Holiday Rentals in Tuscany

142342 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • hotelscom
  • vrbo
  • tripadvisor
  • expedia
  • tripcom
  • agoda
  • homestay
  • tuivillas
  • hostelworld
  • hotelopia
Tuscany holiday rentals
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

Best Holiday rentals and Airbnb offers in Tuscany

Best family friendly Tuscany holiday rentals

Among the 142342 accommodations in Tuscany, here are the 4 best family friendly rentals

Cortona Shabby Chic House - Tuscany
9.9 474 reviews
Tuscany
26/06 – 28/06
SG$148/nighttotal: SG$296 (2 )

Cortona Shabby Chic House

1 2
apartment , Cortona
This charming apartment is located in Cortona's historic Old Town, just 30 kilometres from Piazza Grande and 37 kilometres from Montepulciano Terme. It enjoys an excellent user rating, location rating and cleanliness rating.
The apartment is a one-bedroom, one-bathroom property with a floor area of 50 square metres, comfortably accommodating up to three guests. It features a fully equipped kitchen, air conditioning, a balcony with city views, and a private garden, perfect for relaxing and enjoying the Tuscan sunshine.
Appartamento Porta Pispini - Tuscany
9.6 810 reviews
Tuscany
09/07 – 12/07
SG$206/nighttotal: SG$618 (3 )

Appartamento Porta Pispini

2 4
apartment , Siena
Appartamento Porta Pispini is conveniently located in Siena, just a 10-minute walk from Piazza del Campo and within easy reach of the city's main attractions. The apartment has consistently received excellent ratings for location, cleanliness, and overall experience.
This two-bedroom flat offers comfortable accommodation for up to four guests in a spacious 50 square metres. Enjoy modern amenities like air conditioning, free Wi-Fi, a fully equipped kitchen, and a washing machine, perfect for a relaxing stay in the heart of Siena.
Il Mercato - Appartamento Con Vista - Tuscany
9.4 137 reviews
Tuscany
10/07 – 12/07
SG$132/nighttotal: SG$264 (2 )

Il Mercato - Appartamento Con Vista

1 1
apartment , Sinalunga
Book this vacation rental with an excellent rating of 94% based on 137 reviews. You will stay in Sinalunga.
Services and facilities: an iron, free parking and a kitchen. This apartment also has air conditioning!
La Chiocciola - Tuscany
9.5 22 reviews
Tuscany
22/08 – 05/09
SG$181/nighttotal: SG$2534 (14 )

La Chiocciola

1 2
house , Gaiole in Chianti
Raffaello, a holiday home in Gaiole in Chianti, enjoys a peaceful countryside setting, approximately 32km from Siena's Piazza del Campo and 42km from Arezzo's Piazza Matteotti.
This self-catering property offers two bedrooms, a dining area, a fully equipped kitchen including dishwasher, a private entrance, swimming pool, tennis court, and free Wi-Fi, sleeping up to a small family group.

Top cities

Best pet friendly Tuscany holiday rentals

Among the 142342 accommodations in Tuscany, here are the 4 best pet friendly rentals

Agriturismo Fattoria Pagnana Wine & Pool - Tuscany
9.1 103 reviews
Tuscany
27/06 – 04/07
SG$142/nighttotal: SG$994 (7 )

Agriturismo Fattoria Pagnana Wine & Pool

1 2
farm , Rignano sull'Arno
Fattoria Pagnana Suites & Pool is situated in Rignano sull'Arno, Tuscany, 5.6km from The Mall Luxury Outlet and 21km from the Ponte Vecchio in Florence.
This self-catering property offers a swimming pool, tennis court, and garden with stunning views, alongside family-friendly amenities including outdoor play equipment and accessible facilities.
Cozy Welcoming Apartment For A Lovely Stay - Tuscany
9.0 34 reviews
Tuscany
06/08 – 09/08
SG$152/nighttotal: SG$456 (3 )

