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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Villa del Monte holiday rentals

A stone-walled room with a wooden desk, a chair, a TV, and a large window with curtains.

1. 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 £80
includes taxes & fees
6 Nov - 7 Nov
Tenuta Sant'Ilario
A white mobile home with blue shutters, a red roof, and a small deck with white chairs.

2. Camping Boschetto Di Piemma

Camping Boschetto Di Piemma
3.0 star property
San Gimignano
8.8 out of 10, Excellent, (91 reviews)
"Great experience, close to a beautiful city and castle on a hill. "
New Zealand
Anonymous traveller
The price is £40
includes taxes & fees
18 Oct - 19 Oct
Camping Boschetto Di Piemma
A courtyard with brick flooring, outdoor tables with umbrellas, and a brick fountain.

3. Borgo Antico Residence

Borgo Antico Residence
Certaldo Alto
10.0 out of 10, Exceptional, (4 reviews)
"Great place to relax take in the local culture and enjoy Tuscany."
United States
jane
The price is £76
includes taxes & fees
26 Oct - 27 Oct
Borgo Antico Residence
A pool area with lounge chairs and umbrellas, surrounded by stone buildings and greenery.

4. Casa Vacanze Le Case

Casa Vacanze Le Case
San Gimignano
9.6 out of 10, Exceptional, (14 reviews)
"The property was perfect and the host was so nice and helpful. We would definitely stay there again."
United States
Andrew
The price is £76
includes taxes & fees
9 Nov - 10 Nov
Casa Vacanze Le Case
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, (121 reviews)
"It’s seen its best day a while ago. Basic necessities for an overnight, but I wouldn’t choose it again."
United States
Winonah
The price is £67
includes taxes & fees
18 Oct - 19 Oct
Chianti Village Morrocco
A balcony with a view of rolling hills, a table with a book and a bottle, and a chair.

6. Villa San Filippo

Villa San Filippo
4.0 star property
Barberino Val d'Elsa
8.6 out of 10, Excellent, (56 reviews)
"This place was beautiful, quiet like a picture you’d see in the movies"
Canada
Nadia
The price is £75
includes taxes & fees
28 Oct - 29 Oct
Villa San Filippo
A building with a wooden door, windows with shutters, and flower boxes.

7. Donna Nobile

Donna Nobile
San Gimignano City Centre
8.2 out of 10, Very good, (168 reviews)
"Very easy checkin, friendly staff. Loved the kitchen area!"
Canada
Treena
The price is £67
includes taxes & fees
1 Nov - 2 Nov
Donna Nobile
A narrow alleyway with brick walls, wooden barrels, and potted plants.

8. San Gimignano Apartment in the Heart of Town for 4 People with Fast Wi-Fi and Concierge Service

San Gimignano Apartment in the Heart of Town for 4 People with Fast Wi-Fi and Concierge Service
San Gimignano City Centre
9.8 out of 10, Exceptional, (42 reviews)
"Authentic 13th century building with so much character and charm. The room was very unique and opened to a lovely courtyard. The location was great, and very close to the gate. A full Italian breakfast buffet was offered at a reasonable cost. Laundry service was also available. And the hosts were very friendly and helpful."
United States
Marilyn H.
The price is £131
includes taxes & fees
18 Oct - 19 Oct
San Gimignano Apartment in the Heart of Town for 4 People with Fast Wi-Fi and Concierge Service
A well-maintained garden with a central fountain, surrounded by lush greenery and flowering plants.

9. Tenuta Quadrifoglio

Tenuta Quadrifoglio
Gambassi Terme
10.0 out of 10, Exceptional, (5 reviews)
"A lovely spot for relaxation .The appartments were lovely and comfortable .the only criticism was you do need a car to get any where. It is totally in the middle of nowhere. "
United Kingdom
Geraldine
The price is £109
includes taxes & fees
30 Oct - 31 Oct
Tenuta Quadrifoglio
A bedroom with a large bed, two ottomans, a chandelier, and a view through an arched doorway to a dining area.

10. Borgo San Giusto

Borgo San Giusto
Empoli
9.4 out of 10, Exceptional, (47 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 £83
includes taxes & fees
19 Oct - 20 Oct
Borgo San Giusto
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, (87 reviews)
"It was perfect for my one night stop before moving on to another location in Toscana."
United States
Craig
The price is £113
includes taxes & fees
18 Oct - 19 Oct
Antico Borgo il Cardino
An open wooden door leading to an outdoor patio with a table and chairs.

12. Palazzo al Torrione 2

Palazzo al Torrione 2
San Gimignano City Centre
9.2 out of 10, Wonderful, (114 reviews)
"Great location, beautiful room with a terrace and the best breakfast we had in Italy! "
United States
Angel
The price is £101
includes taxes & fees
17 Nov - 18 Nov
Palazzo al Torrione 2
A reception desk with the word "SPORTLAND" prominently displayed.

