A vineyard with rows of grapevines on rolling hills, a small house, and a mountain range in the background.

San Casciano in Val di Pesa Vacation Rentals

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Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for San Casciano in Val di Pesa vacation 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, (103 reviews)
"This is an excellent property. Very historic, rustic and with great views across the Tuscan landscapes. Lorenzo and his mother were super duper hosts who took great care of us. The property dates back to 1380 and the rooms are decorated with choicest artifacts that adds greatly to the experience. The location is fantastic too with the local market and restaurants in easy walking reach. The breakfast service is fabulous with many choices and Lorenzo himself is great chef as well! Highly recommend...
United States
Nilesh
$208 nightly
The price is $233
Oct 4 - Oct 5
Total with taxes and fees
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, (84 reviews)
"Very pretty B&B! The rooms are super cozy and feels welcoming! The scenery around is just amazing! The pool was very refreshing and the host very nice! The trail to reach the B&B is narrow make sure you have a small car ;)"
Canada
Alexia
$107 nightly
The price is $123
Oct 4 - Oct 5
Total with taxes and fees
B&B La Fonte del Machiavelli

3. 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
$101 nightly
The price is $116
Oct 8 - Oct 9
Total with taxes and fees
B&B Le Dimore di Mezza Costa - Home Restaurant & Cooking Classes
A garden with various plants and flowers, a pathway, and a swing set.

4. Apartment House with garden Tuscany Chianti , Florence 15km.

Apartment House with garden Tuscany Chianti , Florence 15km.
Toscana
9.8 out of 10, Exceptional, (75 reviews)
"Great property, well equipped, nice views, well maintained, very friendly and helpful host. We did really enjoy our stay :-)"
Germany
Robert M.
$158 nightly
The price is $163
Sep 9 - Sep 10
Total with taxes and fees
Apartment House with garden Tuscany Chianti , Florence 15km.

5. Apartment 'Mini in Chianti' with Shared Pool, Wi-Fi and Air Conditioning

Apartment 'Mini in Chianti' with Shared Pool, Wi-Fi and Air Conditioning
San Casciano in Val di Pesa
$652 nightly
The price is $656
Oct 6 - Oct 7
Total with taxes and fees
Apartment 'Mini in Chianti' with Shared Pool, Wi-Fi and Air Conditioning
An outdoor patio with a round table, chairs, a sofa, and a potted plant.

6. Molino In Chianti - Villa with Private Pool

Molino In Chianti - Villa with Private Pool
Mercatale Val Di Pesa
$1,608 nightly
The price is $1,612
Sep 13 - Sep 14
Total with taxes and fees
Molino In Chianti - Villa with Private Pool

7. Portion of Villa Il Conventino with Pool and Wi-Fi

Portion of Villa Il Conventino with Pool and Wi-Fi
San Casciano in Val di Pesa
$3,438 nightly
The price is $3,442
Oct 6 - Oct 7
Total with taxes and fees
Portion of Villa Il Conventino with Pool and Wi-Fi

8. Cottage in Chianti Barn with Shared Pool, Wi-Fi, and Air Conditioning

Cottage in Chianti Barn with Shared Pool, Wi-Fi, and Air Conditioning
San Casciano in Val di Pesa
$878 nightly
The price is $883
Oct 6 - Oct 7
Total with taxes and fees
Cottage in Chianti Barn with Shared Pool, Wi-Fi, and Air Conditioning
A desk with a computer monitor displaying a cityscape, a lamp, a vase with flowers, glasses, a wine bottle, and books.

9. San Giuliano Inn - Adults Only

San Giuliano Inn - Adults Only
Historic Centre of Florence
9.8 out of 10, Exceptional, (445 reviews)
"Clean, friendly staff. Great location. "
United States
Jeannette
$208 nightly
The price is $243
Sep 9 - Sep 10
Total with taxes and fees
San Giuliano Inn - Adults Only
A modern bedroom with a wooden ceiling, a large bed, bedside tables with lamps, a desk with a chair, and a mirror on the wall.

10. Sette Angeli Rooms

Sette Angeli Rooms
Historic Centre of Florence
8.8 out of 10, Excellent, (687 reviews)
"Good clean rooms and very close to the city center as well as the train station"
United Kingdom
VISHAL
$186 nightly
The price is $219
Sep 9 - Sep 10
Total with taxes and fees
Sette Angeli Rooms
A modern kitchen with a wooden countertop, a laptop, and a wine bottle.

