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Villas San Casciano Val di Pesa to rent

We have 18 properties to choose from.
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  • Price per night

    • Up to £100
    • £100 - £199
    • From £200

  • Accommodation types

    • House
    • Apartment
    • Farmhouse

  • Rating

    • 4.5+
    • 4+

  • Services

    • Pool
    • WiFi
    • Kitchen
    • Washing machine
    • Air conditioning
    • Parking
    • Balcony/patio
    • TV
    • Garden
    • Dishwasher
    • Fireplace
    • Microwave
    • Hot tub
    • Cot
    Show more

  • Accommodation type

    • Pet-friendly
    • No smoking
    • No pets

  • Activities

    • Grill
House San Casciano in Val di Pesa
40 m² house ∙ 4 guests ∙ 2 bedrooms

House Badia a Passignano

San Casciano in Val di Pesa, Metropolitan City of Florence, Italy
from £78
per night
4.3
Very good
(18 ratings)
from £78
per night
View deal
House San Casciano in Val di Pesa
140 m² house ∙ 6 guests ∙ 3 bedrooms

House Il Casale

San Casciano in Val di Pesa, Metropolitan City of Florence, Italy
from £78
per night
4.8
Outstanding
(83 ratings)
from £78
per night
View deal
House San Casciano in Val di Pesa
220 m² house ∙ 8 guests ∙ 4 bedrooms

House Ambrogetta

San Casciano in Val di Pesa, Metropolitan City of Florence, Italy
from £220
per night
4.8
Outstanding
(95 ratings)
from £220
per night
View deal
House San Casciano in Val di Pesa
80 m² house ∙ 3 guests ∙ 2 bedrooms

House Cipereto

San Casciano in Val di Pesa, Metropolitan City of Florence, Italy
from £135
per night
4.5
Excellent
(2 ratings)
from £135
per night
View deal
House San Casciano in Val di Pesa
195 m² house ∙ 8 guests ∙ 4 bedrooms

House Sole

San Casciano in Val di Pesa, Metropolitan City of Florence, Italy
from £249
per night
5.0
Outstanding
(9 ratings)
from £249
per night
View deal
House San Casciano in Val di Pesa
200 m² house ∙ 10 guests ∙ 5 bedrooms

House Il Poggetto

San Casciano in Val di Pesa, Metropolitan City of Florence, Italy
from £205
per night
4.4
Very good
(59 ratings)
from £205
per night
View deal
Apartment San Casciano in Val di Pesa
100 m² apartment ∙ 6 guests ∙ 3 bedrooms

Apartment Il Convento

San Casciano in Val di Pesa, Metropolitan City of Florence, Italy
from £83
per night
4.6
Excellent
(28 ratings)
from £83
per night
View deal
House San Casciano in Val di Pesa
270 m² house ∙ 12 guests ∙ 6 bedrooms

House Erta Toskanisches Bauernhaus mit Pool

San Casciano in Val di Pesa, Metropolitan City of Florence, Italy
from £464
per night
5.0
Outstanding
(4 ratings)
from £464
per night
View deal
Apartment San Casciano in Val di Pesa
94 m² apartment ∙ 6 guests ∙ 2 bedrooms

Apartment Matteuzzi

San Casciano in Val di Pesa, Metropolitan City of Florence, Italy
from £56
per night
4.6
Excellent
(42 ratings)
from £56
per night
View deal
Apartment San Casciano in Val di Pesa
52 m² apartment ∙ 2 guests ∙ 1 bedroom

Apartment Casa Fallocchio

San Casciano in Val di Pesa, Metropolitan City of Florence, Italy
from £136
per night
5.0
Outstanding
(2 ratings)
from £136
per night
View deal
House San Casciano in Val di Pesa
390 m² house ∙ 12 guests ∙ 6 bedrooms

House Bulleri

San Casciano in Val di Pesa, Metropolitan City of Florence, Italy
from £292
per night
3.9
Good
(39 ratings)
from £292
per night
View deal
House San Casciano in Val di Pesa
270 m² house ∙ 12 guests ∙ 6 bedrooms

