A rural landscape with olive groves, scattered houses, and rolling hills in the background.

Montespertoli Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Montespertoli holiday rentals

1. Villa Il Frantoio with Shared Pool, Private Terrace & Wi-Fi

Villa Il Frantoio with Shared Pool, Private Terrace & Wi-Fi
Montespertoli
The price is AU$264
includes taxes & fees
1 Sept - 2 Sept
Villa Il Frantoio with Shared Pool, Private Terrace & Wi-Fi

2. Blueyes House Tuscany

Blueyes House Tuscany
Montespertoli
The price is AU$250
includes taxes & fees
1 Sept - 2 Sept
Blueyes House Tuscany

3. Villa Latini Agriturismo La Capanna

Villa Latini Agriturismo La Capanna
Montespertoli
Villa Latini Agriturismo La Capanna

4. Il Melograno, Chianti apartment in farmhouse for 4 people with garden

Il Melograno, Chianti apartment in farmhouse for 4 people with garden
Montespertoli
Il Melograno, Chianti apartment in farmhouse for 4 people with garden

5. Tuscan Apart for 4/5 persons, WIFI, AIR-CO, SW-POOL, all comforts in the country

Tuscan Apart for 4/5 persons, WIFI, AIR-CO, SW-POOL, all comforts in the country
Montespertoli
10.0 out of 10, Exceptional, (24 reviews)
"Great location. Wonderful property. The host was very accessible and super helpful with places to visit, eat, etc. will definitely be back! "
United States
Todd F.
The price is AU$603
includes taxes & fees
21 Aug - 22 Aug
Tuscan Apart for 4/5 persons, WIFI, AIR-CO, SW-POOL, all comforts in the country

6. Tuscan Farmhouse with Private Pool & Chianti Vineyard Views - 3 Bedr + AC

Tuscan Farmhouse with Private Pool & Chianti Vineyard Views - 3 Bedr + AC
Montespertoli
10.0 out of 10, Exceptional, (1 review)
"We found sanctuary at this lovely farmhouse during the July heat wave--refreshing dip in the pool, relaxing dinner in the courtyard, restful sleep in the air-conditioned home. Got up to watch the sunrise over the vineyards, absolutely stunning scenery, and watched three hot air balloons also taking in the sights. Matteo was very welcoming, and we bridged the language barrier with a little help from Google translate. Wished we could have stayed longer!"
United States
Susan A.
The price is AU$782
includes taxes & fees
8 Sept - 9 Sept
Tuscan Farmhouse with Private Pool & Chianti Vineyard Views - 3 Bedr + AC

7. La Quercia, apartment with garden for 6/8 people in the heart of Chianti

La Quercia, apartment with garden for 6/8 people in the heart of Chianti
Montespertoli
10.0 out of 10, Exceptional, (2 reviews)
"We had a wonderful 7 day stay. The location is perfect. It is an easy drive to all the towns in Tuscany. The property is beautiful and quiet. The views are amazing. Patrizia was a great host and very helpful with restaurant and winery recommendations."
United States
Mark S.
La Quercia, apartment with garden for 6/8 people in the heart of Chianti

8. Villa Milani with Shared Pool, Private Terrace & Wi-Fi

Villa Milani with Shared Pool, Private Terrace & Wi-Fi
Montespertoli
10.0 out of 10, Exceptional, (1 review)
"The Villa was charming and absolutely bursting with character. We loved exploring the house and the grounds! It was quiet and relaxing, but still only a short drive from Florence, Sienna, San Gimignano and other favorite towns of Tuscany. A memorable stay in an absolutely unique villa!"
United States
Scott M.
The price is AU$3,529
includes taxes & fees
1 Sept - 2 Sept
Villa Milani with Shared Pool, Private Terrace & Wi-Fi

9. Villa 'La Limonaia' with Shared Pool, Private Terrace & Wi-Fi

Villa 'La Limonaia' with Shared Pool, Private Terrace & Wi-Fi
Montespertoli
6.0 out of 10, (1 review)
"Une magnifique propriété viticole, dans un environnement superbe en plein milieu des vignes de Chianti et des oliviers, à environ 50 mn en voiture de Florence, Pise, Sienne, qui aurait pu être synonyme de séjour parfait si nous n'avions été constamment ennuyés par différents problèmes de confort, de bruit et de maintenance. La Limonaia se trouve juste au dessous de la terrasse d'un appartement, sans aucune isolation et le moindre bruit de pas ou de mobilier déplacé est amplifié. Nous n'avons...
France
SERGE P.
The price is AU$1,215
includes taxes & fees
18 Aug - 19 Aug
Villa 'La Limonaia' with Shared Pool, Private Terrace & Wi-Fi

10. Apartment 'La Terrazza' with Shared Pool, Private Terrace & Wi-Fi

Apartment 'La Terrazza' with Shared Pool, Private Terrace & Wi-Fi
Montespertoli
10.0 out of 10, Exceptional, (3 reviews)
"We had the best time. The view is spectacular. The rooms are spacious very secure property. The property was clean and well appointed. We had a special request during our stay of a chef to cook us a real Italian meal. Our host Elena took the challenge on herself with the help of her family. The meal she cooked was the highlight of our entire vacation. She was a great host to deal with and we’d love to go back there again."
United States
Charlie B.
The price is AU$885
includes taxes & fees
16 Aug - 17 Aug
Apartment 'La Terrazza' with Shared Pool, Private Terrace & Wi-Fi

