
Waterfront holiday rentals in Longboat Key
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Top-rated waterfront accommodation in Longboat Key
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Popular amenities for Longboat Key waterfront rentals
Waterfront apartment accommodation

B⎈AT HOUSE OASIS⚓Steps to the water⚓Walk to Beach!
Nice little place for two, close to everything. Nice view. had red snapper on the new grill. Fun!

Newly Remodeled Beachfront Studio - On the sand!
Jeffery’s rental was perfect. He has such an eye for detail and it’s beautifully decorated. Our view of the ocean from the sitting area outside the rental was spectacular! The space contained everything you would possibly need and was extremely comfortable. This is our second stay at Shell Cove 1 and we highly recommend it to others.

Las Palmas Beach Rentals Unit 1
excellent location, everything super clean, thank you for everything

Direct Ocean View Top Floor Renovated. 2BR, 2 Bath
We absolutely loved our stay at Scott’s place. The condo was sparkling clean- I am extremely picky about cleanliness and was not disappointed. The kitchen was well equipped and we appreciated all of the beach gear Scott had available for use. We loved the location and the view from the balcony is unmatched. Scott was quick to respond with the minor issue we had at check in and quickly resolved the issue. We had the best time and will definitely be back!

Siesta Premier Location - The 'Calm of Siesta'
I visit Sarasota every year and stay each time at a new place. This year I wanted to do something closer to the beach and Siesta Village. Matt’s spot was perfectly located for this due to being so close to the beach and every night we walked to the village for dinner/nightlife which was about 15 minutes walking distance. Overall a great place for 1-4 people if you’re looking for a nice chill vacation.

Popular Beachside Studio w/ Shady Patio & Palms!
Had a great time staying here! We can for a long weekend and Lara was super helpful to accolade us for showing up early and wanting to get our beach vacation started! The until was so cute and perfect for 2 people. The beach is literally steps from your door. Made it easy to go back and forth if we forgot something inside or if we needed to take a couple trips to get all of our beach gear set up. There wasn’t a ton to do near on treasure island so we took a quick 20 minute uber into St. Pete’s which has so much to do, great restaurants, and awesome night life!

Waterfront Modern Chic #1 Clearwater Beach
My family and I had such an amazing time staying at Lina's place! The apartment is even more beautiful than the picture suggest. It was absolutely spotless and we had such a nice time hanging in the pool as well as sitting out back and watching the boats go by. The beach is a quick 5 minute walk away as well as several other dining spots. Would love to come back again soon!

The Coastal Nest w/King Bed
Great place to stay with a great view! Very nice restaurant within walking distance too.
Waterfront house rentals

“Enfuego!”
When I saw this new listing, I hesitated—no reviews and almost too-perfect photos. But the owners quickly answered my questions, were responsive, and I’m so glad we booked. The home is exactly as pictured: spotless, spacious, beautifully designed. The pool area is a dream—plenty of space for our group of 11 (with 4 kids), with waterfall features, a sauna, and even a sandy play area. The movie room and golf simulator were a hit too! Beds are comfy, rooms are big and inviting, Wi-Fi is great. Peaceful, safe neighborhood with tons of privacy. Carter and Naomi were responsive and kind to any concerns we had, and took care of everything. Amazing hosts. This home is a gem.

North Shore Six
This place is worth more than what we paid. Having the docks for fishing and the beach a block away made this place exquisite. The beach was practically empty every day, which is what we loved. Our stay was clean and comfortable. We recommend staying with Cole!

Beach Retreat! Bikes, Paddleboards, Sauna & more!
Beautiful home and surrounding area, Pristine home in brand new condition. Expertly furnished, lots to do for teenagers, they loved the ice bath! Well stocked kitchen. The host was very responsive and helpful would definitely recommend this location and home. Happy vacationing.

Relaxing 3BR/2BA POOL Home w. Pond View & HOT TUB
Staying with Jose & Sara was an amazing experience! (Again!) We have stayed at their home previously, and we really enjoyed ourselves. When looking for a home to rent for vacation this time, we were excited to see Jose & Sara’s house! We jumped at the opportunity to rent this perfectly sized home again. Jose & Sara do such a great job of making you feel at home. There were towels folded on the beds and so many extra beach towels for the pool! There was even a little snack tray for us when we arrived. The directions to enter the home were easy to follow. We had one super tiny issue with the coffee pot, & Jose handled it quickly & efficiently. The pool is such a highlight of a perfect home! Perfect size to float around & enjoy the sun. The hot tub felt amazing after a 17 hour drive. You literally feel like you entered paradise, right outside the back door. There is a nice shady area with a fan as well. Showers & bathrooms were good sizes! I love the shower heads! I was able to enjo

Discount 33% June 3-Day and July 4-Day w/Dock-Pool
My family and I absolutely loved our experience!! The hosts were attentive and quick to respond with clear instructions. House was cleaned and amply stocked with everything you need for a family of five. The pool was amazing and we definitely saved some money by having a fully functioning kitchen and grill for dinner and lunch. Very close to the beach. Two scoops ice cream is amazing with quick service as it is very busy and the general store was only a quick drive to get anything else we needed or forgot to pack. Bean Point beach is where you want to be if you don’t like overcrowded beaches, however, parking is limited so I recommend getting there early!! Also recommend renting a golf cart for extended stays and if you have kids like I did. Plenty of options around the island. I would recommend 100% and we definitely will be back!!

