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Check prices for these dates

In two weeks
18 Sep - 20 Sep
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Villa del Monte holiday rentals

A courtyard with brick flooring, outdoor tables with umbrellas, and a brick fountain.

1. Borgo Antico Residence

Borgo Antico Residence
Certaldo Alto
10.0 out of 10, Exceptional, (3 reviews)
"Great place to relax take in the local culture and enjoy Tuscany."
United States
jane
The price is ฿2,177
฿3,465 total
includes taxes & fees
26 Sept - 27 Sept
Borgo Antico Residence
A pool area with lounge chairs and umbrellas, surrounded by stone buildings and greenery.

2. Casa Vacanze Le Case

Casa Vacanze Le Case
San Gimignano
9.4 out of 10, Exceptional, (12 reviews)
"Wonderful. Beautiful property, the views were amazing,and it was so clean. A10 out of 10. "
United States
Jackie
The price is ฿4,292
฿4,913 total
includes taxes & fees
17 Sept - 18 Sept
Casa Vacanze Le Case
A view from a window overlooking a rural landscape with fields and a distant mountain range.

3. B&B Palazzo Tortoli

B&B Palazzo Tortoli
San Gimignano City Centre
9.2 out of 10, Wonderful, (64 reviews)
"In the center of town overlooking a plaza (other rooms overlook the valley). Multiple museums, and dining and shopping options within very easy walking distance. The town and surroundings are beautiful."
United States
Harold
The price is ฿5,217
฿5,930 total
includes taxes & fees
23 Sept - 24 Sept
B&B Palazzo Tortoli
An open wooden door leading to an outdoor patio with a table and chairs.

4. Palazzo al Torrione 2

Palazzo al Torrione 2
San Gimignano City Centre
9.2 out of 10, Wonderful, (112 reviews)
"They were very helpful to me when I arrived. I difficulty accessing there messages to me. They put me at ease"
United States
Angela
The price is ฿3,589
฿5,095 total
includes taxes & fees
7 Sept - 8 Sept
Palazzo al Torrione 2
A table with breakfast items and a view of rolling hills.

5. Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Tavarnelle Val di Pesa
8.6 out of 10, Excellent, (117 reviews)
"Front desk was very helpful and very comfortable room. "
United States
Chris
The price is ฿2,660
฿3,003 total
includes taxes & fees
6 Sept - 7 Sept
Chianti Village Morrocco
A building with a wooden door, windows with shutters, and flower boxes.

6. Donna Nobile

Donna Nobile
San Gimignano City Centre
8.2 out of 10, Very good, (166 reviews)
"Very easy checkin, friendly staff. Loved the kitchen area!"
Canada
Treena
The price is ฿2,885
฿3,364 total
includes taxes & fees
4 Oct - 5 Oct
Donna Nobile
A balcony with a view of rolling hills, a table with a book and a bottle, and a chair.

7. Villa San Filippo

Villa San Filippo
4.0 star property
Barberino Val d'Elsa
8.8 out of 10, Excellent, (52 reviews)
"This place was beautiful, quiet like a picture you’d see in the movies"
Canada
Nadia
The price is ฿3,474
฿4,051 total
includes taxes & fees
21 Sept - 22 Sept
Villa San Filippo
A white mobile home with blue shutters, a red roof, and a small deck with white chairs.

8. Camping Boschetto Di Piemma

Camping Boschetto Di Piemma
3.0 star property
San Gimignano
8.8 out of 10, Excellent, (89 reviews)
"Great experience, close to a beautiful city and castle on a hill. "
New Zealand
Anonymous traveller
The price is ฿1,720
฿2,007 total
includes taxes & fees
6 Sept - 7 Sept
Camping Boschetto Di Piemma
A stone-walled room with a wooden desk, a chair, a TV, and a large window with curtains.

9. Tenuta Sant'Ilario

Tenuta Sant'Ilario
Gambassi Terme
9.4 out of 10, Exceptional, (37 reviews)
"Great place, difficult driving access but enjoyable"
United States
Sergio
The price is ฿4,920
฿5,526 total
includes taxes & fees
29 Sept - 30 Sept
Tenuta Sant'Ilario
An outdoor dining area with tables and chairs, candles, and a view of palm trees and greenery.

10. Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.8 out of 10, Exceptional, (100 reviews)
"We love this beautiful exquisitely appointed hotel in a town with unexpected treasures and great food "
United Kingdom
John
The price is ฿5,098
฿5,684 total
includes taxes & fees
25 Sept - 26 Sept
Palazzo Pacini
A garden with a stone pathway, wooden benches, and various potted plants.

11. Antico Borgo il Cardino

Antico Borgo il Cardino
San Gimignano
9.4 out of 10, Exceptional, (85 reviews)
"It was perfect for my one night stop before moving on to another location in Toscana."
United States
Craig
The price is ฿5,544
฿6,289 total
includes taxes & fees
4 Oct - 5 Oct
Antico Borgo il Cardino
A narrow street with stone buildings, a tower, and an archway.

12. Materia Rooms San Gimignano

Materia Rooms San Gimignano
San Gimignano City Centre
10.0 out of 10, Exceptional, (1 review)
"Fantastic all around experience. The rooms were beautiful and clean and this unique mix of rustic modern Italian styling. Located right in the heart of the old city made it very easy to walk everywhere. The service was fantastic, I was able to message the team and within a minute I got the help and had my questions answered. I’d definitely stay there again."
Canada
Bradley
The price is ฿4,105
฿4,706 total
includes taxes & fees
18 Sept - 19 Sept
Materia Rooms San Gimignano
A stone building with a courtyard, a swimming pool, and vineyard fields in the background.

