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Villa vacation rentals in Poggibonsi

Find and book unique villas on Airbnb

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Popular amenities for Poggibonsi villa rentals

Private villa rentals

Guest favorite
An aerial view showcases a modern villa surrounded by lush greenery, featuring a private infinity pool. Lounge chairs are positioned beside the pool, and the outdoor dining area is elegantly set on a spacious terrace, enhancing the outdoor living experience.
Villa in Palaia
5 out of 5 average rating, 9 reviews

Villa La Gemma

DeryaRating, 5 stars7 months ago
The stay was wonderful! The villa was amazing, the views, the furniture, the rooms and the pool. We were so happy to be there. The rooms were new and clean. Every detail was taken care of. Christina was incredibly helpful and always available. Without her, we'd be lost. Unfortunately, we often had private problems and every time she helped us and brought us solutions. For me and my friends, this stay was unforgettable!
Superhost
A scenic pathway leads through a lush green landscape, bordered by flowering lavender and vibrant red blooms. The pathway is flanked by neatly trimmed trees, creating a serene and inviting atmosphere that connects the property to the natural surroundings.
Villa in Poppi
4.8 out of 5 average rating, 5 reviews

Villa for 22 people w/private pool

Marie-ClaireRating, 5 stars7 months ago
This little hamlet was ideal for a group of several families wanting a Tuscan holiday. Christina was a very responsive host, always available for help and suggestions. One down side was the distance from many of the Tuscan attractions such as Florence and Sienna. The hamlet is reasonably remote so is ideal for those who want a secluded holiday rather than those who want to see the sights of Tuscany.
Guest favorite
A large private swimming pool features clear turquoise water, surrounded by sun loungers and umbrellas. Olive trees are visible nearby, and a traditional farmhouse stands in the background against a clear blue sky, providing an inviting outdoor space for relaxation.
Villa in Baco
4.86 out of 5 average rating, 83 reviews

Tuscan Villa

DeeRating, 5 stars7 months ago
Five friends made to feel very welcome to this beautiful spacious villa with a lovely pool set amongst olive groves. The scenery that surrounded us was beautiful. Invited to Mark's villa who shared his knowledge and history of the olive groves which was very interesting and the hospitality received was first class (vino and yummy bruschetta's). This was the perfect place to stay and would highly recommend.
Guest favorite
Villa in Casale
4.96 out of 5 average rating, 24 reviews

Villa with pool in chianti Rufina area 13 sleeps

AnnaRating, 5 stars1 week ago
The house was amazing, perfect fit for our group of 10 people. The main house as well as the additional apartment were very clean, well equipped with everything you need and the highlight was the pool and jacuzzi. Great place to calm down and have private space with some friends or a big family. The check-in was easy and the lady was very friendly, had some suggestions for our stay and is professional. The property was clean, cute tuscany decorations of the rooms and all in all it felt like home.
Superhost
The spacious living room features a decorative ceiling with ornate detailing. Various art pieces adorn the walls, while elegant furnishings are arranged throughout. Natural light streams in through several windows, creating a bright and welcoming environment accented by carefully curated decor.
Villa in Florence
4.88 out of 5 average rating, 16 reviews

Villa La Cingallegra

MiltonRating, 5 stars6 months ago
Fantastic all around experience. Thank you Elio and team 🙏🙏
Guest favorite
A well-kept garden area is visible, featuring a stone table surrounded by lush greenery. The structure is framed by mature trees, providing shade and a sense of tranquility. Arched windows of the villa can be seen in the background, offering glimpses of the interior.
Villa in Pian di SCO
5 out of 5 average rating, 26 reviews

Villa il Palagio in the Tuscan countryside

LizRating, 5 stars7 months ago
Stunning home in the middle of a lovely vineyard (Probably one of the best homes on AirBnB). It's even more beautiful in person - full of art, thoughtful design/luxury finishes, and Tuscan charm. Highly reccomend!!
Superhost
A charming stone farmhouse is set against a clear blue sky, framed by lush greenery. In the foreground, a private saltwater pool reflects the vibrant flowers in planters on the wooden deck, creating a serene outdoor scene ideal for relaxation.
Villa in Provincia di Arezzo
4.91 out of 5 average rating, 43 reviews

