Updating...

More filters

Wireless Internet
Air conditioning
Swimming pool
Private pool

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

See all

Less

Pets
Pets allowed
Parking
Car not required

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

See all

Less

City breaks
Walking trips
Tennis in town
Water sports

Horse riding
Cycling trips
Golf within 30mins drive
Mountain Views
Waterfront

See all

Less

381 villas

Sort by:

Siena country house, private pool.

Quercegrossa villa

5 bedrooms
4 bathrooms

sleeps 12

Match: Rental types

All filters match

Price per night from

$705

Great rentals within 20 miles that match your search

Castle in Chianti with private swimming pool, 15 minutes drive from Florence!

San Casciano in Val di Pesa villa

11 bedrooms
10 bathrooms

sleeps 15

Match: Rental types

All filters match

Price per night from

$1,375

Villa in Chianti with heated swimming pool and A/C

Certaldo villa

9 bedrooms
10 bathrooms

sleeps 19

Match: Rental types

All filters match

Price per night from

$578

Vallebuia

San Gimignano villa

5 bedrooms
5 bathrooms

sleeps 10

Match: Rental types

All filters match

Price per night from

$1,234

Bargagli Penthouse

Pievescola villa

3 bedrooms
4 bathrooms

sleeps 6

Match: Rental types

All filters match

Price per night from

$2,167

Giunia

San Lorenzo a Merse villa

14 bedrooms
14 bathrooms

sleeps 27

Match: Rental types

All filters match

Price per night from

$2,739

Leonardo

Lucardo villa

6 bedrooms
6 bathrooms

sleeps 12

Match: Rental types

All filters match

Price per night from

$932

clear

Tavarnelle Val di Pesa villa

10 bedrooms
9 bathrooms

sleeps 20

Match: Rental types

All filters match

Price per night from

$1,897

Villa Cypress

Castelnuovo Berardenga villa

9 bedrooms
8 bathrooms

sleeps 12

Match: Rental types

All filters match

Price per night from

$1,663

Morgana

Buonconvento villa

9 bedrooms
9 bathrooms

sleeps 18

Match: Rental types

All filters match

Price per night from

$1,708

Adorna

Figline e Incisa Valdarno villa

7 bedrooms
7 bathrooms

sleeps 20

Match: Rental types

All filters match

Price per night from

$4,888

Holiday House Le Corniole

Civitella in Val di Chiana villa

4 bedrooms
2 bathrooms

sleeps 10

Match: Rental types

All filters match

Price per night from

$247

cottage in the countryside

San Gimignano villa

2 bedrooms
2 bathrooms

sleeps 5

Match: Rental types

All filters match

Price per night from

$136

Villa Il Palazzo, big garden, swimming pool, in Tuscany

Pergine Valdarno villa

14 bedrooms
11 bathrooms

sleeps 30

Match: Rental types

All filters match

Price per night from

$1,222

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

$770

Suite Il Tinaio. Villa Caprera, Siena Farmhouse.

Siena villa

1 bedroom
1 bathroom

sleeps 4

Match: Rental types

All filters match

Price per night from

$161

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

$409

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

$173

Casa Borgianni. Villa Caprera, Siena Farmhouse.

Siena villa

3 bedrooms
2 bathrooms

sleeps 6

“heavenly” A beautifully appointed home, with mercifully two batherooms, tastefully decorated with all that you need. The kitchen is a dream - everything you need. Lovely crockery, not bottom-of-the-range, and the bed linen also of excellent quality. Easy access to Siena, on the bus-route - useful to go into Siena by bus, because parking can be a nightmare in Siena itself. Lovely view of Siena, from the top floor. So all in all, this is a hard place to beat, if you want a few days, or longer, just to chill-out and relax and you would be forgiven for thinking Maggie Smith is going to come walking up the drive-way...

Match: Rental types

All filters match

Price per night from

$297

La Tuia Vacanze

Montevarchi villa

2 bedrooms
2 bathrooms

sleeps 4

Match: Rental types

All filters match

Price per night from

$250

Beatifull villa with private pool

Monteriggioni villa

2 bedrooms
2 bathrooms

sleeps 6

Match: Rental types

All filters match

Price per night from

$198

The Poacher

San Polo in Chianti villa

3 bedrooms
2 bathrooms

sleeps 5

Responds fast! avg. 49 minutes

Match: Rental types

All filters match

Price per night from

$272

Il Capriolo sleeps 4 + 1 (on request)

San Polo in Chianti villa

2 bedrooms
2 bathrooms

sleeps 5

Responds fast! avg. 49 minutes

Match: Rental types

All filters match

Price per night from

$247

Poggerina luxury private villa with stunning view

Greve in Chianti villa

4 bedrooms
4 bathrooms

sleeps 8

“Beautiful location and villa, gracious and helpful hosts” I researched extensively before choosing this villa and it more than met our expectations. From the first email Emanuele and his family provided excellent service and were accessible and helpful. Moreover, they made us feel like more than paying guests, more like friends. The villa itself was very spacious and roomy, with a kitchen that had everything we needed. The views are spectacular, and it's quiet and peaceful. I would recommend doing both the pizza night and the cooking night. Both were excellent. Our stay couldn't have been any better. We would highly recommend this villa.

Responds fast! avg. 3 hours 16 minutes

Match: Rental types

All filters match

Price per night from

$617

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

$2,381

Villa il Castellaccio farmhouse chianti with pool

Greve in Chianti villa

5 bedrooms
8 bathrooms

sleeps 10

Match: Rental types

All filters match

Price per night from

$556

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

$1,234

Country House Nazzano in Chianti area near S.Gimignano (from 4 to 10 people)

Gambassi Terme villa

5 bedrooms
4 bathrooms

sleeps 10

“Fantastic Location” We spent a wonderful week in this property which was located centrally in the Tuscany Region. Two families were easily accommodated and we were able to link the connecting rooms as if we were in one large family home. Miriam and her husband were helpful, kind and gracious hosts and nothing was ever too much trouble. All the comforts of home and the peace and quiet of an idyllic getaway. We will return to the incredible property...if our friends and family don't beat us to it!

Match: Rental types

All filters match

Price per night from

$371

romantic ancient tuscan villa B&B near Firenze

Barberino Val d'Elsa villa

7 bedrooms
7 bathrooms

sleeps 14

Match: Rental types

All filters match

Price per night from

$988

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

$611