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

Holiday Rentals in San Casciano in Val di Pesa

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for San Casciano in Val di Pesa holiday 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, (109 reviews)
"Food was amazing, we love how quiet and relaxing it was"
United States
Justyna
The price is €161
includes taxes & fees
23 Nov - 24 Nov
Villa il Fedino
A pool area with a view of rolling hills and a clear sky.

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, (94 reviews)
"The view is unique. Perfect location for a romantic trip."
United States
Stella
The price is €118
includes taxes & fees
15 Nov - 16 Nov
B&B La Fonte del Machiavelli
Terrace/patio

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, (29 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 €105
includes taxes & fees
22 Nov - 23 Nov
B&B Le Dimore di Mezza Costa - Home Restaurant & Cooking Classes
An outdoor patio with a table, chairs, and a view of a landscape.

4. country house with garden ,pool,children's play area ,Tuscany,15 from Florence

country house with garden ,pool,children's play area ,Tuscany,15 from Florence
Toscana
9.8 out of 10, Exceptional, (83 reviews)
"The hostess Sonia was fabulous."
United States
Kim
The price is €140
includes taxes & fees
15 Nov - 16 Nov
country house with garden ,pool,children's play area ,Tuscany,15 from Florence
A swimming pool with clear blue water, surrounded by trees and a wooden deck.

5. 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.
The price is €141
includes taxes & fees
16 Nov - 17 Nov
Apartment House with garden Tuscany Chianti , Florence 15km.
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 €2,674
includes taxes & fees
15 Nov - 16 Nov
Portion of Villa Il Conventino with Pool and Wi-Fi
Pool

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 €691
includes taxes & fees
15 Nov - 16 Nov
Apartment 'Mini in Chianti' with Shared Pool, Wi-Fi and Air Conditioning
Pool

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
The price is €707
includes taxes & fees
15 Nov - 16 Nov
Cottage in Chianti Barn with Shared Pool, Wi-Fi, and Air Conditioning
A villa with multiple bedrooms, a swimming pool, and a garden.

9. Relais Villa Olmo - Place of Charme

Relais Villa Olmo - Place of Charme
Impruneta
9.6 out of 10, Exceptional, (277 reviews)
"Great property and staff. Highly recommend!"
United States
Michael
The price is €92
includes taxes & fees
29 Nov - 30 Nov
Relais Villa Olmo - Place of Charme
A historic building with ornate iron gates, potted plants, and a visible staircase leading to an upper floor.

10. Signoria Collection

Signoria Collection
Historic Centre of Florence
9.8 out of 10, Exceptional, (24 reviews)
"The property location was ideal for visiting the landmarks, churches and museums."
United States
SCOTT
The price is €116
includes taxes & fees
15 Nov - 16 Nov
Signoria Collection
A swimming pool with people enjoying the water, a wooden deck, and a covered seating area.

11. hu Firenze Certosa camping in town

hu Firenze Certosa camping in town
Impruneta
8.6 out of 10, Excellent, (128 reviews)
"Very helpful staff and comfortable affordable stay"
United States
Ana María
The price is €50
includes taxes & fees
15 Nov - 16 Nov
hu Firenze Certosa camping in town
A building with multiple windows, a balcony with balustrade, and storefronts with awnings.

12. Anchor Santa Croce

Anchor Santa Croce
Historic Centre of Florence
9.8 out of 10, Exceptional, (9 reviews)
"Amazing place to stay. Clean, close to main touristic attractions in Florence."
Canada
Adina
The price is €109
includes taxes & fees
16 Nov - 17 Nov
Anchor Santa Croce
A rural landscape with a house surrounded by lush greenery and a small pool.

13. Marignolle Relais and Charme

Marignolle Relais and Charme
Florence
9.2 out of 10, Wonderful, (94 reviews)
"The Marignolle Relais & Charme is absolutely gorgeous. The rooms are beautifully decorated and everything is so clean. The grounds are well maintained and the pool area is stunning. We loved our two day stay and heartily recommend it. Stay here you’ll love it!!!"
Canada
Honey
The price is €149
includes taxes & fees
29 Nov - 30 Nov
Marignolle Relais and Charme
An outdoor dining area with multiple tables and chairs, surrounded by plants and hanging lights.

14. Hu Firenze Camping In Town

Hu Firenze Camping In Town
Florence
8.8 out of 10, Excellent, (1,808 reviews)
"Loved the place. Our cabin was perfect & it’s right on a bus line into town."
United States
Debra
The price is €58
includes taxes & fees
22 Nov - 23 Nov
Hu Firenze Camping In Town
A balcony with a table, wine glasses, and a bottle, overlooking a historic building with a clock tower and another tower.

15. Relais Piazza Signoria

Relais Piazza Signoria
Historic Centre of Florence
9.6 out of 10, Exceptional, (899 reviews)
"Amazing location lots of space and very comfortable. Would go back for sure"
Canada
Paul
The price is €113
includes taxes & fees
3 Dec - 4 Dec
Relais Piazza Signoria
A stone building with a covered patio, a table with chairs, and a hanging plant.

16. Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (82 reviews)
"Amazing property and room, only issue is it’s very understaffed so it’s hard to get anything without chasing down workers. They also don’t stay on the property so after like 11pm you’re on your own. Besides that it was a wonderful location and very peaceful."
United States
Gage
The price is €287
includes taxes & fees
28 Nov - 29 Nov
Terre di Baccio
A restaurant with a rustic interior, featuring exposed brick walls, wooden beams, and a long counter with blue upholstered chairs.

17. Residenza La Musa Amarcord

Residenza La Musa Amarcord
Historic Centre of Florence
10.0 out of 10, Exceptional, (184 reviews)
"Beautiful room and property"
United States
Amy
The price is €93
includes taxes & fees
19 Nov - 20 Nov
Residenza La Musa Amarcord
A view of a dome and tower from a balcony overlooking a body of water and mountains.

18. Teatro Luxury Apartments Firenze - Starhotels Collezione

Teatro Luxury Apartments Firenze - Starhotels Collezione
Historic Centre of Florence
9.8 out of 10, Exceptional, (156 reviews)
"Great property!"
United States
Jahzier
The price is €182
includes taxes & fees
22 Nov - 23 Nov
Teatro Luxury Apartments Firenze - Starhotels Collezione
A wooden table with drinks and snacks on a balcony overlooking a cityscape with a prominent dome building.

19. Novella House

Novella House
Historic Centre of Florence
9.0 out of 10, Wonderful, (364 reviews)
"A beautiful place with an amazing staff and everything you need. Would definitely stay here again and would recommend it to everyone!"
United States
Zeus
The price is €87
includes taxes & fees
15 Dec - 16 Dec
Novella House
A hallway with a white door at the end, flanked by two large windows with black frames and wall-mounted lamps.

20. Nove Guest House

Nove Guest House
Historic Centre of Florence
10.0 out of 10, Exceptional, (103 reviews)
"I will definitely stay here again if I’m back in Florence. The place is very nice, clean and the staff is great! The sites are all within walking distance."
United States
Carson
The price is €104
includes taxes & fees
17 Nov - 18 Nov
Nove Guest House
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

Radisson Blu Hotel, Florence

Radisson Blu Hotel, Florence

10/10 Excellent
"Great hotel. Great service."
Juan 4-night trip
Posted 14 hours ago
Radisson Blu Hotel, Florence

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 €50 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?

Villa La Stella - Casa per Ferie: This holiday home rental outside of 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 holiday rental also comes with free parking to give you added peace of mind.

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

Choose from 25 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 Piazza del Duomo 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.