San Casciano in Val di Pesa Holiday Rentals from NZ$100: Search Short-Term Rentals

Q: 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.

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

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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

San Casciano in Val di Pesa

Justyna

includes taxes & fees

23 Nov - 24 Nov

A pool area with a view of rolling hills and a clear sky.

2. B&B La Fonte del Machiavelli

San Casciano in Val di Pesa

Stella

includes taxes & fees

15 Nov - 16 Nov

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

San Casciano in Val di Pesa

Erick

includes taxes & fees

26 Nov - 27 Nov

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

includes taxes & fees

15 Nov - 16 Nov

A swimming pool with clear blue water, surrounded by trees and a wooden deck.

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

Toscana

Robert M.

includes taxes & fees

21 Nov - 22 Nov

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

San Casciano in Val di Pesa

includes taxes & fees

25 Nov - 26 Nov

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

San Casciano in Val di Pesa

includes taxes & fees

15 Nov - 16 Nov

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

San Casciano in Val di Pesa

includes taxes & fees

15 Nov - 16 Nov

A villa with multiple bedrooms, a swimming pool, and a garden.

9. Relais Villa Olmo - Place of Charme

Impruneta

Michael

includes taxes & fees

29 Nov - 30 Nov

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

10. Signoria Collection

Historic Centre of Florence

SCOTT

includes taxes & fees

15 Nov - 16 Nov

A swimming pool with people enjoying the water, a wooden deck, and a covered seating area.

11. hu Firenze Certosa camping in town

Impruneta

Ana María

includes taxes & fees

15 Nov - 16 Nov

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

12. Anchor Santa Croce

Historic Centre of Florence

Adina

includes taxes & fees

16 Nov - 17 Nov

A rural landscape with a house surrounded by lush greenery and a small pool.

13. Marignolle Relais and Charme

Florence

Honey

includes taxes & fees

9 Dec - 10 Dec

An outdoor dining area with multiple tables and chairs, surrounded by plants and hanging lights.

14. Hu Firenze Camping In Town

Florence

Debra

includes taxes & fees

15 Dec - 16 Dec

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

Historic Centre of Florence

Paul

includes taxes & fees

3 Dec - 4 Dec

A stone building with a covered patio, a table with chairs, and a hanging plant.

16. Terre di Baccio

Greve in Chianti

Gage

includes taxes & fees

15 Nov - 16 Nov

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

Historic Centre of Florence

Amy

includes taxes & fees

18 Nov - 19 Nov

A rooftop pool with a clear view of historic buildings and mountains in the background.

18. Teatro Luxury Apartments Firenze - Starhotels Collezione

Historic Centre of Florence

Jahzier

includes taxes & fees

29 Nov - 30 Nov

A wooden table with drinks and snacks on a balcony overlooking a cityscape with a prominent dome building.

19. Novella House

Historic Centre of Florence

Zeus

includes taxes & fees

15 Dec - 16 Dec

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

Historic Centre of Florence

Carson

includes taxes & fees

17 Nov - 18 Nov

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Find holiday rentals that suit your style

Top San Casciano in Val di Pesa Hotel Reviews

A four-poster bed with a floral canopy, a wooden floor, a bedside table with a book and a cup, and a television on a shelf.

Hotel David

Oltrarno

10/10 Excellent

Allan

A formal garden with statues, neatly trimmed hedges, and a stone staircase.

Art Hotel Villa Agape - Place of Charme

Oltrarno

10/10 Excellent

Amazing experience staying here! The villa is stunning you feel like you’re living as royalty. The gardens are beautiful despite the extreme heat of Italy. Don’t miss a sunset in the gardens. We had dinner twice, both nights had lovely food and service. The Buffett breakfast is definitely worth adding to your stay. The shuttle that takes you into town is such a good idea. Even though we had a car we didn’t have to worry about trying to park near the city to explore. Lovely Villa, thank...

Syvahna

A multi-story building with a symmetrical facade, large windows, and a central entrance with steps.

