Villas and Holiday homes in Tuscany

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Tuscany villas
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40269 Villa rentals in Tuscany

Best Tuscany villas and holiday homes with a pool

Among the 40269 accommodations in Tuscany, here are the 4 best villas and holiday homes with a pool

Agriturismo Fattoria Di Sommaia - Tuscany
9.0 128 reviews
Tuscany
30/07 – 13/08
SG$230/nighttotal: SG$3220 (14 )

Agriturismo Fattoria Di Sommaia

2 4
farm , Calenzano
Agriturismo Fattoria di Sommaia is located on the outskirts of Calenzano, just 1 kilometre from the town centre and a 40-minute drive from Florence. The farm offers a peaceful retreat from the bustling city, with a very good user, location and cleanliness rating.
The accommodation features comfortable apartments with a seating area, TV, well-equipped kitchenette and private bathroom. Guests can enjoy a refreshing swim in the outdoor pool, play tennis on the court, or relax in the garden with barbecue facilities.
50 M² Farmhouse ∙ 1 Bedroom ∙ 4 Guests - Tuscany
8.8 22 reviews
Tuscany
03/08 – 10/08
SG$154/nighttotal: SG$1078 (7 )

50 M² Farmhouse ∙ 1 Bedroom ∙ 4 Guests

1 2
farm , Castelfranco Piandiscò
Farm for up to 4 guests with an excellent rating of 88% based on 22 reviews. Your accommodation will be located in Castelfranco Piandiscò.
Services and facilities: a restaurant, free parking and a fridge. Take advantage of the pool in this accommodation.
Beautiful Historic 7-bedroom Villa On Organic Olive Farm, Pool & Sunset Views - Tuscany
9.4 20 reviews
Tuscany
09/08 – 19/08
SG$1224/nighttotal: SG$12240 (10 )

Beautiful Historic 7-bedroom Villa On Organic Olive Farm, Pool & Sunset Views

7 12
house , Barberino Tavarnelle
This 15-bedroom house in Barberino Tavarnelle, Tuscany, is situated 5km from the Isole e Olena Winery and Chianti Observatory, and within 10km of Montecalvario and Castellina in Chianti's fortress.
The property boasts a private pool, extensive gardens, a tennis court, and a spa, alongside a fully equipped kitchen, free Wi-Fi, and an arcade/game room, perfect for large families or groups.
Monastero San Silvestro - Tuscany
9.1 668 reviews
Tuscany
17/07 – 18/07
SG$261/nightfor 1 night

Monastero San Silvestro

1 3
farm , Cortona
Monastero San Silvestro is a farm located near Cortona in the Valdichiana Valley, just 15 kilometres from Lake Trasimeno and a short drive from Mount Amiata. This property has received excellent ratings for location, cleanliness, and overall user experience.
The farm offers spacious apartments decorated in a traditional Tuscan style. Guests can enjoy the outdoor swimming pool with views of Cortona and the Valdichiana Valley, as well as BBQ facilities, a garden, and free parking.

Top cities

Best family friendly Tuscany villas and holiday home

Among the 40269 accommodations in Tuscany, here are the 4 best family friendly villas and holiday homes

80 M² House ∙ 2 Bedrooms ∙ 4 Guests - Tuscany
8.8 2 reviews
Tuscany
28/06 – 10/07
SG$149/nighttotal: SG$1788 (12 )

80 M² House ∙ 2 Bedrooms ∙ 4 Guests

2 2
house , Gaiole in Chianti
L'arco della Fonte is situated in Gaiole in Chianti, offering easy access to local public transport and is within a convenient driving distance of Chianti's renowned vineyards and villages.
This 80 square metre house sleeps four guests in two bedrooms and one bathroom, and boasts a garden, terrace, barbecue, high-speed Wi-Fi, gym equipment, and even provides access to homegrown produce and locally produced wine.
Villa Il Circolo By Interhome - Tuscany
9.6 38 reviews
Tuscany
22/08 – 29/08
SG$273/nighttotal: SG$1911 (7 )