House Freistehendes Bauernhaus

San Casciano in Val di Pesa, Metropolitan City of Florence, Italy
from £478
per night
from £478
per night
View deal
House San Casciano in Val di Pesa
350 m² house ∙ 12 guests ∙ 6 bedrooms

House Casa delle Fiabe

San Casciano in Val di Pesa, Metropolitan City of Florence, Italy
from £280
per night
4.4
Very good
(70 ratings)
from £280
per night
View deal
Apartment San Casciano in Val di Pesa
55 m² apartment ∙ 2 guests ∙ 1 bedroom

Apartment Casa Fallocchio

San Casciano in Val di Pesa, Metropolitan City of Florence, Italy
from £136
per night
4.0
Very good
(1 rating)
from £136
per night
View deal
Apartment San Casciano in Val di Pesa
120 m² apartment ∙ 3 guests ∙ 3 bedrooms

Apartment Wohnung mit Poolbenutzung

San Casciano in Val di Pesa, Metropolitan City of Florence, Italy
from £208
per night
5.0
Outstanding
(2 ratings)
from £208
per night
View deal
House San Casciano in Val di Pesa
230 m² house ∙ 9 guests ∙ 5 bedrooms

House Villa il Giglio

San Casciano in Val di Pesa, Metropolitan City of Florence, Italy
from £195
per night
5.0
Outstanding
(4 ratings)
from £195
per night
View deal

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House San Casciano in Val di Pesa
110 m² house ∙ 6 guests ∙ 2 bedrooms

House La Vecchia Pieve

San Casciano in Val di Pesa, Metropolitan City of Florence, Italy
from £115
per night
from £115
per night
View deal
House San Casciano in Val di Pesa
100 m² house ∙ 6 guests ∙ 3 bedrooms

House Casa Fitzy

San Casciano in Val di Pesa, Metropolitan City of Florence, Italy
from £100
per night
4.6
Excellent
(36 ratings)
from £100
per night
View deal
House San Casciano in Val di Pesa
210 m² house ∙ 12 guests ∙ 6 bedrooms

House Reggine

San Casciano in Val di Pesa, Metropolitan City of Florence, Italy
from £223
per night
4.8
Outstanding
(18 ratings)
from £223
per night
View deal
House San Casciano in Val di Pesa
80 m² house ∙ 6 guests ∙ 2 bedrooms

House Linearis J

San Casciano in Val di Pesa, Metropolitan City of Florence, Italy
from £138
per night
4.7
Excellent
(6 ratings)
from £138
per night
View deal
House San Casciano in Val di Pesa
95 m² house ∙ 6 guests ∙ 3 bedrooms

House Lucolena

San Casciano in Val di Pesa, Metropolitan City of Florence, Italy
from £122
per night
4.7
Excellent
(65 ratings)
from £122
per night
View deal
House San Casciano in Val di Pesa
65 m² house ∙ 5 guests ∙ 2 bedrooms

House San Rocco

San Casciano in Val di Pesa, Metropolitan City of Florence, Italy
from £82
per night
3.8
Good
(30 ratings)
from £82
per night
View deal
House San Casciano in Val di Pesa
65 m² house ∙ 4 guests ∙ 2 bedrooms

House Chiesa

San Casciano in Val di Pesa, Metropolitan City of Florence, Italy
from £66
per night
4.4
Very good
(24 ratings)
from £66
per night
View deal
House San Casciano in Val di Pesa
72 m² house ∙ 6 guests ∙ 2 bedrooms

House L' Ulivo

San Casciano in Val di Pesa, Metropolitan City of Florence, Italy
from £79
per night
4.6
Excellent
(60 ratings)
from £79
per night
View deal
House San Casciano in Val di Pesa
65 m² house ∙ 4 guests ∙ 2 bedrooms

House Capella

San Casciano in Val di Pesa, Metropolitan City of Florence, Italy
from £63
per night
4.6
Excellent
(53 ratings)
from £63
per night
View deal
House San Casciano in Val di Pesa
70 m² house ∙ 5 guests ∙ 2 bedrooms

