Beachfront holiday rentals in Siesta Key

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Popular amenities for beachfront rentals in Siesta Key

Pet-friendly beachfront home rentals

Top guest favourite
Flat in Venice
4.98 out of 5 average rating, 63 reviews

Venice Island Pool Casita with 2Bedrooms/2 Baths

MarkRating, 5 stars3 weeks ago
Our 2nd stay and had a wonderful time! Thanks so much!
Guest favourite
Home in Holmes Beach
5 out of 5 average rating, 13 reviews

Beachy Blue by Beach Boutique Rentals

BrentRating, 5 stars3 weeks ago
The beachy blue home was a great vacation home for my family. The location was perfect. A short walk or golf cart ride to the beach with plenty of spots to park. The beach location was also wonderful as it was not as crowded as other locations we have stayed in the past. The pool was a great oasis for my kids and the spa was a great surprise. It was warm enough to sit in during cool nights and still use during the day to relax. We had a party of 8 and the setup of the house was perfect with rooms, beds and bathrooms. We would absolutely rent here again.
Guest favourite
Flat in Holmes Beach
4.97 out of 5 average rating, 38 reviews

Luxury 2BD Oceanfront Condo + Private Parking

JohnRating, 5 stars3 days ago
Our family of 5 loved Akira's place. It felt very private as the store below is very low traffic. The beach access right across the street was perfect for us and the cooler, chairs and umbrella in the unit were a great to have! Short walk to many restaurants and a trolly stop right across the street made getting around easy. We had a great time!
Guest favourite
Cottage in Pass-a-Grille Beach
4.87 out of 5 average rating, 166 reviews

BEACH! Sunny Escape! Steps 2 Famous Beach w/2 Bike

CindyRating, 5 stars3 months ago
If you are looking for a historic, old-school Florida home, this is it. The only reason it isn’t a perfect score is that the hurricane closed most of the shops that make Pass-a-Grille quaint. We were able to support a few local restaurants, and the local traffic was very light. We wouldn’t have changed our trip, but it would have been good to know. It seems like businesses are working hard to get back on their feet. Overall a good experience. I appreciate Lisa’s great responsiveness.
Superhost
Home in Sarasota
5 out of 5 average rating, 3 reviews

Casa Antilles | Luxury Home Steps To Beach!

MichaelRating, 5 stars12 months ago
The Cottages were great hosts. The place had all the accommodations needed to make us feel right at home. Everything was clean and well kept. We particularly appreciated how stocked the house was, plenty of beach/pool towels, beach equipment (chairs, wagon), and all the other amenities we expected. The elevator is a great touch. I never thought we would need/want one, but with kids, beach gear, groceries, etc. it made a huge difference. We didn’t need much during our stay, but when we reached out, the host was very responsive. Overall, a great location, great house, and excellent host. Highly recommended.
Superhost
Home in Anna Maria
4.73 out of 5 average rating, 134 reviews

MAY Specials, Beachfront, Private Beach, Dogs ok

NathanRating, 5 stars3 weeks ago
Stunning views, great space and the water for swimming is perfect for small children. The shallow water extends very far from the beach and they loved playing!!
Guest favourite
Flat in Pass-a-Grille Beach
4.99 out of 5 average rating, 112 reviews

202 Beautiful Pass a Grille Steps from Beach

ParmeleeRating, 5 stars1 month ago
What an enjoyable visit to Passé Grill. Not only was our stay at the Berkeley beach club exactly what we needed but it was a perfect location! The amenities were also unexpected and amazing. Would highly recommend this spot and Maryann who was very responsive. Thank you for a great vacation!!
Guest favourite
Flat in Pass-a-Grille Beach
4.93 out of 5 average rating, 41 reviews

Historic Downtown Pass A Grille Beach Pool WiFi

LauraRating, 5 stars4 days ago
Idyllic location—private, peaceful, and next to cute shops and a beautiful beach. House was relaxing, clean, and refreshingly minimalist in decor. Brandon was very responsive to any communication—the whole experience was easy breezy. I’d book again!

