Longboat Key vacation rentals
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Top-rated vacation rentals in Longboat Key
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Home in Longboat Key
4.87 out of 5 average rating, 104 reviewsSummer House longboat key
Luxurious waterfront 3 Bedroom home with bay and and canal view with extra dock that can accommodate up to 21 ft+-heated pool, tropical landscaping with coconut palms, outside patio and grill. Fish on the dock and watch dolphins and manatee. Truly a tropical paradise just 7 minute Walk to your own private beach, It is a private home nestled on a canal that is 2 houses from Sarasota Bay. Our home is situated in the desirable quiet neighborhood of Country Club Shore minutes from at Armand’s circle
Apartment in Longboat Key
4.82 out of 5 average rating, 124 reviewsOcean Front Studio Special From $99/night
This complex is a 2 story bldg with only 14 condos, beautifully landscaped, with sophisticated charm and a casual beach atmosphere. The pictures are taken from the condo, so what you see is what you get, direct beautiful Ocean views. Sip your beverage of choice as you enjoy the sunsets and the balmy breezes on your large walkout private patio with a table, chairs, chaise lounges which faces the aqua waters of the Gulf of Mexico. This is a condo that you will want to return to year after year.
Jul 9 – 16
Island in Sarasota
4.97 out of 5 average rating, 298 reviews*MAY SALE! Sarasota #1 Luxury Villa Pool/Beach!*
Check our nearby sister properties for 2024 dates by clicking our host picture, then click picture again or "contact host". Or BOOK 2024 NOW, stay in Style magazines exclusive beachfront gem! This property OWNS THE BEACH!! UNIQUE PRIVATE POOL & BEACH combo is HEAVEN! Private ELEVATOR! 32,000/gl FREEFORM POOL, with 4 WATERFALLS, HOT GROTTO with HOT falls! NEW BBQ PIT AREA, BIKES, KAYAKS, and PADDLEBOARDS! WRAPAROUND BALCONY, CHEF kitchen. Hosted CELEBS! SHOPPING, FINE DINING, watch our VIDEOS!
Jan 22 – 29
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Longboat Key vacation rentals
Longboat Key condo rentals
Condo in Redington Beach
4.97 out of 5 average rating, 245 reviewsNoCleaningFees/AmazingBeachCondo/AwesomeAmenities2
Dec 20 – 27
Condo in Siesta Key
4.9 out of 5 average rating, 149 reviewsCozy Siesta Key studio 5 minute walk to Village
Nov 12 – 19
Condo in Bradenton Beach
4.9 out of 5 average rating, 123 reviewsBeachfront condo in paradise
Aug 25 – Sep 1
Condo in Siesta Key
4.96 out of 5 average rating, 268 reviewsOn the Beach; Siesta Key SunBum Studio
Jan 7 – 14
Condo in Treasure Island
4.99 out of 5 average rating, 150 reviewsSpectacular beach to bay views from this resort.
Sep 12 – 19
Condo in Redington Beach
4.91 out of 5 average rating, 107 reviewsRoyal Orleans and Redington Beach ( Studio 203 )
Nov 19 – 26
Condo in Indian Rocks Beach
4.79 out of 5 average rating, 223 reviewsWaterfront Condo w/ Boat dock, 2 min walk to beach
Dec 1 – 8
Condo in Bradenton
4.98 out of 5 average rating, 167 reviewsShorewalk full condo IMG Beaches Anna Maria
Aug 31 – Sep 7
Condo in St. Pete Beach
4.92 out of 5 average rating, 200 reviewsSunset Beach Condo in Treasure Island
Nov 10 – 17
Condo in Holmes Beach
4.99 out of 5 average rating, 122 reviewsBeach Escape - Make Memories on Anna Maria Island!
Oct 24 – 31
Condo in Siesta Key
4.95 out of 5 average rating, 148 reviewsWalk to Siesta Key Village and Beach
Sep 10 – 17
Condo in Holmes Beach
4.96 out of 5 average rating, 116 reviewsBeautiful beachfront condo for perfect vacation
Jul 3 – 10
Longboat Key home rentals
Home in Sarasota
4.96 out of 5 average rating, 107 reviewsNewly Renovated Ranch Minutes From Beach/Downtown
Jul 20 – 27
Home in Bradenton Beach
4.97 out of 5 average rating, 149 reviewsParadise! Steps2 Private Beach & Tropical Yard!
