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House vacation rentals in Poggibonsi

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Popular amenities for Poggibonsi house rentals

House rentals with a pool

Guest favorite
A shaded outdoor dining area features a large table surrounded by several chairs, nestled under a pergola with lush greenery. The shared swimming pool glistens in the background, framed by terracotta tiles and scenic views of the Tuscan landscape.
Home in San Miniato
4.93 out of 5 average rating, 134 reviews

Private villa/swimming pool in Tuscany

MārcisRating, 5 stars3 weeks ago
Everything was absolutely perfect! ⭐️ Location: Ideal base for exploring Tuscany — you’re right in the heart of it all. Whether you’re heading to Florence, Pisa, or the charming hill towns, everything is within easy reach. House: Well-equipped and comfortable, with all the listed amenities in perfect working order. After long days of sightseeing, the pool was a refreshing retreat. The panoramic view over the valley is truly breathtaking. Host: Lorenzo is an outstanding host — friendly, responsive, and fluent in English. He was proactive and helpful throughout our stay. The house includes a detailed guidebook he created with handpicked recommendations for local shops, markets, restaurants, farms, and sights. It made planning our days effortless. Bottom line: If this listing is available — don’t hesitate. Book it. 10/10 would recommend!
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!
Top guest favorite
A rustic dining area is highlighted by a long wooden table surrounded by several chairs. A vase of sunflowers sits at the center. The stone wall adds warmth to the space, while a clock and decorative items provide an inviting touch.
Home in Bagno A Ripoli
4.95 out of 5 average rating, 140 reviews

Casetta Melograno – Cozy farmhouse in Chianti

JacobRating, 5 stars1 week ago
I don’t have the words to describe how beautiful this apartment on the hillside is. The apartment itself is nice and cosy and spacious, and the kitchen contains a little bottle of olive oil produced from their own olives. But it is the location, the gardens and the little farm and the view across the valley which can take your breath away. Sonia is happy and welcoming and patient. She showed us around the wine and olive farm and was always approachable when we contacted her. There are two guest apartments side by side, but it is quite private nonetheless. Note that you can hear sounds from the other apartment quite easily. I cannot recommend this enough! Would love to come back.
Guest favorite
A private pool is surrounded by sun loungers, set on a wooden deck. The pool area features natural stone paving and is enclosed by a child-proof fence. Lush greenery and olive trees outline the space, providing a serene environment for relaxation.
Home in Lecchi in Chianti
4.96 out of 5 average rating, 138 reviews

Casa di Lyndall - Entire house with exclusive pool

LiannaRating, 5 stars1 week ago
Yet another fabulous stay! Thank you Lyndall for sharing your special space. Getting in on the village pizza night was a surprise bonus and so fantastic to enjoy the local community. Until next time :)
Guest favorite
Home in Rigomagno
4.96 out of 5 average rating, 101 reviews

House Rigomagno Siena

LucyRating, 5 starstoday
A fantastic place to stay! Diego is extremely welcoming and gave us great recommendations and local info. The house and garden are even more beautiful than the photos - everything well-equipped, all that we needed. We had the perfect, peaceful week and look forward to coming back!
Superhost
A stone pathway leads to a charming rustic building, surrounded by greenery and blooming flowers. To the side, a flat stone table under a large tree provides a serene outdoor space, inviting relaxation amidst nature.
Home in Rietine
4.85 out of 5 average rating, 208 reviews

Gaiole in Chianti Poggio Casabianca

AlexRating, 5 stars1 month ago
Valeria and Simone have a super nice and clean apartment! We felt very comfortable right from the beginning. The apartment offers a great starting point for numerous hikes and excursions. During our stay, we always got good tips and advice from the two. Our dog also felt very comfortable and since the property is completely fenced, he was able to move freely. We would come back back. It was an incredibly beautiful time!
Guest favorite
A rectangular private pool is surrounded by a grassy area and olive trees, providing a serene outdoor setting. Six lounge chairs are placed neatly around the pool, offering space for relaxation. The sky is partly cloudy, enhancing the natural beauty of the surroundings.
Home in San Miniato
4.92 out of 5 average rating, 104 reviews

Lovely house in a scenic and paiceful location

BiancaRating, 5 stars1 week ago
We enjoyed Maria's great house. We were kindly welcomed by Maria and her family, where we were welcomed with a bottle of wine and delicious cake. We were with 6 adults. There's plenty of room. It's nice that every bedroom has its own bathroom. It is a beautiful house in a beautiful area with a wonderful swimming pool between the olive trees and it is really equipped with every comfort. Very nice is also the charger for the electric car. We picked up fresh bread every morning from the local baker in the village 5 minutes away by car. Good base for the beautiful cities such as Lucca, Siena, Florence. The beach is also great. We felt very much at home. Maria and family, thank you for the great time in your beautiful home.

