San Donnino vacation rentals

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August 2025

September 2025

Scroll through and select from vacation rentals in San Donnino to find one that's perfect for your trip. Whether you're traveling with a group or just with your pet, vacation homes have the amenities you need and want for your stay, which might include WiFi and a washer and dryer, No matter what you're looking for, you'll be sure to find a rental to meet everyone's needs, including a place that's non-smoking or offers accessibility.

Vacation rentals with weekly discounts - San Donnino

Showing deals for:Nov 14 - Nov 21

Exceptional

(16 reviews)

Exclusive panoramic villa with private pool between Florence and Siena.

Certaldo, Toscana

10% off

includes taxes & fees

Charming Tuscan Villa Albertina surrounded by lush greenery

Exceptional

(7 reviews)

Splendid Chianti Tuscany Villa with Panoramic Pool ,Cypress Trees-Lined Drive

Montespertoli, Città Metropolitana di Firenze

10% off

includes taxes & fees

Exceptional

(38 reviews)

VILLA BELSOLE - Certaldo Tuscany HEATED POOL and electric car recharge

Certaldo, Tuscany

19% off

includes taxes & fees

Exceptional

(23 reviews)

Breathtaking views of the Chianti hills, Tradition, Sustainability and Design

Montespertoli

10% off

includes taxes & fees

Exceptional

(18 reviews)

Happy holidays in Chianti, among olives and vineyards, From Florence

San Casciano in Val di Pesa, Toscana

5% off

includes taxes & fees

Exceptional

(18 reviews)

FALCO: Peaceful farmcottage close to Tuscany 's treasures, 1 mile from shops

Poggibonsi, Tuscany

10% off

includes taxes & fees

Exceptional

(25 reviews)

Agriturismo San Silvestro - Your home with pool in the hills of Chianti

Barberino Val d'Elsa, Tuscany

10% off

includes taxes & fees

Exceptional

(57 reviews)

Holiday home in the Florentine Chianti half an hour from Florence

Montespertoli, Toscana

10% off

includes taxes & fees

Exceptional

(96 reviews)

San Gimignano villa with pool, 5 rooms en suite, A/C, wi-fi, panoramic view

San Gimignano, SI, Italy

10% off

includes taxes & fees

Private bedroom with it's own bathroom. Door walks out to the outdoor patio.

Exceptional

(8 reviews)

Tuscan house on vineyard hilltop tucked inside lush gardens

San Casciano in Val di Pesa, Toscana

15% off

includes taxes & fees

Wonderful

(10 reviews)

Lovely country house in the Chianti region, for 4 persons, near Siena

Castellina in Chianti, Tuscany

15% off

includes taxes & fees

Exceptional

(28 reviews)

RELAX BETWEEN OLIVES AND WINEYARDS IN THE CHIANTI, ONLY 35MINUTES FROM FLORENCE!

San Casciano in Val di Pesa, Tuscany

8% off

includes taxes & fees

Exceptional

(15 reviews)

RONDINE: Peaceful farmhouse close to Tuscany 's treasures, 1mile from shops far

Poggibonsi, Tuscany

10% off

includes taxes & fees

Exceptional

(15 reviews)

GUFO: Peaceful apartment close to Tuscany 's best treasures, 1 mile from shops

Poggibonsi, Tuscany

10% off

includes taxes & fees

Wonderful

(10 reviews)

PETIROSSO: Peaceful apt close to Tuscany 's best treasures, 1 mile from shops

Poggibonsi, Tuscany

10% off

includes taxes & fees

Exceptional

(51 reviews)

Typical dwelling in the heart of the Tuscany between FLORENCE and SIENA

San Gimignano, Tuscany

5% off

includes taxes & fees

Wonderful

(20 reviews)

PASSERO:Peaceful farmhouse close to Tuscany 's best treasures, 1 mile from shops

Poggibonsi, Tuscany

10% off

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - San Donnino

Pure Tuscany with an idyllic villa and exceptional views

Sleeps 5 · 2 bedrooms · 1+ bathroom

Top rated rentals - San Donnino

Charming Villa

Beautiful country setting on a hill near Poggibonsi with a stunning view of San Gimignano. Good restaurants in Poggibonsi about 9 kilometres away. You must book winery visits in advance Very well appointed villa, especially the kitchen. Enjoyed our week in May

Randy R.

Stayed May 2025

Great location

The area and villa are in the heart of great touristic area. Everything's was easy and the owner very helpful.

Daniela T.

