Beachfront vacation rentals in Siesta Key

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Popular amenities for Siesta Key beachfront rentals

Pet-friendly beachfront home rentals

Top guest favourite
Apartment 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 stars1 month 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.
Top guest favourite
Home in Longboat Key
4.96 out of 5 average rating, 76 reviews

Beautiful Beach House

LaurentRating, 5 stars1 week ago
It is the second time we come to Randy and Charlotta’s wonderful place. And we will make it three ! Just perfection .
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 stars4 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
Apartment in Englewood
4.8 out of 5 average rating, 15 reviews

Updated w/ Private Beach Access Heron's Walk #3

ScottRating, 5 stars2 months ago
Awesome location, located right in between the Gulf and bay! The unit was nicely remodeled, had comfortable furniture and had a beachy vibe. Englewood was hit pretty hard by 2 hurricanes recently, so things are not back to normal, including the deeded beach access and bay access. We're also hosts in Englewood, so we're very understanding of that and it didn't stop us from enjoying the place!
Superhost
Townhouse in Sunset Beach
4.82 out of 5 average rating, 50 reviews

Beach Haven B4 Secluded Beachfront Striking Views

AlanRating, 5 stars2 months ago
We had a great time, Home was very nice and spacious, beach right in front of the house, sunsets were beautiful, beds were very comfortable they had everything that we needed, would definitely stay there again no problems Thanks again Alan and Susan Mohn
Guest favourite
Apartment in Pass-a-Grille Beach
4.93 out of 5 average rating, 41 reviews

Historic Downtown Pass A Grille Beach Pool WiFi

LauraRating, 5 stars1 week 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!
Guest favourite
Home in Englewood
4.9 out of 5 average rating, 30 reviews

Quaint Surf Cottage on Beach - Hurricane Milton!

SinaRating, 5 stars6 months ago
Dear Jeff Thanks for hosting us. Even though the hurrican helene hit this area so hard, you made us feel safe and at home! We enjoyed the lonely beach walks and collecting sea shells. The neighbourhood is extremely friendly. Especially Matt and Peppy. They were always there for a nice chat or a helping hand (our car ran out of battery). We enjoyed every second of our stay! Thanks so much for everything and we hope to come back one day, or maybe you visit us in switzerland :) Greeting Florian & Sina

Beachfront home rentals with a pool

Top guest favourite
Home in Anna Maria
5 out of 5 average rating, 11 reviews

The Toasty Coconut

GaryRating, 5 stars3 weeks ago
This home is perfectly located for all beach and ocean activity. It was extremely convenient to our activities. It is located in a quiet neighborhood and yet an easy walk to many activities, restaurants, shopping. The interior of the home has been freshly done and was easy to use. The pool was especially perfect for our family’s use. It was a delightful home in all regards.
Superhost
Home in Siesta Key
4.77 out of 5 average rating, 53 reviews

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

ScottRating, 5 stars1 week ago
We really enjoyed our stay. It's a very short walk to the beach, and the beach is one of the nicest we've been to in Florida. Steve was a great communicator and very responsive. The property is very convenient to restaurants and what-not. I would highly recommend.
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
Superhost
Home in Siesta Key
4.8 out of 5 average rating, 103 reviews

Trendy & Fun Haven: Walk to Beach ~ Jacuzzi ~ Pool

SarahRating, 5 stars1 day ago
We were a group of 7 girls and had a blast at Chads place! Any issues we had were addressed and handled within MOMENTS. Home was clean, safe ash to locate, easy to get into and accurately described. House was within walking distance of everything we wanted to do (beach, bars, restaurants). We all agree we’ll return again!
Guest favourite
Apartment in Sunset Beach
4.88 out of 5 average rating, 16 reviews

Summer Beach Penthouse w/ Ocean View + Pool #613

ZelectraRating, 5 stars8 months ago
There was four of us who went on this trip. We had a WONDERFUL TIME. We loved our condo and the location. We went e-bike riding, Kyacking, Boating, Jet Sking and Comedy Clubs. We had dinners galore! And everthing was so close to our condo. I would sugest this place to anyone! We had a blast! But more importantly, Dave took great care of us! He checked in on us to make sure we were okay. And even bought or group a bottle of Tiquilla! He was so nice. The condo was beautiful and has absolutely everything you could possibly need on a trip. We plan to stay there again in the future. I really cant say enough about this place. We had a great time.
Top guest favourite
Home in Bradenton Beach
5 out of 5 average rating, 17 reviews

Sunset View

KarlaRating, 5 stars2 weeks ago
We had a wonderful time. The house was more spacious than pictures shown. Location was amazing!
Guest favourite
Home in Nokomis
4.83 out of 5 average rating, 6 reviews

Waterfront! Lyons Bay Delight! Walk to Beaches!

KevinRating, 5 stars1 week ago
We loved staying at this home! The location was perfect for our needs. It was an extremely easy walk to the restaurants and the beach. It was even manageable for our 5 year old who loved the walks. Waking up and having a morning coffee looking out over Lyons Bay was so peaceful. We would definitely stay here again.
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 Sunset Beach
5 out of 5 average rating, 39 reviews

Luxury Waterfront Sunset Beach

AlisonRating, 5 stars3 weeks ago
This house was perfect for our spring break mother daughter trip. The morning sunrise over the bay with a Nespresso coffee on the deck couldn’t be beat! The walk to the beach is so quick and easy and it was nice to be able to use the lounge chairs and bar/food service at Caddy’s. The sunsets from the beach are amazing. The house was clean and beds were comfortable. It was nice having three bathrooms and a beautiful kitchen. There is a bedroom on the main floor for guests who may have issues going up the spiral staircase with luggage. Priscilla was so friendly, accommodating and very quick to respond.
Superhost
Condo 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
Apartment in Longboat Key
5 out of 5 average rating, 23 reviews

Turquoise Gem 1st Floor

BrookeRating, 5 stars1 week ago
We really enjoyed our stay! The hosts were helpful and the place was super clean.
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, 121 reviews

Summer House longboat key

DaneRating, 5 stars3 days ago
Chris was a very responsive host. During our stay he spent a day working on his boat in the back. He was very friendly, but also respected our privacy. The house met all of our expectations and our kids loved the pool. The neighborhood was great to walk through and each house offered fantastic curb appeal. With 3 kids under the age of 6, the 10-12 minute walk to the beach was a little long, but Chris’ wagon and beach supplies helped! The golf cart would have been ideal, but without a place to park near the beach we didn’t have much use for it. We thoroughly enjoyed our stay and the entire family agrees we’d love to go back. Thanks Chris!
Guest favourite
Condo 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
Guest favourite
Vacation home in Englewood
4.93 out of 5 average rating, 42 reviews

Ocean view, Totally remodeled, Beach Home!

AmyRating, 5 stars3 weeks ago
Our family had an incredible vacation. This location in Florida is amazing, so peaceful, quiet and authentic.
Top guest favourite
Home in Englewood
5 out of 5 average rating, 10 reviews

Manasota Key to Relaxation

ConnieRating, 5 stars3 days ago
Our stay at Linda's was fantastic. The house is very spacious. The bedrooms and large and the beds are super comfortable. Everything was clean and fully stocked with all the necessities from extra towels, beach chairs and beach accessories. The view is unforgettable. Everything you need is there. Groceries and restaurants are an easy drive. Linda was responsive and lovely to speak with. My favorite Manasota key rental yet!

Quick stats about beachfront rentals in Siesta Key

  • Total rentals

    170 properties

  • Nightly prices starting at

    $166 CAD 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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