Holiday Rentals Villa del Monte from ฿1,892: Find Short-Term Rentals & Holiday Accommodations

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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

Gambassi Terme

Sergio

฿4,012 total

includes taxes & fees

1 Nov - 2 Nov

A white mobile home with blue shutters, a red roof, and a small deck with white chairs.

2. Camping Boschetto Di Piemma

San Gimignano

Anonymous traveller

฿2,079 total

includes taxes & fees

21 Oct - 22 Oct

A courtyard with brick flooring, outdoor tables with umbrellas, and a brick fountain.

3. Borgo Antico Residence

Certaldo Alto

jane

฿3,405 total

includes taxes & fees

25 Oct - 26 Oct

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

4. Villa San Filippo

Barberino Val d'Elsa

Nadia

฿3,322 total

includes taxes & fees

28 Oct - 29 Oct

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

5. Casa Vacanze Le Case

San Gimignano

Andrew

฿3,586 total

includes taxes & fees

2 Nov - 3 Nov

A table with breakfast items and a view of rolling hills.

6. Chianti Village Morrocco

Tavarnelle Val di Pesa

Winonah

฿3,015 total

includes taxes & fees

21 Oct - 22 Oct

A well-maintained garden with a central fountain, surrounded by lush greenery and flowering plants.

7. Tenuta Quadrifoglio

Gambassi Terme

Geraldine

฿4,846 total

includes taxes & fees

28 Oct - 29 Oct

A garden with a stone pathway, wooden benches, and various potted plants.

8. Antico Borgo il Cardino

San Gimignano

Craig

฿5,780 total

includes taxes & fees

21 Oct - 22 Oct

A garden with a round table and wicker chairs under a tree.

9. Antica Dimora Leones

Palaia

Thomas

฿2,349 total

includes taxes & fees

22 Oct - 23 Oct

A building with a wooden door, windows with shutters, and flower boxes.

10. Donna Nobile

San Gimignano City Centre

Treena

฿3,012 total

includes taxes & fees

1 Nov - 2 Nov

An open wooden door leading to an outdoor patio with a table and chairs.

11. Palazzo al Torrione 2

San Gimignano City Centre

Angel

฿4,509 total

includes taxes & fees

7 Nov - 8 Nov

A reception desk with the word "SPORTLAND" prominently displayed.

12. Sportland

Colle di Val d'Elsa

Giorgio

฿1,718 total

includes taxes & fees

25 Oct - 26 Oct

An outdoor dining area with tables and chairs, candles, and a view of palm trees and greenery.

13. Palazzo Pacini

Colle di Val d'Elsa

John

฿5,584 total

includes taxes & fees

30 Oct - 31 Oct

A bedroom with a large bed, two ottomans, a chandelier, and a view through an arched doorway to a dining area.

14. Borgo San Giusto

Empoli

Lucy

฿3,773 total

includes taxes & fees

1 Nov - 2 Nov

An aerial view of a hotel with a swimming pool, outdoor seating area, and well-maintained gardens.

15. Antica Pieve B&B

Tavarnelle Val di Pesa

Jessica

฿5,611 total

includes taxes & fees

21 Oct - 22 Oct

A view from a window overlooking a rural landscape with fields and a distant mountain range.

16. B&B Palazzo Tortoli

San Gimignano City Centre

Caroline

฿5,232 total

includes taxes & fees

21 Oct - 22 Oct

17. Toscana Vacanze

MONTAIONE

฿8,953 total

includes taxes & fees

2 Nov - 3 Nov

A narrow street with stone buildings, a tower, and an archway.

18. Materia Rooms San Gimignano

San Gimignano City Centre

Bradley

฿4,086 total

includes taxes & fees

3 Nov - 4 Nov

19. B&B Le Dimore di Mezza Costa - Home Restaurant & Cooking Classes

San Casciano in Val di Pesa

Erick

฿3,473 total

includes taxes & fees

27 Oct - 28 Oct

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Top Villa del Monte Hotel Reviews

Poderi Arcangelo

10/10 Excellent

"Personnels très gentils, dégustation de vins super bon et intéressant, souper excellent, très bonne qualité nourriture, vin, huile d’olive. Je recommande cet endroit fortement"

