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Montespertoli Vacation Rentals

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Our top choices for Montespertoli vacation rentals

B&B Palazzo Tortoli

B&B Palazzo Tortoli
San Gimignano City Centre
9.2 out of 10, Wonderful, (57)
"This is a great B&B its right in the heart of the town. The rooms are very clean and have historical character. The staff are so friendly and helpful. "
United States
April
$127 nightly
The price is $145
Jan 8 - Jan 9, 2026
Total with taxes and fees
B&B Palazzo Tortoli

Tenuta Sant'Ilario

Tenuta Sant'Ilario
Gambassi Terme
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

Palazzo al Torrione 2

Palazzo al Torrione 2
San Gimignano City Centre
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
$121 nightly
The price is $139
Jan 19 - Jan 20, 2026
Total with taxes and fees
Palazzo al Torrione 2

Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (71)
"The stay was great, and the staff were wonderful. "
United States
SYDNEY
$245 nightly
The price is $275
Jan 7 - Jan 8, 2026
Total with taxes and fees
Terre di Baccio

Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Barberino Tavarnelle
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
Chianti Village Morrocco

Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (97)
"Great people, great location great service"
Canada
James
$142 nightly
The price is $161
Jan 9 - Jan 10, 2026
Total with taxes and fees
Villa il Fedino

Corte Guelfa

Corte Guelfa
3.0 star property
Historic Centre of Florence
9.8 out of 10, Exceptional, (164)
"Great surrounding and vibe. Helpful staff."
Singapore
Soon Tiong
Corte Guelfa

Palazzo Mannaioni Suites

Palazzo Mannaioni Suites
4.0 star property
Historic Centre of Florence
9.2 out of 10, Wonderful, (1075)
"Perfect stay"
United States
Juan P
$105 nightly
The price is $132
Jan 26 - Jan 27, 2026
Total with taxes and fees
Palazzo Mannaioni Suites

La Torre Del Cestello

La Torre Del Cestello
Historic Centre of Florence
9.0 out of 10, Wonderful, (231)
"Great location and great rooms"
United States
David
$81 nightly
The price is $106
Jan 7 - Jan 8, 2026
Total with taxes and fees
La Torre Del Cestello

Numa Palazzo San Niccolò

Numa Palazzo San Niccolò
Historic Centre of Florence
9.4 out of 10, Exceptional, (176)
"Great stay . Super location"
United States
Kedar
$92 nightly
The price is $115
Jan 7 - Jan 8, 2026
Total with taxes and fees
Numa Palazzo San Niccolò

Sette Angeli Rooms

Sette Angeli Rooms
Historic Centre of Florence
8.8 out of 10, Excellent, (636)
"I loved this place and the stuff was very kind <3 "
United Kingdom
romina
$75 nightly
The price is $97
Jan 5 - Jan 6, 2026
Total with taxes and fees
Sette Angeli Rooms

Residenza La Musa Amarcord

Residenza La Musa Amarcord
Historic Centre of Florence
9.8 out of 10, Exceptional, (153)
"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
$93 nightly
The price is $117
Jan 8 - Jan 9, 2026
Total with taxes and fees
Residenza La Musa Amarcord

Numa Florence Palazzo Belfiore

Numa Florence Palazzo Belfiore
Historic Centre of Florence
9.6 out of 10, Exceptional, (374)
"Very spacious and clean stay with premium proximity to the city"
United States
Raehmojhzn
$168 nightly
The price is $199
Jan 11 - Jan 12, 2026
Total with taxes and fees
Numa Florence Palazzo Belfiore

Tornabuoni Suites Collection

Tornabuoni Suites Collection
Historic Centre of Florence
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.
$178 nightly
The price is $210
Jan 18 - Jan 19, 2026
Total with taxes and fees
Tornabuoni Suites Collection

Palazzo Branchi

Palazzo Branchi
Historic Centre of Florence
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
$103 nightly
The price is $128
Jan 8 - Jan 9, 2026
Total with taxes and fees
Palazzo Branchi

Bob W Florence Ponte Vecchio

Bob W Florence Ponte Vecchio
Historic Centre of Florence
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
$101 nightly
The price is $125
Jan 20 - Jan 21, 2026
Total with taxes and fees
Bob W Florence Ponte Vecchio

Repubblica Firenze Luxury Apartments | UNA ESPERIENZE

Repubblica Firenze Luxury Apartments | UNA ESPERIENZE
Historic Centre of Florence
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

San Giuliano Inn - Adults Only

San Giuliano Inn - Adults Only
Historic Centre of Florence
10.0 out of 10, Exceptional, (406)
"Great inn. "
United States
Carol
$105 nightly
The price is $130
Jan 8 - Jan 9, 2026
Total with taxes and fees
San Giuliano Inn - Adults Only

Cosy House

Cosy House
Historic Centre of Florence
8.6 out of 10, Excellent, (134)
"Great location and little Bonus to have continental breakfast included "
United States
Michelle
$104 nightly
The price is $128
Jan 7 - Jan 8, 2026
Total with taxes and fees
Cosy House

Canto degli Scali

Canto degli Scali
Historic Centre of Florence
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 6 - Jan 7, 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.
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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?

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 14 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, Montegufoni Castle and Castello Sonnino 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.