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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

Villa Padronale - IlVillinoFarmhouse

Intero piano superiore della Villa Padronale appena ristrutturata in stile tradizionale toscano.Gli alti soffitti con le travi a vista rendono il posto accogliente e perfetto per famiglie o gruppi di amici.Nella casa si trovano due grandi camini(in salotto e cucina)funzionali.Alloggio privato, non condiviso. La casa ha una ampia terrazza coperta,giardino con divani,bbq,firepit,parking privato. La piscina tra gli ulivi e i vigneti e' ideale per il relax ha un accesso privato alla zona condivisa

4.93 out of 5 average rating, 254 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 si trova a circa 8 minuti di auto dal centro di Greve in Chianti, in Località Casole, nel cuore della splendida campagna del Chianti. La villa è situata in una zona tranquilla e silenziosa, all’interno di una piccola azienda agricola circondata da vigneti e uliveti, dove gli ospiti possono godere della natura e dei tipici paesaggi toscani. La posizione è ideale per chi desidera rilassarsi immerso nella campagna ma allo stesso tempo essere vicino al centro di Greve in Chianti

4.85 out of 5 average rating, 179 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 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

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, 137 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

La Torre

Antica villa toscana, bellissima, con giardino privato esclusivo, completamente ristrutturata, immersa nelle splendide e dolci colline toscane. La villa ha una vista mozziafiato, molto soleggiata, ben arredata e dotata di tutti i comfort, silenziosa e non isolata. La casa si trova a Bagnolo, piccola frazione di Impruneta alle porte del Chianti, zona di uliveti, vigneti e pace. La casa si trova a circa 10 km in macchina dal centro di Firenze.

5.0 out of 5 average rating, 188 reviews
Guest favourite
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, 307 reviews
Top guest favourite
A well-maintained garden surrounds a refreshing pool, bordered by manicured grass. A comfortable seating area, featuring two lounger chairs and a shaded umbrella, provides a serene spot for relaxation. Soft greenery and flowering shrubs form a natural backdrop, enhancing the tranquil atmosphere.
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, 207 reviews
Top guest favourite
Villa in Barberino Tavarnelle

Luxury Villa in Chianti • Private Natural Pool

Escape to your private Tuscan paradise in the heart of Chianti. Relax by a unique natural pool with a sandy beach, unwind in the jacuzzi and Turkish bath, and enjoy sunset aperitifs at your private beach bar. Surrounded by olive groves, Tenuta Virgilio offers complete privacy just 20 minutes from Florence and close to Siena and San Gimignano. An unforgettable luxury retreat for families and friends.

5.0 out of 5 average rating, 30 reviews

Popular amenities for villa rentals in Tavarnelle Val di Pesa

KitchenWifiPoolFree parking on premisesAir conditioning

Private villa rentals

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

Villa storica con piscina privata in Toscana

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

Guardia di Badia a Passignano

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
Villa in Barberino Tavarnelle

Three-Bedroom semi-detached Villa in Chianti

4.98 out of 5 average rating, 66 reviews
Guest favourite
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
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 Pistoia

Chiesino Dei Vaioni

4.99 out of 5 average rating, 86 reviews
Top guest favourite
A spacious bedroom features a four-poster bed draped with soft fabric. Two bedside lamps create gentle illumination. An arched bookshelf filled with books is visible in the background, alongside a cozy seating area with upholstered chairs, highlighting a mix of comfort and elegance.
Villa in Panzano in Chianti

Luxury Villa on Chianti Wine Estate

4.93 out of 5 average rating, 94 reviews

Luxury villa rentals

Guest favourite
Villa in Monteriggioni

Villa dei 2 Ulivi (Abbadia Isola)

4.97 out of 5 average rating, 174 reviews
Top guest favourite
Villa in Montepulciano

Wine Experience Villa in Montepulciano

4.97 out of 5 average rating, 125 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
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
The exterior of a charming stone villa is surrounded by a lush garden featuring vibrant lavender plants. Stairs lead to a welcoming entrance adorned with potted flowers and a shaded seating area. The rustic façade reflects traditional Tuscan architecture against a clear blue sky.
Villa in Chianciano Terme

Charming TuscanVilla with View for Family&Friends

4.97 out of 5 average rating, 128 reviews
Top guest favourite
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, 74 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
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 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
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
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
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
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, 40 reviews
Superhost
A wooden dining table is set under a pergola adorned with fabric shades, illuminated by warm evening light. The table holds decorative glassware and candles, while a vast green landscape extends toward the horizon, where the sun sets, casting a soft glow across the scene.
Villa in Terranuova Bracciolini

romignano wine farm

4.73 out of 5 average rating, 56 reviews

Destinations to explore