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Villa vacation rentals in Chiusdino

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Top-rated villa rentals in Chiusdino

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Guest favorite
A spacious kitchen showcases a large stone fireplace with a wooden mantle as its centerpiece. Light streams through the window, illuminating the wooden beams overhead. A dining table is set for a meal, while traditional utensils adorn the walls, enhancing the inviting ambiance.
Villa in Castellina in Chianti

Manor House - IlVillinoFarmhouse

Entire upper floor of the newly renovated Manor House in traditional Tuscan style. High ceilings with exposed beams make the place cozy and perfect for families or groups of friends. In the house, there are two large functional fireplaces (in the living room and kitchen). Private, non-shared accommodation. The house has a large covered terrace, garden with sofas, BBQ, fire pit, private parking. The swimming pool among the olive trees and vineyards is ideal for relaxation and has private access to the shared area

4.93 out of 5 average rating, 256 reviews
Top guest favorite
The stone farmhouse features vibrant red shutters and a terracotta roof. A spacious patio area contains a wooden dining set, surrounded by lush green grass and tall cypress trees. The exterior is complemented by well-maintained stone pathways, inviting guests to explore the outdoor space.
Villa in San Leolino

Poggio del Fattore-Villa with pool,hilltop,Chianti

Poggio del Fattore is situated at the eastern edge of the Chianti region in Valdambra, a green valley that joins the lands of Florence, Siena and Arezzo. The farmstead is on the top of an hill and lies at the end of a long private road through a large olive growing estate; therefore you absolutely need a car. The breathtaking landscapes and the location of the villa offer the privacy needed for a peaceful and relaxing holiday and a perfect departure point from which to explore central Tuscany.

4.99 out of 5 average rating, 131 reviews
Top guest favorite
A charming stone villa is set amidst a lush green lawn. The building features wooden window shutters and a terracotta tile roof. A covered porch, adorned with flower pots, offers a welcoming outdoor space, complemented by a backdrop of blooming plants and trees.
Villa in Barberino Tavarnelle

CasaDiManuela:TotallyPrivateChiantiVilla withTub

CasaDiManuela:TotallyPrivateVilla in Chianti withTub Jacuzzi The villa, immersed in the Chianti countryside, was obtained from an old farmhouse and then renovated with extreme care and attention to detail. Original terracotta floors and ceilings with ancient exposed beams, old traditional Tuscan furniture, flowery fabrics that dress beds and armchairs, paintings, antique china and lived objects recovered from markets and junk dealers will frame your living room. Nothing here is by chance.

4.97 out of 5 average rating, 106 reviews
Guest favorite
Villa in Monteriggioni

Villa dei 2 Ulivi (Abbadia Isola)

FULLY AIR CONDITIONED, modern 6BR/4BA VILLA on Via Francigena: an enchanted paradise for friends & families with kids (trampoline, basketball area, soccer & volley/beach tennis nets, fossball, table tennis) & w. pets (fenced garden). Located in the small village Abbadia Isola in the shadow of the medieval castle of Monteriggioni, right on the path the ancient road & pilgrim route running from France to Rome (via Francigena) A.k.A FAMILY GROUPS KIDS FRIENDS dream VILLA Siena 12mn (ABB)

4.97 out of 5 average rating, 174 reviews
Top guest favorite
The rustic two-story house is enveloped in lush green ivy, highlighting its stone façade. Two arched doors are framed by natural greenery, creating a harmonious appearance. An outdoor dining area with a table is partially visible under a shaded patio, providing a serene setting in the garden.
Villa in Sovicille

Beautiful Country House, near Siena with jacuzzi

Splendida e antica casa di campagna, situata a soli 10 km da Siena (15 minuti di auto dal centro città). La casa può ospitare fino a 8 persone. Immersa nel verde, in posizione panoramica con un bellissimo giardino dove è presente una vasca idromassaggio, disponibile, su richiesta, anche in inverno. La proprietà, molto grande, è interamente recintata e offre il massimo della privacy. Nota Bene - gli host sono anche proprietari e gestori della casa-vacanze " Borgo dei Fondi" a Siena

4.96 out of 5 average rating, 104 reviews
Top guest favorite
Villa in Montecatini Val di Cecina

Torre dei Belforti

Torre dei Belforti is the perfect place for people who love beauty, nature and art. Sleeping at the Tower is like traveling trough the time, between knights and princesses. The wonder of this place is enriched by a big garden, with its swimming pool, the cypresses alleys and the olive trees. The village is also a magic place well preserved and still alive. We are Emilia and Luca, we live here and our mission is to give the best to our guests, to fully enjoy this marvelous place.

