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

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Montespertoli holiday rentals

A swimming pool with lounge chairs and umbrellas, surrounded by greenery and hills.

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 £126
includes taxes & fees
28 Sept - 29 Sept
Villa Il Frantoio with Shared Pool, Private Terrace & Wi-Fi
A modern bedroom with a bed, bedside tables, a chair, a TV, and a view of the outdoors.

2. Holiday Home 'Blueyes house tuscany'

Holiday Home 'Blueyes house tuscany'
Montespertoli
The price is £122
includes taxes & fees
28 Sept - 29 Sept
Holiday Home 'Blueyes house tuscany'
A villa with a swimming pool, surrounded by lush greenery and vineyards.

3. 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 £5,163
includes taxes & fees
14 Oct - 15 Oct
Villa with Guesthouse: Private Pool, Air Conditioning, 13 Bedrooms for up to 30 Guests
An open doorway leading to an outdoor patio with a wooden table and chairs, a stone floor, and a wooden barrel with bottles.

4. 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 £380
includes taxes & fees
14 Oct - 15 Oct
Tuscan Farmhouse with Private Pool & Chianti Vineyard Views - 3 Bedr + AC
A stone building with a gravel path, potted plants, and a large vase with flowers.

5. 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
A dining room with a large wooden table, chairs, a chandelier, and a painting on the wall.

6. 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 £1,704
includes taxes & fees
30 Sept - 1 Oct
Villa Milani with Shared Pool, Private Terrace & Wi-Fi
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.

7. 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 £1,590
includes taxes & fees
28 Sept - 29 Sept
Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites
A swimming pool with lounge chairs and tables, surrounded by grass and a view of hills.

8. 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 £373
includes taxes & fees
28 Sept - 29 Sept
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.

9. 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 £497
includes taxes & fees
1 Oct - 2 Oct
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.

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 £435
includes taxes & fees
1 Oct - 2 Oct
Villa 'Villa del Fattore' with Shared Pool, Private Terrace & Wi-Fi
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a view of rolling hills.

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 £478
includes taxes & fees
1 Oct - 2 Oct
Apartment 'La Torre' with Shared Pool, Private Terrace & Wi-Fi
An arched entrance with a lantern above, flanked by two potted plants.

12. Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (105 reviews)
"Tha parking was easy on the property. It was within walking distance to the villages with shops, restaurants and cafes. The best part was the staff. The owners were incredibly helpful, friendly and made you feel like family. Breakfast outside was lovely overlooking the hills of Tuscany. We met many people and had lovely conversations with other travelers during breakfast. A gem in Tuscany."
United States
Lori
The price is £196
includes taxes & fees
25 Oct - 26 Oct
Villa il Fedino
A spacious indoor area with arched windows, wooden furniture, and hanging plants.

13. Relais Villa Olmo

Relais Villa Olmo
Impruneta
9.4 out of 10, Exceptional, (268 reviews)
"Very friendly and clean."
United States
Mohamed
The price is £143
includes taxes & fees
19 Oct - 20 Oct
Relais Villa Olmo
A water park with a pool, slides, and a wooden deck area.

14. hu Firenze Certosa camping in town

hu Firenze Certosa camping in town
Impruneta
8.4 out of 10, Very good, (107 reviews)
"Lovely location in the hills. Really nice pool and bar."
United Kingdom
Jessica
The price is £39
includes taxes & fees
12 Oct - 13 Oct
hu Firenze Certosa camping in town
A room with a dining table, a vase of flowers, a lamp, and a view of a historic building through a window.

15. Mamo Florence - Le Farine Della Signoria Apartments

Mamo Florence - Le Farine Della Signoria Apartments
Historic Centre of Florence
8.6 out of 10, Excellent, (10 reviews)
"Amazing property with excellent views. "
United States
Karl
The price is £191
includes taxes & fees
28 Oct - 29 Oct
Mamo Florence - Le Farine Della Signoria Apartments
An open wooden door leading to an outdoor patio with a table and chairs.

16. Palazzo al Torrione 2

Palazzo al Torrione 2
San Gimignano City Centre
9.2 out of 10, Wonderful, (113 reviews)
"They were very helpful to me when I arrived. I difficulty accessing there messages to me. They put me at ease"
United States
Angela
The price is £115
includes taxes & fees
28 Sept - 29 Sept
Palazzo al Torrione 2
A view from a window overlooking a rural landscape with fields and a distant mountain range.

17. B&B Palazzo Tortoli

B&B Palazzo Tortoli
San Gimignano City Centre
9.2 out of 10, Wonderful, (65 reviews)
"In the center of town overlooking a plaza (other rooms overlook the valley). Multiple museums, and dining and shopping options within very easy walking distance. The town and surroundings are beautiful."
United States
Harold
The price is £108
includes taxes & fees
28 Oct - 29 Oct
B&B Palazzo Tortoli
A narrow alleyway with brick walls, wooden barrels, and potted plants.

18. San Gimignano Apartment in the Heart of Town for 4 People with Fast Wi-Fi and Concierge Service

San Gimignano Apartment in the Heart of Town for 4 People with Fast Wi-Fi and Concierge Service
San Gimignano City Centre
9.8 out of 10, Exceptional, (42 reviews)
"Authentic 13th century building with so much character and charm. The room was very unique and opened to a lovely courtyard. The location was great, and very close to the gate. A full Italian breakfast buffet was offered at a reasonable cost. Laundry service was also available. And the hosts were very friendly and helpful."
United States
Marilyn H.
The price is £149
includes taxes & fees
19 Oct - 20 Oct
San Gimignano Apartment in the Heart of Town for 4 People with Fast Wi-Fi and Concierge Service
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

Hotel Albani Firenze

Hotel Albani Firenze

8/10 Good
"The croissants and cappuccinos at breakfast were delicious. It was in a good location, close to the train station. The room and staff were decent."
Caroline 4-night trip
Posted 1 hour ago
Hotel Albani Firenze

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, apart-hotels, 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 favorite 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 depends 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 £39 per night. Entering your travel dates in the search wizard you might find 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 16 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.