Il Malaspina - Place of Charme

Historic Centre of Florence

10/10 Excellent

We stayed for a week in July 2026. The hotel was recently refurbished so everything is new. It was the middle of a heat wave and the aircon was fantastic, almost too cold (but the staff can adjust further if needed). The family room was spacious for the three of us. The usual amenities are available - but they provided a steamer rather than ironing board and iron (I have not asked if this was available). Has USB A and USB C charging ports in the room. It has lift access so no lugging suitcases...

Pak Leng

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

Hotel Horto Convento

Historic Centre of Florence

10/10 Excellent

Kevin

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

Great hotel in fantastic location. Driving in and out is a nightmare. The parking arrangement let’s it down. You have to pay them separately and their payment machine was not working so you then have to go to their office. The hotel didn’t want to know, it would be a better arrangement for their clients if the hotel took the charge and passed it on to the parking garage so that customers are not inconvenienced.

An aerial view of a villa surrounded by olive groves and vineyards, with a swimming pool and a large garden.

Villa il Poggiale - Dimora Storica

San Casciano in Val di Pesa

10/10 Excellent

Michael

A swimming pool with lounge chairs and a building with arched windows in the background.

Villa Neroli - Place of Charme

Coverciano

10/10 Excellent

Arriving at this villa was breathtaking. The immaculate gardens and beautiful structure gave a Tuscan villa feel while still being close enough by bus to the city centre. We booked a family room for 2 adults and 3 kids which was larger than expected and very comfortable, especially the bed. It had a big balcony where we could see the gardens and sunset which created a great memory. The only issue was that we couldn't easily keep the doors open to each room to allow the kids in and out as they...

Lisa

A dining area with tables set for four, large arched windows, and a view of a building with classical architecture.

Hotel Pendini

Historic Centre of Florence

10/10 Excellent

Lionel

A pool area with lounge chairs and umbrellas, surrounded by lush greenery and white flowers.

Hotel Ville sull'Arno - Preferred Hotels & Resorts

Campo di Marte

10/10 Excellent

kirsty

A historic building with a stone-paved courtyard, arched ceilings, and columns.

Loggiato dei Serviti

Historic Centre of Florence

10/10 Excellent

Ana

A terrace with a table and chairs, potted plants, and a view of a historic tower.

Hotel Calimala Florence

Historic Centre of Florence

10/10 Excellent

Kate

A hotel room with a neatly made bed, a wall-mounted lamp, and a window with curtains.

IQ Hotel Firenze

Historic Centre of Florence

10/10 Excellent

Tania

A reception area with a black reception desk, a white vase with flowers, and a staircase with a black and white checkered floor.

The Frame Hotel La Gioconda Ritrovata

Historic Centre of Florence

10/10 Excellent

Larisa

A balcony with a view of a river, buildings, and a bridge.

Hotel degli Orafi

Historic Centre of Florence

10/10 Excellent

Karen

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, 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 NZ$100 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.

San Casciano in Val di Pesa Holiday Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for San Casciano in Val di Pesa holiday 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. Portion of Villa Il Conventino with Pool and Wi-Fi

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

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

9. Relais Villa Olmo - Place of Charme

10. Signoria Collection

11. hu Firenze Certosa camping in town

12. Anchor Santa Croce

13. Marignolle Relais and Charme

14. Hu Firenze Camping In Town

15. Relais Piazza Signoria

16. Terre di Baccio

17. Residenza La Musa Amarcord

18. Teatro Luxury Apartments Firenze - Starhotels Collezione

19. Novella House

20. Nove Guest House

Find holiday rentals that suit your style

Top San Casciano in Val di Pesa Hotel Reviews

Hotel David

10/10 Excellent

Find out more about San Casciano in Val di Pesa

San Casciano in Val di Pesa holiday rentals: An excellent choice for every season

How to find incredible deals on San Casciano in Val di Pesa rentals

Frequently Asked Questions

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

What are some of the best holiday rentals that San Casciano in Val di Pesa has to offer?

How many holiday 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 holiday rentals like in San Casciano in Val di Pesa?

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