Montegrossi Vacation Rentals

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Check prices for these dates

In two weeks
19 Jun - 21 Jun
In two months
31 Jul - 2 Aug
In three months
28 Aug - 30 Aug
In four months
25 Sep - 27 Sep

Our top choices for Montegrossi vacation rentals

Seasonal outdoor pool, pool umbrellas, sun loungers

Villa San Filippo

Villa San Filippo
4.0 star property
Barberino Tavarnelle
8.6 out of 10, Excellent, (43 reviews)
"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
The price is AED 285
AED 340 total
includes taxes & fees
1 Jul - 2 Jul
Villa San Filippo
Premium bedding, down comforters, pillowtop beds, minibar

Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.2 out of 10, Wonderful, (27 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is AED 325
AED 413 total
includes taxes & fees
1 Jul - 2 Jul
Tuscasì Aparthotel
Lobby

Villa Cassia di Baccano

Villa Cassia di Baccano
Loro Ciuffenna
9.4 out of 10, Exceptional, (23 reviews)
"The staff were great and the villa was amazing"
United States
Ralphvincent
The price is AED 514
AED 565 total
includes taxes & fees
21 Jun - 22 Jun
Villa Cassia di Baccano
Aerial view

Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (65 reviews)
"Pros: 1. Beautiful property with an amazing view. 2. Spacious family suite 3. Comfortable bed 4. Quiet, waking up to birds singing in the morning. Cons: 1. Stink bugs in the suite; once we understood they are common this time of year and easy to capture and release outside, it was ok. 2. Showers are very small. 3. A/C not turned on this time of year; was not offered fans until the last day. 4. Minimal amenities. 5. Few outlets The villa is beautiful, just be prepared for a “rustic”...
United States
Niyo
The price is AED 536
AED 624 total
includes taxes & fees
21 Jun - 22 Jun
Villa Curina Resort
Exterior

Casa di Alice

Casa di Alice
Barberino Tavarnelle
8.0 out of 10, Very Good, (1 review)
"Very good "
Canada
richard
The price is AED 378
AED 433 total
includes taxes & fees
3 Jun - 4 Jun
Casa di Alice
Exterior

Il Pozzo di Sant'Andrea

Il Pozzo di Sant'Andrea
Siena
9.8 out of 10, Exceptional, (16 reviews)
"Great host, lovely place near Siena"
United Kingdom
Prem
The price is AED 388
AED 444 total
includes taxes & fees
3 Jun - 4 Jun
Il Pozzo di Sant'Andrea
Aerial view

Riserva di Fizzano Residence

Riserva di Fizzano Residence
3.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (32 reviews)
"Great place to stay in Tuscany! Very nice breakfast also!"
United States
Janet
The price is AED 846
AED 939 total
includes taxes & fees
10 Jun - 11 Jun
Riserva di Fizzano Residence
Studio, Patio, Ground Floor | Terrace/patio

Fullino Nero

Fullino Nero
Siena
9.6 out of 10, Exceptional, (52 reviews)
"Great stay! Clean rooms with air conditioning. Beautiful grounds "
United States
Christian
The price is AED 370
AED 424 total
includes taxes & fees
5 Jun - 6 Jun
Fullino Nero
Tasting room

Il Battistero Siena - Residenza d'Epoca

Il Battistero Siena - Residenza d'Epoca
Siena City Centre
9.6 out of 10, Exceptional, (210 reviews)
"Friendly staff and good location."
Canada
Yongseok
The price is AED 580
AED 655 total
includes taxes & fees
8 Jun - 9 Jun
Il Battistero Siena - Residenza d'Epoca
Property grounds

Domus il Palio B&B

Domus il Palio B&B
Ravacciano
9.2 out of 10, Wonderful, (90 reviews)
"Rooms were clean and spacious ! Happy there was a good blow dryer in the room and a heated towel rack. Staff were very friendly and helpful . Would stay again !"
Canada
Alissia
The price is AED 298
AED 345 total
includes taxes & fees
3 Jun - 4 Jun
Domus il Palio B&B
Breakfast meal