13. Sportland

Sportland
Colle di Val d'Elsa
7.2 out of 10, Good, (5 reviews)
"Struttura essenziale ed economica "
Italy
Giorgio
The price is £39
includes taxes & fees
18 Oct - 19 Oct
Sportland
An outdoor dining area with tables and chairs, candles, and a view of palm trees and greenery.

14. Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.6 out of 10, Exceptional, (103 reviews)
"We love this beautiful exquisitely appointed hotel in a town with unexpected treasures and great food "
United Kingdom
John
The price is £125
includes taxes & fees
29 Oct - 30 Oct
Palazzo Pacini
A narrow street with stone buildings, a tower, and an archway.

15. 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 £88
includes taxes & fees
17 Nov - 18 Nov
Materia Rooms San Gimignano
A garden with a round table and wicker chairs under a tree.

16. Antica Dimora Leones

Antica Dimora Leones
Palaia
9.2 out of 10, Wonderful, (20 reviews)
"What a truly special place to stay in Tuscany. Zamira was a wonderful and kind hostess, and we couldn’t have asked for more. Breathtaking views from the hotel, delicious breakfast, and some great restaurants in walking distance. Would 100% go back and would highly recommend it to fellow travellers"
United Kingdom
Thomas
The price is £55
includes taxes & fees
19 Oct - 20 Oct
Antica Dimora Leones
A view from a window overlooking a rural landscape with fields and a distant mountain range.

17. B&B Palazzo Tortoli

B&B Palazzo Tortoli
San Gimignano City Centre
9.2 out of 10, Wonderful, (66 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 £111
includes taxes & fees
19 Oct - 20 Oct
B&B Palazzo Tortoli
Holiday Home Swimming Pool

18. Apartment in Castelfiorentino with Pool

Apartment in Castelfiorentino with Pool
Castelfiorentino (FI)
9.6 out of 10, Exceptional, (14 reviews)
"An easy walk through beautiful surroundings leads you right into town or to places nearby."
United States
Anonymous traveller
Apartment in Castelfiorentino with Pool
An aerial view of a hotel with a swimming pool, outdoor seating area, and well-maintained gardens.

19. Antica Pieve B&B

Antica Pieve B&B
Tavarnelle Val di Pesa
9.4 out of 10, Exceptional, (15 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 £126
includes taxes & fees
27 Oct - 28 Oct
Antica Pieve B&B
An outdoor dining area with tables and chairs, covered by umbrellas, overlooking a scenic landscape.

20. B&B La Fonte del Machiavelli

B&B La Fonte del Machiavelli
San Casciano in Val di Pesa
9.2 out of 10, Wonderful, (90 reviews)
"Beautiful location, beautiful rooms. Host is very friendly and accommodating."
Australia
James
The price is £100
includes taxes & fees
4 Nov - 5 Nov
B&B La Fonte del Machiavelli
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 il Milione Agriturismo

Fattoria il Milione Agriturismo

10/10 Excellent
"A Wonderful Stay at the Primavera Apartment – Helpful Tips for Travelers We thoroughly enjoyed our stay at the Primavera apartment in Florence! The apartment was fully renovated, and we highly recommend it to other travelers. One of the biggest conveniences for us was being able to park our car right in front of the door, which made unloading and loading our luggage easy. The apartment has a fully stocked kitchen, including a mini fridge/freezer. One little tip for future guests: the dishes are stored in the cabinet to the left as you enter. We didn't discover them until the night we were leaving, but fortunately, we didn't need them during our stay! Dining Recommendation We also had a wonderful surprise at the restaurant on the property. The authentic Italian vintage decor created a lovely atmosphere, and both the food and service were excellent. It was well worth the drive! A helpful tip: I recommend driving to the restaurant rather than walking, particularly at night. The restaurant is about a five-minute drive from the apartment, up a winding, rocky mountain road. After arriving, park behind the building where you will see the letter “P.” Then walk around to the front entrance, where you will be rewarded with a beautiful view of the city. We reserved the first seating at 7:30 p.m. The restaurant is closed on Mondays and serves dinner Tuesday through Sunday. Lunch is also available on Saturdays, Sundays, and holidays. If your schedule allows, I recommend visiting durin"
Carmen 3-night trip
Posted 10 hours ago
Fattoria il Milione Agriturismo

Find out more about Villa del Monte

Everything you need to know about Villa del Monte holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Villa del Monte holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Villa del Monte holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Villa del Monte holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Villa del Monte. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Villa del Monte holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Villa del Monte holiday rentals we have selected for you start as low as £37 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Villa del Monte rentals

At Expedia, we put the best Villa del Monte holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Villa del Monte rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Villa del Monte holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Villa del Monte. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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 are some of the best holiday rentals that Villa del Monte has to offer?

Villa with large garden in the Chianti hills: This holiday home rental outside of Villa del Monte is located in a rural location, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of books.

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 Sentierelsa Trail. 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.