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Check prices for these dates

In two weeks
6 Mar - 8 Mar
In two months
17 Apr - 19 Apr
In three months
15 May - 17 May
In four months
12 Jun - 14 Jun

Our top choices for San Casciano in Val di Pesa holiday rentals

Property entrance

Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (99 reviews)
"Great people, great location great service"
Canada
James
The price is 4.266.872 ₫
4.816.669 ₫ total
includes taxes & fees
24 Feb - 25 Feb
Villa il Fedino
Outdoor dining

B&B La Fonte del Machiavelli

B&B La Fonte del Machiavelli
San Casciano in Val di Pesa
9.2 out of 10, Wonderful, (82 reviews)
"It was a wonderful stay the bed was comfortable and the view was beautiful. "
United States
Ruben
The price is 3.189.661 ₫
3.631.737 ₫ total
includes taxes & fees
20 Feb - 21 Feb
B&B La Fonte del Machiavelli
Exterior

B&B Le Dimore Mezza Costa

B&B Le Dimore Mezza Costa
San Casciano in Val di Pesa
9.4 out of 10, Exceptional, (25 reviews)
"The beautiful place, very comfortable, the incredible attention, the breakfast felt like in Homewith a lot of love We hope to return one day"
Mexico
Raymundo
The price is 2.235.546 ₫
2.582.224 ₫ total
includes taxes & fees
2 Mar - 3 Mar
B&B Le Dimore Mezza Costa
Free daily buffet breakfast

Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (72 reviews)
"The stay was great, and the staff were wonderful. "
United States
SYDNEY
Terre di Baccio
Breakfast, lunch, dinner served; garden views

Marignolle Relais and Charme

Marignolle Relais and Charme
Florence
9.2 out of 10, Wonderful, (91 reviews)
"I stayed here June 2025 and was most delighted in the property and staff. They were incredibly kind and accommodating and the property is beautiful. Would stay here again!"
Canada
Shelley
Marignolle Relais and Charme
City view from property

Boboli Living

Boboli Living
Historic Centre of Florence
The price is 2.350.165 ₫
2.954.511 ₫ total
includes taxes & fees
23 Feb - 24 Feb
Boboli Living
Property grounds

Domus il Palio B&B

Domus il Palio B&B
Ravacciano
9.2 out of 10, Wonderful, (83 reviews)
"Hotel clean comfortable. No elevator, no reception desk. "
United States
Karin
Domus il Palio B&B
Balcony

Palazzo al Torrione 2

Palazzo al Torrione 2
San Gimignano City Centre
9.2 out of 10, Wonderful, (107 reviews)
"Great location, beautiful room with a terrace and the best breakfast we had in Italy! "
United States
Angel
The price is 2.323.389 ₫
3.479.082 ₫ total
includes taxes & fees
28 Feb - 1 Mar
Palazzo al Torrione 2
Deluxe Room, Patio | Frette Italian sheets, premium bedding, minibar, in-room safe

Tenuta Sant'Ilario

Tenuta Sant'Ilario
Gambassi Terme
9.4 out of 10, Exceptional, (34 reviews)
"Amazing location and property! Owner and staff super nice! I am sure we will be back!"
Australia
Ilaria
Tenuta Sant'Ilario
Garden

Tenuta Quadrifoglio

Tenuta Quadrifoglio
Gambassi Terme
10.0 out of 10, Exceptional, (5 reviews)
"A lovely spot for relaxation .The appartments were lovely and comfortable .the only criticism was you do need a car to get any where. It is totally in the middle of nowhere. "
United Kingdom
Geraldine
The price is 4.952.397 ₫
5.539.938 ₫ total
includes taxes & fees
28 Feb - 1 Mar
Tenuta Quadrifoglio
View from room

Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Barberino Tavarnelle
8.6 out of 10, Excellent, (112 reviews)
"Spacious room in large resort style complex, set up as fully self contained with kitchen and dining furniture. Peaceful location with lovely views. Very pleasant staff and exceptional breakfast. "
France
Richard
Chianti Village Morrocco
Free WiFi, wheelchair access

