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Waterfront holiday rentals in Longboat Key

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Popular amenities for waterfront rentals in Longboat Key

Waterfront apartment rentals

Guest favourite
Flat in Bradenton Beach
4.9 out of 5 average rating, 126 reviews

Newly Remodeled Beachfront Studio - On the sand!

AnnetteRating, 5 stars1 week ago
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.
Guest favourite
Flat in Bradenton Beach
4.88 out of 5 average rating, 223 reviews

Las Palmas Beach Rentals Unit 1

AlainRating, 5 stars4 days ago
excellent location, everything super clean, thank you for everything
Superhost
Flat in Siesta Key
4.84 out of 5 average rating, 253 reviews

Siesta Key - Poolside Suite - Studio - Free kayaks

JessicaRating, 5 stars3 weeks ago
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!
Top guest favourite
Flat in Independence Square
4.96 out of 5 average rating, 162 reviews

Direct Ocean View Top Floor Renovated. 2BR, 2 Bath

AdrianneRating, 5 stars5 days ago
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!
Top guest favourite
Flat in Treasure Island
4.99 out of 5 average rating, 104 reviews

Popular Beachside Studio w/ Shady Patio & Palms!

MasonRating, 5 stars1 week ago
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!
Guest favourite
Flat in Siesta Key
4.93 out of 5 average rating, 108 reviews

Siesta Premier Location - The 'Calm of Siesta'

JasminRating, 5 stars3 weeks ago
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.
Guest favourite
Flat in Sarasota
4.85 out of 5 average rating, 134 reviews

The Coastal Nest w/King Bed

PaulaRating, 5 stars3 days ago
Great place to stay with a great view! Very nice restaurant within walking distance too.
Guest favourite
Flat in Clearwater Beach
4.87 out of 5 average rating, 126 reviews

Waterfront Coastal Condo 2 Blocks to Beach

LeahRating, 5 stars3 weeks ago
We had a great time staying here. I caught myself saying that every time I’m in town, I’d try to stay here. Waking up and sitting by the dock with some coffee was pretty great. The guys working the office and the water sports were very nice also. Definitely recommend staying here for small groups!

Waterfront house rentals

Top guest favourite
Home in Anna Maria
5 out of 5 average rating, 36 reviews

Veselka - Canal front w private heated pool & dock

CarrieRating, 5 stars1 week ago
We had an amazing week at Michael and Denzel’s home! It was actually better than the pictures with enough space for everyone to feel right at home. The layout was perfect for two families. The home is spotless and extremely well stocked. The island is beautiful and we enjoyed the pool everyday! Highly recommend this home. It will exceed your expectations in every way!
Top guest favourite
Home in Bradenton
5 out of 5 average rating, 75 reviews

Heated Pool-Game Room-EV-Near AMI Beaches/IMG!

AlexRating, 5 stars2 weeks ago
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!
Superhost
Home in Bradenton
4.83 out of 5 average rating, 6 reviews

"Enfuego!"

AlisonRating, 5 stars5 days ago
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.
Guest favourite
Home in Longboat Key
5 out of 5 average rating, 23 reviews

North Shore Six

PJRating, 5 stars9 months ago
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!
Top guest favourite
Home in Anna Maria
4.94 out of 5 average rating, 177 reviews

Discount 33% June 3-Day and July 4-Day w/Dock-Pool

AlfredoRating, 5 stars1 week ago
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!!
Guest favourite
Home in Bradenton Beach
4.96 out of 5 average rating, 105 reviews

Canal-Front Retreat w/ Pool, Dock & Beach Access

BrianRating, 5 stars1 month ago
This place was great! Would stay here again. Easy walking distance to the beach. Would recommend this place to anyone.
Top guest favourite
Home in Apollo Beach
4.94 out of 5 average rating, 111 reviews

Apollo Beach Waterfront Amazing PoolOasis w kayaks

DavidRating, 5 stars1 day ago
This was the perfect place for a nice, peaceful long weekend. The house was perfect. Spacious and extremely clean, the pool was perfect and a nice was to relax after a day of outside activities. Love the tv on the back porch. Our last day we fished off the dock then grilled and hung out in the pool while watching a movie. It was so relaxing. Fishing was good as long as you had an outgoing on incoming tide. Caught a variety including trout. Publix and everything else you need is literally a couple miles away, but you are still in a very quiet neighborhood. The hosts were amazing. I’ve never had host respond as quick as these hosts did. They weee very helpful. The first pan is to stay here again and this time bring a boat with us. I can’t think of one negative thing to say. Everything was perfect!!
Superhost
Home in Anna Maria
5 out of 5 average rating, 4 reviews

Beach a la Mode | Luxury Anna Maria Island Home!

