
House holiday rentals in Siesta Key
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Top-rated house rentals in Siesta Key
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Popular amenities for Siesta Key house rentals
House rentals with a pool

Ground floor home 2BD2BA garage Pool Private beach
We had a fabulous stay! The location is perfect. The condo was spotless and nicely decorated. We had absolutely everything we needed. The private beach was clean and not crowded. Chairs were readily available. The location is great. There was an unexpected issue when we first arrived, but Amy was incredibly responsive and supportive, checking in regularly to make sure we were okay and comfortable. Her excellent communication and customer service was exceptional. Once everything was settled, we were able to fully enjoy the space and the beautiful surroundings. Can't wait to go back. We would definitely recommend booking this property.

La Hacienda / heated pool, hot tub, 6 mi to beach
Fantastic Airbnb! Seaglass Management and Joy are great to work with. Very responsive! Great location, very safe, amazing pool and jacuzzi, close to downtown, restaurants and the Legacy bike trail. Will definitely book again in the near future.

5 minutes to private Siesta Key Beach + 2 pools
Solen was an amazing host—very responsive, friendly, and helpful throughout our stay. She even brought us a brand-new can opener when we needed one! The house was spotless, cozy, and located in a great area. We had a wonderful time and would definitely stay again!

Beach, Village, Dock & Private Pool! One-of-a-kind
Marko’s family home was beautiful, charming, and spotlessly clean. The home is perfectly located, walkable to beautiful beaches and great restaurants and shops, including the market. Marko was extremely hospitable, ensured we were all set and gave wonderful recommendations. We loved this place and will be back again next year. Thank you!

Casa Blanca Ranch Home near Siesta Key Beach
Casablanca exceeded my expectations. The house is much larger than it looks in the photos, with a large and well-equipped kitchen. The house is very cozy and comfortable, and I can't forget to mention how clean the house is. Matthew was super nice and responded to my messages promptly. I have no complaints about the house, and I would definitely rent it again. The outdoor area is very nice, and we had great family moments there, enjoying the pool and having a barbecue. The neighborhood is very peaceful and quiet. The garage has everything you need for a peaceful day at the beach, from chairs and coolers, to even tents if necessary. The location is very good, with stores and supermarkets very close by. It took us about 12-15 minutes to get to Siesta Key. Anyway, I definitely recommend the house!

Sea Club II Garden House
This location was perfect- we could walk to the beach and have a short trip to local restaurants and grocery stores. This beach is spectacular, and the most beautiful I’ve experienced. The house was everything we could ask for - very clean and the rooms and furniture are comfortable. The pool is a nice add though we didn’t use it- we were at the beach instead. We didn’t need to contact Richard as everything was as expected and explained. Thank you so much!

True Island Living House/beach/water views
This was among the most beautiful and well-appointed Airbnbs that we’ve had the pleasure of staying in! Our trip was centered around a family 60th birthday celebration and this was such a lovely backdrop for our gathering. Our primary plans were to enjoy the sunrises and gorgeous outdoor area, cooking meals on the grill and enjoying them by the pool with a view of the intercoastal waterway. As such, when we arrived to find that the grill wasn’t working properly, we were disappointed. We communicated with our host about the grill the day after our arrival, and received an immediate response. However, it ultimately required back and forth texts (some at our initiation due to not receiving an update) and three days until the handyman graciously brought over his grill to loan us. Something we learned from this trip is the importance of communicating to your hosts what it is about their place that is most important to your stay—and perhaps we should have checked on the grill specifically.

Cozy Boho Bungalow Pool/Spa QR Code Walkthrough
Lisa house was and is beautiful you feel right at home. The spa was everything you could ask for it was my 40th birthday and she even had a small cake and balloons for me the was a really nice touch I would recommend anyone looking for a lovely bungalow style home too check Ms.Lisa home out you won’t be disappointed I promise
Weekly house rentals

The Shore House Private Dock Hot Tub
Greta stay - perfectly decorated and in a greta location.

Relax in a Private Tropical Retreat on Siesta Key!
myself with my Partner Paula, daughter Sammy and her boyfriend Tom stayed at Jonathan's wonderful house for 2 weeks, starting May 25th 2025. We were all delighted with the house and fully equipped with all our needs. We made use of the communal pool and found those that lived in the community very helpful and friendly. We made use of the Breeze bus that was great for going to the village. I made contact with Jonathan a few times regarding minor things and he responded very quickly.

Coastal Retreat near Siesta Key Beach and Downtown
We had the most perfect stay at Aubrey’s! We loved everything about it! Great location, so comfortable and nice, close to great restaurants and close to beach as well. The design features of the house and everything in it is very well curated and a house you want to spend time in and enjoy the beauty. The beach chairs and umbrella were perfect for the beach. We highly recommend Aubrey’s place and will definitely stay here when we come back! Melissa and John

Oasis by Siesta Key Beach and Downtown SRQ w/pool
We had the best stay in Sarasota and didn’t want our trip to end! The house was beautiful and in a great location, close to shops, restaurants and not too far from the beach! Michael’s place was very accommodating and has all the amenities. Michael was very responsive and helpful. Loved having access to all the beach chairs and towels. We will for sure be back!!

