Beachfront vacation rentals in Siesta Key

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Popular amenities for Siesta Key beachfront rentals

Beachfront home rentals with a pool

Superhost
An aerial view showcases a modern retreat surrounded by lush palm trees. The well-maintained landscaping features white stones and vibrant greenery. A heated swimming pool is visible, enhancing the outdoor space, with the quadplex and parking area in the background under soft evening light.
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
A shared pool area is surrounded by vibrant blue walls and tropical greenery. Lounge chairs in various colors are arranged around the pool, inviting relaxation. Bright sunlight reflects off the water's surface, enhancing the welcoming atmosphere of this outdoor space.
Apartment 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 favorite
A private heated pool is featured in a landscaped outdoor area, surrounded by smooth stone tiles. Colorful plants add vibrancy to the space, while a flowing water feature enhances the serene atmosphere.
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
Top guest favorite
A beautifully landscaped outdoor area features a private saltwater pool surrounded by light-colored pavers. Chaise loungers are positioned nearby, and vibrant tropical plants provide greenery against the blue exterior of the home.
Home in Anna Maria
5 out of 5 average rating, 14 reviews

Bliss by the Beach by Beach Boutique Rentals

DennisRating, 5 stars8 months ago
It was perfect for us. Colors were my fiance favorite shade of light blues. Cozy and comfortable with easy access to beautiful Bean Point Beach. Pool is perfect size for two to lounge on the deck or in the water and, soak up the sun and dip in the water to cool off. We look forward to staying there again. We were engaged on Bean Point Beach and celebrated our engagement with family and friends in the boutique. Love it!
Guest favorite
A clear view of one of the community heated pools is presented, featuring a spacious area surrounded by palm trees. The pool's depth is marked as 3 feet 7 inches, with lounge chairs placed around its perimeter for relaxation.
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
Top guest favorite
A serene pool area is surrounded by lush greenery and swaying palm trees. Two blue chairs and an umbrella provide shade, while four lounge chairs line the poolside. The inviting water reflects the sky above, creating a peaceful outdoor retreat.
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!
Superhost
A spacious lawn surrounds a single-story house with a screened-in pool area. The exterior features a red-tiled roof and large windows, allowing ample natural light. Lush green grass extends towards the tree line, creating a serene outdoor environment with clear blue skies and scattered clouds.
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
A heated swimming pool is surrounded by palm trees and lounge chairs, providing a relaxing outdoor space. Colorful umbrellas offer shade, and the pool is set against a backdrop of landscaped greenery and a sign indicating the property name.
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.

Beachfront home rentals with a hot tub

Superhost
Condo in Bradenton Beach
4.7 out of 5 average rating, 10 reviews

ON THE BEACH Condo, SPA -1 bd/1 ba. Location!

PaulRating, 5 stars2 months ago
Peaceful, accommodating, views were spectacular and we really couldn’t ask for more out of a place to get and enjoy for a few days. We will be back for sure.
Superhost
A sparkling saltwater pool is surrounded by tropical landscaping, featuring palm trees and manicured hedges. Lounge chairs and a glass-topped table provide comfortable seating options. A spiral staircase leads to an upper level, enhancing the outdoor space's accessibility and charm.
Apartment in Bradenton
4.81 out of 5 average rating, 16 reviews

Luxury Bayview Retreat w/Pool, Spa+ Hot Tub

MarkRating, 5 stars2 months ago
Len was a terrific host, and his property is beautiful and exactly as described. Len made us feel right at home from the moment we arrived, and was very responsive to any of our text communications. the property is exactly as described and perhaps better than the photos on the listing, including a beautiful view of the water with stellar sunrises every morning. the location is quiet and centrally located to great restaurants and beaches on longboat or siesta key. highly recommend this location for any travelers looking for a quiet and comfortable stay in the Sarasota area.
Superhost
Home in Bradenton Beach
4.77 out of 5 average rating, 13 reviews

AMI Bridge Street Pier Phase Inn

JasonRating, 5 stars8 months ago
Excellent location! Clean. Rex was very responsive. This is the perfect place for a nice getaway - not big or "luxury" quality, but you just can't beat the location and it has any basic amenity you need. Once you unload and park, you won't need a vehicle. You can walk around Bridge Street, walk to the beach, or take the trolley to the north part of the island.
Top guest favorite
Condo in Siesta Key
4.96 out of 5 average rating, 312 reviews

On the Beach; Siesta Key SunBum Studio

BrendaRating, 5 stars4 days ago
We had a wonderful time! Tim and Stephanie’s place is a hidden gem at Siesta Key. Everything we could possibly have needed was provided. Being steps from the beach was super convenient. The decor and setup were very much up to date. Even the property manager said we had the best unit in the entire club! We totally recommend Tim and Stephanie’s place.
Guest favorite
Island in Sarasota
4.97 out of 5 average rating, 322 reviews

