Longboat Key holiday lettings

We found 11,556 holiday rentals — enter your dates for availability

Discover a selection of 24 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:20 Mar - 27 Mar

Image gallery for Private Indoor/Outdoor POOL & Waterfront Oasis on Siesta Key

Pool
10 out of 10, Exceptional, (7 reviews)
Exceptional
(7 reviews)

Private Indoor/Outdoor POOL & Waterfront Oasis on Siesta Key

Siesta Key, FL

8% off
Price is £11,306
for 7 nights, 1 villa
£1,615 per night
includes taxes & fees
Private Indoor/Outdoor POOL & Waterfront Oasis on Siesta Key

Find spaces that suit your style

Why visit Longboat Key

  • Tranquil beaches: Longboat Key boasts serene, sun-kissed shores perfect for relaxation and exploration.
  • Family-friendly atmosphere: The area offers a welcoming environment, ensuring enjoyable experiences for all ages.
  • Variety of accommodations: Choose from charming condos, spacious holiday homes, and luxurious villas to suit your needs.
  • Outdoor activities: Engage in a myriad of outdoor pursuits, from water sports to leisurely beach strolls.
  • Cultural attractions: Discover local marinas and modern educational institutions that enhance your visit.

Popular types of accommodation in Longboat Key

You've set your sights on a getaway to Longboat Key, and now the exciting task of selecting your accommodation begins. Explore the most sought-after options for holiday rentals, from charming condos and spacious private holiday homes to well-appointed apartments. Whether you’re after a luxurious villa or a cosy house rental, Longboat Key has something to suit every traveller's needs, ensuring a memorable stay by the beautiful coast.

  • Condos: The most sought-after accommodation in Longboat Key, offering a blend of luxury and convenience for holidaymakers.
  • Houses: A popular choice for families or groups, providing ample space and a home-like atmosphere.
  • Flats: Ideal for those seeking a comfortable and self-contained stay, these are a preferred option for solo travellers or couples.
  • Cottages: Quaint and charming, perfect for those who desire a more traditional holiday experience.
  • Villas: Luxurious and spacious, these accommodations offer an upscale retreat for discerning visitors.**

Top attractions near Longboat Key

Longboat Key is ideal for a beach holiday, family getaway, or city-themed vacation. Visitors can explore a variety of attractions, including stunning beaches, marinas, and modern educational institutions. The area offers a rich blend of culture and outdoor activities, ensuring a memorable beach experience for all types of travellers. Be sure to take advantage of the local points of interest to make the most of your visit.

  • IMG Academy: A premier sports training facility located 2.5km from Longboat Key, IMG Academy offers a unique opportunity to witness elite athletes in action. Visitors can engage in various sports events, clinics, and tournaments, making it a must-see for sports enthusiasts.
  • Lido Beach: Situated 5.6km away, Lido Beach boasts stunning white sands and vibrant beach vibes. It's perfect for sunbathing, swimming, and enjoying water sports, with picturesque sunsets that create a relaxing atmosphere.
  • St. Armands Circle: Located 5.0km from Longboat Key, this bustling street features an array of shops and restaurants, exuding lively city vibes. It's an excellent spot for leisurely strolls, dining, and indulging in boutique shopping.

Things to do recommended for couples

Seeking a romantic getaway in Longboat Key? Indulge in relaxation at Aluna Wellness Center & Spa, enjoy playful competition at Fish Hole Adventure Golf, or embark on an exciting paddleboarding adventure with AMI Paddleboard Adventures. Each experience promises memorable moments together in this stunning locale.

Things to do recommended for families

Families can enjoy a day out at LECOM Park, just 4.3km from Longboat Key, to soak up the sports atmosphere. Alternatively, the Astro Skate and Fun Center, also 4.3km away, offers thrilling arcade adventures, while the Robert L. Taylor Community Complex, 5.0km distant, promotes wellness and relaxation.

Things to do recommended for groups

Groups visiting Longboat Key can enjoy a cultural evening at the Asolo Theatre, play a round of golf at the nearby Manatee Golf Course, or shop for surf gear at the West Coast Surf Shop, all while soaking in the vibrant local atmosphere.

