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

Montespertoli Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

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

Our top choices for Montespertoli vacation 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 CA $166
CA $226 total
includes taxes & fees
Oct 4 - Oct 5
Holiday Home 'Blueyes house tuscany'
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and hills.

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

Villa Il Frantoio with Shared Pool, Private Terrace & Wi-Fi
Montespertoli
The price is CA $443
CA $447 total
includes taxes & fees
Oct 3 - Oct 4
Villa Il Frantoio with Shared Pool, Private Terrace & Wi-Fi
A dining area with a table set for two, a view of a vineyard, and a wooden table with a small decorative item.

3. Villa Latini Agriturismo La Capanna

Villa Latini Agriturismo La Capanna
Montespertoli
Villa Latini Agriturismo La Capanna
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 CA $323
CA $685 total
includes taxes & fees
Oct 14 - Oct 15
Tuscan Farmhouse with Private Pool & Chianti Vineyard Views - 3 Bedr + AC
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 CA $416
CA $473 total
includes taxes & fees
Nov 2 - Nov 3
Cozy apartment for 4/5 pax in a cottage in Chianti,Wifi,Swimmingpool,AIR-CO,Chef
A stone building with a gravel path, potted plants, and a large vase with flowers.

6. 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 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 CA $9,596
CA $9,602 total
includes taxes & fees
Oct 18 - Oct 19
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 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 CA $2,719
CA $3,112 total
includes taxes & fees
Nov 1 - Nov 2
Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites
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.

9. Luxury,Charming,in true Chianti, sleeps 22 or +/- pople., with AIR-CONDITION!!!!

Luxury,Charming,in true Chianti, sleeps 22 or +/- pople., with AIR-CONDITION!!!!
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 CA $2,639
CA $3,021 total
includes taxes & fees
Nov 1 - Nov 2
Luxury,Charming,in true Chianti, sleeps 22 or +/- pople., with AIR-CONDITION!!!!
A dining room with a large wooden table, chairs, a chandelier, and a painting on the wall.

10. 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 CA $2,879
CA $2,882 total
includes taxes & fees
Nov 1 - Nov 2
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.

11. 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 CA $806
CA $809 total
includes taxes & fees
Oct 3 - Oct 4
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.

12. 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 CA $763
CA $766 total
includes taxes & fees
Oct 3 - Oct 4
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.

13. 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 CA $921
CA $924 total
includes taxes & fees
Oct 3 - Oct 4
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.

14. 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 CA $887
CA $890 total
includes taxes & fees
Oct 3 - Oct 4
Apartment 'La Torre' with Shared Pool, Private Terrace & Wi-Fi
An arched entrance with a lantern above, flanked by two potted plants.

15. 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 CA $310
CA $348 total
includes taxes & fees
Oct 8 - Oct 9
Villa il Fedino
A spacious indoor area with arched windows, wooden furniture, and hanging plants.

16. 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 CA $185
CA $209 total
includes taxes & fees
Nov 2 - Nov 3
Relais Villa Olmo
A courtyard with a stone building featuring an arched entrance, potted plants, and outdoor seating.

17. I Parigi Corbinelli

I Parigi Corbinelli
Florence
9.6 out of 10, Exceptional, (170 reviews)
"Beautiful setting, stunning views, incredible pool and gardens and so easy to jump on the bus into the city."
United Kingdom
Jacqui
The price is CA $108
CA $138 total
includes taxes & fees
Nov 2 - Nov 3
I Parigi Corbinelli
A water park with a pool, slides, and a wooden deck area.

18. hu Firenze Certosa camping in town

hu Firenze Certosa camping in town
Impruneta
8.4 out of 10, Very good, (108 reviews)
"Lovely location in the hills. Really nice pool and bar."
United Kingdom
Jessica
The price is CA $60
CA $71 total
includes taxes & fees
Oct 12 - Oct 13
hu Firenze Certosa camping in town
An open wooden door leading to an outdoor patio with a table and chairs.

19. 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 CA $150
CA $213 total
includes taxes & fees
Oct 4 - Oct 5
Palazzo al Torrione 2
A modern house with glass walls and a patio area.

20. Marignolle Relais and Charme

Marignolle Relais and Charme
Florence
9.2 out of 10, Wonderful, (93 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 CA $292
CA $340 total
includes taxes & fees
Oct 18 - Oct 19
Marignolle Relais and Charme
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Montespertoli Hotel Reviews

Villa Neroli

Villa Neroli

10/10 Excellent
"The property was magnificent - much nicer than what was depicted in the web photos. The staff was exceptional ... whether it was the administrative staff, the servers, or the cleaning staff, all realized that they were there to service their guests and they provided quality services consistently during our stay. The breakfast was exceptional. A very pleased guest!"
john 7-night trip
Posted 11 hours ago
Villa Neroli

Find out more about Montespertoli

Everything you need to know about Montespertoli vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Montespertoli vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Montespertoli vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Montespertoli vacation rentals we have selected for you start as low as CA $71 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 vacation 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 vacation.

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 vacation rental in Montespertoli?

Yes, we give you a choice of vacation rentals in Montespertoli close to Il Fiaschetto, or you can go with a more remote option if you want 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's the top vacation rental that Montespertoli has to offer?

Villa La Stella - Casa per Ferie: This vacation 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 vacation rental also comes with free parking to give you added peace of mind.

How many vacation rentals are there in Montespertoli?

Choose from 17 Expedia vacation rentals in Montespertoli for a memorable vacation.

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 vacation rentals like in Montespertoli?

Vacation rentals are privately owned properties you can stay in for several days or longer in Montespertoli. Vacation rentals provide amenities such as hot tubs, fire pits, and patios 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 security away from public hotel elevators and lobbies bustling with people while still allowing you to travel. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive choice for family trips or small group gatherings.