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San Chimento Holiday Rentals

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Our top choices for San Chimento holiday rentals

1. Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.8 out of 10, Exceptional, (100 reviews)
"We love this beautiful exquisitely appointed hotel in a town with unexpected treasures and great food "
United Kingdom
John
The price is NZ$291
includes taxes & fees
2 Sept - 3 Sept
Palazzo Pacini

2. Villa Montecastello

Villa Montecastello
Monteriggioni
8.0 out of 10, Very good, (3 reviews)
"Amazing stay! Teh apartment is HUGE and GORGEOUS. The whole villa is amazing. The view , unbeatable. The host , super warm. Highly recommend!"
United States
Alvaro
The price is NZ$362
includes taxes & fees
30 Aug - 31 Aug
Villa Montecastello

3. Borgo al Cerro

Borgo al Cerro
Casole d'Elsa
9.2 out of 10, Wonderful, (25 reviews)
"Väldigt vackert ställe med bra placering mitt i Toscana. Rummet var väldigt fint, men bilderna från hemsidan var finare, så jag blev lite besviken när vi väl kom in. I övrigt var komplexets omgivningar och trädgård helt fantastisk. Barnen hade roligt med pingisbor och dart och det fanns trevlig grillplats att nyttja. "
Sweden
Frida
The price is NZ$398
includes taxes & fees
4 Sept - 5 Sept
Borgo al Cerro

4. La Casetta, Casole d'Elsa, Siena. Join the real Tuscany countryside!

La Casetta, Casole d'Elsa, Siena. Join the real Tuscany countryside!
casole d'elsa siena
10.0 out of 10, Exceptional, (43 reviews)
"We stayed in this beautiful clean, fully airconditioned apartment for 12 days, perfect location for trips to the surrounding area like Siena, Florence, Monteriggioni, Volterra & San Gimignano. The apartment is situated in a peaceful Agriturismo with lots of privacy and a great swimming pool. The owners are really hospitable and you feel welcome right away. Highly recommendable."
Netherlands
Linda T.
The price is NZ$711
includes taxes & fees
12 Sept - 13 Sept
La Casetta, Casole d'Elsa, Siena. Join the real Tuscany countryside!

5. Borgo Il Poggiaccio

Borgo Il Poggiaccio
Sovicille
8.8 out of 10, Excellent, (67 reviews)
"I loved the stay here. A great quiet place with an awesome restaurant and unbelievable staff. "
United States
Louie
The price is NZ$416
includes taxes & fees
17 Sept - 18 Sept
Borgo Il Poggiaccio

6. Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (476 reviews)
"Fantastic location and very friendly staff, we will definitely be back"
United Kingdom
Luis
The price is NZ$218
includes taxes & fees
30 Aug - 31 Aug
Siena Vip

7. CANONICA 43 Luxury villa in the heart of Tuscany

CANONICA 43 Luxury villa in the heart of Tuscany
colle di val d'elsa
10.0 out of 10, Exceptional, (14 reviews)
"We had a very plezant stay!"
Netherlands
Ann R.
The price is NZ$1,198
includes taxes & fees
8 Sept - 9 Sept
CANONICA 43 Luxury villa in the heart of Tuscany

8. Room 'Castagno' – Agriturismo la Taverna di Celsa with Shared Pool

Room 'Castagno' – Agriturismo la Taverna di Celsa with Shared Pool
Sovicille
Room 'Castagno' – Agriturismo la Taverna di Celsa with Shared Pool

9. Antico Borgo il Cardino

Antico Borgo il Cardino
San Gimignano
9.4 out of 10, Exceptional, (85 reviews)
"It was perfect for my one night stop before moving on to another location in Toscana."
United States
Craig
The price is NZ$334
includes taxes & fees
30 Aug - 31 Aug
Antico Borgo il Cardino

10. Fullino Nero

Fullino Nero
Siena
9.6 out of 10, Exceptional, (54 reviews)
"Great stay! Clean rooms with air conditioning. Beautiful grounds "
United States
Christian
The price is NZ$194
includes taxes & fees
30 Aug - 31 Aug
Fullino Nero

11. Casa di Campagna in Toscana

Casa di Campagna in Toscana
Sovicille
9.6 out of 10, Exceptional, (27 reviews)
"A wonderful stay. "
United States
Sally
The price is NZ$236
includes taxes & fees
2 Sept - 3 Sept
Casa di Campagna in Toscana