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

If you're travelling with a group, enjoying a family holiday, bringing along your pets, or seeking extended stays, it's essential to filter your search according to your key priorities. Here are some helpful booking tips for Vrbo.

  • Traveling to Longboat Key with a group: Think about how many bedrooms you require, along with features like a fully equipped kitchen or outdoor areas for group activities. Thankfully, you can easily apply filters for all these options and more on Vrbo.
  • Traveling to Longboat Key with young kids: Travelling with young children can present its challenges. It's essential to prioritise their comfort and safety, along with appropriate facilities like a private swimming pool. Additionally, it’s wise to think about your closeness to family-friendly attractions.
  • Taking your pets with you to Longboat Key: For many families, a getaway wouldn’t be the same without their furry companion. If this resonates with you, take a look at 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 with special offers for stays of a month or more, you’ve come to the right spot. By using the appropriate filter, you can effortlessly discover and save on monthly accommodations. Don’t forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Longboat Key

Longboat Key, Florida, offers a delightful beach getaway with its tranquil, sun-kissed shores and family-friendly atmosphere. Enjoy the serene vibes of quiet beaches, perfect for relaxation and exploration. Nearby cities provide a mix of business and friendly local charm, ensuring that every traveller finds their ideal excursion. With a variety of rentals available, Longboat Key promises a memorable stay for those seeking both adventure and relaxation in a stunning coastal setting.

  • Sarasota: Sarasota is a vibrant city located 5.6km from Longboat Key, offering a delightful blend of beach and urban experiences. Visitors flock to Sarasota for its stunning coastline and family-friendly attractions. Spend your days enjoying the beautiful beaches, shopping in the local malls, or indulging in the resort lifestyle. Notable landmarks include the picturesque family beach and charming neighbourhoods, making it an ideal destination for those seeking both relaxation and entertainment.
  • Anna Maria Island: Just 4.3km from Longboat Key, Anna Maria Island is a charming and tranquil destination that boasts beautiful beaches and outdoor adventures. Perfect for families and nature lovers, this island offers a variety of recreational activities alongside its stunning scenery. Explore the local resorts, unwind in the recreational areas, or enjoy shopping at the nearby malls. With its idyllic beaches and a family-friendly theme park, Anna Maria Island is a perfect spot for a leisurely getaway.
  • Anna Maria: Located 5.6km from Longboat Key, the city of Anna Maria is renowned for its breathtaking scenery and outdoor experiences. This picturesque location invites visitors to revel in its beaches and lush landscapes. Engage in activities at local resorts, enjoy shopping in quaint centres, or explore the recreational areas. With its stunning family beaches and the nearby cape, Anna Maria offers a perfect blend of relaxation and adventure, making it an excellent addition to your vacation itinerary.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
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 keen to save on your upcoming getaway? Being flexible with your travel dates can make a real difference, as prices often fluctuate. Additionally, you might enjoy substantial savings by opting for a longer stay. To discover a Vrbo property that aligns with your budget, simply use our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo's Trip Board offers a user-friendly area for you to plan new journeys, resume your previous arrangements, or keep track of your itineraries. Here, you'll find the properties you've saved or booked neatly organised into categories such as Potential, Upcoming, or Current Trips. To begin exploring 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)
  • Longboat Key Beaches (2.8 mi / 4.6 km)
  • Coquina Beach (3.2 mi / 5.2 km)
  • Cortez Beach (4.2 mi / 6.7 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?
When booking a holiday rental in Longboat Key, Florida, one of the best areas to consider is the northern part of the island, particularly around the neighbourhood of Buttonwood Bay. This serene area offers a peaceful atmosphere, ideal for relaxation, while still being close to stunning beaches and nature. Here, you can enjoy the beautiful Buttonwood Bay Park, which features scenic walking trails and lovely spots for picnicking.

