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Villa holiday rentals in Casole d'Elsa

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Quick stats about villa rentals in Casole d'Elsa

  • Nightly prices starting at

    Casole d'Elsa holiday rentals start at £180 per night before taxes and fees

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Casole d'Elsa rentals

  • 5 Average rating

    Casole d'Elsa stays are highly rated by guests – averaging 5 out of 5!

Top-rated villa rentals in Casole d'Elsa

Guests agree: these villas are highly rated for location, cleanliness and more.

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Guest favourite
An inviting kitchen space is highlighted by an arched brick entry. A large wooden dining table is set in the foreground, adorned with a decorative centerpiece. The kitchen features modern appliances, including a silver refrigerator, and warm lighting enhances the rustic ambiance.
Villa in San Miniato

Tuscany Country House Villa Claudia

Experience the enchantment of our Country House: a prestigious old Tuscan farmhouse, finely restored, with breathtaking views of the village of Canneto (785 AD). Surrounded by the greenery of San Miniato and equipped with every modern luxury, the villa is an exclusive retreat for regeneration. Choose between total relaxation in the Jacuzzi in the garden, excellent food and wine tours or visits to the nearby Tuscan cities of art. An unforgettable sensory experience between history and nature. Book your dream holiday in Tuscany!

4.94 out of 5 average rating, 134 reviews
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, 256 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, 106 reviews
Guest favourite
Villa in Monteriggioni

Villa of the 2 Olive Trees (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 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, 127 reviews
Top guest favourite
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, 138 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, 107 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.

4.98 out of 5 average rating, 120 reviews
Top guest favourite
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

Beautiful and ancient country house, located just 10 km from Siena (15 minutes by car from the city center). The house can accommodate up to 8 people. Surrounded by greenery, in a panoramic position with a beautiful garden where there is a hot tub, available, on request, even in winter. The very large property is fully fenced and offers maximum privacy. Please note: the hosts are also the owners and managers of the "Borgo dei Fondi" holiday home in Siena.

4.96 out of 5 average rating, 104 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, 191 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, 221 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, 311 reviews

Popular amenities for villa rentals in Casole d'Elsa

KitchenWifiPoolFree parking on premisesAir conditioning

Private villa rentals

Top guest favourite
The image showcases a rustic stone farmhouse surrounded by lush vineyards and olive trees. The building features a classic roof with terracotta tiles, set against a clear blue sky. Green grass frames the scene, emphasizing the natural beauty of the countryside.
Villa in Impruneta

Podere Scaluccia Chianti Agritourism, Florence

4.99 out of 5 average rating, 123 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
Superhost
Villa in Casole d'Elsa

Panoramic villa & private pool-VacaVilla Exclusive

4.67 out of 5 average rating, 9 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

Casale Piscina & View of San Gimignano By TripCare

4.77 out of 5 average rating, 31 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 private swimming pool is surrounded by a spacious stone patio, featuring comfortable sun loungers and shaded seating areas. Potted plants are placed around the pool, enhancing the tranquil outdoor space that is framed by trees and the rustic charm of the stone house.
Villa in Volterra

Romantic Villa with private pool - "Il Pollaio"

5.0 out of 5 average rating, 48 reviews
Guest favourite
Villa in Siena

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

5.0 out of 5 average rating, 22 reviews
Top guest favourite
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

Leo's Romantic House

5.0 out of 5 average rating, 66 reviews

Luxury villa rentals

Top guest favourite
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

4.99 out of 5 average rating, 131 reviews
Guest favourite
A serene view of a crystal-clear swimming pool is featured, with comfortable lounge chairs arranged around it. In the background, a charming stone villa is set among lush greenery, providing a peaceful ambiance. The area is well-maintained, emphasizing an inviting outdoor setting.
Villa in Orentano

Charming Villa in Stone in Tuscany, Borgo ai Lecci

4.97 out of 5 average rating, 116 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, 100 reviews
Guest favourite
An outdoor area is shown featuring a serene pool surrounded by well-maintained gardens. A wooden gazebo with seating is visible, alongside sun umbrellas offering shade. Olive trees and lush greenery create a picturesque backdrop against rolling hills.
Villa in Buti

Villa sii felice

4.96 out of 5 average rating, 56 reviews
Guest favourite
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
Top guest favourite
An aerial view captures a charming stone villa surrounded by lush greenery and neatly arranged gardens. A spacious swimming pool is visible, complemented by outdoor seating areas and pergolas, all against the backdrop of rolling hills and cloudy blue skies.
Villa in San Gimignano

Tuscan Villa with Pool & Jacuzzi, San Gimignano

4.98 out of 5 average rating, 90 reviews
Top guest favourite
An arch adorned with blooming wisteria frames a lush garden, featuring greenery and vibrant flowers. A terracotta pot sits nearby, while a picturesque tower rises in the background, adding a historic charm to the tranquil outdoor setting.
Villa in Florence

Villa Holm stunning view 10 mn walk to city centre

5.0 out of 5 average rating, 56 reviews
Superhost
Villa in Casole d'Elsa

Rustic house w/ private pool & garden near Siena

4.56 out of 5 average rating, 16 reviews

Villa rentals with a pool

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, 41 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

4.72 out of 5 average rating, 58 reviews
Guest favourite
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
Guest favourite
A rustic Tuscan farmhouse, restored with care, features a tall tower and expansive windows. Surrounding greenery includes cypress trees and shrubs, complementing the natural landscape. The lawn offers open space for relaxation, enhancing the serene atmosphere of the property.
Villa in Buonconvento

Beautiful tuscan country house

4.88 out of 5 average rating, 25 reviews
Superhost
The historic stone house, featuring a multi-level design, is surrounded by lush greenery. A spacious outdoor area includes a large lawn and a shaded terrace. The rustic architecture is complemented by details such as wooden shutters and a stone well.
Villa in Volterra

Ulimeto Power

4.9 out of 5 average rating, 77 reviews
Top guest favourite
The villa is depicted with a stone exterior, surrounded by olive trees and rolling vineyards. A circular pool is featured in the foreground, offering a tranquil spot for relaxation. Umbrellas provide shade over lounge chairs nearby, enhancing the serene outdoor space.
Villa in Radda in Chianti

Villa with pool in Chianti - Castellare Petroso

5.0 out of 5 average rating, 33 reviews
Guest favourite
An inviting swimming pool is bordered by lush greenery, with sun loungers and a shaded seating area nearby. The elegant villa stands in the background, featuring large windows and a traditional design, surrounded by tall cypress trees against a clear blue sky.
Villa in Castelfranco di Sotto

Villa Montefalcone: Charm, Private Pool, and Chef

4.98 out of 5 average rating, 42 reviews
Top guest favourite
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

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