Villa del Monte Vacation Rentals

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Check prices for these dates

In two weeks
Apr 3 - Apr 5
In two months
May 15 - May 17
In three months
Jun 12 - Jun 14
In four months
Jul 10 - Jul 12

Our top choices for Villa del Monte vacation rentals

Outdoor pool

Laqua Vineyard

Laqua Vineyard
Terricciola
10.0 out of 10, Exceptional, (12 reviews)
"Love it here. Food was amazing as well! 2 bedroom apartment was perfect. "
United Kingdom
Eisaivan
The price is ￥35,821
￥39,403 total
includes taxes & fees
Apr 1 - Apr 2
Laqua Vineyard
Deluxe Apartment, 1 Bedroom | Minibar, in-room safe, laptop workspace, soundproofing

Borgo San Giusto

Borgo San Giusto
Empoli
9.4 out of 10, Exceptional, (39 reviews)
"Lovely location and excellent staff. Restaurant on site is amazing! "
United Kingdom
Paul
The price is ￥12,318
￥14,097 total
includes taxes & fees
Apr 1 - Apr 2
Borgo San Giusto
Apartment, Patio | Living area | Flat-screen TV

La Ripadoro

La Ripadoro
Chianni
The price is ￥23,209
￥31,001 total
includes taxes & fees
Mar 17 - Mar 18
La Ripadoro
La casa di Jakin | Terrace/patio

Tenuta Cantona

Tenuta Cantona
Casole d'Elsa
The price is ￥14,760
￥26,631 total
includes taxes & fees
Apr 1 - Apr 2
Tenuta Cantona
Free daily buffet breakfast

Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (72 reviews)
"The stay was great, and the staff were wonderful. "
United States
SYDNEY
Terre di Baccio
Property entrance

Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
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 ￥24,018
￥27,149 total
includes taxes & fees
Mar 17 - Mar 18
Villa il Fedino
2 outdoor pools, pool umbrellas, sun loungers

La Lunaria di Lajatico

La Lunaria di Lajatico
Lajatico
The price is ￥20,419
￥33,767 total
includes taxes & fees
Apr 1 - Apr 2
La Lunaria di Lajatico
Interior

Chianti Craft House Badia a Passignano

Chianti Craft House Badia a Passignano
Barberino Tavarnelle
9.8 out of 10, Exceptional, (10 reviews)
"Great food in the area. Beautiful church tour and a fantastic host for our stay!"
United States
Craig & Conny M.
The price is ￥27,081
￥38,387 total
includes taxes & fees
Mar 17 - Mar 18
Chianti Craft House Badia a Passignano
Exterior

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
9.4 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 ￥12,462
￥14,437 total
includes taxes & fees
Mar 24 - Mar 25
B&B Le Dimore di Mezza Costa - Home Restaurant & Cooking Classes
Reception

Sportland

Sportland
Colle di Val d'Elsa
7.2 out of 10, Good, (5 reviews)
"Struttura essenziale ed economica "
Italy
Giorgio
The price is ￥7,736
￥8,875 total
includes taxes & fees
Mar 22 - Mar 23
Sportland
Garden

Antica Dimora Leones

Antica Dimora Leones
Palaia
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
The price is ￥11,859
￥13,774 total
includes taxes & fees
Apr 6 - Apr 7
Antica Dimora Leones
Food court

Antico Borgo Poggiarello

Antico Borgo Poggiarello
2.0 star property
Monteriggioni
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 ￥40,285
￥44,860 total
includes taxes & fees
Mar 27 - Mar 28
Antico Borgo Poggiarello
Triple Room | Room service - dining

B&B Il Moscondoro

B&B Il Moscondoro
Montopoli in Val d'Arno
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 ￥14,323
￥15,755 total
includes taxes & fees
Mar 17 - Mar 18
B&B Il Moscondoro
View from room

Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Barberino Tavarnelle
8.6 out of 10, Excellent, (112 reviews)
"Front desk was very helpful and very comfortable room. "
United States
Chris
Chianti Village Morrocco
2 bedrooms, free WiFi, bed sheets

Tuscan House Relax in the heart of the Tuscan countryside

Tuscan House Relax in the heart of the Tuscan countryside
Montespertoli
The price is ￥18,054
￥21,883 total
includes taxes & fees
Mar 22 - Mar 23
Tuscan House Relax in the heart of the Tuscan countryside
Breakfast, lunch, dinner served; garden views

Marignolle Relais and Charme

Marignolle Relais and Charme
Florence
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
The price is ￥21,279
￥25,595 total
includes taxes & fees
Mar 18 - Mar 19
Marignolle Relais and Charme
Seasonal outdoor pool, open 9:00 AM to 8:00 PM, pool umbrellas

Fattoria il Milione Agriturismo

Fattoria il Milione Agriturismo
4.0 star property
Florence
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 ￥11,596
￥15,308 total
includes taxes & fees
Mar 17 - Mar 18
Fattoria il Milione Agriturismo
Property amenity

hu Firenze Certosa camping in town

hu Firenze Certosa camping in town
Impruneta
8.0 out of 10, Very Good, (59 reviews)
"Wonderful staff and great amenities!"
Canada
Chenjin
The price is ￥5,965
￥7,109 total
includes taxes & fees
Mar 17 - Mar 18
hu Firenze Certosa camping in town
Exterior detail

La Casa di Ines

La Casa di Ines
San Gimignano City Centre
9.6 out of 10, Exceptional, (8 reviews)
"Love this town. Location is great "
United States
William
The price is ￥13,296
￥15,537 total
includes taxes & fees
Mar 17 - Mar 18
La Casa di Ines
Restaurant

Relais Villa Olmo

Relais Villa Olmo
Impruneta
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
The price is ￥19,695
￥22,211 total
includes taxes & fees
Mar 30 - Mar 31
Relais Villa Olmo
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 4 days ago
Borgo Del Cabreo

Find out more about Villa del Monte

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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?

Poggio Puccino Countryhouse: 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 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a patio, a garden, and a selection of games so you can immerse yourself in your vacation.

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.