Beachfront home rentals with a pool

Superhost
Home in Siesta Key
4.77 out of 5 average rating, 52 reviews

Sun-Soaked & Relaxing Gem ~ Steps to Beach ~ Pool!

AnnieRating, 5 stars1 month ago
Our family of 5 enjoyed our stay. The pros were being able to walk to the beach through private gate access, anything we needed for the beach was provided including toys for kids, home had all the necessities, and the kids enjoyed the pool when we needed a break from the beach. A few cons would be because there is a lot of construction going on down this road (including the bottom units) we could hear work trucks in the mornings which disrupted any plans to sleep in, the bed in the primary room also had dips in it, and one of two dryers on-site did not work so when we started 2 different wash loads we had to wait for one load to finish before drying the other (not a huge deal but it was unexpected, could also cause an issue if there were other units trying to wash/dry at the same time). Overall the place is as described and our family was comfortable. I’d recommend this place to others.
Superhost
Flat in Sarasota
4.83 out of 5 average rating, 221 reviews

VILLA 5 · Pool view. King bed. Daily rentals

Alejandro Rating, 5 stars7 months ago
Second time here. Great place to stay for couple nights. Short walk to beach. Peaceful and quiet.
Guest favourite
Home in Holmes Beach
4.95 out of 5 average rating, 103 reviews

The Peachy Beach House, steps to the gulf

AnaRating, 5 stars1 month ago
We had an amazing vacation! Perfect location and great amenities. Our daughter had a blast in the pool. Sunsets were perfect. Waking up to the view of the water every morning was beautiful
Guest favourite
Home in Anna Maria
4.92 out of 5 average rating, 13 reviews

Ocean Air Oasis-New Centrally Located AMI Luxury

WillRating, 5 stars2 weeks ago
Our spring break getaway to Anna Maria Island was made more enjoyable by our stay here. This wasn't just a place to sleep; it truly felt like a refuge for our party of five. While we loved spending quality time together at Bean Point Beach and around the pool, the thoughtful layout of the house provided several private spaces that allowed us to enjoy much-needed 'me time' throughout the vacation. This balance of togetherness and individual space was a real highlight and contributed significantly to a relaxing trip. With its impressive ceilings, the house boasted a sense of spaciousness that was visually appealing. The high-end finishes in the kitchen and bathrooms, along with the beautiful flooring and trim made us feel we were somewhere special. This, combined with the unique layout, created an environment that was visually appealing and incredibly welcoming. We connected with Jay several times, and his response time and actions were always fast and appropriate. Would recommend.
Guest favourite
Apartment in Siesta Key
4.82 out of 5 average rating, 313 reviews

[Beach Elements] pool view + private beach & bikes

MichelleRating, 5 stars7 months ago
The place was really comfy and jayme was very helpful and friendly with my questions. 100% recommended
Superhost
Home in Holmes Beach
4.86 out of 5 average rating, 43 reviews

Cozy beach house with pool - 1 block from beach!

SarahRating, 5 stars3 weeks ago
Great location across from Manatee Beach, Publix grocery store. Enjoyed that homer equipped with ping pong, bags and other games.
Superhost
Home in Nokomis
5 out of 5 average rating, 3 reviews

Waterfront! Lyons Bay Delight! Walk to Beaches!

AngelRating, 5 stars1 month ago
Great location on the bay with a quick walk to the beach. House is very spacious and comfortable. We loved everything about it. The host, Kathy, was very responsive and made the whole process easy. Can’t wait to come back
Superhost
Townhouse in Siesta Key
4.77 out of 5 average rating, 181 reviews

Siesta Key Beach House with Private Beach Access

JacobRating, 5 stars8 months ago
Great location, minutes from the private beach access. Excellent accomodations, great house. Great area.

Private beachfront home rentals

Top guest favourite
Home in Bradenton Beach
5 out of 5 average rating, 62 reviews

Beach front! Sunsets + Bridge Street+ Restaurants!