Weekly house rentals

Superhost
A charming dining area features a wooden table set for meals, surrounded by light-colored chairs. A colorful sofa is positioned against the wall, complemented by a decorative table. Framed art adorns the walls, while a chandelier adds elegance to the rustic wooden beams overhead.
Home in Poggibonsi
5 out of 5 average rating, 6 reviews

Villa Mocarello "IL CIPRESSO"

SandroRating, 5 stars14 months ago
The apartment exudes a delightful blend of love and tasteful design. The host’s attentiveness adds an extra layer of warmth to the experience, while the extraordinary environment creates a truly memorable stay.
Top guest favorite
A private pool is surrounded by lush greenery and flowering shrubs, inviting relaxation. Lounge chairs are positioned nearby under the shade of trees, creating a serene outdoor space. The pool area is accessible, providing a peaceful retreat for guests.
Home in San Gimignano
4.98 out of 5 average rating, 41 reviews

Tuscany:Stone house, private pool and garden

MarceloRating, 5 stars1 week ago
This house is the perfect place for two families traveling together. It’s incredibly cozy, thoughtfully designed, and fully equipped with amenities that let you truly enjoy the beauty of the Tuscan countryside. From the moment we arrived, we felt at home. The hosts went above and beyond — welcoming us with fresh fruit, traditional sweets, bottled water, coffee, milk, and a selection of Tuscan wines, which we truly appreciated. They also provided high-quality Italian hygiene products, which added a thoughtful and luxurious touch to our stay. One of the highlights for us was the host’s responsiveness. Communication was always fast, helpful, and friendly — a detail that made a big difference. We didn’t get a chance to use the private pool due to our tight schedule, but the property still gave us a real sense of independence, comfort, and safety. I 100% recommend this property. It’s a peaceful, beautiful place — perfect for relaxing, connecting with nature, and creating memories
Top guest favorite
Home in Pontassieve
4.96 out of 5 average rating, 83 reviews

The charming cottage in Tuscany with breathtaking views

PoojaRating, 5 stars2 days ago
Stella is a beautiful person and a perfect host. Everything immediately felt like home. She explained everything very nicely. The location was serene and she gave a lot of information on things to do in that area. Would love to come again for sure.
Top guest favorite
A charming stone exterior reveals a rustic villa surrounded by greenery. The entrance features a wooden door and terracotta roof tiles. Potted plants add color, while seating areas are positioned on a patio, inviting relaxation in the scenic surroundings under a clear blue sky.
Home in Radda in Chianti
4.94 out of 5 average rating, 139 reviews

Casa Dante

SarahRating, 5 stars2 weeks ago
A wonderful peaceful place in Tuscany. Spent most of our evenings out on the balcony, admiring the beautiful view. Home was well appointed and comfortable inside, and the host was very responsive to any questions or issues. Radda was also lovely, with good food, wine and a local tap room with interesting options! Would strongly recommend a stay here.
Superhost
A serene outdoor space is featured, showcasing a swinging bench accompanied by two white chairs. Lush green hedges surround the area, creating a private atmosphere. Terracotta tiles provide a warm flooring, inviting guests to relax and enjoy the natural surroundings.
Home in Poggibonsi
4.86 out of 5 average rating, 14 reviews

casa palme

LeslieRating, 5 stars2 weeks ago
Alessandra and her husband made us feel at home from the moment we walked into their home. It was absolutely beautiful! The boys loves playing hide and seek in all of there hidden compartments. I loved the view from their swing. Alessandra went above and beyond helping us with anything we needed. She even brought over a thermometer and medication when I told her I wasn’t feeling well. Her kindness and compassion meant so much to my family and I. I truly don’t have enough words to describe how grateful I am to have found this beautiful rental.
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!
Top guest favorite
A spacious living area is presented, featuring a contemporary sectional sofa adorned with cushions. The room is highlighted by a stone accent wall and a modern fireplace. Large windows provide natural light, while a round coffee table sits centrally, enhancing the inviting feel of the space.
Home in Monteroni d'Arbia
5 out of 5 average rating, 14 reviews

Golden View - Dream farmhouse in Tuscany

KshitijaRating, 5 stars6 days ago
This has to be one of the nicest Airbnbs we’ve stayed it. The accommodation was luxurious in an absolutely stunning area of Tuscany. The rolling fields and cypress tree made a spectacular setting for this beautiful house. We had hired a car and this place was a 20 minute drive from Siena. Our only regret was not staying here longer.
Guest favorite
A warm dining area features a wooden table surrounded by classic chairs. Natural light filters through large windows, showcasing the stone walls' texture. A staircase leads to an upper level, enhancing the open and inviting space.
Home in Castelnuovo Berardenga
4.91 out of 5 average rating, 195 reviews

THE BREATHE.Molino di Canonica. Original Apartment

MichaelaRating, 5 stars3 weeks ago
We expected a very nice, special accommodation, where everything necessary was available. We felt very comfortable. Due to the narrow streets, unfortunately, we could not ride the bikes as often, but with the car, we explored the area extensively and visited the many beautiful cities. We can definitely recommend the place.

