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Holiday Rentals in San Casciano in Val di Pesa

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

Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (97)
"Great people, great location great service"
Canada
James
The price is €141
includes taxes & fees
7 Jan - 8 Jan 2026
Villa il Fedino

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)
"It was a wonderful stay the bed was comfortable and the view was beautiful. "
United States
Ruben
The price is €118
includes taxes & fees
24 Dec - 25 Dec
B&B La Fonte del Machiavelli

Beautiful Tuscan home between Florence & Siena

Beautiful Tuscan home between Florence & Siena
Florence
10.0 out of 10, Exceptional, (6)
"Judy was amazing and very helpfulNothing to do with the property, but I sure you pre book all nights out/transportation"
United States
Frank V.
The price is €1,317
includes taxes & fees
3 Jan - 4 Jan 2026
Beautiful Tuscan home between Florence & Siena

San Giuliano Inn - Adults Only

San Giuliano Inn - Adults Only
Historic Centre of Florence
10.0 out of 10, Exceptional, (406)
"Great inn. "
United States
Carol
San Giuliano Inn - Adults Only

Sette Angeli Rooms

Sette Angeli Rooms
Historic Centre of Florence
8.8 out of 10, Excellent, (636)
"I loved this place and the stuff was very kind <3 "
United Kingdom
romina
The price is €88
includes taxes & fees
25 Dec - 26 Dec
Sette Angeli Rooms

Home in Florence

Home in Florence
Historic Centre of Florence
9.0 out of 10, Wonderful, (70)
"Perfect place, super friendly owners, really helpful. "
United Kingdom
Paul
The price is €80
includes taxes & fees
24 Dec - 25 Dec
Home in Florence

La Senesina, Monteriggioni, Siena. In the best countryside of Tuscany !

La Senesina, Monteriggioni, Siena. In the best countryside of Tuscany !
Siena
10.0 out of 10, Exceptional, (66)
"Great Place and super nice Host. Location is very nice, top equiped and located only a couple of minutes away from Siena. Host is a really nice Person that has super good ideas where to go, in turism and wine/food matters. Really loved our stay (me and my Kids 14years), definitely come back. Highly recommended"
Germany
Michael G.
The price is €250
includes taxes & fees
29 Dec - 30 Dec
La Senesina, Monteriggioni, Siena. In the best countryside of Tuscany !

Tenuta Sant'Ilario

Tenuta Sant'Ilario
Gambassi Terme
9.4 out of 10, Exceptional, (33)
"Amazing location and property! Owner and staff super nice! I am sure we will be back!"
Australia
Ilaria
Tenuta Sant'Ilario

Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Barberino Tavarnelle
8.6 out of 10, Excellent, (108)
"Front desk was very helpful and very comfortable room. "
United States
Chris
Chianti Village Morrocco

Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (71)
"The stay was great, and the staff were wonderful. "
United States
SYDNEY
Terre di Baccio

Numa Palazzo San Niccolò

Numa Palazzo San Niccolò
Historic Centre of Florence
9.4 out of 10, Exceptional, (174)
"Clean, amenities, breakfast! "
United States
Laury
The price is €98
includes taxes & fees
7 Jan - 8 Jan 2026
Numa Palazzo San Niccolò

La Torre Del Cestello

La Torre Del Cestello
Historic Centre of Florence
9.0 out of 10, Wonderful, (229)
"Great location and great rooms"
United States
David
The price is €102
includes taxes & fees
22 Jan - 23 Jan 2026
La Torre Del Cestello

Corte Guelfa

Corte Guelfa
3.0 star property
Historic Centre of Florence
9.8 out of 10, Exceptional, (160)
"Great location, attentive staff, clean rooms"
United States
Dennis
Corte Guelfa

Palazzo Mannaioni Suites

Palazzo Mannaioni Suites
4.0 star property
Historic Centre of Florence
9.2 out of 10, Wonderful, (1073)
"Perfect stay"
United States
Juan P
The price is €115
includes taxes & fees
22 Jan - 23 Jan 2026
Palazzo Mannaioni Suites

Serristori Palace Residence

Serristori Palace Residence
Historic Centre of Florence
9.6 out of 10, Exceptional, (171)
"Perfect stay. Apartment was immaculate as were all the public areas of the building. Helpful friendly staff and ideally placed to explore Florence’s "
United Kingdom
Michele
Serristori Palace Residence

Palazzo Branchi

Palazzo Branchi
Historic Centre of Florence
9.0 out of 10, Wonderful, (287)
"WHAT A GREAT STAY. The location is perfect if you want to stay in the heart of Florence. Easy to reach all of the main attractions. The room was so pretty and spacious. Our host was very helpful, greeted us at the door, and had with great tips! Will stay here again. "
United States
Jeannette
The price is €120
includes taxes & fees
7 Jan - 8 Jan 2026
Palazzo Branchi

Soggiorno Alessandra

Soggiorno Alessandra
Historic Centre of Florence
8.6 out of 10, Excellent, (86)
"Alessandra is an amazing host, we had a perfect stay! The apartment is in excellent condition and very clean! "
United States
Elias
Soggiorno Alessandra

Bob W Florence Ponte Vecchio

Bob W Florence Ponte Vecchio
Historic Centre of Florence
9.2 out of 10, Wonderful, (211)
"Very nice, quiet area of Florence! You cannot ask for a better location within walking distance of so many famous tourist sites! "
United States
Denise
The price is €113
includes taxes & fees
16 Jan - 17 Jan 2026
Bob W Florence Ponte Vecchio

Numa Florence Palazzo Belfiore

Numa Florence Palazzo Belfiore
Historic Centre of Florence
9.6 out of 10, Exceptional, (371)
"Great property, plenty of space for my family. The location is great, we were able to walk everywhere including the train station. "
United States
Loren
The price is €154
includes taxes & fees
11 Jan - 12 Jan 2026
Numa Florence Palazzo Belfiore

Dimora Bandinelli Firenze

Dimora Bandinelli Firenze
Oltrarno
9.6 out of 10, Exceptional, (170)
"We loved this place! The staff were amazing, informative and helpful. Breakfast was great. Highly recommend"
United Kingdom
Simran
The price is €92
includes taxes & fees
18 Jan - 19 Jan 2026
Dimora Bandinelli Firenze
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

Find out more about San Casciano in Val di Pesa

Everything you need to know about San Casciano in Val di Pesa holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the San Casciano in Val di Pesa holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect San Casciano in Val di Pesa holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

San Casciano in Val di Pesa holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in San Casciano in Val di Pesa. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A San Casciano in Val di Pesa holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of San Casciano in Val di Pesa holiday rentals we have selected for you start as low as €78 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on San Casciano in Val di Pesa rentals

At Expedia, we put the best San Casciano in Val di Pesa holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top San Casciano in Val di Pesa rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream San Casciano in Val di Pesa holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around San Casciano in Val di Pesa. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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.

What are some of the best holiday rentals that San Casciano in Val di Pesa has to offer?

QK Costa58 Home Tower: This holiday home rental outside of San Casciano in Val di Pesa is located in the historical district, and offers a terrace, air conditioning and daily housekeeping to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

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

Choose from 20 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. Monastary of Sorelle Clarisse and Antinori nel Chianti Classico are other places to visit while you're in town.

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.