A vineyard with rows of grapevines, a hill with trees, and a building in the background.

San Casciano in Val di Pesa Vacation Rentals

Q: 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.

Dates

November 2026

December 2026

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

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

San Casciano in Val di Pesa

Justyna

￥28,422 total

includes taxes & fees

Nov 23 - Nov 24

An outdoor dining area with tables and chairs, covered by umbrellas, overlooking a scenic landscape.

2. B&B La Fonte del Machiavelli

San Casciano in Val di Pesa

Stella

￥20,839 total

includes taxes & fees

Nov 9 - Nov 10

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

San Casciano in Val di Pesa

Erick

￥16,562 total

includes taxes & fees

Nov 22 - Nov 23

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

Toscana

Kim

A garden with a lawn, three white lounge chairs, and a pergola.

5. Apartment House with garden Tuscany Chianti , Florence 15km.

Toscana

Robert M.

￥28,785 total

includes taxes & fees

Nov 21 - Nov 22

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

San Casciano in Val di Pesa

￥121,959 total

includes taxes & fees

Nov 9 - Nov 10

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

San Casciano in Val di Pesa

￥472,141 total

includes taxes & fees

Nov 9 - Nov 10

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

San Casciano in Val di Pesa

￥124,866 total

includes taxes & fees

Nov 9 - Nov 10

A stone building with a patio area featuring a table and chairs under a large umbrella.

9. Relais Villa Olmo - Place of Charme

Impruneta

Michael

￥16,166 total

includes taxes & fees

Nov 26 - Nov 27

A tented room with a bed, curtains, and a view of an outdoor deck.

10. hu Firenze Certosa camping in town

Impruneta

Ana María

￥8,875 total

includes taxes & fees

Nov 9 - Nov 10

A modern house with glass walls and a patio area.

11. Marignolle Relais and Charme

Florence

Honey

￥24,680 total

includes taxes & fees

Nov 23 - Nov 24

A terrace with outdoor seating, a view of the city, and a clock tower in the background.

12. Palazzo Alfieri Residenza d’epoca - Place of Charme

Historic Centre of Florence

robert

￥28,371 total

includes taxes & fees

Nov 23 - Nov 24

A balcony with wicker furniture, overlooking a historic square with a prominent tower and a clock.

13. Relais Piazza Signoria

Historic Centre of Florence

David

￥20,021 total

includes taxes & fees

Dec 3 - Dec 4

A historic building with ornate iron gates, potted plants, and a visible staircase leading to an upper floor.

14. Signoria Collection

Historic Centre of Florence

SCOTT

￥20,162 total

includes taxes & fees

Nov 10 - Nov 11

A building with multiple windows, a balcony with balustrade, and storefronts with awnings.

15. Anchor Santa Croce

Historic Centre of Florence

Adina

￥18,597 total

includes taxes & fees

Nov 9 - Nov 10

A modern bedroom with a wooden ceiling, a bed with a white headboard, a beige sofa, and a glass-enclosed shower area with marble walls.

16. Residenza La Musa Amarcord

Historic Centre of Florence

Amy

￥17,219 total

includes taxes & fees

Nov 18 - Nov 19

A historic building with arched windows and a clock, located in a busy urban area with pedestrians.

17. Residenza Della Signoria

Historic Centre of Florence

Marlies

￥24,411 total

includes taxes & fees

Nov 24 - Nov 25

A table with breakfast items, a vase with flowers, and a view of a cityscape with a dome and tower.

18. Relais Luce Florence

Historic Centre of Florence

George

￥22,311 total

includes taxes & fees

Dec 3 - Dec 4

A hotel room with two beds, a chandelier, a window with curtains, and a view of the outside.

19. Affittacamere Alba

Historic Centre of Florence

Kim

￥17,074 total

includes taxes & fees

Nov 22 - Nov 23

An outdoor dining area with a table set for two, surrounded by chairs, a potted plant, and a view of a building with a staircase.

20. Serristori Palace Residence

Historic Centre of Florence

Christina

￥19,395 total

includes taxes & fees

Nov 23 - Nov 24

View all properties

Find vacation rentals that suit your style

Top San Casciano in Val di Pesa Hotel Reviews

A building with a courtyard, arched entrance, and surrounding trees.

Villa il Poggiale - Dimora Storica

San Casciano in Val di Pesa

10/10 Excellent

We are very frequent travelers who have never been to the Villa il Poggiale before and loved it. We visited in late September - not too hot and the evenings were cool. Perfect time to go. Federica, Irene, and the entire staff were absolutely wonderful from arranging our to/from airport transportation to making us feel at home. The grounds were lovely, although the pool was not heated in late September. We had breakfast everyday at the Villa - the chef does a wonderful job. They have a...

William

A spacious living area with a large window, a sofa, a green armchair, and a patterned armchair.

Salvadonica - Borgo del Chianti

San Casciano in Val di Pesa

10/10 Excellent

Sarah

A poolside area with outdoor seating and umbrellas, overlooking a scenic landscape.

Villa I Barronci Resort & Spa

San Casciano in Val di Pesa

10/10 Excellent

Limited transportation and the taxis were extremely expensive they will charge 165 euros one way for 30 minute drive. If you plan to go to Tuscany you need a car btw most cars are manual I don’t know how to drive it so I was stuck in the hotel for few days. To use public transportation you need to walk 39 minutes and is a lil dangerous because they don’t have side walk in the 15minutes from your trip.

Lourdes

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

San Casciano in Val di Pesa

10/10 Excellent

Erick

A courtyard with a large tree, a building with a yellow facade, and potted plants.