Villa near Florence: Pool, AC, Vast natural garden

JackRating, 5 stars8 months ago
Stunning villa in a beautiful setting. Francesco gave excellent directions & the peace & tranquility out in the Tuscan countryside was wonderful. Francesco was exceptionally responsive & gave great local advice. We loved the little towns nearby and can’t wait to return soon. Highly recommended. Jack.
Guest favorite
A stone villa is illustrated with large windows and an expansive terrace. A well-manicured lawn stretches to a sparkling pool, complemented by sun loungers. Lush greenery surrounds the area, enhancing the serene outdoor space.
Villa in Gaiole in Chianti
5 out of 5 average rating, 9 reviews

Casa Faraona, villa with private pool

VaughanRating, 5 stars6 months ago
A beautiful property in a stunning location with great views. The property was easy to find using Waze. Once inside everything was clean and all rooms were luxurious and clean.

Luxury villa rentals

Top guest favorite
A welcoming living area is characterized by elegant furniture, including a pair of intricately designed chairs and a spacious couch. A decorative coffee table sits in the center, surrounded by soft natural light from the windows, and a vintage chandelier hangs above.
Villa in Rignano sull'Arno
5 out of 5 average rating, 10 reviews

villa "La Fonticina"

Salvador EsquedaRating, 5 stars3 days ago
Our stay at this beautiful Tuscany villa was truly unforgettable. The home perfectly blends charming, traditional Tuscan character with all the modern amenities we could possibly need. From the moment we arrived, we were enchanted by the authentic details — rustic beams, stone walls, and stunning countryside views — all while enjoying updated comforts like a fully equipped kitchen, high-speed internet, and luxurious bathrooms. It was the perfect balance of old-world charm and contemporary convenience. We couldn’t have asked for a better place to experience the magic of Tuscany. Highly recommend!
Top guest favorite
Villa in San Miniato
4.88 out of 5 average rating, 40 reviews

Historic home with exclusive pool

AylaRating, 5 stars9 months ago
We (7 girlfriends) enjoyed the stay in the villa very much! The house, especially the front yard and pool, are wonderful. Maria is great! She has sent us a lot of tips about the area (also the necessary things, such as shopping). In addition, we were surprised with a very fine cake and if you needed anything, there was a very quick response. The villa is well equipped and the surroundings beautiful. Parking has enough. Only the potholes and the access to the villa are a bit challenging - but doable!
Superhost
A spacious living area features a classic design with elegant seating arrangements, a round coffee table, and a decorative rug. Large windows allow natural light to illuminate the room, while offering views of the terrace and garden beyond.
Villa in Fiesole
4.86 out of 5 average rating, 22 reviews

Villa Lualdi

SallyRating, 5 stars7 months ago
Had a lovely week at the villa. Amazing place and beautiful views! Florence a short drive away, but we also enjoyed walking about 35 minutes to Fiesole for restaurants and views.
Guest favorite
The villa is set on a hillside, surrounded by lush olive groves and cypress trees. Its traditional architecture features a terracotta roof and stone walls. Outdoor seating areas invite relaxation, while pathways lead through well-kept gardens that reflect the area's natural beauty.
Villa in Colle di Val d'Elsa
4.95 out of 5 average rating, 21 reviews

Villa L 'elsa

MarcelaRating, 5 stars1 week ago
The house is amazing and the exterior is beautiful
Superhost
The expansive garden features well-maintained grass and elegant trees casting shadows on the ground. In the background, the villa's rustic brick facade complements the natural surroundings, while additional greenery and an open sky create a serene atmosphere.
Villa in Torrita di Siena
5 out of 5 average rating, 4 reviews