11. Apartment 'La Torre' with Shared Pool, Private Terrace & Wi-Fi

Apartment 'La Torre' with Shared Pool, Private Terrace & Wi-Fi
Montespertoli
4.0 out of 10, (1 review)
"Die Wohnung war im Internet nicht deutlich dargestellt. Die 140 m² sind vom Nutzen her nicht zutreffend. Das Wohnzimmer direkt unter dem heißen Dachstuhl haben wir gar nicht nutzen können, die Küche nur schnell schnell. Sie war viel zu klein, viele Utensilien fehlten, um für eine Familie zu kochen und zu essen. Die Küche war in einer Zwischenetage, die Schlafzimmer in der ersten Etage, so dass sich die ganze Fläche auf 2,5 Etagen mit vielen Treppen und Fluren verteilte. Es war fast ziemlich...
Germany
Havva C.
The price is AU$1,199
includes taxes & fees
16 Aug - 17 Aug
Apartment 'La Torre' with Shared Pool, Private Terrace & Wi-Fi

12. hu Firenze Certosa camping in town

hu Firenze Certosa camping in town
Impruneta
8.4 out of 10, Very good, (97 reviews)
"Lovely location in the hills. Really nice pool and bar."
United Kingdom
Jessica
The price is AU$86
includes taxes & fees
23 Aug - 24 Aug
hu Firenze Certosa camping in town

13. I Parigi Corbinelli

I Parigi Corbinelli
Florence
9.6 out of 10, Exceptional, (168 reviews)
"Charming place, great welcoming"
United Kingdom
Stefano
The price is AU$168
includes taxes & fees
16 Aug - 17 Aug
I Parigi Corbinelli

14. Sette Angeli Rooms

Sette Angeli Rooms
Historic Centre of Florence
8.8 out of 10, Excellent, (678 reviews)
"Good clean rooms and very close to the city center as well as the train station"
United Kingdom
VISHAL
The price is AU$137
includes taxes & fees
16 Aug - 17 Aug
Sette Angeli Rooms

15. La Senesina, Monteriggioni, Siena. In the best countryside of Tuscany !

La Senesina, Monteriggioni, Siena. In the best countryside of Tuscany !
Siena
10.0 out of 10, Exceptional, (66 reviews)
"Super helpful host"
Australia
Robyn D.
The price is AU$386
includes taxes & fees
5 Sept - 6 Sept
La Senesina, Monteriggioni, Siena. In the best countryside of Tuscany !

16. Antico Borgo il Cardino

Antico Borgo il Cardino
San Gimignano
9.4 out of 10, Exceptional, (84 reviews)
"It was perfect for my one night stop before moving on to another location in Toscana."
United States
Craig
The price is AU$281
includes taxes & fees
6 Sept - 7 Sept
Antico Borgo il Cardino

17. Palazzo al Torrione 2

Palazzo al Torrione 2
San Gimignano City Centre
9.2 out of 10, Wonderful, (110 reviews)
"Great location, beautiful room with a terrace and the best breakfast we had in Italy! "
United States
Angel
The price is AU$218
includes taxes & fees
16 Aug - 17 Aug
Palazzo al Torrione 2

18. Villa San Filippo

Villa San Filippo
4.0 star property
Barberino Tavarnelle
8.6 out of 10, Excellent, (47 reviews)
"This place was beautiful, quiet like a picture you’d see in the movies"
Canada
Nadia
The price is AU$167
includes taxes & fees
13 Sept - 14 Sept
Villa San Filippo

19. Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Barberino Tavarnelle
8.6 out of 10, Excellent, (116 reviews)
"Front desk was very helpful and very comfortable room. "
United States
Chris
The price is AU$161
includes taxes & fees
1 Sept - 2 Sept
Chianti Village Morrocco

20. DomuS Miniato

DomuS Miniato
San Miniato
10.0 out of 10, Exceptional, (2 reviews)
"Super clean, felt brand new with a beaaautiful view on the terrace! Quite a few stairs (heavy luggage :D) but definitely worth it! Sadly we only stayed two nights"
United Kingdom
Celesta
The price is AU$169
includes taxes & fees
3 Sept - 4 Sept
DomuS Miniato
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

Top Montespertoli Hotel Reviews

Find out more about Montespertoli

Everything you need to know about Montespertoli holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Montespertoli holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Montespertoli holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Montespertoli holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Montespertoli. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Montespertoli holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Montespertoli holiday rentals we have selected for you start as low as AU$112 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Montespertoli rentals

At Expedia, we put the best Montespertoli holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Montespertoli rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Montespertoli holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Montespertoli. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Montespertoli?

Yes, there are holiday rentals in Montespertoli close to Il Fiaschetto, or you can select a more secluded option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the countryside in Montespertoli. Make sure you have time to check out the wineries and gardens during your trip.

What are some of the best holiday rentals that Montespertoli has to offer?

Villa La Stella - Casa per Ferie: This holiday home rental outside of Montespertoli is located near the airport, and has a garden, a library and air conditioning to put you at ease in your new surroundings. This holiday rental also comes with free parking to give you added peace of mind. Another good choice for your trip to Montespertoli is House with character in typical medieval borgo on the Chianti Classico hills.

How many holiday rentals are there in Montespertoli?

Choose from 18 Expedia holiday rentals in Montespertoli for a memorable holiday.

What’s there to see and do in Montespertoli?

Cultural attractions include Vine and Wine Museum, whereas Il Fiaschetto is just one of the family-friendly sights. Piazza di Santa Maria Novella and Piazza del Duomo are other popular places to visit in the area.

What are holiday rentals like in Montespertoli?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Montespertoli. Holiday rentals offer amenities like kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about a clean environment, holiday rentals can provide a sense of security away from public hotel lifts and busy lobbies while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive option for a small group gathering.