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House vacation rentals in Province of Siena

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Popular amenities for Province of Siena house rentals

House rentals with a pool

Top guest favorite
A private pool is situated amid well-maintained gardens, surrounded by varied greenery and tall trees. Colorful loungers are arranged along the patio, inviting relaxation. The clear water of the pool reflects the sky, enhancing the serene outdoor setting.
Home in Castiglion Fiorentino
5 out of 5 average rating, 36 reviews

Hidden gem in Tuscany

MitchellRating, 5 stars1 month ago
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.
Guest favorite
A modern living area features a beige tufted sofa, complemented by a sleek coffee table and a vibrant area rug. A wood-burning stove stands beside a stacked wood display. Natural light filters through a window, providing a cozy ambience.
Home in Arezzo
4.9 out of 5 average rating, 167 reviews

Italian Interior

LloydRating, 5 stars8 months ago
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!
Top guest favorite
Home in Barberino Tavarnelle
5 out of 5 average rating, 109 reviews

Infinity pool in Chianti area

KrisRating, 5 stars2 weeks ago
"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!
Guest favorite
A serene outdoor space features a large, clear swimming pool surrounded by carefully manicured hedges and tall trees. The rustic stone house stands in the background, complemented by a few lounge chairs near the pool, offering a peaceful setting for relaxation.
Home in Cavriglia
4.93 out of 5 average rating, 80 reviews

Wonderful country house

MichaelRating, 5 stars1 week ago
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.
Guest favorite
The image depicts a tranquil swimming pool with sparkling turquoise water, reflecting the surrounding greenery and a distant stone building. Tall cypress trees line the area, enhancing the serene landscape, while sun loungers are arranged neatly near the pool's edge.
Home in Asciano
4.94 out of 5 average rating, 36 reviews

Family Forest - Pool in the Crete Senesi

JánRating, 5 stars1 week ago
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
Superhost
The outdoor space features a sparkling swimming pool surrounded by a stone terrace. Sun loungers are arranged along the edge, while a lush green lawn and trees provide a natural backdrop. Scenic views of the countryside are visible beyond the pool area.
Home in Asciano
4.88 out of 5 average rating, 144 reviews

A Charming House in Asciano - Siena

CristinaRating, 5 stars8 months ago
Very nice place with a great view, very quiet and relaxing. The apartment was clean and cozy. The only inconvenience were the squeaky doors.
Guest favorite
A private pool is set within a well-kept garden, surrounded by lush greenery and gently sloping grass. The octagonal pool is framed by stone pathways and features a small tree at its center. The tranquil outdoor space invites relaxation and enjoyment.
Home in Gaiole in Chianti
4.86 out of 5 average rating, 264 reviews

Charming estate with views

AndrewRating, 5 stars2 weeks ago
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.
Top guest favorite
A large swimming pool surrounded by a brick patio and manicured lawns is highlighted in this image. Sun loungers are positioned along the pool's edge, with lush greenery and trees creating a serene backdrop. The villa's charming structure is visible in the distance under a partly cloudy sky.
Home in Barberino Tavarnelle
4.97 out of 5 average rating, 72 reviews

Podere Tignano, 4-bedroom villa in the Chianti!

MeganRating, 5 stars3 weeks ago
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

Guest favorite
The villa is positioned on a hillside, offering panoramic views of the rolling Tuscan countryside at sunset. Olive trees are scattered throughout the landscaped garden, with a covered terrace visible, inviting outdoor relaxation and dining. Warm light bathes the scene, enhancing the natural beauty.
Home in Castelmuzio
4.93 out of 5 average rating, 42 reviews

Casa Ora d"Oro - Panoramic Views

Jason AllenRating, 5 stars3 weeks ago
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!
Guest favorite
A charming countryside building is surrounded by lush greenery and rolling hills. A circular pool is situated in the garden, accompanied by several lounge chairs. A shaded seating area offers a relaxing spot, with trees and olive groves enhancing the serene landscape.
Home in Siena
5 out of 5 average rating, 9 reviews

the chestnut house

CarolaRating, 5 stars3 weeks ago
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!
Top guest favorite
A charming stone structure is framed by well-maintained greenery and steps leading to a welcoming entrance. Two wooden doors are set within the brick façade, complemented by a small garden area filled with plants, creating a serene outdoor setting under a clear blue sky.
Home in Siena
4.96 out of 5 average rating, 81 reviews

Oliveta Verde with garden near the center

NickRating, 5 stars3 months ago
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
Top guest favorite
The bedroom features a spacious bed with a patterned bedspread. A wooden headboard adds warmth, complemented by two small bedside lamps. Large windows allow natural light to fill the space, with views of the surrounding landscape. Two paintings adorn the walls, enhancing the room's charm.
Home in Poggibonsi
4.92 out of 5 average rating, 59 reviews

Agriturismo Podere San Martino (apartment for two)

