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Villa del Monte Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Villa del Monte vacation rentals

Deluxe Room, Patio | Frette Italian sheets, premium bedding, minibar, in-room safe

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
$103 nightly
The price is $117
Oct 21 - Oct 22
Total with taxes and fees
Tenuta Sant'Ilario
Front of property

2. 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
$92 nightly
The price is $104
Oct 11 - Oct 12
Total with taxes and fees
Borgo Antico Residence
Outdoor pool

3. 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
$121 nightly
The price is $139
Sep 25 - Sep 26
Total with taxes and fees
Casa Vacanze Le Case
Romantic Double Room, 1 Bedroom, Non Smoking | View from room

4. 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
$130 nightly
The price is $149
Oct 21 - Oct 22
Total with taxes and fees
B&B Palazzo Tortoli
Garden view

5. Villa San Filippo

Villa San Filippo
4.0 star property
Barberino Val d'Elsa
8.6 out of 10, Excellent, (53 reviews)
"This place was beautiful, quiet like a picture you’d see in the movies"
Canada
Nadia
$102 nightly
The price is $119
Sep 28 - Sep 29
Total with taxes and fees
Villa San Filippo
Balcony

6. Palazzo al Torrione 2

Palazzo al Torrione 2
San Gimignano City Centre
9.2 out of 10, Wonderful, (113 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
$134 nightly
The price is $153
Oct 22 - Oct 23
Total with taxes and fees
Palazzo al Torrione 2
Terrace/patio

7. Apartment 'Sasso 3' with Private Terrace, Wi-Fi and Air Conditioning

Apartment 'Sasso 3' with Private Terrace, Wi-Fi and Air Conditioning
San Gimignano
10.0 out of 10, Exceptional, (7 reviews)
"Pros: Everything was fine and clean. We enjoyed everything Cons: Nothing"
United States
Anonymous traveler
$209 nightly
The price is $215
Sep 22 - Sep 23
Total with taxes and fees
Apartment 'Sasso 3' with Private Terrace, Wi-Fi and Air Conditioning
Porch

8. 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
$87 nightly
The price is $101
Oct 4 - Oct 5
Total with taxes and fees
Donna Nobile
Superior Mobile Home | Terrace/patio

9. 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 traveler
$47 nightly
The price is $56
Sep 25 - Sep 26
Total with taxes and fees
Camping Boschetto Di Piemma
Property grounds

10. 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.
$193 nightly
The price is $199
Sep 29 - Sep 30
Total with taxes and fees
San Gimignano Apartment in the Heart of Town for 4 People with Fast Wi-Fi and Concierge Service
View from room

11. Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Tavarnelle Val di Pesa
8.6 out of 10, Excellent, (119 reviews)
"Front desk was very helpful and very comfortable room. "
United States
Chris
$74 nightly
The price is $83
Oct 15 - Oct 16
Total with taxes and fees
Chianti Village Morrocco
Exterior

12. 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
$140 nightly
The price is $159
Oct 21 - Oct 22
Total with taxes and fees
Antico Borgo il Cardino
Comfort Apartment, 1 Bedroom (Le Viole) | Terrace/patio

13. 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
$103 nightly
The price is $119
Oct 18 - Oct 19
Total with taxes and fees
Affittacamere Le Ginestre
Terrace/patio

14. Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.8 out of 10, Exceptional, (101 reviews)
"We love this beautiful exquisitely appointed hotel in a town with unexpected treasures and great food "
United Kingdom
John
$145 nightly
The price is $162
Oct 22 - Oct 23
Total with taxes and fees
Palazzo Pacini
View from property

15. 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
$146 nightly
The price is $165
Oct 10 - Oct 11
Total with taxes and fees
Antica Pieve B&B
Property grounds

16. Welcome "Casa San Gimi" your perfect base for exploring the wonders of Tuscany!

Welcome "Casa San Gimi" your perfect base for exploring the wonders of Tuscany!
San Gimignano City Centre
9.8 out of 10, Exceptional, (16 reviews)
"Beautiful home with all the amenities!! Excellent location and enjoyed walking this adorable town!! "
United States
William
$265 nightly
The price is $295
Sep 27 - Sep 28
Total with taxes and fees
Welcome "Casa San Gimi" your perfect base for exploring the wonders of Tuscany!
Deluxe Apartment, 1 Bedroom | Minibar, in-room safe, laptop workspace, soundproofing

17. Borgo San Giusto

Borgo San Giusto
Empoli
9.4 out of 10, Exceptional, (45 reviews)
"A lovely overnight stay here! Staff were so accommodating to our limited Italian and the children. Would recommend"
United Kingdom
Lucy
$104 nightly
The price is $118
Oct 11 - Oct 12
Total with taxes and fees
Borgo San Giusto
Garden

18. Antica Dimora Leones

Antica Dimora Leones
Palaia
9.2 out of 10, Wonderful, (18 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
$52 nightly
The price is $62
Oct 18 - Oct 19
Total with taxes and fees
Antica Dimora Leones
Outdoor dining

19. San Gimignano Apartment in the Heart of the City for 3 People: Fast Wi-Fi, Concierge Service

San Gimignano Apartment in the Heart of the City for 3 People: Fast Wi-Fi, Concierge Service
San Gimignano City Centre
9.8 out of 10, Exceptional, (12 reviews)
"Our cosy little part of the palazzo was wonderful and our host sent us to an amazing array of restaurants. We had a wonderful time."
United States
Daniel T.
$230 nightly
The price is $236
Sep 22 - Sep 23
Total with taxes and fees
San Gimignano Apartment in the Heart of the City for 3 People: Fast Wi-Fi, Concierge Service
Exterior

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
$104 nightly
The price is $119
Oct 21 - Oct 22
Total with taxes and fees
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

Relais Vignale & Spa

Relais Vignale & Spa

10/10 Excellent
"Beautiful small medieval town with castle and narrow streets. Close to wineries but not much else to do….location is very beautiful on top of hill."
mark 1-night trip
Posted 2 days ago
Relais Vignale & Spa

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 $52 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.

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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 Alta Val d'Elsa River Park. 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.