13. Riserva di Fizzano Residence

Riserva di Fizzano Residence
3.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (36 reviews)
"Great place to stay in Tuscany! Very nice breakfast also!"
United States
Janet
The price is ฿6,996
฿7,772 total
includes taxes & fees
8 Sept - 9 Sept
Riserva di Fizzano Residence
An arched entrance with a lantern above, flanked by two potted plants.

14. Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (103 reviews)
"This is an excellent property. Very historic, rustic and with great views across the Tuscan landscapes. Lorenzo and his mother were super duper hosts who took great care of us. The property dates back to 1380 and the rooms are decorated with choicest artifacts that adds greatly to the experience. The location is fantastic too with the local market and restaurants in easy walking reach. The breakfast service is fabulous with many choices and Lorenzo himself is great chef as well! Highly recommend...
United States
Nilesh
The price is ฿8,269
฿9,248 total
includes taxes & fees
3 Oct - 4 Oct
Villa il Fedino
A bedroom with a large bed, two ottomans, a chandelier, and a view through an arched doorway to a dining area.

15. Borgo San Giusto

Borgo San Giusto
Empoli
9.4 out of 10, Exceptional, (44 reviews)
"A lovely overnight stay here! Staff were so accommodating to our limited Italian and the children. Would recommend"
United Kingdom
Lucy
The price is ฿4,588
฿5,161 total
includes taxes & fees
4 Oct - 5 Oct
Borgo San Giusto
An aerial view of a hotel with a swimming pool, outdoor seating area, and well-maintained gardens.

16. Antica Pieve B&B

Antica Pieve B&B
Tavarnelle Val di Pesa
9.4 out of 10, Exceptional, (14 reviews)
"Very nice stay here! Great breakfast and coffee every morning. Great location to tour around to different wineries and towns. Free parking. "
Canada
Jessica
The price is ฿4,171
฿5,505 total
includes taxes & fees
28 Sept - 29 Sept
Antica Pieve B&B
A spacious indoor area with arched windows, wooden furniture, and hanging plants.

17. Relais Villa Olmo

Relais Villa Olmo
Impruneta
9.4 out of 10, Exceptional, (264 reviews)
"Delightful location, comfortable bed, excellent food."
Canada
Rupert
The price is ฿7,573
฿8,445 total
includes taxes & fees
20 Sept - 21 Sept
Relais Villa Olmo

18. La Rocca Romantica

La Rocca Romantica
San Gimignano City Centre
The price is ฿5,197
฿5,908 total
includes taxes & fees
12 Sept - 13 Sept
La Rocca Romantica
An outdoor dining area with tables and chairs, covered by umbrellas, overlooking a scenic landscape.

19. B&B La Fonte del Machiavelli

B&B La Fonte del Machiavelli
San Casciano in Val di Pesa
9.2 out of 10, Wonderful, (84 reviews)
"Very pretty B&B! The rooms are super cozy and feels welcoming! The scenery around is just amazing! The pool was very refreshing and the host very nice! The trail to reach the B&B is narrow make sure you have a small car ;)"
Canada
Alexia
The price is ฿3,962
฿4,511 total
includes taxes & fees
4 Oct - 5 Oct
B&B La Fonte del Machiavelli

20. B&B Le Dimore di Mezza Costa - Home Restaurant & Cooking Classes

B&B Le Dimore di Mezza Costa - Home Restaurant & Cooking Classes
San Casciano in Val di Pesa
9.2 out of 10, Wonderful, (27 reviews)
"The beautiful place, very comfortable, the incredible attention, the breakfast felt like in Homewith a lot of love We hope to return one day"
Mexico
Raymundo
The price is ฿4,070
฿4,630 total
includes taxes & fees
1 Oct - 2 Oct
B&B Le Dimore di Mezza Costa - Home Restaurant & Cooking Classes
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 Villa del Monte Hotel Reviews

Fattoria di Vegi

Fattoria di Vegi

10/10 Excellent
"Amazing! I wish I could have stayed forever!"
Christopher 1-night trip
Posted 23 hours ago
Fattoria di Vegi

Find out more about Villa del Monte

Search for holiday rentals in Villa del Monte on Expedia! You can easily find your home rentals, villas, holiday apartments in Villa del Monte using one of the methods below:

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Look no further and take a look at our great range of rental properties in Villa del Monte!

Frequently asked questions

Can I find holiday rentals in Villa del Monte?

Yes, there are holiday rentals close to the most popular sights in Villa del Monte, or you can select a more secluded option if you're looking for a relaxing stay.

What can I see and do in Villa del Monte?

Explore the area and family-friendly sights such as Chianti Observatory, or get out into nature at a spot like Alta Val d'Elsa River Park. Casa del Boccaccio and Tenuta Torciano Winery are a couple of places you'll find in the wider area.

What are holiday rentals like in Villa del Monte?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Villa del Monte. Holiday rentals offer extras like kitchens and laundry facilities so you'll feel right at home. If you're concerned about a sanitised environment, a holiday rental can provide a sense of privacy away from shared hotel lifts and busy concierge desks while still allowing you to travel. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great choice for families.