4.99 out of 5 average rating, 138 reviews
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.
Villa in Barberino Tavarnelle

Podere Tignano, 4-bedroom villa in the Chianti!

Nestled among the rolling hills of Chianti between Florence and Siena, Podere Tignano offers breathtaking views over vineyards, olive groves, and golden grain fields. This charming Tuscan stone villa blends authentic rural character with modern comfort and welcomes up to 8 guests in 4 bedrooms. Surrounded by peaceful countryside and featuring a private swimming pool, it is the perfect retreat for those seeking relaxation, nature, and the true spirit of Tuscany.

4.98 out of 5 average rating, 107 reviews
Top guest favorite
Bright seating area features two white armchairs and a patterned ottoman, surrounded by large glass arches that open to a lush garden. Natural light floods the space, enhancing the exposed stone walls and wooden ceiling beams, complemented by a large potted plant.
Villa in San Casciano in Val di Pesa

Luxury Villa in the very heart of Chianti

The views, the views, oh my word the VIEWS! Originating in the early 12th century this spectacular home once served as the bakery for the entire village. Now fully renovated, the entrance and ground level have been opened with glass arches allowing natural light to illuminate the exposed walls, 4 large bedrooms, 3 with ensuite baths ( including a jacuzzi ). Only Minutes away from the famous Wineries of Chianti, this is THE Spot for a glass amongst friends.

4.98 out of 5 average rating, 120 reviews
Top guest favorite
A well-kept garden features neatly trimmed grass and a variety of trees, including tall pines, providing shade and a natural atmosphere. A subtle hammock is visible between two trees, inviting relaxation in the serene outdoor space.
Villa in Montespertoli

Farmhouse in Chianti

Beautiful portion of a farmhouse immersed in Chianti with a beautiful swimming pool, surrounded by vineyards and olive trees, perfectly furnished with a large garden and parking spaces. It is located 20 minutes from Florence, 40 from Siena and 50 from Pisa, in a few minutes you can reach Certaldo (birthplace of Boccaccio) and Vinci (birthplace of Leonardo Da Vinci). The house is halfway between Montespertoli and San Casciano (7km).

4.95 out of 5 average rating, 221 reviews
Guest favorite
Villa in Siena

Villa Capanna, Private Pool, Breathtaking Views

Ancient restored barn with up to 6 bedrooms and 6 bathrooms, immersed in a historic wine estate, just 6 km from Siena. One of the most beautiful views that the Tuscan panorama can offer, airconditioned bedrooms, exclusive swimming pool, large triple garden, BBQ, poolside table, terrace to enjoy the sunset over the medieval towers on the horizon while sipping the organic wines of the estate, fireplace, parking free, WI-FI internet.

4.89 out of 5 average rating, 311 reviews
Top guest favorite
Villa in Tignano

Villa Isabella

Villa Isabella is a comfortable Tuscan style villa located in the splendid Chianti hills in Tuscany with a large garden and a spectacular breathtaking panoramic swimming pool for exclusive use where you can experience the Tuscan tradition in full local style with the possibility of organizing private shuttles service for reach the property traditional experiences, services and tours only and exclusively for our guests.

4.96 out of 5 average rating, 209 reviews
Top guest favorite
Villa in Monteroni d'Arbia

"Villa Daisy" overlooking Siena

Wonderful villa with independent entrance inside the "Caggiolo" farm, brought to light with careful and thorough renovation that has kept intact the typical features of a Tuscan farm. Beautiful panoramic view of Siena. Located in Ville di Corsano, just 14 km from the city. An ideal place to spend days in total relaxation and enjoy the wonders that this area offers (Chianti, Val d'Orcia, Crete Senesi etc).

