
House vacation rentals in Province of Siena
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House rentals with a pool

Hidden gem in Tuscany
Where to start? I truly can't say enough good things about this property. It exceeded expectations in every way. From start to finish, our time here was a delight. Amanda was responsive, helpful, and accommodating. The location is remote, and a bit of adventure to get to, but Amanda had communicated that and we were prepared with the proper rental car that made it a breeze. The house is beautifully appointed, has every amenity, and lots of perfect spaces for both quiet moments and areas to gather with your group. The outdoor spaces and pool area are lovely, beautifully landscaped, and the views are spectacular. Book this place; you won't be sorry.

Italian Interior
What a wonderful experience! The description of the home was excelled by the reality. It was very clean and tastefully decorated — Anna has an eye for design and art. the three bedrooms easily accommodated us. The large patio with its charming table and vine screened roof was a charming place to enjoy our morning cappuccino. the home is situated in a agricultural community built in 1788, situated in extensive vineyards. The buildings have been thoroughly renovated into a series of private homes. The community contained renters like us, but also young communities and older retirees. We had a chance to get to know people in the neighborhood, who were uniformly friendly. the AirBnB is about 25 minutes away from Arezzo by car. The best place to park we found was in the short term parking at the train station. From there it was just a short walk to the Old Town. Anna was a wonderful and charming host. We recommend this property highly!

Infinity pool in Chianti area
"Perfect" is the only word that comes to mind for Anna's place. Such a serene location and perfect for a family. The view is just spectacular. We felt so at home and loved sitting out in the yard and by the pool. Anna provided us with a list of so many amazing things to do/see near and far. A must do is the pasta making with Vilma at the house-the most memorable and delicious meal from our trip! Can't wait to go back there to live more of the Tuscan life and enjoy the most beautiful view. Thank you, Anna, for hosting such a gem!

Wonderful country house
We had a brilliant week at Jakob and Margit’s house. Margit was so friendly and helpful (and gave us some wine and fresh eggs!). The views from the gardens are incredible and having the swimming pool was perfect. The local area has lots of great vineyards to visit and the house is close to Florence/Siena/Arezzo for day trips. It had everything we needed like a washing machine etc.

Family Forest - Pool in the Crete Senesi
The apartment really enchanted us, the rooms are nice, clean with air conditioning, stylish, in the living room a large TV, kitchen with everything that should be here. The "resort" itself was on a hill with beautiful views, a huge garden, a swimming pool, all stylish Tuscan, the surroundings are beautiful, peace, quiet, peace, everything you need here you will find. As the Italians say, it's "Tutto bene" here

A Charming House in Asciano - Siena
Very nice place with a great view, very quiet and relaxing. The apartment was clean and cozy. The only inconvenience were the squeaky doors.

Charming estate with views
Incredible stay and Bernardino and his family were incredibly welcoming and pleasant. They helped us check in later and were there to help us with any questions we had. Absolutely would recommend to anyone looking for a peaceful Tuscan retreat.

Podere Tignano, 4-bedroom villa in the Chianti!
How can we even put into words what an incredible experience this was! Antonella was kind and helpful, and her home is just stunning. She made us feel so at home even with our limited Italian. She prepared us a home cooked, four-course meal one night and it was absolutely delicious. She even gave us the leftovers so we could have them for breakfast the next day. The villa was breathtaking and in a perfect location to visit beautiful towns in Tuscany like Pienza, Montepulciano and San Gimignano. We especially loved the pool and visiting with the animals. This was a bucket list stay for us and worth every penny!
Weekly house rentals

Casa Ora d"Oro - Panoramic Views
first I love his neighbors who checked us in. Cinzia was amazing. She not only showed us our place but took our kids to show us her farm. she also makes her own olive oil and gifted us with some! Wonderful Italian neighbors!! I contacted Rocky in advance and he provided me with specific recommendations for where we should go during a long drive we took. we went where he suggested and was not disappointed! Amazing quiet location with great near by wineries. would 100% recommend to everyone!

the chestnut house
Casa di Laura is a dream. I shared the location with all my friends because coming here is a wonderful gift to give yourself. We left reluctantly, like when you leave a vacation home you've grown fond of. The surroundings are beautiful, as is the house, a quiet garden and cared for in every detail with the pool that changes the whole vacation. A dip before going down to Siena to visit (which is 15 minutes by car, not even) is one returning home before going down for dinner. Ideal for cooling off from the summer heat. It was really wonderful, and we'll be back! Thank you so much Laura for sharing with us restaurants for lunch, dinner and aperitif and for being so flexible with the schedule. We haven't even met, but after being at your house, it's like I know you. Thank you!

Oliveta Verde with garden near the center
Amazing property - stunning views, and outside space. Warm and cosy with beautiful decore. Spotlessly clean. So close to Siena , a very easy walk! Elena was extremely responsive and could not be more helpful

Agriturismo Podere San Martino (apartment for two)
Everything was just like in the pictures. We had a great time. The view was amazing and Maddalena was really helpful. Thank you!

La Casetta
Hard to find a place like Maria’s, beautiful place and with such a friendly and helpful staff.

L'Uva Fragolina. House, Garden, Panoramic View
A Tuscan dream. Some days I had to pinch myself to understand that I was not in a movie. My girlfriend and I had a wonderful time in the area and also in the house. It was clean and tidy. The kitchen was unique and we also enjoyed grilling outside. We simply enjoyed it and felt at home. Finally, relaxation and tranquility, which you rarely experience. Thank you for your trust in this wonderful piece of Tuscany. For all those seeking peace or people who really want to experience what Tuscan flair means, a must-see. We will be happy to come back!

