A rural landscape with olive groves, scattered houses, and rolling hills in the background.

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Our top choices for Montespertoli villas

1. 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 AU$8,576
includes taxes & fees
4 Nov - 5 Nov
Villa with Guesthouse: Private Pool, Air Conditioning, 13 Bedrooms for up to 30 Guests

2. 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 AU$2,199
includes taxes & fees
29 Nov - 30 Nov
Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites

3. 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 AU$2,574
includes taxes & fees
4 Nov - 5 Nov
Villa Milani with Shared Pool, Private Terrace & Wi-Fi

4. Luxury,Charming,in true Chianti, sleeps 21 or +people with Sw-Pool,Wi-Fi,Airco

Luxury,Charming,in true Chianti, sleeps 21 or +people with Sw-Pool,Wi-Fi,Airco
Montespertoli
10.0 out of 10, Exceptional, (12 reviews)
"Amazing Property! The house was impeccably clean, with spacious bedrooms and comfortable beds. Our gracious host Nicola spoiled us with his generosity. He went beyond our expectations to ensure that our stay was perfect. He and his wife welcomed us with a delicious homemade apple cake. He drove us to the nearby town of Montespertoli to pick-up groceries and provisions. He recommended a local chef to cook for us at the villa. The meal was amazing and memorable. We will be back!"
United States
Elise D.
The price is AU$2,817
includes taxes & fees
4 Nov - 5 Nov
Luxury,Charming,in true Chianti, sleeps 21 or +people with Sw-Pool,Wi-Fi,Airco

5. 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 AU$3,320
includes taxes & fees
4 Nov - 5 Nov
SwimmingPool ONLY FOR YOU in Villa with AirCon for 26/30 pax in 13 bedrooms

6. Rooster House, Cooking Classes, and Opera

Rooster House, Cooking Classes, and Opera
Tavarnelle Val di Pesa
The price is AU$199
includes taxes & fees
4 Nov - 5 Nov
Rooster House, Cooking Classes, and Opera

7. VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
Firenze
The price is AU$22,472
includes taxes & fees
4 Nov - 5 Nov
VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

8. Exclusive Estate | Personal Concierge & Heated Pool

Exclusive Estate | Personal Concierge & Heated Pool
impruneta
10.0 out of 10, Exceptional, (117 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 AU$1,566
includes taxes & fees
4 Nov - 5 Nov
Exclusive Estate | Personal Concierge & Heated Pool

9. 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 AU$1,845
includes taxes & fees
4 Nov - 5 Nov
Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany

10. VILLA MEDICEA - Seven Bedroom Villa, Sleeps 25

VILLA MEDICEA - Seven Bedroom Villa, Sleeps 25
Careggi Rifredi
10.0 out of 10, Exceptional, (1 review)
"Staff went over and above for us. Food was wonderful service 5 stars"
United States
robert g.
The price is AU$14,981
includes taxes & fees
4 Nov - 5 Nov
VILLA MEDICEA - Seven Bedroom Villa, Sleeps 25

11. "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 AU$2,424
includes taxes & fees
4 Nov - 5 Nov
"A Casa di Franca Villa con piscina"

12. Golden Hour - Wedding in Florence

Golden Hour - Wedding in Florence
Toscana
The price is AU$4,556
includes taxes & fees
4 Nov - 5 Nov
Golden Hour - Wedding in Florence

13. Bagno a Ripoli, Italy. Entire property: Villa

Bagno a Ripoli, Italy. Entire property: Villa
Toscana
The price is AU$1,168
includes taxes & fees
4 Nov - 5 Nov
Bagno a Ripoli, Italy. Entire property: Villa

14. 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 AU$562
includes taxes & fees
16 Nov - 17 Nov
Villa Montecastello

15. Villa 'Podere Bucigattolo' with Private Pool, Wi-Fi and Air Conditioning

Villa 'Podere Bucigattolo' with Private Pool, Wi-Fi and Air Conditioning
Serravalle pistoiese
10.0 out of 10, Exceptional, (3 reviews)
"Great villa for lager groups with great view. Very quite location. The road towards the villa is a bit narrow and makes going for a quick grocery trip a bit less easy. The beds and bathrooms are great although from the description we did not deduct that two rooms share a bathroom and are directly connected. The kitchen downstairs is well equipped but a bit small to accommodate 1 large group sharing the whole property. The host and her sister took great care of us and really nice to be able to...
United States
Maarten O.
The price is AU$4,076
includes taxes & fees
4 Nov - 5 Nov
Villa 'Podere Bucigattolo' with Private Pool, Wi-Fi and Air Conditioning

16. Villa with a Pool in Florence / Breakfast, Daily Housekeeping, Air Conditioning, Jacuzzi

Villa with a Pool in Florence / Breakfast, Daily Housekeeping, Air Conditioning, Jacuzzi
Rignano sull'Arno
The price is AU$7,643
includes taxes & fees
4 Nov - 5 Nov
Villa with a Pool in Florence / Breakfast, Daily Housekeeping, Air Conditioning, Jacuzzi

17. VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36

VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36
Colle Val D'Elsa
The price is AU$18,726
includes taxes & fees
29 Nov - 30 Nov
VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36

18. Villa Dei Pavoni - Luxury Villa in the Hills of Florence

Villa Dei Pavoni - Luxury Villa in the Hills of Florence
Toscana
10.0 out of 10, Exceptional, (2 reviews)
"The host was amazing! The property was beautiful. All was seamless! All of our needs were met. Highly recommend! "
United States
Leopard I.
The price is AU$2,641
includes taxes & fees
4 Nov - 5 Nov
Villa Dei Pavoni - Luxury Villa in the Hills of Florence

19. Florence Apartments - Villa Fonte Morgana with Pool

Florence Apartments - Villa Fonte Morgana with Pool
Impruneta
10.0 out of 10, Exceptional, (1 review)
"What a beautiful villa! We thoroughly enjoyed our stay in Tuscan countryside. All rooms were comfortable and large. We were surprised by the lack of body soap and shampoo."
United States
Christine B.
Florence Apartments - Villa Fonte Morgana with Pool

20. Antico Borghetto di Tigliano: Cozy and ideal for families with children

Antico Borghetto di Tigliano: Cozy and ideal for families with children
Vinci
The price is AU$839
includes taxes & fees
4 Nov - 5 Nov
Antico Borghetto di Tigliano: Cozy and ideal for families with children
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 Montespertoli Hotel Reviews

Find out more about Montespertoli

Montespertoli Villas information

Number of reviews
184
Accommodation
1579 Villas
Lowest Price
AU$199
Highest Price
AU$22,472

Frequently asked questions

How much do villas in Montespertoli cost?
Rates for villas in Montespertoli range between AU$199 and AU$22,472 per night. Whatever your budget, you're sure to find something that matches your needs on Expedia. This price was 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 Montespertoli?
Choose from 1579 villas in Montespertoli. No matter if you're taking a trip with the kids or planning a weekend escape with your besties, Expedia will help you find the best space for your crew.
What is there to do near my villa in Montespertoli?
There are tons of awesome things to do and see in Montespertoli. Drop by attractions like Antinori nel Chianti Classico, Montegufoni Castle and Castle of Oliveto. Castello Sonnino, Castle of Poppiano and San Casciano Museum are also visited by many.