House vacation rentals in Poggibonsi

A shaded garden area features a hammock suspended from a tree and a round table with chairs, set against a backdrop of lush greenery and rolling hills. The panoramic view extends under a partly cloudy sky.

4.97 out of 5 average rating, 279 reviews

Charming converted Hayloft overlooking the Chianti Hills

Inspired by the rustic Tuscan style, this gorgeously refurbished hayloft features ceilings with exposed beams and bricks and thoughtful touches for a stylish and comfortable decor. From the relaxing hammock and the stone made barbecue in a panoramic garden to the cozy fireplace, every space feels open and inviting. Immersed in total peace and tranquillity with a breathtaking view over the Chianti hills, halfway between Florence, Arezzo and Siena, the barn is a perfect homebase to visit Tuscany. The accommodation has 2 floors. The upper floor spaces 2 double bedrooms with wonderful views of the olive trees and a bathroom with window and large masonry shower. On the ground floor a cozy and spacious living area with fireplace and a kitchenette with gas stove a large fridge and oven. The barn has ceilings with exposed beams and bricks. Outside there is a panoramic garden set on its own where, in the shade of a walnut trees, you can relax on a hammock or grill your meal (included an authentic local Fiorentina steak :-) on the stone made barbecue. A garden table is there for romantic dinners 'al fresco'. Immersed in total peace and tranquility halfway between Florence, Arezzo and Siena the barn is a perfect homebase to visit Tuscany. To find the exact location of the house type the following code in GMaps: 8FMHGG25+QV The house is in the countryside. The closest towns are Cavriglia and the small Medioeval villages of Moncioni and Montegonzi. In each town you can find great local restaurants and a small grocery shop. Moncioni is 3 km far away. A big supermarket is located in Montevarchi and you can reach it in 8 minutes by car ( exactly 7 km far away). In Montevarchi you can also find one of the best farmer markets in Tuscany! The station of Montevarchi is 8 km away from the barn. From there you can take train to Florence and Arezzo. Siena can be reached in 30 minutes by car. The easy access to the motorway A1/E35 Milan-Florence-Rome (the Valdarno exit is only at 13 km) allows you to reach numerous interesting spots within a short time, both in Tuscany and Umbria, while few kilometres south of Cavriglia you enter the suggestive territory of the Crete Senesi. Out in the countryside, the home offers an authentic experience of Tuscany. Small towns and villages are a short drive away providing acces to exceptional local restaurants and fantastic farmers markets. A big supermarket is located in Montevarchi (7 km far away). The railway station is 8 km away from the barn. From there you can take train to Florence and Arezzo. Cities of interest like Siena, Montepulciano, Pienza and Monteriggioni can be reached in 40 minutes by car The only way to reach the house is by car. A taxi service is active from Montevarchi You will be provided of blankets and towels. The kitchen is equipped with and kind of pots, pans, bowl, plates and silverware. You are welcome to use them. Free Netflix available

An outdoor patio area is featured, showcasing a spacious covered space with large, light curtains that gently sway in the breeze. Comfortable seating options consist of bean bags and a dining table, all surrounded by lush greenery and tall cypress trees.

4.97 out of 5 average rating, 132 reviews

Casa al Gianni - The Simignano Barn

Transformed from an old barn, this luxurious retreat offers 5 bedrooms, 4 bathrooms, large equipped kitchen, large living room and a large private garden with parking, hot tub, patio with sofas, BBQ, fire pit and outdoor kitchen. Ideal for those looking for a unique experience, it combines rustic charm with modern comforts. Perfect for families or groups, it promises magical evenings under the stars, between relaxation in the hot tub and outdoor dinners. A memorable getaway awaits you in this slice of paradise!

A charming pathway leads to the entrance of the house, surrounded by lush greenery. Flower pots are positioned along the stone walkway, with a seating area visible to the side, inviting guests to enjoy the serene landscape of rolling hills in the background.

