Updating...

More filters

Wireless Internet
Air conditioning
Swimming pool
Private pool

Heated pool
Private indoor pool
Washing machine
Garden
Internet access
DVD player
Fireplace
Private tennis court
Cot available
Sauna
Sea view
Safe
Dishwasher
Satellite TV
Children's pool
Video player
Fax machine
Pool or snooker table
Table tennis
Ceiling Fans
Games room
Clothes dryer
Boat available
Cribs
Private outdoor pool (unheated)
Private outdoor pool (heated)
Shared indoor pool
Shared outdoor pool (unheated)
Shared outdoor pool (heated)
Linen provided
Staffed property
Hair dryer
Solarium or roof terrace
TV
Central heating
Stereo system
Kettle
Toaster
Iron
Stove
Private fishing lake or river
Fridge
Freezer
Microwave
Towels provided
Bicycles available
Climbing frame
Swing set or jungle gym
Trampoline
Housekeeping Included

See all

Less

Pets
Pets allowed
Parking
Car not required

Children under 5
Smoking allowed
Non-Smoking property
Smoking - Ask
Elevator access
Wheelchair adapted
Wheelchair accessible
Secure parking

See all

Less

Beach or lakeside relaxation
City breaks
Skiing – property near ski resort
Walking trips

Tennis in town
Nightlife
Water sports
Horse riding
Fishing
Cycling trips
Golf course on site or within 15 min walk
Mountain Views
Beach or lakeside relaxation
Golf within 30mins drive
Lakefront
Waterfront

See all

Less

245 villas

Sort by:

Villa Parmolaia

Ville di Corsano villa

7 bedrooms
7 bathrooms

sleeps 14

Match: Rental types

All filters match

Price per night from

$1,928

Great rentals within 20 miles that match your search

Tower Gates - luxury villa in Chianti!

Gaiole in Chianti villa

7 bedrooms
4 bathrooms

sleeps 14

Match: Rental types

All filters match

Price per night from

$769

Superb villa with pool 30 minutes from Siena and Montalcino

Montalcino villa

6 bedrooms
3 bathrooms

sleeps 7

Match: Rental types

All filters match

Price per night from

$626

Villa with Pool and Jacuzzi private Deal 2024

Siena villa

2 bedrooms
3 bathrooms

sleeps 7

Match: Rental types

All filters match

Price per night from

$123

Private villa with pool in the Montalcino area. 8 persons in 5 bedrooms!

Castelnuovo dell'Abate villa

5 bedrooms
4 bathrooms

sleeps 8

Match: Rental types

All filters match

Price per night from

$900

Private Villa with a wonderful view and private pool, close to Siena

Siena villa

5 bedrooms
3 bathrooms

sleeps 9

Match: Rental types

All filters match

Price per night from

$442

Villa La Strega

Siena villa

6 bedrooms
6 bathrooms

sleeps 12

Match: Rental types

All filters match

Price per night from

$701

Villa Mocarello between Siena and Florence

Poggibonsi villa

1 bedroom
2 bathrooms

sleeps 2

Match: Rental types

All filters match

Price per night from

$86

casa con piscina panoramica

Chiusdino villa

2 bedrooms
2 bathrooms

sleeps 6

Match: Rental types

All filters match

Price per night from

$148

Vignalsole

Radda in Chianti villa

5 bedrooms
4 bathrooms

sleeps 9

Match: Rental types

All filters match

Price per night from

$787

casa con piscina

Chiusdino villa

2 bedrooms
2 bathrooms

sleeps 2

Match: Rental types

All filters match

Price per night from

$148

Bargagli Penthouse

Pievescola villa

3 bedrooms
4 bathrooms

sleeps 6

Match: Rental types

All filters match

Price per night from

$2,164

Giunia

San Lorenzo a Merse villa

14 bedrooms
14 bathrooms

sleeps 27

Match: Rental types

All filters match

Price per night from

$2,735

Villa Cypress

Castelnuovo Berardenga villa

9 bedrooms
8 bathrooms

sleeps 12

Match: Rental types

All filters match

Price per night from

$1,660

Morgana

Buonconvento villa

9 bedrooms
9 bathrooms

sleeps 18

Match: Rental types

All filters match

Price per night from

$1,705

Castello di Montalto - 3 Bedroom Villa in Chianti

Siena villa

3 bedrooms
2 bathrooms

sleeps 6

Match: Rental types

All filters match

Price per night from

$407

One Bedroom Villa at Castello di Montalto in Chianti

Siena villa

1 bedroom
1 bathroom

sleeps 2

Match: Rental types

All filters match

Price per night from

$172

Podere Lucignano Secondo - Apt. La Mangiatoia (ground floor)

Nusenna villa

2 bedrooms
1 bathroom

sleeps 4

Match: Rental types

All filters match

Price per night from

$295

Le Pratola Luxury Villa in Chianti with Heated Pool, top rated reviews.

