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Villa holiday rentals in Tavarnelle Val di Pesa

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Top-rated villa rentals in Tavarnelle Val di Pesa

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Guest favourite
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, 254 reviews
Top Guest favourite
The villa's exterior is highlighted by a modern structure with large glass doors and a gently sloping roof. It is surrounded by lush greenery and features a patio area with steps leading to the entrance. Soft lighting illuminates the garden, creating a serene evening ambiance.
Villa in Montepulciano

Amazing Tuscany Villa, FREE parking

Modern villa with panoramic view in Montepulciano, a few steps from San Biagio. The villa is lovingly furnished and equipped with all comforts for a pleasant holiday. Enjoy breathtaking views of the surrounding countryside from the terrace, or relax in the two spacious gardens at your disposal. You will also have at your disposal a large kitchen to dabble in the magnificent art of cooking, something much loved by us Italians!!! Also available: Free Wi-fi Self check-in Reserved car parking

4.92 out of 5 average rating, 331 reviews
Top Guest favourite
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, 105 reviews
Top Guest favourite
A sunlit pool area features a spacious salt-water pool with a surrounding deck. Several lounge chairs are arranged with umbrellas, providing shaded seating. A rustic stone building serves as a backdrop, displaying traditional Italian architectural elements and large windows that invite natural light.
Villa in Orentano

Villa Gourmet Food, Pizza, Chef, Pool and Nature

Villa Gourmet Typical farmhouse in the heart of Tuscany with 6 bedrooms that can comfortably accommodate up to 14 guests. - Exclusive saltwater infinity pool - Gourmet cuisine - Large garden with private parking - Two Free Charging Station (3,75 KW) - Veranda with table and Weber barbecue by the pool - Children's play area and table tennis - Football pitch - Home Restaurant service available - Cooking class and pizza workshop using a wood-fired oven - Shuttle Services

4.98 out of 5 average rating, 126 reviews
Top Guest favourite
A historic tower rises prominently against a blue sky dotted with fluffy clouds. Surrounding greenery complements the stone structure, with trees and small buildings visible along the hillside, collectively conveying a sense of tranquility.
Villa in Montecatini Val di Cecina

Belforti Tower

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, 137 reviews
Top Guest favourite
The pool is illuminated with soft lighting, creating a calming ambiance during the evening. Surrounding greenery provides privacy, and seating areas are visible. The smooth water surface reflects the gentle glow, inviting relaxation in a serene outdoor setting.
Villa in Monte San Savino

Villa Tonacato - Charming Villa with private pool

Ancient rural farmhouse, located on the Tuscan hills with views of the surrounding countryside. Isolated and ideal for those who want to relax but close to the main Italian tourist cities. Each room is equipped with air conditioners with windfree technology, in the living room there is an 82" ULTRA HD TV with SKY and international channels. The pool is equipped with Philips Hue lighting to create the right atmosphere at all times and a Bose Soundtouch bluetooth sound system

4.99 out of 5 average rating, 107 reviews
Superhost
The exterior of a charming stone villa is showcased, with a refreshing swimming pool in the foreground. Lush green grass surrounds the pool area, and a shaded gazebo with seating is positioned nearby. Rolling hills and a clear blue sky form a picturesque backdrop.
Villa in Greve in Chianti

Villa La Doccia, Greve in Chianti

Villa La Doccia is located about an 8-minute drive from the center of Greve in Chianti, in the area of Casole, in the heart of the beautiful Chianti countryside. The villa is located in a quiet and peaceful area, on a small farm surrounded by vineyards and olive groves, where guests can enjoy nature and the typical Tuscan landscapes. The location is ideal for those who want to relax in the countryside but at the same time be close to the center of Greve in Chianti.

4.85 out of 5 average rating, 179 reviews
Top Guest favourite
A heated jacuzzi is situated under a shaded pergola, surrounded by lush greenery and colorful flowers. The serene outdoor space is complemented by a gravel path leading towards vineyards in the background, inviting relaxation and privacy.
Villa in San Casciano In Val di Pesa

Il Vichiaccio: Florence Villa with Jacuzzi

Cozy Chianti Villa near Florence. This 135sqm stone house has a rustic kitchen with a fireplace. It sleeps 9 guests in 3 rooms, but for groups of 11, a 4th bedroom is included. Smaller groups can add it for extra comfort (extra fee). Enjoy the private garden with a covered dining area, a patio with armchairs and parking. The ground floor is fully wheelchair-friendly (kitchen, bedroom, bath). Plus, A/C and a private Jacuzzi (extra fee) for relaxing under the stars!

4.95 out of 5 average rating, 202 reviews
Top Guest favourite
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, 105 reviews
Top Guest favourite
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.

4.97 out of 5 average rating, 119 reviews
Top Guest favourite
An inviting villa surrounded by lush greenery and vibrant flowers, featuring blooming rose bushes and olive trees. The gravel pathway leads to the entrance, showcasing a two-story structure with balconies. Sunlight highlights the colorful landscape, creating a serene atmosphere.
Villa in Impruneta

The Tower

Ancient Tuscan villa, beautiful, with exclusive private garden, completely renovated, surrounded by the beautiful and gentle Tuscan hills. The villa has a breathtaking view, is very sunny, well furnished and equipped with all amenities, quiet and not isolated. The house is located in Bagnolo, a small hamlet of Impruneta at the gates of Chianti, an area of olive groves, vineyards and peace. The house is about 10 km by car from the center of Florence.