5 out of 5 average rating, 156 reviews

Love in Chianti

Welcome to the delightful cottage of Riccardo and Pauline, a small corner of love where colors and details are designed to give peace and quiet. You will find yourself immersed in the green Tuscan hills, in a breathtaking landscape where the renowned Chianti Classico wine is born. The area is ideal for walking and cycling. You will be close to the cities of art, such as Florence, Siena and Arezzo. Upon request and according to availability, we offer a paid shuttle service. We look forward to seeing you ❤️

A charming garden area features a round table surrounded by four wrought iron chairs. Vibrant flowers bloom in planters, and lush greenery adds to the tranquil environment. A rustic stone wall and traditional rooftops provide a picturesque backdrop, enhancing the sense of privacy.

4.99 out of 5 average rating, 192 reviews

Garden House

"Casa del giardino" ...... a blooming oasis within the medieval walls.. The owners Mario and Donella would like to offer you a unique vacation in San Gimignano. You can enjoy the wonderful garden, an extraordinary oasis of peace and silence, in the city center, for the exclusive use of those who rent the apartment. Thus, reading a book, relaxing in the sun, sipping an excellent glass of Chianti or having breakfast surrounded by greenery and among the flowers of this garden will be a memorable experience!

A quaint terrace is presented with a small round table and two chairs. Potted flowers add natural color, while a beautiful view of rolling hills and vineyards is visible in the background under a clear blue sky.

4.98 out of 5 average rating, 446 reviews

Old Farmhouse near Panzano Castle Abbacìo

The Abbacio apartment is part of an old farmhouse that has been restored respecting the original structure and style. Its location is just on the top of the hill, facing the valley. Surronded by vineyards and olive trees, but also attached to the village. From the house you can easily reach by feet wineries, farms and restaurants. Panzano is halfway between Florence and Siena, easily reached with car. By bus there is a good service from and to Florence, not from and to Siena. A very quiet spot!

An aerial view of the property reveals a charming red house surrounded by lush greenery. Tall cypress trees and vibrant bushes create a tranquil landscape, while an expansive lawn features relaxing loungers, inviting guests to enjoy the serene atmosphere of the Tuscan countryside.

4.99 out of 5 average rating, 180 reviews

Il Fienile, Luxury Apartment in the Tuscan Hills

‘Il Fienile’ is in an enchanting position immersed in the beauty of the Tuscan hills, with a breathtaking view of the surrounding countryside. It is located in the hamlet of Catignano in Gambassi Terme, just a few kilometres from San Gimignano. The house sits in a protected oasis surrounded by a beautiful private park with olive trees, a pond, pine trees and woods, where you can walk, relax and enjoy the pleasures of unspoilt nature. A unique experience entirely to be enjoyed.

A lush green garden is framed by a rustic pergola made of wooden beams. Grassy paths lead deeper into the garden, where vibrant flowers and trees provide a natural backdrop. Rolling hills and a clear blue sky are visible in the distance, creating a serene outdoor setting.

4.98 out of 5 average rating, 112 reviews

StageROOM03 -Chianti Idillic Country living

Set in a picturesque hamlet, overlooking the Chianti hills, this charming country house is just 10 minutes from Siena and Castellina in Chianti. Recently renovated, it blends authentic Tuscan charm with modern comforts. The house features two bedrooms, two bathrooms, a cozy living area and a fully equipped kitchen with a dishwasher, two fridges, and a washing machine. Outside, enjoy a beautiful garden and relax in the outdoor marble hot tub, soaking in the breathtaking views.

A stone structure with a tiled roof is framed by greenery, surrounded by rolling hills. A spacious outdoor area features a wooden table, inviting relaxation. Large trees and thriving shrubs enhance the tranquil setting, with a backdrop of a serene sunset illuminating the landscape.

