Some info has been automatically translated. Show original language

Villa vacation rentals in Poggibonsi

Find and book unique villas on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Poggibonsi villa rentals

Private villa rentals

Guest favorite
A private swimming pool is framed by manicured lawn and positioned under two large umbrellas. Four lounge chairs are arranged around the pool, offering views of rolling hills and the Tuscan countryside beyond. The pool features a sleek, modern design with clear water reflecting the sky.
Villa in Gambassi Terme
4.96 out of 5 average rating, 54 reviews

Villa Via Francigena

BettyRating, 5 stars4 days ago
Beautiful surroundings, peaceful, beautiful pool! Extremely well-appointed kitchen. Hosts responded immediately if we had any questions.
Top guest favorite
An arch adorned with blooming wisteria frames a lush garden, featuring greenery and vibrant flowers. A terracotta pot sits nearby, while a picturesque tower rises in the background, adding a historic charm to the tranquil outdoor setting.
Villa in Soffiano
5 out of 5 average rating, 39 reviews

Charming villa 15' walk to center stunning view

RuthRating, 5 stars1 week ago
Incredible property with a breath taking view over Florence. Hard to put into words how perfect the property is but the best part of the whole experience was the hospitality Marco, Stefania Grinza Carota and Filippo! The best hosts imaginable made us feel so at home, welcome and a part of the family. Now we want to move to Florence
Guest favorite
A charming stone-crafted villa is set among lush greenery, with terraced levels adorned by landscaped gardens. A private pool with sun loungers is positioned in the lower terrace, while the villa overlooks rolling hills, providing a tranquil backdrop for relaxation.
Villa in Gaiole in Chianti
5 out of 5 average rating, 6 reviews

Casanova of Bricciano

PeterRating, 5 stars2 weeks ago
What a fabulous setting and location. Perfect to explore the Chianti region and beyond. It’s roomy, everything you need is there, beautiful pool and a view to cherish. Dining on the terrace is a wonderful experience and with a vinyard with lovely wines available right next door what more do you need from a Tuscan holiday. All hosted perfectly by Fabio and Andrea. Very highly recommended.
Top guest favorite
A private pool surrounded by lush greenery and natural stone walls is featured. Comfortable loungers are positioned on a tiled patio, offering a relaxing space under the open sky. Large glass doors lead into the cottage, inviting natural light into the area.
Villa in Gaiole in Chianti
4.93 out of 5 average rating, 27 reviews

Sestuccina

EmmaRating, 5 stars2 weeks ago
We had a lovely stay at this beautiful villa. The photos do not do it justice at all! From the infinity pool overlooking the vineyard to the hot tub with views of a castle, it was stunning and jaw dropping scenery. Brigittia made sure we were prepared to have a great trip - from helping us with reservations and arranging transportation for us with her husband (who was wonderful) she was a fantastic host. We would love to visit again sometime and would recommend for anyone wanting to spend time in the countryside.
Guest favorite
A shaded outdoor seating area is furnished with comfortable sofas and a stone table, surrounded by lush greenery and colorful potted plants. A hot tub is visible in the background, providing a tranquil setting with views of the picturesque landscape.
Villa in Asciano
4.93 out of 5 average rating, 88 reviews

Casa Bianca, a gorgeous Tuscan home in Crete Senesi

JulieRating, 5 stars1 week ago
Photos do not do justice to the amazing views. Very special place.
Superhost
A clear blue swimming pool is framed by a lush green lawn and colorful flowerbeds. Stone walls support the surrounding garden, which includes tall cypress trees and potted plants. Behind the pool, a rustic building with terracotta roof tiles adds charm to the landscape.
Villa in Poggibonsi
4.79 out of 5 average rating, 70 reviews

Charming poolside house

PaulRating, 5 stars2 weeks ago
We will definitely come back!
Top guest favorite
An outdoor dining area is set with a green stone table, featuring neatly arranged plates, silverware, and glassware. A blue ceramic pot and a bottle of wine are included. The background reveals an infinity pool overlooking a lush forest with rolling hills under a partly cloudy sky.
Villa in Gaiole in Chianti
5 out of 5 average rating, 24 reviews

