Photo by throwingsofas

Longboat Key vacation rentals

We found 11,264 vacation rentals — enter your dates for availability

Select from 171 houses, 52 apartments, and other vacation rentals to find the perfect place for your stay in Longboat Key. Whether you're going on vacation with family or friends, vacation rentals have the best amenities for spending time at your vacation home, which might include a garden and hot tub. 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.

Vacation rentals with weekly discounts - Longboat Key

Showing deals for:Dec 26 - Jan 2

Image gallery for Ila's Beach House: Near IMG-Heated Salt Pool- Pets OK-Modern Organic Smart Home

Pool
9.8 out of 10, Exceptional, (36 reviews)
Exceptional
(36 reviews)

Ila's Beach House: Near IMG-Heated Salt Pool- Pets OK-Modern Organic Smart Home

Bradenton, FL

8% off
Price is $397
$2,779 for 7 nights
All fees included
Ila's Beach House: Near IMG-Heated Salt Pool- Pets OK-Modern Organic Smart Home

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more

  • More for less

    More space, more privacy, more amenities — more value

  • A place for everyone

    We stand for diversity, inclusion and families everywhere.
    Learn more

Find out more about Longboat Key

Find out more about Longboat Key

Why visit Longboat Key

  • Beautiful Beaches: Longboat Key is renowned for its serene, picturesque beaches, perfect for relaxation and sunbathing.
  • Family-Friendly Atmosphere: The area offers a welcoming environment with activities suitable for families and children.
  • Luxurious Accommodations: Enjoy a stay at upscale resorts, condos, and vacation homes that cater to various preferences.
  • Outdoor Activities: Engage in water sports, fishing, and exploring local marinas, enhancing your adventure experience.
  • Charming Neighborhoods: Discover friendly local spots that provide budget-conscious excursions and unique cultural experiences.

Popular types of accommodation in Longboat Key

If you're exploring vacation rentals in Longboat Key, you've come to the right place. The most popular types of accommodations include condos, houses, and apartments. Whether you're interested in a cozy condo rental in Longboat Key or a spacious vacation home, we have options to suit every traveler. Don't forget to check out our Lido Key rentals and the exclusive Longboat Key Club for a luxurious experience. Your perfect getaway awaits.

  • Condos: The top choice for vacation rentals in Longboat Key, offering stunning views and convenient amenities for an enjoyable stay.
  • Houses: A popular option for families and groups, providing spacious accommodations and a home-like atmosphere.
  • Apartments: Ideal for solo travelers or couples, these rentals offer comfort and a central location.
  • Cottages: Quaint and charming, cottages provide a cozy retreat close to the beach.
  • Villas: An upscale choice, villas offer luxury and privacy for a relaxing getaway.**

Top attractions near Longboat Key

Longboat Key, Florida, is an ideal destination for beach lovers and families alike, offering a mix of culture, outdoor activities, and stunning beach experiences. Key attractions include beautiful beaches, modern universities, and marinas, perfect for exploring the area's vibrant atmosphere. Whether you’re looking to relax on the beach or discover local points of interest, Longboat Key has something to offer for every type of traveler.

  • IMG Academy: A premier sports training facility known for its elite athletic programs and state-of-the-art facilities. Visitors can experience the vibrant atmosphere of aspiring athletes and possibly catch a game or training session.
  • Lido Beach: A beautiful, sun-soaked beach renowned for its soft white sands and clear waters. Ideal for relaxation, swimming, and beach activities, it offers a quintessential Florida beach vibe.
  • St. Armands Circle: A lively shopping and dining district featuring upscale boutiques and diverse eateries. The bustling atmosphere and charming architecture create a perfect spot for leisurely strolls and people-watching.

Things to do recommended for couples

Looking for a romantic getaway in Longboat Key? Indulge in relaxation at Aluna Wellness Center & Spa, enjoy a fun round at Fish Hole Adventure Golf, or get adventurous with H2O Watersportz. Each experience offers a unique way to connect and create lasting memories together.

