A sunlit landscape with a dirt path, rolling hills, and a misty valley.

Montespertoli Vacation 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.

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Dates

November 2026

December 2026

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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'

Montespertoli

￥28,517 total

includes taxes & fees

Nov 11 - Nov 12

An open doorway leading to an outdoor patio with a wooden table and chairs, a stone floor, and a wooden barrel with bottles.

2. 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.

￥57,193 total

includes taxes & fees

Nov 16 - Nov 17

A pink building with a wooden table and chairs, a window, and a door.

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

Montespertoli

￥49,591 total

includes taxes & fees

Nov 11 - Nov 12

A cozy living room with a fireplace, comfortable seating, and a television.

4. Tuscan Apart for 4/5 persons, WIFI, AIR-CO, SW-POOL, all comforts in the country

Montespertoli

Todd F.

￥54,174 total

includes taxes & fees

Nov 12 - Nov 13

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.

￥56,305 total

includes taxes & fees

Nov 18 - Nov 19

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

Montespertoli

Krista G.

￥251,332 total

includes taxes & fees

Dec 2 - Dec 3

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

Montespertoli

￥1,066,428 total

includes taxes & fees

Nov 15 - Nov 16

A room with a dining table, chairs, a chandelier, a painting, and a clock on a side table.

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

Montespertoli

Scott M.

￥288,099 total

includes taxes & fees

Nov 8 - Nov 9

9. 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.

￥335,523 total

includes taxes & fees

Nov 8 - Nov 9

A kitchen with wooden cabinets, a coffee machine, and a fruit basket.

10. SwimmingPool ONLY FOR YOU in Villa with AirCon for 26/30 pax in 13 bedrooms

Toscana

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

Montespertoli

Jessica C.

￥89,875 total

includes taxes & fees

Nov 6 - Nov 7

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

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

￥85,080 total

includes taxes & fees

Nov 11 - Nov 12

13. 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.

￥102,664 total

includes taxes & fees

Nov 11 - Nov 12

14. 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.

￥98,827 total

includes taxes & fees

Nov 11 - Nov 12

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

15. Villa il Fedino

San Casciano in Val di Pesa

Justyna

￥28,586 total

includes taxes & fees

Dec 5 - Dec 6

An outdoor dining area with tables and chairs, covered by umbrellas, overlooking a scenic landscape.

16. B&B La Fonte del Machiavelli

San Casciano in Val di Pesa

Stella

￥20,959 total

includes taxes & fees

Nov 9 - Nov 10

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

17. Relais Villa Olmo - Place of Charme

Impruneta

Michael

￥16,430 total

includes taxes & fees

Nov 22 - Nov 23

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

18. hu Firenze Certosa camping in town

Impruneta

Ana María

￥8,925 total

includes taxes & fees

Nov 16 - Nov 17

An outdoor patio with a table, chairs, and a view of a landscape.

19. country house with garden ,pool,children's play area ,Tuscany,15 from Florence

Toscana

Kim

￥25,754 total

includes taxes & fees

Nov 7 - Nov 8

An aerial view of a property with a swimming pool, surrounded by lush greenery and a well-maintained garden.

20. Marignolle Relais and Charme

Florence

Honey

￥24,864 total

includes taxes & fees

Nov 23 - Nov 24

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Find vacation rentals that suit your style

Top Montespertoli Hotel Reviews

A villa with a swimming pool, surrounded by well-maintained gardens and tall trees.

Villa La Cappella

Montespertoli

10/10 Excellent

Roger

A rural property with a swimming pool, a small house, and surrounding greenery.

Tenuta Moriano

Montespertoli

10/10 Excellent

We first stayed in Tenuta Moriano in 2005. We returned this summer for a 2nd stay. We were confused when we arrived as the resort was not the same. It was listed on Expedia as Tenuta Moriano but was actually a sister resort next door by the name of San Lorenzo. These are 2 different resorts and the listing did not mention that we were booking into the other one. Once we figured out where the resort was located we requested to see it and were informed that they would need to get this approved by...

Anonymous traveler

A formal garden with neatly trimmed hedges, a central fountain, and stone pathways.

Art Hotel Villa Agape - Place of Charme

Oltrarno

10/10 Excellent

Amazing in every way. The beauty of waking around is unlike any other. When we got there after a long day of traveling we had just missed the lunchtime to eat, and when went to shower the handle broke off- this is not a complaint. First they extended lunch without being asked and fixed the shower within minutes. From there on everything was amazing. Take time to eat the incredible breakfast in the garden, watch the breathtaking sunset in the back it’s incredible. Alessio- does it all he was...

John

A rooftop terrace with a table set for dining, candles, and a vase of flowers, overlooking a historic cityscape with notable architecture.

Hotel Santa Maria Novella

Historic Centre of Florence

10/10 Excellent

Nick

A dining area with a table set for two, a window with a view of historic buildings, and a chair with a cushion.

Hotel Pendini

Historic Centre of Florence

10/10 Excellent

William

A rooftop terrace with solar panels, outdoor seating, and a central sculpture.

The Social Hub Florence Belfiore

Santa Maria Novella

10/10 Excellent

Sanjana

A spacious living room with a large grey sofa, yellow armchairs, and a chandelier.

Hotel Horto Convento

Historic Centre of Florence

10/10 Excellent

Jassiel

A grand lobby with high ceilings, ornate columns, and a grand piano. Tables and chairs are arranged for guests.

Bernini Palace

Historic Centre of Florence

10/10 Excellent

Sarah

A garden pathway with white flowers and a glass structure overhead.

Hotel Orto de’ Medici

Historic Centre of Florence

10/10 Excellent

Christopher

The entrance to Hotel Spadaï Firenze with a modern design, including a reception desk and a chandelier.

Hotel Spadai

Historic Centre of Florence

10/10 Excellent

Richard

A large, multi-story building with a courtyard, surrounded by greenery and trees.

Villa Neroli - Place of Charme

Coverciano

10/10 Excellent

Chainarong

A neatly made bed with white linens, a pink upholstered headboard, and a bedside table with a lamp.

The Hoxton, Florence

Historic Centre of Florence

10/10 Excellent

Zevin

A table with breakfast items and a vase of flowers on a terrace overlooking a cityscape with historic buildings and a tower.

Hotel L'Orologio Firenze

Historic Centre of Florence

10/10 Excellent

Anonymous traveler

A modern hotel with a glass facade, a rooftop pool, and multiple balconies.

IQ Hotel Firenze

Historic Centre of Florence

10/10 Excellent

MUYUAN

Find out more about Montespertoli

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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 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.

Montespertoli Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Montespertoli vacation rentals

1. Holiday Home 'Blueyes house tuscany'

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

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

4. Tuscan Apart for 4/5 persons, WIFI, AIR-CO, SW-POOL, all comforts in the country

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

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

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

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

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

10. SwimmingPool ONLY FOR YOU in Villa with AirCon for 26/30 pax in 13 bedrooms

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

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

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

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

15. Villa il Fedino

16. B&B La Fonte del Machiavelli

17. Relais Villa Olmo - Place of Charme

18. hu Firenze Certosa camping in town

19. country house with garden ,pool,children's play area ,Tuscany,15 from Florence

20. Marignolle Relais and Charme

Find vacation rentals that suit your style

Top Montespertoli Hotel Reviews

Villa La Cappella

10/10 Excellent

Find out more about Montespertoli

Frequently Asked Questions

Can I find a vacation rental in Montespertoli?

What's the top vacation rental that Montespertoli has to offer?

How many vacation rentals are there in Montespertoli?

What’s there to see and do in Montespertoli?

What are vacation rentals like in Montespertoli?