Villa Il Circolo By Interhome

3 5
house , Rufina
Villa Il Circolo, located in Borselli near Rufina, is a short drive from The Mall Luxury Outlet and approximately 27 kilometres from Florence's Ponte Vecchio and Piazza della Signoria.
This 150-square-metre property offers three bedrooms, two bathrooms, a private pool, free Wi-Fi, a fully equipped kitchen with dishwasher, and a relaxing garden; a baby cot is available, and extra beds can be added.
Casa Bartali - Tuscany
9.2 15 reviews
Tuscany
18/07 – 31/07
SG$182/nighttotal: SG$2366 (13 )

Casa Bartali

2 4
house , Chiusdino
Casa Bartali, a 13th-century house in Chiusdino, Tuscany, is situated approximately 35-38km from Siena and its attractions, including Piazza del Campo and the Pinacoteca Nazionale.
This 120 square metre property sleeps up to 10 guests, boasting two bedrooms, two living rooms, a fully equipped kitchen with fridge, toaster and coffee machine, a bathroom with walk-in shower, and on-site bicycle parking for exploring the Tuscan countryside.
Agriturismo Le Case Di San Vivaldo - Tuscany
9.3 206 reviews
Tuscany
29/08 – 09/09
SG$194/nighttotal: SG$2134 (11 )

Agriturismo Le Case Di San Vivaldo

2 4
farm , Montaione
Agriturismo Le Case di San Vivaldo is a farmhouse situated 10km from Montaione and 18km from San Gimignano, offering a peaceful escape in the Tuscan countryside. This property consistently receives excellent ratings for its location, cleanliness, and overall experience.
The farmhouse features a fully equipped kitchen with a dishwasher and refrigerator, allowing guests to prepare their own meals. Enjoy the beautiful surroundings with a refreshing dip in the seasonal outdoor pool, relax on the terrace, or take advantage of the bar, tennis court, and garden.

Frequently asked questions about villa rentals in Tuscany

  • What are the must-see attractions in Tuscany, Italy?

    Tuscany boasts countless highlights! For art and history, Florence is a must, with the Uffizi Gallery, the Duomo, and Ponte Vecchio being essential stops. Siena's Piazza del Campo is breathtaking, and the medieval hilltop towns of San Gimignano and Volterra offer stunning views and fascinating architecture. Don't forget the leaning tower of Pisa either!
  • What are the best villa rentals in Tuscany?

    Among the villa rentals in Tuscany, Graziosa Casa Indipendente, B&b Country House Poggio Del Drago and Villa Fracassini are the most popular ones.

  • Is Tuscany, Italy known for mountains, beaches, forests, or other types of landscapes?

    Tuscany's landscape is incredibly diverse. Rolling hills covered in vineyards and olive groves are iconic, but there are also mountain ranges like the Apennines, offering hiking opportunities. The coastline, particularly in the south around the Maremma region, provides beautiful beaches. Extensive forests, particularly chestnut forests, are also a significant feature of the region's scenery.
  • What are the best villa rentals with a pool in Tuscany?

    B&b Country House Poggio Del Drago, Villa Fracassini and Podere Vignola are the best villa rentals with a pool in Tuscany.

  • What are the most surprising and hidden attractions in Tuscany, Italy?

    Many lesser-known gems await discovery. The thermal baths of Saturnia offer a unique and relaxing experience. The Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna provides stunning natural beauty and hiking trails. The charming medieval town of Pitigliano, carved into the tufa rock, is another hidden delight.
  • What are the best villa rentals with a jacuzzi in Tuscany?

    The best villa rentals with a jacuzzi in Tuscany are Villa Fracassini, Bosco Della Spina and Il Casale Di Santamettole.

  • What are some unique ways to learn about the culture of Tuscany, Italy by engaging with its people?