Things to do recommended for families

Families visiting Longboat Key can enjoy a day of sports at LECOM Park, unleash their adventurous side at the Astro Skate and Fun Center, and relax at the Robert L. Taylor Community Complex, offering wellness activities for all ages, all conveniently located within a short drive.

Things to do recommended for groups

Groups visiting Longboat Key can enjoy a captivating performance at the Asolo Theatre for the Performing Arts, dive into adventure at the Longboat Key Public Tennis Center, and explore the vibrant shops and dining options at Bridge Street, all while soaking up the local culture and family-friendly 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 Longboat Key

When you're planning a trip, whether it's with a group, family, pets, or for an extended stay, be sure to use the appropriate filters to match your priorities. Here are some helpful booking tips for Vrbo.

  • Traveling to Longboat Key with a group: Think about how many bedrooms you require, as well as features like a complete kitchen or outdoor area for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Longboat Key with young kids: Traveling with young kids can be a bit tricky. It's important to prioritize their comfort and safety, along with finding suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Longboat Key: For many families, a vacation wouldn’t be the same without their furry companion. If you can relate, explore Vrbo listings that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and beds, ensuring that all members of your family feel comfortable and at home.
  • Planning for a long term stay visiting Longboat Key: If you're seeking vacation rentals that offer discounts for month-long stays, you've come to the perfect spot. By using the appropriate filters, you can easily discover and save on monthly rentals. Don't forget to include features like 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, is a stunning vacation destination known for its beautiful, quiet beaches and family-friendly atmosphere. Visitors can unwind at luxurious resorts while enjoying the relaxed island vibe. Explore nearby neighborhoods that offer a friendly, budget-conscious experience, perfect for excursions and family activities. With its blend of natural beauty and welcoming surroundings, Longboat Key promises a memorable getaway filled with tranquility and adventure.

  • Sarasota: Located 9 miles away from Longboat Key, Sarasota is a vibrant city renowned for its beautiful beaches and family-friendly atmosphere. Visitors can indulge in a variety of activities such as shopping at local malls, savoring delicious cuisine at diverse restaurants, or relaxing at luxurious resorts. The area is home to stunning coastal landmarks and attractions, including family beaches and charming town neighborhoods that invite exploration. Sarasota's cultural scene is also noteworthy, making it a perfect blend of beach and city experiences.
  • Anna Maria Island: Just 7 miles from Longboat Key, Anna Maria Island is a picturesque destination that offers a quintessential beach getaway. The island is celebrated for its outdoor activities and family-friendly experiences, making it an ideal spot for relaxation and fun. Visitors can enjoy recreational areas, explore the charming local shops, and unwind at serene resorts. With its stunning sandy beaches and proximity to a theme park, Anna Maria Island provides the perfect backdrop for making lasting memories with loved ones.
  • Anna Maria: Situated 9 miles from Longboat Key, Anna Maria is a quaint city that captures the essence of beachside living. Known for its scenic views and vibrant outdoor spaces, this area is perfect for travelers seeking a laid-back atmosphere. Visitors can explore local resorts, shop at nearby malls, or enjoy recreational activities that take full advantage of the beautiful coastal landscape. With family-friendly beaches and breathtaking capes nearby, Anna Maria offers an unforgettable escape for nature lovers and beach enthusiasts alike.

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

Looking to save on your next vacation? Consider being flexible with your travel dates, as prices can fluctuate. Also, extending your stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, take advantage of our filters to search by price, location, and type of vacation rental.

Save more with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on your reservation. Being the planner has its perks. When you join our travel rewards program, One Key, you'll gain immediate access to member discounts and the opportunity to earn and redeem OneKeyCash on eligible bookings. Sign up today and begin enjoying your savings.

