
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

Sun-filled cottage with pool, walk to beach
We loved our recent stay here! We had a bit of a challenge with lots of rainy weather so having a BEAUTIFUL backyard with synthetic grass and an amazing pool SAVED THE DAY(S). We ran outside with every break in the weather and the kids stayed as happy as can be. The home not only looked clean, but FELT clean and the decor was tasteful and didn’t feel overly beach kitschy- as we’ve run into before. Hoping to be back next year!

Beachfront Getaway in Siesta Key
Our stay was so easy and enjoyable! Dior’s place is so cute and very clean. We were able to walk to multiple shops, bars, and restaurants. It was so nice to have our private beach access right down the sidewalk, and right beside the pool! We were also so glad that she was able to accommodate us on such short notice. Everything was perfect! This will definitely be our go-to place to stay when we visit Siesta!

Spacious 2 Bedroom Home | Near Beach | Heated Pool
Melissa's listing was very nice and comfortable. The beds were comfortable and the ceiling fans worked great. The bathrooms were clean and the showers had good water pressure. There was lots to do in Venice and a drive to Sarasota was at most an hour. It was also nice that beach items were supplied, such as chairs, umbrella, coolers, etc. The house was also in a quiet neighborhood and we felt safe at all times. I would definitely recommend to others!

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.

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!

Oasis by Siesta Key Beach and Downtown SRQ w/pool
We had a great stay! The house was exactly like the photos and was very fresh and clean! Instantly felt like a tropical vacation when we walked in. Check in was easy and Michael was awesome with his quick responses, flexible early check in and local recommendations! We went to Walt’s fish market as he suggested and it was so worth it! Amazing seafood! Definitely looking forward to booking this airbnb again when we visit! The house is in a great area so close to everything! Highly recommend!

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!

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.
Weekly house rentals

Stunning Home, Heated Pool and Boat Dock
We had a wonderful experience! The bay was beautiful and we got to see manatees! Highly recommended!

Luxury Pet friendly home, 2.7miles to Siesta Key!
We had a wonderful stay at this property. We were in town for our son's sporting event for several days. It was exactly as described and more. It was clean and comfortable and there were so many "extras" that we do not usually experience in other rental properties. The kitchen was fully stocked with utensils, cooking supples, spices, coffee, and more (better than any rental we've stayed in). There is not one negative thing I can say about this place or the host. Honorata was extremely responsive and helpful and allowed us to check in early, which we greatly appreciated as we needed to drop our luggage and go to an event. The location was great, a short drive to the beach, stores, etc. and the neighborhood was quiet and felt safe. We would highly recommend this property and hope to stay there again next time we are in the area. Thank you Honorata and Conrad for a lovely stay!

Charming Home in Sarasota-8min from Siesta Key
The hosts were very responsive and very helpful. Their home was spotless. The pool with the enclosure allowed you all the sunshine you could ask for without the bugs! The interior is very spacious and great for hosting dinner. With the turf back yard it’s the perfect hangout for adults and children! The hosts are very thoughtful with items available for the perfect beach day (beach wagon, chairs, a cooler, and lots of fun items for children! We will definitely be visiting again!

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!

Sea La Vie On Brink- cheerful 3/2 w/ shuffleboard
We enjoyed staying here and will be back.

Cottage w/Fire Pit Near Siesta!
This house was beyond what we expected and we look forward to renting it again for our next Siesta Key trip. Betsy was outstanding and such a wonderful host.

Stay & Play - 4 min from IMG
I had a great experience staying at this Airbnb! The place was exactly as described clean, comfortable, and had everything we needed for a smooth stay. The host was amazing very friendly, responsive, and easy to communicate with.I would definitely stay here again and highly recommend it to anyone looking for a hassle free and enjoyable stay!

1 Bedroom Cottage 7 Min to Siesta Beach
Great place to stay !! Love the location, only 8 minutes to Siesta Beach!! Everything was close by, easy access to two of the main thoroughfares, Tamiami Trail and Clark. Strait shot to 75 , too. Loved the gas grill and patio furniture. Had a few little visitors out there, a couple of Geikos running around keeping me company while I was grilling. Very clean and newly redone throughout. Beautiful place, highly recommend it !!!
Private house rentals

Lovely Beach Bungalow
Olga’s place is such a gem! We had a wonderful week long stay - we felt right at home the moment we stepped inside! Olga was so sweet and always made sure we had what we needed. The pool was an added bonus, it felt like we had a private oasis to hang out at after we went to the beach. The house was impeccably clean and stocked with everything you could possible need for a comfortable stay. The AC was lovely and the beds were so comfy, everything about this airbnb exceeded our expectations. We didn’t want to leave, but already can’t wait to come back one day. We highly recommend Olga’s place 😊

Paradise on Prospect w/ Htd Saltwater Pool
This is the nicest vacation rental. The details are spot on. It is well appointed with quality products. PMI Is very responsive. Love the location and proximity to Ed Smith, Downtown Sarasota and more. We look forward to returning.

Suite Sun
Our stay at Ryan’s place was perfect. It felt private even though it’s in a neighborhood. The location was great for our beach and shopping trips. There are several amazing local restaurants within a few miles. We’ll definitely be back!

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.

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

Paradise In Siesta!
We had a great stay here! Walking distance (10 minutes) to the beach and cute neighborhood. Great place!

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 .

NEW hideaway, Saltwater Pool&Spa, 10min to Siesta
I will definitely go back and stay here again when in Sarasota. The new beautiful modern pool and hot tub area is amazing was so tranquil and well thought out with high end lounging/seating for 10+. I spent most of my free hours around the pool area when at the house. WIFI was great when needing to work. The location was an easy drive to the local restaurants and quaint downtown area 5-10 min., to the closer beaches 15 -30 min., was bicycle/walkable for me (I am 65 y/o). I was in town for a conference and also saw alot of people on nearby small/clean little open air trolley-like buses getting around downtown (might want to check those out). I felt safe and walked/explored to the downtown hotel area (~ 40 min.). So close to the convenient Sarasota/Bradenton airport (~20 )! The hosts were so responsive and genuinely caring, they anticipated my needs before I asked by offering suggestions and options, so worth the stay! Thank you to the hosts!
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