Private house rentals

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
Top guest favorite
A scenic view features a natural pool surrounded by lush greenery and blooming flowers. Rolling hills extend in the background under a clear sky, creating a serene outdoors atmosphere. A tall tree provides shade nearby, enhancing the tranquil setting.
Home in Poggibonsi
5 out of 5 average rating, 19 reviews

Casetta nel Chianti – Poggio di Villore

AlexRating, 5 stars6 days ago
Silvia's house in Tuscany was an absolute dream – lovingly furnished, well maintained and with a stunning view over the hills. The tranquility, nature and unique surroundings make the place a real oasis. We particularly liked the beautiful garden, the natural pool and the authentic atmosphere of the house. Silvia and her family were warm, helpful and always available. Thank you so much for having us!
Guest favorite
An outdoor seating area is surrounded by lush greenery and colorful flowers, featuring a decorative ladder against the wall. A sunny terrace showcases terracotta tiles, with expansive views of the rolling hills in the distance, framed by a partially open canopy.
Home in Tavarnelle Val di Pesa
4.93 out of 5 average rating, 71 reviews

Top rated.pool, Hot Tub, homeGym & private Garden

ClaudioRating, 5 stars1 week ago
Absolutely gorgeous property with country side view and a cozy outdoor area, plus two friendly black cats! Louise was the perfect host: friendly, generous, attentive, she even offered to help us out when we had a setback that was totally unrelated to our stay at her property. Highly recommend to any traveller seeking an idyllic stay in the Tuscan countryside!
Top guest favorite
The image showcases the exterior of an ancient stone building within the historical walls of San Gimignano. Sunlight illuminates the textured facade, highlighting the charming architectural details, including windows and balconies. A quiet pathway leads to the entrance, surrounded by greenery.
Home in San Gimignano
4.98 out of 5 average rating, 80 reviews

Casa Maurino

KatieRating, 5 stars1 week ago
Loved Rosanna’s place, there was everything we needed and even food/wine there on my late arrival! The place was in THE BEST location and the view from the quiet terrace was perfect. Aircon worked a dream and it was great value for money. It’s in a beautiful part of the town and Le Vecchie Mura was a perfect restaurant 2 mins away. Totally recommend staying here; the place and town are magical.
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!
Guest favorite
A charming stone barn features a wide entrance with wooden pillars, framed by vibrant yellow flowers in the foreground. Steps lead to the door, surrounded by lush greenery and a serene landscape, highlighting the peaceful atmosphere of the Tuscan countryside.
Home in San Gimignano
4.98 out of 5 average rating, 46 reviews

La Moraiola - Characteristic Tuscan barn

LinasRating, 5 stars2 days ago
Egizia’s home was the ideal place for our family’s Tuscan getaway. It had everything we needed. Egizia was an excellent host, great communicator, great recommendations. We would stay here again.
Guest favorite
An expansive infinity pool is surrounded by lush greenery, reflecting the clear blue sky. Sun loungers are positioned along the pool’s edge, inviting relaxation. The gentle slopes of the Chianti countryside provide a serene backdrop, enhancing the tranquil outdoor setting.
Home in Barberino Tavarnelle
4.97 out of 5 average rating, 69 reviews

Chianti House Stunning view 20 min. from Florence

ThompsonRating, 5 stars4 days ago
Tommaso was very responsive and fantastic! Check in was a breeze. The pool was great. Overall, it was a great stay for our trip in Tuscany!
Superhost
A charming country building with a peach-colored exterior is surrounded by lush greenery. Umbrellas cover outdoor tables, while chairs are arranged on the grassy area. Towering trees provide shade, creating a serene outdoor setting.
Home in San Gimignano
5 out of 5 average rating, 3 reviews

Affordable farmhouse room

ClaireRating, 5 stars3 days ago
I had the most beautiful time at Poggio Muleti. I felt right at home. It was so peaceful and was exactly what I needed. I would recommend this stay to anyone and everyone. I can’t wait to visit again

Quick stats about house rentals in Poggibonsi

  • Total rentals

    10 properties

  • Nightly prices starting at

    ﺩ.ﺇ220 before taxes and fees

  • Total number of reviews

    270 reviews

  • Wifi availability

    10 properties include access to wifi

  • Popular amenities

    Kitchen, Wifi, and Pool

  • Local attractions

    Coop, Pam Barberino Val D'Elsa, and Centro Commerciale Valdelsa

Destinations to explore

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