Vrbo Trips: Planning as easy as it gets

Vrbo's cutting-edge Trip Board offers you a convenient way to plan your trips, pick up right where you left off, and keep your travel plans organized. You can easily find the properties you’ve saved and booked under Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Experience Longboat Key at vacation home rentals

Vacation treasures are just waiting to be unwrapped on this beach-lined ribbon of land in the Gulf of Mexico west of Bradenton and Sarasota. Known as a great location to pull out your fishing pole, Longboat Key also offers elegant resorts and upscale dining, plus opportunities to see nature up close and personal. It's only 30 minutes away from Bradenton-Sarasota airport, and just as easy to reach the cultural and family-friendly attractions in both communities. A Longboat Key vacation rental is a relaxing place to warm your heart on a midwinter getaway.

Tourist attractions near Longboat Key vacation homes

A Longboat Key vacation rental is a convenient launching place to visit attractions around the area. Mote Marine Aquarium, just over the bridge to the south, has an open-water Shark Zone and exhibits on alligators, sting rays, manatees, sea turtles, and other aquatic life. South Florida Museum in Bradenton features a manatee aquarium and planetarium, plus exhibits on natural and cultural history. In Sarasota, visit the vast collection of the Ringling Museum of Art, plus the Marietta Museum of Art & Whimsy. Sarasota also offers botanical gardens and encounters of the retail kind.

Activities near your Longboat Key summer rental

If you're looking for sport fishing, Longboat Key is the place. Tarpon and cobia can be caught from the beach, and some docks are lighted for nighttime fishing. Redfish and speckled trout lurk in the mangroves. You can book a charter for offshore fishing—or a cruise just to view the dolphins. Gulf-side beaches beg you to loll in the sun, swim, take up windsurfing or parasailing, and rent paddle boards and boogie boards. There's a public tennis center. Beer Can Island is a boat-in stretch of beach for picnicking at the key's northern tip.

Climate for your trip to Longboat Key vacation rentals

Sunshine rules for 256 days a year on Longboat Key, making outdoor activities enjoyable all year from a Longboat Key vacation rental. Summer is the hottest season, and often humid, with July highs around 90. It's also the wettest, with August rainfall around 9 inches. January high temperatures are generally in the 80s, with the average low around 50. May to late fall is actually the slower season, with lower prices. The cooler, busier winter season is when visitors seek escape from cold and snow elsewhere. Spring and fall are in-between, for both weather and crowds.

Good things in a small package on Longboat Key

Longboat Key occupies a narrow barrier island between the Gulf of Mexico and Sarasota Bay. Everything is packed into 4 square miles of dry land, and you could bike the 10 miles from northerly Beer Can Island to Quick Point in about 50 minutes. Sea turtles and shorebirds nest along the Gulf beaches from April to November, but habitats are protected by keeping observers at a distance and outdoor lights off at night. Crabs and conchs, egrets, herons, and osprey are seen from trails and boardwalks through 34 acres of wetland and mangrove lagoons at Quick Point Nature Preserve.

How to get to and around Longboat Key

The nearest airport is in Sarasota-Bradenton Intl. Airport (SRQ), located 6.7 mi (10.8 km) from the city center. If you can't find a flight that works for your travel itinerary, you could book a flight to St. Petersburg, FL (SPG-Albert Whitted), which is 24.4 mi (39.2 km) away.

Romantic vacation rentals in Longboat Key

If you're looking for a romantic retreat, Longboat Key has an array of tranquil locations to explore. Vacation rentals are available near places like St. Armands Key, a bay island with serene tropical surrounds and parklands, and Leffis Key, an island nature reserve and tidal habitat with nature trails and boardwalks through the marshland. You could also visit Palma Sola Botanical Park, a landscaped garden with exotic plants and lakes.

Frequently asked questions

What is the best area to stay in Longboat Key when booking a vacation rental?
When considering a vacation rental in Longboat Key, Florida, the best areas to stay include the northern part of the island, particularly around Longboat Key Village, and the southern end near the private community of Bay Isles.