Cozy Welcoming Apartment For A Lovely Stay

1 3
chalet , Castelfranco Piandiscò
This charming chalet, Fattoria Il Praticino - Metato, is situated in Castelfranco Piandiscò, just 21 miles from Arezzo's Piazza Matteotti and 27 miles from Florence's Piazzale Michelangelo, offering a peaceful retreat in the Tuscan countryside. The property enjoys very good user, location and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The chalet features a bedroom, two bathrooms and a fully equipped kitchenette with a fridge and microwave oven. Guests can enjoy a private garden, a terrace or balcony, a swimming pool, a restaurant and bar, a fitness centre, parking and a peaceful setting with stunning views of the surrounding mountains and a nearby lake.
Villa Del Parco In Tuscany - Tuscany
8.7 193 reviews
Tuscany
17/08 – 23/08
SG$335/nighttotal: SG$2010 (6 )

Villa Del Parco In Tuscany

1 3
resort , Lamporecchio
Villa Del Parco Resort is situated in San Baronto, 21 kilometres from Montecatini Train Station, in the heart of the Tuscan countryside, close to Lamporecchio, a town known for its history and beautiful landscapes. The resort has received very good ratings for location and user experience and excellent ratings for cleanliness.
The villa offers 10 bedrooms, 5 living rooms, and 10 bathrooms, providing ample space for large families or groups of friends. Guests can enjoy a range of amenities including a swimming pool, spa, restaurant, bar, fitness centre, tennis court, and a garden.
Mea Casa Toscana - Tuscany
9.6 180 reviews
Tuscany
28/08 – 04/09
SG$312/nighttotal: SG$2184 (7 )

Mea Casa Toscana

1 6
apartment , Castellina in Chianti
MEA CASA Toscana is a self-catering apartment in Castellina in Chianti, situated 13km from Piazza Matteotti and 27km from Piazza del Campo in Siena.
This family-friendly property boasts a private garden, swimming pool with Tuscan countryside views, barbecue facilities, outdoor fireplace, and free Wi-Fi and parking; airport transfers are available at an extra cost.

Frequently asked questions about holiday rentals in Tuscany

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

    Tuscany boasts countless iconic sights. Florence, naturally, is a must, with the Duomo, Uffizi Gallery, and Ponte Vecchio topping the list. Siena's Piazza del Campo is breathtaking, and the leaning tower of Pisa is undeniably a classic photo opportunity. San Gimignano, with its medieval towers, offers a charming glimpse into the past. Don't forget the rolling hills of the Chianti region, perfect for wine tasting.
  • What are the best Airbnb and vacation rentals in Tuscany?

    Appartamento Del Campo, Podere Vignola and Poggio Massiccioli are the most popular Airbnb and vacation rentals in Tuscany among travelers.

  • Are there unique natural phenomena in Tuscany, Italy?

    While Tuscany isn't known for dramatic geological events, its landscape itself is a unique phenomenon. The rolling hills of Tuscany, sculpted over centuries, are a stunning example of natural beauty. The thermal baths of Saturnia and Bagno Vignoni offer a chance to experience the region's geothermal activity. The coastal areas, like the Argentario promontory, provide diverse ecosystems and stunning sea views.
  • What are the most popular Airbnbs in Tuscany?

    Among the Airbnbs in Tuscany, La Casa Di Enne, Apartment Of 35 Sq In Villa With Pool and Verde - I Prati In Toscana are the most popular ones.

  • What essentials should you bring along for a trip to Tuscany, Italy?

    Comfortable walking shoes are crucial, as you'll be doing a lot of exploring on foot. Pack light, breathable clothing suitable for both warm days and cooler evenings. Don't forget sunscreen, a hat, and sunglasses, especially during the summer months. A reusable water bottle is essential, as well as a phrasebook or translation app for easier communication.
  • What are the best vacation rentals with a pool in Tuscany?

    Podere Vignola, Poggio Massiccioli and Ripostena are the best vacation rentals with a pool in Tuscany.

  • What famous events or festivals are happening in Tuscany, Italy?

    The Palio di Siena, a thrilling horse race held twice a year in Piazza del Campo, is world-famous. Many smaller towns and villages hold their own festivals throughout the year, often celebrating local saints or harvests. The Maggio Musicale Fiorentino, a classical music festival held in Florence in the spring, is another significant event.
  • What are the best rentals for families and kids in Tuscany?