Villa Scianellone

NickRating, 5 stars35 months ago
We had an excellent time staying at this family home with an amazing view of Torrita di Siena. Great access to many popular hill towns (Cortona, Montepulciano, Pienza, Montalcino, etc). The house and property are beautiful, very private and populated with song birds and olive trees. The hosts are charming and very welcoming. They provided us with all the recommendations we needed and were readily available whenever we wanted to communicate with them. The house is well appointed and has multiple ways to cook from gas range to pizza oven and wood fired grill. I really liked using the giant pinecones as fire starter. We would definitely return and hope to. Such a precious slice of paradise.
Top guest favorite
A shaded seating area is positioned adjacent to a sparkling pool, surrounded by lush gardens and olive trees. Comfortable wicker sofas with soft green cushions invite relaxation, while sun loungers positioned under umbrellas enhance the outdoor leisure experience. Scenic views of the countryside are visible in the distance.
Villa in Cavriglia
4.99 out of 5 average rating, 128 reviews

Villa Poggio in Mandria in Chianti

EmilyRating, 5 stars6 months ago
We spent a week at Villa Poggio a Mandria as part of a group of six adults and had the most incredible and magical time. The photos do not do justice to how extraordinary the villa and surrounding area are — it’s nestled in an olive grove near the top of a hill just a short walk from a medieval village (Montegonzi), with utterly spectacular views in every direction. It could not be more peaceful or breathtaking. The villa was spotless, gorgeous and fully equipped, with tons of space for everyone. We had an unforgettable day with Lorenzo (contact available through Claudia and Leonardo), a local tour guide and chef who took us on an amazing wine tour and then cooked us the best meal ever that evening. And Claudia and Leonardo are the kindest, most responsive hosts, always available to answer any questions we had and even baking us a beautiful cake one evening! We can’t recommend Villa Poggio a Mandria enough. We had an unforgettable trip that truly felt like a dream. Thank you!
Top guest favorite
Villa in Orentano
4.98 out of 5 average rating, 97 reviews

Villa Gourmet Food, Pizza, Chef, Pool and Nature

EmilyRating, 5 stars1 week ago
My family and I had a fabulous week of vacation in Stephano’s wonderful Tuscan house! You could not find a better host than Stephano, he went out of his way to help us find places to eat, tour guides and taxi drivers. The pizza lesson with chef Guido was a great experience for all ages. And the homemade meal was simply amazing, served by chef Fabrizio and his warm, smiling helpers. The house was perfect too, very spacious, comfortable and well-equipped. I highly recommend this house and experience for anyone who wants to discover the region and its culinary specialties, in a warm and welcoming home.
Top guest favorite
An outdoor pool area is framed by an archway, featuring a clear blue pool surrounded by lounge chairs. Tall cypress trees and lush greenery rise in the background, complementing the serene, natural landscape.
Villa in Gaiole in Chianti
5 out of 5 average rating, 47 reviews

Sestuccia

RebeccaRating, 5 stars6 months ago
We had a marvelous stay at Villa Sestuccia. The house is spacious, as are the grounds. Both are well maintained. There is ample room with different areas to relax indoors and outside. We communicated with Briggita who was quick to respond, always friendly and always helpful. We particularly liked the location which has easy access to many spots of interest and restaurants. We enjoyed collecting eggs in the morning for our breakfast - such a fun touch. We highly recommend Villa Sestuccia and would not hesitate to stay here again.

Villa rentals with a pool

Guest favorite
The exterior of the villa showcases a brick façade supported by wooden columns. A well-maintained lawn extends alongside the building, bordered by a rustic wooden fence. The serene landscape in the background highlights trees and open fields under a clear blue sky.
Villa in Montepulciano
4.91 out of 5 average rating, 122 reviews

Villa in Montepulciano with a Pool

LindaRating, 5 stars2 weeks ago
We had a wonderful time in Tuscany! We were able to make use of the pool on the first day with our two boys, 7 and 4. We visited Pienza, Montepulciano and Montelccino. We also purchased two of the wines from the estate. Alex made everything very easy and was a great host!
Superhost
Villa in Petrognano
4.86 out of 5 average rating, 7 reviews

