Photo by Ashley Robinson
San Casciano in Val di Pesa villas
We found 225 villas — enter your dates for availability
Explore San Casciano in Val di Pesa villa rentals
Charming Villa Torre in Chianti, 8 ensuite bedrooms, pool, Florence, Wi-Fi, A/C.
Sleeps 18 · 9 bedrooms · 8+ bathrooms
1010 out of 10
Exceptionalexceptional
115 reviews(115 reviews)
Casale Tagliafune,a XV century's Country Villa near Florence with vineyards view
Sleeps 10 · 5 bedrooms · 5 bathrooms
1010 out of 10
Exceptionalexceptional
57 reviews(57 reviews)
FABULOUS 9BR-8.5BA VILLA W PRIVATE HEATED POOL, IN PRIME LOCATION NEAR FLORENCE!
Sleeps 18 · 9 bedrooms · 8+ bathrooms
1010 out of 10
Exceptionalexceptional
45 reviews(45 reviews)
Villa Lacustre: A characteristic and welcoming two-story villa in the characteristic style of the Tuscan countryside, with Free WI-FI.
Sleeps 12 · 4 bedrooms · 3+ bathrooms
1010 out of 10
Exceptionalexceptional
13 reviews(13 reviews)
Charming Villa w/ pool nestled in Chianti vineyards, with AC, close to Florence
Sleeps 10 · 5 bedrooms · 4+ bathrooms
9.69.6 out of 10
Exceptionalexceptional
49 reviews(49 reviews)
Chianti family villa, 5 bedrooms, infinity pool, A/C, EV charger, BBQ, 360° view
Sleeps 10 · 5 bedrooms · 4+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
34 reviews(34 reviews)
Top rated villa rentals - San Casciano in Val di Pesa
Superb Villa
1010 out of 10
Exceptionalexceptional
57 reviews(57 reviews)
The villa was fantastic for our family (4 adults and 2 kids). It’s a huge place and the pool was used every day (17m long!). Drive is bumpy but not bad at all. If you’re thinking about booking, just do it and the place is a credit to its owner Loredana.
Jonathan G.
Stayed Aug 2025
Heavenly
1010 out of 10
Exceptionalexceptional
54 reviews(54 reviews)
So peaceful well equipped villa absolutely loved it .
helen J.
Stayed Jun 2025
Excellent Villa
1010 out of 10
Exceptionalexceptional
45 reviews(45 reviews)
What a WONDERFUL WEEK!
Danielle M.
Stayed Apr 2025
Perfect with kids
1010 out of 10
Exceptionalexceptional
115 reviews(115 reviews)
We were 5 teens and 2 adults. The house was great - so much space, all the bedrooms were a nice size with en-suites, the pool table was very well used, there was so much to do in the house, the kitchen was very well stocked for cooking a few meals, and there was a beautiful view from the terrace. We would definitely stay again.
Daniel G.
Stayed Oct 2024
Lovely house in amazing location
1010 out of 10
Exceptionalexceptional
36 reviews(36 reviews)
We had a wonderful time at Archipettoli. It is a truly unbeatable location set at the end of a track with amazing views all around. Every bit of the garden is beautiful and well thought out with plenty of places to sit and enjoy the Tuscan countryside. The pool is sparklingly clean and surrounded by lovely planting and plenty of loungers. Several spots are ideal for eating al fresco and comfortable chairs for reading in. The house itself has elegant bedrooms with nice furniture and clean generous bathrooms. The only bit of the house that was a little underwhelming was the kitchen which, due to the layout of cooker/dishwasher etc was a bit tight for more than one person to cook in, and the sitting room, which wasn’t very inviting to spend an evening in when it was too cold to sit outside. These would absolutely not stop me from visiting again! Everything else wonderful and I very much hope to go again soon.
Catherine H.
Stayed Aug 2023
Beautiful villa, lovely pool
1010 out of 10
Exceptionalexceptional
13 reviews(13 reviews)
Great quality. Everything was as we expected. Our flight was a late one, so the Property Manager met us at a nearby petrol station and led us to the property. This was especially appreciated since the road from main road to villa was very rough. Marco was really helpful throughout our stay. Check in and out was easy. Marco booked us tables at the local pizzeria a couple of times and gave us recommendations for shopping etc. Beautiful area, great scenery and fascinating culture in Florence. All in all a great week
Michael O.
Stayed Jul 2023
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Frequently asked questions
Are there any holiday villa rentals in San Casciano in Val di Pesa?
Choose one of our 225 villa rentals in San Casciano in Val di Pesa and you'll have an ideal base for your next family or group adventure. Calzaiolo, Massanera and San Quirico in Collina are among the city's most popular neighbourhoods.
How much does it cost to stay in a villa rental in San Casciano in Val di Pesa?
Where you stay, when you want to travel and the length of your escape will determine how much you pay for a villa rental in San Casciano in Val di Pesa. Key in your travel details on Vrbo to compare options and then pick the best one for you.
When is the best time to rent a villa in San Casciano in Val di Pesa?
It can all depend on the weather conditions you like most, among other factors. Many people visiting Chianti Region book a San Casciano in Val di Pesa villa rental in April, when average temperatures range from 6ºC (43ºF) to 18ºC (64ºF).
Where can I rent a San Casciano in Val di Pesa villa with great views?
Vrbo has a range of character-filled villa rentals in San Casciano in Val di Pesa, including escapes with views of historic areas. In between seeing the sights, kick back and gaze at vistas that are an attraction in themselves.
Can I book a luxury villa in San Casciano in Val di Pesa?
Take your holiday to the next level with one of our villa rentals in San Casciano in Val di Pesa. Offering premium conveniences such as fully-equipped kitchens, advanced in-home entertainment systems and quality furnishings, you and your guests will feel like A-listers. Use our filter tool to display the properties with first-rate perks like hot tubs and pools for that added layer of opulence and luxury.
What are the top things to do in San Casciano in Val di Pesa?
One of the first things to do after locking in your villa rental is to fill your itinerary with awesome activities and sights. There's loads of them in San Casciano in Val di Pesa, with some of the leading family-friendly attractions including Cathedral of Santa Maria del Fiore, Ponte Vecchio and Uffizi Gallery.
Why should I book my villa holiday with Vrbo?
You can book your villa rental with peace of mind on Vrbo. From the second you book and pay for your reservation until your holiday is done, we'll be by your side every step of the way. It's part of our Book with Confidence Guarantee. If you have to cancel, we've got you covered too. Many of our properties offer flexible cancellation policies In addition, our free loyalty programme, One Key™, lets you collect and redeem OneKeyCash™* on eligible bookings on Vrbo. *OneKeyCash disclaimer - OneKeyCash is not redeemable for cash and can only be used on Vrbo.