Default HTG hotel image

Holiday Rentals in Pentolina

  • 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
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Pentolina holiday rentals

A bedroom with a bed, a bedside table, a TV mounted on the wall, and a sliding glass door leading to a balcony with a view of greenery and hills.

1. Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.2 out of 10, Wonderful, (32 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is €74
includes taxes & fees
4 Nov - 5 Nov
Tuscasì Aparthotel
An interior with stone walls, wooden doors, and a bar area with stools and bottles.

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 €146
includes taxes & fees
20 Oct - 21 Oct
Borgo Il Poggiaccio
A stone courtyard with a bench, potted plants, and a building in the background.

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 €94
includes taxes & fees
15 Nov - 16 Nov
Casa di Campagna in Toscana
Outdoor pool

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 €134
includes taxes & fees
9 Nov - 10 Nov
Residence Arianna
An aerial view of a historic stone building complex with a swimming pool, surrounded by lush greenery and vineyards.

5. Bosco della Spina

Bosco della Spina
Murlo
9.6 out of 10, Exceptional, (185 reviews)
"Very peaceful and scenic. Wish we had stayed longer."
United States
Amir
The price is €95
includes taxes & fees
26 Oct - 27 Oct
Bosco della Spina
A traditional stone building with a courtyard, a staircase, and potted plants.

6. 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 €110
includes taxes & fees
23 Oct - 24 Oct
Il Pozzo di Sant'Andrea
A stone building with a tiled roof, a brick pathway, and a small grassy area.

7. 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 €202
includes taxes & fees
31 Oct - 1 Nov
Le Mascie Country House
A modern lobby with white leather sofas, a glass coffee table, and potted plants.

8. ApartHotel Anghel

ApartHotel Anghel
Siena
8.4 out of 10, Very good, (355 reviews)
"Humming noise in the room. Slow internet. Fine bed. Good location."
Netherlands
Lauro
The price is €61
includes taxes & fees
15 Nov - 16 Nov
ApartHotel Anghel
A rustic stone building with a courtyard.

9. Fullino Nero

Fullino Nero
Siena
9.6 out of 10, Exceptional, (57 reviews)
"Very nice place close to"
Canada
Annie
The price is €103
includes taxes & fees
2 Nov - 3 Nov
Fullino Nero
A bedroom with a bed, bedside table, and a window with a view of greenery.

10. 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 €123
includes taxes & fees
9 Nov - 10 Nov
La Coroncina Lodging
A stone building with two windows, one with green shutters, and a rose bush in the foreground.

11. Exclusive Stone Tower.

Exclusive Stone Tower.
Casciano
9.6 out of 10, Exceptional, (10 reviews)
"Loved it!"
United States
Ryan C.
The price is €144
includes taxes & fees
20 Oct - 21 Oct
Exclusive Stone Tower.
A stone building with an arched entrance, surrounded by gravel, potted plants, and trees.

12. 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 €185
includes taxes & fees
24 Oct - 25 Oct
Villa Montecastello
A cozy room with a wooden ceiling, a television on a stand, a bookshelf, and a window with curtains.

13. Nido con vista

Nido con vista
Radicondoli
The price is €149
includes taxes & fees
14 Nov - 15 Nov
Nido con vista
A stone building with outdoor seating and a view of the countryside.

14. 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 €170
includes taxes & fees
22 Oct - 23 Oct
Antico Borgo Poggiarello
A courtyard with stone steps leading to a small building, surrounded by lush greenery and stone buildings in the background.

15. Country House il Ciliegio

Country House il Ciliegio
Roccastrada
9.2 out of 10, Wonderful, (7 reviews)
"It was a very pleasant stay, a warm welcome. A beautiful location surrounded by nature."
Netherlands
Maaike
The price is €85
includes taxes & fees
23 Oct - 24 Oct
Country House il Ciliegio
An outdoor swimming pool with a wooden pergola, lounge chairs, and a stone wall backdrop.

16. Guild Living Siena Senior Resort & Residence

Guild Living Siena Senior Resort & Residence
Scacciapensieri
8.8 out of 10, Excellent, (59 reviews)
"We booked this last - minute and were really impressed with the whole experience. The property and grounds are beautiful. Staff was so friendly and helpful. The rooms were well appointed and quiet. Beds were too firm for our liking, but it was easy to overlook as the entire stay was really great. Good options in the restaurant too. The block of hotel rooms is in a retirement resort, which I think is a wonderful idea! Very much enjoyed our stay. We had a car and parking was free."
United States
Heidi
The price is €141
includes taxes & fees
1 Nov - 2 Nov
Guild Living Siena Senior Resort & Residence
A bakery display with pastries and a coffee station.

17. B&B Il Corso

B&B Il Corso
Siena City Centre
9.8 out of 10, Exceptional, (215 reviews)
"We enjoyed our stay very much. Staff was very friendly and offered great advise on places to eat. The rooms had great charm to them. We were delighted with our selection of where to stay."
United States
Enrique
The price is €76
includes taxes & fees
2 Nov - 3 Nov
B&B Il Corso
A two-story building with a stone facade and a tiled roof.

18. A Nest with a View - A Romantic Retreat Within the City Walls

A Nest with a View - A Romantic Retreat Within the City Walls
Radicondoli
The price is €143
includes taxes & fees
6 Nov - 7 Nov
A Nest with a View - A Romantic Retreat Within the City Walls
A rustic building with a brick facade, a small arched window, and a door.

19. Cozy Tuscan-style apartment Suitable for families. Pets allowed

Cozy Tuscan-style apartment Suitable for families. Pets allowed
Toscana
10.0 out of 10, Exceptional, (2 reviews)
"This refurbished cottage is a hidden gem, surrounded by fruit trees on a hillside facing Siena. You’ll need a car — it s about a 5-minute drive on a steep, narrow, winding road to get to the stores by the freeway. The cottage was bigger than we were expecting, with a small but well-equipped kitchen. The host turned on the AC in anticipation of our arrival. There are two bedrooms on the main floor with AC, and a fourth bed in a loft."
United States
Shanti R.
The price is €192
includes taxes & fees
19 Nov - 20 Nov
Cozy Tuscan-style apartment Suitable for families. Pets allowed
A gated entrance with a number plaque, a pathway leading to a building, and a parked vehicle.

20. Tuscan House: Spacious, Traditional Tuscan Apartment with Plenty of Outdoor Space and Breakfast Included

Tuscan House: Spacious, Traditional Tuscan Apartment with Plenty of Outdoor Space and Breakfast Included
Monteroni d'Arbia
Tuscan House: Spacious, Traditional Tuscan Apartment with Plenty of Outdoor Space and Breakfast Included
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Pentolina Hotel Reviews

Il Chiostro del Carmine

Il Chiostro del Carmine

10/10 Excellent
"Great location and very helpful staff"
Edward 2-night trip
Posted 4 hours ago
Il Chiostro del Carmine

Find out more about Pentolina

Everything you need to know about Pentolina 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 Pentolina holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, 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 Pentolina holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Pentolina holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Pentolina. 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 Pentolina 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 Pentolina holiday rentals we have selected for you start as low as €55 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Pentolina rentals

At Expedia, we put the best Pentolina 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 Pentolina 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 Pentolina 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 Pentolina. 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

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.