San Casciano in Val di Pesa Vacation Rentals from ￥13,488: Search Short-Term Rentals

Q: What's the top vacation rental in San Casciano in Val di Pesa?

Villa La Stella - Casa per Ferie : This vacation home rental 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.

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Our top choices for San Casciano in Val di Pesa vacation rentals

1. Villa il Fedino

San Casciano in Val di Pesa

"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...

Nilesh

￥42,346 total

includes taxes & fees

Aug 17 - Aug 18

2. B&B La Fonte del Machiavelli

San Casciano in Val di Pesa

Ruben

￥21,302 total

includes taxes & fees

Sep 7 - Sep 8

3. B&B Le Dimore di Mezza Costa - Home Restaurant & Cooking Classes

San Casciano in Val di Pesa

Raymundo

￥22,690 total

includes taxes & fees

Aug 18 - Aug 19

4. Tenuta Branca - Podere Apartment with Pool and Terrace in Chianti

San Casciano in Val di Pesa

￥62,002 total

includes taxes & fees

Aug 30 - Aug 31

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

San Casciano in Val di Pesa

￥651,669 total

includes taxes & fees

Aug 13 - Aug 14

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

San Casciano in Val di Pesa

7. Villa 'Molino' with Private Pool, Private Terrace and Wi-Fi

Mercatale Val Di Pesa

￥252,921 total

includes taxes & fees

Aug 23 - Aug 24

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

San Casciano in Val di Pesa

￥179,978 total

includes taxes & fees

Aug 18 - Aug 19

9. I Parigi Corbinelli

Florence

Stefano

￥22,576 total

includes taxes & fees

Aug 13 - Aug 14

Deluxe Double Room (1° floor) | Egyptian cotton sheets, premium bedding, down comforters

10. Sette Angeli Rooms

Historic Centre of Florence

VISHAL

￥15,350 total

includes taxes & fees

Aug 13 - Aug 14

11. hu Firenze Certosa camping in town

Impruneta

Jessica

￥9,456 total

includes taxes & fees

Sep 9 - Sep 10

12. La Senesina, Monteriggioni, Siena. In the best countryside of Tuscany !

Siena

Robyn D.

￥38,934 total

includes taxes & fees

Aug 18 - Aug 19

13. Domus il Palio B&B

Ravacciano

Alissia

￥13,202 total

includes taxes & fees

Aug 11 - Aug 12

14. Antico Borgo il Cardino

San Gimignano

Craig

￥30,139 total

includes taxes & fees

Sep 6 - Sep 7

15. Villa San Filippo

Barberino Tavarnelle

Nadia

￥20,012 total

includes taxes & fees

Sep 7 - Sep 8

16. Palazzo al Torrione 2

San Gimignano City Centre

Angel

￥24,302 total

includes taxes & fees

Aug 16 - Aug 17

17. Chianti Village Morrocco

Barberino Tavarnelle

Chris

￥17,953 total

includes taxes & fees

Sep 1 - Sep 2

18. Borgo Argenina

Gaiole in Chianti

Sabatino

￥58,109 total

includes taxes & fees

Aug 12 - Aug 13

19. Relais Villa Olmo

Impruneta

Rupert

￥26,544 total

includes taxes & fees

Aug 30 - Aug 31

20. Terre di Baccio

Greve in Chianti

"We had a wonderful experience! The staff was kind and very helpful. Our room was stunning and very spacious for a family of 5! The breakfast was amazing, and all of the activities on site were very fun - we especially enjoyed the cooking class! I would absolutely love to return here. I recommend looking into and booking on-site activities in advance so you can get the most out of your experience!"

Julia

￥54,835 total

includes taxes & fees

Aug 13 - Aug 14

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Top San Casciano in Val di Pesa Hotel Reviews

The Social Hub Florence Lavagnini

10/10 Excellent

"Awesome spot"

Palazzo Montebello

8/10 Good

"I traveled with my husband and daughter and stayed 4 nights from 7/25-7/29. I had requested earlier check-in by contacting the hotel directly through Expedia as long hours in the flight and then, train. The hotel staff indicated they didn’t receive my message. They made us wait for 2.5 hours. The lady who was at the reception desk wasn’t really friendly. She also forgot about us after told us to wait. I went to ask her about our room at 2:45pm, she started asking for my name again. I also didn’t appreciate her talking with her colleague in Italian while attending me. The hotel was beautiful. Our room was nice though waste of space with a long closet. The air conditioning wasn’t working properly as room would not get cool enough. When asked for a fan, they didn’t provide one as not available. They told me that we can change the room but that would cause major inconvenience. The room doesn’t have an iron. It is provided based on the availability. The front desk staff on the subsequent days were friendly and helpful. The hotel is about 15 mins walk from the train station and 25-30 mins from Duomo."

Plus Florence - Hostel

10/10 Excellent

"Wasnt sure what to expect from a hostel but this was great. Triple room with private bathroom was spotlessly clean. Location excellent - 15 mins walk from Firenze SMN train station and the Duomo area. Amenities were great - outdoor pool and bar area was excellent for socialising. Bar prices reasonable. Breakfast was excellent. Cooked breakfast, cereals, continentals etc. great value. Would definately recommend."

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

10/10 Excellent

"Our family of 18 stayed at the Villa this July (2026) and could not have been more pleased with everything associated with our stay. Jacopo and Beatrice truly are first class hosts. They helped us book 3 vehicles that were dropped off and picked up directly at the Villa which was a great time saver. They also provided a grocery shopping service so that we had drinks and snacks at the villa when we arrived.The meal service was truly fantastic! We opted for the Welcome dinner and the Florentine BBQ, both of which were great. We visited a lot of places while in Italy but the family dinners at sunset were among our favorites.The Villa was beautiful and spacious. The grandkids really enjoyed the open spaces and the pool. The views from the back deck of the surrounding Tuscan countryside were also very special. We even got to see hot air balloons on a few occasions. The relative close proximity to Firenze was also clutch for day trips on high-speed trains. There is a good reason why this Villa won the VRBO Vacation Rental of the Year. You simply cannot go wrong here. I am very thankful for the memories that will last a lifetime and role this villa and the hosts played in making that happen!"

Find out more about San Casciano in Val di Pesa

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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 rental 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 29 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 Cathedral of Santa Maria del Fiore 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.

San Casciano in Val di Pesa Vacation Rentals

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Check prices for these dates

Our top choices for San Casciano in Val di Pesa vacation rentals

1. Villa il Fedino

2. B&B La Fonte del Machiavelli

3. B&B Le Dimore di Mezza Costa - Home Restaurant & Cooking Classes

4. Tenuta Branca - Podere Apartment with Pool and Terrace in Chianti

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

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

7. Villa 'Molino' with Private Pool, Private Terrace and Wi-Fi

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

9. I Parigi Corbinelli

10. Sette Angeli Rooms

11. hu Firenze Certosa camping in town

12. La Senesina, Monteriggioni, Siena. In the best countryside of Tuscany !

13. Domus il Palio B&B

14. Antico Borgo il Cardino

15. Villa San Filippo

16. Palazzo al Torrione 2

17. Chianti Village Morrocco

18. Borgo Argenina

19. Relais Villa Olmo

20. Terre di Baccio

Find vacation rentals that suit your style

Top San Casciano in Val di Pesa Hotel Reviews

The Social Hub Florence Lavagnini

Find out more about San Casciano in Val di Pesa

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