Longboat Key holiday lettings

We found 11,714 holiday rentals — enter your dates for availability
Discover a selection of 23 homes, 17 apartments and other holiday rentals in Longboat Key that are perfect for your trip. Whether you're going on holiday with family or friends, holiday rentals have the best amenities for hanging out with the people that matter most, which might include Wi-Fi and a hot tub. No matter what you're looking for, you'll be sure to find a property to rent that has what everyone needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts – Longboat Key

Showing deals for:9 Oct - 16 Oct

Image gallery for Cosy home near Anna Maria Island

Front yard gumbo limbo tree
9.8 out of 10, Exceptional, (92 reviews)
Exceptional
(92 reviews)

Cosy home near Anna Maria Island

Bradenton

7% off
Price is £1,317
for 7 nights, 1 home
£188 per night
includes taxes & fees
Cosy home near Anna Maria Island

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Why visit Longboat Key

  • Stunning Beaches: Longboat Key boasts pristine sandy beaches, perfect for sunbathing and relaxation.
  • Outdoor Activities: Engage in various water sports, including kayaking, paddleboarding, and fishing in the vibrant marine environment.
  • Charming Parks: Explore lovely urban parks offering serene spots for picnics and leisurely strolls amidst nature.
  • Family-Friendly Atmosphere: The tranquil community vibe makes it an ideal destination for family holidays and outings.
  • Delightful Dining: Enjoy a range of dining options featuring fresh seafood and local cuisine to satisfy every palate.

Popular types of accommodation in Longboat Key

Your adventure begins in Longboat Key, Florida, a stunning destination known for its pristine beaches and vibrant marine life. Enjoy spacious accommodations in cosy condos, houses, and apartments that cater to every traveller's needs. Explore the beautiful parks, indulge in water sports, or simply relax by the shore. With transparency, savings, and reassurance, Longboat Key vacation rentals offer the perfect base for an unforgettable getaway.

  • Condos: The top choice for holiday rentals in Longboat Key, offering modern amenities and stunning views.
  • Houses: A popular option, these homes provide privacy and a homely atmosphere for families or groups.
  • Apartments: Ideal for couples or solo travellers, these smaller spaces are conveniently located near attractions.
  • Cottages: Quaint and charming, cottages offer a cosy retreat, often close to the beach.
  • Villas: Luxurious and spacious, villas are perfect for those seeking a premium getaway experience.**

Top attractions in and around Longboat Key

Longboat Key, Florida, is an idyllic destination for beach and family holidays, offering a blend of cultural and outdoor experiences. Visitors can enjoy stunning sandy beaches, explore the marina, and relax in urban parks. With its tranquil atmosphere and beautiful surroundings, Longboat Key provides ample opportunities for unforgettable family outings and beach activities, making it a delightful spot for tourists seeking both relaxation and adventure.

  • Jewfish Key: A tranquil island within Longboat Key, Jewfish Key boasts stunning beaches and a relaxed atmosphere, perfect for sunbathing or leisurely walks. Its natural beauty invites outdoor enthusiasts to explore its serene surroundings.
  • Lido Beach: Renowned for its picturesque shoreline, Lido Beach offers a vibrant beach vibe, ideal for swimming, sunbathing, and beachcombing. The soft sands and gentle waves create a perfect seaside retreat.
  • St. Armands Circle: This charming street features boutique shops and delightful eateries, offering a lively city vibe. It's a great place to enjoy shopping and dining while soaking in the local culture.

Things to do recommended for couples

Longboat Key offers idyllic sunsets on the beach, romantic dinners at waterfront restaurants, and leisurely strolls along the shoreline. Explore the local art scene or indulge in a couple’s massage at a spa for a perfect blend of relaxation and romance.

Things to do recommended for families

Families visiting Longboat Key can enjoy a day at the beautiful beaches, build sandcastles, and take part in water sports. The nearby Mote Marine Laboratory offers engaging exhibits, while the local parks provide space for picnics and nature walks, perfect for creating lasting memories together.

Things to do recommended for groups

Explore the stunning beaches of Longboat Key, indulge in fresh seafood at local restaurants, or embark on a kayaking adventure through the scenic mangroves. For a unique experience, consider a sunset cruise for breathtaking views and memorable moments with your group.

*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 Longboat Key

When travelling with a group, family, or pets, or if you’re seeking extended stays, it’s essential to refine your search according to your specific needs. Here are some helpful Vrbo booking tips for you.

