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

Relax In The Countryside Near The Sea(olivo) - Tuscany
9.9 42 reviews
Tuscany
10/07 – 12/07
SG$260/nighttotal: SG$520 (2 )

Relax In The Countryside Near The Sea(olivo)

1 3
house , Campo nell'Elba
This charming villa is situated near the sea in Campo nell'Elba, just a short distance from the beach and local amenities such as a supermarket, bar, and pizzeria. The property has received excellent ratings for its location, cleanliness, and overall experience, making it an ideal choice for travellers seeking a relaxing and comfortable stay.
The villa features one bedroom and one bathroom, accommodating up to three guests. Enjoy a range of amenities, including a private garden with a barbecue area, a Jacuzzi, complimentary cycles, and access to walking trails through the surrounding Mediterranean scrub.
Casa Portone Paola - Tuscany
9.6 35 reviews
Tuscany
02/07 – 09/07
SG$188/nighttotal: SG$1316 (7 )

Casa Portone Paola

2 1
house , Castiglione d'Orcia
Casa Portone Paola, located in Campiglia d'Orcia, offers a convenient base for exploring Castiglione d'Orcia, being 5km from Bagni San Filippo and 18km from Bagno Vignoni.
This 65 square metre property sleeps nine guests and boasts a private pool, solarium, fireplace, outdoor dining area, and parking; nearby attractions include Mount Amiata for hiking and a local mini-market.
Gorgeous Home In Cavriglia Ar - Tuscany
Tuscany
05/08 – 11/08
SG$408/nighttotal: SG$2448 (6 )

Gorgeous Home In Cavriglia Ar

2 5
house , Cavriglia
This detached villa in Cavriglia is located 27 kilometres from The Mall Luxury Outlet and 47 kilometres from Piazza della Signoria.
This 100 square metre property accommodates up to 11 guests with 2 bedrooms, 1 bathroom, a fully equipped kitchen, air conditioning, a private swimming pool, and free high-speed WiFi.
Apartment Ciliegio By Interhome - Tuscany
9.5 167 reviews
Tuscany
05/10 – 09/10
SG$150/nighttotal: SG$600 (4 )

Apartment Ciliegio By Interhome

2 2
apartment , Poggibonsi
This apartment is located in the peaceful village of Monsanto, just 21 miles from Piazza Matteotti and 22 miles from Piazza del Campo in Siena, allowing you to easily explore the Tuscan countryside and the city's historic centre. It has received excellent ratings for location, cleanliness and overall experience, making it a great choice for travellers.
The property is spacious, with 4 bedrooms and 3 bathrooms, ideal for families or groups of friends. You can enjoy the Tuscan sunshine on the balcony, relax in the garden, or take a dip in the swimming pool, while the fully equipped kitchen and free Wi-Fi ensure a comfortable and convenient stay.

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

Agriturismo L'incrociata - Tuscany
9.6 148 reviews
Tuscany
10/08 – 23/08
SG$329/nighttotal: SG$4277 (13 )

Agriturismo L'incrociata

1 4
farm , Bucine
Agriturismo L'Incrociata is a family-friendly farmhouse located in Bucine, Tuscany, approximately 30 kilometres from Siena's Piazza del Campo and 37 kilometres from Arezzo's Piazza Grande.
This rural retreat offers a swimming pool, a shared lounge, barbecue facilities, on-site yoga classes, table tennis, and child-friendly amenities including an indoor play area and outdoor play equipment; all units include fully equipped kitchens and free Wi-Fi.
Villa Baudrocco - Tuscany
9.3 43 reviews
Tuscany
19/08 – 26/08
SG$630/nighttotal: SG$4410 (7 )

Villa Baudrocco

1 9
house , Bagni di Lucca
Villa Baudrocco, in Casabasciana near Lucca, is situated approximately 48km from Lucca and close to Bagni di Lucca's thermal baths.
This four-bedroom, three-bathroom property sleeps nine, boasting a swimming pool, garden, and extensive outdoor spaces including terraces, a barbecue, and access to the owner's garden with fresh produce; nearby activities include rafting, canoeing, and canyoning.
Casa Ila - Tuscany
9.5 32 reviews
Tuscany
01/07 – 31/07
SG$312/nighttotal: SG$9360 (30 )

Casa Ila

2 2
house , Florence
Casa Ila, a family-friendly Florence holiday home, is situated in a tranquil area of Florence, approximately 3.2 to 6.4 km from landmarks such as the Pitti Palace, Strozzi Palace, and Santa Maria Novella.
This 130 square metre property boasts two bedrooms, two bathrooms including a jacuzzi, a terrace, free Wi-Fi, private parking, and can comfortably accommodate up to seven guests.
Le Balze Di Pile Farmhouse - Greve In Chianti - Tuscany
9.9 358 reviews
Tuscany
02/08 – 09/08
SG$170/nighttotal: SG$1190 (7 )

Le Balze Di Pile Farmhouse - Greve In Chianti

1 4
gîte , Greve in Chianti
This Greve in Chianti farmhouse apartment, situated in the Lamole hills, 5km from the medieval town of Greve in Chianti, offers stunning views.
The 60-square-metre property features two bedrooms (one double, one single), two shower rooms, a fully equipped kitchen including a dishwasher, air conditioning, free Wi-Fi, and access to a private garden; sleeping up to three guests.

