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
Condo in Siesta Key
4.87 out of 5 average rating, 210 reviewsSiesta Key Beach Community!
Jun 21 – 28
Guesthouse in Osprey
4.99 out of 5 average rating, 286 reviewsCozy Cottage by the Bay
May 31 – Jun 7
Condo in Sarasota
4.96 out of 5 average rating, 120 reviewsLido-Key- Tiny Studio Holiday Cottage-A
Jul 30 – Aug 6
Home in Longboat Key
4.9 out of 5 average rating, 105 reviewsLongboat Key Beach House
May 9 – 16
Guest suite in Bradenton
5.0 out of 5 average rating, 187 reviewsOff Anna Maria Island ~10min to beach w/salt pool
Jul 18 – 25
Apartment in Sarasota
5.0 out of 5 average rating, 117 reviewsNew Apartment In a Private House Near Siesta
Oct 19 – 26
Condo in Siesta Key
4.83 out of 5 average rating, 237 reviewsSiesta Key 1/1 King bed “Sunset Suite” Pool Kayaks
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
Nov 13 – 20
Condo in Siesta Key
4.89 out of 5 average rating, 152 reviewsCozy Siesta Key studio 5 minute walk to Village
Dec 4 – 11
Condo in Tierra Verde
4.96 out of 5 average rating, 237 reviewsNatural Beauty on Tierra Verde, Waterfront Condo
Apr 2 – 9
Condo in Holmes Beach
4.99 out of 5 average rating, 125 reviewsBeach Escape - Make Memories on Anna Maria Island!
Sep 4 – 11
Condo in Sarasota
4.8 out of 5 average rating, 199 reviewsNear beach. Pool view. King bed. Daily rentals
Jan 8 – 15
Condo in Bradenton Beach
4.91 out of 5 average rating, 129 reviewsBeachfront condo in paradise
Apr 12 – 19
Condo in Indian Shores
4.89 out of 5 average rating, 116 reviewsGulf Side Florida Charm 1/1 Condo 60 Steps To Sand
Sep 7 – 14
Longboat Key house rentals
Home in Sarasota
4.96 out of 5 average rating, 128 reviewsSarasota Florida -Wild Orchid Creek Cottage Home
Mar 9 – 16
Home in Bradenton Beach
4.97 out of 5 average rating, 153 reviewsParadise! Steps2 Private Beach & Tropical Yard!
Dec 7 – 14
Home in Sarasota
4.94 out of 5 average rating, 126 reviewsRanch 2 blocks from Sarasota Bay
Nov 5 – 12
Home in Sarasota
4.99 out of 5 average rating, 201 reviewsThe Key Lime Cottage 2 miles from Siesta Key Beach
Oct 4 – 11
Home in Holmes Beach
4.95 out of 5 average rating, 158 reviewsSea AMI
Aug 29 – Sep 5
Home in Sarasota
4.96 out of 5 average rating, 111 reviewsNewly Renovated Ranch Minutes From Beach/Downtown
Oct 12 – 19
Home in Bradenton
4.96 out of 5 average rating, 203 reviewsHome near Anna Maria Beach - Hot Tub + Fire Pit
Sep 5 – 12
Home in Bradenton Beach
4.8 out of 5 average rating, 121 reviews50 Steps to Beach. Hot Tub! 1bd modern cottage
Sep 11 – 18
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
$30 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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