LukasRating, 5 stars1 month ago
Everything was just like in the pictures. We had a great time. The view was amazing and Maddalena was really helpful. Thank you!
Superhost
A warm living area features arched windows allowing natural light to fill the space. A wooden coffee table is positioned in the center, surrounded by a comfortable sofa and a rattan chair. Shelving units display decorative items and a small plant sits atop the table.
Home in Lucignano
4.83 out of 5 average rating, 41 reviews

La Casetta

JonasRating, 5 stars2 weeks ago
Hard to find a place like Maria’s, beautiful place and with such a friendly and helpful staff.
Superhost
A private terrace features a wooden deck overlooking a panoramic view of the valley, with a steaming Jacuzzi positioned nearby. Sunlight filters through the trees, illuminating the area, while a cozy blanket and a few fruits are placed on the edge of the deck.
Home in Castelnuovo di Val di Cecina
4.93 out of 5 average rating, 68 reviews

L'Uva Fragolina. House, Garden, Panoramic View

DavidRating, 5 stars3 weeks ago
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!
Top guest favorite
A dining table is set outdoors with plates of pastries, fresh fruit, and drinks. Surrounding greenery adds to the serene atmosphere. In the background, rolling hills and a clear blue sky are visible, completing the inviting scene for outdoor dining.
Home in Poggibonsi
4.97 out of 5 average rating, 34 reviews

Casa Iris (with jacuzzi) - Close to San Gimignano

YasminRating, 5 stars3 weeks ago
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!
Guest favorite
A spacious loft area features a floral-patterned bedspread on a large bed, under exposed wooden beams. A bedside table and decorative lamp add warmth to the space. A glimpse of a bathroom can be seen through an open door, enhancing the room's comfort and functionality.
Home in Siena
4.94 out of 5 average rating, 71 reviews

Bright loft in the heart of Siena!

RachaelRating, 5 stars1 month ago
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

Guest favorite
A spacious two-story villa is set against a clear blue sky, surrounded by green grass and trees. A rectangular pool lies to one side, reflecting the sunlight, while a shaded patio area with seating is visible in front of the house.
Home in Buonconvento
4.97 out of 5 average rating, 87 reviews

S.Ilaria - Private pool Villa with 2 bedrooms

AlisonRating, 5 stars3 weeks ago
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!
Guest favorite
The image captures a tranquil outdoor area featuring a swimming pool surrounded by well-maintained grass and foliage. A shaded structure offers seating beside the pool, with steps leading into the water visible. Rolling hills and clear blue skies are seen in the background.
Home in Sovicille
4.94 out of 5 average rating, 78 reviews

Cozy country house Podere Scorno with pool

Rating, 5 stars1 week ago
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!!!
Guest favorite
An outdoor dining area features an elegantly round table surrounded by six chairs, offering stunning views of the rolling Tuscan hills. The space is shaded by a pergola, with decorative elements including colorful glasses and a vase of flowers placed on the table.
Home in Rosennano
4.93 out of 5 average rating, 80 reviews

LA RONDINAIA. AMAZING VIEW ABOVE THE CHIANTI

KaterinaRating, 5 stars1 week ago
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!
Top guest favorite
The image captures a stone villa surrounded by lush greenery and mature trees, creating a serene outdoor environment. The building's rustic architecture is complemented by terracotta roofs. Sunlight filters through the leaves, casting soft shadows on the sun-drenched ground.
Home in Monte San Savino
5 out of 5 average rating, 33 reviews

Beautiful villa with pool in secluded location

NeilRating, 5 stars8 months ago
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!
Top guest favorite
A rustic kitchen area is nestled against a stone wall, featuring a wooden bar table with two round stools. Minimalistic shelves hold kitchen essentials, while light streams through a window, illuminating the space and connecting it with the adjoining sleeping area.
Home in Montemassi
4.96 out of 5 average rating, 50 reviews

Capezzuolo 33

BenRating, 5 stars2 weeks ago
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!
Guest favorite
A stone facade is viewed from a well-maintained garden, featuring lush green grass and neatly trimmed hedges. A wooden door is visible, leading into a charming interior, while the house's rustic architecture complements the serene landscape under a clear blue sky.
Home in Castellina in Chianti
4.98 out of 5 average rating, 99 reviews

Explore Chianti from a Charming Stone House

ShelbyRating, 5 stars1 week ago
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.
Top guest favorite
A private swimming pool is framed by a sun terrace furnished with several white loungers. A shaded seating area provides a relaxing spot nearby, surrounded by lush greenery and trees. Natural stone steps lead along the edge of the space, enhancing the tranquil outdoor setting.
Home in Montevarchi
5 out of 5 average rating, 25 reviews

Casa San Ripa: Relax Oasis with Private Pool

CarolinaRating, 5 stars6 days ago
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!
Top guest favorite
A scenic view of rolling green hills stretches across the horizon, dotted with trees and farmland. A patio umbrella and lounge chairs are positioned outside, inviting relaxation. The sky is partly cloudy, with soft sunlight illuminating the landscape.
Home in San Giovanni d'Asso
5 out of 5 average rating, 62 reviews

Country chic house in a village,private pool,wiFi

PennyRating, 5 stars1 month ago
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!

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Province of Siena
  5. House rentals