Panoramic view of beautiful rows of colored vineyards nella campagna toscana in the Chianti region near San Casciano in Val di Pesa. Autumn season in October. Italy.

San Casciano in Val di Pesa Vacation Rentals

Check prices for these dates

In two weeks
Jun 26 - Jun 28
In two months
Aug 7 - Aug 9
In three months
Sep 4 - Sep 6
In four months
Oct 2 - Oct 4

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

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
$121 nightly
The price is $138
Jun 16 - Jun 17
Total with taxes and fees
B&B La Fonte del Machiavelli
Exterior

B&B Le Dimore di Mezza Costa - Home Restaurant & Cooking Classes

B&B Le Dimore di Mezza Costa - Home Restaurant & Cooking Classes
San Casciano in Val di Pesa
9.2 out of 10, Wonderful, (27 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
$110 nightly
The price is $125
Jun 21 - Jun 22
Total with taxes and fees
B&B Le Dimore di Mezza Costa - Home Restaurant & Cooking Classes
Property entrance

Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (100 reviews)
"This is a lovely gem. Includes parking which is hard to find. Family owned and its a truly beautiful place. Breakfast was amazing as well!! Recommend!! "
United States
rose
$233 nightly
The price is $261
Jun 23 - Jun 24
Total with taxes and fees
Villa il Fedino
Pool

Tenuta Branca – Apartment La Loggia with Pool and Private Terrace in Chianti

Tenuta Branca – Apartment La Loggia with Pool and Private Terrace in Chianti
San Casciano in Val di Pesa
$373 nightly
The price is $378
Jul 4 - Jul 5
Total with taxes and fees
Tenuta Branca – Apartment La Loggia with Pool and Private Terrace in Chianti
Outdoor pool

Beautiful Tuscan home between Florence & Siena

Beautiful Tuscan home between Florence & Siena
Florence
10.0 out of 10, Exceptional, (8 reviews)
"From the moment we entered to our last day everything was perfect. Group of 15 and we all fit comfortably. "
United States
Debra P.
$2,882 nightly
The price is $2,882
Jun 14 - Jun 15
Total with taxes and fees
Beautiful Tuscan home between Florence & Siena
Pool

Tenuta Branca – Torrione Spacious Apartment with Pool in Chianti

Tenuta Branca – Torrione Spacious Apartment with Pool in Chianti
San Casciano in Val di Pesa
$566 nightly
The price is $572
Jul 10 - Jul 11
Total with taxes and fees
Tenuta Branca – Torrione Spacious Apartment with Pool in Chianti
Food court

Home in Florence

Home in Florence
Historic Centre of Florence
9.0 out of 10, Wonderful, (75 reviews)
"Lovely room and the people running the place were friendly and efficient "
United Kingdom
Thomas
$137 nightly
The price is $164
Jun 24 - Jun 25
Total with taxes and fees
Home in Florence
Deluxe Double Room, City View | Room amenity

San Giuliano Inn - Adults Only

San Giuliano Inn - Adults Only
Historic Centre of Florence
10.0 out of 10, Exceptional, (432 reviews)
"Clean, friendly staff. Great location. "
United States
Jeannette
$178 nightly
The price is $210
Jun 11 - Jun 12
Total with taxes and fees
San Giuliano Inn - Adults Only
Exterior

Hu Norcenni Girasole Village

Hu Norcenni Girasole Village
4.0 star property
Figline e Incisa Valdarno
8.6 out of 10, Excellent, (320 reviews)
"Beautiful place for family "
Canada
Ismail
$57 nightly
The price is $66
Jun 11 - Jun 12
Total with taxes and fees
Hu Norcenni Girasole Village
Property grounds

Domus il Palio B&B

Domus il Palio B&B
Ravacciano
9.2 out of 10, Wonderful, (91 reviews)
"Rooms were clean and spacious ! Happy there was a good blow dryer in the room and a heated towel rack. Staff were very friendly and helpful . Would stay again !"
Canada
Alissia
$75 nightly
The price is $87
Jul 8 - Jul 9
Total with taxes and fees
Domus il Palio B&B
Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers

Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.4 out of 10, Exceptional, (33 reviews)
"Beautiful villa, very spacious, gorgeous property and great restaurant on the property to have a delicious meal. Staff very welcoming. Close to other main cities, like Siena, for day trips. We loved sitting by the pool, although it wasn’t heated, so too cold to use in April. We did love using the indoor heated pool and hot tub each day. We had a fabulous time and hope to go back someday! "
Canada
Jeremy
$147 nightly
The price is $162
Jun 18 - Jun 19
Total with taxes and fees
Villa di Sotto
Exterior

