Pentolina Holiday Rentals

  • 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
5 Jun - 7 Jun
In two months
17 Jul - 19 Jul
In three months
14 Aug - 16 Aug
In four months
11 Sept - 13 Sept

Our top choices for Pentolina holiday rentals

Exterior

B&B Le Scalette di Piazza

B&B Le Scalette di Piazza
Montalcino
9.4 out of 10, Exceptional, (93 reviews)
"Great location, nice room, and great host!"
United States
Chris
The price is S$211
includes taxes & fees
24 May - 25 May
B&B Le Scalette di Piazza
Exterior

Idolina Guest House

Idolina Guest House
Montalcino
9.4 out of 10, Exceptional, (113 reviews)
"Excellent service, ideal location"
United Kingdom
Nigel
The price is S$180
includes taxes & fees
8 Jun - 9 Jun
Idolina Guest House
Exterior

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 S$115
includes taxes & fees
14 Jun - 15 Jun
Country House il Ciliegio
Aerial view

Bosco della Spina

Bosco della Spina
Murlo
9.6 out of 10, Exceptional, (171 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 S$179
includes taxes & fees
24 May - 25 May
Bosco della Spina
Terrace/patio

Casa di Campagna in Toscana

Casa di Campagna in Toscana
Sovicille
9.4 out of 10, Exceptional, (23 reviews)
"Beautiful property in the middle of nature with an excellent restaurant and super friendly staff."
United States
Matt
The price is S$185
includes taxes & fees
29 May - 30 May
Casa di Campagna in Toscana
Premium bedding, down duvets, pillow-top beds, minibar

Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.0 out of 10, Wonderful, (26 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is S$122
includes taxes & fees
3 Jun - 4 Jun
Tuscasì Aparthotel
Exterior

Villa Montecastello

Villa Montecastello
Monteriggioni
The price is S$269
includes taxes & fees
3 Jun - 4 Jun
Villa Montecastello
Food court

Borgo Il Poggiaccio

Borgo Il Poggiaccio
Sovicille
8.8 out of 10, Excellent, (65 reviews)
"Beautiful place, great position in the countryside, truly relaxing place, wish we could stay longer, definitely will return A***"
United States
Dean
The price is S$228
includes taxes & fees
4 Jun - 5 Jun
Borgo Il Poggiaccio
Exterior

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 S$145
includes taxes & fees
25 May - 26 May
Il Pozzo di Sant'Andrea
Room amenity

Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (445 reviews)
"It’s very close to the historical center but feels quiet and like you are separate from it. I loved our stay"
United States
David
The price is S$209
includes taxes & fees
4 Jun - 5 Jun
Siena Vip
Property grounds

Domus il Palio B&B

Domus il Palio B&B
Ravacciano
9.2 out of 10, Wonderful, (88 reviews)
"Hotel clean comfortable. No elevator, no reception desk. "
United States
Karin
The price is S$120
includes taxes & fees
14 Jun - 15 Jun
Domus il Palio B&B
Aerial view

Riserva di Fizzano Residence

Riserva di Fizzano Residence
3.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (30 reviews)
"The view was so incredible and the pool just like a dream. "
Canada
Sarah
The price is S$317
includes taxes & fees
27 May - 28 May
Riserva di Fizzano Residence
Food court

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 S$252
includes taxes & fees
27 May - 28 May
Antico Borgo Poggiarello
Aerial view

Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (65 reviews)
"Pros: 1. Beautiful property with an amazing view. 2. Spacious family suite 3. Comfortable bed 4. Quiet, waking up to birds singing in the morning. Cons: 1. Stink bugs in the suite; once we understood they are common this time of year and easy to capture and release outside, it was ok. 2. Showers are very small. 3. A/C not turned on this time of year; was not offered fans until the last day. 4. Minimal amenities. 5. Few outlets The villa is beautiful, just be prepared for a “rustic”...
United States
Niyo
The price is S$219
includes taxes & fees
25 May - 26 May
Villa Curina Resort
Premium bedding, Select Comfort beds, minibar, in-room safe

La Terrazza Sul Campo Rooming House

La Terrazza Sul Campo Rooming House
Siena City Centre
9.8 out of 10, Exceptional, (242 reviews)
"My first time in Siena and this Rooming House turned out to be a great choice. The view onto the piazza is a real bonus, as is the great location in the heart of the city. The host was lovely and a great communicator. The room itself was fantastic and spacious. I would recommend it and will book again. "
United Kingdom
Jeffrey William
The price is S$168
includes taxes & fees
11 Jun - 12 Jun
La Terrazza Sul Campo Rooming House
Front of property

Residence Borgo San Lorenzo a Linari

Residence Borgo San Lorenzo a Linari
Sovicille
8.6 out of 10, Excellent, (98 reviews)
"Such a pleasant stay and the staff was incredible. "
United States
Monica
The price is S$237
includes taxes & fees
4 Jun - 5 Jun
Residence Borgo San Lorenzo a Linari
Interior detail

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 S$231
includes taxes & fees
9 Jun - 10 Jun
La Coroncina Lodging
Exterior

Antico Borgo il Cardino

Antico Borgo il Cardino
San Gimignano
9.4 out of 10, Exceptional, (82 reviews)
"It was perfect for my one night stop before moving on to another location in Toscana."
United States
Craig
The price is S$207
includes taxes & fees
11 Jun - 12 Jun
Antico Borgo il Cardino
Breakfast meal

B&B Il Corso

B&B Il Corso
Siena City Centre
9.8 out of 10, Exceptional, (203 reviews)
"Excellent location, rooms, staff."
United States
Mario Humberto
The price is S$173
includes taxes & fees
24 May - 25 May
B&B Il Corso
Reception

Sportland

Sportland
Colle di Val d'Elsa
7.2 out of 10, Good, (5 reviews)
"Struttura essenziale ed economica "
Italy
Giorgio
The price is S$75
includes taxes & fees
14 Jun - 15 Jun
Sportland
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

Hotel Athena

Hotel Athena

6/10 Okay
"Good location. Bathroom was strange. Toilet behind door. Tricky at night. The shower leaks out of the shower wall, there was a weird smell in bathroom whole time. Room was clean and comfortable. Breakfast was good. "
Sue 2-night trip
Posted 14 hours ago
Hotel Athena

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 an electric kettle. 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 I Canaloni del Torrente Farma. In the wider area, you’ll find Abbazia di San Galgano and Pinacoteca Nazionale.

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.