House Il Casino

San Casciano in Val di Pesa, Metropolitan City of Florence, Italy
from £72
per night
4.3
Very good
(32 ratings)
from £72
per night
View deal
House San Casciano in Val di Pesa
140 m² house ∙ 6 guests ∙ 2 bedrooms

House Decameron house

San Casciano in Val di Pesa, Metropolitan City of Florence, Italy
from £99
per night
3.8
Good
(13 ratings)
from £99
per night
View deal
House San Casciano in Val di Pesa
150 m² house ∙ 8 guests ∙ 4 bedrooms

House Campiglia

San Casciano in Val di Pesa, Metropolitan City of Florence, Italy
from £206
per night
4.4
Very good
(60 ratings)
from £206
per night
View deal
House San Casciano in Val di Pesa
110 m² house ∙ 8 guests ∙ 4 bedrooms

House Pilar

San Casciano in Val di Pesa, Metropolitan City of Florence, Italy
from £270
per night
5.0
Outstanding
(2 ratings)
from £270
per night
View deal
House San Casciano in Val di Pesa
140 m² house ∙ 6 guests ∙ 3 bedrooms

House Il Casolarino

San Casciano in Val di Pesa, Metropolitan City of Florence, Italy
from £256
per night
4.8
Outstanding
(34 ratings)
from £256
per night
View deal
Apartment San Casciano in Val di Pesa
70 m² apartment ∙ 4 guests ∙ 2 bedrooms

Apartment Petrarca

San Casciano in Val di Pesa, Metropolitan City of Florence, Italy
from £98
per night
4.8
Outstanding
(57 ratings)
from £98
per night
View deal
Apartment San Casciano in Val di Pesa
50 m² apartment ∙ 4 guests ∙ 1 bedroom

Apartment Podere La Torre

San Casciano in Val di Pesa, Metropolitan City of Florence, Italy
from £73
per night
4.9
Outstanding
(49 ratings)
from £73
per night
View deal
House San Casciano in Val di Pesa
70 m² house ∙ 4 guests ∙ 2 bedrooms

House Vignole

San Casciano in Val di Pesa, Metropolitan City of Florence, Italy
from £81
per night
4.9
Outstanding
(53 ratings)
from £81
per night
View deal
House San Casciano in Val di Pesa
80 m² house ∙ 6 guests ∙ 2 bedrooms

House Il Sorriso

San Casciano in Val di Pesa, Metropolitan City of Florence, Italy
from £82
per night
5.0
Outstanding
(28 ratings)
from £82
per night
View deal
Apartment San Casciano in Val di Pesa
88 m² apartment ∙ 4 guests ∙ 1 bedroom

Apartment Il Poggio

San Casciano in Val di Pesa, Metropolitan City of Florence, Italy
from £65
per night
4.5
Excellent
(77 ratings)
from £65
per night
View deal
House San Casciano in Val di Pesa
55 m² house ∙ 4 guests ∙ 1 bedroom

House Il Poderino

San Casciano in Val di Pesa, Metropolitan City of Florence, Italy
from £40
per night
4.0
Very good
(23 ratings)
from £40
per night
View deal
House San Casciano in Val di Pesa
120 m² house ∙ 6 guests ∙ 2 bedrooms

House Il Vallone

San Casciano in Val di Pesa, Metropolitan City of Florence, Italy
from £113
per night
4.7
Excellent
(54 ratings)
from £113
per night
View deal
Apartment San Casciano in Val di Pesa
70 m² apartment ∙ 5 guests ∙ 2 bedrooms

Apartment Ciliegio

San Casciano in Val di Pesa, Metropolitan City of Florence, Italy
from £75
per night
4.9
Outstanding
(68 ratings)
from £75
per night
View deal
House San Casciano in Val di Pesa
50 m² house ∙ 4 guests ∙ 2 bedrooms

House Casa Patrizia

San Casciano in Val di Pesa, Metropolitan City of Florence, Italy
from £65
per night
4.5
Excellent
(14 ratings)
from £65
per night
View deal
House San Casciano in Val di Pesa
250 m² house ∙ 8 guests ∙ 3 bedrooms

House Casa Mori

San Casciano in Val di Pesa, Metropolitan City of Florence, Italy
from £135
per night
4.9
Outstanding
(77 ratings)
from £135
per night
View deal

Customer reviews San Casciano in Val di Pesa

Based on 22 ratings

This house is amazing! Everything was just perfect and we absolutely loved our stay. The location is well suited to visit all the towns in Tuscany. The town of San Casciano is only 6 min drive and has great facilities. The house is spacious and very comfortable. The views are spectacular. B. was the most wonderful host - it felt like we were old friends. I would highly recommend this house.