Dec 5 – 12
Home in Sarasota
4.94 out of 5 average rating, 124 reviewsRanch 2 blocks from Sarasota Bay
Dec 15 – 22
Home in Sarasota
5.0 out of 5 average rating, 274 reviewsStunning Luxe Casita- Gateway to Siesta Beach
Oct 26 – Nov 2
Home in Holmes Beach
4.96 out of 5 average rating, 157 reviewsSea AMI
Oct 7 – 14
Home in Sarasota
4.85 out of 5 average rating, 162 reviewsAuthentic Florida Bungalow near Downtown and Beach
Apr 29 – May 6
Home in Sarasota
4.99 out of 5 average rating, 123 reviewsAdorable Bungalow Fire pit/outdoor shower 2/1 Cute
Sep 19 – 26
Home in Sarasota
4.91 out of 5 average rating, 142 reviewsSunshine Suite, Minutes to Beach,Tropical Paradise
Nov 3 – 10
Home in Bradenton
4.97 out of 5 average rating, 189 reviewsHome near Anna Maria Beach - Hot Tub + Fire Pit
Nov 20 – 27
Home in Bradenton
4.94 out of 5 average rating, 150 reviewsPeaceful Braden River Oasis: Cottage
Aug 30 – Sep 6
Home in Sarasota
4.96 out of 5 average rating, 127 reviewsSarasota Florida -Wild Orchid Creek Cottage Home
Mar 24 – 31
Home in Siesta Key
5.0 out of 5 average rating, 122 reviewsOne-of-a-kind*Beach, Village, Dock & Private Pool!
Nov 7 – 14
Longboat Key villa rentals
Villa in Sarasota
4.89 out of 5 average rating, 181 reviewsEntire Standalone Villa,1.2k sf,1 block Lido Beach
Sep 13 – 20
Villa in Sarasota
4.96 out of 5 average rating, 130 reviewsNewly Renovated- 150 Yards to Beach & Restaurants!
Jan 10 – 17
Villa in Siesta Key
4.9 out of 5 average rating, 133 reviewsMermaid Villa Ocean Front!
Jul 3 – 10
Villa in Bradenton
4.83 out of 5 average rating, 133 reviewsElegant private home 3Bdr/3bth
Jun 29 – Jul 6
Villa in Redington Shores
4.9 out of 5 average rating, 106 reviewsBeachside 1 min to sand. Peaceful Walkable
Sep 9 – 16
Villa in Tampa
4.91 out of 5 average rating, 166 reviewsBusch Gardens, Moffitt, USF Charming Villa
Aug 10 – 17
Villa in Sarasota
4.9 out of 5 average rating, 176 reviewsHansen- Gorgeous 3BR/2BA Villa near Siesta Key
May 19 – 26
Villa in Clearwater
4.91 out of 5 average rating, 210 reviewsV3- 1 BR, waterfront villa, 2 min walk 2 beach
Dec 14 – 21
Villa in Safety Harbor
5.0 out of 5 average rating, 109 reviewsVilla Key West "Villas by Christine"
Jun 1 – 8
Villa in Sarasota
4.84 out of 5 average rating, 125 reviewsCozy, pet-friendly Home 3 miles to Siesta Key #1
Oct 6 – 13
Villa in St. Petersburg
4.84 out of 5 average rating, 106 reviewsSt. Pete Beach Oceanfront Villa Saltwater Pool
Oct 8 – 15
Villa in Tampa
4.91 out of 5 average rating, 125 reviewsVilla Perdomo Family
Sep 9 – 16
Quick stats about vacation rentals in Longboat Key
Total rentals | 800 properties |
---|---|
Rentals with a pool | 610 properties have a pool |
Pet-friendly rentals | 140 properties allow pets |
Family-friendly rentals | 580 properties are a good fit for families |
Total number of reviews | 8.3K reviews |
Nightly prices starting at | € 28 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 330 condo rentals, over 190 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 280 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.
Are there Longboat Key condo rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 290 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 320 condo rentals with free parking in Longboat Key. Enjoy a tailored experience with all the comforts you desire.
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