
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
Longboat Key home rentals

Modern Resort-Style Townhouse
We had a great time at Gleb’s place. The townhouse was beautiful and very clean. Comfortable beds. The bunk bed has a trundle mattress on the bottom which worked out great for my youngest child. The clubhouse is amazing. Would definitely stay here again.

Hot tub/Pool! Pet friendly (for fee) Fenced yard
My family and I had a great stay during our spring break. We had our 3 kids (ages 2, 7, and 12) and they absolutely loved the pool and hot tub. The house was very clean and the beds were comfortable. Several beaches nearby on Anna Maria Island. We will definitely be back and our kids already want us to plan our next vacay here. Thanks Jen and Brittany 💕

Heated Pool/Ping Pong/ Foosball/Gym/Walk 2 Beach
House is very spacious had everything we needed there was a kids park within walking distance and the beach was close as well

Walk to the beach.
Betty is an excellent host. Clean and spacious for a studio! Loved the pool. Close to Siesta Beach and nice restaurants. We will definitely come to rest and relax at this peaceful Airbnb. Thank you

Comfortable & modern house in Central Bradenton
1. My stay at this Airbnb in Florida was great from start to finish. 2. The place was very clean and well-kept, just as described. 3. I didn’t experience any problems during my stay. 4. The host was responsive and always replied in a timely manner. 5. I would definitely stay here again and recommend it to others.

Luxury Home centrally located in Tampa Bay!
We all loved the house! It was clean, ample parking in the driveway, close to where we needed to be and the host was very attentive to all of our questions. We would definitely recommend the rental and even use it in the future!

Siesta Peace Retreat a private home rental
Tracy's place is wonderful, and she is very attentive. She gave us lots of tips on what to do and where to go, which was a big plus. The backyard is very relaxing with a lovely spa where we enjoyed the evenings. The house was super clean, and the beds were very comfortable. If I return to Siesta Key, I will definitely stay there again.

Amazing Location! Amazing Amenities!
Jennifer offered a beautiful, clean home that was as described and perfect for our family! She was very accommodating and quick to respond! Our family enjoyed all the home and resort had to offer and can’t wait to book our next vacation using one of Jennifer’s properties!
Longboat Key condo rentals

*Waterfront *2 Bedroom Condo *Amazing Sunsets*Pool
Our family had a wonderful time at this condo! We enjoyed waking to see the ocean every day and also had enough space to relax on our vacation. Helena provides a beach bag with towels and sand toys that were a very nice touch for our beach day. The staff at the bar/restaurant were great and we also felt safe with the 24 hour security guards on duty. This place really made our trip extra special!

Amazing main floor condo at Avalon
The condo is very beautiful and clean! it had all the amenities you would need. The pool was fantastic. It's only around 10 minutes to drive to the beach. Checking in and out was a breeze. Catinca is a friendly and amazing host. Highly recommend!! Would definitely come back.

Renovated Condo! Across the Street From The Beach
Great unit across the street from the beach. The photos matched the amenities. We felt right at home. Everything was fresh and clean. The neighbors were friendly. Beach chairs, umbrella, wagon, towels, and cooler were provided. Nice restaurants and market were within a 10-15 minute walk. We enjoyed our stay here.

Arie Dam 302, Beach Front Condo - 2Bed/2Bath
Our family of 6 had the best time! Our condo was so nice, clean, and comfortable. It was great to have beach towels and chairs to use as well!! The beach and view was amazing. We had no idea it would be so beautiful. The pool wasn’t quite ready but that didn’t matter (repairs due to the hurricane) the ocean was enough. Our son rented a fishing pole from Hubbards Marina and had the best time fishing off the shore while our other kids swam. We would go back and stay at the same place again. The beach was not crazy busy. Early mornings and late evenings were so peaceful.

Indian Shores Gulf Front Rental
We had a fantastic stay at this beachfront condo in Indian Shores! Traveling with our two young children, we really appreciated how easy it was to get to the beach—just steps away, making it perfect for a stress-free family vacation. The condo was clean, comfortable, and had everything we needed for our stay. The hosts were extremely responsive and accommodating, especially when our flight plans changed, which made the trip even smoother. We would absolutely stay here again and highly recommend it to anyone looking for a relaxing beach getaway!

5 *Waterfront Condo,3 Beds,2 Baths, Pool, HOT-TUB.
The condo was beautiful. Clean and spacious. Lots of amenities. Close to the public beach, restaurants, bars, and shops. Plus David ordered a perfect week of weather for us! Wonderful.

