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Check prices for these dates

In two weeks
27 Mar - 29 Mar
In two months
8 May - 10 May
In three months
5 Jun - 7 Jun
In four months
3 Jul - 5 Jul

Our top choices for Villa del Monte holiday rentals

2 outdoor pools, pool umbrellas, pool loungers

Villa in Lajatico

La Lunaria di Lajatico
The price is 3.360.251 ₫
5.556.913 ₫ total
includes taxes & fees
1 Apr - 2 Apr
La Lunaria di Lajatico
Deluxe Apartment, 1 Bedroom | Minibar, in-room safe, laptop workspace, soundproofing

Townhouse in Empoli

Borgo San Giusto
9.4 out of 10, Exceptional, (39 reviews)
"Lovely location and excellent staff. Restaurant on site is amazing! "
United Kingdom
Paul
The price is 2.357.007 ₫
2.682.619 ₫ total
includes taxes & fees
1 Apr - 2 Apr
Borgo San Giusto
La casa di Jakin | Terrace/patio

Residence in Casole d'Elsa

Tenuta Cantona
Tenuta Cantona
Outdoor pool

Condo resort in Terricciola

Laqua Vineyard
10.0 out of 10, Exceptional, (12 reviews)
"simply quiet and stunning"
United States
ivar
The price is 6.077.081 ₫
6.684.789 ₫ total
includes taxes & fees
1 Apr - 2 Apr
Laqua Vineyard
Exterior detail

Aparthotel in San Gimignano City Centre

La Casa di Ines
9.6 out of 10, Exceptional, (8 reviews)
"Love this town. Location is great "
United States
William
The price is 1.988.961 ₫
2.337.908 ₫ total
includes taxes & fees
15 Mar - 16 Mar
La Casa di Ines
Seasonal outdoor pool, open 9:00 AM to 8:00 PM, pool umbrellas

Residence in Florence

Fattoria il Milione Agriturismo
4.0 star property
8.4 out of 10, Very good, (233 reviews)
"We stayed two days with kids. Perfect resort feeling, enjoyed sun rising, perfect ample amount of healthy and fresh breakfast, very welcoming and friendly helpful staff, room are spacious and clean, and cozy remote control heating options, washrooms are very clean and water is always hot. "
Canada
Manjeet
The price is 1.908.325 ₫
2.519.301 ₫ total
includes taxes & fees
15 Mar - 16 Mar
Fattoria il Milione Agriturismo
Garden

Townhouse in Palaia

Antica Dimora Leones
9.0 out of 10, Wonderful, (16 reviews)
"Wonderful and unique place to stay. Staff were terrific. The church bells ring through the night so bring earplugs if you’re a light sleeper!"
Canada
Brendan
Antica Dimora Leones
Property entrance

Townhouse in San Casciano in Val di Pesa

Villa il Fedino
9.6 out of 10, Exceptional, (100 reviews)
"This is a lovely gem. Includes parking which is hard to find. Family owned and its a truly beautiful place. Breakfast was amazing as well!! Recommend!! "
United States
rose
The price is 3.994.095 ₫
4.513.546 ₫ total
includes taxes & fees
15 Mar - 16 Mar
Villa il Fedino
Restaurant

Residence in Impruneta

Relais Villa Olmo
9.4 out of 10, Exceptional, (229 reviews)
"Wonderful stay- we really enjoyed our stay and did not want to leave!! Beautiful hotel and wonderful service!"
United States
Cameron
Relais Villa Olmo
Reception

Townhouse in Colle di Val d'Elsa

Sportland
7.2 out of 10, Good, (5 reviews)
"Struttura essenziale ed economica "
Italy
Giorgio
Sportland
Outdoor dining

Townhouse in San Casciano in Val di Pesa

B&B La Fonte del Machiavelli
9.2 out of 10, Wonderful, (82 reviews)
"It was a wonderful stay the bed was comfortable and the view was beautiful. "
United States
Ruben
The price is 3.110.156 ₫
3.541.212 ₫ total
includes taxes & fees
15 Mar - 16 Mar
B&B La Fonte del Machiavelli
View from room

