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
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

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, (105 reviews)
"Tha parking was easy on the property. It was within walking distance to the villages with shops, restaurants and cafes. The best part was the staff. The owners were incredibly helpful, friendly and made you feel like family. Breakfast outside was lovely overlooking the hills of Tuscany. We met many people and had lovely conversations with other travelers during breakfast. A gem in Tuscany."
United States
Lori
The price is ￥34,758
￥38,955 total
includes taxes & fees
Oct 19 - Oct 20
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
The price is ￥17,745
￥20,241 total
includes taxes & fees
Oct 19 - Oct 20
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, (28 reviews)
"Me and my girlfriend really did enjoy this property. Both host were very friendly and welcoming to us. We both did enjoy the feel at Home environment. We would definitely come back here on a future trip. Big shout out to the host for the wonderful cook meals. Great to know a bit about them as well."
United States
Erick
The price is ￥17,627
￥20,110 total
includes taxes & fees
Oct 7 - Oct 8
B&B Le Dimore di Mezza Costa - Home Restaurant & Cooking Classes

4. 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
The price is ￥100,958
￥112,677 total
includes taxes & fees
Oct 14 - Oct 15
Cottage in Chianti Barn with Shared Pool, Wi-Fi, and Air Conditioning
An outdoor patio with a round table, chairs, a sofa, and a potted plant.

5. Molino In Chianti - Villa with Private Pool

Molino In Chianti - Villa with Private Pool
Mercatale Val Di Pesa
The price is ￥249,247
￥249,968 total
includes taxes & fees
Sep 25 - Sep 26
Molino In Chianti - Villa with Private Pool

6. 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
The price is ￥328,374
￥497,678 total
includes taxes & fees
Oct 1 - Oct 2
Portion of Villa Il Conventino with Pool and Wi-Fi

7. 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
The price is ￥90,116
￥101,828 total
includes taxes & fees
Oct 4 - Oct 5
Apartment 'Mini in Chianti' with Shared Pool, Wi-Fi and Air Conditioning
A spacious indoor area with arched windows, wooden furniture, and hanging plants.

8. Relais Villa Olmo

Relais Villa Olmo
Impruneta
9.4 out of 10, Exceptional, (266 reviews)
"Very friendly and clean."
United States
Mohamed
The price is ￥26,828
￥30,052 total
includes taxes & fees
Oct 19 - Oct 20
Relais Villa Olmo
A water park with a pool, slides, and a wooden deck area.

9. hu Firenze Certosa camping in town

hu Firenze Certosa camping in town
Impruneta
8.4 out of 10, Very good, (106 reviews)
"Lovely location in the hills. Really nice pool and bar."
United Kingdom
Jessica
The price is ￥7,123
￥8,376 total
includes taxes & fees
Oct 12 - Oct 13
hu Firenze Certosa camping in town
A swimming pool with lounge chairs and a flag.

10. Fattoria il Milione Agriturismo

Fattoria il Milione Agriturismo
4.0 star property
Florence
8.2 out of 10, Very good, (263 reviews)
"Great location easy access to Firenze"
Canada
Donnie
The price is ￥14,049
￥17,979 total
includes taxes & fees
Sep 27 - Sep 28
Fattoria il Milione Agriturismo
A restaurant with hanging baskets of greenery, wicker furniture, and a view of the outdoors.

11. 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
The price is ￥46,278
￥51,627 total
includes taxes & fees
Sep 25 - Sep 26
Terre di Baccio
An outdoor patio with a table and chairs, surrounded by greenery and a view of distant hills.

12. Luxury Villa in the Florentine hills

Luxury Villa in the Florentine hills
Florence
9.8 out of 10, Exceptional, (150 reviews)
"The villa is a nicely restored rustic home with a beautiful landscape. I would definitely stay there again!"
United States
melissa r.
The price is ￥36,046
￥59,836 total
includes taxes & fees
Oct 12 - Oct 13
Luxury Villa in the Florentine hills
A modern bedroom with a large bed, a desk with chairs, and a bathroom visible through an open door.