NEW MAY SALE Openings! Sarasota #1 Lux BEACH Villa

KatieRating, 5 stars1 month ago
We just enjoyed five days there with three young kids. Beautiful place, awesome communication and accommodating to all of our needs! Thank you for a great stay!!
Guest favorite
An inviting living space features a light-colored sofa with decorative cushions, a dining area with a table and chairs, and sliding glass doors that open to a stunning view of the beach and water. Natural light fills the room, complementing the home’s neutral palette.
Condo in Bradenton Beach
4.9 out of 5 average rating, 42 reviews

Gorgeous Gulf Views - Beachfront 2BR/2B Condo

LucyRating, 5 stars1 week ago
Absolutely stunning property. We loved every second of our 5 day stay, and were devastated to leave! You couldn’t ask for a better location, the stunning sea views surround you and the beach is right on the doorstep. The property has everything you could need, including a well stocked kitchen and heaps of beach supplies. The pool is wonderful as well! Lots of shops, bars and restaurants within a short walk, but far enough away to feel nice and quiet. I can’t recommend it enough!
Guest favorite
The outdoor area features a spacious pool and a separate spa, surrounded by manicured gardens and palm trees. A covered lanai with steps leads to the upper level of the home, which includes expansive sliding glass doors inviting natural light into the interior.
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.
Top guest favorite
A bright living area features comfortable seating and a light blue color scheme. Large windows provide views of the beach and turquoise waves. The space includes a dining counter with stools and a TV mounted on a wooden cabinet, enhancing the room's open and airy feel.
Condo in Bradenton Beach
4.99 out of 5 average rating, 129 reviews

★Right on the beach ★ Relax and Enjoy ♥ Sunsets!

LisaRating, 5 stars1 week ago
Our first visit to AMI. We loved the condo and being right on the beach. Beautiful sunsets right from our deck. Perfect condo for a couple. Walkable to local restaurants and Bridge Street area. We did not rent a car and used the free trolley and even Uber to go to dinner on LongBoat Key. Great stay. We hope to come back.

Pet-friendly beachfront home rentals

Top guest favorite
A cozy bedroom features a spacious bed dressed in soft linens, complemented by light blue accent pillows. Natural light enters through plantation shutters, illuminating the room. A small wooden desk with a chair is positioned nearby, enhancing the functional space within the room.
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 favorite
A private patio area features comfortable seating arranged around a coffee table, all situated on lush green turf. Large glass doors provide access to the interior space while a white picket fence partially borders the area, enhancing the outdoor ambiance.
Apartment 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 favorite
An outdoor seating area is displayed on a stone patio surrounded by lush greenery. A dining table with chairs is positioned under a blue umbrella, while two light green lounge chairs are positioned nearby. A charcoal grill is visible in the corner, inviting outdoor meals.
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
An aerial view showcases a vibrant coastal community with lush greenery surrounding numerous properties. The azure ocean glistens in the sunlight, leading to the sandy shores in the distance. Streets weave through the neighborhood, with clusters of buildings and pools visible from above.
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.
Guest favorite
Home in Englewood
5 out of 5 average rating, 34 reviews

"Lost Loon" Oceanfront Cottage by Roxy Rentals

RachelRating, 5 stars1 month ago
Beautiful views from this beach bungalow that provided lots of amenities - comfy beds, plush towels, well-stocked kitchen, beach chairs, etc plus extras like a bottle of wine and sunscreen. We really enjoyed our time here. The only negative was the lack of a solid door on the main bedroom. It’s a slatted closet door so it limited privacy and was not quiet if anyone was in the kitchen. Still, we’d highly recommend it for the location and the completely updated cottage!
Superhost
Home in Holmes Beach
4.67 out of 5 average rating, 33 reviews

Casa Posada - Cozy 2BR Cottage, Steps to Gulf

BeccaRating, 5 stars8 months ago
This rental was so clean and the property owners were always very responsive and friendly. The beach was right outside the door and very clean. The best part was having the beach gear delivered and picked up by a third party so we didn’t have to worry about it. We love AMI and would definitely recommend this property.
Superhost
A living area is visible, featuring a floral-patterned sofa and a light blue coffee table. Tile flooring spans the space, with a dining area and kitchen in the background. Natural light is provided by large windows, enhancing the open feel of the room.
Home in Holmes Beach
4.59 out of 5 average rating, 59 reviews

Beachy Coastal Rental in Holmes Beach

CherylRating, 5 stars1 month ago
This place was so nice and clean and very cute! Jessica is very helpful if you have any questions and gets back to you right away! Very close to some restaurants and bars and the beach is only a couple of blocks away. We really loved it and Chris the maintenance man is very friendly and helpful. We ran into the cleaning lady a few times while she was cleaning the other place and she sure is very friendly with a smile! We will be coming back for sure! Holmes beach is very peaceful and full of friendly people! We stayed for a month but will stay longer next time!
Guest favorite
A welcoming living area features a gray sectional sofa and a modern chair positioned near a wooden coffee table. Glass doors open onto a balcony with a view of palm trees and the outside. A flat-screen TV is mounted on the wall, enhancing the space's comfort.
Apartment 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!!

Quick stats about beachfront rentals in Siesta Key

  • Total rentals

    170 properties

  • Nightly prices starting at

    ﺩ.ﺇ441 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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