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

Montespertoli Holiday Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Montespertoli holiday rentals

A modern bedroom with a bed, bedside tables, a chair, a TV, and a view of the outdoors.

1. Holiday Home 'Blueyes house tuscany'

Holiday Home 'Blueyes house tuscany'
Montespertoli
The price is AU$252
includes taxes & fees
17 Nov - 18 Nov
Holiday Home 'Blueyes house tuscany'
Pool

2. 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$521
includes taxes & fees
16 Nov - 17 Nov
Tuscan Farmhouse with Private Pool & Chianti Vineyard Views - 3 Bedr + AC
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and hills.

3. 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$454
includes taxes & fees
16 Nov - 17 Nov
Villa Il Frantoio with Shared Pool, Private Terrace & Wi-Fi
A large swimming pool with sun loungers, a tennis court, and a view of rolling hills.

4. 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, (26 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$509
includes taxes & fees
16 Nov - 17 Nov
Tuscan Apart for 4/5 persons, WIFI, AIR-CO, SW-POOL, all comforts in the country
A dining area with a table set for four, surrounded by chairs, in front of a house with a stone facade and a wooden door.

5. Cozy apartment for 4/5 pax in a cottage in Chianti,Wifi,Swimmingpool,AIR-CO,Chef

Cozy apartment for 4/5 pax in a cottage in Chianti,Wifi,Swimmingpool,AIR-CO,Chef
Poppiano
8.0 out of 10, Very good, (3 reviews)
"Tuscany really is as lovely as we dreamed. We found the property communication to be excellent and registration very informative. The recommendations for sights and restaurants were absolutely spot on. We were two couples and the space does work well for two couples. One bedroom had an ensuite and the second bedroom had a bathroom adjacent. The kitchen is small but functional for 2. We would suggest that the property description be updated as it is a little misleading. The kitchen supplies are...
Canada
Dinah H.
The price is AU$509
includes taxes & fees
16 Nov - 17 Nov
Cozy apartment for 4/5 pax in a cottage in Chianti,Wifi,Swimmingpool,AIR-CO,Chef
A dining area with a table set for four, surrounded by chairs, in front of a house with a stone facade and a wooden door.

6. Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites

Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites
Montespertoli
10.0 out of 10, Exceptional, (42 reviews)
"Absolutely fabulous! Beautiful location, exceptional host and the Tuscan countryside dream. Room for all 11 of our ladies, dreamy grounds. We all felt like we were living our Eat, Love, Pray best life!"
United States
Krista G.
The price is AU$2,246
includes taxes & fees
29 Nov - 30 Nov
Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites
A villa with a swimming pool, surrounded by lush greenery and vineyards.

7. Villa with Guesthouse: Private Pool, Air Conditioning, 13 Bedrooms for up to 30 Guests

Villa with Guesthouse: Private Pool, Air Conditioning, 13 Bedrooms for up to 30 Guests
Montespertoli
The price is AU$8,796
includes taxes & fees
16 Nov - 17 Nov
Villa with Guesthouse: Private Pool, Air Conditioning, 13 Bedrooms for up to 30 Guests
A dining area with a table set for four, surrounded by chairs, in front of a house with a stone facade and a wooden door.

8. Luxury,Charming,in true Chianti, sleeps 21 or +people with Sw-Pool,Wi-Fi,Airco

Luxury,Charming,in true Chianti, sleeps 21 or +people with Sw-Pool,Wi-Fi,Airco
Montespertoli
10.0 out of 10, Exceptional, (12 reviews)
"Amazing Property! The house was impeccably clean, with spacious bedrooms and comfortable beds. Our gracious host Nicola spoiled us with his generosity. He went beyond our expectations to ensure that our stay was perfect. He and his wife welcomed us with a delicious homemade apple cake. He drove us to the nearby town of Montespertoli to pick-up groceries and provisions. He recommended a local chef to cook for us at the villa. The meal was amazing and memorable. We will be back!"
United States
Elise D.
The price is AU$2,229
includes taxes & fees
9 Dec - 10 Dec
Luxury,Charming,in true Chianti, sleeps 21 or +people with Sw-Pool,Wi-Fi,Airco
A swimming pool with lounge chairs and umbrellas, surrounded by trees.

9. 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$2,640
includes taxes & fees
17 Nov - 18 Nov
Villa Milani with Shared Pool, Private Terrace & Wi-Fi
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a view of rolling hills.

10. Villa 'Villa del Fattore' with Shared Pool, Private Terrace & Wi-Fi

Villa 'Villa del Fattore' with Shared Pool, Private Terrace & Wi-Fi
Montespertoli
8.0 out of 10, Very good, (4 reviews)
"Beautiful stay in a wonderful Italian villa. "
United States
Jessica C.
The price is AU$824
includes taxes & fees
16 Nov - 17 Nov
Villa 'Villa del Fattore' with Shared Pool, Private Terrace & Wi-Fi
A swimming pool with lounge chairs and tables, surrounded by grass and a view of hills.

