Search Vacation Homes in Montegrossi

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
13 Jun - 15 Jun
In two weeks
20 Jun - 22 Jun
In one month
4 Jul - 6 Jul
In two months
1 Aug - 3 Aug

Compare 1089 Vacation Homes in Montegrossi with updated reviews, rates, and availability.

Borgo Argiano
Terrace/patio

Borgo Argiano

10.0 out of 10, Exceptional, (65)
"Very comfortable stay. "
Borgo Argiano
Luxury vacation home with fantastic views, pool, 4 bedrooms, 2 bathrooms
Outdoor pool

Luxury vacation home with fantastic views, pool, 4 bedrooms, 2 bathrooms

9.8 out of 10, Exceptional, (76)
"Perfect location for a family reunion with our adult children and their partners. We had a wonderful time."
Luxury vacation home with fantastic views, pool, 4 bedrooms, 2 bathrooms
Romantic house in the middle of the Chianti vineyards in the heart of Tuscany.
Interior

Romantic house in the middle of the Chianti vineyards in the heart of Tuscany.

8.8 out of 10, Excellent, (19)
"The legendary beauty of Tuscany is on full display. Rolling hills full of grapevines and olive trees as far as the eye can see. Very remote but also very beautiful. The villa has plenty of charm and space. Small issues due to the age of the place: unstable hot water and heating, awkward kitchen. But these are minor. We were lucky to be there at harvest time and local wineries were a real treat. "
Romantic house in the middle of the Chianti vineyards in the heart of Tuscany.
Wonderful Tuscan farmhouse with large spaces and panoramic views
2 bedrooms, internet, bed sheets

Wonderful Tuscan farmhouse with large spaces and panoramic views

9.8 out of 10, Exceptional, (17)
"We had a great time. The vila was everything we expected and our host was very accessible. I would highly recommend."
Wonderful Tuscan farmhouse with large spaces and panoramic views
Spacious Villa with Pool in the heart of Chianti, ideal for exploring Tuscany
Property grounds

Spacious Villa with Pool in the heart of Chianti, ideal for exploring Tuscany

9.6 out of 10, Exceptional, (47)
"A fantastic place to visit Tuscany from. The pool is great and the owners are very friendly."
Spacious Villa with Pool in the heart of Chianti, ideal for exploring Tuscany
The Porchereccia delle Bartaline
Exterior

The Porchereccia delle Bartaline

9.4 out of 10, Exceptional, (14)
"Great place and being in person is better than the on-line pictures. Beautiful views over looking the valley and vineyards below. Centrally located for plenty of great roadtrips. Enjoy!"
The Porchereccia delle Bartaline
House in a typical village in the heart of Chianti
Pool

House in a typical village in the heart of Chianti

9.6 out of 10, Exceptional, (69)
"great stay in the heart of Tuscany surrounded by vineyards and olive trees"
House in a typical village in the heart of Chianti
Villa Le Tortore Tuscany private luxury pool relax
Pool

Villa Le Tortore Tuscany private luxury pool relax

10.0 out of 10, Exceptional, (88)
"Loved our 10 days staying here couldn’t fault anything! Amazing location, would love to return."
Villa Le Tortore Tuscany private luxury pool relax
Charming apartment in the Historic Center of Siena
TV, books

Charming apartment in the Historic Center of Siena

10.0 out of 10, Exceptional, (16)
"Excellent!"
Charming apartment in the Historic Center of Siena
GIULIA -1 Bedroom Country House in Monteriggioni - Siena
Outdoor dining

GIULIA -1 Bedroom Country House in Monteriggioni - Siena

10.0 out of 10, Exceptional, (2)
"Ha sido una estancia maravillosa. El lugar estupendo. =)"
GIULIA -1 Bedroom Country House in Monteriggioni - Siena
Farmhouse in the heart of the real chiantishire
Exterior

Farmhouse in the heart of the real chiantishire

10.0 out of 10, Exceptional, (137)
"The house was beautiful and the location was wonderfully quiet and set back from the main road. It’s quaint and cozy. There’s a short gravel road up to the cottage but it’s an easy drive. I would definitely book again."
Farmhouse in the heart of the real chiantishire
Independent house in the hills of the Sienese countryside
Exterior

Independent house in the hills of the Sienese countryside

10.0 out of 10, Exceptional, (75)
"Lovely place to stay with Lovely hosts. Stunning views, beautiful house, lots of things to do within an easy drive."
Independent house in the hills of the Sienese countryside
Legnaia countryside luxury property, shared pool, ideal base to discover Tuscany
Outdoor dining

Legnaia countryside luxury property, shared pool, ideal base to discover Tuscany

10.0 out of 10, Exceptional, (11)
"Had a great time visiting the area. The home is beautiful. "
Legnaia countryside luxury property, shared pool, ideal base to discover Tuscany
Apartment House with garden Tuscany Chianti , Florence 15km.
Pool

Apartment House with garden Tuscany Chianti , Florence 15km.

9.8 out of 10, Exceptional, (72)
"Great property, well equipped, nice views, well maintained, very friendly and helpful host. We did really enjoy our stay :-)"
Apartment House with garden Tuscany Chianti , Florence 15km.
CASA SOLEALTO - Cozy apartment in the countryside near Florence Arezzo and Siena
Property grounds

CASA SOLEALTO - Cozy apartment in the countryside near Florence Arezzo and Siena

9.8 out of 10, Exceptional, (48)
"Elegant and high standard place, with a very friendly welcoming owner."
CASA SOLEALTO - Cozy apartment in the countryside near Florence Arezzo and Siena
Villa with large garden in the Chianti hills
Outdoor dining

Villa with large garden in the Chianti hills

9.4 out of 10, Exceptional, (70)
"Our group enjoyed staying in this location. It was comfortable and a perfect central location for exploring Tuscany."
Villa with large garden in the Chianti hills
12km North of Siena with a stunning view pool & tenniscourt 3 bedrooms ensuite
Outdoor pool, a heated pool

12km North of Siena with a stunning view pool & tenniscourt 3 bedrooms ensuite

10.0 out of 10, Exceptional, (22)
"Lovely place"
12km North of Siena with a stunning view pool & tenniscourt 3 bedrooms ensuite
Domus Nannini SPA - Palazzo Nannini - Loggia Salimbeni
Interior

Domus Nannini SPA - Palazzo Nannini - Loggia Salimbeni

10.0 out of 10, Exceptional, (17)
"The apartment is very large, beautifully decorated, and is in a fantastic location in Siena. Couldn't be better..... Gianluca was the perfect host. We were very happy!!! Will rent again for sure!!!"
Domus Nannini SPA - Palazzo Nannini - Loggia Salimbeni
Leo&Kira House
3 bedrooms, WiFi

Leo&Kira House

10.0 out of 10, Exceptional, (1)
"This beautiful old house in Greve is very charming and true to Italian style, made of stones. The downstairs room is a combination of bedroom and living with a TV, with access to the yard. There is bathroom downstairs. Upstairs has two connected rooms with queen size beds un each and one bathroom. Downstairs there's a good size kitchen with a fridge, stove, and a table. My only issue with the place was that there were no screens on the windows so when you opened them sometimes you'd get flies...
Leo&Kira House
Casa l'Oca, a spacious and bright house in the heart of Tuscany, in the Chianti area.

Casa l'Oca, a spacious and bright house in the heart of Tuscany, in the Chianti area.

9.0 out of 10, Wonderful, (11)
"The house has lots of space. We liked the area around and specially Home Restaurant near by the house "
Casa l'Oca, a spacious and bright house in the heart of Tuscany, in the Chianti area.
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free