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Vacation rentals in Villa

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Top-rated vacation rentals in Villa

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Top guest favourite
An outdoor patio area features rustic furnishings and is framed by gracefully draping curtains. The space is adorned with comfortable seating and a communal dining table, set against a backdrop of tall cypress trees and a clear blue sky, inviting relaxation in a serene environment.
Home in Simignano
4.97 out of 5 average rating, 192 reviews

Casa al Gianni - The Simignano Barn

Transformed from a former barn, this luxurious retreat offers 5 bedrooms, 4 bathrooms, a large, fully equipped kitchen, a spacious living room, a large private garden with parking, a hot tub, a patio with sofas, a BBQ, a fire pit, and an 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, including relaxation in the hot tub and outdoor dinners. A memorable getaway awaits you in this slice of paradise!

Top guest favourite
Home in Greve in Chianti
4.99 out of 5 average rating, 111 reviews

Relaxation and charm in the Chianti hills

Beautiful stone farmhouse, detached, surrounded by olive trees and the Chianti hills, with private garden and panoramic swimming pool. Ground floor with large living rooms, antique fireplace and wood-burning oven, bright living room and fully equipped kitchen. On the first floor, three suites consisting of a bedroom, study and private bathroom. Access via gate and white road on private property just 500 meters from the village of Strada in Chianti. Ideal for peace and relaxation. Convenient location for visiting Tuscany.

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
4.93 out of 5 average rating, 254 reviews

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

Guest favourite
Home in Barberino Tavarnelle
4.96 out of 5 average rating, 46 reviews

beautiful farmhouse in the Chianti area with panoramic garden

"BADIA A PASSIGNANO DWELLING" You will enjoy a relaxing and restorative stay in the heart of the Chianti Classico region. You will stay in a fully restored, ancient stone barn with a large fenced garden and an old gazebo, suitable for large groups and families. The rooms are comfortable and spacious for 8 people. The renovation was carried out with great care, taking into account every aesthetic detail to allow you to experience the ancient Tuscan tradition combined with comfortable modernity.

Top guest favourite
An aerial view showcases the expansive grounds of La settecentesca Villa di Geggiano, surrounded by manicured gardens and lush vineyards. The main villa is prominent, with a circular driveway leading to it, while gentle hills extend into the background.
Cottage in Geggiano
4.99 out of 5 average rating, 155 reviews

Villa di Geggiano – Guesthouse

PLEASE NOTE THAT BEING IN THE COUNTRYSIDE WITH FEW PUBLIC TRANSPORTATION OTHER THAN TAXI, THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A CAR. The 18th century Villa di Geggiano, surrounded by vineyards and lovingly cared gardens, is located in the Chianti area near Siena, one of the most beautiful regions of Italy which will provide an idyllic and enchanting backdrop to your vacation. Our guesthouse is located in one of the garden pavilions of the villa.

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
4.99 out of 5 average rating, 74 reviews

Sestuccia

Villa Sestuccia is a lovely Tuscan villa near the popular towns of Gaiole and Radda in Chianti. In this wonderful villa there are 4 bedrooms with private bathrooms.The exterior of the villa is composed by 4 living areas: the "wisteria living", the "panorama living", the "Mondrian living", the "outdoor patio" and a vegetable garden. There is also a swimming pool, a SPA and an outdoor hot tub for 6 people. Inside the fenced property you can find a chicken coop and a beautiful vineyard. Enjoy!

Top guest favourite
Home in Il Poggetto
4.93 out of 5 average rating, 152 reviews

The Loggia

Immerse yourself in the authentic Tuscan dream. "La Loggia" is a charming home in the heart of Chianti Classico, just 300 meters on foot from the historic center of Radda. It offers the perfect blend of countryside quietness and village convenience, featuring a large private garden with breathtaking panoramic views over vineyards and a beautiful glass-enclosed loggia. The perfect oasis to relax and enjoy the sunset after exploring Siena, Florence, and nearby wineries.

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
4.85 out of 5 average rating, 179 reviews

Villa La Doccia, Greve in Chianti

Villa La Doccia is located about an 8-minute drive from the centre 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 while still being close to the centre of Greve in Chianti.

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
4.98 out of 5 average rating, 104 reviews

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.

Top guest favourite
A spacious outdoor area features a swimming pool surrounded by lush green lawns and dotted with comfortable sun loungers. Umbrellas provide shade, and the serene landscape is framed by tall trees and gentle hills in the background.
Farm stay in Greve in Chianti
4.99 out of 5 average rating, 429 reviews

Typical Tuscan country house

Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, dominates the Chianti valleys and enjoys a splendid view of the surrounding hills and the city of Florence just 35 minutes by car This apartment is one level, totally independent with private garden. Restored and furnished with great care to make the guest's stay as comfortable and relaxing as possible, in the full respect of the Tuscan rural style.

