Montegrossi Vacation Rentals

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Check prices for these dates

In two weeks
Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

Vacation Rentals in Montegrossi

Aerial view
Relais Villa Olmo

Residence in Impruneta

9.4 out of 10, Exceptional, (227)
"This is a beautiful Villa with a stunning views. Rooms were large and very clean and the location was wonderful. It was close to Florence and ideal for exploring Tuscany. Restaurant offered delicious buffet breakfast and many other wonderful local dishes for lunch and dinner. I would highly recommend this Villa and would love to stay here again."
United States
Ewa
Relais Villa Olmo
Lobby lounge
ApartHotel Anghel

Apartment in Siena

8.4 out of 10, Very Good, (334)
"Would recommend staying here and will hopefully be back!"
Canada
Lisa
The price is P4,082
P4,764 total
includes taxes & fees
Dec 10 - Dec 11
ApartHotel Anghel
View from room
Tuscasì Aparthotel

Aparthotel in Sovicille

9.2 out of 10, Wonderful, (25)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is P3,865
P5,144 total
includes taxes & fees
Dec 13 - Dec 14
Tuscasì Aparthotel
Bar (on property)
Il Battistero Siena - Residenza d'Epoca

Residence in Siena City Centre

9.6 out of 10, Exceptional, (191)
"Great location and friendly staff. "
United States
Parissa
Il Battistero Siena - Residenza d'Epoca
Outdoor pool, pool umbrellas, sun loungers
Chianti Village Morrocco

Residence in Barberino Tavarnelle

3.0 star property
8.6 out of 10, Excellent, (108)
"Front desk was very helpful and very comfortable room. "
United States
Chris
The price is P4,085
P4,631 total
includes taxes & fees
Dec 13 - Dec 14
Chianti Village Morrocco
Private kitchen
Regis Condo

Apartment in Siena City Centre

9.4 out of 10, Exceptional, (65)
"This was one of our favorite stays in Italy. It was spacious, clean, and in a great part of the city."
United States
Ben
Regis Condo
Outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas
Relais Villa Belvedere

Aparthotel in Figline e Incisa Valdarno

9.0 out of 10, Wonderful, (71)
"Very nice place"
United States
Maria
The price is P5,982
P6,683 total
includes taxes & fees
Dec 10 - Dec 11
Relais Villa Belvedere
View from room
Residenza d'Epoca Palazzo Borghesi

Residence in Siena City Centre

9.6 out of 10, Exceptional, (116)
"We enjoyed our stay here. Convenient, clean, central to city center, shops, and restaurants. We would stay here again."
United States
Linda
The price is P11,228
P12,625 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Residenza d'Epoca Palazzo Borghesi
Exterior
Camping Siena Colleverde

Camping in Scacciapensieri

3.0 star property
8.2 out of 10, Very Good, (159)
"Safe, great proximity to Siena without being too close, nice pool."
United States
Martha
Camping Siena Colleverde
Front of property - evening/night
Villa Il Palagio

Apartment in Rignano sull'Arno

8.6 out of 10, Excellent, (60)
"The best place in the region"
United Kingdom
Kamen
Villa Il Palagio
Premium bedding, Select Comfort beds, minibar, in-room safe
La Terrazza Sul Campo Rooming House

Residence in Siena City Centre

9.8 out of 10, Exceptional, (239)
"Huge room! Great location "
Canada
karen
La Terrazza Sul Campo Rooming House
Terrace/patio
Borgo Argiano

Vacation Home in Castelnuovo Berardenga

10.0 out of 10, Exceptional, (73)
"Borgo Argiano is a beautiful property, very well run by Dario and staff. We highly recommend staying there if you are interested in exploring the Tuscan region. The apartments are large and they stock the kitchen for convenience It is also a winery and you could get a tour was well as a tasting of the delicious wines."
United States
Aurora
Borgo Argiano
Seasonal outdoor pool, pool umbrellas, sun loungers
Castello Del Nero - Podere San Filippo

Residence in Barberino Tavarnelle

9.8 out of 10, Exceptional, (38)
"Much nicer stay then the rooms at the Como"
United States
Anonymous traveler
Castello Del Nero - Podere San Filippo
Outdoor pool, pool umbrellas, sun loungers
Riserva di Fizzano Residence

