Photo by Paula Warren

Montespertoli Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • 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
In two months
In three months
In four months

Our top choices for Montespertoli vacation rentals

Townhouse in Barberino Tavarnelle

La Locanda di Pietracupa
9.4 out of 10, Exceptional, (35)
"Great place, wonderful restaurant"
Germany
Isabell
La Locanda di Pietracupa

Townhouse in San Gimignano City Centre

Palazzo al Torrione 2
9.2 out of 10, Wonderful, (107)
"Great location, beautiful room with a terrace and the best breakfast we had in Italy! "
United States
Angel
$122 nightly
The price is $140
Jan 19 - Jan 20, 2026
Total with taxes and fees
Palazzo al Torrione 2

Townhouse in Gambassi Terme

Tenuta Sant'Ilario
9.4 out of 10, Exceptional, (33)
"Amazing location and property! Owner and staff super nice! I am sure we will be back!"
Australia
Ilaria
Tenuta Sant'Ilario

Townhouse in Greve in Chianti

Terre di Baccio
9.8 out of 10, Exceptional, (71)
"The stay was great, and the staff were wonderful. "
United States
SYDNEY
$529 nightly
The price is $587
Dec 31 - Jan 1, 2026
Total with taxes and fees
Terre di Baccio

Residence in Historic Centre of Florence

Corte Guelfa
3.0 star property
9.8 out of 10, Exceptional, (160)
"Great location, attentive staff, clean rooms"
United States
Dennis
$129 nightly
The price is $157
Dec 28 - Dec 29
Total with taxes and fees
Corte Guelfa

Vacation Home in Historic Centre of Florence

QK Costa58 Home Tower
9.6 out of 10, Exceptional, (177)
"The building and room were very well maintained and clean. Nice quiet place to rest. Close to everything and we walked easily everywhere. Great place and location. Would stay there again. "
Canada
Nathan
$173 nightly
The price is $204
Dec 29 - Dec 30
Total with taxes and fees
QK Costa58 Home Tower

Townhouse in San Casciano in Val di Pesa

Villa il Fedino
9.6 out of 10, Exceptional, (97)
"Great people, great location great service"
Canada
James
$134 nightly
The price is $153
Jan 21 - Jan 22, 2026
Total with taxes and fees
Villa il Fedino

Residence in Barberino Tavarnelle

Chianti Village Morrocco
3.0 star property
8.6 out of 10, Excellent, (108)
"Spacious room in large resort style complex, set up as fully self contained with kitchen and dining furniture. Peaceful location with lovely views. Very pleasant staff and exceptional breakfast. "
France
Richard
$72 nightly
The price is $82
Jan 12 - Jan 13, 2026
Total with taxes and fees
Chianti Village Morrocco

Residence in Historic Centre of Florence

Palazzo Mannaioni Suites
4.0 star property
9.2 out of 10, Wonderful, (1073)
"Perfect stay"
United States
Juan P
$108 nightly
The price is $135
Jan 22 - Jan 23, 2026
Total with taxes and fees
Palazzo Mannaioni Suites

Apartment in Historic Centre of Florence

Numa Palazzo San Niccolò
9.4 out of 10, Exceptional, (175)
"Clean, amenities, breakfast! "
United States
Laury
$92 nightly
The price is $115
Jan 7 - Jan 8, 2026
Total with taxes and fees
Numa Palazzo San Niccolò

Residence in Historic Centre of Florence

La Torre Del Cestello
9.0 out of 10, Wonderful, (230)
"Great location and great rooms"
United States
David
$100 nightly
The price is $126
Jan 11 - Jan 12, 2026
Total with taxes and fees
La Torre Del Cestello

Residence in Historic Centre of Florence

Palazzo Vecchietti
10.0 out of 10, Exceptional, (82)
"Incredibly thoughtful and attentive staff. Beautiful property with tons of character and an exceptional location in Florence. Will definitely consider staying here again."
United States
Rajan
$489 nightly
The price is $554
Jan 19 - Jan 20, 2026
Total with taxes and fees
Palazzo Vecchietti

Residence in Historic Centre of Florence

Numa Florence Palazzo Belfiore
9.6 out of 10, Exceptional, (372)
"Great property, plenty of space for my family. The location is great, we were able to walk everywhere including the train station. "
United States
Loren
$182 nightly
The price is $214
Jan 11 - Jan 12, 2026
Total with taxes and fees
Numa Florence Palazzo Belfiore

Residence in Historic Centre of Florence

Tornabuoni Suites Collection
9.6 out of 10, Exceptional, (279)
"Beautiful Hotel in an amazing location. Very friendly and helpful staff. Room was large with an amazing balcony. Would definitely stay here again. "
United States
James W.
$183 nightly
The price is $215
Jan 11 - Jan 12, 2026
Total with taxes and fees
Tornabuoni Suites Collection

Aparthotel in Historic Centre of Florence

Bob W Florence Ponte Vecchio
9.2 out of 10, Wonderful, (211)
"Very nice, quiet area of Florence! You cannot ask for a better location within walking distance of so many famous tourist sites! "
United States
Denise
$109 nightly
The price is $134
Jan 16 - Jan 17, 2026
Total with taxes and fees
Bob W Florence Ponte Vecchio

Apartment in Historic Centre of Florence

Palazzo Branchi
9.0 out of 10, Wonderful, (287)
"WHAT A GREAT STAY. The location is perfect if you want to stay in the heart of Florence. Easy to reach all of the main attractions. The room was so pretty and spacious. Our host was very helpful, greeted us at the door, and had with great tips! Will stay here again. "
United States
Jeannette
$112 nightly
The price is $138
Jan 7 - Jan 8, 2026
Total with taxes and fees
Palazzo Branchi

Townhouse in Historic Centre of Florence

Residenza La Musa Amarcord
9.8 out of 10, Exceptional, (151)
"We liked our stay at this property. It’s a good value for the location, size, and style of the hotel. The staff was also very helpful and polite. I would stay here, again. "
United States
Fernando
Residenza La Musa Amarcord

Apartment in Historic Centre of Florence

Repubblica Firenze Luxury Apartments | UNA ESPERIENZE
9.6 out of 10, Exceptional, (79)
"Absolutely stunning views and a great property. Management friendly and helpful in the rare occasion you need something. I would absolutely stay here again. AC nice and cold, beautiful views, kitchenette area with stove top, refrigerator. Grazie!!!"
United States
Julie
$177 nightly
The price is $209
Jan 6 - Jan 7, 2026
Total with taxes and fees
Repubblica Firenze Luxury Apartments | UNA ESPERIENZE

Townhouse in Historic Centre of Florence

San Giuliano Inn - Adults Only
10.0 out of 10, Exceptional, (406)
"Great inn. "
United States
Carol
San Giuliano Inn - Adults Only

Townhouse in Historic Centre of Florence

Canto degli Scali
10.0 out of 10, Exceptional, (236)
"Amazing. Just incredible. Everyone should stay here when the come to Florence!"
Canada
Melissa
$177 nightly
The price is $209
Jan 7 - Jan 8, 2026
Total with taxes and fees
Canto degli Scali
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 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.

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?

QK Costa58 Home Tower: This vacation home rental outside of Montespertoli is located in the historical district and offers a terrace, air-conditioning, and daily housekeeping to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. 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 12 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. While here, Castello Sonnino and Montegufoni Castle are other places worth a visit.

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.