    Take a cooking class and learn to make pasta from scratch using local ingredients. Attend a wine tasting at a family-run vineyard, engaging with the winemakers directly. Visit a local artisan workshop, perhaps a leather workshop in Florence or a ceramics studio in Montelupo Fiorentino, and interact with the craftspeople.
  • What are the best villa rentals for families and kids in Tuscany?

    The best villa rentals for families and kids in Tuscany are Graziosa Casa Indipendente, B&b Country House Poggio Del Drago and Villa Fracassini.

  • How much time should you set aside to thoroughly explore Tuscany, Italy?

    A week allows for a good overview of Tuscany’s highlights, focusing on a particular region. To truly explore the region’s diverse landscapes and towns, at least two weeks are recommended. A month would allow for a more relaxed pace and the opportunity to discover hidden gems.
  • What are the best pet friendly villa rentals in Tuscany?

    The best pet friendly villa rentals in Tuscany are B&b Country House Poggio Del Drago, Villa Fracassini and Podere Vignola.

  • Is there anything you might not think to pack for Tuscany, Italy?

    Comfortable walking shoes are essential, as much of Tuscany is best explored on foot. A reusable water bottle is also highly recommended, especially during the warmer months. Insect repellent can be useful, particularly during the summer evenings. A hat and sunscreen are also advisable.
  • What are the best villa rentals with parking in Tuscany?

    Graziosa Casa Indipendente, B&b Country House Poggio Del Drago and Villa Fracassini are the best villa rentals with parking in Tuscany.

  • What cultural experiences or workshops in Tuscany, Italy offer something different?

    Consider a truffle hunting experience with a local expert and his dog. Learn the art of fresco painting, a traditional Tuscan craft. Participate in a wine blending workshop at a renowned vineyard. These offer unique insights into Tuscan culture.
  • Are there any food festivals in Tuscany, Italy where you can try local food?

    The Giostra del Saracino in Arezzo is a historical event with associated food stalls. Many towns and villages host smaller, local food festivals throughout the year, celebrating seasonal produce. Check local listings for specific dates and events.
  • What seasonal natural events, such as migrations or blooming periods, occur in Tuscany, Italy?

    Spring brings the blooming of wildflowers, particularly in the rolling hills. Autumn sees the changing colours of the leaves in the forests of the Apennines. Bird migration is a year-round occurrence but is most noticeable in spring and autumn.
  • What exclusive experiences are available when visiting Tuscany, Italy?

    A hot air balloon ride over the Tuscan countryside offers breathtaking views. A private wine tasting at a prestigious vineyard provides a luxurious experience. A stay in a historic villa or agriturismo offers unique accommodation and a chance to experience authentic Tuscan life.

Nearby regions

Best Tuscany villas and holiday homes with a kitchen

Appartamento Fioreale - Sulle Colline Toscane A 11 Km Dal Mare - Tuscany
9.0 22 reviews
Tuscany
18/07 – 26/07
SG$233/nighttotal: SG$1864 (8 )

Appartamento Fioreale - Sulle Colline Toscane A 11 Km Dal Mare

3 6
house , Montescudaio
This two-bedroom house in Montescudaio, a Tuscan town just 10 kilometres from the coast and 13 kilometres from Acqua Village, offers a peaceful retreat for families and groups.
The 85 square metre property features a terrace, garden, and a fully equipped kitchen with a dishwasher and microwave, perfect for enjoying a self-catering holiday.
Casa Giulia - Tuscany
8.9 74 reviews
Tuscany
20/06 – 27/06
SG$137/nighttotal: SG$959 (7 )

Casa Giulia

1 2
farm , Reggello
Casa Giulia, a Reggello farmhouse stay in Tuscany, is conveniently located 14.5km from The Mall Luxury Outlet and 30.5km from Piazza Matteotti, with Florence Airport 51.5km away.
This self-catering property offers a private pool, tennis court, BBQ facilities, free Wi-Fi, and parking, alongside nearby cycling and fishing opportunities.
The Fruit House - Tuscany
10 2 reviews
Tuscany
15/08 – 19/08
SG$211/nighttotal: SG$844 (4 )

