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

Montespertoli Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Jul 10 - Jul 12
In two months
Aug 21 - Aug 23
In three months
Sep 18 - Sep 20
In four months
Oct 16 - Oct 18

Our top choices for Montespertoli vacation rentals

Pool

Apartment for 2/3 guests with panoramic patio, pool and Wi-Fi

Apartment for 2/3 guests with panoramic patio, pool and Wi-Fi
Toscana
$252 nightly
The price is $256
Jul 23 - Jul 24
Total with taxes and fees
Apartment for 2/3 guests with panoramic patio, pool and Wi-Fi
Iron/ironing board, WiFi, bed sheets

Blueyes House Tuscany

Blueyes House Tuscany
Montespertoli
$164 nightly
The price is $167
Jun 29 - Jun 30
Total with taxes and fees
Blueyes House Tuscany
Property grounds

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

Villa Latini Agriturismo La Capanna

Villa Latini Agriturismo La Capanna
Montespertoli
Villa Latini Agriturismo La Capanna
Exterior

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, (23 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.
$417 nightly
The price is $421
Jul 1 - Jul 2
Total with taxes and fees
Tuscan Apart for 4/5 persons, WIFI, AIR-CO, SW-POOL, all comforts in the country
Pool

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.
$369 nightly
The price is $371
Jun 28 - Jun 29
Total with taxes and fees
Villa 'La Limonaia' with Shared Pool, Private Terrace & Wi-Fi
Outdoor dining

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.
$422 nightly
The price is $426
Jun 28 - Jun 29
Total with taxes and fees
Cozy apartment for 4/5 pax in a cottage in Chianti,Wifi,Swimmingpool,AIR-CO,Chef
Dining

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.
$2,254 nightly
The price is $2,256
Jul 2 - Jul 3
Total with taxes and fees
Villa Milani with Shared Pool, Private Terrace & Wi-Fi
Outdoor pool

Villa in the Florentine Chianti Region: 4 Bedrooms, Pool, and Views of the Hills

Villa in the Florentine Chianti Region: 4 Bedrooms, Pool, and Views of the Hills
Toscana
Villa in the Florentine Chianti Region: 4 Bedrooms, Pool, and Views of the Hills
Outdoor dining

Luxury Villa with Swimmingpool in Chianti/Sleeps 21 - or more in extra suites

Luxury Villa with Swimmingpool in Chianti/Sleeps 21 - or more in extra suites
Montespertoli
10.0 out of 10, Exceptional, (39 reviews)
"Excellent in every way. Highly recommend"
United States
Ed M.
$2,446 nightly
The price is $2,450
Jun 29 - Jun 30
Total with taxes and fees
Luxury Villa with Swimmingpool in Chianti/Sleeps 21 - or more in extra suites
Outdoor dining

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.
$2,205 nightly
The price is $2,209
Jun 29 - Jun 30
Total with taxes and fees
Luxury,Charming,in true Chianti, sleeps 22 or +/- pople., with AIR-CONDITION!!!!
Pool

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

Villa Il Frantoio with Shared Pool, Private Terrace & Wi-Fi
Montespertoli
$225 nightly
The price is $227
Jun 29 - Jun 30
Total with taxes and fees
Villa Il Frantoio with Shared Pool, Private Terrace & Wi-Fi
Pool

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

Villa 'Villa del Fattore' with Shared Pool, Private Terrace & Wi-Fi
Montespertoli
9.4 out of 10, Exceptional, (3 reviews)
"Beautiful stay in a wonderful Italian villa. "
United States
Jessica C.
$461 nightly
The price is $463
Jun 30 - Jul 1
Total with taxes and fees
Villa 'Villa del Fattore' with Shared Pool, Private Terrace & Wi-Fi
Pool

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.
$789 nightly
The price is $791
Jul 5 - Jul 6
Total with taxes and fees
Apartment 'La Terrazza' with Shared Pool, Private Terrace & Wi-Fi
Pool

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.
$738 nightly
The price is $740
Jun 28 - Jun 29
Total with taxes and fees
Apartment 'La Torre' with Shared Pool, Private Terrace & Wi-Fi
Property entrance

Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (100 reviews)
"This is a lovely gem. Includes parking which is hard to find. Family owned and its a truly beautiful place. Breakfast was amazing as well!! Recommend!! "
United States
rose
$228 nightly
The price is $255
Jul 5 - Jul 6
Total with taxes and fees
Villa il Fedino
Free daily buffet breakfast

Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (76 reviews)
"We had a wonderful experience! The staff was kind and very helpful. Our room was stunning and very spacious for a family of 5! The breakfast was amazing, and all of the activities on site were very fun - we especially enjoyed the cooking class! I would absolutely love to return here. I recommend looking into and booking on-site activities in advance so you can get the most out of your experience!"
United States
Julia
$297 nightly
The price is $332
Jun 28 - Jun 29
Total with taxes and fees
Terre di Baccio
Deluxe Double Room, City View | Room amenity

San Giuliano Inn - Adults Only

San Giuliano Inn - Adults Only
Historic Centre of Florence
10.0 out of 10, Exceptional, (436 reviews)
"This place was so beautiful and in a great location. The staff went above and beyond to make sure our stay was perfect. We were very happy with our choice of accommodations for our first time in Italy and it would be our choice when we return."
United States
TIFFANY
$167 nightly
The price is $197
Jul 27 - Jul 28
Total with taxes and fees
San Giuliano Inn - Adults Only
View from room

Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Barberino Tavarnelle
8.6 out of 10, Excellent, (115 reviews)
"Front desk was very helpful and very comfortable room. "
United States
Chris
$70 nightly
The price is $80
Jul 5 - Jul 6
Total with taxes and fees
Chianti Village Morrocco
Exterior

DomuS Miniato

DomuS Miniato
San Miniato
10.0 out of 10, Exceptional, (1 review)
"Kjempefint rom, nydelig utsikt og hyggelig vertsskap. Anbefales. "
Norway
Karen
$101 nightly
The price is $114
Jul 22 - Jul 23
Total with taxes and fees
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.
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

Art Hotel Villa Agape

Art Hotel Villa Agape

10/10 Excellent
"The hotel is beautiful and the staff was very friendly. My room was not as clean as expected."
Rey 3-night trip
Posted less than an hour ago
Art Hotel Villa Agape

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Montespertoli in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $57 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.

Explore a world of travel with Expedia

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. Another good choice for your trip to Montespertoli is House with character in typical medieval borgo on the Chianti Classico hills.

How many vacation rentals are there in Montespertoli?

Choose from 19 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. Uffizi Gallery and Piazza di Santa Maria Novella 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.