Casa Iris (with jacuzzi) - Close to San Gimignano
Sylvia was an amazing host from the beginning! She came to meet us at the check-in and made sure all our needs were met any time of the day. She was very sweet and made us feel right at home! The place has a very nice hot tub facing the mountains and it gave us some beautiful sunset views! 10/10 would recommend!

Bright loft in the heart of Siena!
Francesco’s loft was in the heart of Siena and had plenty of restaurants and things to do within walking distance of the airbnb. I recommend packing light for Siena in general, with the hilly streets and about 20 steps up to the Airbnb from the external door- which was no problem for my sister and I. The loft was spacious, clean and very comfortable. We spent most of our time outside exploring, but it was a peaceful place to start our morning making coffee and end our nights. The place was very clean and had a very nice shower with multiple settings. The upstairs bathroom with washer was convenient and allowed us to pack lighter. Francesco was a very responsive host, letting us know check in info early on and answering any questions we might have had. I highly recommend this serene spot. I also unfortunately upon leaving realized I left a couple of dresses and Francesco was quick to respond and willing to send them to me. An amazing host!! 🫶🏽
Private house rentals

S.Ilaria - Private pool Villa with 2 bedrooms
Fabulous setting in the middle of fabulous Tuscany. The views from the house were stunning! The farmhouse itself was so charming - every detail. We enjoyed dinners on the covered patio, evening walks on the gravel road through the countryside and lounging by the pool with a glass of red wine. The setting is also the perfect location for day trips to nearby cities. We visited Montalcino, Montepulciano, Siena, Pienza and Cortona. Highly recommend!

Cozy country house Podere Scorno with pool
Very local experience ~ It's also great to be able to experience local life!It's like going back to the environment and house when I was a kid. The stay was very comfortable!The host is also very nice!!!Gave a lot of recommendations!!!Thank you very much!!!

LA RONDINAIA. AMAZING VIEW ABOVE THE CHIANTI
Sebastiano’ place a real heaven in the heart of Chianti mountains in Tuscany. Amazing project, wonderful nature and history everywhere around. Place is so peaceful and unique. Just a dream which came true!

Beautiful villa with pool in secluded location
We had a lovely stay here. The location was perfect—exactly what we were looking for. Peaceful, quiet, surrounded by nature, with classic rustic, yet elegant furnishings. The villa is gorgeous with attention to design & detail. For 6 women, it was perfect for us each to have our own bedroom and space to relax. Each room had its own unique view and touch. There are also plenty of common spaces throughout the house for connecting together. The kitchen is large enough and fully equipped for plenty of great meals to be prepared and enjoyed together. The dining room is nice to enjoy a more elegant meal. The outdoor spaces are beautiful. We used the outdoor terrace for watching the sunset, enjoying brunch, and making pizzas. The washing machine and dryer are easy to use. The pool area is beautiful and there are plenty of outdoor spaces to go for a walk and enjoy the surrounding nature. The hospitality was unmatched from Tristan & Angela. I will absolutely book again and hope to return soon!

Capezzuolo 33
This apartment was so beautiful and the views were even better. We had an amazing stay here as our base for exploring Tuscany - visiting the Val d’Orcia and the thermal baths were a highlight! Lucia and Marco met us on arrival and were extremely friendly and gave us plenty of advice and places to visit. There was an issue with the boiler but Lucia was straight on it and it was fixed by the time we were home for the day. Thank you so much!

Explore Chianti from a Charming Stone House
Best part of our Italy trip! We loved our stay at Casa Marinella, and Monica has thought of every detail to make for a wonderful and peaceful vacation! Relax by the pool and enjoy breathtaking views. Be sure to stop by Gelateria di Castellina for a scoop of cremino gelato and try the fiorentina steak at Osteria La Sosta di Pio VII.

Casa San Ripa: Relax Oasis with Private Pool
We had an amazing time in Casa San Ripa. The house is even nicer than it looks in the pictures, the view is amazing and the outside area is lovely, with all the lights in the trees at night. The whole property was very clean, including the inside and the pool, the instructions were easy and Giulia is super responsive and extremaly nice and helpful. We had a great stay and would highly recommend!

Country chic house in a village,private pool,wiFi
Lorenzo met us on the street to walk us to the villa and showed us everything with a very warm welcome! The views are breathtaking! We found the location to be an excellent base to visit all of the surrounding towns. Having Grazia Franchini (see the host’s guidebook) prepare and serve dinner for us in the villa after a fabulous day of Brunello wine tastings was such a treat! Would definitely return to the area and stay here again but next time will set aside a day just to relax by the pool!
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- Santa Maria Novella
- Duomo di Firenze
- Lake Trasimeno
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Basilica of Santa Maria Novella
- Mugello Circuit
- Ponte Vecchio
- Cala Violina
- Fortezza da Basso
- Uffizi Gallery
- Parco delle Cascine
- Piazza della Repubblica
- Piazzale Michelangelo
- Mercato Centrale
- Kite Beach Fiumara
- Marina di Grosseto beach
- Pitti Palace
- Stadio Artemio Franchi
- Giardino Bardini
- Cavallino Matto
- Avignonesi Winery Fattoria Le Capezzine
- Medici Chapels
- Cala Di Forno
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
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