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Check prices for these dates

Next weekend
1 Aug - 3 Aug
In two weeks
8 Aug - 10 Aug
In one month
22 Aug - 24 Aug
In two months
19 Sept - 21 Sept

Featured Villas in Montespertoli

Relais Badia a Passignano
Aerial view

Relais Badia a Passignano

10.0 out of 10, Exceptional, (1)
Relais Badia a Passignano
Villa in Poggiarello-ripa with 3 bedrooms sleeps 5
Relax in a serene outdoor space with a lush landscape view, a pool, and comfortable seating.

Villa in Poggiarello-ripa with 3 bedrooms sleeps 5

10.0 out of 10, Exceptional, (109)
"We had a large group of family and friends comfortably stay here. The host was very available and helpful, and personally showed us around the property upon our arrival. The property description is accurate. "
Villa in Poggiarello-ripa with 3 bedrooms sleeps 5
Exclusive Villa 20 minutes to Florence center w/ heated pool & Concierge service
Stunning stone building with a large arched doorway and windows, set amidst a charming entrance.

Exclusive Villa 20 minutes to Florence center w/ heated pool & Concierge service

10.0 out of 10, Exceptional, (102)
"The villa is absolutely stunning & our stay was an amazing experience. We had a small wedding ceremony with our guests followed by a home cooked Italian dinner which was the most perfect evening. Cate & her family were very accommodating and made us feel very welcome. Cate made our stay stress-free and was more than happy to help organise anything we may have needed for our stay. I can’t wait to stay again "
The price is NZ$3,275
includes taxes & fees
31 July - 1 Aug
Exclusive Villa 20 minutes to Florence center w/ heated pool & Concierge service
Villa Sarah Luxury Villa a San Gimignano 5 room en suite swimming pool spa
Relax beneath the pergola's shade, surrounded by lush greenery and a serene pool.

Villa Sarah Luxury Villa a San Gimignano 5 room en suite swimming pool spa

10.0 out of 10, Exceptional, (42)
"Great Villa to stay at. Owner was excellent to deal with."
Villa Sarah Luxury Villa a San Gimignano 5 room en suite swimming pool spa
Villa Le Balze Large Private Pool, WiFi
Relax in a Mediterranean-style villa surrounded by lush greenery and scenic views.

Villa Le Balze Large Private Pool, WiFi

9.8 out of 10, Exceptional, (17)
"An excellent choice for a worry-free and comfortable stay."
Villa Le Balze Large Private Pool, WiFi
Villa Poggio Scalette: Elegance meets comfort amidst the olive trees
Outdoor pool

Villa Poggio Scalette: Elegance meets comfort amidst the olive trees

10.0 out of 10, Exceptional, (8)
"Villa Poggio Scalette was truly a dream place to stay on our vacation. The pictures cannot do this beautiful home justice - you have to see it for yourself!! The view, the amazing property, the Tuscan touches in the decorating with all the modern amenities - we already cannot wait to go back!!! We slept so comfortably and had everything we needed at the house for some relaxing afternoons and evenings enjoying wine, good food, and the view :) Our host Simone was very communicative and so helpful...
Villa Poggio Scalette: Elegance meets comfort amidst the olive trees
Tenuta Lo Spugno, Radda in Chianti, Siena and Chianti
Relax by the serene pool surrounded by lush greenery and a picturesque hillside.

Tenuta Lo Spugno, Radda in Chianti, Siena and Chianti

Tenuta Lo Spugno, Radda in Chianti, Siena and Chianti
15th century barn fully renovated in a stylish style with gorgeous swimming pool
Relax in style on the patio, surrounded by lush views and a refreshing pool.

15th century barn fully renovated in a stylish style with gorgeous swimming pool

9.2 out of 10, Wonderful, (10)
"We were two couples looking for an authentic Tuscan experience in the gorgeous countryside. The location is well suited to travel to Montalpucino, Chianti, San Gimignano, Volterra, Pisa and Florence. Both Mido and David were very attentive towards making our visit comfortable . A gorgeous building with high quality style and finishes. A top contender for best vrbo property I have ever visited. Thank you!"
15th century barn fully renovated in a stylish style with gorgeous swimming pool
Villa Salivolpe - on top of a Chianti hill - Private swimming pool
Relax by the serene pool surrounded by lush greenery and olive trees.

Villa Salivolpe - on top of a Chianti hill - Private swimming pool

9.6 out of 10, Exceptional, (22)
"The villa was a beautiful home to send our our time in Tuscany, Italy. We enjoyed having our own bedrooms and baths. We had a special meal cooked by a local chef, Rachel. The kitchen worked well for the cooking, and for our breakfasts. The scenery was just breathtaking, and it is just as pictures in books looked like. We very much enjoyed our stay."
Villa Salivolpe - on top of a Chianti hill - Private swimming pool
Historic Villa Tuscany
Cozy attic bedroom with a television, framed portrait, and comfortable seating area.

Historic Villa Tuscany

2.0 out of 10, (2)
The price is NZ$278
includes taxes & fees
3 Aug - 4 Aug
Historic Villa Tuscany
Alfresco Splendid Panoramic Villa with private heatable pool and jacuzzi
Stunning facade with a central entrance and symmetrical wings, surrounded by manicured hedges and a gravel pathway.