Borgo Argenina

Borgo Argenina
Gaiole in Chianti
9.8 out of 10, Exceptional, (23 reviews)
"Such a beautiful place to stay! The cottage was amazing, very spacious and clean. The grounds themselves were picturesque, was well above our expectations and the host was very welcoming and accommodating."
United Kingdom
Sasha
$346 nightly
The price is $389
Jun 18 - Jun 19
Total with taxes and fees
Borgo Argenina
Balcony

Palazzo al Torrione 2

Palazzo al Torrione 2
San Gimignano City Centre
9.2 out of 10, Wonderful, (109 reviews)
"Great location and beautiful room. Staff weren't that friendly but I think it would have been better if we spoke Italian."
Canada
Sophie
$135 nightly
The price is $154
Jun 25 - Jun 26
Total with taxes and fees
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, (35 reviews)
"Great place, difficult driving access but enjoyable"
United States
Sergio
$127 nightly
The price is $144
Jun 18 - Jun 19
Total with taxes and fees
Tenuta Sant'Ilario
View from room

Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Barberino Tavarnelle
8.6 out of 10, Excellent, (113 reviews)
"Front desk was very helpful and very comfortable room. "
United States
Chris
$78 nightly
The price is $88
Jun 11 - Jun 12
Total with taxes and fees
Chianti Village Morrocco
Exterior

DomuS Miniato

DomuS Miniato
San Miniato
10.0 out of 10, Exceptional, (1 review)
"Kjempefint rom, nydelig utsikt og hyggelig vertsskap. Anbefales. "
Norway
Karen
$91 nightly
The price is $102
Jun 25 - Jun 26
Total with taxes and fees
DomuS Miniato
Free daily buffet breakfast

Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (75 reviews)
"We had a wonderful experience! The staff was kind and very helpful. Our room was stunning and very spacious for a family of 5! The breakfast was amazing, and all of the activities on site were very fun - we especially enjoyed the cooking class! I would absolutely love to return here. I recommend looking into and booking on-site activities in advance so you can get the most out of your experience!"
United States
Julia
$311 nightly
The price is $347
Jun 16 - Jun 17
Total with taxes and fees
Terre di Baccio
Property amenity

hu Firenze Certosa camping in town

hu Firenze Certosa camping in town
Impruneta
8.2 out of 10, Very Good, (73 reviews)
"Good location. The bed and pillows not so good ! "
United States
Sebastian
$45 nightly
The price is $53
Jun 11 - Jun 12
Total with taxes and fees
hu Firenze Certosa camping in town
Superior Double Room, 1 King Bed | Premium bedding, down comforters, in-room safe, desk

La Torre Del Cestello

La Torre Del Cestello
Historic Centre of Florence
9.0 out of 10, Wonderful, (261 reviews)
"Central city location"
United States
Srideep
$129 nightly
The price is $158
Jul 2 - Jul 3
Total with taxes and fees
La Torre Del Cestello
Restaurant

Relais Villa Olmo

Relais Villa Olmo
Impruneta
9.4 out of 10, Exceptional, (245 reviews)
"Delightful location, comfortable bed, excellent food."
Canada
Rupert
$144 nightly
The price is $162
Jun 24 - Jun 25
Total with taxes and fees
Relais Villa Olmo
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top San Casciano in Val di Pesa Hotel Reviews

The Social Hub Florence Lavagnini

The Social Hub Florence Lavagnini

10/10 Excellent
"I absolutely loved my stay at The Social Hub. The rooftop patio alone was incredible. Such a great value and centrally located. I highly recommend this hotel for your next stay in Florence."
Natalie 1-night trip
Posted 9 hours ago
The Social Hub Florence Lavagnini

Find out more about San Casciano in Val di Pesa

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

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the San Casciano in Val di Pesa vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation 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 vacation 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 low season months. For more hustle and bustle, you may prefer to visit San Casciano in Val di Pesa in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $53 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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 vacation 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 vacation.

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.

Explore a world of travel with Expedia

Frequently asked questions

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

Yes, you can find vacation rentals near popular local attractions in San Casciano in Val di Pesa, or you can choose a more remote option if you want a relaxing place to 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 coffeehouses during your trip.

What's the top vacation rental in San Casciano in Val di Pesa?

Villa La Stella - Casa per Ferie: This vacation home rental near San Casciano in Val di Pesa is located near the airport and has a garden, a library, and air-conditioning to put you at ease in your new surroundings. This vacation rental also comes with free parking to give you added peace of mind.

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

Choose from 28 Expedia vacation rentals in San Casciano in Val di Pesa for a memorable vacation.

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. Pitti Palace and Uffizi Gallery are other popular places to visit in the area.

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

Vacation rentals are private accommodations you can book for a short or long stay in San Casciano in Val di Pesa. Vacation rentals provide amenities like kitchens and laundry facilities so you'll have everything you need. If you're concerned about cleanliness, vacation rentals can provide a sense of privacy away from shared hotel elevators and lobbies bustling with people while still allowing you to travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great choice for family trips or small group gatherings.