  • Traveling to Longboat Key with a group: Think about how many bedrooms you'll require, as well as additional features like a fully equipped kitchen or outdoor space for group get-togethers. Thankfully, you can easily refine your search for all these options and more on Vrbo.
  • Traveling to Longboat Key with young kids: Traveling with small children can present its own set of challenges. It's important to prioritise their comfort and safety, along with ensuring access to suitable amenities, such as a private swimming pool. Additionally, it’s wise to think about how close you are to attractions that cater to families.
  • Taking your pets with you to Longboat Key: For many, a family holiday wouldn't be the same 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 everyone feels comfortable and at home.
  • Planning for a long term stay visiting Longboat Key: If you're in search of holiday rentals offering discounts for stays of a month or more, you've come to the right place. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include preferences such as a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Longboat Key

Longboat Key, Florida, offers a tranquil beach getaway perfect for family vacations. With its quiet beaches and serene atmosphere, visitors can unwind while soaking up the sun. Explore the picturesque coastline, indulge in water activities, and enjoy delightful dining experiences. The friendly community and charming surroundings make it an ideal destination for those seeking relaxation and family-friendly adventures. Whether you're lounging on the sand or enjoying local attractions, Longboat Key promises a memorable escape.

  • Sarasota: Sarasota is a vibrant city located 14km from Longboat Key, known for its blend of cultural attractions and stunning beaches. Visitors flock to this coastal gem for a family-friendly atmosphere and city-themed experiences. Enjoy a day at the local shopping mall centres or relax at the beach, where you can soak up the sun or engage in water sports. Sarasota’s landmarks include the beautiful family beach and charming town neighbourhoods, making it a perfect destination for those looking to explore both urban and natural settings.
  • Anna Maria Island: Just 11km from Longboat Key, Anna Maria Island is a picturesque haven characterised by its stunning beaches and outdoor activities. This idyllic island is perfect for families seeking a more laid-back experience. With a variety of resorts and recreational areas, you can indulge in water sports, beachcombing, or leisurely strolls along the shoreline. The local attractions include the inviting family beaches and scenic capes, offering a serene environment for relaxation and adventure alike.
  • Bradenton Beach: Located a mere 8km from Longboat Key, Bradenton Beach is another delightful city that offers a wonderful beach and outdoor experience. Families and outdoor enthusiasts will appreciate the numerous recreational areas and shopping mall centres available. The pristine beaches are perfect for sunbathing or swimming, while the charming town neighbourhoods provide a welcoming atmosphere for exploration. With its proximity to Longboat Key, Bradenton Beach serves as an excellent spot for a day trip full of fun and relaxation.

Best time to go to Longboat Key

If you're planning a trip to Longboat 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 October to December tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January62.6°F (17.0°C)Light RainMostly SunnyAverageSlightly Low
February65.5°F (18.6°C)No Rain (Dry)Mostly SunnyAverageAverage
March68.4°F (20.2°C)Light RainMostly SunnyModerately HighSlightly High
April73.8°F (23.2°C)Light RainMostly SunnyModerately HighSlightly High
May78.1°F (25.6°C)Light RainMostly SunnyAverageAverage
June82.0°F (27.8°C)Light RainMostly SunnyAverageAverage
July83.1°F (28.4°C)Moderate RainMostly SunnyModerately HighSlightly High
August83.5°F (28.6°C)Moderate RainMostly SunnyAverageAverage
September81.5°F (27.5°C)Moderate RainMostly SunnyAverageSlightly Low
October77.0°F (25.0°C)Light RainMostly SunnyModerately LowSlightly Low
November70.5°F (21.4°C)Light RainMostly SunnyModerately LowAverage
December66.4°F (19.1°C)Light RainMostly SunnyModerately LowAverage

Booking with Vrbo is simple

Are you hoping to save on your upcoming trip? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, you can enjoy considerable savings by opting for a longer stay. To discover a Vrbo property that suits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo's cutting-edge Trip Board offers you a convenient platform to plan new journeys, pick up from where you last stopped, or review and arrange your travel plans. You can easily locate properties you've saved or booked in the sections for Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Relaxing Longboat Key will entice you

Enjoy the monuments and other features of Longboat Key. This relaxing city is known for its beaches, bird watching and seaside. Lido Beach and Siesta Key Beach are just a couple of the must-see attractions in the area. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in and around Longboat Key

Are you hoping to find things to do during your stay? Venture out of your cosy holiday rental and experience everything that Longboat Key has to offer. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Sarasota Jungle Gardens (7.1 mi / 11.4 km)
  • Mote Marine Laboratory & Aquarium (7.4 mi / 12 km)
  • Premier Sports Campus at Lakewood Ranch (16.9 mi / 27.3 km)
  • Aluna Wellness Center & Spa (5.3 mi / 8.6 km)
  • Harborside Golf Course at Longboat Key Club (6.9 mi / 11.2 km)
  • Islandside Golf Course at Longboat Key Club (7 mi / 11.2 km)