Villa Iris with Swimming Pool

KateRating, 5 stars7 months ago
I have so much positive to say about this place! Despite what some reviews mention about the drive, it's absolutely worth it. There's a small restaurant just 2-3 minutes away, easy access to the city, and you're only about an hour from Pisa and some beaches. The house was perfect—everything well thought out and worth every penny. The pool was amazing, and the host was very responsive. If you're visiting in autumn or spring, bring warm clothes for the chilly evenings. We were sad to leave, and I can't wait to come back to this dreamy property!
Superhost
Villa in San Casciano In Val di Pesa
4.83 out of 5 average rating, 30 reviews

Poggio degli Ulivi, charming Chianti with pool

MicaelaRating, 5 stars8 months ago
The stay was beautiful. The view is fantastic, the pool very clean, surrounded by a beautiful, huge garden. Breakfast on the terrace is fantastic as the kitchen goes right to the terrace. The house is beautifully decorated and very clean. the air conditioning works perfectly, the nearest supermarket can be reached by car in less than 15 minutes, as well as there are various restaurants that can be reached in less than 20 minutes by car. Like that of The Sor Paolo or the Barrachina.
Superhost
Villa in Greve in Chianti
4.83 out of 5 average rating, 29 reviews

Romantic Villa with private pool and fabulous view

RobertRating, 5 stars4 days ago
We absolutely enjoyed our stay. It felt like home from day one. The views are phenomenal; the garden is peaceful and fragrant. The kitchen is a delight to cook in. We walked into the beautiful village of Panzano multiple times (some hills which helped us burn off the pasta calories!). We didn’t want to leave.
Guest favorite
Villa in Toscana
4.88 out of 5 average rating, 60 reviews

Chianti Villa at Mulino del Cerchiaio

MathildeRating, 5 stars7 months ago
Thank you!! We enjoyed our vacation with 9 friends! A little humid because of the weather, but the place is ideal in summer and comforting by the fire when the good weather is not present!
Top guest favorite
An outdoor space features a rectangular swimming pool surrounded by a stone patio. Sun loungers and a dining table with chairs are positioned under a large umbrella. Lush greenery and flowering plants enhance the scenic view of the hillside in the background.
Villa in Ortignano Raggiolo
4.94 out of 5 average rating, 69 reviews

Private Villa with swimming pool in Tuscany

TomášRating, 5 stars6 months ago
We had a wonderful stay at the villa in Tuscany and felt at home right away. The hosts, Silvana, Iacoppo, and Bruno, took excellent care of us and were always attentive to our needs. The villa itself is spacious and well-equipped with everything one could ask for. The beautiful pool with its stunning views and the cozy fireplace area were definite highlights. It was the perfect place to unwind and enjoy the Tuscan countryside. Thank you again for an unforgettable stay!
Superhost
The image showcases an ancient stone villa surrounded by a spacious lawn, with a private swimming pool in the foreground. The pool is characterized by a rounded shape, complemented by white lounge chairs positioned nearby. Lush greenery and rolling hills are visible in the background under a partly cloudy sky.
Villa in San Gimignano
4.79 out of 5 average rating, 24 reviews

Elisa Villa

DominiqueRating, 5 stars6 months ago
Beautiful house in the vines surrounded by sumptuous hillsides in an incredible postcard setting. Perfect for gatherings for families or with friends. The location is ideal to radiate between Siena, Florence and Chianti or resting while enjoying the pool. Elisa, always attentive, is very responsive and will respond almost without delay.
Guest favorite
Villa in Volterra
4.98 out of 5 average rating, 51 reviews

Villa Casa al Povero

AnthonyRating, 5 stars2 weeks ago
I don’t even know where to begin describing this place. It was the most amazing place I have ever stayed. If you are looking for a peaceful and private villa with incredible views, then stop looking. This is it !! All of the reviews we read before we arrived talked about how amazing the views are and that you must take up the offer if Paola and Alessandro offer to cook a meal for you. Both recommendations are spot on. The sliced beef was one of the best meals I have ever had, and I often found myself wandering around outside the villa looking at the 360 degree views in all directions. We all felt so sad to leave this magic place. Paola and Alessandro were perfect hosts. Always friendly and with a smile on their faces. It’s a long way from Australia but I really hope we get an opportunity one day to return to this majestic place.

Destinations to explore

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