San Casciano in Val di Pesa Villas from AED 555

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

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Our top choices for San Casciano in Val di Pesa villas

1. Molino In Chianti - Villa with Private Pool

Mercatale Val Di Pesa

AED 5,878 total

includes taxes & fees

18 Sep - 19 Sep

2. Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~

Impruneta

Maria H.

AED 1,865 total

includes taxes & fees

6 Oct - 7 Oct

3. Villa with Guesthouse: Private Pool, Air Conditioning, 13 Bedrooms for up to 30 Guests

Montespertoli

AED 25,447 total

includes taxes & fees

14 Oct - 15 Oct

4. Luxury Villa in the Florentine hills

Florence

melissa r.

AED 1,407 total

includes taxes & fees

12 Oct - 13 Oct

5. Rooster House, cooking classes and opera

Tavarnelle Val di Pesa

AED 555 total

includes taxes & fees

18 Sep - 19 Sep

6. Villino Tre Pini | Panoramic Private Pool, Nature & Privacy

Tavarnelle Val di Pesa

AED 3,560 total

includes taxes & fees

4 Oct - 5 Oct

7. VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

Firenze

AED 55,272 total

includes taxes & fees

17 Sep - 18 Sep

8. "Villa Bellavista" with Private Pool, Private Whirlpool & Wi-Fi

Certaldo

AED 23,409 total

includes taxes & fees

12 Oct - 13 Oct

9. Tenuta le Viste - beautiful Villa overlooking Florence

scandicci

STEPHANE B.

10. Golden Hour - wedding in Florence

Toscana

AED 13,177 total

includes taxes & fees

30 Sep - 1 Oct

11. Luxury,Charming,in true Chianti, sleeps 22 or +/- pople., with AIR-CONDITION!!!!

Montespertoli

"Amazing Property! The house was impeccably clean, with spacious bedrooms and comfortable beds. Our gracious host Nicola spoiled us with his generosity. He went beyond our expectations to ensure that our stay was perfect. He and his wife welcomed us with a delicious homemade apple cake. He drove us to the nearby town of Montespertoli to pick-up groceries and provisions. He recommended a local chef to cook for us at the villa. The meal was amazing and memorable. We will be back!"

Elise D.

AED 7,299 total

includes taxes & fees

20 Sep - 21 Sep

12. Exclusive Estate | Personal Concierge & Heated Pool

impruneta

Charles S.

AED 4,981 total

includes taxes & fees

1 Oct - 2 Oct

13. Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites

Montespertoli

AED 7,654 total

includes taxes & fees

20 Sep - 21 Sep

14. Villa Sunset, in the heart of Chianti

Greve in Chianti

elisa b.

15. Apartments Florence - Villa Fonte Morgana with pool

Impruneta

Christine B.

16. Villa Dei Pavoni - Luxury Villa on top of hills in Florence

Toscana

Leopard I.

AED 8,549 total

includes taxes & fees

30 Sep - 1 Oct

17. Villa Milani with Shared Pool, Private Terrace & Wi-Fi

Montespertoli

Scott M.

AED 12,724 total

includes taxes & fees

14 Oct - 15 Oct

18. Bagno a Ripoli, Italy. Entire accommodation: villa

Toscana

AED 3,615 total

includes taxes & fees

5 Oct - 6 Oct

19. Villa Il Signorino

GREVE IN CHIANTI

Avi A.

AED 1,907 total

includes taxes & fees

17 Sep - 18 Sep

20. My Exclusive Italy - Classic Suite in a Luxury Wine Estate

Rignano sull'Arno

AED 1,691 total

includes taxes & fees

16 Oct - 17 Oct

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Top San Casciano in Val di Pesa Hotel Reviews

Hotel Delle Nazioni

10/10 Excellent

"Loved it! Staff can help you book affordable wine tasting tour in Tuscany"

Plus Florence - Hostel

8/10 Good

"The indoor pool was undergoing maintenance and the outdoor pool closed at 7, not the 10pm advertised in the hostel’s messages after checking in. The restaurant advertises itself online as being flexible for gluten free/ vegetarian/ vegan. When sitting down and asking, nothing was completely gluten free and only the three meat dishes and one pasta dish could be made gluten free. We ate elsewhere. Clean rooms and friendly staff, good for a basic hostel stay. Air conditioning in the rooms, however it is very loud (might just be an issue in the room we stayed in). Great location for the train station."

Art Hotel Villa Agape

8/10 Good

"The room, breakfast and front counter staff were excellent. Overall was a nice experience. there was a wedding in the courtyard patio area during our stay on the first night and we couldn’t enjoy certain areas of the property. We would have liked to have been made aware of that. Instead of stumbling into their party and told it was private. Both men and the lady at the desk were extremely helpful and kind. As well as the morning breakfast lady."

