
Mansion holiday rentals in Siesta Key
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Top-rated mansion rentals in Siesta Key
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Popular amenities for Siesta Key mansion rentals
Luxury mansion rentals

Arlington Ocean Oasis 5br 5ba Htd Saltwater Pool
Beautiful house just like the pictures. The beach accessories were a great bonus. The pool area was enjoyable and relaxing. Our group of 8 had a great time and would highly recommend.

Heated Pool |Game Room|SmartTVs|King Beds|Sleeps14
Our family had the best time at Dana’s. The pool and game room were enjoyed. Comfy beds and furnishings. It was a great place to stay and had everything we needed and more.

"Enfuego!"
We had such an incredible time staying at this property! It has everything! Plenty to do even on rainy days. Can’t say enough about it. We had 8 adults and a baby and king beds for everyone which is hard to find. So private in the back yard and unique!

LUXE Nomadic Abode heated pool & amazing yard
5 Stars – Wonderful Stay! I had an amazing experience staying at this Airbnb! The place was spotless, beautifully decorated, and exactly as described in the listing. The bed was incredibly comfortable, and I appreciated the thoughtful touches like coffee, local guidebooks, and extra towels. The neighborhood was quiet, safe, and within a few miles away there is great restaurants and shops. Our host was friendly, responsive, and made check-in super easy. They even gave us great local recommendations that made our trip even better. I would absolutely stay here again and highly recommend it to anyone visiting the area!

[The Bay St. Hideaway]Private Swimming Pool& Patio
Bay St., Hideaway was very accommodating for our family while traveling for a very special occasion. This place allowed four different families to stay in the same location and share meals, laughter and good times with grandchildren, children and parents. It is located in a quiet neighborhood that is located to a lot of nearby attraction. I would totally recommend this for any family that is gathering for that once in a year special event.

Private Pool, Spa, Rooftop Deck, Game Room & More!
100% recommend staying here. Me and my fiancé have stayed at many Airbnbs across the area and this by far stood out by one of the nicest and best located. The hosts were incredible and very responsive as well!

South Water View - Residence 502
Our stay at Ten35 was great! Great location with direct access to the beach. If you plan to stay around the area while visiting, you most likely will not need a vehicle as this is close walking distance to most of the restaurants and shops near by. The condo was overall very nice, comfortable, clean, and very spacious.

Acacia Haven
The house was perfect! Just as described and a great layout for a large family. The amenities were awesome especially the outdoor space with the pool and spa and outdoor TV. Very kid friendly with toys and crib and highchair. Would definitely recommend 10 out of 10!
Pet-friendly mansion rentals

Pool | Game Room | Fire Pit | Pet Friendly | 3 TVs
Place was as listed. Nadia and Serge were very responsive. We did have an issue with the pool and they sent over the pool tech. We enjoyed our stay.

Sarasota Getaway “Have some fun under the sun.”
Such a wonderful stay! We had a group of 6 girls and this accommodated us all very well! The pool was amazing and the extra outdoor amenities made this place a perfect place for groups. Beautiful spacious kitchen and dining area as well as wonderful showers and bathroom spaces. Easy parking and a very safe neighborhood overall. 15-20 from siesta key main beach and downtown, very convenient!

Chic 4BR + Jacuzzi | 9 Min to Siesta Key Beach
Super nice place! Very close to everything, including the main drag with all the shops and restaurants. And only 10-15 minutes from the beaches. The inside was very cute, nicely updated, and there was just a lot of thought put into the tiny details with the amenities provided. We’ll totally book this place again when we come back down!

Twin Palms: Big House Steps to Beach w/Lush Pool
We enjoyed our visit to TwinPalms very much! The home was in a wonderful location on the island! The home is beautiful, and is equipped with anything you may need! Kathleen was so very helpful in making sure we had everything we needed and made our visit seamless! The love and effort Kathleen puts into your visit could not go unnoticed! Really appreciated the materials she provided on everything to do on the island listing the restaurants with her personal reviews was helpful!

Family Oasis-Beautiful House-Infinity Pool-Beaches
This was the most beautiful and accommodating Air Bnb I’ve ever stayed in. Everything was new, clean, and updated with the latest technology. The toilet seats were even heated! We had a group of 9 plus a dog and everyone was very happy with the stay. Marcin was super nice and always answered questions quickly. The pool area is incredible. The kitchen was stocked with everything we needed to make meals and the bathrooms were stocked with plenty of essentials.

Sarasota Sandpiper: 4 Bed/3 bath + Pool
The Sandpiper was the perfect airbnb for our small group. Having the 4th bedroom and 3rd bath that could be used from the private pool was perfect. The fenced in backyard made it great for our friend's dogs to run. The kitchen had everything we needed and allowed us to cook in daily. Proximity to grocery was great and with a few extra people who stopped by to visit, the 24 hour Denny's four houses up allowed us extra parking and less congestion of cars around the house. This airbnb gets a five star rating.

