
Beach house holiday rentals in Siesta Key
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Top-rated beach house rentals in Siesta Key
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Holiday rentals for every style
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Popular amenities for Siesta Key beach house rentals
Beachfront house rentals

Beach front! Sunsets + Bridge Street+ Restaurants!
Our family decided to go to Anna Maria Island to celebrate my oldest graduating high school. It was by far the best, most relaxing vacation we’ve had. Everything about the location, atmosphere, walking distance to the beach, and especially the home was perfect! Ashley was a great host, kind a responsive, and provided the exact replica of the picture perfect home you see listed. Thank you for this much needed slice of paradise. We will definitely be back!

Canal home short walk to Beach & Village, Heated P
Can’t say enough good things about the house and Steven. The house was beautiful, it was everything we could’ve wanted and to have the additional beach supplies readily available was amazing! Steven answered so quickly and was happy to help however he could. 10/10 for us!!

The Peachy Beach House, steps to the gulf
We had the most wonderful 5 days here. House and pool were amazing. Heated outdoor shower was great for after the beach. Beach is less than a 5minute walk away. We walked there several times at sunset and got beautiful photos. restaurants and shopping near by. we will definitely be back!

Ocean Air Oasis-New Centrally Located AMI Luxury
Great place. Very clean and private. Easy walk to the beach. Hope to stay here again.

Sea Shack - 2bd/2ba POOL Home
Words can't describe what this place looks and feels like! It is beautiful, comfortable and accessible. If you are looking for a nice place to stay and enjoy the beach and pool all day, this is the spot. It has all the necessary amenities for the trip. They do have beach chairs, cart, umbrella and beach toys. The arrival and check in was no hassle at all, had no need to contact the host, as everything was well taken care of and it had written detailed instructions for further assistance. The BEACH is extremely beautiful.

Walk to Lido Beach &St. Armands -grill/HEATED POOL
Book this immediately! This house is a beautiful, peaceful, tropical oasis that is close to the beach and restaurants. After a day at the beach, the private pool is a great escape. Claudia was very responsive and kind, she answered any questions we had. We were provided with a great starter pack of house items so we could start relaxing right away!

'Walk on the Beach" heated pool North End AMI
Rasas place was perfect! Rasa was so kind and helpful. We would definitely stay here again!

3bed/2bath Townhouse with Pool & close to Beach
We didn’t spend a lot of time at the place because we spent most of the time on the beach. The location was great, just a short walk to the beach. The place was clean and had all the needed amenities. I would stay here again and plan on it in the future.
Beach house rentals with a pool

Mins to Beach + IMG+ Hot tub + Heated Pool!
We had an amazing stay! We had a family of 8 and the house was perfect for all of us. The house was absolutely beautiful! It was super clean. We spent a lot of time in the pool and hot tub. The outdoor table also has a fire pit which was perfect at night. There were lots of amenities provided. There’s plenty of beach supplies/ extra towels. The house was filled with lots of stuff we didn’t have to pack, because it was already there. The beach is super close, about 10 minutes away, which was a bonus. Ashley has been wonderful! She’s super responsive and even allowed us to check in an hour early. We have a great vacation! We couldn’t recommend this place more! The perfect family vacation home.

The Sand Castle - Backyard Oasis Mins from Siesta!
Loved our stay. Would stay again.

"Enfuego!"
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.

St Armand's Mid-Century Oasis
Had such an amazing stay at James home. Home was beautiful and at great location the pool was definitely a plus. Home was just as expected from description provided. I really loved the location of home as everything was walkable distance to near by shops, restaurants, bars, and beach. Would definitely stay again .

Siesta Key Modern Retreat with Heated Pool & Spa
The house was tucked into a quiet residential community. The home was clean, fresh and spacious. The guest house area with its own bathroom is perfect for a two family stay! The neighborhood was safe to walk in- I walked daily. The neighborhood was really within 15 minutes drive of anything we wanted to do. We spent most of our time at Siesta Key! Leave EARLY for the beach, if that's your day's plan! We would definitely stay again!

