
Waterfront vacation rentals in Longboat Key
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Top-rated waterfront rentals in Longboat Key
Guests agree: these waterfront rentals are highly rated for location, cleanliness, and more.
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Popular amenities for Longboat Key waterfront rentals
Waterfront apartment rentals

B⎈AT HOUSE OASIS⚓Steps to the water⚓Walk to Beach!
Perfect, quiet location on the water. Close to beach and night life. Room was comfortable, clean, and well stocked. Will book here again

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
Cute as a button! Super homie! Steps to the beach! Had everything we needed. The place was just as described and walkable to almost everything. Great location! Fabulous house! We will definitely be coming back to stay with Debra. The sunroom is absolutely the best spot in the house!

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!

Direct Ocean View Top Floor Renovated. 2BR, 2 Bath
Perfection! Scott was such a responsive and accommodating host. Scott knew we had an early flight, and he let us check in as soon as their place was ready. Scott even made sure there was a pack n play for our little one, which exceeded our expectations. The location directly on the beach made sunsets after a busy day so relaxing. We got to see a lot of seabirds and dolphins right from the balcony. Everything we needed was there. The place was very clean throughout with a fully functioning kitchen and all necessary beach supplies. We made unforgettable memories for our first Florida family vacation, and we could not have asked for a better location with the best host. Thank you so much!

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!

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.

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!
Waterfront house rentals

Your DreamOasisAwaits: SiestaKeyEscape with Pool!
A beautiful home with a private, relaxed atmosphere and all the amenities you could need.

Mins to Beach + IMG+ Hot tub + Heated Pool!
Ashley’s place was amazing. It was thoughtfully stocked and had everything we needed from linens to sunscreen. The home was spotless and Ashley was very attentive during our stay. Me and my family would definitely visit again!!

Veselka - Canal front w private heated pool & dock
We had a fantastic time at Michael and Denzil’s place! This was our second time in AMI. We stayed for a week with 6 adults and a toddler and had more than enough space for everyone to have their own room and not feel like we were on top of each other either. The home is very comfortable, clean, and has lots of natural light. We loved that each bedroom had its own bathroom and that we were walking distance to the beach (which wasn’t very busy, it felt private). We loved the pool and backing on to the lagoon too - we did a little fishing and went for a swim everyday. We really appreciated getting a 1:00 PM check in as we were coming in from the airport with a toddler due for a nap! We would 100% book with Michael and Denzil again, we love AMI! Thank you so much!

Heated Pool-Game Room-EV-Near AMI Beaches/IMG!
Just checked out of Kate’s place! What can we say, as a family of five and also our parents we had the most amazing stay. The property is as described, super clean and spacious! The kids loved the pool area and spend countless hours playing around the pool and with the vast array of games throughout the villa. The Area was beautiful, gorgeous beaches and friendly people! Kate was an amazing host, always insightful, friendly and very responsive. What a fabulous family holiday full of lots of new memories created. Thanks Kate!

Coastal Retreat near Siesta Key Beach and Downtown
Aubrey’s place is amazing! It’s in a great location close to the best attractions Sarasota has to offer, but you’ll find yourself just wanting to stay inside and enjoy this masterfully decorated space. I cannot exaggerate the fact that it feels like you are stepping into a page in an interior design magazine. Aubrey herself was delightful to communicate with. She left us a very sweet welcome note and little gift. Wish she had a bnb in every town we visit!

"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!

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!

༄ Sunset Shore on Anna Maria Island ༄
First time visit to AMI & it was beyond amazing. The house was so clean & just as described. Outdoor space had fantastic ambiance & plenty of space for a family of 7. Had some other family vacationing there as well, and they spent the whole time at our house because they said it was 1000 times better than where they were staying. Owners were so friendly, quick to respond & just overall welcoming & accommodating. Highly recommend staying here!!
Waterfront condo rentals

ON THE BEACH Condo, SPA -1 bd/1 ba. Location!
The place was exactly as advertised and I loved how close we were to the beach. It also was pretty private and the beach wasn’t crowded at all. Even though it was great, we probably wouldn’t stay here again because of the shower. My bf has had knee surgery and it was extremely difficult to get into the shower. The side of the tub was very very high, I had to lift my knee to my chest to get into the tub and my bf struggled a lot with his bad knee to do that to get into the shower. I still give the place 5 stars because it was as advertised I just didn’t realize from photos that the bathroom would be difficult for us to manage, and that’s our personal problem not a problem with the Airbnb. Everything else was perfect!

"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
This is our 5th time staying here, and the place and location speak for itself. The one thing that takes this place over the top in our opinion is the amazing and friendly hosts, Honestly they have treated us like family and made sure our stay has been amazing and safe. We were there for hurricane Helene and they made sure we were taken care of the whole time. I can’t thank them enough, including Vince who is always on top of everything. Thank you from the bottom of my heart.

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.

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 at the Westwind was great. Very clean and up to date amenities. Had everything you need to head to the beach including beach chairs, coolers, and towels. Everything was very positive. Just as described and pictured.

Sea Side Sunsets Unit C
Astonishing view from the balcony. Clean and well equipped place. The only downside is the living TV was not working the whole time during our stay. Other than that, perfect

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
G$10,457 GYD 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
- 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