Residence in Castellina in Chianti

3.0 star property
9.8 out of 10, Exceptional, (24)
"Perfect location on the top of a hill surrounded by the beautiful vineyards of Chianti. Enjoy the view by the pool or the fabulous sunset with a glass of wine. The staff were friendly and the restaurant was 5 star. I highly recommend a stay to fulfill all your Tuscan dreams. "
United States
Eileen
Riserva di Fizzano Residence
Living area
Palazzo Lenzi

Apartment in Siena City Centre

9.0 out of 10, Wonderful, (2)
"Very very nice. Enjoyed our stay. Air conditioning did not work well so a bit hot. But overall very nice. "
United States
Daniel
The price is P13,567
P15,199 total
includes taxes & fees
Dec 10 - Dec 11
Palazzo Lenzi
Living area
Casa Ciseri

Apartment in Siena City Centre

9.8 out of 10, Exceptional, (9)
"Very nice stay!"
United States
Danielle
The price is P15,407
P17,223 total
includes taxes & fees
Dec 10 - Dec 11
Casa Ciseri
View from property
Relais Villa Belpoggio - Residenza d'Epoca

Residence in Loro Ciuffenna

9.8 out of 10, Exceptional, (35)
"Excellent getaway- beautiful property - great staff - extremely clean - I give it a 100"
United Kingdom
Mona
The price is P9,669
P10,635 total
includes taxes & fees
Dec 10 - Dec 11
Relais Villa Belpoggio - Residenza d'Epoca
Terrace/patio
Borgo Argenina

Aparthotel in Gaiole in Chianti

9.8 out of 10, Exceptional, (22)
"A planned Tuscany trip in the making for over a year. Saw this property came up while doing research and had a wonderful and romantic history. The property was even more beautiful than the pictures posted. It definitely caters to all types of travellers. A perfect bed and breakfast stay. Definitely recommend and will be back again. "
Canada
Nancy
Borgo Argenina
Seasonal outdoor pool, pool umbrellas, sun loungers
Villa San Filippo

Residence in Barberino Tavarnelle

4.0 star property
8.4 out of 10, Very Good, (40)
"Conveniently situated between Florence and Siena in the heart of the Chianti region with stunning views. Friendly relaxed hosts who provide a substantial breakfast. Beautiful large swimming pool to cool off at the end of the day."
United Kingdom
Andrew
Villa San Filippo
Property entrance
Palazzo Pacini

Residence in Colle di Val d'Elsa

9.8 out of 10, Exceptional, (98)
"Such a beautiful gem of a hotel. Steeped in Florentine style. Comfortable and classy. Definitely would recommend "
United States
George
Palazzo Pacini
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 Montegrossi Hotel Reviews

Hotel Athena

Hotel Athena

10/10 Excellent
"The hotel is in an excellent location. The room is extremely comfortable and has a beautiful view. All the staff are super friendly, helpful, and always smiling. The breakfast is varied, delicious, and amazing. I would definitely stay here again."
Natalia 1-night trip
Posted 4 days ago
Hotel Athena

Find out more about Montegrossi

Search for holiday rentals in Montegrossi on Expedia! You can easily find your home rentals, villas, holiday apartments in Montegrossi using one of the methods below:

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Frequently asked questions

Can I find a vacation rental in Montegrossi?

Yes, there are vacation rentals close to well known sights in Montegrossi, or you can select a more remote option if you want a relaxing place to stay.

What are some of the best vacation home rentals in Montegrossi?

Borgo Argiano: This vacation home rental outside of Montegrossi is located on a river and has a balcony, a terrace, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a coffee maker. You can relax into your vacation with a garden and a library.

What’s there to see and do in Montegrossi?

Explore the area and family-friendly sights such as Borgo di Vescine - Tenute di Castelvecchi, or get out into nature at a spot like Chianti Sculpture Park. Badia a Coltibuono and Le Miccine are a couple of places you'll find in the larger area.

What’s a vacation rental in Montegrossi like?

Vacation rentals are private properties you can stay in for short or long periods in Montegrossi. Vacation rentals offer extras such as patios, hot tubs, and fire pits so you'll feel just like you're at home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of seclusion away from shared hotel elevators and busy front desks while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for a small group gathering.