A historic castle on a hill surrounded by lush greenery.

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Certaldo villas

A covered balcony with a brick railing, a bench, and a view of lush greenery.

1. Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany

Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany
Certaldo - Firenze
2.0 out of 10, (1 review)
"House is very nice and clean , but not equipped for rental, kitchen is poorly equipped, towels are like napkins , no toilet paper, no soap , nothing "
United States
Kelly C.
The price is €1,162
includes taxes & fees
2 Nov - 3 Nov
Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany
A garden with outdoor seating, a shade structure, and a view of the surrounding landscape.

2. Rooster House, Cooking Classes, and Opera

Rooster House, Cooking Classes, and Opera
Tavarnelle Val di Pesa
The price is €135
includes taxes & fees
1 Nov - 2 Nov
Rooster House, Cooking Classes, and Opera
A stone building with an arched entrance, surrounded by gravel, potted plants, and trees.

3. Villa Montecastello

Villa Montecastello
Monteriggioni
8.0 out of 10, Very good, (3 reviews)
"Amazing stay! Teh apartment is HUGE and GORGEOUS. The whole villa is amazing. The view , unbeatable. The host , super warm. Highly recommend!"
United States
Alvaro
The price is €353
includes taxes & fees
14 Nov - 15 Nov
Villa Montecastello
A person in a swimming pool with a view of a vineyard and hills.

4. "A Casa di Franca Villa con piscina"

"A Casa di Franca Villa con piscina"
Gambassi Terme
10.0 out of 10, Exceptional, (1 review)
"Pros: La estancia en la casa fue muy bonita. Estaba cerca de Florencia, Siena, Sant Gimigano, etc. Viajamos toda la familia y los propietarios fueron muy acogedores. La piscina es un sitio perfecto para relajarse y bañarse después de ver la Toscana. Nuestros hijos y sobrinos jugaron porque tenían de todo. La casa muy equipada y limpia con televisión en todas las habitaciones. Los propietarios además nos ayudaron con un pequeño contratiempo que tuvimos. Nos sentimos como en casa, muchas...
Spain
Anonymous traveller
The price is €1,527
includes taxes & fees
2 Nov - 3 Nov
"A Casa di Franca Villa con piscina"
A villa with a swimming pool, surrounded by lush greenery and vineyards.

5. Villa with Guesthouse: Private Pool, Air Conditioning, 13 Bedrooms for up to 30 Guests

Villa with Guesthouse: Private Pool, Air Conditioning, 13 Bedrooms for up to 30 Guests
Montespertoli
The price is €5,404
includes taxes & fees
2 Nov - 3 Nov
Villa with Guesthouse: Private Pool, Air Conditioning, 13 Bedrooms for up to 30 Guests
A building with a large entrance, potted plants, and a statue in the foreground.

6. Villa Milani with Shared Pool, Private Terrace & Wi-Fi

Villa Milani with Shared Pool, Private Terrace & Wi-Fi
Montespertoli
10.0 out of 10, Exceptional, (1 review)
"The Villa was charming and absolutely bursting with character. We loved exploring the house and the grounds! It was quiet and relaxing, but still only a short drive from Florence, Sienna, San Gimignano and other favorite towns of Tuscany. A memorable stay in an absolutely unique villa!"
United States
Scott M.
The price is €1,622
includes taxes & fees
2 Nov - 3 Nov
Villa Milani with Shared Pool, Private Terrace & Wi-Fi
A two-story building with a gravel driveway, a wooden door, and a small garden area with potted plants.

7. Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites

Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites
Montespertoli
10.0 out of 10, Exceptional, (42 reviews)
"Absolutely fabulous! Beautiful location, exceptional host and the Tuscan countryside dream. Room for all 11 of our ladies, dreamy grounds. We all felt like we were living our Eat, Love, Pray best life!"
United States
Krista G.
The price is €1,431
includes taxes & fees
29 Nov - 30 Nov
Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites
A modern poolside area with a clear view of the landscape.

8. Aureva Tuscany, modern villa with private pool

Aureva Tuscany, modern villa with private pool
Montelupo F.no
Aureva Tuscany, modern villa with private pool
A courtyard with a building, potted plants, and a grassy area.

9. SwimmingPool ONLY FOR YOU in Villa with AirCon for 26/30 pax in 13 bedrooms

SwimmingPool ONLY FOR YOU in Villa with AirCon for 26/30 pax in 13 bedrooms
Toscana
The price is €2,238
includes taxes & fees
2 Nov - 3 Nov
SwimmingPool ONLY FOR YOU in Villa with AirCon for 26/30 pax in 13 bedrooms
An outdoor patio with a table and chairs, surrounded by greenery and a view of distant hills.

10. Luxury Villa in the Florentine hills

Luxury Villa in the Florentine hills
Florence
9.8 out of 10, Exceptional, (152 reviews)
"The villa is a nicely restored rustic home with a beautiful landscape. I would definitely stay there again!"
United States
melissa r.
The price is €347
includes taxes & fees
1 Nov - 2 Nov
Luxury Villa in the Florentine hills
A table set for tea with a view of a garden and hills.