Gaiole in Chianti villa

5 bedrooms
6 bathrooms

sleeps 13

“Unforgettable Vacation!” My family and I (six of us) stayed at Le Pratola for a week in June. We had such a great time. The villa is beautiful and comfortable, and the views of the Tuscan hills are stunning. The team at Le Pratola is amazing. Laura, the cleaning lady, is a doll. The cooking class with Barbara is so much fun! Elena and Monica's (the personal chefs) meals are delicious. The villa is beautifully decorated and so comfortable. We all had the best vacation! We will definitely recommend the villa to family and friends. It was the best trip we've ever been on! We would like to thank the team at Le Pratola for making our vacation to Tuscany so special.

Match: Rental types

All filters match

Price per night from

$2,368

Villa Oliveto

Castelmuzio villa

5 bedrooms
6 bathrooms

sleeps 10

Match: Rental types

All filters match

Price per night from

$668

Siena San Fabiano climatized villa with outdoor heated pool

Monteroni d'Arbia villa

9 bedrooms
6 bathrooms

sleeps 18

“Perfect combo of charm, location & comfort in glorious Tuscany!” We first dicovered San Fabiano in summer 2003 and have made it a point to return with family and friends as often as we can ever since! The location is ideal for exploring Siena, all the hill towns of southern tuscany, the Chianti and even great for easy day trips to Florence. Besides the charm of this renovated farmhouse - it also has modenr comforts like ac, screened windows, kitchenettes in all the rooms and wireless internet - plus a swimming pool! We love walking into the little town of Monteroni for our morning cappucinos and hiking the trails around this lovely farm estate. Great for kids and family gatherings as well as couples. We get through New England winters by dreaming of returning to San Fabiano. Highly recommended!

Match: Rental types

All filters match

Price per night from

$1,228

Tuscany Villa with pool - Villa le Capanne holday in private villas

Siena villa

3 bedrooms
3 bathrooms

sleeps 7

“Fantastic Hosts for this unique countryside Villa” Our trip to Italy still fresh in our minds so we wanted to write to tell others about our lovely experience at Villa le Capanne. We stayed with another couple for one week, make trips to Florence, Voltera, Pisa and more. Gina and Franco met us and welcomed us with enough goodies to keep us well taken care of until we could shop. Each day, a new treat appeared and they were all yummy-Gina is a fantastic baker and cook. The villa was spotless and just as described. Let me just say that the location is a bit of a challenge, but worth it for the views. Sitting around the pool and gazebo was very relaxing. You may need to allow extra time to get to the main roads for day trips but if you are prepared, it is not a problem. We had some great fun at the local restaurant, pizza on the weekend and then dinner on another night. The little village, Montecastelli Pisano was charming and we walked on a quiet street and found a violin maker who played us one of his own compositions-unique experience! Great hosts in a lovely setting!

Responds fast! avg. 2 hours 23 minutes

Match: Rental types

All filters match

Price per night from

$115

Cozy Collection of Villas in Tuscany

Montalcino villa

14 bedrooms
14 bathrooms

sleeps 26

“Great stay- we hope to return!” We truly enjoyed our stay here. Matteo was a wonderful host and even met us outside of town to make sure that we did not get lost on the way to the agriturismo. The room was clean and very comfortable, especially important since we brought our 3 month old baby. The kitchenette was very useful and had everything we needed. This was a perfect place to stay while in town for Benvenuto Brunello because it allowed us a gorgeous drive and was away from crowds. We even enjoyed Quercecchio's wine, both Brunello and Rosso. Next time, we hope to visit around harvest time!

Match: Rental types

All filters match

Price per night from

$1,694

Villa Patrignone - a beautiful large Tuscany Villa

Castellina In Chianti villa

7 bedrooms
7 bathrooms

sleeps 14

“My favorite vacation experience” My first trip to Podere Patrignone was in 1999, and I've been back four times since my initial visit. The setting is incredible, and the views extend to miles and miles of Tuscany. It's amazing to sit on the terrace and see the towers of San Gimignano far in the distance. The villa is located just 3 kilometers from Castellina in Chianti, a charming village with unbelievable shopping for leather goods (Cappelletti), artwork, and other wonderful Tuscan items. Patrignone is a perfect location for day trips to Florence, Siena, Montalcino, and many other wonderful towns filled with incredible history. Back to the villa...Simon and Verity are carrying on the tradition of Simon's mom Carla, who renovated this beautiful villa that was originally a 14th century farmhouse. The main house has 7 rooms (each with its own bathroom...no sharing!), a great kitchen, and lots of space for lounging and relaxing. I've stayed in the main house as well as each of the 2-bedroom apartments...each with its own kitchen and living area. They all are wonderful, clean, charming, and have beautiful views. This year I participated in a cooking class conducted by Verity. Even after multiple cooking classes that I've taken throughout Italy, I can say that this was one of the best learning experiences: Verity is a fantastic teacher, cooking all the courses was great fun, and we got to dine and wine on our results. She cooked dinner for all of us on our first night, and everything was delicious! There were 18 of us on this trip, although I've been here with as few as one other person. I have lots of other friends who are encouraging a return trip. This year was in the last week of May, but I think we'll return for a visit in September next year. Carla and Simon and Verity have created a paradise that continues to call to me even after all these years and visits. Podere Patrignone is absolutely amazing and I can't wait to return!

Match: Rental types

All filters match

Price per night from

$608