Palazzo Montebello

8/10 Good

"Lovely hotel, spotlessly clean and we liked that the location was 15 mins walk away from the super busy chaos of the main tourist areas. Lots of amenities within short walk away and the walk along the river to the centre of Florence was lovely. Front desk staff were very helpful and offered great recommendations for places to eat and visit. The only downsides for us were: 1. the breakfast options which were very basic for how expensive the hotel is per night, the cooked breakfasts were not good so we had to eat elsewhere for a few days. 2. Our room was great but very much let down by the fact there was a huge window which had no cover or curtains to close which let in a lot of light as there happened to be a lamp right outside of it which shined directly in to the room. It meant our room was lit up like Times Square even in the middle of the night and we ended up having to wedge a towel over the window to try and reduce this. The window was also immediately opposite our bathroom so anyone outside could see straight in to it if they wanted to. Not sure if this is relevant for other rooms but it was very annoying for us and seems like it could be an easy fix! Overall we had a really great time and would stay again!"

Frequently asked questions

How much do villas in San Casciano in Val di Pesa cost?

Rates for villas in San Casciano in Val di Pesa range between AED 555 and AED 55,272 per night. Whatever your budget, you can find a place that suits your needs with Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.

How many villas are there in San Casciano in Val di Pesa?

You'll find 1779 villas in San Casciano in Val di Pesa. No matter if you're traveling with the kids or organizing a weekend break with your besties, Expedia can help you find the ideal base for your squad.

Why book your villa in San Casciano in Val di Pesa with Expedia?

Reserving a villa in San Casciano in Val di Pesa is as easy as working out your travel dates and choosing a place that checks your boxes. In search of something affordable or luxurious, or a stay that also offers a kitchenette? Use Expedia's search filters to narrow your results and find the ideal fit.

How can I find cheap villas in San Casciano in Val di Pesa?

Expedia is here to help you look for cheap villas in San Casciano in Val di Pesa. Use our filter tool to select amenities, budget and star rating to refine your search and find a fantastic place to stay in a couple of clicks.

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Check prices for these dates

Our top choices for San Casciano in Val di Pesa villas

1. Molino In Chianti - Villa with Private Pool

2. Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~

3. Villa with Guesthouse: Private Pool, Air Conditioning, 13 Bedrooms for up to 30 Guests

4. Luxury Villa in the Florentine hills

5. Rooster House, cooking classes and opera

6. Villino Tre Pini | Panoramic Private Pool, Nature & Privacy

7. VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

8. "Villa Bellavista" with Private Pool, Private Whirlpool & Wi-Fi

9. Tenuta le Viste - beautiful Villa overlooking Florence

10. Golden Hour - wedding in Florence

11. Luxury,Charming,in true Chianti, sleeps 22 or +/- pople., with AIR-CONDITION!!!!

12. Exclusive Estate | Personal Concierge & Heated Pool

13. Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites

14. Villa Sunset, in the heart of Chianti

15. Apartments Florence - Villa Fonte Morgana with pool

16. Villa Dei Pavoni - Luxury Villa on top of hills in Florence

17. Villa Milani with Shared Pool, Private Terrace & Wi-Fi

18. Bagno a Ripoli, Italy. Entire accommodation: villa

19. Villa Il Signorino

20. My Exclusive Italy - Classic Suite in a Luxury Wine Estate

Find vacation rentals that suit your style

Top San Casciano in Val di Pesa Hotel Reviews

Hotel Delle Nazioni

Plus Florence - Hostel

Bernini Palace

Art Hotel Villa Agape

Palazzo Montebello

"Villa Torre in Chianti" Vrbo Vacation Rental of the Year 2026- 8 bedrooms A/C

Hotel Horto Convento

c-hotels Ambasciatori

Hotel Paris

Frequently asked questions

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Search Villas in San Casciano in Val di Pesa

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for San Casciano in Val di Pesa villas

1. Molino In Chianti - Villa with Private Pool

2. Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~

3. Villa with Guesthouse: Private Pool, Air Conditioning, 13 Bedrooms for up to 30 Guests

4. Luxury Villa in the Florentine hills

5. Rooster House, cooking classes and opera

6. Villino Tre Pini | Panoramic Private Pool, Nature & Privacy

7. VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

8. "Villa Bellavista" with Private Pool, Private Whirlpool & Wi-Fi

9. Tenuta le Viste - beautiful Villa overlooking Florence

10. Golden Hour - wedding in Florence

11. Luxury,Charming,in true Chianti, sleeps 22 or +/- pople., with AIR-CONDITION!!!!

12. Exclusive Estate | Personal Concierge & Heated Pool

13. Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites

14. Villa Sunset, in the heart of Chianti

15. Apartments Florence - Villa Fonte Morgana with pool

16. Villa Dei Pavoni - Luxury Villa on top of hills in Florence

17. Villa Milani with Shared Pool, Private Terrace & Wi-Fi

18. Bagno a Ripoli, Italy. Entire accommodation: villa

19. Villa Il Signorino

20. My Exclusive Italy - Classic Suite in a Luxury Wine Estate

Find vacation rentals that suit your style

Top San Casciano in Val di Pesa Hotel Reviews

Hotel Delle Nazioni

Frequently asked questions

Explore a world of travel with Expedia