Flamingo Royale — Beach Luxury Resort
Such a beautiful place to stay!! Quick responses, super helpful, & very clean! Quiet neighborhood and private residence. Definitely recommend staying here!

Siesta Sands Hideaway - 1 MILE to Siesta Beach!
we had a great holiday in a very beautiful and comfortable house. the pool and spa are great. the house is equipped with everything you need for a relaxing holiday. Jodi is very friendly. we will definitely try to come here again. thank you Jodi!

Casa Bella-5BR/Waterfront/Pool/Spa-9 Min AMI
Everything was great and we really enjoyed our stay! My only note would be to post a picture of the driveway so we know how many cars can fit the guests. We communicated with the hosts and they kindly allowed us to park a vehicle on the street while being mindful of the neighbors so it worked out just fine.
Private beach house rentals

Historic Downtown Sarasota - Gem I
Adorable. Cutest little house on the block. Location was perfect and walkable to everything. Quiet and safe while still being downtown. Check in was easy and parking right next to the home was so nice.

*New* Pool, fire pit, guest house, bunks-near AMI
INCREDIBLE. This home was a mile beyond any other place we have stayed. It was exactly as described and yet exceeded every expectation. It is obvious Rosa has taken great pride to make this a 5-star stay. The real gem is the pool and hot tub. The backyard had it all and was perfect for family fun or a night time soak. Thanks for a fabulous, fun-in-the-sun week!

Beach Retreat! Bikes, Paddleboards, Sauna & more!
Beautiful home and surrounding area, Pristine home in brand new condition. Expertly furnished, lots to do for teenagers, they loved the ice bath! Well stocked kitchen. The host was very responsive and helpful would definitely recommend this location and home. Happy vacationing.

Stunning New 3 bed 3 bath pool home by Siesta Key!
Adam’s place was just what we needed for our family vacation! Super close to the beach, which made it easy to pop over for a few hours of fun with the kids, then head back for naps and chill time by the pool. It was the perfect mix of fun for the little ones and relaxation for us. We couldn’t have asked for a better spot!

Private Heated Saltwater Pool & Spa 1 mi to Beach
We had a wonderful stay at Shelly and Steven’s beach house! The home is beautifully modern, clean, and well-equipped for a relaxing family getaway. We especially loved the backyard pool and how close everything was—walking distance to shops and just a short drive to the beach. It was perfect for our family, including our toddler. We felt right at home and can’t wait to come back!

Intercostal Oasis
Glen was a great host. Super responsive any time I sent a message. We were able to check-in early. The place is close to beaches and easy to get anywhere you need to go.

Downtown Oasis: Poolside Condo, Patio & Gym
Stayed here for the national rowing competition for one week. The place is lovely - very clean, the complex is nice & the pool is great. It was a perfect location for us - halfway between the race course where we needed to be every day and close to downtown. The beach wasn’t far either and I liked the location and the complex very much. We felt safe and it was pretty quiet and peaceful. The owner is responsive and detail oriented with how to check in, get into the unit, etc. I would stay here again.

Cozy Cottage - close to Manatee River
Cute Airbnb ! Very well decorated and super cozy. Easy drive to Anna Maria Island
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- Anna Maria Island
- Siesta Beach
- Anna Maria Public Beach
- Crescent Beach
- John's Pass
- Turtle Beach
- Caspersen Beach
- Bean Point Beach
- Raymond James Stadium
- Cortez Beach
- Lido Key Beach
- Amalie Arena
- Coquina Beach
- Gulfport Beach Recreation Area
- North Beach
- Fort De Soto Park
- Manasota Key Beach
- Vinoy Park
- Jannus Live
- Streamsong Resort
- Tampa Theatre
- Curtis Hixon Waterfront Park
- Splash Harbour Water Park
- North Beach At Fort DeSoto Park