11. Tuscan Sky Villa in San Miniato with Private Pool

Tuscan Sky Villa in San Miniato with Private Pool
San Miniato
The price is €1,040
includes taxes & fees
1 Nov - 2 Nov
Tuscan Sky Villa in San Miniato with Private Pool
A stone building with a large arched entrance, potted plants, and outdoor seating.

12. Exclusive Estate | Personal Concierge & Heated Pool

Exclusive Estate | Personal Concierge & Heated Pool
impruneta
10.0 out of 10, Exceptional, (115 reviews)
"We had a great time with the family in impruneta. Caterine - the host - was very friendly and made everything to have a perfect stay in the villa. We can absolutely recommend this villa !"
Germany
Oli P.
The price is €1,024
includes taxes & fees
3 Nov - 4 Nov
Exclusive Estate | Personal Concierge & Heated Pool
A rural property with stone buildings, a garden, and a view of rolling hills.

13. Villetta Brunelleschi: Privacy and Comfort on Two Levels

Villetta Brunelleschi: Privacy and Comfort on Two Levels
Montaione
Villetta Brunelleschi: Privacy and Comfort on Two Levels
A multi-story building with a stone pathway leading to the entrance, surrounded by lush greenery and flowering plants.

14. VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
Firenze
The price is €14,160
includes taxes & fees
1 Nov - 2 Nov
VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
An open wooden door leading to a balcony with a round table and two chairs, overlooking a garden with trees and flowers.

15. Florence‼️~Entire villa in the hills, sleeps 7, 4 bathrooms~

Florence‼️~Entire villa in the hills, sleeps 7, 4 bathrooms~
Impruneta
10.0 out of 10, Exceptional, (4 reviews)
"Super quaint, beatiful, designed, comfortable, not lacking anything house and location. Very informative and accessable host. Listen to the instructions on how to go to Firenze. No need to take your car tyere!"
United States
Maria H.
Florence‼️~Entire villa in the hills, sleeps 7, 4 bathrooms~
A stone patio with outdoor furniture, a stone wall, and a view of the countryside.

16. Golden Hour - Wedding in Florence

Golden Hour - Wedding in Florence
Toscana
The price is €2,984
includes taxes & fees
12 Nov - 13 Nov
Golden Hour - Wedding in Florence
A two-story building with a stone staircase leading to a wooden door. There is a small outdoor table and a potted plant on the porch.

17. Villa Il Signorino

Villa Il Signorino
GREVE IN CHIANTI
9.4 out of 10, Exceptional, (3 reviews)
"Nice place 👌 "
United States
Avi A.
The price is €456
includes taxes & fees
1 Nov - 2 Nov
Villa Il Signorino
A stone building with a swimming pool, wooden deck, and a tall tree.

18. Villa 'La Petrosa' with Private Pool, Private Garden and Balcony

Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
Radda in Chianti
7.4 out of 10, Good, (3 reviews)
"RUN as fast as you can. Booked this place and left hours after. Here is why:1. It is actually part of a commune. Numerous other building that don't appear in pictures or description on VRBO2. There are 2 separate units. One up, One down. Require separate entrance3. Downstairs bathroom flooded. Owner admits to a broken pipe in the wall, so says use the other 2 upstairs. So, go outside, upstairs, unlock the door to use the bathroom in the middle of the night? We decide to sleep upstairs with the...
United States
JIm B.
The price is €1,078
includes taxes & fees
2 Nov - 3 Nov
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
An outdoor patio with a table and chairs, surrounded by potted plants and overlooking a scenic view of hills and buildings.

19. Tuscan villa 15 minutes from Florence, parking, garden

Tuscan villa 15 minutes from Florence, parking, garden
Pian di Mugnone
10.0 out of 10, Exceptional, (3 reviews)
"We had a wonderful stay! The kids loved the layout, and we were very comfortable!"
United States
Rebecca P.
Tuscan villa 15 minutes from Florence, parking, garden
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

The Social Hub Florence Belfiore

The Social Hub Florence Belfiore

10/10 Excellent
"The staff were super welcoming, helpful and friendly."
Xiara 2-night trip
Posted 1 hour ago
The Social Hub Florence Belfiore

Find out more about Certaldo

Certaldo Villas information

Number of reviews
328
Accommodation
1748 Villas
Lowest Price
€135
Highest Price
€14,160

Frequently asked questions

How much do villas in Certaldo cost?
Villas in Certaldo cost between €135 and €14,160 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 1748 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.
How can I find cheap villas in Certaldo?
Expedia can help you track down cheap villas in Certaldo. Simply use our handy filter tool to choose amenities, star rating and budget to refine your search and find a great place to stay in a few quick keystrokes.
What is there to do near my villa in Certaldo?
If you're eager to explore the best of Certaldo, make your way to Museum of Sacred Art. It's a winner with locals and visitors alike.