    The best rentals for families and kids in Tuscany are Appartamento Del Campo, Podere Vignola and Poggio Massiccioli.

  • What is the average daily budget you should plan for (accommodation, food, transportation, activities) in Tuscany, Italy?

    A daily budget will vary greatly depending on your travel style. For budget travellers, €80-€120 per day might suffice, covering basic accommodation, affordable meals, and local transport. Mid-range travellers should plan for €150-€250 per day, and luxury travellers could easily spend upwards of €300 per day or more.
  • What are the best rentals or Airbnbs with a jacuzzi in Tuscany?

    The best vacation rentals or Airbnb with a jacuzzi in Tuscany are Silencieux Oltrarno, Casa Martellucci and Stone Rustico With Jacuzzi - Infrared Sauna Escluiva.

  • Where can you find the best restaurants serving local dishes in Tuscany, Italy, and what are the must-try specialties?

    Many trattorias throughout Tuscany serve authentic dishes. In Florence, Trattoria Mario is a popular choice. In Siena, Osteria Le Logge is renowned. Must-try dishes include Bistecca alla Fiorentina (Florentine steak), Ribollita (bread soup), and Pappa al Pomodoro (bread and tomato soup). Don't forget the local wines, especially Chianti Classico.
  • What are some less-famous attractions in Tuscany, Italy that are worth a visit?

    The Val d'Orcia, a UNESCO World Heritage site, offers stunning landscapes and charming hilltop towns like Pienza and Montepulciano. The Garfagnana region in the north is less touristy but boasts beautiful mountains and medieval villages. The Etruscan tombs of Populonia offer a fascinating glimpse into ancient history.
  • What are the best activities for engaging with locals and understanding their culture in Tuscany, Italy?

    Take a cooking class and learn to prepare traditional Tuscan dishes. Visit a local winery and participate in a wine tasting, engaging with the winemakers. Attend a local festival or market to experience the vibrant community spirit. Simply striking up conversations with locals in smaller towns and villages can be very rewarding.
  • What unique natural landscapes and terrain features can travellers explore in Tuscany, Italy?

    The rolling hills of the Chianti region, covered in vineyards and olive groves, are iconic. The rugged coastline of the Maremma offers dramatic cliffs and sandy beaches. The mountainous areas of the Garfagnana and Casentino provide opportunities for hiking and exploring forests. The thermal springs around Saturnia showcase the region's geothermal activity.
  • How many days are ideal for a trip to Tuscany, Italy, and what are some itinerary suggestions?

    Seven to ten days is a good amount of time to explore Tuscany at a comfortable pace. A possible itinerary could include three days in Florence, two days exploring Siena and San Gimignano, and two days in the Chianti region, with a final day for a coastal excursion or exploring another area of interest.

Nearby regions

Best Tuscany holiday rentals with a pool

Among the 142342 accommodations in Tuscany, here are the 4 best rentals with a pool

Corte Pasquini - Tuscany
9.5 98 reviews
Tuscany
09/09 – 17/09
SG$371/nighttotal: SG$2968 (8 )

Corte Pasquini

4 7
house , Capannori
This Corte Pasquini property, a four-bedroom house in San Ginese, Capannori, is situated 24km from Pisa's Leaning Tower and Cathedral, and 8.2km from Lucca's Guinigi Tower.
The 140 square metre dwelling boasts a private garden, swimming pool, free parking, and a fully equipped kitchen including a dishwasher, accommodating up to eight guests and offering excellent amenities for a relaxing stay.
Agriturismo San Gregorio - Tuscany
9.0 130 reviews
Tuscany
26/07 – 02/08
SG$218/nighttotal: SG$1526 (7 )

Agriturismo San Gregorio

2 4
farm , San Vincenzo
Agriturismo San Gregorio is located in San Vincenzo, a 10-minute drive from the train station and 26 kilometres from Piombino, offering a peaceful escape in the Tuscan countryside. The property consistently receives excellent ratings for location, cleanliness, and overall user experience.
The farm offers a range of comfortable apartments and rooms, each equipped with a seating area and a flat-screen TV. Guests can enjoy a refreshing dip in the outdoor pool, relax in the garden, or prepare meals in the fully equipped kitchens, complete with dishwashers and microwaves.
Panoramic Terrace & Pool | Tuscan Hills Escape - Tuscany
9.8 47 reviews
Tuscany
10/09 – 13/09
SG$279/nighttotal: SG$837 (3 )

