
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

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

Siesta Key - Poolside Suite - Studio - Free kayaks
Such a great location! The breeze trolley stops right out front and made it super easy to get around. The place was super clean and quiet. The pool right out the door was perfect! We plan on coming back next year and will for sure stay in one of Lisa’s properties. She was so easy to communicate with and very responsive. Loved our stay!

Seaside Chic #3 Waterfront Clearwater Beach
Amazing stay! The place was spotless, cozy, and exactly as described. The host was friendly and helpful – highly recommend

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!

Ideal Madeira Beach Retreat~ Family Friends &Fido!
Location of this condo was excellent! We had everything we needed for the beach and our stay. The furniture was very comfortable and we slept well. We would definitely pick this condo again when traveling to Madeira!
Waterfront house rentals

Mins to Beach + IMG+ Hot tub + Heated Pool!
We had an amazing stay! We had a family of 8 and the house was perfect for all of us. The house was absolutely beautiful! It was super clean. We spent a lot of time in the pool and hot tub. The outdoor table also has a fire pit which was perfect at night. There were lots of amenities provided. There’s plenty of beach supplies/ extra towels. The house was filled with lots of stuff we didn’t have to pack, because it was already there. The beach is super close, about 10 minutes away, which was a bonus. Ashley has been wonderful! She’s super responsive and even allowed us to check in an hour early. We have a great vacation! We couldn’t recommend this place more! The perfect family vacation home.

"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.

Luxe! / Beach Access & Trolley/ Restaurants!
This location was awesome for our family vacation. We had 8 people and we had plenty of room. The outdoor area was relaxing. It was a comfortable house for both adults and kids. The proximity to the beach is great. We really appreciated the beach chairs, toys, cooler and umbrella. Hated to leave!

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
Thank you for hosting us! The home is beautiful. Great neighborhood and loved all the extra touches. This was a home away from home. We were very comfortable, safe, and loved the pool! We hope to be back in the near future. Thank you!

Discount 33% June 3-Day and July 4-Day w/Dock-Pool
Just want to begin by saying how appreciative I was of Michelle and her husband. They were super responsive and attentive to all of our requests/questions. We have stayed at numerous high-class locations and this was by far my favorite. The price compared to nearby locations was worth every dollar. The home was very welcoming, modern, and just overall paradise. Absolutely loved the swimming pool and dock right off of the back of the house. The space was very well designed. The location was within 15 minutes of everything we could have asked for out of the island. 11/10 I would recommend to anyone looking to have an amazing, peaceful retreat.

Sea Gem | Waterfront w/ Pool, Dock + Paddle/Kayaks
We loved the beautiful modern home, fully stocked kitchen, cool fireplace & pool. Our kids loved having access to a dock & kayaks where they could fish all day! There was plenty of space for everyone to feel comfortable. Found THE BEST Latin grocery store 5 minutes away with fresh chips, salsa & super yummy desserts! We'll be back.. Thank you, Landon!
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!

2/2 JW Marriott Resort/Spa Clearwater Beach, 811
What property is top notch! JW Marriott Clearwater staff was fantastic. I would recommend this property to anyone looking for a great view and beach access. Thank you!

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!

Sandcastle Dreams
We had a wonderful stay at Ammey’s place. The location was perfect. It was close to all of the restaurants and shops on Bridge Street, it was an easy walk down the beach to other restaurants located right on the beach. It wasn’t far to Coquina Beacb and my husband enjoyed the walking/running path there. The condo was well appointed for our group of 4 people and would easily fit three couples. The extra beach umbrellas you can rent from Ammey were so convenient. There were plenty of chairs and beach toys. I would definitely stay here again on my next trip to AMi.

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.

Chambre 303-Great Beachfront Condo!
Amazing place right on the beach and walking distance to John’s Pass. Everything was just as advertised. Plenty of space and awesome view of the ocean from the balcony (the high Adirondack chairs on the balcony added a good touch and made for easy viewing). Easy beach access. Clean, Furnished nicely, and bed was comfortable. Has everything you’ll need for a fun relaxing vacation. We’ll be back!

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

Ocean Front Beach Condo Gap Day Special 6/12-6/20!
We had a lovely stay at 42 Gulf Blvd IRB! The house is comfortable, the beach area is peaceful and beautiful, and the location is perfect for a relaxing getaway. While we did experience a couple of issues during our stay, we truly appreciate how responsive and caring the management team was. They took our concerns seriously and handled the situation with professionalism and kindness. Their communication made all the difference. We would absolutely stay here again and highly recommend it to others looking for a laid-back and enjoyable beach experience!
Quick stats about waterfront rentals in Longboat Key
Total rentals
240 properties
Nightly prices starting at
$83 NZD 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