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
Apartment in Sarasota
4.89 out of 5 average rating, 586 reviewsCharming Apt. in old Florida home
Aug 24 – 31
Condo in Longboat Key
4.82 out of 5 average rating, 159 reviewsUpdated Beachfront Condo at Prestigious Long Boat
May 4 – 11
Condo in Sarasota
4.96 out of 5 average rating, 119 reviewsLido-Key- Tiny Studio Holiday Cottage-A
Oct 14 – 21
Guest suite in Bradenton
5.0 out of 5 average rating, 186 reviewsOff Anna Maria Island ~10min to beach w/salt pool
Jun 19 – 26
Guest suite in Sarasota
4.94 out of 5 average rating, 477 reviewsStudio Apartment. Priv Yard. 5 min to Siesta Key!
Oct 20 – 27
Apartment in Bradenton Beach
4.81 out of 5 average rating, 117 reviewsBradenton Beach apartment - Short walk to beach
Jul 31 – Aug 7
Island in Sarasota
4.97 out of 5 average rating, 301 reviews*NEW CX APR27 last min SALE Sarasota #1 Luxury!*
Jan 21 – 28
Condo in Siesta Key
4.89 out of 5 average rating, 151 reviewsCozy Siesta Key studio 5 minute walk to Village
Sep 4 – 11
Longboat Key condo rentals
Condo in Holmes Beach
4.98 out of 5 average rating, 108 reviewsNEW listing on AMI! Walk to fabulous beach front!
May 11 – 18
Condo in Redington Beach
4.97 out of 5 average rating, 457 reviewsAmazingBeachCondo/NoCleaningFee/AwesomeAmenities
Apr 18 – 25
Condo in Bradenton Beach
4.91 out of 5 average rating, 128 reviewsBeachfront condo in paradise
Nov 14 – 21
Condo in Redington Beach
4.94 out of 5 average rating, 356 reviewsBeach Condo, Heated Pool, 2 Minute Walk to Ocean
Oct 15 – 22
Condo in Holmes Beach
4.96 out of 5 average rating, 116 reviewsBeautiful beachfront condo for perfect vacation
Jul 20 – 27
Condo in Holmes Beach
4.99 out of 5 average rating, 124 reviewsBeach Escape - Make Memories on Anna Maria Island!
Apr 11 – 18
Condo in Siesta Key
4.96 out of 5 average rating, 274 reviewsOn the Beach; Siesta Key SunBum Studio
Apr 13 – 20
Condo in St. Pete Beach
4.91 out of 5 average rating, 208 reviewsSunset Beach Condo in Treasure Island
Nov 6 – 13
Longboat Key house rentals
Home in Sarasota
4.96 out of 5 average rating, 111 reviewsNewly Renovated Ranch Minutes From Beach/Downtown
Oct 6 – 13
Home in Sarasota
4.94 out of 5 average rating, 125 reviewsRanch 2 blocks from Sarasota Bay
Nov 4 – 11
Home in Sarasota
4.98 out of 5 average rating, 199 reviewsThe Key Lime Cottage 2 miles from Siesta Key Beach
Apr 9 – 16
Home in Sarasota
4.85 out of 5 average rating, 162 reviewsAuthentic Florida Bungalow near Downtown and Beach
Jun 26 – Jul 3
Home in Bradenton
4.96 out of 5 average rating, 198 reviewsHome near Anna Maria Beach - Hot Tub + Fire Pit
Oct 13 – 20
Home in Bradenton Beach
4.89 out of 5 average rating, 237 reviewsOhana Beachside 2 BR Bungalow - 150 ft from beach
Sep 24 – Oct 1
Home in Bradenton Beach
4.97 out of 5 average rating, 153 reviewsParadise! Steps2 Private Beach & Tropical Yard!
Apr 12 – 19
Home in Sarasota
4.9 out of 5 average rating, 131 reviewsThe lovely place getaway-SRQ
May 1 – 6
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
ﺩ.ﺇ110 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.
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.
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 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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