4.95 out of 5 average rating, 174 reviews

Popular amenities for Chiusdino villa rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Private villa rentals

Top guest favorite
A spacious patio area is surrounded by vibrant purple flowers and greenery, creating a serene outdoor environment. The rustic stone house features large glass doors, complemented by a shaded umbrella and seating area. A grassy lawn adds to the charm of this inviting setting.
Villa in Radicondoli

Casa di Leo Romantic House

5.0 out of 5 average rating, 66 reviews
Superhost
A historic country house is surrounded by lush green lawn, showcasing terracotta planters and seating areas under sun umbrellas. The sturdy brick facade highlights multiple windows and a prominent entrance leading to a charming garden space, blending rustic charm with serene outdoor living.
Villa in Chiusdino

Charming country house close to San Galgano Abbey.

4.84 out of 5 average rating, 37 reviews
Guest favorite
Villa in Siena

L'Apparita del Peruzzi | Villa | Private Pool & AC

5.0 out of 5 average rating, 22 reviews
Guest favorite
Villa in Badia a Passignano

Guardia di Badia a Passignano

4.86 out of 5 average rating, 7 reviews
Guest favorite
An aerial view captures the expansive countryside, dotted with vineyards and olive groves. The large swimming pool is framed by lush greenery, while the villa's garden offers a serene atmosphere. Gentle hills roll in the background under a clear, blue sky.
Villa in Poggibonsi

Villa with pool in Chianti Area

4.95 out of 5 average rating, 73 reviews
Guest favorite
Two comfortable loungers are positioned on a stone terrace, offering an expansive view of rolling green hills and the distant village of Roccatederighi. Sunlight streams across the scenery, while a small table holds a bottle and glass, inviting relaxation amidst nature.
Villa in Roccatederighi

Villa Casale "Il Diaccio" with views of the Maremma

4.94 out of 5 average rating, 18 reviews
Top guest favorite
An aerial view captures the charming layout of ancient stone houses surrounded by lush greenery and cypress trees. A swimming pool is visible, accompanied by well-maintained gardens featuring various relaxation areas. The surrounding landscape reveals vineyards and rolling hills typical of the Chianti scenery.
Villa in Castellina in Chianti

I CIPRESSINI DEL CASTELLACCIO (Cip 1 + Cip 2)

5.0 out of 5 average rating, 17 reviews
Superhost
A charming outdoor dining area is presented, featuring a round table surrounded by four wicker chairs with red cushions. A gentle sunset casts a warm glow, while the distant silhouette of San Gimignano towers over the lush green landscape in the background.
Villa in San Gimignano

Farmhouse with Pool & View of San Gimignano by TripCare

4.77 out of 5 average rating, 31 reviews

Luxury villa rentals

Superhost
A serene swimming pool is surrounded by lush greenery and rustic buildings. Several guests enjoy the cool water, while sun loungers offer a comfortable place to relax. Tall trees provide natural shade, enhancing the peaceful outdoor setting.
Villa in Greve in Chianti

Put down your luggage, this is just the beggining!

4.89 out of 5 average rating, 100 reviews
Guest favorite
A shaded terrace is presented with multiple wooden loungers arranged around a sleek pool. Lush greenery surrounds the space, offering a natural backdrop, while a stone building stands quietly in the distance under a clear sky.
Villa in Gaiole in Chianti

Casa Faraona, villa with private pool

5.0 out of 5 average rating, 32 reviews
Guest favorite
Villa in Monteroni d'Arbia

Panoramic villa in Crete Senesi, overlooking Siena.

