Vacation rentals in Longboat Key
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Top-rated vacation rentals in Longboat Key
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
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Popular amenities for Longboat Key vacation rentals
Other great vacation rentals in Longboat Key
Waterfront Condo, Private Boat Dock, Beach Access!
loved staying at Val's place. a great, private location in walking distance of the beach and delicious restaurants. a very cute park right next to the unit. would stay again
Beach & Town Posh Location! Jungle Paradise Studio
Loooooooooooved the pool area! We sat there in morning for coffee and at night for wine. The pool was gorgeous and an oasis. The bed super comfortable and linens high quality! Location was great! Super quiet and serene. Amazing stay and we’d recommend very highly! Thank you!
Sand Cay Resort - Renovated #319 great Gulf view
Fantastic location, great views, great beach. Condo was clean and kept up well. Had everything we needed, no issues during the stay, and had plenty of restaurants close by. Exactly the kind of spot we were looking for!
Close to the Beach+ Private heated pool and spa!
We had the best time - it was everything we could've wanted in a rental! This was our first time staying in Holmes Beach and we loved it. The house is close to everything in town. We used and enjoyed all the wonderful amenities that Craig provides - the golf cart (a must!), beach cruisers, beach wagon, umbrella and chairs. The pool, hot tub and hammock were also a highlight for us. We can't wait to come back!
"Enfuego!"
We had such an incredible time staying at this property! It has everything! Plenty to do even on rainy days. Can’t say enough about it. We had 8 adults and a baby and king beds for everyone which is hard to find. So private in the back yard and unique!
Lido Key FL Studio/Efficiency 5
I truly enjoyed staying here at William’s Airbnb. It was just as described and a great location close to everything. Thank you for having me! It was great!
Canal front, dock, heated Pool, near AMI+IMG
Claudia’s place was one of the best Airbnbs we’ve stayed at while visiting AMI. The home was beautiful and the master bedrooms en suite felt like your own personal spa! If you’re traveling with babies or toddlers there is no safety fence around the pool, but there are alarms on every door leading out to the pool area. Claudia was very accommodating and even let us to check in early which allowed us to have a whole extra day to enjoy the pool. We really enjoyed our stay here and we highly recommend booking with Claudia!
'Walk on the Beach" heated pool North End AMI
The place was great. Very comfortable. Lot's of seating inside and out. Pool is well maintained and was just the right temperature. The pool is small, so mainly good for relaxing and talking or for kids to play in. Not really something you can do laps in. 5 minute walk to a beautiful beach and 20 minute walk along the beach to restaurants and shops. Great fishing in the area.
Quick stats about vacation rentals in Longboat Key
Total rentals
890 properties
Nightly prices starting at
G$6,276Â GYD before taxes and fees
Total number of reviews
9.8K reviews
Family-friendly rentals
690 properties are a good fit for families
Pet-friendly rentals
130 properties allow pets
Rentals with a pool
740 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 10 villa rentals, over 450 condo rentals to over 220 house 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.
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 $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there Longboat Key condo rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 420 condo rentals with pools in Longboat Key, available on Airbnb. Make a splash and soak up the sun in style!
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 440 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 340 family-friendly condo rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for Condo Rentals in Longboat Key?
Enhance your stay in our Condo Rentals with the most popular amenities: over 40 homes with self check-in, over 140 homes with a gym, over 440 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.
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- Anna Maria Island
- Siesta Beach
- Dunedin Beach
- Anna Maria Public Beach
- Crescent Beach
- John's Pass
- Turtle Beach
- Caspersen Beach
- Bean Point Beach
- Busch Gardens Tampa Bay
- Raymond James Stadium
- Cortez Beach
- Lido Key Beach
- Amalie Arena
- Coquina Beach
- Gulfport Beach Recreation Area
- Vinoy Park
- North Beach
- Fort De Soto Park
- Manasota Key Beach
- Streamsong Resort
- Tampa Theatre
- Jannus Live
- Curtis Hixon Waterfront Park