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Featured Villas in Certaldo and around

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

10.0 out of 10, Exceptional, (97)
"The location and views were absolutely spectacular! Alessandro was EXTREMELY helpful and accommodating. He helped arrange for chef and wine tasting at the villa and they were memorable. "
San Gimignano villa with pool, 5 rooms en suite, A/C, wi-fi, panoramic view

Villa Sabrina - Luxury Villa Rental with private swimming pool in San Gimignano, Tuscany

10.0 out of 10, Exceptional, (80)
"Great place. Great host Driveway….needs work "
Villa Sabrina - Luxury Villa Rental with private swimming pool in San Gimignano, Tuscany

Villa in Poggiarello-ripa with 3 bedrooms sleeps 5

10.0 out of 10, Exceptional, (110)
"We loved our stay, it was beautiful and relaxing beyond words! Francesca and her team were amazing, providing so many memorable experiences and great support! We will be back! What a wonderful time all around. "
Villa in Poggiarello-ripa with 3 bedrooms sleeps 5

Villa Boccaccio

2.0 out of 10, (1)
"Keiner Vor-Ort gewesen. Es war kein Check In möglich trotz Buchungsbestätigung"
The price is €154
includes taxes & fees
16 Aug - 17 Aug
Villa Boccaccio

Villa Costa, Stunning Villa in the heart of Tuscany.

10.0 out of 10, Exceptional, (36)
"You have all the amenities of a large, historic villa - and also the real farmland all around you. Sheep, horses, dogs - beautiful, and not in your personal space (unless you want them to be!). Pasqualina and her son Francesco are perfect hosts. Incredibly responsive, even with a language barrier. If I return to Tuscany I would want to stay here again. Thank you so much."
Villa Costa, Stunning Villa in the heart of Tuscany.

Villa with pool, 4 rooms en suite, WiFi A/C, walking distance from San Gimignano

10.0 out of 10, Exceptional, (108)
"We had a lovely stay at the villa. The villa was comfortable, well furnished and had a beautiful view of San Gimignano. The owner was very helpful and responsive. We will definitely stay there again if we visit San Gimignano."
Villa with pool, 4 rooms en suite, WiFi A/C, walking distance from San Gimignano

Stunning Villa: 24 guests, private SwimmingPool

9.8 out of 10, Exceptional, (28)
"We had a fantastic time at the house, Fabio was excellent in his communication and help. The house is great with separate areas but big communal spaces. We had a couple of delicious meals cooked for us by Fabio, I would highly recommend this luxury! If I had to say one thing it would be great if the pool seating area was tiled instead of grass, but overall can't fault it."
Stunning Villa: 24 guests, private SwimmingPool

Villa Le Balze Large Private Pool, WiFi

9.8 out of 10, Exceptional, (19)
"An excellent choice for a worry-free and comfortable stay."
Villa Le Balze Large Private Pool, WiFi

BEAUTIFUL VILLA with private Pool in the heart of Chianti

10.0 out of 10, Exceptional, (25)
"We celebrated our baby turning 1 with family and friends and this property was an absolute dream! It comfortably fit our large group! We had a private chef host a dinner for us that Alessandro requested which was incredible! We are grateful for the family memories and would 100% return! Thank you for being such a great host! "
BEAUTIFUL VILLA with private Pool in the heart of Chianti

Villa Salivolpe - on top of a Chianti hill - Private swimming pool

9.6 out of 10, Exceptional, (22)
"The villa was a beautiful home to send our our time in Tuscany, Italy. We enjoyed having our own bedrooms and baths. We had a special meal cooked by a local chef, Rachel. The kitchen worked well for the cooking, and for our breakfasts. The scenery was just breathtaking, and it is just as pictures in books looked like. We very much enjoyed our stay."
Villa Salivolpe - on top of a Chianti hill - Private swimming pool

Luxury Villa Basilio Chianti

Luxury Villa Basilio Chianti

Your panoramic house in Tuscany between vineyards and olive groves.

9.8 out of 10, Exceptional, (40)
"We had such a nice stay and only wish it had been longer! Enrico & Simona were excellent hosts and we loved the cooking class they did for us and our 3 college students who learned to make pasta for the first time. The views are spectacular and it’s a perfect location for trips to the many surrounding towns and wineries. We’d love to come back in the summer and stay longer!"
Your panoramic house in Tuscany between vineyards and olive groves.

Quiet and Beautiful Property, Large Pool, Airco in bedrooms

10.0 out of 10, Exceptional, (53)
"The house was fantastic and had more than enough space for our large family. What was particularly great was the large table where we always ate before we went to the very large swimming pool."
Quiet and Beautiful Property, Large Pool, Airco in bedrooms

Relais Badia a Passignano

10.0 out of 10, Exceptional, (1)
Relais Badia a Passignano

Luxury Villa with Swimmingpool in Chianti/Sleeps 21 - or more in extra suites

10.0 out of 10, Exceptional, (38)
"Excellent in every way. Highly recommend"
The price is €1,829
includes taxes & fees
16 Aug - 17 Aug
Luxury Villa with Swimmingpool in Chianti/Sleeps 21 - or more in extra suites

Elegante villa con piscina a soli 12 km da Firenze ideale per famiglie e gruppi

10.0 out of 10, Exceptional, (1)
"We had a wonderful stay at this beautiful, traditional Italian villa. Cosimo was a fantastic host—warm, approachable, and incredibly helpful throughout our stay. The villa itself is charming and authentically Tuscan, with multiple floors. While the stairs and layout may be something to consider for those with mobility issues or very young children, we were a mixed group of six (including older and younger guests) and found it worked well and was very spacious The home is brilliantly equipped...
Elegante villa con piscina a soli 12 km da Firenze ideale per famiglie e gruppi

Beautiful Villa With Panoramic Views near San Gimignano

9.6 out of 10, Exceptional, (73)
"Nice area! We enjoyed the terasse and the pool a lot "
Beautiful Villa With Panoramic Views near San Gimignano

Villa with unique view of Siena with private pool

10.0 out of 10, Exceptional, (6)
"I booked Letizia's amazing Villa for a week-long birthday celebration and we loved every minute of our time in the Tuscan sun! It was great to be able to relax by the pool in the peace of the countryside amongst the olive groves while still being only a short walk away from Siena, we just wish we could have stayed for longer!"
Villa with unique view of Siena with private pool

Villa Casa al Sole Large Private Pool, WiFi

9.8 out of 10, Exceptional, (21)
"Thank you for a fantastic experience - everything was just right."
Villa Casa al Sole Large Private Pool, WiFi

4-bedroom stonehouse with stunning pool in the Chianti countryside with WiFi, AC

8.0 out of 10, Very good, (1)
"We spent a great family time at Adme’s house.The house has everything. Was very clean and well maintained . Will highly recommend."
4-bedroom stonehouse with stunning pool in the Chianti countryside with WiFi, AC
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Certaldo Hotel Reviews

Frequently asked questions

How much do villas in Certaldo cost?
Villas in Certaldo cost between €154 and €1,829 per night. These stays give you the privacy to enjoy your own space at a price that's easy on your wallet. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many villas are there in Certaldo?
Certaldo has 2055 villas to pick from. Find a place that's right for you quickly and easily by selecting the "Villa" checkbox under the "Property type" tab in our filter tool.
Why book your villa in Certaldo with Expedia?
Booking a villa in Certaldo is as simple as working out your travel dates and picking a place that meets your needs. Want something low cost or luxurious, or a stay that also features WiFi and a hot tub? Use Expedia's search filters to narrow your results and find the perfect pad.