12. Ca' Bianca Tuscany Relais

Ca' Bianca Tuscany Relais
Siena
10.0 out of 10, Exceptional, (46 reviews)
"Clean room, amazing staff"
Canada
Talha
The price is NZ$565
includes taxes & fees
30 Aug - 31 Aug
Ca' Bianca Tuscany Relais

13. Riserva di Fizzano Residence

Riserva di Fizzano Residence
3.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (36 reviews)
"Great place to stay in Tuscany! Very nice breakfast also!"
United States
Janet
The price is NZ$365
includes taxes & fees
8 Sept - 9 Sept
Riserva di Fizzano Residence

14. Residenza d'Epoca Palazzo Borghesi

Residenza d'Epoca Palazzo Borghesi
Siena City Centre
9.6 out of 10, Exceptional, (130 reviews)
"The room was very impressive with a large Chandelier. The breakfast was Delicious and the staff very very nice and helpful"
United States
Peggy
The price is NZ$399
includes taxes & fees
6 Sept - 7 Sept
Residenza d'Epoca Palazzo Borghesi

15. Residence Arianna

Residence Arianna
Sovicille
9.8 out of 10, Exceptional, (7 reviews)
"We had a 4 night’s stay here and used it as our base for tours around Toscany. It is located in a quiet area outside Siena. The apartment was nice and clean. We used the kitchen for minor cooking and that worked well. There is a supermarket close by and small restaurants in the town. The AC was working great. The host was very keen to share information on good places to see and was eager to make our stay as pleasant as possible. The breakfast was very nice and they also have a restaurant where...
Denmark
Gitte Harrits
The price is NZ$254
includes taxes & fees
17 Sept - 18 Sept
Residence Arianna

16. Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.2 out of 10, Wonderful, (29 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is NZ$164
includes taxes & fees
31 Aug - 1 Sept
Tuscasì Aparthotel

17. Tuscan Private Estate with Pool - 5 Charming Villas at Tenuta Cantona,

Tuscan Private Estate with Pool - 5 Charming Villas at Tenuta Cantona,
Toscana
The price is NZ$756
includes taxes & fees
30 Aug - 31 Aug
Tuscan Private Estate with Pool - 5 Charming Villas at Tenuta Cantona,

18. Guild Living Siena Senior Resort & Residence

Guild Living Siena Senior Resort & Residence
Scacciapensieri
8.8 out of 10, Excellent, (49 reviews)
"New facilities, its great, nice, friendly"
United Kingdom
tomaz
The price is NZ$280
includes taxes & fees
28 Sept - 29 Sept
Guild Living Siena Senior Resort & Residence

19. Il Pozzo di Sant'Andrea

Il Pozzo di Sant'Andrea
Siena
9.8 out of 10, Exceptional, (16 reviews)
"Great host, lovely place near Siena"
United Kingdom
Prem
The price is NZ$216
includes taxes & fees
3 Sept - 4 Sept
Il Pozzo di Sant'Andrea

20. Residence Borgo San Lorenzo a Linari

Residence Borgo San Lorenzo a Linari
Sovicille
8.6 out of 10, Excellent, (99 reviews)
"Such a pleasant stay and the staff was incredible. "
United States
Monica
The price is NZ$240
includes taxes & fees
13 Sept - 14 Sept
Residence Borgo San Lorenzo a Linari
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top San Chimento Hotel Reviews

Find out more about San Chimento

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our San Chimento holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up San Chimento. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in San Chimento. Seeing all the best attractions is bound to make you fall in love with San Chimento. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in San Chimento short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in San Chimento?

Yes, there are holiday rentals close to the most popular sights in San Chimento, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that San Chimento has to offer?

Borgo Argiano: This holiday home rental outside of San Chimento is located on a river, and has a balcony, a terrace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and an espresso maker. You can relax into your holiday with a garden and a library.

What’s there to see and do in San Chimento?

Explore the area and family-friendly sights such as Chianti Observatory, or get out into nature at a spot like Alta Val d'Elsa River Park. Monteriggioni Castle and Museo del Cristallo di Colle di Val d'Elsa are a couple of places you'll find in the wider area.

What’s a holiday rental in San Chimento like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in San Chimento. Holiday rentals feature amenities such as hot tubs, fire pits and patios so you'll be comfy for your stay. If you're concerned about a clean environment, a holiday rental can provide a sense of seclusion away from public hotel lifts and busy front desks while still allowing you to travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular option for a family trip.