Exploring the beaches and other natural features in Longboat Key

Travellers enjoy Longboat Key for its sunsets and seaside. Whether you're an adventurous traveller or just want to take in the scenery, you'll be sure to find the perfect setting for your holiday in Longboat Key. These are some of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city centre:

  • Lido Beach (8.8 mi / 14.2 km)
  • Siesta Key Beach (12 mi / 19.4 km)
  • Tampa Bay (25.2 mi / 40.6 km)
  • Bean Point Beach (10 mi / 16.1 km)
  • Fort De Soto Park (15.8 mi / 25.4 km)
  • Jewfish Key (2.5 mi / 3.9 km)

Seasonal weather averages in Longboat Key

Travellers enjoy Longboat Key for its boating. If you're hoping to enjoy some warm-weather activities on your holiday, August, July, June and September are the hottest months to visit, when temperatures average 28°C.

How to get to and around Longboat Key

The nearest airport is in Sarasota, FL (SRQ-Sarasota-Bradenton Intl.), located 6.7 mi (10.8 km) from the city centre. If you're unable to find a flight that fits your schedule, you could book a flight to St. Petersburg, FL (SPG-Albert Whitted), which is 24.4 mi (39.2 km) away.

Frequently asked questions

What is the best area to stay in Longboat Key when booking a holiday rental?
Longboat Key is a charming destination that offers several delightful areas for holiday rentals, each with its unique appeal. One of the most popular areas is the northern part of the island, known for its serene atmosphere and stunning beachfront properties. Here, you'll find beautiful stretches of sand and the picturesque views of the Gulf of Mexico, making it ideal for those seeking relaxation and natural beauty.

Another excellent choice is the central region of Longboat Key, which boasts a mix of residential and rental properties. This area is close to the Longboat Key Club, a luxurious resort that offers various amenities, including golf courses and spa services. Additionally, the nearby Bayfront Park provides lovely walking trails and picnic spots, great for enjoying the outdoors.

For those interested in a vibrant setting, the southern end of Longboat Key, near St. Armands Circle, is a fantastic option. This lively area is known for its upscale shopping, dining, and art galleries, providing a more dynamic holiday experience. The Circle is also close to Lido Beach, a popular spot for sunbathing and water sports.

Overall, Longboat Key features a diverse selection of properties across its different neighbourhoods, suiting various preferences and budgets.
How much does it cost to rent a holiday home in Longboat Key?
Prices for holiday rentals in Longboat 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 Longboat 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 Longboat Key holiday house rentals?
You can find great discounts on house rentals in Longboat 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 Longboat Key?
For renting a beach house in Longboat Key, the area along Gulf of Mexico Drive is particularly popular, offering easy access to pristine sandy beaches and stunning sunsets. Many properties in this vicinity feature direct beach access, private pools, and spacious outdoor areas, ideal for families and groups seeking a relaxing retreat. These houses often come equipped with modern kitchens, multiple bedrooms, and amenities such as barbecue grills and outdoor dining spaces, allowing guests to enjoy al fresco meals while soaking in the coastal atmosphere.

The northern end of Longboat Key near the Longboat Key Club is another excellent choice, where you'll find luxurious rentals that often include resort-style amenities like access to golf courses, tennis courts, and full-service spas. Some properties in this area also offer private beach cabanas and concierge services, enhancing the overall holiday experience.

For those looking to explore, the nearby areas of Anna Maria Island and Sarasota provide charming local shops, restaurants, and cultural attractions, making it easy to enjoy both beach relaxation and vibrant community life. Find your rental near the beach in Longboat Key.
What is the most popular type of holiday rental accomodation in Longboat Key?
In Longboat Key, condos are the most popular type of holiday rental, with around 2,248 available throughout the area. These condos are typically located near the beach and offer amenities such as fully equipped kitchens, spacious living areas, and often access to communal pools and fitness centres. Many units also feature private balconies with stunning views of the Gulf of Mexico, great for relaxing after a day in the sun.

For those seeking more space, approximately 660 holiday houses are available, suiting families or larger groups. These homes generally come with multiple bedrooms, private outdoor areas, and sometimes even direct beach access. Additionally, there are around 140 apartments, 56 cottages, and 52 villas, providing a range of options for various preferences and budgets.
Are there any family house rentals in Longboat Key?
In Longboat Key, Florida, there are numerous family-friendly house rentals available, with around 564 options to choose from. This beautiful coastal area is great for families seeking a relaxing getaway. Many homes come equipped with spacious living areas, fully stocked kitchens, and outdoor patios or decks ideal for dining al fresco. Visitors can also enjoy amenities such as private pools, game rooms for entertainment, and easy access to the stunning beaches that the region is known for.