Another excellent option is the southern section of Longboat Key, near the Longboat Key Club, which is known for its luxurious amenities and proximity to the vibrant St. Armands Circle. This area is superb for those who enjoy shopping and dining, as St. Armands offers a charming array of boutiques and restaurants. Additionally, the nearby Lido Beach provides a picturesque setting for sunbathing and water sports.
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, Florida, you should consider the areas along Gulf of Mexico Drive, which runs parallel to the stunning beaches. This stretch offers a variety of holiday rentals, from luxurious beachfront villas to quaint cottages, all with easy access to the sandy shores and picturesque sunsets. Many properties in this area come equipped with modern amenities such as private pools, outdoor dining spaces, and fully equipped kitchens, making them great for families or groups seeking comfort and convenience during their beach getaway.

The northern part of Longboat Key, particularly near the Longboat Key Club, provides additional options for those looking for upscale accommodations. Here, you can find properties that often feature resort-style amenities, including access to golf courses, spas, and fine dining. Rentals in this vicinity typically include spacious living areas, expansive balconies with ocean views, and sometimes even direct beach access. 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 531 options available across the area. These condos are often situated near the beach and provide stunning views of the Gulf of Mexico. Most accommodations come with amenities such as fully equipped kitchens, spacious living areas, and access to communal pools or fitness centres.
Are there any family house rentals in Longboat Key?
In Longboat Key, there are numerous family-friendly holiday rentals available, with around 499 options to choose from. This picturesque barrier island offers a variety of neighbourhoods, each with its own charm and proximity to stunning beaches. Many of these homes feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor patios or balconies where visitors can relax and enjoy the warm Florida weather.

Properties often come with amenities such as private pools, game rooms, and easy access to nearby parks, which are superb for children to play and families to have picnics. The locale is also close to attractions like the Longboat Key Centre for the Arts and the beautiful beaches of the Gulf Coast, ensuring that guests can enjoy both relaxation and 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 639 options to choose from. This beautiful barrier island offers a serene environment, ideal for relaxation. Many properties are located in neighbourhoods like the northern part of the island, which boasts stunning views and easy access to the beach. 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, with around 98 options for travellers seeking to bring their furry companions along. The area is renowned for its beautiful beaches, and many of the holiday homes are within easy reach of the sandy shores, allowing for leisurely strolls with pets.

Expect to find a variety of amenities in these rentals, including private pools, spacious outdoor areas, and fully equipped kitchens, great for families or groups. Many properties also offer features like fenced yards, which can be ideal for pets to roam safely. 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 697 options to choose from. This picturesque location is ideal for those who wish to blend work and leisure, offering stunning views of the Gulf of Mexico and easy access to beautiful beaches. Many properties come equipped with essential remote work amenities, such as high-speed Wi-Fi, dedicated office spaces, and comfortable desks with ergonomic chairs. Additionally, some rentals feature laptop workspaces and computer monitors, suiting various working needs. 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 heated pools, kitchens, and shared pools, suiting the preferences of holidayers seeking both relaxation and convenience. Many holiday rentals feature fully equipped kitchens, allowing guests to prepare their meals and enjoy dining in comfort. Additionally, properties often come with microwaves for quick snacks and meals.
When is the best time to visit Longboat Key for a holiday rental?
The most popular time to visit Longboat Key is from February to April, when the area comes alive with tourists seeking sunshine and relaxation. During this peak season, visitors flock to the pristine beaches, enjoy water sports, and indulge in the vibrant local dining scene. With average temperatures hovering in the mid to high 20s Celsius, it's an ideal time for outdoor activities such as kayaking, paddleboarding, and leisurely beach strolls.

March, in particular, draws many holidaymakers, providing a lively atmosphere filled with events and opportunities to socialise with fellow travellers. The stunning sunsets over the Gulf of Mexico offer a picturesque backdrop for those looking to unwind after a day of adventure.

For those considering a visit during a quieter time, November presents a wonderful opportunity to enjoy the beauty of Longboat Key at a more relaxed pace. This month typically features pleasant temperatures in the low to mid 20s Celsius, allowing for comfortable exploration of the area's natural beauty and local attractions without the hustle and bustle of the peak season.
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.
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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