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Vacation rentals in Villa

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Top-rated vacation rentals in Villa

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

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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, 190 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, 110 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
Home in Asciano
4.96 out of 5 average rating, 137 reviews

Palazzo Monaci - Pool in the Crete Senesi

Welcome to Palazzo Monaci! An oasis of nature and unique beauty, in the heart of the Crete Senesi, in Tuscany. A residence with a pool and a breathtaking view of the Crete Senesi. Perfect for couples or families looking for a relaxing vacation. The location is perfect for exploring the surrounding areas. You can hike in the Tuscan countryside, visit the characteristic medieval villages, taste the delicious local wines, and immerse yourself in the culture and history of this fascinating region.

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, 154 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 charming cottage is shown with a terracotta facade and a tiled roof. A small table with two chairs is set on a patio, surrounded by potted plants. Lush greenery and trees can be seen in the background under a clear blue sky.
Guesthouse in Macciano
4.97 out of 5 average rating, 242 reviews

Tuscan cottage with an heavenly view

Heaven's Window takes your breath away. As our only guests, you will be surrounded by infinite views, endless tranquility, sounds of singing birds and calling deer. Down the valley and on your walks you may spot foxes ferrets and wild boar. Collect porcupine quills. Breathe! Halfway between Rome and Florence. Close to Siena, Val d’Orcia and countless hot springs . A private paradise surrounded by divine dining and hilltop jewels of antiquity like Montepulciano and Montalcino of sublime wines.

Top guest favourite
An aerial view captures Podere Vergianoni nestled in the Chianti hills, surrounded by lush vineyards. The property features a clear blue pool, shaded terraces, and carefully landscaped gardens. Rolling hills and rows of grapevines create a serene backdrop, highlighting the natural beauty of the Tuscan countryside.
Condo in Noce
5.0 out of 5 average rating, 345 reviews

Podere Vergianoni nestled in Chianti with a pool

Podere Vergianoni is a historic, family-run property dating back to the 1600s, located in the beautiful hills of Chianti in Tuscany. Our family can arrange a private shuttle and local experiences directly. The apartment is available for 2 adults with the possibility of adding a sofa bed for 2 children under 12 years of age. In the large outdoor courtyard you'll find a saltwater pool with a relaxation area on a panoramic terrace overlooking the castle and vineyards with unique sunsets.

Top guest favourite
A stone structure with a tiled roof is framed by greenery, surrounded by rolling hills. A spacious outdoor area features a wooden table, inviting relaxation. Large trees and thriving shrubs enhance the tranquil setting, with a backdrop of a serene sunset illuminating the landscape.
Home in San Casciano In Val di Pesa
4.98 out of 5 average rating, 240 reviews

The Chianti Classico Sunset

If you are looking for an idyllic location in the heart of the Chianti Classico region, surrounded by the vineyards and olive groves of the beautiful Tuscan hills, on the estate of a historic 16th-century villa, then come to our barn!! It has a dominant position with an amazing view, where you can enjoy breathtaking sunsets. The house's complete independence, the welcoming garden and the large loggia allow you to enjoy a stay in total tranquility. Our reviews are your best guarantee.

Top guest favourite
The exterior of the castle is showcased at sunset, with vibrant orange and purple skies providing a dramatic backdrop. Stone towers rise from the landscape, surrounded by greenery and colorful flora, reflecting the historic charm of the property.
Castle in Ferrano
4.99 out of 5 average rating, 224 reviews

The Castle of Ferrano - Castle in Tuscany

Try the experience of staying in a real Castle! Il Castello di Ferrano offers to its hosts the chance of living an unforgettable experience: you will be the only guests in the castle, and everything will be for you (private pool from June to September, gardens etc..). Historical building, surrounded by nature, finely decorated, frescoes/moulding on the ceiling, ample terrace w/ stone and terracotta floor, private outdoor pool.. Good position. Preferably come by car.

Guest favourite
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, 178 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 charming stone building surrounded by lush greenery features a wooden terrace with a parasol and flower pots. Two loungers are placed on the well-maintained lawn, providing a relaxing outdoor space.
Farm stay in Greve in Chianti
4.99 out of 5 average rating, 476 reviews

Old hayloft on the Chianti hills

Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, overlooking the Chianti valleys and enjoying splendid views of the surrounding hills and the city of Florence. The apartment is completely independent, on two internally connected floors, and features a private garden lined with centuries-old oaks and Tuscan cypresses. The restoration maintained the original Tuscan architectural style of rural barns.

Guest favourite
Dome in Volterra
4.96 out of 5 average rating, 157 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.

Top guest favourite
A spacious living area features a modern design, with a prominent stone fireplace and minimalist furniture. Large glass doors open to a serene outdoor view, while natural light brightens the room, highlighting the soft tones of the walls and furnishings.
Tower in Fiesole
4.95 out of 5 average rating, 219 reviews

A Big Dream in a Little Tower.

The Tower was created in the late 1800s by an illustrious Englishman, Sir John Temple Leader, in one of the oldest and most important stone quarries belonging to the Medici family. From the same quarry were extracted many important works such as the columns of the Medici chapels, the steps of the Laurenziana library .. all just 5 km from the historic center of Florence.

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.