LE BOTTI FIORENTINE

LE BOTTI FIORENTINE
Reggello
The price is 3.339.562 ₫
3.827.424 ₫ total
includes taxes & fees
23 Feb - 24 Feb
LE BOTTI FIORENTINE
Property amenity

hu Firenze Certosa camping in town

hu Firenze Certosa camping in town
Impruneta
8.0 out of 10, Very good, (59 reviews)
"Wonderful staff and great amenities!"
Canada
Chenjin
hu Firenze Certosa camping in town
Seasonal outdoor pool, open 9:00 AM to 8:00 PM, pool umbrellas

Fattoria il Milione Agriturismo

Fattoria il Milione Agriturismo
4.0 star property
Florence
8.4 out of 10, Very good, (232 reviews)
"We stayed two days with kids. Perfect resort feeling, enjoyed sun rising, perfect ample amount of healthy and fresh breakfast, very welcoming and friendly helpful staff, room are spacious and clean, and cozy remote control heating options, washrooms are very clean and water is always hot. "
Canada
Manjeet
The price is 2.017.041 ₫
2.649.629 ₫ total
includes taxes & fees
19 Feb - 20 Feb
Fattoria il Milione Agriturismo
Outdoor spa tub

Forte16 View & Spa

Forte16 View & Spa
Santissima Annunziata
9.6 out of 10, Exceptional, (916 reviews)
"Great hotel lovely staff nice breakfast. Clean and comfortable "
United Kingdom
carol
The price is 2.993.805 ₫
3.662.514 ₫ total
includes taxes & fees
2 Mar - 3 Mar
Forte16 View & Spa
Reception

Teatro Luxury Apartments Firenze - Starhotels Collezione

Teatro Luxury Apartments Firenze - Starhotels Collezione
Historic Centre of Florence
9.8 out of 10, Exceptional, (58 reviews)
"Staffs were nice and th room was cozy and nice. "
United Kingdom
Anyanee
The price is 4.756.513 ₫
5.601.493 ₫ total
includes taxes & fees
1 Mar - 2 Mar
Teatro Luxury Apartments Firenze - Starhotels Collezione
Presidential Suite, River View | Balcony

Il Rivalta - Place of Charme

Il Rivalta - Place of Charme
4.0 star property
Historic Centre of Florence
9.2 out of 10, Wonderful, (467 reviews)
"Excellent place 👍"
United States
Assif
The price is 5.001.926 ₫
5.933.054 ₫ total
includes taxes & fees
22 Feb - 23 Feb
Il Rivalta - Place of 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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Top San Casciano in Val di Pesa Hotel Reviews

IQ Hotel Firenze

IQ Hotel Firenze

10/10 Excellent
"The hotel was very nice. The staff was very nice, very clean, very cozy. Just a beautiful hotel."
Katherine 3-night trip
Posted 3 days ago
IQ Hotel Firenze

Frequently asked questions

Are there holiday rentals in San Casciano in Val di Pesa?

Yes, there are holiday rentals close to the most popular sights in San Casciano in Val di Pesa, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to San Casciano in Val di Pesa speak positively about the countryside and wineries in this destination. Make sure you have time to check out the spas and coffee shops during your trip.

How many holiday rentals are there in San Casciano in Val di Pesa?

Choose from 19 Expedia holiday rentals in San Casciano in Val di Pesa for a memorable holiday.

What can I see and do in San Casciano in Val di Pesa?

While exploring the area, visit family-friendly sights like Villa Medicea di Lilliano - Malenchini, or get outside and enjoy nature at Boboli Gardens. Piazza di Santa Maria Novella and Cathedral of Santa Maria del Fiore are other popular places to visit in the area.

What are holiday rentals like in San Casciano in Val di Pesa?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in San Casciano in Val di Pesa. Holiday rentals offer extras like kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a clean environment, holiday rentals can provide a sense of safety away from shared hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental a great option for a small group gathering.