5.0 out of 5 average rating, 188 reviews
Top Guest favourite
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, 219 reviews

Popular amenities for Tavarnelle Val di Pesa villa rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Private villa rentals

Guest favourite
Villa in Monteriggioni

Villa of the 2 Olive Trees (Abbadia Isola)

4.97 out of 5 average rating, 174 reviews
Top Guest favourite
A tranquil pool area is highlighted by a clear blue pool flanked by sun loungers under white umbrellas. Lush greenery surrounds the property, with a charming farmhouse visible in the background, and inviting pathways guide guests through the scenic landscape.
Villa in Capannori

Farmhouse , pool, 13 px. Lucca 10km

4.99 out of 5 average rating, 148 reviews
Top Guest favourite
Villa in Barberino Tavarnelle

Luxury Villa in Chianti • Private Natural Pool

5.0 out of 5 average rating, 30 reviews
Top Guest favourite
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

Historic villa with private pool in Tuscany

5.0 out of 5 average rating, 35 reviews
Guest favourite
Villa in Badia a Passignano

Badia a Passignano Guard

4.86 out of 5 average rating, 7 reviews
Top Guest favourite
A charming entrance is framed by a wrought iron gate, opening to a gravel pathway leading to a spacious courtyard surrounded by greenery and stone buildings. Lush trees and flowering plants enhance the inviting outdoor space, reflecting the historical character of the restored barn.
Villa in Certaldo

Villa Gelsomino, your dream in Tuscany

4.94 out of 5 average rating, 32 reviews
Top Guest favourite
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

Valluccia 51

5.0 out of 5 average rating, 49 reviews
Top Guest favourite
Villa in Barberino Tavarnelle

Three-Bedroom semi-detached Villa in Chianti

4.98 out of 5 average rating, 66 reviews

Luxury villa rentals

Top Guest favourite
Villa in Montepulciano

Wine Experience Villa in Montepulciano

4.97 out of 5 average rating, 125 reviews
Top Guest favourite
The exterior of a charming villa is surrounded by lush greenery, with vines climbing along the walls. A gravel pathway leads to the entrance, framed by well-kept gardens. Sunlight filters through the trees, creating a peaceful atmosphere ideal for relaxation and outdoor gatherings.
Villa in Pergine Valdarno

La Vignaccia (Farmhouse) - villa w/private pool

4.96 out of 5 average rating, 101 reviews
Top Guest favourite
A vibrant yellow villa is framed by lush greenery, with a charming stone wall and an ornate wrought-iron gate. The main entrance showcases wooden shutters and a traditional tiled roof, inviting visitors into a serene and private setting.
Villa in Impruneta

Casa de' Miei – Garden Villa near Florence, Chianti

5.0 out of 5 average rating, 100 reviews
Guest favourite
Villa in Libbiano

Exclusive Tuscan Villa with private pool

5.0 out of 5 average rating, 16 reviews
Guest favourite
A clean and inviting swimming pool is surrounded by sun-drenched patio tiles, with a single lounge chair positioned nearby. Lush green trees and manicured hedges frame the area, enhancing the sense of tranquility and connection to nature.
Villa in Sambuca

Tuscan villa in Chianti Classico hills Il Poggiolino

4.92 out of 5 average rating, 71 reviews
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, 98 reviews
Top Guest favourite
Villa in Montaione

Private Villa with semi-Olympic pool and Tennis

4.98 out of 5 average rating, 50 reviews
Top Guest favourite
A shaded dining area is presented under a canopy, featuring a large table set for meals. In the background, a private swimming pool is visible, with sun loungers placed nearby and olive trees dotting the landscape beyond.
Villa in San Donato

Casa Colombaia, in the Chiantishire

4.96 out of 5 average rating, 95 reviews

Villa rentals with a pool

Top Guest favourite
A private swimming pool is surrounded by vibrant flowers and lush greenery. Multiple lounge chairs are positioned under umbrellas for shade. A seating area is visible in the background, along with a well-maintained pathway and rustic stone walls, enhancing the serene outdoor setting.
Villa in Poggibonsi

Villa L'Olivo w/Private pool (Close San Gimignano)

4.99 out of 5 average rating, 98 reviews
Guest favourite
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

La Cipresseta Estate | Cipresso House

4.98 out of 5 average rating, 40 reviews
Superhost
The villa is set amidst lush greenery, featuring a stone pool terrace that leads to a welcoming swimming pool. Sun loungers are positioned around the pool area. The structure, with multiple windows, showcases a harmonious blend of rustic charm and modern design against a clear blue sky.
Villa in Poggibonsi

Amazing Chianti villa with pool for 12

4.92 out of 5 average rating, 37 reviews
Guest favourite
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

Villa Via Francigena

4.96 out of 5 average rating, 72 reviews
Top Guest favourite
A serene swimming pool is framed by vibrant flower pots filled with red geraniums. Lush greenery surrounds the area, providing a tranquil atmosphere. A shaded seating area is visible in the background, enhancing the outdoor relaxation space.
Villa in Greve in Chianti

Villa San Martino 6-8 people

4.96 out of 5 average rating, 51 reviews
Superhost
A private swimming pool is framed by lush greenery and cypress trees, reflecting the stunning Tuscan landscape. The villa, constructed from natural stone, sits on a hilltop, offering a serene ambiance amidst olive groves. Blue water contrasts against the terracotta pool deck.
Villa in Greve in Chianti

STUNNING 5BR VILLA WITH POOL IN CHIANTI TUSCANY

4.79 out of 5 average rating, 34 reviews
Guest favourite
A private swimming pool is surrounded by lush greenery and blooming flowers. Lounge chairs are positioned along the pool's edge, with a shaded area featuring a sun umbrella and comfortable seating. The tranquil environment is created by the nearby trees and manicured bushes.
Villa in Florence

Villa with pool near the center of Florence

4.9 out of 5 average rating, 82 reviews
Guest favourite
Villa in Greve in Chianti

Charming Chianti Villa | Garden & Panoramic Pool

5.0 out of 5 average rating, 17 reviews

Destinations to explore