Longboat Key vacation rentals
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Top-rated vacation rentals in Longboat Key
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Popular amenities for Longboat Key vacation rentals
Other great vacation rentals in Longboat Key
Cottage in Nokomis
4.98 out of 5 average rating, 123 reviewsStaycation Sanctuary - 100% Smoke-Free Property
Aug 11 – 18
Guesthouse in Sarasota
4.86 out of 5 average rating, 371 reviewsThe Cottage, very close to Siesta Beach!
Sep 23 – 30
Guest suite in Bradenton
5.0 out of 5 average rating, 188 reviewsOff Anna Maria Island ~10min to beach w/salt pool
Jul 20 – 27
Guesthouse in Sarasota
5.0 out of 5 average rating, 102 reviewsMagical Guesthouse 1 mi from SRQ airport
Aug 28 – Sep 4
Cottage in Bradenton Beach
4.96 out of 5 average rating, 141 reviewsBradenton Beach Sunsets 3, Anna Maria Island, FL
Jan 18 – 25
Condo in Siesta Key
4.93 out of 5 average rating, 181 reviewsSiesta key getaway!
Jul 4 – 11
Island in Sarasota
4.97 out of 5 average rating, 303 reviews*NEW May 17 CX 30% OFF! Sarasota #1 Luxury Villa*
Nov 3 – 10
Apartment in Sarasota
5.0 out of 5 average rating, 117 reviewsNew Apartment In a Private House Near Siesta
Oct 19 – 26
Longboat Key condo rentals
Condo in Redington Beach
4.97 out of 5 average rating, 459 reviewsAmazingBeachCondo/NoCleaningFee/AwesomeAmenities
Nov 9 – 16
Condo in Siesta Key
4.96 out of 5 average rating, 276 reviewsOn the Beach; Siesta Key SunBum Studio
Mar 4 – 11
Condo in Bradenton Beach
4.91 out of 5 average rating, 131 reviewsBeachfront condo in paradise
Dec 11 – 18
Condo in Holmes Beach
4.98 out of 5 average rating, 108 reviewsNEW listing on AMI! Walk to fabulous beach front!
Jun 22 – 29
Condo in Holmes Beach
4.99 out of 5 average rating, 125 reviewsBeach Escape - Make Memories on Anna Maria Island!
Apr 27 – May 4
Condo in Indian Shores
4.96 out of 5 average rating, 143 reviews1 BR direct beachfront! Now avail. 8/29-9/11.
Dec 10 – 17
Condo in Siesta Key
4.9 out of 5 average rating, 175 reviewsSteps to Beach & Siesta Key Village-Village condo
Oct 4 – 11
Condo in Venice
4.87 out of 5 average rating, 141 reviewsThe Studio at the Beach 56
May 19 – 26
Longboat Key house rentals
Home in Sarasota
4.96 out of 5 average rating, 129 reviewsSarasota Florida -Wild Orchid Creek Cottage Home
Oct 4 – 11
Home in Bradenton
4.96 out of 5 average rating, 204 reviewsHome near Anna Maria Beach - Hot Tub + Fire Pit
Dec 12 – 19
Home in Bradenton Beach
4.97 out of 5 average rating, 153 reviewsParadise! Steps2 Private Beach & Tropical Yard!
Apr 26 – May 3
Home in Holmes Beach
4.95 out of 5 average rating, 158 reviewsSea AMI
Aug 16 – 23
Home in Sarasota
4.94 out of 5 average rating, 126 reviewsRanch 2 blocks from Sarasota Bay
Aug 2 – 9
Home in Sarasota
4.96 out of 5 average rating, 111 reviewsNewly Renovated Ranch Minutes From Beach/Downtown
Jul 28 – Aug 4
Home in Sarasota
4.96 out of 5 average rating, 246 reviewsLovely guest house
Jul 30 – Aug 6
Home in Sarasota
4.85 out of 5 average rating, 162 reviewsAuthentic Florida Bungalow near Downtown and Beach
Jun 26 – Jul 3
Quick stats about vacation rentals in Longboat Key
Total rentals
780 properties
Rentals with a pool
650 properties have a pool
Pet-friendly rentals
130 properties allow pets
Family-friendly rentals
570 properties are a good fit for families
Total number of reviews
8.7K reviews
Nightly prices starting at
G$6,254 GYD before taxes and fees
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 190 house rentals, over 10 villa rentals to over 360 condo 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 130 vacation rentals for guests traveling with pets.
Are there Longboat Key condo rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 340 condo rentals with pools in Longboat Key, available on Airbnb. Make a splash and soak up the sun in style!
How much does it cost to stay in condo rentals in Longboat Key?
Experience the best of Longboat Key with our condo rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there family-friendly condo rentals in Longboat Key?
Longboat Key has more than 250 family-friendly condo rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do condo rentals in Longboat Key have a bbq area?
Absolutely! We offer over 90 condo rentals with a bbq area in Longboat Key. Enjoy a tailored experience with all the comforts you desire.
Do condo rentals in Longboat Key have a gym?
Absolutely! We offer over 80 condo rentals with a gym in Longboat Key. Enjoy a tailored experience with all the comforts you desire.
Do condo rentals in Longboat Key have self check-in?
Absolutely! We offer over 50 condo rentals with self check-in in Longboat Key. Enjoy a tailored experience with all the comforts you desire.
Do condo rentals in Longboat Key have free parking?
Absolutely! We offer over 340 condo rentals with free parking in Longboat Key. Enjoy a tailored experience with all the comforts you desire.
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