Longboat Key vacation rentals
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Top-rated vacation rentals in Longboat Key
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
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Get the amount of space that is right for you
Popular amenities for Longboat Key vacation rentals
Longboat Key beachfront vacation rentals
Condo in Indian Shores
4.86 out of 5 average rating, 111 reviewsBeach Fun With Views - Indian Shores, Florida
Condo in Indian Shores
4.97 out of 5 average rating, 148 reviewsSunset Beach Retreat
Rental unit in Indian Shores
4.95 out of 5 average rating, 122 reviewsBeach Front Condo!
Condo in Venice
4.96 out of 5 average rating, 101 reviewsVintage Villa, Thirty-Five
Condo in Madeira Beach
4.91 out of 5 average rating, 119 reviewsArie Dam 302, Beach Front Condo - 2Bed/2Bath
Rental unit in Indian Rocks Beach
4.95 out of 5 average rating, 152 reviewsDirect Ocean View Top Floor Renovated. 2BR, 2 Bath
Condo in Clearwater Beach
4.92 out of 5 average rating, 125 reviewsBeachfront Condo with Centerline Sunsets
Bungalow in Indian Shores
4.92 out of 5 average rating, 233 reviewsBEACH Bungalow Steps from the SAND - Indian Shores
Longboat Key house rentals
Home in St. Petersburg
5 out of 5 average rating, 8 reviewsHistoric Rawls House of St Pete
Home in Tampa
4.93 out of 5 average rating, 108 reviewsHouse at North Tampa 3BR & 2BA + Backyard
Home in Tampa
4.87 out of 5 average rating, 322 reviewsBeautiful Home In S Tampa Near Water & Downtown
Home in East Tampa
4.72 out of 5 average rating, 95 reviewsStylish Seminole Heights House
Home in St. Petersburg
5 out of 5 average rating, 33 reviewsCali Casa by Crescent Lake & downtown St. Pete
Home in Largo
4.85 out of 5 average rating, 117 reviews#RespectCreation
Home in Holmes Beach
4.85 out of 5 average rating, 26 reviewsFins Up! - Renting, 11/2024!
Home in Seffner
4.92 out of 5 average rating, 12 reviewsTampa Bay Getaway Seffner-Brandon FL 4 bed 2 bath
Longboat Key villa rentals
Villa in Sarasota
4.96 out of 5 average rating, 164 reviewsNewly Renovated- 150 Yards to Beach & Restaurants!
Villa in Sulphur Springs
4.88 out of 5 average rating, 206 reviewsBusch Gardens, Moffitt, USF Tropical Villa
Villa in Safety Harbor
5 out of 5 average rating, 128 reviewsVilla Key West "Villas by Christine"
Villa in Tampa
4.9 out of 5 average rating, 161 reviewsVilla Perdomo Family
Villa in Sarasota
4.75 out of 5 average rating, 124 reviewsAloha Villa Pet Friendly 3 miles to Siesta Key #2
Villa in Clearwater Beach
4.91 out of 5 average rating, 221 reviewsV3- 1 BR, waterfront villa, 2 min walk 2 beach
Villa in Largo
4.91 out of 5 average rating, 112 reviewsPoolside Palms Private Pool & Game Room - 7 Min to Indian Rocks Beach
Villa in Siesta Key
4.91 out of 5 average rating, 152 reviewsMermaid Villa Ocean Front!
Quick stats about vacation rentals in Longboat Key
Total rentals
910 properties
Nightly prices starting at
$30 before taxes and fees
Total number of reviews
9K reviews
Family-friendly rentals
700 properties are a good fit for families
Pet-friendly rentals
170 properties allow pets
Rentals with a pool
740 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 230 house rentals, over 440 condo 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 330 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 170 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 140 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 bbq area?
Absolutely! We offer over 70 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 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 50 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 free parking?
Absolutely! We offer over 230 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 200 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
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