The locale offers a variety of neighbourhoods, each with its unique charm. For those interested in outdoor activities, the proximity to the beach means families can indulge in swimming, sunbathing, and water sports. Additionally, nearby attractions like the Longboat Key Club with its golf course and tennis courts provide ample opportunities for recreation.
Can I rent a holiday home with a pool or hot tub in Longboat Key?
In Longboat Key, there are plenty of holiday homes available for rent that feature pools and hot tubs, with around 682 options to choose from. This beautiful barrier island offers a range of neighbourhoods, including the serene north end, which is superb for those seeking a quieter getaway, and the more vibrant south end, known for its proximity to local shops and dining.

Travellers can expect a variety of amenities in these rentals, such as private pools, relaxing hot tubs, and outdoor living areas ideal for enjoying the warm Florida sunshine. Many properties also come equipped with fully furnished kitchens, spacious living areas, and direct access to the beach, making them superb for families or groups looking to unwind. Find your rental in Longboat Key with a pool or a hot tub.
Can I find long-stay holiday rentals in Longboat Key?
A long-stay holiday rental in Longboat 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 Longboat Key?
In Longboat Key, there are numerous pet-friendly house rentals available, making it a great destination for travellers wishing to bring their furry companions along. Many of these holiday homes are situated close to the beautiful beaches, allowing for easy access to sun-soaked shores and warm waters.

Visitors can expect a range of amenities such as private pools, outdoor patios, and fully equipped kitchens, which make for a comfortable stay. Some properties even feature fenced yards, ensuring a safe space for pets to roam freely.

The area also offers pet-friendly points of interest, including nearby parks where pets can enjoy the outdoors. The Longboat Key Dog Park is a popular spot for local dogs to socialise, providing a fenced area with agility equipment and walking trails. See all pet-friendly rentals in Longboat Key.
Are there any remote work holiday rentals in Longboat Key?
In Longboat Key, Florida, there are numerous remote work holiday rentals available, with around 2,956 options to choose from. This beautiful coastal destination offers a range of properties that cater to remote workers, often featuring amenities such as free Wi-Fi, both in-room and in common areas, ensuring a seamless working experience. Many rentals come equipped with dedicated workspaces, comfortable seating, and peaceful environments that allow for productivity.

The area is known for its stunning beaches and proximity to local attractions, making it an ideal place to balance work and leisure. Visitors can enjoy nearby points of interest like the Longboat Key Club, which offers golfing and spa services, as well as various dining options along the coast. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Longboat Key holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Longboat 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 Longboat Key?
In Longboat Key, popular rental amenities include fully equipped kitchens, onsite parking, and coffee or tea makers for convenience. Many properties also feature decks or patios, as well as balconies, allowing guests to enjoy the beautiful surroundings and pleasant weather.
When is the best time to visit Longboat Key for a holiday rental?
The best time to book a holiday rental in Longboat Key is during the peak season, which typically runs from February to April. This period draws numerous travellers seeking sun-soaked beaches and a relaxing escape, as the weather is wonderfully warm and inviting. With temperatures averaging between 20 to 28 degrees Celsius, visitors can indulge in outdoor activities like swimming, kayaking, and soaking up the sun on pristine sandy shores.

March stands out as the most popular month, attracting families and couples alike, all eager to enjoy the vibrant setting and engaging local events. The beaches come alive, with many opportunities for water sports and leisurely strolls along the coast.

If you're looking for a more economical option, consider visiting in November. This month offers a quieter experience, superb for those who appreciate a tranquil environment and the beauty of the area without the bustling crowds. The weather remains pleasant, allowing for enjoyable outdoor exploration and local dining experiences.

Ultimately, whether you prefer the lively energy of peak season or the calm of the shoulder months, Longboat Key has something to offer every type of traveller.
How early should I book a Longboat Key holiday rental?
Book your Longboat 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.
What are the top attractions in Longboat Key?
In Longboat Key, visitors can enjoy a range of attractions that highlight the area's natural beauty and recreational opportunities. The stunning beaches, such as the pristine Longboat Key Beach, are superb for sunbathing, swimming, and water sports. Many holiday rentals are situated close to these sandy shores, offering easy access to the ocean.

For those interested in nature, the Longboat Key Pass provides excellent opportunities for kayaking and paddleboarding, allowing guests to explore the coastal waters and spot local wildlife. The area is also home to the beautiful Joan M. Durante Community Park, which features scenic walking trails, picnic areas, and a playground, making it ideal for families.

Art enthusiasts might enjoy visiting nearby St. Armands Circle, which boasts an array of boutique shops, galleries, and restaurants, providing a charming atmosphere for leisurely strolls and dining. Furthermore, the proximity to Sarasota allows for additional attractions, such as the Ringling Museum of Art and the vibrant culture of downtown Sarasota.
Can I change or cancel my Longboat Key home rental booking on Vrbo?
To find Longboat 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 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 Longboat 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.
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, 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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