Panoramic Terrace & Pool | Tuscan Hills Escape

1 4
apartment , Capannori
Fiordaliso cottage, situated in the Lucchese hills near Capannori, offers stunning views and is a short drive from the town centre.
This two-bedroom, one-bathroom holiday home sleeps five, features a spacious open-plan living area, private garden with barbecue, shared swimming pool (open 15 May – 15 October), and parking; laundry facilities are available in a separate building.
Torre Di Ponzano - Tuscany
9.9 409 reviews
Tuscany
28/08 – 05/09
SG$209/nighttotal: SG$1672 (8 )

Torre Di Ponzano

2 2
house , Barberino Tavarnelle
Torre di Ponzano, in Barberino Val d'Elsa, offers an 11th-century property with a private pool (open May-October), conveniently located within 32km of Siena and approximately 40km from Florence.
This self-catering villa boasts air-conditioned rooms, free Wi-Fi, private parking, and a range of amenities including a kitchen, terrace, and garden; weekly cleaning is included for suites and villas.

Neighborhoods and points of interest in Tuscany

Best Tuscany holiday rentals with parking

Mobilheim "Toscane1" Mit Pool - Tuscany
Tuscany
16/08 – 17/08
SG$275/nightfor 1 night

Mobilheim "Toscane1" Mit Pool

2 4
apartment , Viareggio
This mobile home is located on a family campsite within a nature reserve, 900 metres from Viareggio's seaside resort and beaches.
This 50 square metre apartment accommodates up to five guests and features two bedrooms, one bathroom, a kitchen with fridge and freezer, air conditioning, a swimming pool, a terrace, and private parking.
100 M² House ∙ 2 Bedrooms ∙ 6 Guests - Tuscany
10 3 reviews
Tuscany
18/07 – 25/07
SG$232/nighttotal: SG$1624 (7 )

100 M² House ∙ 2 Bedrooms ∙ 6 Guests

2 3
house , Pescia
This holiday villa in Pescia is located in the Tuscan countryside, offering access to trim trails, mountain bike routes, and a motocross track within 5 kilometres, with opportunities for local culinary experiences nearby.
This 100 square meter holiday home accommodates up to 6 guests, featuring 2 bedrooms, 2 bathrooms, a fully equipped kitchen with a fridge, microwave, and dishwasher, air conditioning, Wi-Fi, a garden, a fitness centre, and parking, alongside on-site entertainment including billiards and darts.
Appartmento Il Vicolo - Tuscany
9.4 33 reviews
Tuscany
10/08 – 22/08
SG$166/nighttotal: SG$1992 (12 )

Appartmento Il Vicolo

1 4
house , Rapolano Terme
Appartamento Il Vicolo in Rapolano Terme is located 29 kilometres from Siena Train Station, placing you within 32 kilometres of Siena's Palazzo Chigi-Saracini and the National Museum of Etruscan Archaeology.
This 60 square metre holiday home accommodates up to seven guests, featuring one bedroom, two bathrooms, air conditioning, free WiFi, and a kitchen equipped with a fridge, microwave, and dishwasher.
Residenza Storica Il Pozzo - Tuscany
9.4 78 reviews
Tuscany
21/07 – 31/07
SG$140/nighttotal: SG$1400 (10 )

Residenza Storica Il Pozzo

1 2
apartment , San Quirico d'Orcia
Residenza storica il Pozzo is a charming apartment located in San Quirico d'Orcia, within easy reach of the village centre and just a short drive from the thermal baths of Bagno Vignoni and Bagno San Filippo. This property consistently receives excellent ratings for its location, cleanliness, and overall user experience.
The apartment has one bedroom and one bathroom, providing comfortable accommodation for up to two guests in its 35 square metres of space. Guests can enjoy a fully equipped kitchen, a private garden, and free Wi-Fi, along with a welcome package of treats and the option of parking.
©2026 cozycozy.com