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Pentolina Holiday Rentals

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Our top choices for Pentolina holiday rentals

1. Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.2 out of 10, Wonderful, (31 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is NZ$148
includes taxes & fees
2 Nov - 3 Nov
Tuscasì Aparthotel

2. 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$222
includes taxes & fees
6 Oct - 7 Oct
Borgo Il Poggiaccio

3. 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$199
includes taxes & fees
30 Oct - 31 Oct
Casa di Campagna in Toscana

4. Residence Arianna

Residence Arianna
Sovicille
9.6 out of 10, Exceptional, (9 reviews)
"The place is excellent! The owner and her daughter extremely friendly and kind! They helped us with everything we needed. I will definitely stay here again. I highly recommend this place!"
United States
Violeta
The price is NZ$280
includes taxes & fees
10 Oct - 11 Oct
Residence Arianna

5. Le Mascie Country House

Le Mascie Country House
Casole d'Elsa
9.2 out of 10, Wonderful, (9 reviews)
"We loved our stay. The property is quiet and private but is in close proximity to a small town. Very charming and the pool was an added bonus. "
United States
Misti
The price is NZ$385
includes taxes & fees
7 Oct - 8 Oct
Le Mascie Country House

6. Bosco della Spina

Bosco della Spina
Murlo
9.6 out of 10, Exceptional, (179 reviews)
"Lovely stay! I would highly recommend this hotel. The indoor pool was just so enjoyable after a day out sightseeing. "
United Kingdom
Lizl
The price is NZ$174
includes taxes & fees
27 Oct - 28 Oct
Bosco della Spina

7. La Coroncina Lodging

La Coroncina Lodging
Siena
10.0 out of 10, Exceptional, (43 reviews)
"Fantastic place, and I highly recommend it."
United States
Hassan
The price is NZ$274
includes taxes & fees
26 Oct - 27 Oct
La Coroncina Lodging

8. Prestigious apartment infinity pool breathtaking view wifi and air conditioning

Prestigious apartment infinity pool breathtaking view wifi and air conditioning
San Rocco A Pilli
10.0 out of 10, Exceptional, (57 reviews)
"The house was delightful, with lovely views, comfortable beds, a great kitchen and a pool that it was a bit too chilly to use but was lovely to look at."
United States
Kathy B.
The price is NZ$1,132
includes taxes & fees
6 Oct - 7 Oct
Prestigious apartment infinity pool breathtaking view wifi and air conditioning

9. Fullino Nero

Fullino Nero
Siena
9.6 out of 10, Exceptional, (56 reviews)
"Great stay! Clean rooms with air conditioning. Beautiful grounds "
United States
Christian
The price is NZ$217
includes taxes & fees
7 Oct - 8 Oct
Fullino Nero

10. ApartHotel Anghel

ApartHotel Anghel
Siena
8.4 out of 10, Very good, (349 reviews)
"Humming noise in the room. Slow internet. Fine bed. Good location."
Netherlands
Lauro
The price is NZ$158
includes taxes & fees
12 Oct - 13 Oct
ApartHotel Anghel

11. Antico Borgo Poggiarello

Antico Borgo Poggiarello
2.0 star property
Monteriggioni
9.0 out of 10, Wonderful, (20 reviews)
"We had an absolutely wonderful time staying here. Our kids had fun on their playground and my wife and I enjoyed the views, the hospitality. And the entire experience. The food was outstanding. "
United States
James Bakley
The price is NZ$320
includes taxes & fees
14 Oct - 15 Oct
Antico Borgo Poggiarello

12. Exclusive Stone Tower.

Exclusive Stone Tower.
Casciano
9.6 out of 10, Exceptional, (10 reviews)
"Loved it!"
United States
Ryan C.
The price is NZ$281
includes taxes & fees
6 Oct - 7 Oct
Exclusive Stone Tower.

13. Guild Living Siena Senior Resort & Residence

Guild Living Siena Senior Resort & Residence
Scacciapensieri
8.8 out of 10, Excellent, (52 reviews)
"Amazing! Thank you!"
United Kingdom
Lucy
The price is NZ$237
includes taxes & fees
1 Nov - 2 Nov
Guild Living Siena Senior Resort & Residence

14. House with pool for 4 pax

House with pool for 4 pax
Pievescola
9.4 out of 10, Exceptional, (3 reviews)
"Besser kann man es nicht haben. Den Pool hatten wir gefühlt immer für uns alleine. Die Lage der Unterkunft erlaubt es uns schnell in Siena und San Gimignano zu sein, auch die anderen Sehenswürdigkeiten in der Region waren schnell zu erreichen. In der Unterkunft war es sehr ruhig, ideal um sich zu erholen. Traumhaft schön. Wir kommen gerne wieder. Ciao Oli"
Germany
Oliver E.
The price is NZ$542
includes taxes & fees
6 Oct - 7 Oct
House with pool for 4 pax

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

La Senesina, Monteriggioni, Siena. In the best countryside of Tuscany !
Siena
10.0 out of 10, Exceptional, (66 reviews)
"Super helpful host"
Australia
Robyn D.
La Senesina, Monteriggioni, Siena. In the best countryside of Tuscany !

16. Belvedere Nada

Belvedere Nada
San Rocco A Pilli
The price is NZ$345
includes taxes & fees
5 Nov - 6 Nov
Belvedere Nada

17. Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (485 reviews)
"Fantastic location and very friendly staff, we will definitely be back"
United Kingdom
Luis
The price is NZ$191
includes taxes & fees
2 Nov - 3 Nov
Siena Vip

18. 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$335
includes taxes & fees
6 Oct - 7 Oct
Villa Montecastello

19. Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.8 out of 10, Exceptional, (102 reviews)
"We love this beautiful exquisitely appointed hotel in a town with unexpected treasures and great food "
United Kingdom
John
The price is NZ$298
includes taxes & fees
6 Oct - 7 Oct
Palazzo Pacini

20. Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (80 reviews)
"Beautiful resort in the hills, lovely and charming room, incredibly spacious."
United States
Deanna
The price is NZ$233
includes taxes & fees
12 Oct - 13 Oct
Villa Curina Resort
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 Pentolina Hotel Reviews

Find out more about Pentolina

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 Pentolina 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 Pentolina. 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 Pentolina. Seeing all the best attractions is bound to make you fall in love with Pentolina. 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 Pentolina short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find holiday rentals in Pentolina?

Yes, there are holiday rentals close to the most popular sights in Pentolina, 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 Pentolina has to offer?

Borgo Argiano: This holiday home rental outside of Pentolina 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 kitchenware. You can relax into your holiday with a garden and a library.

What can I see and do in Pentolina?

Explore the area and family-friendly sights such as Terme Petriolo, or get out into nature at a spot like Val di Merse. In the wider area, you’ll find Abbazia di San Galgano and I Canaloni del Torrente Farma.

What are holiday rentals like in Pentolina?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Pentolina. Holiday rentals feature amenities such as WiFi and washers and dryers 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 lobbies while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a great choice for family trips.