Longboat Key Village offers a charming, laid-back atmosphere with a variety of shops, restaurants, and easy access to the beach. This area is known for its beautiful shoreline and proximity to attractions like the Longboat Key Center for the Arts, which hosts various cultural events and showcases local artists. The village has a good number of vacation rental properties, making it a popular choice for visitors looking for convenience and a vibrant local scene.

On the southern end, Bay Isles provides a more exclusive and tranquil experience, featuring stunning waterfront views and beautifully landscaped properties. This area is close to the Longboat Key Club, a premier resort that offers golfing, tennis, and spa services. The serene environment is ideal for those seeking relaxation and a touch of luxury, with plenty of vacation rentals available that cater to families and couples alike.

Overall, both areas offer great experiences, with plenty of vacation rental options, each providing easy access to the island's beautiful beaches and recreational activities.
How much does it cost to rent a vacation home in Longboat Key?
Prices for vacation 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 vacation 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, the area along the Gulf of Mexico offers stunning options. The northern part of Longboat Key, near the Longboat Key Club and the beautiful beaches of the Gulfside, features a variety of vacation rentals. Many of these properties come with amenities such as private pools, direct beach access, and expansive outdoor decks that are superb for enjoying the warm Florida sun.

As you move south towards the area near the historic Longboat Key Village, travelers can find more intimate beach houses. This area often boasts charming cottages and bungalows with kayaks and bicycles available for guest use. Many rentals here include well-equipped kitchens and laundry facilities, enhancing convenience for longer stays. The proximity to local shops, restaurants, and marina access adds to the appeal, allowing visitors to explore the local culture and cuisine.

Additionally, the southern beaches of Longboat Key near the New Pass are ideal for those seeking a quieter atmosphere. Properties in this area tend to be more secluded and may offer amenities such as private docks, outdoor grills, and lush gardens, providing a serene environment for relaxation. Find your rental near the beach in Longboat Key.
What is the most popular type of vacation rental accomodation in Longboat Key?
In Longboat Key, condos are the most prevalent vacation rental choice, with approximately 541 available across the island. These condos are often located near the beach, providing easy access to the stunning Gulf of Mexico. Travelers can expect well-appointed rooms featuring modern amenities such as fully equipped kitchens, spacious living areas, and private balconies or patios that offer beautiful views of the water.

For those seeking more space, there are around 158 vacation houses that cater to families or larger groups. These properties typically come with multiple bedrooms, outdoor spaces, and sometimes private pools, making them ideal for gatherings and relaxation. Additionally, there are smaller options like apartments (around 40), cottages (16), and villas (14), each providing a unique charm and varying levels of privacy and amenities.
Are there any family house rentals in Longboat Key?
In Longboat Key, Florida, families will find a lot of vacation rentals—over 500 options available throughout the area. This beautiful locale is renowned for its stunning beaches and tranquil atmosphere, making it an ideal spot for family getaways. Many properties offer spacious layouts with multiple bedrooms, providing ample room for everyone to relax.

Visitors can expect amenities such as fully equipped kitchens for preparing meals, private outdoor spaces for barbecues and play, and often easy access to the beach, where children can enjoy building sandcastles or swimming. Some homes may also feature pools, game rooms, or activities like beach equipment for added fun.

The area is not just about relaxation; families can explore nearby attractions, including the beautiful Marie Selby Botanical Gardens and the vibrant city of Sarasota, which is just a short drive away and offers additional entertainment options. See all family-friendly rentals in Longboat Key.
Can I rent a vacation home with a pool or hot tub in Longboat Key?
In Longboat Key, there are plenty of vacation homes available for rent that feature pools and hot tubs, with around 637 options to choose from. This picturesque barrier island along Florida's Gulf Coast offers a variety of neighborhoods where these properties can be found, including the serene areas near the beach and the more secluded spots tucked away from the hustle and bustle.