AmyRating, 5 stars2 days ago
We loved this beach house! Great location, sunsets, clean, well appointed and beautiful. We would definitely come back!
Top guest favourite
Apartment in Nokomis
5 out of 5 average rating, 23 reviews

Private Waterfront 2 Bedroom Condo

JillRating, 5 stars2 weeks ago
My daughters & I stayed in Nokomis for a spring break beach trip. Dan's place was exactly as described in the listing. The entire place was clean and tastefully decorated. It had everything we needed for our stay. We used the paddle boards and kayaks during our stay, as well as the beach chairs & umbrella. It was so nice to have everything for the beach available for us to borrow. Nokomis Beach is only a few minutes from the condo. We enjoyed several short trips to Venice for restaurants and coffee shops. Dan responded quickly to any questions I sent. We had an excellent stay at Dan's and would definitely stay there again!
Superhost
Apartment in Longboat Key
4.86 out of 5 average rating, 29 reviews

3 BR Condo On Longboat Key Beach and Waterfront

DaveRating, 5 stars2 months ago
This place was wonderful, Peaceful,quiet,private beach , everything described in listing. I would definitely stay here again! The view was picture perfect! Location was everything you would want .
Top guest favourite
Flat in Longboat Key
5 out of 5 average rating, 22 reviews

Turquoise Gem 1st Floor

KarenRating, 5 stars3 weeks ago
John was a great host. He answered all of my questions before and during our trip in a timely manner. The place was cozy and comfortable. It was really quiet and great for sleeping. We enjoyed the use of the kitchen and absolutely loved sitting outside in our private patio whether enjoying morning coffee or a nice glass of wine before dinner. There was a lot to do within walking distance (beach of course!, park, local shops and restaurants) or a quick drive away. We took advantage of many of John's recommendations. Longboat key is a special place and we'd certainly love to return some day. Thank you!
Superhost
Home in Sarasota
4.89 out of 5 average rating, 92 reviews

Renovated Beachhouse Private Beach Access, Unit S

PeytonRating, 5 stars9 months ago
Sheryl’s responsiveness and care for us was unmatched. We had an issue with the property that she resolved immediately and even called me personally to make sure my friends and I were taken care of. Great location and outstanding customer service.
Superhost
Home in Longboat Key
4.88 out of 5 average rating, 120 reviews

Summer House longboat key

AndreaRating, 5 stars2 weeks ago
We had a wonderful stay at Chris’s house on longboat key! The pool was so nice for the kids and us adults to swim and relax by. The house was very nice and the beds were very comfortable. There were plenty of towels, extra sheets, and the kitchen was very well stocked with pot and pans. We did find it easier to drive closer to the crosswalk to the beach and park before walking across the street to get to the beach access. The beach was very quiet and beautiful. We found so many shells and our kids loved doing evening swims at sunset! It’s a very quick drive to Anna Maria Island and St Armand’s Circle. We really enjoyed our stay.
Top guest favourite
Home in Englewood
5 out of 5 average rating, 9 reviews

Manasota Key to Relaxation

TravisRating, 5 stars1 month ago
Linda’s home was truly a gem! So peaceful and relaxing! The ocean is literally steps away, with sunsets, swimming, sand, shells and shark’s teeth to hunt all day long!! We had everything we needed to feel at home, and more! Manasota Key was amazing and Linda’s home was a perfect location for our family’s get away!
Superhost
Home in Anna Maria
4.87 out of 5 average rating, 15 reviews

The Beach House 2 by Duncan Real Estate

BeckyRating, 5 stars6 months ago
This home was so perfect for our beach vacation, we especially liked the covered porch facing the beach with the big gum tree in front of it. All the amenities were provided, we had a grill to enjoy, so comfortable. We will definitely be back to enjoy it more!

Quick stats about beachfront rentals in Siesta Key

  • Total rentals

    170 properties

  • Nightly prices starting at

    £90 before taxes and fees

  • Total number of reviews

    6.7K reviews

  • Family-friendly rentals

    130 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with a pool

    140 properties have a pool

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