13. Palazzo Mannaioni Suites

Palazzo Mannaioni Suites
4.0 star property
Historic Centre of Florence
9.2 out of 10, Wonderful, (1,174 reviews)
"Great location"
United States
Diana
The price is ￥42,158
￥48,897 total
includes taxes & fees
Oct 9 - Oct 10
Palazzo Mannaioni Suites

14. La Torre Del Cestello

La Torre Del Cestello
Historic Centre of Florence
9.2 out of 10, Wonderful, (322 reviews)
"Clean room friendly staff definitely be back"
United States
IVAN
The price is ￥34,285
￥40,236 total
includes taxes & fees
Oct 22 - Oct 23
La Torre Del Cestello
A terrace with outdoor seating, a view of the city, and a clock tower in the background.

15. Il Rivalta - Place of Charme

Il Rivalta - Place of Charme
4.0 star property
Historic Centre of Florence
9.4 out of 10, Exceptional, (625 reviews)
The price is ￥64,042
￥72,969 total
includes taxes & fees
Oct 23 - Oct 24
Il Rivalta - Place of Charme
A hotel room with a bed, a bedside table, a heater, a mirror, and a bathroom with a sink.

16. Hu Firenze Camping In Town

Hu Firenze Camping In Town
Florence
8.8 out of 10, Excellent, (1,737 reviews)
"Love this place, came back twice. Literally had all you need . The shuttle downtown is amazing, exploring with families can be chaotic this helped. The pool gets a bit crowded during peak season but still worth a visit."
United States
Ama
The price is ￥10,093
￥12,365 total
includes taxes & fees
Oct 21 - Oct 22
Hu Firenze Camping In Town
A room with a dining table, a vase of flowers, a lamp, and a view of a historic building through a window.

17. Mamo Florence - Le Farine Della Signoria Apartments

Mamo Florence - Le Farine Della Signoria Apartments
Historic Centre of Florence
8.6 out of 10, Excellent, (10 reviews)
"Amazing property with excellent views. "
United States
Karl
The price is ￥28,445
￥45,167 total
includes taxes & fees
Oct 11 - Oct 12
Mamo Florence - Le Farine Della Signoria Apartments
A dining area with a table set for two, featuring a view of greenery through a window.

18. La Locanda di Pietracupa

La Locanda di Pietracupa
Tavarnelle Val di Pesa
9.6 out of 10, Exceptional, (38 reviews)
"Great place, wonderful restaurant"
Germany
Isabell
The price is ￥26,694
￥30,085 total
includes taxes & fees
Oct 3 - Oct 4
La Locanda di Pietracupa
A wooden door with a sign, a large potted plant, and a view of a historic building.

19. La Casa del Garbo - Luxury Rooms & Suite

La Casa del Garbo - Luxury Rooms & Suite
Historic Centre of Florence
9.6 out of 10, Exceptional, (306 reviews)
"Location was incredible. Staff was incredibly helpful and accommodating. We ended up missing check in due to a late train and they were very kind to set up late check in for us last minute. Rooms were so cute and spacious. Had read some reviews about the noise from the plaza being loud, but we couldn't hear a thing. Will be staying here again when visiting Florence."
United States
Kristin
The price is ￥25,387
￥35,495 total
includes taxes & fees
Oct 21 - Oct 22
La Casa del Garbo - Luxury Rooms & Suite
A terrace with a table set for breakfast, a chair, and a large umbrella.

20. Villa La Stella - Casa per Ferie

Villa La Stella - Casa per Ferie
Le Cure
8.6 out of 10, Excellent, (254 reviews)
"It’s was great"
United States
Rocio
The price is ￥19,799
￥23,221 total
includes taxes & fees
Oct 11 - Oct 12
Villa La Stella - Casa per Ferie
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
"Room was Clean, Staff well trained. Breakfast okay. Air conditioning was very good in the rooms. A super busy hotel."
Ken 2-night trip
Posted 1 hour ago
Hotel Albani Firenze

Find out more about San Casciano in Val di Pesa

Search for holiday rentals in San Casciano in Val di Pesa on Expedia! You can easily find your home rentals, villas, holiday apartments in San Casciano in Val di Pesa using one of the methods below:

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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 24 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. Piazza di Santa Maria Novella and Piazza del Duomo 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.