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Villa del Monte Vacation Rentals

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Check prices for these dates

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

Our top choices for Villa del Monte vacation rentals

A view through a window of a stone staircase leading to a building with arched windows and a tower, overlooking a hilly landscape.

1. 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 ￥21,095
￥23,556 total
includes taxes & fees
Nov 3 - Nov 4
Palazzo Pacini
A stone-walled room with a wooden desk, a chair, a TV, and a large window with curtains.

2. 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 ￥15,556
￥17,639 total
includes taxes & fees
Nov 1 - Nov 2
Tenuta Sant'Ilario
A bathroom with a glass shower enclosure, a sink with a mirror above, and a pair of slippers on the floor.

3. Villa San Filippo

Villa San Filippo
4.0 star property
Barberino Val d'Elsa
8.6 out of 10, Excellent, (57 reviews)
"This place was beautiful, quiet like a picture you’d see in the movies"
Canada
Nadia
The price is ￥15,417
￥18,015 total
includes taxes & fees
Oct 30 - Oct 31
Villa San Filippo
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 ￥13,703
￥15,953 total
includes taxes & fees
Nov 2 - Nov 3
Casa Vacanze Le Case
A view from a window overlooking a rural landscape with fields and a distant mountain range.

5. B&B Palazzo Tortoli

B&B Palazzo Tortoli
San Gimignano City Centre
9.2 out of 10, Wonderful, (67 reviews)
"Francesco, our host, is so nice and welcoming. We had the beat stay and our room had the most fantastic view. Excellent breakfast, place was super clean and quiet. We highly recommend."
Canada
Caroline
The price is ￥18,410
￥21,130 total
includes taxes & fees
Nov 1 - Nov 2
B&B Palazzo Tortoli
A historic stone building with a prominent tower, arched windows, and a tiled roof.

6. 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 ￥16,542
￥19,075 total
includes taxes & fees
Nov 3 - Nov 4
Materia Rooms San Gimignano
A courtyard with brick flooring, outdoor tables with umbrellas, and a brick fountain.

7. Borgo Antico Residence

Borgo Antico Residence
Certaldo Alto
9.6 out of 10, Exceptional, (5 reviews)
"Great place to relax take in the local culture and enjoy Tuscany."
United States
jane
The price is ￥10,010
￥15,933 total
includes taxes & fees
Nov 9 - Nov 10
Borgo Antico Residence
A large outdoor swimming pool surrounded by lounge chairs and umbrellas, with a scenic view of hills and a cloudy sky.

8. 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 ￥20,138
￥22,678 total
includes taxes & fees
Oct 30 - Oct 31
Tenuta Quadrifoglio
A garden with a stone pathway, wooden benches, and various potted plants.

9. Antico Borgo il Cardino

Antico Borgo il Cardino
San Gimignano
9.4 out of 10, Exceptional, (88 reviews)
"friendly staff, gorgeous property"
United States
Heidi
The price is ￥21,254
￥24,258 total
includes taxes & fees
Oct 30 - Oct 31
Antico Borgo il Cardino
An aerial view of a hotel with a swimming pool, outdoor seating area, and well-maintained gardens.

10. 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
Antica Pieve B&B
A building with a wooden door, windows with shutters, and flower boxes.

11. 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 ￥11,996
￥14,076 total
includes taxes & fees
Nov 29 - Nov 30
Donna Nobile
A white mobile home with blue shutters, a red roof, and a small deck with white chairs.

12. 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 traveler
The price is ￥8,349
￥9,712 total
includes taxes & fees
Oct 30 - Oct 31
Camping Boschetto Di Piemma
A table with breakfast items and a view of rolling hills.

13. Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Tavarnelle Val di Pesa
8.6 out of 10, Excellent, (121 reviews)
"Superb property. Nice and quiet atmosphere. We enjoyed a lot. Definitely will come again."
United States
Nirav
The price is ￥12,142
￥13,708 total
includes taxes & fees
Nov 9 - Nov 10
Chianti Village Morrocco
An open wooden door leading to an outdoor patio with a table and chairs.

14. 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 ￥13,427
￥20,044 total
includes taxes & fees
Nov 2 - Nov 3
Palazzo al Torrione 2
A hallway with a wooden barrel, a white bench, a painting of a landscape, and a small table with a vase.

15. Sportland

Sportland
Colle di Val d'Elsa
7.2 out of 10, Good, (5 reviews)
"Struttura essenziale ed economica "
Italy
Giorgio
The price is ￥7,573
￥8,683 total
includes taxes & fees
Nov 1 - Nov 2
Sportland
A bedroom with a large bed, two ottomans, a chandelier, and a view through an arched doorway to a dining area.

16. 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 ￥13,992
￥15,919 total
includes taxes & fees
Nov 1 - Nov 2
Borgo San Giusto
An outdoor dining area with tables and chairs, covered by umbrellas, overlooking a scenic landscape.

17. B&B La Fonte del Machiavelli

B&B La Fonte del Machiavelli
San Casciano in Val di Pesa
9.2 out of 10, Wonderful, (92 reviews)
"The view is unique. Perfect location for a romantic trip."
United States
Stella
The price is ￥18,219
￥20,744 total
includes taxes & fees
Oct 30 - Oct 31
B&B La Fonte del Machiavelli
An arched entrance with a lantern above, flanked by two potted plants.

18. Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (108 reviews)
"Food was amazing, we love how quiet and relaxing it was"
United States
Justyna
The price is ￥25,103
￥28,317 total
includes taxes & fees
Nov 23 - Nov 24
Villa il Fedino
Exterior

19. 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, (29 reviews)
"Me and my girlfriend really did enjoy this property. Both host were very friendly and welcoming to us. We both did enjoy the feel at Home environment. We would definitely come back here on a future trip. Big shout out to the host for the wonderful cook meals. Great to know a bit about them as well."
United States
Erick
The price is ￥14,350
￥16,488 total
includes taxes & fees
Nov 4 - Nov 5
B&B Le Dimore di Mezza Costa - Home Restaurant & Cooking Classes
A patio with wicker furniture and potted plants, overlooking a scenic landscape.

20. Affittacamere Le Ginestre

Affittacamere Le Ginestre
San Gimignano City Centre
7.8 out of 10, Good, (6 reviews)
"Spacious. Clean. Quite. Air conditioned. Comfort. The View. The best. "
United States
Jorge
The price is ￥14,721
￥17,072 total
includes taxes & fees
Nov 7 - Nov 8
Affittacamere Le Ginestre
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

Hotel Borgo di Cortefreda Relais - Place of Charme

Hotel Borgo di Cortefreda Relais - Place of Charme

8/10 Good
"It was a beautiful place. Location was perfect to travel around. It was very clean. Restaurant is decent and food was good. Breakfast was ok."
Rahul 1-night trip
Posted 1 day ago
Hotel Borgo di Cortefreda Relais - Place of Charme

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 vacation rentals in Villa del Monte?

Yes, we have vacation rentals close to well known sights in Villa del Monte, or you can select a secluded option if you're looking for relaxation.

What's the top vacation rental in Villa del Monte?

Villa with large garden in the Chianti hills: Visitors like this Villa del Monte vacation home rental. It is located in a rural location and has an outdoor pool, a fireplace, and a barbecue grill 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 you can cook with friends or family. You can relax into your vacation 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 larger area.

What are vacation rentals like in Villa del Monte?

Vacation rentals are privately owned accommodations you can stay in for several days or longer in Villa del Monte. Vacation rentals offer extras such as WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of seclusion away from shared hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental a great choice for small groups.