Montespertoli Vacation Rentals from $53: Search Short-Term Rentals

Q: 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.

Check prices for these dates

In two weeks

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Our top choices for Montespertoli vacation 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

Montespertoli

$164 nightly

Sep 27 - Sep 28

Total with taxes and fees

A modern bedroom with a bed, bedside tables, a chair, a TV, and a view of the outdoors.

2. Holiday Home 'Blueyes house tuscany'

Montespertoli

$158 nightly

Sep 30 - Oct 1

Total with taxes and fees

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

Montespertoli

$6,834 nightly

Oct 14 - Oct 15

Total with taxes and fees

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

Montespertoli

"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!"

Susan A.

$447 nightly

Oct 19 - Oct 20

Total with taxes and fees

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

Poppiano

"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...

Dinah H.

$420 nightly

Oct 3 - Oct 4

Total with taxes and fees

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

Montespertoli

Mark S.

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

7. Villa Milani with Shared Pool, Private Terrace & Wi-Fi

Montespertoli

Scott M.

$2,253 nightly

Sep 30 - Oct 1

Total with taxes and fees

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

Montespertoli

"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!"

Elise D.

$2,131 nightly

Oct 19 - Oct 20

Total with taxes and fees

9. Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites

Montespertoli

Krista G.

$2,014 nightly

Sep 28 - Sep 29

Total with taxes and fees

A swimming pool with lounge chairs and tables, surrounded by grass and a view of hills.

10. Villa 'La Limonaia' with Shared Pool, Private Terrace & Wi-Fi

Montespertoli

"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...

Anonymous traveler

$492 nightly

Sep 28 - Sep 29

Total with taxes and fees

A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a view of rolling hills.

11. Apartment 'La Terrazza' with Shared Pool, Private Terrace & Wi-Fi

Montespertoli

"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."

Charlie B.

$655 nightly

Oct 8 - Oct 9

Total with taxes and fees

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

Montespertoli

Jessica C.

$573 nightly

Oct 9 - Oct 10

Total with taxes and fees

13. Apartment 'La Torre' with Shared Pool, Private Terrace & Wi-Fi

Montespertoli

"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...

Havva C.

$632 nightly

Oct 1 - Oct 2

Total with taxes and fees

An arched entrance with a lantern above, flanked by two potted plants.

14. Villa il Fedino

San Casciano in Val di Pesa

Lori

$217 nightly

Oct 25 - Oct 26

Total with taxes and fees

A spacious indoor area with arched windows, wooden furniture, and hanging plants.

15. Relais Villa Olmo

Impruneta

Mohamed

$166 nightly

Oct 11 - Oct 12

Total with taxes and fees

A water park with a pool, slides, and a wooden deck area.

16. hu Firenze Certosa camping in town

Impruneta

Jessica

$45 nightly

Oct 12 - Oct 13

Total with taxes and fees

A room with a dining table, a vase of flowers, a lamp, and a view of a historic building through a window.

17. Mamo Florence - Le Farine Della Signoria Apartments

Historic Centre of Florence

Karl

$212 nightly

Oct 25 - Oct 26

Total with taxes and fees

An open wooden door leading to an outdoor patio with a table and chairs.

18. Palazzo al Torrione 2

San Gimignano City Centre

Angela

$131 nightly

Oct 27 - Oct 28

Total with taxes and fees

A view from a window overlooking a rural landscape with fields and a distant mountain range.

19. B&B Palazzo Tortoli

San Gimignano City Centre

Harold

$130 nightly

Oct 18 - Oct 19

Total with taxes and fees

A narrow alleyway with brick walls, wooden barrels, and potted plants.

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

San Gimignano City Centre

Marilyn H.

$167 nightly

Sep 29 - Sep 30

Total with taxes and fees

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Top Montespertoli Hotel Reviews

Hotel Paris

10/10 Excellent

"I chose this hotel based on its convenient location to the area attractions. I was delighted by the historic aspects of the property. There was a good variety of food at the breakfast. The staff was amazing and the room was comfortable. We had a great city view."

c-hotels Ambasciatori

8/10 Good

"The hotel Is nice and very centrally located rooms are small and the biggest problem is the shower is like a capsule of 3.5’x3.5’ i which you can hardly move without hitting yourselves everywhere Honestly I have never been a hotel with a shower that small Hotel breakfast was really good Thanks Jose"

Villa Neroli

8/10 Good

"The buffet breakfast had every option to be desired. Staff was helpful. Hotel is situated in a quiet area. If you’re coming from the US don’t forget a plug adapter AND step down transformer. There is a bus stop close by to get into the city or most things are a 30-60 minute walk. Irons are not in the rooms but in a designated area or available upon request."

Plus Florence - Hostel

10/10 Excellent

"The rooms were very clean and fresh towels were brought often! The common areas were clean and well maintained. The only thing I wish was there were hooks in both bathrooms (especially the shower) so I could hang my towel and clothes and not have to put them on the floor or the sink. Other than that I would stay again!"

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 $53 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.

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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 16 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.

Montespertoli Vacation Rentals

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Check prices for these dates

Our top choices for Montespertoli vacation rentals

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

2. Holiday Home 'Blueyes house tuscany'

3. Villa with Guesthouse: Private Pool, Air Conditioning, 13 Bedrooms for up to 30 Guests

4. Tuscan Farmhouse with Private Pool & Chianti Vineyard Views - 3 Bedr + AC

5. Cozy apartment for 4/5 pax in a cottage in Chianti,Wifi,Swimmingpool,AIR-CO,Chef

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

7. Villa Milani with Shared Pool, Private Terrace & Wi-Fi

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

9. Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites

10. Villa 'La Limonaia' with Shared Pool, Private Terrace & Wi-Fi

11. Apartment 'La Terrazza' with Shared Pool, Private Terrace & Wi-Fi

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

13. Apartment 'La Torre' with Shared Pool, Private Terrace & Wi-Fi

14. Villa il Fedino

15. Relais Villa Olmo

16. hu Firenze Certosa camping in town

17. Mamo Florence - Le Farine Della Signoria Apartments

18. Palazzo al Torrione 2

19. B&B Palazzo Tortoli

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

Find vacation rentals that suit your style

Top Montespertoli Hotel Reviews

Hotel Paris

Find out more about Montespertoli

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