Montemarcoli

TorbjørnRating, 5 stars2 weeks ago
We had an amazing stay at the villa. A modern house in quiet surroundings with beautiful views. Brigitta was very helpful and responded quickly to our inquiries both before and during the stay.
Top guest favorite
The villa's rustic stone exterior is complemented by a sunlit pool area, featuring a beautifully crafted wooden pergola. Comfortable seating arrangements are provided under the pergola, surrounded by blooming flowers. A large umbrella offers shade beside the shimmering pool, enhancing the outdoor relaxation experience.
Villa in Cavriglia
4.99 out of 5 average rating, 133 reviews

Villa Poggio in Mandria in Chianti

VaughnRating, 5 stars1 week ago
A beautiful place, beautiful surroundings, great hosts, great pool, just everything was perfect. Didn’t want to leave. Felt like home and couldn’t wait to get back there on the days we ventured out.

Luxury villa rentals

Guest favorite
A serene outdoor space is presented, featuring a black stone pool surrounded by lush green grass and trees. The villa's rustic structure is visible in the background, with a shaded area provided by a large tree. Sun loungers are positioned nearby for relaxation.
Villa in Castiglione d'Orcia
4.97 out of 5 average rating, 118 reviews

Wp Relais Borgo Vignalunga

SumeRating, 5 stars1 week ago
We had a lovely stay — the villa is absolutely beautiful and we had a great time enjoying the space and surroundings. The location is also ideal, close to stunning towns like Pienza. A few improvement points: there was no proper coffee-making equipment, just a few filters; the fireplace hadn’t been cleaned and had no firelighters; and the air conditioning didn’t work in about half the rooms. Also, the check-in wasn’t smooth — the time was moved to 16:00, but the cleaners were still busy when all 14 of us arrived. With a bit more attention to these details, it could be a truly exceptional stay.
Top guest favorite
A spacious bedroom features a four-poster bed draped with soft fabric. Two bedside lamps create gentle illumination. An arched bookshelf filled with books is visible in the background, alongside a cozy seating area with upholstered chairs, highlighting a mix of comfort and elegance.
Villa in Panzano
4.93 out of 5 average rating, 75 reviews

Luxury Villa on Chianti Wine Estate

StevenRating, 5 stars1 month ago
Wonderful stay at the Villa among the vineyards in Panzano. Vicky, the host, is the owner of Le Fonti winery with the villa surrounded by their vineyards and olive groves. The view from the villa is absolutely stunning. The town of Panzano is very cute. We bought groceries at the Coop and made breakfast each morning, gathering in the cozy well equipped kitchen. There is a courtyard immediately outside the doors of the villa with a large table, and again amazing views. Our time in the villa was so relaxing! Though we went to several wineries, a highlight was a very personal tour of the winery, wine making process and wines by Vicky at Le Fonti. She spent time discussing/pouring the different wines, even bringing over the same wine from different years to show us the difference the weather/grape stress influences the final taste. Overall exactly what we wanted from a Tuscan experience and really enriched by an extremely friendly and knowledgeable host.
Guest favorite
The exterior showcases a spacious garden area featuring several lounge chairs positioned on lush green grass. A stone pathway leads towards the welcoming entry of the two-story villa, framed by trees and flowering plants under a partly cloudy sky.
Villa in Siena
4.97 out of 5 average rating, 39 reviews

Capanna Di Elfo

MichaelRating, 5 stars3 weeks ago
The property was comfortable, spacious and spotlessly clean. The owners of the property , Claudio and Angelica, are helpful and delightful. However, the “host” BoMVillas , who acts as a middleman, was rude and disrespectful when we had a miscommunication. I would not make another booking that was offered by BoMVillas.
Top guest favorite
Villa in Sarteano
4.97 out of 5 average rating, 125 reviews

Stone farmhouse in the Val d'Orcia

Theng JuhRating, 5 stars1 week ago
Stefania was super nice to wait for us despite we were later for 3 hours. Her house was very beautiful and lots of space for 10 of us. Everyone can have their own space on the balcony or terrace. Can have BBQ too. House was very well equipped with everything that we expected. Had a wonderful time. Thank you.
Top guest favorite
Bright pink flowers frame a tranquil infinity pool, with rolling green hills visible in the background. The landscape is dotted with tall trees and stretches toward distant mountains under a clear blue sky.
Villa in Barberino Tavarnelle
5 out of 5 average rating, 36 reviews

