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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Montespertoli holiday rentals

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

1. Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (109 reviews)
"Food was amazing, we love how quiet and relaxing it was"
United States
Justyna
The price is 4.119.222 ₫
4.646.630 ₫ total
includes taxes & fees
6 Dec - 7 Dec
Villa il Fedino
An outdoor dining area with tables and chairs, covered by umbrellas, overlooking a scenic landscape.

2. B&B La Fonte del Machiavelli

B&B La Fonte del Machiavelli
San Casciano in Val di Pesa
9.2 out of 10, Wonderful, (94 reviews)
"The view is unique. Perfect location for a romantic trip."
United States
Stella
The price is 2.992.133 ₫
3.406.832 ₫ total
includes taxes & fees
6 Nov - 7 Nov
B&B La Fonte del Machiavelli
A spacious indoor area with arched windows, wooden furniture, and hanging plants.

3. Relais Villa Olmo - Place of Charme

Relais Villa Olmo - Place of Charme
Impruneta
9.6 out of 10, Exceptional, (275 reviews)
"Great property and staff. Highly recommend!"
United States
Michael
The price is 2.340.298 ₫
2.660.942 ₫ total
includes taxes & fees
23 Nov - 24 Nov
Relais Villa Olmo - Place of Charme
A water park with a pool, slides, and a wooden deck area.

4. hu Firenze Certosa camping in town

hu Firenze Certosa camping in town
Impruneta
8.6 out of 10, Excellent, (125 reviews)
"Very helpful staff and comfortable affordable stay"
United States
Ana María
The price is 1.240.160 ₫
1.450.790 ₫ total
includes taxes & fees
16 Nov - 17 Nov
hu Firenze Certosa camping in town
A modern house with glass walls and a patio area.

5. Marignolle Relais and Charme

Marignolle Relais and Charme
Florence
9.2 out of 10, Wonderful, (94 reviews)
"The Marignolle Relais & Charme is absolutely gorgeous. The rooms are beautifully decorated and everything is so clean. The grounds are well maintained and the pool area is stunning. We loved our two day stay and heartily recommend it. Stay here you’ll love it!!!"
Canada
Honey
The price is 3.356.844 ₫
4.039.382 ₫ total
includes taxes & fees
23 Nov - 24 Nov
Marignolle Relais and Charme
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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Find holiday rentals that suit your style

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Top Montespertoli Hotel Reviews

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

Villa La Cappella

Villa La Cappella
Montespertoli

10/10 Excellent

Our stay at Villa La Capella was nothing short of perfect. The two owners, Paula and Anthony, were both such incredible individuals. I have never experienced anything so warm and welcoming during my travels. The hospitality they provided went above and beyond what anyone would expect or could ask for. My partner and I will be returning again and again, if not for the most gorgeous views of the country side (or the beautiful and elegant Kobe, one of three resident dogs that live there) but for...
United Kingdom
ADAM
Reviewed April 24, 2026
Villa La Cappella

Frequently Asked Questions

Can I find a holiday rental in Montespertoli?

Yes, there are holiday rentals in Montespertoli close to Il Fiaschetto, or you can select a more secluded option if you're looking for 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.

How many holiday rentals are there in Montespertoli?

Choose from 17 Expedia holiday rentals in Montespertoli for a memorable holiday.

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 holiday rentals like in Montespertoli?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Montespertoli. Holiday rentals offer amenities like kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about a clean environment, holiday rentals can provide a sense of security away from public hotel lifts and busy lobbies while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive option for a small group gathering.