Endless Summer Escape Near SK!
Great location. 10 min to the beach. The house was clean and had all the amenities we could need. Fully stocked kitchen, towels, toiletries. They even had beach toys for my daughter . The pool was clean and there were plenty of floats and pool toys. I would definitely recommend this house. We would absolutely stay here again on our next visit.

Modern Organic King Beds Salt POOL/SPA SRQ Escape
Our family recently enjoyed staying at The Coastal on Hyde. The home was immaculate and the furniture and decor were both comfortable and beautiful. The pool was probably our favorite feature! Also, it was great to have beach chairs, coolers, and beach umbrellas provided. Our hosts checked in with us several times to make sure our needs were being met. We wouldn’t hesitate to stay here again-it’s a wonderful property!

The Wisteria Oasis W/ heated pool & hot tub
We had a fantastic stay! The home was spotless, stylish, and comfortable, just like the photos. The amenities were great. Appreciate that David was super responsive & a helpful host. Check-in was easy too! I would 100% stay here again and highly recommend it to anyone looking for a relaxing and hassle-free stay in Sarasota.

Gulf Gate Retreat- 2BD/1BA Hot Tub Near Siesta Key
I booked this place for my parents from Germany and they absolutely loved it! Everything was perfect. They really appreciated the thoughtful extras like coffee, sugar, shampoo, shower gel... The apartment was very clean and just a short drive to the beach. Highly recommended!
Private house rentals

“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.

Oceanfront Home with Heated Pool in Fishers Haven
House is immaculate! Super clean and comfortable. Beds and linens were luxurious! Ceiling fans in entry room including the screened in porch. Nice touch! Backyard waterfront is amazing. We used pool and hot tub multiple times per day. We fished off the dock and caught a few catfish. Sergiy was a perfect host. Excellent communication and direction when needed. Highly recommend!

Rustic Sands - 650
Our time at this Airbnb in Siesta Key was amazing! The house was super clean and had an awesome kitchen with everything you could think of, plus more. Great appliances, tons of towels, dishes, some games, TVs with premium channels and more! Outside was just as great. The pool area was covered with mosquito netting, so we could relax without bugs bothering us. The pool was our favorite spot! super clean, and the outdoor BBQ grill was great! The only thing was the master bedroom bed was a bit small and not the most comfortable for us (queen size), but everything else was so good. The neighborhood was really quiet, location was 4 minute drive from the beach. Overall, this Airbnb was one of the best places we've stayed. I would 100% recommend it and would come back! it looks better in real life than the photos.

Cozy Coastal - 2bd/2bath with Heated Pool and Spa!
Great location! So close to many different beaches and restaurants. The private pool area was our absolute favorite!

Casa Playa Sleeps 6
The house was perfect for our small family of three and two dogs! The fenced in yard was wonderful and the location was perfect. The neighborhood is quiet with very low traffic. Only a short drive to Siesta Key, downtown, and other attractions.

Stunning 3BD Siesta Cottage - Walk to the Beach!
This property is stunning! The pictures matched the home perfectly! The kitchen was well-stocked with needed utensils. There were enough supplies (laundry pods, dishwasher pods, coffee pods, toilet paper, etc.) to take care of us for several days. The location was perfect for walking to the beach every day. We loved getting to use the beach chairs, umbrella, and towels since we flew in and couldn’t bring those items. The spaces in the home were very generous, plenty of room for two couples and an infant. The check-in and access instructions were concise and timely. The outdoor shower was excellent, helpful for rinsing off sand as well as being a cool amenity! If we vacation in the area again, I would definitely book the home again!

Paradise Retreat
The house was immaculate. The neighborhood nice and quiet yet close to restaurants and the beach. Large bedrooms and bathrooms made it very comfortable. The poor area offered shade and sun and was really relaxing.

3 bedroom Heated salt water pool close to Siesta
Great place! The house itself is beautiful and well maintained. Very well equipped with the necessary utensils. The pool was awesome, very clean and was heated at times. There is a walmart and publix just 2 minutes away from house plus plenty of gas stations! The beach was very close, about 20 minutes away from the house. I recommend turtle beach which was great, free parking and not too crowded like siesta key beach. Overall the place was amazing and host was very accomplished and reaponsive. Thank you se
Quick stats about house rentals in Siesta Key
Total rentals
420 properties
Total number of reviews
6.7K reviews
Family-friendly rentals
390 properties are a good fit for families
Pet-friendly rentals
200 properties allow pets
Rentals with a pool
290 properties have a pool
Rentals with dedicated workspaces
280 properties have a dedicated workspace
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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