Valluccia 51

FlorisRating, 5 stars1 month ago
We had an amazing time in the villa from Tommaso. It has all the amenities that you expect from a villa in this price class. The view looking over the valley is beautiful. The communication with the host was very pleasant and swift. As an example; The existing tv got broken in the evening and the next morning Tomasso installed a new one with all the modern features like Apple Airplay. Since the weather was not great the first days you can imagine that this was very nice to have a good working tv. Anyone who is considering renting a villa in the surrounding of San Donato, I highly recommend this villa from Tommaso.
Top guest favorite
A refreshed saltwater pool is surrounded by lush greenery and olive trees. Sun loungers in vibrant colors are positioned along the pool deck. A shaded area with a pergola is visible, providing a relaxing spot for guests to enjoy the serene landscape.
Villa in Monsummano Terme
4.98 out of 5 average rating, 125 reviews

Le Maggioline Your Tuscany country house

SarahRating, 5 stars2 weeks ago
We had the most wonderful stay at Olga’s place. We had 6 adults and two children and there was still plenty of space. The house was beautifully appointed and the outdoor space with the view was the perfect place to relax.
Top guest favorite
A modern kitchen area is seen, featuring white cabinetry and a stone backsplash. Kitchen appliances, including a microwave and coffee maker, are visible. A dining table with wooden chairs occupies the corner, while a comfortable sofa is positioned nearby. Warm lighting enhances the inviting atmosphere.
Villa in Montepulciano
5 out of 5 average rating, 48 reviews

Terra Antica Suite & Ville - Montepulciano

JohnRating, 5 stars1 month ago
Beautiful property. Staff were amazing, responsive and friendly. Location ideal for visiting other cities by car. Exactly as pictured. Breakfast which was added on a day to day basis was spectacular. Very relaxing sitting on patio and by the pool.
Top guest favorite
An aerial view captures the expansive Poggio del Fattore estate, showcasing lush greenery and neatly arranged olive trees. The two main buildings, characterized by terracotta roofs, are complemented by the blue of the swimming pool, surrounded by vibrant gardens and cypress trees.
Villa in San Leolino
4.99 out of 5 average rating, 109 reviews

Poggio del Fattore-Villa with pool, hilltop, Chianti

ElkeRating, 5 stars1 week ago
Our stay with Marta and her family could not have been nicer. We felt absolutely comfortable from the first moment. The property is absolutely spacious, lovingly equipped, incredibly well maintained and run with love. Marta and her family are absolutely lovely and take care of their guests very nicely. All your wishes are fulfilled. The pizza evening was wonderful and a successful end to our stay. If you are looking for a fantastic, secluded Tuscan ambience and loving hosts, "Poggio del Fattore" is the place to be.

Villa rentals with a pool

Guest favorite
Villa in Certaldo
4.89 out of 5 average rating, 18 reviews

Villa Gelsomino, your dream in Tuscany

LenaRating, 5 stars2 months ago
We were traveling with a group of 4 couples and 3 toddlers. And loved the place. Each couple had their own bathroom and everything was super clean. The entire complex was very well maintained. There was a tennis court, a soccer field, table soccer, volleyball and a great children's playground. The system could not be better equipped. In addition, the location of the accommodation is perfect for exploring Tuscany. We were completely satisfied and would come back immediately.
Top guest favorite
An aerial view showcases the Tuscan villa nestled within olive groves, with a private infinity pool reflecting the surrounding hills. The rustic architecture features terracotta roofs and a stone exterior, complemented by lush greenery and tranquil pathways leading to the entrance.
Villa in Cortona
5 out of 5 average rating, 75 reviews

Stunning Tuscan Villa & Panoramic Infinity Pool

CherieRating, 5 stars1 week ago
Immaculate villa with plenty of space for everyone. Exceeded our expectations. Remote location best for people who have a car however peaceful and very close to drive into town in 10 minutes. Amazing restaurants nearby. Spectacular views. Beautiful pool area. Attentive friendly hosts. Especially beautiful Elmo the dog.
Guest favorite
Villa in Buonconvento
4.95 out of 5 average rating, 57 reviews