LindaRating, 5 stars1 month ago
First time to AMI and it did not disappoint! The island is so cute, the beaches/water are amazing, and this house was the icing on the cake!!! JUST WOW! This house is just GORGEOUS! It’s so private, the landscaping is so beautiful you feel like you’re in the jungle. Very spacious, beautiful layout, the decor is so cute in every space. Such an awesome kitchen, balconies are so nice! Great game room, we played pool every night. The rooftop is SO COOL, the 360 degree view of the island is unreal. Watched both the sunrise and sunset, highly recommend! Pool and hot tub were so nice with plenty of shade. Loved all the spaces to sit on the pool deck and the dock/being on the canal was so nice. We saw so many birds including a wild turkey and even had daily visits from a raccoon who came to drink from the pool! We took advantage of the kayaks and paddled the inlets and even saw manatee. Honestly this place is so magical we had the best stay and we didn’t want to leave. Hope to return again!

Waterfront apartment rentals

Guest favourite
Apartment in Indian Shores
4.93 out of 5 average rating, 136 reviews

"Jewel At The Shores" Gulf Front, sleeps 5

DerekRating, 5 stars2 weeks ago
Excellent location! Everything you need is in the condo. Hope to come back soon!
Top guest favourite
Apartment in Siesta Key
4.97 out of 5 average rating, 319 reviews

On the Beach; Siesta Key SunBum Studio

LauraRating, 5 stars1 week ago
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!
Guest favourite
Apartment in Madeira Beach
4.92 out of 5 average rating, 13 reviews

Chambre 303-Great Beachfront Condo!

JosephRating, 5 stars3 weeks ago
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!
Top guest favourite
Apartment in Treasure Island
4.99 out of 5 average rating, 188 reviews

Spectacular beach to bay views from this resort.

LaraRating, 5 stars1 week ago
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
Superhost
Apartment in Treasure Island
4.85 out of 5 average rating, 150 reviews

King Oceanfront Suite! Kitchenette + Balcony!

ChrisRating, 5 stars1 day ago
We enjoyed our stay at the Island Inn. The staff was very friendly and the host was quick to respond to our questions. We liked the view from the room and that we were right on the beach. It was helpful having beach chairs and umbrellas to use so we didn't have to pay for them everyday. I think it was great for 2 adult guests, any more than that and the space might start feeling a little cramped. We used the grills outside to cook as well as the hot plates so we were able to make whatever we wanted. Great view of the sunset from the building, we watched the sun go down from the balcony and beach, very peaceful at night. Overall a great stay!
Guest favourite
Apartment in Indian Rocks Beach
4.83 out of 5 average rating, 106 reviews

Ocean Front Beach Condo Gap Day Special 6/12-6/20!

MohammedRating, 5 stars1 month ago
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!
Guest favourite
Apartment in Treasure Island
4.92 out of 5 average rating, 131 reviews

Beachfront 2/2 Condo on Treasure Island, 305W Ocea

AprilRating, 5 stars6 days ago
This condo was absolutely beautiful!! So clean and very accommodating!! It had an amazing closet full of beach accessories!! We love places like this because we usually fly down and it’s so helpful to have things to take to the beach without having to buy it. We would hands down recommend this place over and over and we hope to return in the future!
Top guest favourite
Apartment in Treasure Island
4.98 out of 5 average rating, 125 reviews

Beach, dolphin/manatee sightings, fishing, sunset

KaitlynRating, 5 stars2 weeks ago
Love, love, love this place! Becky and Tyler were super sweet and very responsive! Check-in was smooth, the place was beautiful and comfortable! This is definitely one of our most favorite vacations that we have been on!

Quick stats about waterfront rentals in Longboat Key

  • Total rentals

    240 properties

  • Nightly prices starting at

    $64 SGD 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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