Trent

Reviewed on 09/10/2025

We enjoyed a very comfortable and charming stay at this cottage (lower level of home). On arrival we were greeted with a lemon cake and bottle of wine (both homemade). The hosts were always ready to help out if we were stumped by something such as the gas stove. The kitchen was well equipped for cooking or eating at home. When we had some trouble finding the place, the host responded immediately with a google map. We highly recommend this rental as an excellent value.

Barbara

Reviewed on 03/10/2025

Four of us stayed here and we had plenty of room to spread out with lots of living areas and bedrooms to choose from. The outside space was also well laid out and comfortable - especially the pool! The location is excellent - not far from Florence (we parked at a shopping centre on the edge of town and took the tram in), also Pisa, Siena, Lucca & San Gimignano are all an easy drive away. The owner was very helpful and even arranged for us to arrive late when we were delayed by losing a suitcase!

Robert

Reviewed on 16/09/2025

Fantastic accommodation for a family holiday. Loved the countryside views, loved the pool, loved the help P. offered. Beautifully decorated, spotlessly clean and very comfortable. The road to the property is an adventure but makes you feel tucked away, even though Mercatale is only a few minutes away. If you're staying over a weekend make sure to eat at Circolo Arci Mercatale in val di Pesa! Thank you so much for being to setting for our daughters first trip abroad!

Jessica

Reviewed on 23/06/2025

We had a wonderful stay at the authentic stone villa surrounded by vineyards. The house had everything we needed, and help was always available when needed. The pool and peaceful surroundings were perfect. The wine tasting at the estate was a great experience. The owners were kind and welcoming. We especially want to thank R. for her kindness and support. Highly recommended!

Tiina

Reviewed on 14/06/2025

Come here for the unbearable 360 views and quirky character of the home! Slept well, cooked/ate well, swam well Wished for more linens--pillows, blankets, towels--but what we had was adequate Wished to have a shareable map/visual of the appropriate route to take to avoid bad roads, but overall were able to manage Taxi accessible! Appreciated host's guidance on arrival regarding fuse box quirks and other details about the home Appreciated quirky art collection! A memorable vacation

Ann

Reviewed on 26/05/2025

I visited Il Poggetto with my family making a group of seven. The accommodation was on the top of a hill with fantastic views (the property is in the middle of a vineyard), and plenty of bedrooms and bathrooms. The kitchen was very useful for making food at home and the terrace provided a big table for everyone to eat together. The property was also clean and tidy on arrival. There is a vineyard just under half an hour's walk away which meant we could all do wine tasting which was ideal.

Elliot

Reviewed on 05/05/2025

A perfect holiday house with a beautiful view over the Tuscany-hills. The owner is very sweet and helpful with everything from restaurant tips and bookings to anything around the house and wine-tastings. Our kids spent quite some time in the pool and at the ping-pong table. The location of the house is a good base for exploring the area and many Tuscany sightseeings can be reached within 1,5 hour’s car driving. We can highly recommend a stay at Casa Sole!

Ann-Charlotte

Reviewed on 11/07/2024

Our stay in Tuscany was nothing short of magical, thanks to the breathtaking property we were fortunate to call home during our visit. Nestled atop a picturesque hill, the views from this villa are simply unparalleled. Waking up to the sun rising over the rolling vineyards and distant hills was a daily treat that will forever be etched in our memories. Our heartfelt thanks to the owners for sharing this slice of paradise with us.

AGRICOLA A.

Reviewed on 03/07/2024

Our extended family enjoyed a really lovely, relaxing holiday. The pool was the highlight, with lots of space for the children to enjoy. Really enjoyed the vineyard tour and home cooked meal too!