Bellagatta, an Enchanting spot in Val d'Orcia

MartinRating, 5 stars8 months ago
We had an amazing four weeks staying at Bellagatta, using it as a base to explore Tuscany & surrounds, and it met all our expectations and more. Bellagatta is a positioned on a hilltop with stunning 360 degree panoramic views, more beautiful than the photos. The annexe that we stayed in was exceptionally clean and comfortable and well fitted out. Air con was useful on the first few days of our stay which were very hot. The property is well situated, 10 minute drive into Buonconvento (not quite an easy return walk up the hill!) which was convenient for restaurants & shopping. Gaetano was a most delightful host, very welcoming, & always taking interest in which towns we were travelling to and providing useful tips for our visits. His property manager, Susil, was also readily available and looked after us with anything we needed , even providing fresh eggs, vegetables & olive oil from the property. Highly recommended!
Top guest favorite
The exterior of the villa showcases a rustic stone facade under a clear blue sky. A swimming pool is visible in the foreground, with white lounge chairs positioned nearby. A covered patio area features a dining set, providing a welcoming space for outdoor relaxation.
Villa in Poppi
5 out of 5 average rating, 15 reviews

Villa Lux Poggelleri with a unique view of the Casentino

KasperRating, 5 stars2 weeks ago
We are a family of 5 who had a fantastic stay. The house is huge and very nice and the view is unbeatable. All stress leaves the body when you are there. Everywhere you looked, there were exceptionally beautiful views. In addition, Lucia and Frederico were so warm people and made us feel very welcome. We will definitely be back!
Superhost
Villa in Capannori
4.96 out of 5 average rating, 25 reviews

Luxury Tuscany Villa on the hill with private pool

EmmaRating, 5 stars3 weeks ago
We booked this for a girls holiday and we had the best week. We didn’t hire a car, we walked to a few of neighbouring towns and got a taxi to Lucca, and a train to Florence one day. Neighbouring towns have small supermarkets and the walks to them were enjoyable, the scenery is truly incredible. Lucca is beautiful and has incredible markets, it’s a must see if you stay here. The villa itself is exactly as shown in the pictures, the pool area is gorgeous, we sat around the table every night for dinner, and when it’s dark there’s clusters of fireflies sparkling in the roses, it was magical. Stefania was great, very responsive and there if we needed her. We’d definitely recommend and book this villa again in the future!
Guest favorite
Villa in San Gimignano
4.88 out of 5 average rating, 72 reviews

Lilium,delux farmhouse in the chianti hills

CharlotteRating, 5 stars2 weeks ago
We had a fantastic stay at Concetta's beautiful home! The house itself is gorgeous and traditionally Tuscan. It is also in the most incredible scenery and sitting outside and taking in the view was an absolute joy. However, by far the best thing about our stay was Concetta and her husband Paolo. They could not have done more to make us feel more at home and it honestly felt like we were part of the family while we were there (including making us the most incredible meal, which I would strongly recommend you do if you stay!) Their hospitality, helpfulness and warmth made it feel like a true escape and I could not recommend it more.
Top guest favorite
Villa in Volterra
5 out of 5 average rating, 23 reviews

Romantic Villa with private pool - "Il Pollaio"

ErinRating, 5 stars3 weeks ago
A beautiful home to base ourselves in while exploring Tuscany. Lovely country surrounds. House has everything you need, spacious. Gorgeous terraces and pool. Enjoyed Volterra, San Gimignano and Siena but always great to come back to our Tuscan home! Silvia gave fantastic recommendations - pasta making at Ristorante de Beppino and in house chef Beppe highlights. Also loved Monterosola winery tasting. Very highly recommend. One of the best!
Top guest favorite
A serene view of the stone farmhouse is captured against a bright blue sky. Lush greenery surrounds the property, featuring olive trees and vibrant foliage. A sparkling swimming pool is situated in the foreground, reflecting the natural beauty of the landscape.
Villa in Sinalunga
5 out of 5 average rating, 44 reviews

The twigs

NatalieRating, 5 stars2 weeks ago
Sandrine’s Airbnb was by far the best accommodation we’ve ever experienced—a peaceful paradise nestled in the hills of Tuscany. What made it truly unforgettable, though, was the incredible generosity of our hosts. Sandrine welcomed us with a warm smile and thoughtfully provided delicious food and drink throughout our stay. She also shared wonderful recommendations for places to visit and things to see. It was a true blessing to meet such kindhearted and gracious people. 🙏

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Province of Siena
  5. Poggibonsi
  6. Villa rentals