Fattoria di Vegi

10/10 Excellent

"We loved our stay here! It was the perfect place to slow down and take in the beauty of Tuscany. We enjoyed the cooking class and wine tasting we took with the other couples staying there. Highly recommend booking this as part of your stay! We also enjoyed the amenities they offered like the art room - we set up easels in the grass, drank wine, and drew each other’s portraits which ended up being pretty funny. The food at the restaurant was good although it felt like some of the dishes could’ve been simpler. Our favorite dishes was the pasta with mushrooms and the pizzas on pizza night. The majority of the staff was friendly too. Highly recommend this location if you’re looking for a beautifully designed, relaxing location with amenities/activities. We hope to be back!"

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"

Salvadonica - Borgo del Chianti

10/10 Excellent

"Beautiful property, clean and spacious room, great service. We are so thankful for our stay at this property. We had a patio outside our room, and this was a highlight for me. The restaurant had a bar with local wines and snacks; we could then sit outside and relax in peace. We did one of the wine tastings with the hotel, which was fabulous. We ate at the restaurant; my teenage children each found something they enjoyed. It is located outside of Florence, so we did have a bit of a drive each day to see different sites, but the property made the stay very well worth it. Breakfast each day was also really wonderful,"

Mormoraia

8/10 Good

"Great location close to San Gimignano for day trips Siena, volterra, etc. Beautiful views and very peaceful. Very clean and comfortable hotel, with gorgeous 360 views from rooms. Unfortunately it’s very expensive to use the amenities, so we didn’t use them. The staff are very nice and helpful. The restaurant was OK. The breakfast was good but not great (coffee was great though). We enjoyed their wine."

Hotel Casolare Le Terre Rosse

10/10 Excellent

"Great Family run hotel with friendly staff. Perfectly located to explore Tuscany.. we visited Sienna, Certaldo, Volterra, Sam Gimignano and Livorno on the coast. There is a walkable (5mins) winery called Il Colombaio which I would highly recommended. The breakfast buffet was fabulous."

Find out more about Villa del Monte

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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 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.

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Check prices for these dates

Our top choices for Villa del Monte holiday rentals

1. Tenuta Sant'Ilario

2. Camping Boschetto Di Piemma

3. Borgo Antico Residence

4. Villa San Filippo

5. Casa Vacanze Le Case

6. Chianti Village Morrocco

7. Tenuta Quadrifoglio

8. Antico Borgo il Cardino

9. Antica Dimora Leones

10. Donna Nobile

11. Palazzo al Torrione 2

12. Sportland

13. Palazzo Pacini

14. Borgo San Giusto

15. Antica Pieve B&B

16. B&B Palazzo Tortoli

17. Toscana Vacanze

18. Materia Rooms San Gimignano

19. B&B Le Dimore di Mezza Costa - Home Restaurant & Cooking Classes

Find holiday rentals that suit your style

Top Villa del Monte Hotel Reviews

Poderi Arcangelo

Fattoria di Vegi

Fattoria il Milione Agriturismo

Salvadonica - Borgo del Chianti

Mormoraia

Hotel Casolare Le Terre Rosse

La Cisterna

Borgo Vescine

Tenuta di Artimino Melia Collection

Find out more about Villa del Monte

Frequently asked questions

Go further with the Expedia app

Search Holiday Rentals in Villa del Monte

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Villa del Monte holiday rentals

1. Tenuta Sant'Ilario

2. Camping Boschetto Di Piemma

3. Borgo Antico Residence

4. Villa San Filippo

5. Casa Vacanze Le Case

6. Chianti Village Morrocco

7. Tenuta Quadrifoglio

8. Antico Borgo il Cardino

9. Antica Dimora Leones

10. Donna Nobile

11. Palazzo al Torrione 2

12. Sportland

13. Palazzo Pacini

14. Borgo San Giusto

15. Antica Pieve B&B

16. B&B Palazzo Tortoli

17. Toscana Vacanze

18. Materia Rooms San Gimignano

19. B&B Le Dimore di Mezza Costa - Home Restaurant & Cooking Classes

Find holiday rentals that suit your style

Top Villa del Monte Hotel Reviews

Poderi Arcangelo

Find out more about Villa del Monte

Frequently asked questions

Go further with the Expedia app