4.97 out of 5 average rating, 197 reviews

The Chianti Classico Sunset

If you are looking for an idyllic location in the heart of the classic Chianti, immersed in the vineyards and olive groves of the beautiful Tuscan hills, in the farm of a historic Villa of the ‘500, then come to our barn!! It has a dominating position with a stunning view, where you can enjoy breathtaking sunsets. The total independence of the house, the cozy garden, the large loggia allow you to spend stays in complete peace of mind. Our reviews are your best guarantee.

An exterior view showcases a charming suite with a terracotta facade. The entrance features large arched windows, while a patio is furnished with two cozy chairs and a small table surrounded by potted plants. A serene dog relaxes on the stone-paved terrace.

5 out of 5 average rating, 246 reviews

"La limonaia" - Romantic Suite

Romantic Suite immersed in the enchanting hills of Fiesole. It is the ideal place fot those looking for unique and exclusive experience of its kind characterized by suggestive views and unforgettable sunsets. The accommodation is part of an old 19th century Tuscan farmhouse surrounded by its own olive groves and woods. This is an ideal place for a relaxing holiday and privileged base for visiting the major centers of interest in Tuscany.

A spacious living area features exposed stone walls and a rustic fireplace with a television positioned nearby. A light-colored sideboard complements the warm tones of the wooden beams above. A dining table with red chairs is set beside large glass doors that open to a green outdoor space.

4.89 out of 5 average rating, 255 reviews

Tuscan Counrtry Detached House. Wi-Fi Free

Update: Air conditioning starting June 1st, 2025. Enjoy the summer with a cool breeze! Do you want to spend your holiday in a typical Tuscan barn? This is your place! Charming renovated barn for families / groups. Located in the heart of the Tuscan countryside at 2km from Poggibonsi. Ideal for a relaxing holiday and in a great location for visiting San Gimignano (13km), Siena (25km), Florence (35km).

A cozy living area features a vibrant striped sofa and rustic wooden beams above. Natural light streams through a skylight, illuminating the space, which includes a modern kitchen and a wooden dining table in the background. Decorative plants add a touch of greenery.

4.91 out of 5 average rating, 149 reviews

La Casa di Nada - Suite

Every window of my house opens onto wonderful views of the Tuscan hills, an enchantment that will accompany every moment of your stay. My kitchen is fully equipped and the rooms are comfortable and bright, with a private bathroom for each room. In the living room, I have a beautiful fireplace all for you. A practical, complete laundry room in this refuge in the Heart of Chianti

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.

4.98 out of 5 average rating, 100 reviews

Explore Chianti from a Charming Stone House

Awaken in a bedroom with beamed ceilings, open doors to a private garden, and take an early morning dip in the pool. Return to a classically designed house with terra cotta floors, wood-burning fireplace, and bathrooms with exuberant tile work. Casa Marinella is the perfect place to discover Chiantishire. Fully equipped kitchen, AC in each bedroom, private garden and barbecue.

Vacation rentals for every style

Get the amount of space that is right for you

Villas

Luxurious estates for the ultimate escape

Apartments

Convenient locations with everyday essentials

Hotels

Stylish accommodations and amenities

Popular amenities for Poggibonsi house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.87 out of 5 average rating, 103 reviews

Ancient Barn in Chianti with Pool

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.

4.93 out of 5 average rating, 136 reviews

Private villa/swimming pool in Tuscany

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.

4.86 out of 5 average rating, 265 reviews

Charming estate with views

Home in Lecchi in Chianti

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.

4.96 out of 5 average rating, 140 reviews

Casa di Lyndall - Entire house with exclusive pool

Aerial view of a rustic stone house surrounded by greenery and olive trees. A rectangular pool is visible, with turquoise water and purple umbrellas shading lounge chairs. The expansive garden features lush grass and landscaped foliage, providing a serene and spacious outdoor environment.

4.93 out of 5 average rating, 181 reviews

Collina Power

A serene stone pool reflects the clear sky, set against a backdrop of lush trees and rolling hills. The inviting water is framed by a stone deck, with a single umbrella providing shade nearby. The tranquil landscape offers a peaceful escape.