B&B Il Corso

B&B Il Corso
Siena City Centre
9.8 out of 10, Exceptional, (203 reviews)
"Excellent location, rooms, staff."
United States
Mario Humberto
The price is AED 433
AED 494 total
includes taxes & fees
25 Jun - 26 Jun
B&B Il Corso
Room amenity

Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (450 reviews)
"It’s very close to the historical center but feels quiet and like you are separate from it. I loved our stay"
United States
David
The price is AED 490
AED 556 total
includes taxes & fees
18 Jun - 19 Jun
Siena Vip
Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers

Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.4 out of 10, Exceptional, (32 reviews)
"Beautiful villa, very spacious, gorgeous property and great restaurant on the property to have a delicious meal. Staff very welcoming. Close to other main cities, like Siena, for day trips. We loved sitting by the pool, although it wasn’t heated, so too cold to use in April. We did love using the indoor heated pool and hot tub each day. We had a fabulous time and hope to go back someday! "
Canada
Jeremy
The price is AED 587
AED 646 total
includes taxes & fees
4 Jun - 5 Jun
Villa di Sotto
City view

Regis Condo

Regis Condo
Siena City Centre
9.4 out of 10, Exceptional, (71 reviews)
"Adequate basic clean room in a beautiful area."
United States
Margaret
The price is AED 495
AED 562 total
includes taxes & fees
3 Jun - 4 Jun
Regis Condo
Lunch and dinner served

Castello di Gargonza

Castello di Gargonza
3.0 star property
Monte San Savino
9.2 out of 10, Wonderful, (40 reviews)
"Beautiful historic fortress / castle with tastefully updated rooms, great amenities that maintains the old character "
Canada
Ariel
The price is AED 841
AED 943 total
includes taxes & fees
2 Jun - 3 Jun
Castello di Gargonza
Romantic Double Room, 1 Queen Bed, Hot Tub, Ground Floor | Private spa tub

DormiVeglia B&B

DormiVeglia B&B
Monte San Savino
10.0 out of 10, Exceptional, (28 reviews)
"Amazing, warm, sweet, lovely, such a gem of a place!"
American Samoa
Melissa Hyun Joo
The price is AED 351
AED 404 total
includes taxes & fees
3 Jun - 4 Jun
DormiVeglia B&B
Terrace/patio

Casa di Campagna in Toscana

Casa di Campagna in Toscana
Sovicille
9.4 out of 10, Exceptional, (24 reviews)
"A wonderful stay. "
United States
Sally
The price is AED 474
AED 534 total
includes taxes & fees
8 Jun - 9 Jun
Casa di Campagna in Toscana
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 AED 910
AED 1,018 total
includes taxes & fees
2 Jun - 3 Jun
Villa il Fedino
Outdoor dining

B&B La Fonte del Machiavelli

B&B La Fonte del Machiavelli
San Casciano in Val di Pesa
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 AED 474
AED 539 total
includes taxes & fees
2 Jun - 3 Jun
B&B La Fonte del Machiavelli
Suite | Premium bedding, Select Comfort beds, minibar, in-room safe

La Terrazza Sul Campo Rooming House

La Terrazza Sul Campo Rooming House
Siena City Centre
9.8 out of 10, Exceptional, (245 reviews)
"The location was amazing. I will never forget the view. Room was huge and access to restaurants and shopping. Also fantastic. We want to go back again already."
United States
Margaret
The price is AED 804
AED 901 total
includes taxes & fees
4 Jun - 5 Jun
La Terrazza Sul Campo Rooming House
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

Villa Sabolini

Villa Sabolini

10/10 Excellent
"Picturesque setting in the Tuscany hills. Beautifully maintained property."
Karla 3-night trip
Posted less than an hour ago
Villa Sabolini

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 an electric kettle. 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 Terme Antica Querciolaia. Badia a Coltibuono and Meleto Castle 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.