Heated Pool, Boat Launch, Sleeps 10!
The home was beautiful, It was move in ready, equipped with all the features of home and more. Each room had plush bath robes. It was beach ready, equipped with beach towels, beach wagon, chairs, and mats. Even though we did not have a baby or small children, a high chair and sleeping equipment was available. The Pool area was clean and very comfortable. Great selection of spices for cooking. Attention could have been given to the oven. The management team was welcoming and extremely responsive to needs concerning the property. Great find. Highly recommend.

Coastal Retreat w/ Heated Pool – 6 Min from Siesta
We loved our stay at Yasmine’s beautiful home. We had one question regarding the thermostat (apparently my Midwest self isn’t used to the FL heat) and Yasmine responded within a minute. The home is gorgeous and very clean. It has all the amenities listed. Our boys especially loved the heated pool. The beds were very comfortable and clean. There were a lot of little details (like laundry detergent, shampoo, conditioner etc) that made the place feel more like home. The location is perfect, close to shopping, local restaurants and Siesta Key Beach. I can’t say enough wonderful things about Yasmine and her beautiful home. We will definitely stay again should we come back to Sarasota.
Mansion rentals with a pool

Private Backyard + Heated Pool + Luxury Boho Style
Fantastic Stay – 10/10! We had an amazing time! The setup was perfect for our girls trip —super cozy with a fun beach vibe that made us feel right at home. The kitchen was fully stocked, which made cooking meals easy and enjoyable. The beds and pillows were incredibly comfortable—we all slept great! The location was ideal: close to stores and restaurants, and just a short drive to the beach. The neighborhood felt very safe, and we loved taking walks around the area. Would absolutely stay here again!

The Pink Riverhouse- No damage from Hurricanes
Our stay at Katie's was a wonderful experience. So much to do within the house as well as the backyard. Katie & Terry were both prompt when needed throughout the trip and made us feel at home. Katie also have great recommendations for grocery shopping which made me fall in love with the Amisb Supermarket. Also, great proximty to many attractions. We will most definitely find more time to stay here again!

Lagoon View*Close to Siesta Key*Centrally Located
Loved our stay!! Only comment is that one bathroom only had 4 rolls of toilet paper for 9 people, which wasn’t enough but besides that, we had everything we needed! - Excess towels, sunscreen, games, stocked kitchen with dishes and some snacks. Pool is clean and 3-5 feet. Pool noodles, wagon and cooler available for use which was awesome to borrow 👏🏼

*New* Pool, fire pit, guest house, bunks-near AMI
We enjoyed our stay in Bradenton! The home was very welcoming and spotless. The quality of all kitchen amenities were outstanding, by far one of the best kitchens of all the places we have rented. The bedrooms and bathrooms were very clean. We loved the King sized beds in every room. The backyard is beautiful, private and peaceful. The pool and hot tub were the selling point for this Airbnb! The neighborhood was quiet yet still very close to several stores. The drive to local beaches was ~15-20 minutes. We were provided with various pool and beach items that we could use - all which were great quality. Our host Rosa was wonderful. Her response time was quick and she made sure everything was up to par. She resolved issues quickly, which we are thankful for.

Urban Oasis, Pool, 6mi>Beach
I took my entire family to Sarasota as a Christmas present. The trip was everything and more! Karen was a great host and our Airbnb was perfect! We felt right at home in this beautiful space and enjoyed every minute! Would definitely go back in a heartbeat to make more amazing memories!

Summer Special|Anna Maria in Mins|Kid+Dog Friendly
We absolutely loved our stay! The house is beautiful and very clean. The pool was amazing, it kept our kids busy on the rainy days. It was about a 15-20 min drive to the beaches, definitely get there early for free parking. Plenty of restaurants and stores close by. I can’t recommend this place enough, thank you for having us!

New home,mins to beach, heated pool,two kitch
Michael’s place was absolutely as advertised! Believe the pictures. What you see is what you’ll get. It was impeccably clean and in great condition. The pool and jacuzzi were nice to relax in during the evening. The kitchen was well equipped. We prepared quite a few meals there. We had 8 adults in the house and all were comfortable. Michael and Rueben were very responsive. We had a couple questions and they provided answers within a minute of us asking. Great experience!

White Pearl-New Premier AMI Home with Sunset Views
This was our first time on Anna Maria and we loved it. The White Pearl played a big part in our enjoyment of the island. It had plenty of space for a big family and everything we needed for a seafood dinner at the house, a day at the beach, or an evening by the pool. The weather was great so we took full advantage of the decks, especially the observatory, which has a great view of the Osprey nest across the street. We spent plenty of time soaking up the sun and watching the beautiful sunsets, so it was great to have quality chairs, umbrellas, and a wagon to get it all to the beach. Jay was very helpful and clearly takes pride in his home and the satisfaction of his guests. He called to check on us when we arrived to see if we needed anything and was there at check out time too. We’ll definitely be back. Thanks Jay!
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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
- Vinoy Park
- North Beach
- Fort De Soto Park
- Manasota Key Beach
- Streamsong Resort
- Tampa Theatre
- Jannus Live
- Curtis Hixon Waterfront Park
- Splash Harbour Water Park
- River Strand Golf and Country Club