4.94 out of 5 average rating, 177 reviews

Antico Borgo Ripostena – n. 8 Old House

4.95 out of 5 average rating, 102 reviews

House Rigomagno Siena

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.

4.85 out of 5 average rating, 210 reviews

Gaiole in Chianti Poggio Casabianca

Show all

Weekly house rentals

A spacious terrace is furnished with a wooden dining table surrounded by six rattan chairs. An umbrella provides shade, while greenery enhances the natural setting. A distant view of rolling hills and historical architecture is visible under a clear sky.

4.99 out of 5 average rating, 129 reviews

Gorgeous Villa with Postcard Views in Historical Florence

The exterior view features a rustic stone house surrounded by greenery, including trees and flowering plants. Sun loungers are positioned on the lawn, creating a space for relaxation. A spacious terrace extends from the house, providing access to the inviting garden area.

4.99 out of 5 average rating, 165 reviews

Tuscany .Countryhouse on the Florence's hills

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.

4.98 out of 5 average rating, 41 reviews

Tuscany:Stone house, private pool and garden

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.

4.97 out of 5 average rating, 73 reviews

Podere Tignano, 4-bedroom villa in the Chianti!

A decorative wall shelf is embedded in a stone wall, featuring a small potted plant and a light fixture above. Below the plant, a set of wine glasses is arranged on a glass surface, adding a touch of elegance to the rustic backdrop.

4.96 out of 5 average rating, 247 reviews

House for the Coast

A spacious living area features a large white sectional sofa arranged around a coffee table. Two large windows draped with colorful curtains provide natural light and frame views of the outside. The rustic stone walls and wooden beam ceiling add warmth to the inviting space.

5 out of 5 average rating, 8 reviews

Podere le Fonti - Farmhouse 15 min. San Gimignano

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.

5 out of 5 average rating, 17 reviews

Golden View - Dream farmhouse in Tuscany

A cozy bedroom features a brass bed frame with soft white linens. A bedside lamp provides gentle lighting. A door leads to a bathroom, visible through an open space, showcasing a window that offers views of the surrounding countryside.

5 out of 5 average rating, 24 reviews

Private country house with garden, Wifi and A/C

Show all

Private house rentals

A private swimming pool is surrounded by a stone patio, featuring several lounge chairs arranged for sunbathing. Lush greenery and olive trees provide a natural backdrop, while the distant view showcases parts of the historic borgo. A shaded area is available for relaxation.

5 out of 5 average rating, 61 reviews

[Little Escape] 4 Beds + Private Panoramic Pool

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.

5 out of 5 average rating, 19 reviews

Casetta nel Chianti – Poggio di Villore

An elegantly decorated living room features a vintage sofa with decorative cushions situated on a colorful area rug. Natural light illuminates the space through two large windows. A modern chandelier hangs from the ceiling above a coffee table, surrounded by tasteful decor items and plants.

5 out of 5 average rating, 5 reviews

19th century villa near Florence, pool,guest asst.

A tranquil outdoor space features a clear swimming pool surrounded by lush greenery. Tall cypress trees line the perimeter, offering natural shade. The gently rolling hills in the background create a serene landscape, illuminated by soft morning light.

5 out of 5 average rating, 6 reviews

Villa of the Hydrangeas

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.

4.88 out of 5 average rating, 16 reviews

casa palme

A bright kitchen features a large wooden window overlooking a leafy garden. Fresh flowers are arranged in a vase on the countertop, accompanied by a bowl of eggs. Natural light enhances the space, highlighting the white cabinetry and sink area.

4.94 out of 5 average rating, 65 reviews

Countryhometuscany - House with Garden -

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.

4.91 out of 5 average rating, 69 reviews

L'Uva Fragolina. House, Garden, Panoramic View

A brightly lit bedroom features high wooden ceilings and a large window that offers natural light. A spacious bed with yellow and neutral-toned bedding is framed by two nightstands. A stylish wall mural depicting abstract patterns adds a unique touch to the inviting space.