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

Sunflowers Dimora - Tuscany
9.7 4 reviews
Tuscany
27/06 – 28/06
SG$392/nightfor 1 night

Sunflowers Dimora

2 8
house , Cascina
Sunflowers Dimora, located in Santo Stefano a Macerata, offers convenient access to Pisa Cathedral, Piazza dei Miracoli, and the Leaning Tower of Pisa, all within 16 kilometres, and Livorno Port is 24 kilometres away.
This 150 square metre villa accommodates up to 16 guests across 2 bedrooms, featuring air conditioning, a fully equipped kitchen with a dishwasher, 2 bathrooms, a private garden with barbecue, and a children's playground.
Palace Comfort Inn - Tuscany
8.9 581 reviews
Tuscany
25/07 – 26/07
SG$586/nightfor 1 night

Palace Comfort Inn

4 8
house , Pisa
This charming holiday home is situated just a short walk from the Leaning Tower of Pisa and Piazza dei Miracoli, offering easy access to the city's main attractions. It has received excellent ratings for location, cleanliness, and overall experience.
The property features two bedrooms and a fully equipped kitchen, perfect for families or groups of friends. Guests can enjoy the Italian sunshine on the terrace, relax in the garden, and stay connected with free Wi-Fi.
Villa Amedeo - Tuscany
9.4 151 reviews
Tuscany
08/08 – 14/08
SG$287/nighttotal: SG$1722 (6 )

Villa Amedeo

2 4
house , Sovicille
Villa Amedeo is located in Brenna, a short distance from the River Serse and a 20-minute drive from Siena's centre, offering a peaceful escape into the Tuscan countryside. The property has received very good ratings for its location, user experience and excellent cleanliness.
The villa features exposed wood-beamed ceilings and offers modern amenities such as free Wi-Fi, a satellite TV, a washing machine, a hairdryer, and bathrobes. Guests can enjoy the swimming pool, jacuzzi, terrace, garden, and restaurant on site, as well as explore the surrounding countryside with complimentary bikes.
Villa Le Querciolaie - Tuscany
8.6 584 reviews
Tuscany
14/09 – 21/09
SG$278/nighttotal: SG$1946 (7 )

Villa Le Querciolaie

3 7
house , Monteverdi Marittimo
Villa Le Querciolaie, a 16th-century Florence-style villa, enjoys a peaceful setting in Monteverdi Marittimo, approximately 15km from Castagneto Carducci and a 30-minute drive from the Tyrrhenian Sea.
This self-catering property boasts two swimming pools (one heated year-round), a lush garden with sculptures, in-room breakfast service, free Wi-Fi in communal areas, private parking, and a billiards room.

Neighborhoods and points of interest in Tuscany

Best Tuscany villas and holiday homes with jacuzzi

Villa Nella Toscana Rurale, Vigne & Giardino, Idromassaggio, Barbecue.wi-fi, A/c - Tuscany
Tuscany
18/07 – 23/07
SG$546/nighttotal: SG$2730 (5 )

Villa Nella Toscana Rurale, Vigne & Giardino, Idromassaggio, Barbecue.wi-fi, A/c

3 6
house , Aulla
This villa in Aulla is situated a 3-minute drive from Brunella Fortress and a 2-minute drive from Saint Caprasio Abbey, with Aulla Lunigiana Station accessible within a 12-minute walk.
The property offers 250 square metres of living space, accommodating up to six guests across three bedrooms and three bathrooms, and features a Jacuzzi, garden, air conditioning, WiFi, and onsite parking.
Villa Fè -Choose Panoramic View, Jacuzzi, Private Parking - Tuscany
9.7 67 reviews
Tuscany
17/08 – 24/08
SG$395/nighttotal: SG$2765 (7 )

Villa Fè -Choose Panoramic View, Jacuzzi, Private Parking

3 4
house , Montepulciano
Villa Fè is situated in the Tuscan countryside, just 7.4 kilometres from the charming town of Montepulciano and 4.6 kilometres from the thermal baths of Montepulciano Terme. This property consistently receives excellent ratings for location, cleanliness, and overall user experience.
The villa is a spacious three-bedroom property, covering 90 square metres. Enjoy a range of amenities including a private pool, hot tub, fitness centre, and a fully equipped kitchen, perfect for relaxing and exploring the beautiful Tuscan region.
Agriturismo Corte In Poggio - Tuscany
9.7 379 reviews
Tuscany
02/08 – 09/08
SG$253/nighttotal: SG$1771 (7 )

Agriturismo Corte In Poggio

1 2
farm , Cerreto Guidi
Agriturismo Corte in Poggio, situated in Stabbia near Cerreto Guidi, is approximately 18 kilometres from Montecatini train station and 45 kilometres from Florence's Santa Maria Novella station.
This Tuscan farmhouse offers guests a swimming pool, jacuzzi, tennis court, and free bikes, alongside family-friendly amenities such as outdoor play equipment and a baby safety gate, plus packed lunches for day trips.
157 M² House ∙ 3 Bedrooms ∙ 8 Guests - Tuscany
10 3 reviews
Tuscany
22/08 – 01/09
SG$629/nighttotal: SG$6290 (10 )

157 M² House ∙ 3 Bedrooms ∙ 8 Guests

3 7
house , Massarosa
This Massarosa holiday home offers stunning panoramic sea views and is situated near picturesque hills, providing easy access to hiking trails and Tuscan villages.
This 157 square metre property sleeps eight guests in three bedrooms and two bathrooms, boasting a private pool, jacuzzi, garden, and parking, plus a fully equipped kitchen and air conditioning.
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