Residence in Barberino Tavarnelle

Chianti Village Morrocco
3.0 star property
8.6 out of 10, Excellent, (112 reviews)
"Front desk was very helpful and very comfortable room. "
United States
Chris
Chianti Village Morrocco
Exterior

Townhouse in San Casciano in Val di Pesa

B&B Le Dimore di Mezza Costa - Home Restaurant & Cooking Classes
9.4 out of 10, Exceptional, (25 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
The price is 2.253.772 ₫
2.599.191 ₫ total
includes taxes & fees
22 Mar - 23 Mar
B&B Le Dimore di Mezza Costa - Home Restaurant & Cooking Classes
Food court

Residence in Monteriggioni

Antico Borgo Poggiarello
2.0 star property
9.0 out of 10, Wonderful, (20 reviews)
"We had an absolutely wonderful time staying here. Our kids had fun on their playground and my wife and I enjoyed the views, the hospitality. And the entire experience. The food was outstanding. "
United States
James Bakley
The price is 6.629.543 ₫
7.382.528 ₫ total
includes taxes & fees
27 Mar - 28 Mar
Antico Borgo Poggiarello
Triple Room | Room service – dining

Townhouse in Montopoli in Val d'Arno

B&B Il Moscondoro
8.0 out of 10, Very good, (8 reviews)
"B&b nella campagna toscana, esperienza piacevole, il plus è il silezio totale che ha accompagnato il mio sonno"
Italy
Davide
The price is 2.455.386 ₫
2.700.925 ₫ total
includes taxes & fees
15 Mar - 16 Mar
B&B Il Moscondoro
Free daily buffet breakfast

Townhouse in Greve in Chianti

Terre di Baccio
9.8 out of 10, Exceptional, (72 reviews)
"The stay was great, and the staff were wonderful. "
United States
SYDNEY
Terre di Baccio
Studio, Patio, Ground Floor | Terrace/patio

Cottage in Siena

Fullino Nero
9.6 out of 10, Exceptional, (50 reviews)
"Great stay! Clean rooms with air conditioning. Beautiful grounds "
United States
Christian
The price is 2.820.966 ₫
3.223.103 ₫ total
includes taxes & fees
15 Mar - 16 Mar
Fullino Nero
Apartment, Patio | Living area | Flat-screen TV

Apartment in Chianni

La Ripadoro
The price is 3.192.002 ₫
4.411.510 ₫ total
includes taxes & fees
15 Mar - 16 Mar
La Ripadoro
Breakfast, lunch, dinner served; garden views

Townhouse in Florence

Marignolle Relais and Charme
9.2 out of 10, Wonderful, (91 reviews)
"I stayed here June 2025 and was most delighted in the property and staff. They were incredibly kind and accommodating and the property is beautiful. Would stay here again!"
Canada
Shelley
Marignolle Relais and Charme
Exterior detail

Residence in Signa

appartamenti la piazzetta
9.6 out of 10, Exceptional, (4 reviews)
"Oui"
France
Teresa
The price is 1.306.171 ₫
3.657.549 ₫ total
includes taxes & fees
15 Mar - 16 Mar
appartamenti la piazzetta
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

Borgo Del Cabreo

Borgo Del Cabreo

10/10 Excellent
"Borgo del Cabreo was our favorite place we stayed on our trip to Italy in March. Every detail of the Borgo was thoughtfully curated and is situated in the most beautiful setting in the Chianti region. The rooms and bathrooms were big. The king size bed was very comfortable. The breakfast was delicious in the most idyllic setting. The city center of Florence was loud at night even in March, so coming here was very restorative to my soul. The sounds of nature, birds singing, the idyllic scenary, was a wonderful contrast to Florence. We had the most wonderful dinner and wine at their sister property Pietra del Cabreo. My kids and I would return to Italy just to stay here again. "
Melissa 1-night trip
Posted 2 days ago
Borgo Del Cabreo

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.