11. Maison Ginori Guelfa

Maison Ginori Guelfa
Historic Centre of Florence
10.0 out of 10, Exceptional, (38 reviews)
"This was an incredible stay. The host was a phenomenal communicator and the property is as beautiful as pictured. If you want to be downtown in the heart of Florence, this is the perfect place to be and it is also far enough from the standard noise. I had peaceful nights and peaceful days, if I chose a late morning. It was literally near everything and I walked to every place I wanted to see. It was safe and easy to get to. I would absolutely stay at this property again and couldn’t have asked...
United States
Joyce
$242 nightly
The price is $280
Sep 24 - Sep 25
Total with taxes and fees
Maison Ginori Guelfa
A garden with a stone pathway, wooden benches, and various potted plants.

12. Antico Borgo il Cardino

Antico Borgo il Cardino
San Gimignano
9.4 out of 10, Exceptional, (85 reviews)
"It was perfect for my one night stop before moving on to another location in Toscana."
United States
Craig
$145 nightly
The price is $165
Oct 4 - Oct 5
Total with taxes and fees
Antico Borgo il Cardino
An outdoor swimming pool with a wooden pergola, lounge chairs, and a stone wall backdrop.

13. Guild Living Siena Senior Resort & Residence

Guild Living Siena Senior Resort & Residence
Scacciapensieri
8.8 out of 10, Excellent, (49 reviews)
"New facilities, its great, nice, friendly"
United Kingdom
tomaz
$131 nightly
The price is $149
Oct 6 - Oct 7
Total with taxes and fees
Guild Living Siena Senior Resort & Residence
A table with two wine glasses, a bottle, and a book.

14. Domus il Palio B&B

Domus il Palio B&B
Ravacciano
9.2 out of 10, Wonderful, (97 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
$63 nightly
The price is $74
Sep 24 - Sep 25
Total with taxes and fees
Domus il Palio B&B
A stone building with a garden in front.

15. Borgo Argenina

Borgo Argenina
Gaiole in Chianti
9.8 out of 10, Exceptional, (27 reviews)
"What an amazing place. We enjoyed it so much."
United States
Tatevik
$240 nightly
The price is $273
Sep 10 - Sep 11
Total with taxes and fees
Borgo Argenina
A white mobile home with blue shutters, a red roof, and a small deck with white chairs.

16. Camping Boschetto Di Piemma

Camping Boschetto Di Piemma
3.0 star property
San Gimignano
8.8 out of 10, Excellent, (89 reviews)
"Great experience, close to a beautiful city and castle on a hill. "
New Zealand
Anonymous traveler
$45 nightly
The price is $53
Sep 24 - Sep 25
Total with taxes and fees
Camping Boschetto Di Piemma
A pool area with two rectangular pools, surrounded by lounge chairs and umbrellas, set against a backdrop of vineyards and tall cypress trees.

17. Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (39 reviews)
"Great spot"
Canada
Philippe
$152 nightly
The price is $167
Sep 21 - Sep 22
Total with taxes and fees
Villa di Sotto
A table with breakfast items and a view of rolling hills.

18. Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Tavarnelle Val di Pesa
8.6 out of 10, Excellent, (117 reviews)
"Front desk was very helpful and very comfortable room. "
United States
Chris
$80 nightly
The price is $91
Oct 9 - Oct 10
Total with taxes and fees
Chianti Village Morrocco
A restaurant with hanging baskets of greenery, wicker furniture, and a view of the outdoors.

19. Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (79 reviews)
"The stay was great, and the staff were wonderful. "
United States
SYDNEY
$333 nightly
The price is $370
Sep 21 - Sep 22
Total with taxes and fees
Terre di Baccio
A spacious indoor area with arched windows, wooden furniture, and hanging plants.

20. Relais Villa Olmo

Relais Villa Olmo
Impruneta
9.4 out of 10, Exceptional, (264 reviews)
"Delightful location, comfortable bed, excellent food."
Canada
Rupert
$186 nightly
The price is $208
Oct 5 - Oct 6
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.
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Top San Casciano in Val di Pesa Hotel Reviews

Hotel Albani Firenze

Hotel Albani Firenze

10/10 Excellent
"This place was great. A 2 minute walk from the train station. The staff members were all super friendly and eager to make your stay pleasurable. The bags were taken to our room. Every night a small chocolate cookie was delivered to the room. The room and bathroom were big and clean!!! Breakfast was a good way to start our days."
Yamile 2-night trip
Posted 2 hours ago
Hotel Albani Firenze

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 $51 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.

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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 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 25 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. Monastery of Sorelle Clarisse and Antinori nel Chianti Classico are other places to visit while you're in town.

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.