Alfresco Splendid Panoramic Villa with private heatable pool and jacuzzi

9.6 out of 10, Exceptional, (15)
"Excellent experience, an amazing villa and great host! 100% recommend!"
Alfresco Splendid Panoramic Villa with private heatable pool and jacuzzi
Private villa in the heart of chianti with view of siena
Relax by the serene pool surrounded by lounge chairs and tables under a large tree.

Private villa in the heart of chianti with view of siena

10.0 out of 10, Exceptional, (1)
"Fantastiskt boende med underbar trädgård och utsikt, nära vingårdar och historiska städer!"
Private villa in the heart of chianti with view of siena
Your panoramic house in Tuscany between vineyards and olive groves.
Surrounded by lush greenery and vineyards, this house offers a tranquil environment.

Your panoramic house in Tuscany between vineyards and olive groves.

9.8 out of 10, Exceptional, (38)
"We had such a nice stay and only wish it had been longer! Enrico & Simona were excellent hosts and we loved the cooking class they did for us and our 3 college students who learned to make pasta for the first time. The views are spectacular and it’s a perfect location for trips to the many surrounding towns and wineries. We’d love to come back in the summer and stay longer!"
Your panoramic house in Tuscany between vineyards and olive groves.
Quiet and Beautiful Property, Large Pool, Airco in bedrooms
Standalone residence with a traditional Mediterranean architectural style, surrounded by lush greenery.

Quiet and Beautiful Property, Large Pool, Airco in bedrooms

10.0 out of 10, Exceptional, (53)
"The house was fantastic and had more than enough space for our large family. What was particularly great was the large table where we always ate before we went to the very large swimming pool."
Quiet and Beautiful Property, Large Pool, Airco in bedrooms
Charming Villa Torre in Chianti, 8 ensuite bedrooms, pool, Florence, Wi-Fi, A/C.
Relax by the serene pool surrounded by lush greenery and flowering plants, with lounge chairs for ultimate relaxation.

Charming Villa Torre in Chianti, 8 ensuite bedrooms, pool, Florence, Wi-Fi, A/C.

10.0 out of 10, Exceptional, (113)
"It was a great experience. The villa was perfect. Hosts were amazing. "
Charming Villa Torre in Chianti, 8 ensuite bedrooms, pool, Florence, Wi-Fi, A/C.
LUXURY VILLA WITH PRIVATE POOL
Relax by the serene pool surrounded by lush greenery and rolling hills.

LUXURY VILLA WITH PRIVATE POOL

10.0 out of 10, Exceptional, (10)
"Everything was even better than expected. Plumbing issues did arise and should be addressed. We loved our stay and would recommend it highly to others"
LUXURY VILLA WITH PRIVATE POOL
Exclusive Farmhouse Pool & View of San Gimignano
Enjoy a romantic dinner for two in this charming outdoor dining area with a round table and wicker chairs.

Exclusive Farmhouse Pool & View of San Gimignano

10.0 out of 10, Exceptional, (1)
Exclusive Farmhouse Pool & View of San Gimignano
Villa Franchetti - Luxurious Florentine Villa with Swimming Pool
Stately building with a classical facade, featuring a central entrance and manicured gardens.

Villa Franchetti - Luxurious Florentine Villa with Swimming Pool

10.0 out of 10, Exceptional, (14)
"We enjoyed this beautiful property It was just like in the pictures!!! Everything worked perfect"
Villa Franchetti - Luxurious Florentine Villa with Swimming Pool
Villa "Le Vallecchie" overlooking Siena and with private swimming pool
Guests can relax on the outdoor bench amidst a serene garden with flowering plants and a tree.

Villa "Le Vallecchie" overlooking Siena and with private swimming pool

9.6 out of 10, Exceptional, (33)
"Really enjoyed our stay. A great place to relax."
Villa "Le Vallecchie" overlooking Siena and with private swimming pool
4-bedroom stonehouse with stunning pool in the Chianti countryside with WiFi, AC
Relax by the pool with comfortable lounge chairs and a wicker basket for your essentials.

4-bedroom stonehouse with stunning pool in the Chianti countryside with WiFi, AC

8.0 out of 10, Very good, (1)
"We spent a great family time at Adme’s house.The house has everything. Was very clean and well maintained . Will highly recommend."
4-bedroom stonehouse with stunning pool in the Chianti countryside with WiFi, AC
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

Hu Firenze Camping In Town

Hu Firenze Camping In Town

10/10 Excellent
"Love it "
Nataliya 1-night trip
Posted 20 hours ago
Hu Firenze Camping In Town

Frequently asked questions

How much do villas in Montespertoli cost?
You'll pay between NZ$278 and NZ$3,275 per night for a villa in Montespertoli. Whatever your budget, a fantastic stay is just a click or two away on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many villas are there in Montespertoli?
Pick from 1838 villas in Montespertoli. Whether you're taking a trip with the little ones or planning a weekend escape with some friends, Expedia can help you find the right space for your squad.
What is there to do near my villa in Montespertoli?
There are loads of fantastic things to sink your teeth into in Montespertoli. Drop by popular attractions like Vine and Wine Museum, Castle of Poppiano and Montespertoli City Hall. Piazza Machiavelli, Azienda Agricola Ammirabile and Montegufoni Castle also lure many visitors.