Villa del Monte Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

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
$112 nightly
The price is $125
Dec 6 - Dec 7
Total with taxes and fees
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, (39 reviews)
"Great place, difficult driving access but enjoyable"
United States
Sergio
$125 nightly
The price is $141
Nov 6 - Nov 7
Total with taxes and fees
Tenuta Sant'Ilario
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, (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
$91 nightly
The price is $106
Dec 1 - Dec 2
Total with taxes and fees
B&B Palazzo Tortoli
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
$82 nightly
The price is $96
Nov 13 - Nov 14
Total with taxes and fees
Casa Vacanze Le Case
A large outdoor swimming pool surrounded by lounge chairs and umbrellas, with a scenic view of hills and a cloudy sky.

5. 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
$128 nightly
The price is $145
Nov 10 - Nov 11
Total with taxes and fees
Tenuta Quadrifoglio
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
$98 nightly
The price is $114
Nov 11 - Nov 12
Total with taxes and fees
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
$89 nightly
The price is $102
Nov 12 - Nov 13
Total with taxes and fees
Borgo Antico Residence
A building with a wooden door, windows with shutters, and flower boxes.

8. 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
$79 nightly
The price is $93
Nov 13 - Nov 14
Total with taxes and fees
Donna Nobile
A bedroom with a large bed, two ottomans, a chandelier, and a view through an arched doorway to a dining area.

9. 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
$84 nightly
The price is $96
Dec 6 - Dec 7
Total with taxes and fees
Borgo San Giusto
A table with breakfast items and a view of rolling hills.

10. Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Tavarnelle Val di Pesa
8.6 out of 10, Excellent, (122 reviews)
"Superb property. Nice and quiet atmosphere. We enjoyed a lot. Definitely will come again."
United States
Nirav
$72 nightly
The price is $81
Dec 6 - Dec 7
Total with taxes and fees
Chianti Village Morrocco
An aerial view of a hotel with a swimming pool, outdoor seating area, and well-maintained gardens.

11. 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
$107 nightly
The price is $122
Dec 1 - Dec 2
Total with taxes and fees
Antica Pieve B&B
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)
"Very friendly host 🙌 and great location"
Denmark
Klaus
$111 nightly
The price is $128
Nov 28 - Nov 29
Total with taxes and fees
Palazzo al Torrione 2
An arched entrance with a lantern above, flanked by two potted plants.

13. Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (109 reviews)
"Food was amazing, we love how quiet and relaxing it was"
United States
Justyna
$160 nightly
The price is $180
Nov 28 - Nov 29
Total with taxes and fees
Villa il Fedino
Exterior

14. 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
$89 nightly
The price is $102
Dec 1 - Dec 2
Total with taxes and fees
B&B Le Dimore di Mezza Costa - Home Restaurant & Cooking Classes
An outdoor dining area with tables and chairs, covered by umbrellas, overlooking a scenic landscape.

15. B&B La Fonte del Machiavelli

B&B La Fonte del Machiavelli
San Casciano in Val di Pesa
9.2 out of 10, Wonderful, (94 reviews)
"The view is unique. Perfect location for a romantic trip."
United States
Stella
$116 nightly
The price is $132
Nov 9 - Nov 10
Total with taxes and fees
B&B La Fonte del Machiavelli
A modern bathroom with a large round mirror, a vessel sink, a toilet, and a glass-enclosed shower.

16. Palazzo Brunelleschi

Palazzo Brunelleschi
Castelfiorentino
$110 nightly
The price is $123
Nov 17 - Nov 18
Total with taxes and fees
Palazzo Brunelleschi
A patio with wicker furniture and potted plants, overlooking a scenic landscape.

17. 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
$98 nightly
The price is $114
Nov 11 - Nov 12
Total with taxes and fees
Affittacamere Le Ginestre
A hallway with a wooden barrel, a white bench, a painting of a landscape, and a small table with a vase.

18. Sportland

Sportland
Colle di Val d'Elsa
7.2 out of 10, Good, (5 reviews)
"Struttura essenziale ed economica "
Italy
Giorgio
$48 nightly
The price is $55
Dec 1 - Dec 2
Total with taxes and fees
Sportland
A bedroom with a stone wall, a large mirror, a bed with white linens, a potted plant, and a view through a window with curtains.

19. Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (82 reviews)
"Amazing property and room, only issue is it’s very understaffed so it’s hard to get anything without chasing down workers. They also don’t stay on the property so after like 11pm you’re on your own. Besides that it was a wonderful location and very peaceful."
United States
Gage
$260 nightly
The price is $290
Nov 14 - Nov 15
Total with taxes and fees
Terre di Baccio
A bedroom with a bed, a window with curtains, a radiator, a bedside table with a plant, and a bathroom visible through an open door.

20. Affittacamere a 20 minuti da Firenze

Affittacamere a 20 minuti da Firenze
Empoli
8.4 out of 10, Very good, (26 reviews)
"Great location between Florence and Pisa. Also only a 5 minute walk to the train station that will take you to both cities. Great place to stay if looking for something quite and away from the crowds."
United States
Joshua
$77 nightly
The price is $88
Dec 1 - Dec 2
Total with taxes and fees
Affittacamere a 20 minuti da Firenze
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

A pool area with lounge chairs and umbrellas, surrounded by greenery and buildings.
Hotel Sovestro

Hotel Sovestro

Hotel Sovestro
San Gimignano

10/10 Excellent

Wonderful place to stay if you have a car.
United States
Mikhail
Reviewed October 1, 2014
Hotel Sovestro

Find out more about Villa del Monte

Everything you need to know about Villa del Monte vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Villa del Monte vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Villa del Monte vacation 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 low season months. For more hustle and bustle, you may prefer to visit Villa del Monte in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $55 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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 vacation 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 vacation.

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 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.

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