Sunset View
We had a blast! The house was everything we expected and Renee was very responsive! Zero complaints! 10/10

Downtown Oasis: Poolside Condo, Patio & Gym
Stayed here for the national rowing competition for one week. The place is lovely - very clean, the complex is nice & the pool is great. It was a perfect location for us - halfway between the race course where we needed to be every day and close to downtown. The beach wasn’t far either and I liked the location and the complex very much. We felt safe and it was pretty quiet and peaceful. The owner is responsive and detail oriented with how to check in, get into the unit, etc. I would stay here again.

Superhost! Fully Renovated Sarasota Home
Great house, everything clean and comfortable, easy to get to popular restaurants and beaches, will definitely come back!
Waterfront condo accommodation

"Jewel At The Shores" Gulf Front, sleeps 5
Excellent location! Everything you need is in the condo. Hope to come back soon!

On the Beach; Siesta Key SunBum Studio
My daughter and I stayed for a mother daughter girls trip and had a blast! They made sure to take care of every little detail to make you feel comfortable and at home. Even checking in and making sure we made it ok. It was very clean and the location was amazing. Easy to get around on the trolly if we didn't want to drive and literally steps away from the beautiful white sand and clear turquoise beach. Do yourself a favor and book the trip!

6 min to Siesta Beach | Heated Pool | Lake View
Doris's AirBnB was exactly as listed. It was very clean. The neighborhood was quiet. It was in the perfect location. We had no problems at all. I would definitely book again.

The Seabreeze Cottage with peaceful water views
Dear Angela, Thank you so much for hosting us! We absolutely love your decor every detail was so thoughtfully done and made the space feel cozy and "beachy". We truly enjoyed our stay and appreciated how comfortable and well-kept everything was. Hope to visit again someday. All the best. Jianfeng & Yangqing

Spectacular beach to bay views from this resort.
Our stay was great! The place and location were perfect! We had absolutely everything we needed. Communication was awesome! Thanks so much!! Lara and Thomas Boulder Co

Modern Waterfront Condo - Captivating Sunset Views
Rosana was an excellent host- very responsive, kind, and accommodating. Fun location on the bay with a great view, pool with towel service, and bar/grill with great burgers. Fire pit on the little beach at night with great view of sunset. The unit is in a quiet location within the complex with a view of the beach and bay. The trade-off is that the unit is a bit far from the elevator (though close to stairs). Great experience overall.

~Shore Thing~ Coastal Exquisite Waterfront Condo
My new husband and I stayed at Rachel’s condo for our honeymoon and it was perfect! This was our first time in Treasure Island and I would love to come back and stay here again. Everything was exactly as described, clean, and beautiful! We saw a manatee in the intercoastal waters one morning, and the patio was a peaceful place to relax. The beach is just a 5 minute straight walk from the condo which was great. We visited the Florida and Clearwater Aquariums, and spent 2 days at Honeymoon Island State Park looking for shells and enjoying the peaceful beach. All of these were about 45-55 minutes from the condo. It stormed a couple of days so we appreciated how cozy the condo was and the large TVs, and Rachel provided everything we would need. We can’t wait to come back!

Beachfront condo in paradise, Anna Maria Island
We had a wonderful stay! The location can’t be any better! The condo was clean and well equipped. Communication was clear and fast. Very nice and quiet condo. My recommendation for those staying (lucky you!!) is to bring your breakfast and lunch (at least), because once there you won’t want to leave! You will be at walking distance from some restaurants and there is a nice beachfront restaurant and bar next door. Loved waking up and having my cup of coffee on the balcony and walking along the sea shore. What can I say, I would definitely be going back! The hosts are truly superhosts. Totally recommended. Thanks Dan and Crystal for sharing your space with us!
Quick stats about waterfront rentals in Longboat Key
Total rentals
240 properties
Nightly prices starting at
$77 AUD before taxes and fees
Total number of reviews
4.3K reviews
Family-friendly rentals
180 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with a pool
210 properties have a pool
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- Anna Maria Island
- Siesta Beach
- Anna Maria Public Beach
- Dunedin Beach
- Crescent Beach
- John's Pass
- Turtle Beach
- Caspersen Beach
- Bean Point Beach
- Raymond James Stadium
- Busch Gardens Tampa Bay
- Cortez Beach
- Lido Key Beach
- Amalie Arena
- Coquina Beach
- Gulfport Beach Recreation Area
- North Beach
- Fort De Soto Park
- Manasota Key Beach
- Vinoy Park
- Jannus Live
- Streamsong Resort
- Tampa Theatre
- ZooTampa at Lowry Park