Montegrossi Vacation Rentals

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Check prices for these dates

In two weeks
May 8 - May 10
In two months
Jun 19 - Jun 21
In three months
Jul 17 - Jul 19
In four months
Aug 14 - Aug 16

Our top choices for Montegrossi vacation rentals

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 ￥25,833
￥28,416 total
includes taxes & fees
May 18 - May 19
Villa Cassia di Baccano
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 ￥15,646
￥17,958 total
includes taxes & fees
Apr 27 - Apr 28
Il Pozzo di Sant'Andrea
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
The price is ￥10,894
￥12,357 total
includes taxes & fees
Apr 27 - Apr 28
Chianti Village Morrocco
Premium bedding, down comforters, pillowtop beds, minibar

Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.0 out of 10, Wonderful, (26 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is ￥11,091
￥14,628 total
includes taxes & fees
May 3 - May 4
Tuscasì Aparthotel
1 bedroom, free WiFi, bed sheets

Cosy double room in pretty cottage with WiFi and AC in enchanting Monteaperti

Cosy double room in pretty cottage with WiFi and AC in enchanting Monteaperti
Monteaperti
10.0 out of 10, Exceptional, (2 reviews)
"We loved this place. Modern cabin set in a rustic Tuscan setting. Beautiful property, very comfortable stay, and very attentive staff. Family owned and operated. Amazing restaurant just steps away. A perfect place for respite"
United States
Ian F.
The price is ￥29,892
￥35,123 total
includes taxes & fees
Apr 29 - Apr 30
Cosy double room in pretty cottage with WiFi and AC in enchanting Monteaperti
Villa, Air conditioning, Courtyard View | Exterior

Villa Montecastello

Villa Montecastello
Monteriggioni
The price is ￥26,951
￥30,207 total
includes taxes & fees
Apr 27 - Apr 28
Villa Montecastello
Studio, Patio, Ground Floor | Terrace/patio

Fullino Nero

Fullino Nero
Siena
9.6 out of 10, Exceptional, (51 reviews)
"Great stay! Clean rooms with air conditioning. Beautiful grounds "
United States
Christian
The price is ￥16,151
￥18,513 total
includes taxes & fees
Apr 27 - Apr 28
Fullino Nero
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 ￥24,381
￥35,030 total
includes taxes & fees
Apr 28 - Apr 29
Chianti Craft House Badia a Passignano
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 ￥28,278
￥31,666 total
includes taxes & fees
Apr 27 - Apr 28
Antico Borgo Poggiarello
Lunch and dinner served, local cuisine

Castello di Gargonza

Castello di Gargonza
3.0 star property
Monte San Savino
9.2 out of 10, Wonderful, (40 reviews)
"Beautiful area and friendly staff. We stayed here several years ago and were so excited to return."
United States
David
The price is ￥36,707
￥41,125 total
includes taxes & fees
Apr 27 - Apr 28
Castello di Gargonza
Exterior

Villa Mucellena

Villa Mucellena
Casole d'Elsa
The price is ￥16,305
￥18,310 total
includes taxes & fees
Apr 27 - Apr 28
Villa Mucellena
Terrace/patio

Casa di Campagna in Toscana

Casa di Campagna in Toscana
Sovicille
9.4 out of 10, Exceptional, (21 reviews)
"Fantastic experience with friendly hosts and an excellent breakfast! A little rustic here and there but all part of the charm!"
United Kingdom
Alasdair
The price is ￥19,687
￥22,215 total
includes taxes & fees
May 8 - May 9
Casa di Campagna in Toscana
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 ￥13,859
￥15,992 total
includes taxes & fees
Apr 27 - Apr 28
DormiVeglia B&B
Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers

Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.4 out of 10, Exceptional, (30 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 ￥25,863
￥28,449 total
includes taxes & fees
Apr 29 - Apr 30
Villa di Sotto
Property amenity

Camping Village Il Poggetto.

Camping Village Il Poggetto.
3.0 star property
Rignano sull'Arno
8.0 out of 10, Very Good, (68 reviews)
"Pet friendly and clean"
United Kingdom
Nancy
The price is ￥10,380
￥11,978 total
includes taxes & fees
Apr 28 - Apr 29
Camping Village Il Poggetto.
Aerial view

Riserva di Fizzano Residence

Riserva di Fizzano Residence
3.0 star property
Castellina in Chianti
9.8 out of 10, Exceptional, (25 reviews)
"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
The price is ￥32,405
￥36,019 total
includes taxes & fees
May 17 - May 18
Riserva di Fizzano Residence
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, (241 reviews)
"My first time in Siena and this Rooming House turned out to be a great choice. The view onto the piazza is a real bonus, as is the great location in the heart of the city. The host was lovely and a great communicator. The room itself was fantastic and spacious. I would recommend it and will book again. "
United Kingdom
Jeffrey William
The price is ￥18,489
￥21,085 total
includes taxes & fees
May 12 - May 13
La Terrazza Sul Campo Rooming House
Terrace/patio

Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.8 out of 10, Exceptional, (99 reviews)
"A nice blend of old world charm and modern conveniences. It is far from "
United States
John
The price is ￥17,035
￥19,113 total
includes taxes & fees
May 4 - May 5
Palazzo Pacini
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 ￥18,959
￥21,602 total
includes taxes & fees
Apr 27 - Apr 28
B&B La Fonte del Machiavelli
Property grounds

Ca' Bianca Tuscany Relais

Ca' Bianca Tuscany Relais
Siena
10.0 out of 10, Exceptional, (44 reviews)
"Clean room, amazing staff"
Canada
Talha
The price is ￥38,013
￥42,561 total
includes taxes & fees
Apr 29 - Apr 30
Ca' Bianca Tuscany Relais
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

Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione

10/10 Excellent
"Perfect and beautiful Thank you"
Rodrigo 1-night trip
Posted 3 hours ago
Grand Hotel Continental Siena – Starhotels Collezione

Find out more about Montegrossi

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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 an espresso 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 Terme Antica Querciolaia. Badia a Coltibuono and Medieval Tower of Barbischio 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.