Longboat Key vacation rentals

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Popular amenities for Longboat Key vacation rentals

Stay near Longboat Key's top sights

IMG Academy36 locals recommend
Mote Marine Laboratory & Aquarium532 locals recommend
Lido Key Beach442 locals recommend
St Armands Circle Shops358 locals recommend
Saint Armands Circle297 locals recommend
Lido Key132 locals recommend

Quick stats about vacation rentals in Longboat Key

  • Total rentals

    780 properties

  • Nightly prices starting at

    $30 before taxes and fees

  • Total number of reviews

    9K reviews

  • Family-friendly rentals

    580 properties are a good fit for families

  • Pet-friendly rentals

    140 properties allow pets

  • Rentals with a pool

    640 properties have a pool

Your guide to Longboat Key

All About Longboat Key

Stretching between the Gulf of Mexico and Sarasota Bay, the barrier island of Longboat Key has attracted its share of sun-seekers, who can be found teeing off at the sweeping gulf-front golf courses or fishing in the mangroves for speckled trout. With Siesta Key to the south and Anna Maria Island to the north, Longboat Key has an upscale feel, with nice restaurants, luxury resorts, and 256 days of annual sunshine. At the northern tip is Beer Can Island, a popular picnic spot that’s prettier than its name might suggest; the untouched, white-sand beach is even accessible on foot at low tide. Paddleboarding, windsurfing, and other on-the-water activities beckon you into the Gulf. And when you’ve finally kicked the sand from your toes and are ready for some culture, you can visit the Ringling Museum of Art in Sarasota, which showcases the circus impresario’s vast collection of classic and modern European and American artworks.

The best time to stay in a vacation rental in Longboat Key

There’s a saying that the local visitors’ bureau likes to use: It’s always summer in Sarasota County. Longboat Key gets its best weather in the fall, winter, and spring, when temperatures stay in the 70s Fahrenheit and Gulf breezes keep things comfortable. These summer-like seasons are preferable to actual summers, which can be rainy and hot, with temperatures in the 90s, not to mention humid and buggy. No matter when you visit, bring your swimsuit: The water is swimmable all year round, and rarely drops below 68 degrees.

Top things to do in Longboat Key

St Armands Circle

This round little island shopping center just south of Longboat Key is home to high-end boutiques, art galleries, fine dining, and other urbane attractions. Surrounded by water on all sides, it makes for a perfect scenic day of shopping. Check the calendar for special events throughout the year.

Coquina Beach

Just a few minutes’ drive over the Longboat Pass Bridge, this relaxed white-sand beach at the southern end of Anna Maria Island is worth a visit for its scenic sunset views. Hunt for shells, play some beach volleyball, and keep an eye out for passing pods of dolphins.

Quick Point Nature Preserve

A short (0.8-mile) walking trail wends its way through 34 acres of protected wetlands and mangrove lagoons. If you’re lucky you might spot a dolphin swimming through the seagrass, or watch a heron, egret, or ibis hunting for its dinner.

Frequently Asked Questions

  • What types of vacation rentals are available in Longboat Key?

    Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Longboat Key. From over 360 condo rentals, over 200 house rentals to over 10 villa rentals, we've got you covered. For even more variety, explore our Airbnb Categories to find the ideal space for your getaway.

  • Are there vacation rentals with a dedicated workspace in Longboat Key?

    Yes! Work meets play with ease at over 300 vacation rentals in Longboat Key featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Longboat Key?

    Four-legged friends are welcome in Longboat Key. Choose from more than 140 vacation rentals for guests traveling with pets.

  • How much does it cost to stay in house rentals in Longboat Key?

    Experience the best of Longboat Key with our house rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there Longboat Key house rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 120 house rentals with pools in Longboat Key, available on Airbnb. Make a splash and soak up the sun in style!

  • Do house rentals in Longboat Key have a gym?

    Absolutely! We offer over 20 house rentals with a gym in Longboat Key. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Longboat Key have self check-in?

    Absolutely! We offer over 60 house rentals with self check-in in Longboat Key. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Longboat Key have a bbq area?

    Absolutely! We offer over 80 house rentals with a bbq area in Longboat Key. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Longboat Key have free parking?

    Absolutely! We offer over 200 house rentals with free parking in Longboat Key. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly house rentals in Longboat Key?

    Longboat Key has more than 170 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

Destinations to explore

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