Travelers can expect a variety of amenities in these rentals, including private pools, relaxing hot tubs, spacious outdoor patios, and fully equipped kitchens, ideal for both entertaining and unwinding. Many properties also offer features such as outdoor dining areas, lush tropical landscaping, and direct access to the beach, making it an excellent choice for a refreshing getaway. Find your rental in Longboat Key with a pool or a hot tub.
Can I find long-stay vacation rentals in Longboat Key?
A long-stay vacation rental in Longboat Key is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Longboat Key?
In Longboat Key, there are numerous pet-friendly house rentals available, boasting around 105 options for travelers. This picturesque island offers vacation homes that often come with appealing amenities such as private pools, outdoor dining areas, and fully equipped kitchens, superb for families or groups looking to enjoy a beach getaway with their furry companions.

The area is known for its beautiful beaches, and many rentals are conveniently located just a short walk from the shoreline, allowing for easy access to sun-soaked days by the water. Additionally, Longboat Key is home to several parks, including the well-known Joan M. See all pet-friendly rentals in Longboat Key.
Are there any remote work vacation rentals in Longboat Key?
In Longboat Key, Florida, there are plenty of remote work vacation rentals available, with around 701 options to choose from. This picturesque island offers a serene environment that is ideal for productivity, with many properties featuring dedicated office spaces, desks, and comfortable chairs to ensure a conducive work atmosphere. Expect amenities like high-speed Wi-Fi and laptop workspaces, making it easy to stay connected while enjoying your stay.

The area is known for its beautiful beaches, offering opportunities for relaxation after a day of work. Nearby points of interest include the scenic Longboat Key Club, which provides various recreational activities, and the vibrant St. Armands Circle, known for its shopping and dining options. Many rentals also include outdoor spaces such as balconies or patios, superb for unwinding with a view of the Gulf. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Longboat Key vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Longboat Key with parking available—perfect for families or travelers 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 vacation rental amenities include WiFi, kitchens, and access to heated pools. Many rentals also feature shared pools, allowing guests to enjoy a relaxing swim after a day at the beach. The availability of these amenities makes Longboat Key a favored destination for travelers seeking comfort and convenience during their stay.
When is the best time to visit Longboat Key for a vacation rental?
The best time to visit Longboat Key for a vacation rental is during the peak season from February to April, with March being particularly popular. This time of year attracts travelers seeking warmth and relaxation, as the weather is pleasantly warm, with daytime temperatures typically ranging from the mid-60s to high 70s Fahrenheit. It's the superb opportunity to enjoy outdoor activities such as beach lounging, kayaking, and exploring the scenic coastline.

During these months, you can expect a vibrant atmosphere filled with fellow vacationers enjoying the beautiful beaches and various local events. The area's natural beauty is complemented by a variety of dining options and cultural attractions, ensuring a well-rounded experience for those who appreciate quality and convenience in their travels.

If you're looking for a more budget-friendly option, consider planning your visit in November. This month offers a quieter experience, allowing you to relish the serene beaches and pleasant weather without the crowds.
How early should I book a Longboat Key vacation rental?
Book your Longboat 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.
What are the top attractions in Longboat Key?
In Longboat Key, visitors can enjoy a variety of attractions that highlight the area's natural beauty and leisure opportunities. The stunning beaches, such as those along Gulf of Mexico Drive, are great for sunbathing, swimming, and water sports. Nearby, the Longboat Key Club offers golf and tennis facilities for sports enthusiasts.

For those interested in the arts, the Ringling Museum of Art, located just a short drive away in Sarasota, showcases impressive collections and beautiful gardens. The nearby Mote Marine Laboratory & Aquarium provides an engaging experience for families, featuring marine life exhibits and touch tanks.
Can I change or cancel my Longboat Key home rental booking on Vrbo?
To find Longboat 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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy 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 Longboat 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.

More Vacation Ideas

More Vacation Ideas