5.0 out of 5 average rating, 53 reviews
Top guest favorite
A traditional Tuscan farmhouse is set against a backdrop of rolling hills. The property features a spacious pool surrounded by lush green grass and neatly trimmed hedges. Tall cypress trees provide natural framing, enhancing the serene outdoor atmosphere.
Villa in Montenero d'Orcia

Tuscany Villa With Pool & Magnificent Garden

5.0 out of 5 average rating, 39 reviews
Guest favorite
A sparkling pool is set in a well-maintained lawn, surrounded by tall trees and cypress plants. Comfortable lounge chairs are positioned beside the water, with a shaded area provided by an umbrella. The rustic villa can be seen in the background against a clear blue sky.
Villa in Asciano

Podere on the Crete Senesi

4.96 out of 5 average rating, 92 reviews
Top guest favorite
A serene outdoor area features a turquoise swimming pool surrounded by chaise lounges. Vibrant pink roses bloom near the edge, while lush greenery provides a natural backdrop. A stone villa with a tiled roof is visible in the distance, highlighting the tranquil setting.
Villa in Gaiole in Chianti

Sestuccia

4.99 out of 5 average rating, 76 reviews
Guest favorite
A charming stone villa stands surrounded by green grass and trees, featuring ivy-covered walls. The exterior is complemented by a pathway made of light-colored stones leading to seating arrangements. Clear blue skies are visible above, enhancing the tranquil outdoor setting.
Villa in Siena

The Villa of the Spendthrift Brigade!

5.0 out of 5 average rating, 28 reviews
Top guest favorite
An aerial view showcases a charming Tuscan farmhouse surrounded by lush vineyards and tall trees. The property features a private pool and a well-maintained garden, offering a serene landscape typical of the Chianti hills.
Villa in Noce

Villa in Tuscany with panoramic private pool

5.0 out of 5 average rating, 35 reviews

Villa rentals with a pool

Guest favorite
A heated mini hydro-massage pool is surrounded by greenery, featuring subtle chromotherapy lighting in shades of purple. In the background, a rustic farmhouse is set against a serene twilight sky, with tall cypress trees lining the space.
Villa in Monteroni d'Arbia

San Giovanni in Poggio, Villa Meriggio 95 sqm

4.98 out of 5 average rating, 128 reviews
Top guest favorite
The villa is situated in a lush landscape, surrounded by rolling hills and greenery. A private pool is framed by manicured hedges and lounging areas. The rustic stone structure features a covered patio and is complemented by nearby olive groves and trees, ensuring privacy.
Villa in Montecastelli Pisano

Exclusive villa with pool jacuzzi wifi and green

4.96 out of 5 average rating, 54 reviews
Guest favorite
An aerial view captures the villa surrounded by lush greenery and vineyards. The building features warm colors and tiled roofs. A shared swimming pool is visible nearby, set within the tranquil landscape, enhancing the serene countryside atmosphere.
Villa in Monsanto

Tenuta la Cipresseta | Casa Cipresso

4.98 out of 5 average rating, 41 reviews
Top guest favorite
Villa in Montaione

Private Villa with semi-Olympic pool and Tennis

4.98 out of 5 average rating, 50 reviews
Top guest favorite
A vibrant outdoor area features a pergola draped with greenery, providing shade over a comfortable seating arrangement. Flowering plants and shrubs surround the patio, enhancing the natural beauty of the villa's exterior, which exhibits warm hues under the sunlight.
Villa in Peccioli

Dream in Tuscany, Villa with pool

4.99 out of 5 average rating, 84 reviews
Top guest favorite
The villa's exterior features a two-story structure with a yellow facade and numerous wooden window shutters. A manicured lawn surrounds the building, providing an open space for relaxation. A small terrace is visible, as well as a tower with a flag, enhancing the charming setting.
Villa in Monteriggioni

Tenuta Uzielli an elegant countryside villa

5.0 out of 5 average rating, 20 reviews
Guest favorite
A charming outdoor space is surrounded by lush greenery, including flowering shrubs and aromatic plants. An umbrella shades a seating area, offering a serene escape. The stone structure is visible in the background, complemented by manicured grass and the gentle sway of nearby trees.
Villa in Poggi del Sasso

"La Capanna di Neri" stone farmhouse with swimming pool

4.96 out of 5 average rating, 56 reviews
Guest favorite
A kidney-shaped pool is surrounded by a well-maintained patio and lush greenery. Several lounge chairs, each with a white frame, are positioned around the pool. An umbrella provides shade over one seating area, enhancing the inviting outdoor space.
Villa in Montemassi

Private Villa with Swimming Pool and Hot Tub

4.94 out of 5 average rating, 35 reviews

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