Calzaiolo

San Casciano in Val di Pesa

10/10 Excellent

Hotel Calzaiolo is WONDERFUL! I had a very restful time there. Antonietta is a kind, charming owner, and was so sweet and helpful to me. She even had a taxi deliver a work bag for me after I forgot it in my hotel room! Speaking of the room, it was charming and perfect, with a very cool wardrobe, and wood ceilings that overflowed with rustic style. If you're looking a for quiet, restful hotel (just 25 minutes outside of the hustle-and-bustle of downtown Florence), I highly recommend Hotel...

Jesse

A building with a staircase, potted plants, and a garden area.

Art Hotel Villa Agape - Place of Charme

Oltrarno

10/10 Excellent

Amazing in every way. The beauty of waking around is unlike any other. When we got there after a long day of traveling we had just missed the lunchtime to eat, and when went to shower the handle broke off- this is not a complaint. First they extended lunch without being asked and fixed the shower within minutes. From there on everything was amazing. Take time to eat the incredible breakfast in the garden, watch the breathtaking sunset in the back it’s incredible. Alessio- does it all he was...

John

A spacious living room with a large grey sofa, yellow armchairs, and a chandelier.

Hotel Horto Convento

Historic Centre of Florence

10/10 Excellent

Jassiel

A grand lobby with high ceilings, ornate columns, and a grand piano. Tables and chairs are arranged for guests.

Bernini Palace

Historic Centre of Florence

10/10 Excellent

Sarah

A modern interior with a glass elevator, a seating area with orange cushions, and a bookshelf filled with books.

Hotel Milu Florence

Historic Centre of Florence

10/10 Excellent

What a fantastic experience at Milu! To start, the staff was friendly and made us feel at home right away. Our room was clean and quiet, with the most amazing shower! We enjoyed the breakfast on the patio and found it to be a very satisfying way to start the day. The hotel maintained a relaxed feel while still being vibrant - colorful, modern art and design to enjoy while relaxing with a cup of tea from the open library. We would definitely stay again, thanks Milu for a great experience!

Kelly

The entrance to Hotel Spadaï Firenze with a modern design, including a reception desk and a chandelier.

Hotel Spadai

Historic Centre of Florence

10/10 Excellent

Richard

A hotel entrance with a double door, a reception desk, and a sign indicating the hotel name.

Ponte Vecchio Suites & Spa

Historic Centre of Florence

10/10 Excellent

This boutique hotel was absolutely wonderful! Amazing location, cold AC, incredibly comfy beds, huge and modern bathroom, free breakfast and appertivo, and a convenient spa. We truly enjoyed our stay here! The best part was the attentive staff who reached out before our stay and helped us throughout- giving restaurant recommendations as well as booking reservations and tours for us. Special shout out to Adriano and Olga, two amazing staff members who assisted us during our trip.

Anonymous traveler

A view from a window overlooking a busy square with historic buildings, a carousel, and a café table with a book and cup.

Hotel Pendini

Historic Centre of Florence

10/10 Excellent

William

A balcony with white cushions and a railing overlooking a river with a bridge.

Hotel degli Orafi

Historic Centre of Florence

10/10 Excellent

damian

An outdoor terrace with tables and chairs, candles, and a decorative silver bowl with bottles.

Hotel Santa Maria Novella

Historic Centre of Florence

10/10 Excellent

Nick

A terrace with tables and chairs overlooking a river, with historic buildings in the background.

Hotel Lungarno - Lungarno Collection

Historic Centre of Florence

10/10 Excellent

I cant say enough about the hotel! When we arrived in a taxi we did not realize the taxi did not accept credit cards. We were a bit stressed as we had just traveled over 15 hours. Imran, the doorman came to our rescue and without any effort on our part, pulled out his wallet and paid for our taxi. We then exchanged cash in the hotel and promptly repaid him. Check in was prompt and professional. The room was outstanding! Clean, elegant, stocked with everything and more we would need and just...

Kathy

A historic building with arched windows and red flags.

Hotel Calimala Florence

Historic Centre of Florence

10/10 Excellent

Josefita

A table with breakfast items and a vase of flowers on a terrace overlooking a cityscape with historic buildings and a tower.

Hotel L'Orologio Firenze

Historic Centre of Florence

10/10 Excellent

Anonymous traveler

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:

View our selection of featured holiday rentals in San Casciano in Val di Pesa
Use the map to find apartments and other holiday homes in the San Casciano in Val di Pesa neighbourhood you prefer
Enter your travel dates to view the best deals on holiday rentals in San Casciano in Val di Pesa while they last

Look no further and take a look at our great range of rental properties in San Casciano in Val di Pesa!

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 25 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.

Explore a world of travel with Expedia

Flights to Florence
Standard Link for Flights to Florence

Tuscany Vacations
Standard Link for Tuscany Vacations

San Casciano in Val di Pesa Vacation Rentals

Change your mind

Treat yourself

Be picky

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

5. Apartment House with garden Tuscany Chianti , Florence 15km.

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

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

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

9. Relais Villa Olmo - Place of Charme

10. hu Firenze Certosa camping in town

11. Marignolle Relais and Charme

12. Palazzo Alfieri Residenza d’epoca - Place of Charme

13. Relais Piazza Signoria

14. Signoria Collection

15. Anchor Santa Croce

16. Residenza La Musa Amarcord

17. Residenza Della Signoria

18. Relais Luce Florence

19. Affittacamere Alba

20. Serristori Palace Residence

Find vacation rentals that suit your style

Top San Casciano in Val di Pesa Hotel Reviews

Villa il Poggiale - Dimora Storica

10/10 Excellent

Find out more about San Casciano in Val di Pesa

Frequently Asked Questions

Are there vacation rentals in San Casciano in Val di Pesa?

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

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

What can I see and do in San Casciano in Val di Pesa?

What are vacation rentals like in San Casciano in Val di Pesa?

Explore a world of travel with Expedia