Laura

Reviewed on 03/11/2023

The house can best be described as functional. It serves well for 10 people, but there are definitely improvements possible. The pool is large and was much used. Breakfast & dinner outside was great in the large enough garden. The absolute biggest asset: An astonishing 270 degrees view from the house on a hill. No better way to position a holiday house. Sufficient nice villages around, great cycling roads and dining opportunities. Downside: Very bumpy road to the house. Overall: Recommended!

Robbert

Reviewed on 21/08/2023

We loved our stay at Villa Ambrogetta. The view in the Val di Pesa from the hill, the pool and the house itself were the perfect mixture for a recreative stay.

Christian

Reviewed on 28/06/2021

Holiday homes with parking

Experience hassle-free arrivals and departures with our holiday homes San Casciano in Val di Pesa offering convenient parking access for your convenience.

House San Casciano in Val di Pesa
from £108 per night
House ∙ 6 guests ∙ 3 bedrooms

House Torsoli

4.6
Excellent(71 ratings)
San Casciano in Val di Pesa, Metropolitan City of Florence, Italy
View deal
House San Casciano in Val di Pesa
from £68 per night
House ∙ 3 guests ∙ 1 bedroom

House San Rocco

3.8
Good(10 ratings)
San Casciano in Val di Pesa, Metropolitan City of Florence, Italy
View deal
House San Casciano in Val di Pesa
from £121 per night
House ∙ 8 guests ∙ 4 bedrooms

House Fienile

4.6
Excellent(80 ratings)
San Casciano in Val di Pesa, Metropolitan City of Florence, Italy
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Cool comfort: accommodation with refreshing air-conditioning San Casciano in Val di Pesa

Enjoy cool comfort in our holiday homes San Casciano in Val di Pesa equipped with refreshing air conditioning for ultimate relaxation.

House San Casciano in Val di Pesa
from £254 per night
House ∙ 4 guests ∙ 2 bedrooms

House Casa Aia

San Casciano in Val di Pesa, Metropolitan City of Florence, Italy
Air conditioning
View deal
Apartment San Casciano in Val di Pesa
from £82 per night
Apartment ∙ 4 guests ∙ 1 bedroom

Apartment Bufalini 3 - Michelangelo

4.5
Excellent(27 ratings)
San Casciano in Val di Pesa, Metropolitan City of Florence, Italy
Air conditioning
View deal
Apartment San Casciano in Val di Pesa
from £117 per night
Apartment ∙ 4 guests ∙ 2 bedrooms

Apartment Leonardo

4.7
Excellent(19 ratings)
San Casciano in Val di Pesa, Metropolitan City of Florence, Italy
Air conditioning
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Best holiday lettings with a pool

A swimming pool is a holiday home staple, and with 83% of the holiday rentals San Casciano in Val di Pesa providing pool access, there are plenty of great options from which to choose. Get ready to take a dip and dive into the top offers for accommodation with private pools San Casciano in Val di Pesa.

House San Casciano in Val di Pesa
from £347 per night
House ∙ 6 guests ∙ 3 bedrooms

House Il Fienile

San Casciano in Val di Pesa, Metropolitan City of Florence, Italy
Pool
View deal
Apartment San Casciano in Val di Pesa
from £149 per night
Apartment ∙ 9 guests ∙ 4 bedrooms

Apartment Il Forno

4.7
Excellent(103 ratings)
San Casciano in Val di Pesa, Metropolitan City of Florence, Italy
Pool
View deal
House San Casciano in Val di Pesa
from £181 per night
House ∙ 7 guests ∙ 3 bedrooms

House La Torre

4.6
Excellent(38 ratings)
San Casciano in Val di Pesa, Metropolitan City of Florence, Italy
Pool
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Quality is our number one priority

Every property is checked before your arrival to ensure the best possible stay.

In-resort service and a 24/7 helpline

Make the most of our experience

Key collection is arranged by our helpful staff. Available 24/7 or on-site service to help you with all your questions, e.g.: tips and insights for your holiday destination and your booked accommodation.

A memorable holiday experience

Privacy and freedom in your own holiday homes

Be your own boss, eat whenever you want and make the most of plenty of space for all your friends and family.

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