11. 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, (2 reviews)
"Pros: Die Unterkunft ist geräumig und geschmackvoll toskanisch eingerichtet. Die Betten waren bequem, und es war ein Traum morgens ganz alleine im großen Pool seine Bahnen zu ziehen. Der Haustechniker war überaus freundlich und hilfsbereit. Cons: Die Vermieterin war nicht wirklich unfreundlich, aber ruppig und desinteressiert. Bei der Ankunft mussten wir erst einmal jemanden suchen, der uns empfängt. Es gab keine wirkliche Einweisung, wo die Mülltonnen stehen und wo man Wäsche waschen kann. Die...
Germany
Anonymous traveller
The price is AU$780
includes taxes & fees
16 Nov - 17 Nov
Villa 'La Limonaia' with Shared Pool, Private Terrace & Wi-Fi
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a view of rolling hills.

12. 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, (4 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$941
includes taxes & fees
16 Nov - 17 Nov
Apartment 'La Terrazza' with Shared Pool, Private Terrace & Wi-Fi
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a view of rolling hills.

13. 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$906
includes taxes & fees
16 Nov - 17 Nov
Apartment 'La Torre' with Shared Pool, Private Terrace & Wi-Fi
A pool area with a view of rolling hills and a clear sky.

14. B&B La Fonte del Machiavelli

B&B La Fonte del Machiavelli
San Casciano in Val di Pesa
9.2 out of 10, Wonderful, (94 reviews)
"The view is unique. Perfect location for a romantic trip."
United States
Stella
The price is AU$192
includes taxes & fees
16 Nov - 17 Nov
B&B La Fonte del Machiavelli
A villa with multiple bedrooms, a swimming pool, and a garden.

15. Relais Villa Olmo - Place of Charme

Relais Villa Olmo - Place of Charme
Impruneta
9.6 out of 10, Exceptional, (277 reviews)
"Great property and staff. Highly recommend!"
United States
Michael
The price is AU$158
includes taxes & fees
22 Nov - 23 Nov
Relais Villa Olmo - Place of Charme
An arched entrance with a lantern above, flanked by two potted plants.

16. Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (109 reviews)
"Food was amazing, we love how quiet and relaxing it was"
United States
Justyna
The price is AU$262
includes taxes & fees
25 Nov - 26 Nov
Villa il Fedino
A swimming pool with people enjoying the water, a wooden deck, and a covered seating area.

17. hu Firenze Certosa camping in town

hu Firenze Certosa camping in town
Impruneta
8.6 out of 10, Excellent, (128 reviews)
"Very helpful staff and comfortable affordable stay"
United States
Ana María
The price is AU$82
includes taxes & fees
16 Nov - 17 Nov
hu Firenze Certosa camping in town
A swimming pool with clear blue water, surrounded by tall trees and a stone patio with lounge chairs.

18. Fattoria il Milione Agriturismo

Fattoria il Milione Agriturismo
4.0 star property
Florence
8.2 out of 10, Very good, (284 reviews)
"Great location for a Tuscany experience ."
United States
Bond
The price is AU$117
includes taxes & fees
16 Nov - 17 Nov
Fattoria il Milione Agriturismo
A rural landscape with a house surrounded by lush greenery and a small pool.

19. Marignolle Relais and Charme

Marignolle Relais and Charme
Florence
9.2 out of 10, Wonderful, (94 reviews)
"The Marignolle Relais & Charme is absolutely gorgeous. The rooms are beautifully decorated and everything is so clean. The grounds are well maintained and the pool area is stunning. We loved our two day stay and heartily recommend it. Stay here you’ll love it!!!"
Canada
Honey
The price is AU$227
includes taxes & fees
9 Dec - 10 Dec
Marignolle Relais and Charme
A dining area with tables set for meals, a chandelier, and a view of the outdoors.

20. Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.6 out of 10, Exceptional, (104 reviews)
"We love this beautiful exquisitely appointed hotel in a town with unexpected treasures and great food "
United Kingdom
John
The price is AU$191
includes taxes & fees
3 Dec - 4 Dec
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 Montespertoli Hotel Reviews

The Social Hub Florence Belfiore

The Social Hub Florence Belfiore

10/10 Excellent
"Highly recommend this hotel! Excellent location-walking distance to train stations and 5 minutes from the airport. The check-in was seamless. Our room was spacious and clean . The rooftop bar was a nice surprise! And they had a wonderful restaurant on the first floor."
OLIVIA 1-night trip
Posted less than an hour ago
The Social Hub Florence Belfiore

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$82 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.

How many holiday rentals are there in Montespertoli?

Choose from 17 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.