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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 balcony with a view of rolling hills, a table with a book and a bottle, and a chair.

1. 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
$98 nightly
The price is $114
Oct 30 - Oct 31
Total with taxes and fees
Villa San Filippo
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
$97 nightly
The price is $110
Nov 3 - Nov 4
Total with taxes and fees
Tenuta Sant'Ilario
A courtyard with brick flooring, outdoor tables with umbrellas, and a brick fountain.

3. 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 $101
Oct 30 - Oct 31
Total with taxes and fees
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
$87 nightly
The price is $101
Nov 6 - Nov 7
Total with taxes and fees
Casa Vacanze Le Case
A view through a window of a stone staircase leading to a building with arched windows and a tower, overlooking a hilly landscape.

5. 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
$134 nightly
The price is $149
Nov 1 - Nov 2
Total with taxes and fees
Palazzo Pacini
A white mobile home with blue shutters, a red roof, and a small deck with white chairs.

6. 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
$53 nightly
The price is $62
Oct 30 - Oct 31
Total with taxes and fees
Camping Boschetto Di Piemma
A view from a window overlooking a rural landscape with fields and a distant mountain range.

7. 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
$116 nightly
The price is $133
Nov 5 - Nov 6
Total with taxes and fees
B&B Palazzo Tortoli
A bedroom with a large bed, two ottomans, a chandelier, and a view through an arched doorway to a dining area.

8. 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
$88 nightly
The price is $100
Oct 30 - Oct 31
Total with taxes and fees
Borgo San Giusto
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
$132 nightly
The price is $151
Oct 30 - Oct 31
Total with taxes and fees
Antico Borgo il Cardino
A building with a wooden door, windows with shutters, and flower boxes.

10. 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
$76 nightly
The price is $89
Nov 29 - Nov 30
Total with taxes and fees
Donna Nobile
A table with breakfast items and a view of rolling hills.

11. 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
$76 nightly
The price is $86
Nov 3 - Nov 4
Total with taxes and fees
Chianti Village Morrocco
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
$111 nightly
The price is $127
Nov 2 - Nov 3
Total with taxes and fees
Palazzo al Torrione 2
A historic stone building with a prominent tower, arched windows, and a tiled roof.

13. 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
$104 nightly
The price is $120
Nov 29 - Nov 30
Total with taxes and fees
Materia Rooms San Gimignano
A narrow alleyway with brick walls, wooden barrels, and potted plants.

14. 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, (44 reviews)
"Beautiful location in San Gimignano! The owner was so attentive and provided great suggestions for our visit. Charming apartment that serviced all of are needs. Boboli bakery (25 yards from apartment) is amazing and a must! Enjoyable stay!"
United States
Curt G.
$168 nightly
The price is $174
Nov 1 - Nov 2
Total with taxes and fees
San Gimignano Apartment in the Heart of Town for 4 People with Fast Wi-Fi and Concierge Service
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, (93 reviews)
"The view is unique. Perfect location for a romantic trip."
United States
Stella
$115 nightly
The price is $131
Nov 16 - Nov 17
Total with taxes and fees
B&B La Fonte del Machiavelli
An arched entrance with a lantern above, flanked by two potted plants.

16. 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
$159 nightly
The price is $179
Nov 23 - Nov 24
Total with taxes and fees
Villa il Fedino
A courtyard with stone buildings, a grassy area, and a brick wall.

17. Toscana Vacanze

Toscana Vacanze
MONTAIONE
$234 nightly
The price is $261
Oct 30 - Oct 31
Total with taxes and fees
Toscana Vacanze
A vineyard with a stone building, a metal gate, and purple plants in the foreground.

18. 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, (17 reviews)
"Beautiful home with all the amenities!! Excellent location and enjoyed walking this adorable town!! "
United States
William
$257 nightly
The price is $286
Nov 1 - Nov 2
Total with taxes and fees
Welcome "Casa San Gimi" your perfect base for exploring the wonders of Tuscany!
A garden with a round table and wicker chairs under a tree.

19. 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
$60 nightly
The price is $71
Nov 1 - Nov 2
Total with taxes and fees
Antica Dimora Leones
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, (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
$86 nightly
The price is $100
Nov 5 - Nov 6
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

Castelfalfi

Castelfalfi

10/10 Excellent
"Get ready to be impressed if you stay here. Every staff member from our arrival to our departure genuinely greeted us and welcomed us and many remembered our name. They always asked if we needed anything or offered help or suggestions in a genuine “we want to help way”. The concierge before our stay was ultra responsive, during our stay they were always present. You want attention to detail, Castelfalfi has it covered. Drinks are carefully made and delivered. Turn down service straightened the room, put little clothes under anything we had on the bathroom sink or room table, a new bookmark was left next to my book on the nightstand, cords were always wrapped and made to look tidy, I could go on and on. The food in the various restaurants was amazing. The little meat and cheese shop made a tremendous& fresh sandwich sliced up right in front of us on fresh baked bread. The view of sunset from the back deck had many guests out watching for good reason. The spa pool was great and the gym was pretty big. The breakfast buffet had everything you could want. Want fresh honey? There was a station with a honeycomb taken from their property…it drips fresh honey into a tray that empties into a bowl for you. The wine tasting was fun and delicious and worth it. Everything is on site and you will not want to leave the property during your stay or at the end of your trip. Castelfalfi- I hope and pray I return some day, thank you!!"
Patrick 2-night trip
Posted 8 hours ago
Castelfalfi

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 $49 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 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.