
Vacation rentals in Longboat Key
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Top-rated vacation rentals in Longboat Key
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Popular amenities for Longboat Key vacation rentals
Longboat Key condo rentals

❤️ Hidden Gem steps away from #1 beach 🏖 Siesta Key

Relax in a Newly Renovated Beach Front Paradise

On the Beach; Siesta Key SunBum Studio

New Renovated Condo + Walk to Bay + 5-Min to AMI

Tropical Beachfront Penthouse-Beach Cottages

New Luxury 3/3 Condo in Margaritaville Resort

Indian Shores Gulf Front Rental

Siesta Key Beach Front Condo
Longboat Key villa rentals

Tampa heat pool /hot tub lake view near airport

Heated Pool! Huge Walk In Shower! 5 min to beach!

Villa Perdomo Family

Cozy, pet-friendly Home 3 miles to Siesta Key #1

#1 Rated Mansion • Heated Pool/Spa • Theater • Gym

5 min to Siesta Key, Heated Pool, Grill, WiFi

Florida Living

Entire Standalone Villa,1.2k sf,1 block Lido Beach
Longboat Key beach vacation rentals

Your DreamOasisAwaits: SiestaKeyEscape with Pool!

Quiet Beachfront Bungalow on Florida’s Gulf Coast

Beachfront w/ Stunning Sunsets in Prime Location.

Direct Ocean View Top Floor Renovated. 2BR, 2 Bath

Breathtaking Beachfront Views in Siesta Key

Siesta Key #1 Beach, pickle ball & tennis paradise

Beach Bungalow -Step in to the Sand! Indian Shores

Shorewalk full condo IMG Beaches Anna Maria
Quick stats about vacation rentals in Longboat Key
Total rentals
930 properties
Nightly prices starting at
$30 before taxes and fees
Total number of reviews
11K reviews
Family-friendly rentals
720 properties are a good fit for families
Pet-friendly rentals
170 properties allow pets
Rentals with a pool
780 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 420 condo rentals, over 220 house rentals to over 10 villa rentals, we've got you covered.
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 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 390 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 80 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 140 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 40 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 420 condo rentals with free parking 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 320 family-friendly condo rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
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- Anna Maria Island
- Siesta Beach
- Crescent Beach
- John's Pass
- Busch Gardens Tampa Bay
- Raymond James Stadium
- Dunedin Beach
- Turtle Beach
- Caspersen Beach
- Coquina Beach
- Lido Key Beach
- Anna Maria Public Beach
- Cortez Beach
- Vinoy Park
- Amalie Arena
- Bean Point Beach
- Streamsong Resort
- Gulfport Beach Recreation Area
- Jannus Live
- Manasota Key Beach
- ZooTampa at Lowry Park
- North Beach
- Adventure Island
- River Strand Golf and Country Club
- Family travel hub Tips and inspiration
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- Outdoor adventure Explore nature with the family
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- Kid-friendly state parks Check out these family-friendly hikes