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Check prices for these dates

In two weeks
6 Mar - 8 Mar
In two months
17 Apr - 19 Apr
In three months
15 May - 17 May
In four months
12 Jun - 14 Jun

Our top choices for Montaione holiday rentals

Property entrance

Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (99 reviews)
"Great people, great location great service"
Canada
James
The price is 3.840.185 ₫
4.347.313 ₫ total
includes taxes & fees
18 Feb - 19 Feb
Villa il Fedino
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
Antico Borgo Poggiarello
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 2.266.339 ₫
2.585.305 ₫ total
includes taxes & fees
20 Feb - 21 Feb
Borgo San Giusto
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
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
Marignolle Relais and Charme
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 2.518.154 ₫
2.769.970 ₫ total
includes taxes & fees
18 Feb - 19 Feb
B&B Il Moscondoro
1 bedroom, in-room safe, desk, free cots/infant beds

B&B Cindy

B&B Cindy
Cascina
8.2 out of 10, Very good, (130 reviews)
"Great stay near Pisa"
United Kingdom
A
The price is 1.993.454 ₫
2.192.892 ₫ total
includes taxes & fees
19 Feb - 20 Feb
B&B Cindy
Front of property

Villa Scorzi

Villa Scorzi
Calci
9.8 out of 10, Exceptional, (8 reviews)
"This is the type of resort you go to Tuscany for. Great history and great staff. It makes you feel like you have stepped back in time. "
United States
Don
The price is 2.872.556 ₫
3.498.363 ₫ total
includes taxes & fees
18 Feb - 19 Feb
Villa Scorzi
Apartment, 1 Bedroom, Ground Floor (Garden) | Exterior

Residence Il Paradiso

Residence Il Paradiso
3.0 star property
Guardistallo
8.4 out of 10, Very good, (26 reviews)
"Absolutely beautiful property among the pine trees. Nice little restaurant, ideal pools and play area for little kids. Location is perfect for exploring the region. Great beaches only 10-15 minutes away. The apartment was very clean and everything necessary for our stay was available. Would gladly visit again. Thank you Il Paradiso!"
Germany
Jason
The price is 2.346.779 ₫
2.735.498 ₫ total
includes taxes & fees
19 Feb - 20 Feb
Residence Il Paradiso
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 2.039.805 ₫
2.397.673 ₫ total
includes taxes & fees
3 Mar - 4 Mar
La Casa di Ines
Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool loungers

Lebbiano Residence Bio Resort

Lebbiano Residence Bio Resort
3.0 star property
Scandicci
9.4 out of 10, Exceptional, (23 reviews)
"Vicino a Firenze e quindi alle principali via di scambi, ma in una tranquillità disarmante. Il silenzio è parte integrante della struttura, ma sia chiaro assolutamente positivo. La struttura è ubicata in una zona veramente bella e le stanze sono confortevoli, comode e con la possibilità di cucinare. Infine fatevi coccolare dalla colazione servita in compagnia di uno stupendo gattone rosso e dalla bella Camilla. ;-)"
Italy
Matteo
The price is 3.807.169 ₫
4.957.322 ₫ total
includes taxes & fees
7 Mar - 8 Mar
Lebbiano Residence Bio Resort
View from room

Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Barberino Tavarnelle
8.6 out of 10, Excellent, (112 reviews)
"Spacious room in large resort style complex, set up as fully self contained with kitchen and dining furniture. Peaceful location with lovely views. Very pleasant staff and exceptional breakfast. "
France
Richard
Chianti Village Morrocco
Terrace/patio

Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.8 out of 10, Exceptional, (98 reviews)
"We love this beautiful exquisitely appointed hotel in a town with unexpected treasures and great food "
United Kingdom
John
The price is 3.350.972 ₫
3.747.712 ₫ total
includes taxes & fees
8 Mar - 9 Mar
Palazzo Pacini
Property entrance

Affittacamere a 20 minuti da Firenze

Affittacamere a 20 minuti da Firenze
Empoli
8.2 out of 10, Very good, (21 reviews)
"Very basic lodgings - simple but good location between Florence & Pisa. Breakfast place right underneath the rooms made breakfast convenient. Parking was super simple & across the street, which is rare in Italy. "
United States
Scott
The price is 2.477.891 ₫
2.818.012 ₫ total
includes taxes & fees
18 Feb - 19 Feb
Affittacamere a 20 minuti da Firenze
Exterior detail

appartamenti la piazzetta

appartamenti la piazzetta
Signa
9.6 out of 10, Exceptional, (4 reviews)
"Oui"
France
Teresa
The price is 1.879.270 ₫
3.267.640 ₫ total
includes taxes & fees
23 Feb - 24 Feb
appartamenti la piazzetta
Seasonal outdoor pool, pool umbrellas, pool loungers

Rocca Palazzaccio

Rocca Palazzaccio
3.0 star property
Impruneta
9.0 out of 10, Wonderful, (14 reviews)
"A lovely stay at this property with our 2 year old.The apartment had everything we needed and communication with the host was very good There are steep hills to access the property by car or foot so bear that in mind but we managed fine with a pram and a car its just worth noting Handy to have laundry facilities on site aswell. There is a coop just a few minutes down the road Lovely views and a clean pool which was perfect for our little one to use and toys there that he could play in the...
United Kingdom
Lauren
Rocca Palazzaccio
Deluxe Room, Patio | Frette Italian sheets, premium bedding, minibar, in-room safe

Tenuta Sant'Ilario

Tenuta Sant'Ilario
Gambassi Terme
9.4 out of 10, Exceptional, (34 reviews)
"Amazing location and property! Owner and staff super nice! I am sure we will be back!"
Australia
Ilaria
Tenuta Sant'Ilario
Daily self-service breakfast (EUR 6 per person)

Beatabb

Beatabb
Guardistallo
9.0 out of 10, Wonderful, (8 reviews)
"The host was lovely and this was the most beautiful place to stay and wish we had stayed longer "
United Kingdom
Sheena
Beatabb
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, (232 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 2.017.041 ₫
2.649.629 ₫ total
includes taxes & fees
18 Feb - 19 Feb
Fattoria il Milione Agriturismo
Breakfast, lunch, dinner served; Regional cuisine

La Locanda di Pietracupa

La Locanda di Pietracupa
Barberino Tavarnelle
9.4 out of 10, Exceptional, (35 reviews)
"Great place, wonderful restaurant"
Germany
Isabell
La Locanda di Pietracupa
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 Montaione Hotel Reviews

Castelfalfi

Castelfalfi

10/10 Excellent
"Beautiful property "
steven 2-night trip
Posted 3 months ago
Castelfalfi

Frequently asked questions

Can I find holiday rentals in Montaione?

Yes, there are holiday rentals close to the most popular sights in Montaione, or you can select a more secluded option if you're looking for a relaxing stay. Montaione is known for its wineries and golf courses. Make sure you have time to check out the spas and seafood restaurants during your trip.

How many holiday rentals are there in Montaione?

With 49 Expedia holiday rentals, you're guaranteed to find just the right place for your Montaione stay.

What’s there to see and do in Montaione?

Explore the area and family-friendly sights such as Tenuta San Vito, or get out into nature at a spot like Casciana Thermal Baths. Castelfalfi Golf Course and Monastery of San Vivaldo are other places to visit while you're in town.

What’s a holiday rental in Montaione like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Montaione. Holiday rentals feature extras like kitchens and laundry facilities so your stay will be comfortable. If you're concerned about cleanliness, holiday rentals can offer a sense of seclusion away from shared hotel lifts and busy concierge desks while still allowing you to travel. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular choice for family gatherings.