Florida Bella Rosa-2 spas & pools near IMG/beaches
We are already looking to see when we can come back to Florida and stay in Daniel's rental again! It has everything you need, it is well-kept, and it is close to everything you want/need (the beach, Detwiler's, Publix, stores, restaurants). It is in a safe location. The Shorewalk ammenities (pools and hot tubs) are nice as well. Even though one pool's heater was broken, there was another pool to choose from and two hot tubs. He checked-in with us to make sure check-in went well and to make sure that our stay was going well. Daniel provided thorough instructions and recommendations for everything you could possibly need. He was a great host with a great home away from home!

Beachfront Condo in Exclusive Resort
This was our second spring break at Ocean Club and already booked our third trip. It’s a great place for families.
Longboat Key villa rentals

Newly Renovated- 150 Yards to Beach & Restaurants!
This was a great place with a fabulous restaurant right across the street- big water fish market— so good. Cannot recommend it enough! The Airbnb was adorably decorated, and comfortable. The beach space was between 2 different resorts, so it was a pretty narrow space to accommodate all the people who needed to use it, but still was a great beach experience and so close! The trolley makes travel to the village so easy. But we did love that there was a driveway for our rental car as well. Amazing place to stay— would love to stay again!

Busch Gardens, Moffitt, USF Tropical Villa
The house was as described. It was clean and actually felt like a “home” when you walked in. Plenty of room, well stocked, and comfy. The location was PERFECT for our trip. Centrally located to shops, restaurants, and all the tourist attractions. BG, The Zoo, & The Aquarium were all less than 20 minutes away. We would definitely stay again.

Villa Key West "Villas by Christine"
I would go back next week if I could. Christine's place is outstanding in every possible way. The location is one block off the main drag, so close to everything, but quiet. Beautiful, high-end everything. It was a three-day girls' trip and we were so busy that we didn't spend a lot of time at the house, but I wanted to spend a week. Only one word of caution, I had a big suitcase because I'd been somewhere else first where the weather was cold. That was unwieldy to carry up the narrow circular staircase. But a sensible bag would have been no problem. There's a parking spot right out front. A/C was great though we didn't need it much, and my friend loved the patio downstairs off that bedroom. Perfect Airbnb and I hope to return.

Villa Perdomo Family
We loved our stay at Antonio’s! Place was very clean, had lots of space and had everything we needed. We used the fire pit and the pool each day. We were in town for the women’s basketball final four. Took a little longer to get downtown than we hoped but that was due to traffic. I would highly recommend!Antonio was very responsive, let us get in the house early and was quick to respond. If ever traveling to Tampa I would book again.

Aloha Villa Pet Friendly 3 miles to Siesta Key #2
I visited Sarasota with my family from the state of Rhode Island from April 4 to April 7 and we stayed at Jason’s & Laura house and it was an amazing experience. The house was very clean and organized. The house is located on a great neighborhood, super safe and great amenities. The house was stocked with beach supplies like beach chairs, beach towels, a boogie board and a beach cooler that was so nice. The house was exactly what we were expecting, I would recommended to everyone. Thank you Josh and laura.

1 house to beach entrance. Peaceful. Walk to dine.
This place was great! So close to the beach. We have been staying in this area for 20+ years and love coming here every time. Nancy’s home was clean and perfect for what we needed.

Entire Standalone Villa,1.2k sf,1 block Lido Beach
Absolutely perfect location! Walking distance to Lido beach and St. Armand’s Circle. Rooms and amenities were very spacious and comfortable. Loved having beach equipment, beach towels, washer/dryer available. Easy checkin! Had the best time!

Updated Downtown Sarasota Villa, 2b/2b
Close to everything in Sarasota, downtown and the coast. Super cute home and quiet surroundings.
Quick stats about vacation rentals in Longboat Key
Total rentals
890 properties
Nightly prices starting at
ﺩ.ﺇ110 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 220 house rentals, over 10 villa rentals to over 450 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.
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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- John's Pass
- Crescent Beach
- Bean Point Beach
- Cortez Beach
- Lido Key Beach
- Busch Gardens Tampa Bay
- Amalie Arena
- Raymond James Stadium
- North Beach
- Clearwater Beach
- Vinoy Park
- Coquina Beach
- Manasota Key Beach
- Fort De Soto Park
- Tampa Theatre
- Curtis Hixon Waterfront Park
- Jannus Live
- Streamsong Resort
- ZooTampa at Lowry Park
- Splash Harbour Water Park
- Adventure Island
- Myakka River State Park
- Englewood Beach
- Alafia River State Park