The Fruit House

2 4
house , Cascina
This detached house, named The Fruit House, is located in Cascina, 5 kilometres from Pisa's main attractions, with Pisa International Airport 5 kilometres away and the Botanical Gardens of Pisa 6.8 kilometres distant.
This 85 square metre property offers accommodation for up to 7 guests in 2 bedrooms, featuring air conditioning, a fully equipped kitchen, complimentary Wi-Fi and private parking, with a jacuzzi for added comfort.
Peccioli Family Retreat W Fun - Tuscany
9.2 67 reviews
Tuscany
01/08 – 15/08
SG$268/nighttotal: SG$3752 (14 )

Peccioli Family Retreat W Fun

1 4
apartment , Peccioli
Belvilla by OYO Calendula Primo Piano, a self-catering apartment in Peccioli, Tuscany, is situated approximately 50 kilometres from Pisa and its Piazza dei Miracoli.
This two-bedroom property boasts a private terrace, swimming pool, fitness centre, tennis court, and free Wi-Fi, offering guests access to a barbecue, table tennis, and a children's playground.

Neighborhoods and points of interest in Tuscany

Best Tuscany villas and holiday homes with jacuzzi

400 M² House ∙ 4 Bedrooms ∙ 12 Guests - Tuscany
9.0 6 reviews
Tuscany
20/06 – 22/06
SG$890/nighttotal: SG$1780 (2 )

400 M² House ∙ 4 Bedrooms ∙ 12 Guests

4 12
house , Piazza al Serchio
This spacious Tuscan villa near Piazza al Serchio offers easy access to hiking trails and golf courses, with the beach an unspecified distance away.
The 400 square metre property boasts four bedrooms, six bathrooms, and a private swimming pool, accommodating up to twelve guests and including a fitness centre, multiple living areas, and a large terrace.
Old Restored Lemon House Near The Center - Tuscany
10 5 reviews
Tuscany
02/08 – 09/08
SG$855/nighttotal: SG$5985 (7 )

Old Restored Lemon House Near The Center

4 7
house , Lucca
This family-friendly villa is situated in a rural area near Lucca, less than 2km from the Walls of Lucca, Via Fillungo, and the Museum of Torture.
This 300 square metre property boasts four bedrooms, four bathrooms, sleeps eight guests, and features a fully equipped kitchen, private garden, jacuzzi, and free Wi-Fi.
Comfortable House With Pool In Castelnuovo Di Garfagnana - Tuscany
9.7 115 reviews
Tuscany
01/11 – 04/11
SG$229/nighttotal: SG$687 (3 )

Comfortable House With Pool In Castelnuovo Di Garfagnana

3 2
house , Castelnuovo di Garfagnana
Il Nido, a private villa in Castelnuovo di Garfagnana, is situated 47km from Val di Luce and 40km from the Royal Villa of Marlia.
This three-bedroom property boasts a swimming pool, jacuzzi, and tennis court, alongside a fully equipped kitchen and fireplace, perfect for families or groups seeking a self-catering holiday with access to on-site amenities and nearby skiing and fishing.
Amore Rentals - Villa Ambretta - Tuscany
10 3 reviews
Tuscany
20/06 – 27/06
SG$806/nighttotal: SG$5642 (7 )

Amore Rentals - Villa Ambretta

3 3
house , Campagnatico
Villa Ambretta, in Campagnatico, is situated approximately 32 kilometres from the Maremma Regional Park, offering easy access to stunning natural landscapes.
This 160-square-metre property boasts three bedrooms, four bathrooms, a private pool, fitness centre, sauna, and ample outdoor space including a terrace and garden, perfect for families or groups of up to six guests.
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