month, with visitors flocking to enjoy the warm temperatures averaging around 30°C. The lively atmosphere is complemented by local events and festivities, making it a great time to connect with fellow travellers and immerse yourself in the island's unique culture.

If you're looking for a more budget-friendly time to visit, consider planning your trip in October. This month often features lower rental rates and a quieter experience, allowing you to relish the natural beauty of Summerland Key without the summer crowds. The weather remains pleasantly warm, and you'll still have opportunities for sightseeing and enjoying the stunning sunsets.
How early should I book a Summerland Key holiday rental?
Book your Summerland Key holiday 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 holiday 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 holiday 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 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 holiday 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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