Guest favourite
Dome in Volterra
4.95 out of 5 average rating, 159 reviews

Green Dome @ The Land Before Time Retreats

Nestled among Tuscan olive groves between Volterra and San Gimignano, The Land Before Time – Quad & Saddle Retreats offers 4 Green Domes with private jacuzzi, en-suite bathroom, air conditioning and Wi-Fi. Enjoy breakfast each morning in the Cupola Lounge with stunning views. During your stay, experience horseback rides through scenic trails, quad tours to discover hidden Tuscany, or simply relax under the starry sky.

Superhost
A stone bungalow is viewed from the poolside, featuring a private pool surrounded by sun loungers and an umbrella. The terrace, equipped with a dining table and chairs, shows lush greenery and elegant flowers in window boxes.
Villa in Radda in Chianti
5.0 out of 5 average rating, 10 reviews

La Casa di Radda

La Casa di Radda is a welcoming holiday home in the Chianti Classico region, notable for its proximity to the charming village of Radda. Just a short walk separates the house from the delightful restaurants, cafés, and small shops in the town center. It is ideal for a family vacation or a getaway with friends, offering the perfect setting for relaxing days in a rural environment.

Popular amenities for Villa vacation rentals

Frequently Asked Questions

  • What are the best places to stay in Villa?

    Stay in central town apartments for easy access to cafes and shops, or choose countryside villas and farmhouses for a peaceful retreat amid nature. Many accommodations blend traditional style with modern comforts.

  • What are the best things to do in Villa with kids?

    Families can explore outdoor parks, join farm visits, or participate in simple cooking classes designed for younger guests. Many find joy in gelato stops, open-air picnics, and gentle countryside strolls.

  • What are some of the best things to do in Villa?

    Explore local wineries, join culinary workshops, or wander through historic town centers with narrow streets and artisan shops. Seasonal festivals and market days provide a glimpse into Villa’s traditions.

  • How is the weather in Villa?

    Villa experiences mild winters with temperatures around 33–49°F (0–9°C), and warm, dry summers reaching 89°F (31°C). Spring and autumn bring comfortable temperatures and a mix of sunshine and refreshing rain, making them appealing for outdoor activities.

  • When is the best time to visit Villa?

    Spring and early autumn in Villa are often recommended for comfortable temperatures and vibrant landscapes. Summer draws visitors for outdoor events, while winter has a quieter pace and festive village atmospheres.

  • What are the best places to visit in Villa?

    Explore Villa’s historic piazzas, step into small museums, or relax in peaceful public gardens. Nearby churches and artisan studios also capture the local character.

  • What are some hiking trails in Villa?

    Villa has scenic hiking options through rolling hills, vineyards, and woodland paths. Explore routes that pass olive groves and quiet villages, or venture onto parts of the surrounding countryside’s networks for panoramic views and gentle terrain.

  • What are some family activities we can do in Villa?

    Enjoy outdoor picnics, visit small farms for animal encounters, or join hands-on cooking workshops geared toward families. Wandering local markets and exploring historical squares also provide activities for all ages.

  • What are some of the best day trip ideas from Villa?

    From Villa, travelers often explore medieval towns, historic estates, and hillside vineyards. Art cities, thermal baths, and regional markets around Tuscany provide a rich mix of nature, history, and culinary discovery.

  • Are there any pet friendly accommodations available in Villa?

    Villa has accommodations where pets are welcome, including countryside stays and some central apartments. Many hosts provide details about garden access or nearby walking paths, which can make travel with pets more comfortable.

  • What are some local tips for visiting Villa?

    Locals suggest visiting traditional markets for regional produce and handcrafted goods. Wearing comfortable shoes helps on cobblestone streets, and learning a few Italian phrases is appreciated by residents.

  • What is Villa known for?

    Villa is known for its Tuscan landscapes, locally rooted cuisine, and cultural heritage. The area has vineyards, Renaissance-era architecture, and traditional festivals that highlight community traditions.

  • What are the best hidden gems to explore in Villa?

    Seek out family-run wineries, lesser-known chapels, and tranquil gardens tucked away in quiet corners of Villa. Local artisan workshops and hillside picnic spots reveal a quieter side of the area.

  • What are the best foods to try in Villa?

    Villa’s cuisine is rooted in Tuscan flavors—try dishes like ribollita soup, handmade pici pasta, and locally produced cheeses. Olive oil, truffle specialties, and traditional desserts such as cantucci with vin santo are frequently suggested.

  • What should I bring for a trip to Villa?

    Pack comfortable walking shoes, layers for changing weather, and a hat for sun protection in summer. A reusable water bottle and a camera help capture and enjoy the experience.

  • What is the nightlife in Villa like?

    Villa’s nightlife centers around local wine bars, relaxed trattorias, and occasional live music in town squares. In summer, open-air gatherings and cultural performances become part of the evening scene.

  • What are the most popular events or festivals in Villa?

    Villa frequently hosts traditional food festivals, grape harvest celebrations in early autumn, and local fairs featuring arts and crafts. Guests also gather for music performances and community events during the summer months.

  • Are there family friendly vacation rentals in Villa?

    Villa has family-friendly rentals, including countryside villas, farmhouses, and spacious apartments. Some properties feature gardens or pools and amenities suited for guests of all ages.