Stayed Oct 2024

Premier Host

Breathtaking Property

Located in one of the prettiest areas of Tuscany, this is a beautiful property. Our host and owner Alessandro was a true pleasure to deal with. Like dealing with a family member, he was attentive, kind, informative, helpful, and truly interested in making sure we were comfortable and had everything we needed. Alessandro was kind enough to set up our dinners with local cooks - who were two beautiful ladies that cooked with joy and passion, and really cared about their food - local favourites. If anything our only complaint was we ate too much! We had a fairly large group and my wife and I were also looking after our 2 year old grandson for the week while his parents honeymooned. Despite the mix, we each had our own bedrooms and own bathrooms, so the house was perfect for this large ecliptic family. The house is perfectly laid out inside, and outside there are plenty of spaces to walk, reflect, play (very nice pool), or just relax and mingle. Overall, we can't say enough about our experience and we're very grateful to Alessandro for his hospitality and for providing such a beautiful place for our family. I would recommend this property to anyone looking to stay in the heart of Tuscany!

Victor S.

Stayed Oct 2024

Perfect and centrally located to visit all of Tuscany

We had a great stay and we were in the perfect area to visit many places around Tuscany.

Jasmin S.

Stayed Oct 2024

quick surprise getaway

With a last minute decision to surprise a friend for his birthday, this was a perfect place to land. Peaceful, spotless, great location and more than comfortable!

Dana W.

Stayed Sep 2024

Premier Host

Fantastic stay for 4 weeks

We spent 4 weeks in this house .The owner was very helpfull the house was top notch If You want to ear the silence it is one of the best place House was what were expected and more I recommand this house for people need to relax in peace and calm A special Thanks to the MAMMA

Pierre B.

Stayed Jun 2024

Premier Host

Quiet, Relaxing Villa in a Beautiful Village!

When we arrived the owner met us at the appartment and showed us around. His communication with us was great leading upto our arrival. The setting of this place is absolutely amazing. So quiet and beautiful. The views from both sides of the house are wonderful. We played tennis on the court with such an outstanding view. The pool looks great too, but it was out of season for us. Well located to visiting various hill top towns. We also did a wine tour at one of the many wineries in the area which I highly recomend (We did Monsanto, but there are lots of options in the area). The kitchen was very well equiped and everything was in good working order in the house. We cooked here every day. The rooms are large and we were very comfortable for our 5 day stay in April. It's essential you have a car. If you are looking to get away from the bustle of the city and have a relaxing and quiet setting close to midevil towns and wineries, this place is a terrific option.

Travis P.

Stayed Apr 2024

End of a exiting afternoon. Some drinks at the Pool.

Beautiful property and an Amazing host

My wife and I have stayed in dozens of different VRBO properties around the world and actually used to own one where we never received less than a five star review so we know a great property when we find one. I will honestly say this is the cleanest I have ever found a rental house, absolutely immaculate. They take all of the bedding offsite to be professionally cleaned and I felt like I was staying in a high-end hotel. The fireplace was fantastic and we had unlimited firewood for beautiful fires every night. Jerome is an incredible host with fantastic communication and he gets back to you every time very quickly. The property itself is very secluded and private, and we did not hear another sound other than many birds. The local town of Castellina was wonderful and we tried many restaurants that Jerome recommended and they were all great! Book this property you will not be disappointed.

Chris B.

Stayed Mar 2024

Peace of mind
Our Book with Confidence guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, yards and more
More for less
More space, more privacy, more amenities — more value

Find out more about San Donnino

Book a vacation rental for your San Donnino getaway

Learn about the unique charm of San Donnino with a stay in a private vacation home. You'll find plenty to explore during your stay in the area. Many of our vacation rentals offer full kitchens, spacious living quarters, and sometimes even a hot tub for a relaxing getaway.

Activities and attractions in San Donnino

Do you want to find attractions to visit in the area? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that makes San Donnino a one-of-a-kind vacation spot. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city center:

Tenuta Torciano Winery (3.1 mi / 5 km)
Castello di Monsanto (4.5 mi / 7.3 km)
Castello della Paneretta (4.6 mi / 7.4 km)
Casa Sola - Chianti Winery (5.2 mi / 8.4 km)
Antinori nel Chianti Classico (5.9 mi / 9.6 km)
Isole e Olena Winery (6 mi / 9.7 km)

Exploring the natural features in San Donnino

Whether you're looking for fun outdoor activities or just want to spend some time taking in the scenery, San Donnino is a great place to spend some time outside. These are some of the area's most stunning sights, all within 30 miles (48.2 km) of the city center: