Pentolina Holidays from £328

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Your Pentolina Holiday

Come and discover this vibrant city for yourself with a Pentolina holiday package. Consider spending some time in the neighbourhood of Frosini, which is great for history and culture, and your time here is bound to be unforgettable. Abbazia di San Galgano and Eremo di Montesiepi are a couple of the major attractions to visit during your trip to Pentolina. Whatever your travel plans or budget, organising your ultimate tailored Pentolina holiday is a breeze with Expedia.

The Latest Pentolina Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Aurum Firenze

Aurum Firenze

4 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
31 Aug - 4 Sept
found 1 day ago
Return flight included
Birmingham (BHX) to Florence (FLR)
7.8/10 Good! (1,000 reviews)
If one is not there for a fancy hotel room, but for sightseeing, this is a great, clean, bare bones room. It is close to the train station. We were on the 5th floor and had a great view! Breakfast was also on the 5th floor. Close proximity to all the museums and Duomo, 20 minute walk or less to everything. We walked everywhere!

Reviewed on 21 Jun 2025

Hotel Bencista

Hotel Bencista

3 out of 5
per person
16 Aug - 23 Aug
found 11 hours ago
Return direct flight included
Manchester (MAN) to Florence (FLR)
7.2/10 Good! (11 reviews)
Giovanni Rooms Manarola

Giovanni Rooms Manarola

1 out of 5
Save 100% on your flight
per person
20 Aug - 27 Aug
found 17 hours ago
Return direct flight included
Birmingham (BHX) to Pisa (PSA)
8.2/10 Very Good! (85 reviews)
This property is in the centre of Manarola. A lovely, well-looked-after place. If you want to experience waking up in this amazing part of the world, we recommend this location.

Reviewed on 26 Apr 2025

Grand Hotel Cavour

Grand Hotel Cavour

4 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
2 Sept - 6 Sept
found 1 day ago
Return direct flight included
Birmingham (BHX) to Florence (FLR)
9.2/10 Wonderful! (1,003 reviews)
Fantastic people and best view in Florence at night. Breakfast the best in Florence. Would go back in a heart beat

Reviewed on 25 Jun 2025

Tenuta di Artimino Member of Meliá Collection

Tenuta di Artimino Member of Meliá Collection

4 out of 5
Save 100% on your flight
per person
8 Sept - 15 Sept
found 1 day ago
Return flight included
London (LON) to Florence (FLR)
9.4/10 Exceptional! (115 reviews)
One of the most amazing hotels I’ve ever stayed.

Reviewed on 23 Jun 2025

Hotel Miramare

Hotel Miramare

4 out of 5
Save 100% on your flight
per person
6 Sept - 13 Sept
found 1 day ago
Return flight included
London (LON) to Pisa (PSA)
8.4/10 Very Good! (441 reviews)
Beautiful views with wonderful people at the helm. Truly an enjoyable time.

Reviewed on 22 Jun 2025

Pentolina Essential Information

Language
Italian
Currency
Euros
Local Welcome
Ciao
Local Goodbye
Ciao
Max Temp Winter
10ºC
Max Temp Summer
29ºC
Top Sights
Abbazia di San Galgano and Eremo di Montesiepi

Our pick of the best Pentolina Hotel Deals

Hotel Athena
Hotel Athena
4 out of 5
P Mascagni 55, Siena, SI
Stay at this 4-star business-friendly hotel in Siena. Enjoy free Wi-Fi, free parking and a rooftop terrace. Our guests praise the breakfast and the helpful staff ...
9.2/10 Wonderful! (1,001 reviews)
"From the moment we arrived for our two night stay Matteo and Tomasso were kind helpful and informative - We wanted a bigger room and were immediately accommodated - room was clean and comfortable and the hotel was in walking distance to all activities"

Reviewed on 21 Jun 2025

Hotel Athena
Hotel Executive
Hotel Executive
4 out of 5
Via Nazareno Orlandi 32, Siena, SI
Stay at this 4-star family-friendly hotel in Siena. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the helpful staff in their reviews. ...
8.2/10 Very Good! (480 reviews)
"Really comfortable hotel , only stayed one night . A great nights sleep . All the staff without exception were friendly, helpful and could not do enough for us. Breakfast selection was in abundance but unfortunately the quality of the food was not great . Maybe less selection with better quality ..."

Reviewed on 2 Oct 2024

Hotel Executive
Hotel Italia
Hotel Italia
3 out of 5
Viale Camillo Benso Conte di Cavour, 67, Siena, SI
Stay at this 3-star business-friendly hotel in Siena. Enjoy free breakfast, free Wi-Fi and room service. Our guests praise the breakfast and the helpful staff ...
9/10 Wonderful! (988 reviews)
"Camas, area y staff muy buenos."

Reviewed on 22 Jun 2025

Hotel Italia
See all 3,464 properties in Pentolina
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.

All Inclusive Holidays

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

Frequently asked questions

Why should I book my Pentolina holiday with Expedia?
With great-value flights, car hire and hotel options all in one place, Expedia makes booking your Pentolina getaway a cinch. What's more, we can help you bundle your bookings into a package holiday so you can save even more. Choose from amazing escapes, add flights and/or a hire car (and maybe even some fun tours!) and get unbeatable prices. Want to change your plans? Expedia offers a flexible cancellation policy for many bookings. To find out more, visit our Customer Service Portal link.
When is the best time of year to holiday in Pentolina?
Pentolina gets busy in January, March and September. If you're not into crowds and prefer a calmer pace, lock in your getaway for February, April and July. Arrange your trip to Pentolina according to what style of adventure you want. January is the coolest month, when average daytime temperatures are 4ºC. In July, the warmest month, you will experience temperatures of around 24ºC during the day.
What is the top hotel for my holiday in Pentolina?
Borgo Santo Pietro sets the stage for a wonderful adventure in Pentolina, offering all the amenities you'll need and more.
How do I get a cheap holiday to Pentolina?
Secure flights that suit your busy schedule, add a hotel room to your booking and watch the savings stack up with a Pentolina holiday. It's that easy! From hotels and flights to hire cars and tours, Expedia is your gateway to cheap travel. And with over 400 partner airlines and 321,000 hotels across the globe to select from, you'll never be short of choice. Learn more about how you can save money on your next holiday when you combine your hotel and flight bookings with Expedia.
What should I do on my Pentolina holiday?
When arranging a holiday in Pentolina, be sure to put Abbazia di San Galgano on your list of must-sees. To make your time away even more special, include Eremo di Montesiepi and other notable tourist attractions here too.
Do I need a visa for my Pentolina holiday?
Official government websites are the best source of information on visa requirements, application procedures and any supporting documentation. Your nationality and reason for visiting, whether it be for work or pleasure, will determine if you'll need a visa for Pentolina. Also double-check that your passport is up to date and has at least six months validity remaining beyond your date of return. Finalise all your travel planning ahead of time to avoid any nasty last-minute surprises.
What should I wear on my Pentolina holiday?
Although everyone's personal style differs, it can be useful to have a few guidelines for what type of clothes to wear on your holiday in Pentolina. Consider searching style blogs before you leave for inspiration on fashion trends or dress codes. Check the local weather forecast so you can pack your bags accordingly. The warmest time of year in Pentolina is July, with average daytime temperatures of 24ºC. If you're visiting during the coolest month of January, the mercury hovers around 4ºC during the day.
What does an Expedia Pentolina holiday include?
Hotels, flights and a shiny set of wheels for all your fun road trip adventures. Simply select your favourite bundle and get access to great discounts. Once you've made your booking, add on a few activities and tours and watch your savings grow. When it comes to crafting your Pentolina break, you're the boss! Experience the freedom and flexibility to personalise your holiday your way with Expedia.
Does Expedia offer Book Now, Pay Later Pentolina holidays?
We do. Expedia has partnered with online lender Klarna to help you conveniently pay for your trip in instalments. Simply select the payment plan that works for you during the checkout process and take the stress out of budgeting for your next trip. Remember to bundle your flights, car hire and accommodation with Expedia to get the biggest bang for your buck. Consider these flexible payment options below:

  • Pay monthly holidays: If paying in multiple transactions sounds right for you, Klarna can help. Paying in several transactions will make your holiday dreams come true.
  • No-deposit holidays: If not paying ahead of time for your trip makes clicking that "book now" button easier, choose a no-deposit holiday plan from Klarna so that you can Book Now, Pay Later!

Can I choose my airline with a Pentolina Expedia holiday?
Expedia offers access to more than 400 partner airlines worldwide, so you certainly can. Simply select your preferred air carrier and craft the perfect Pentolina holiday.

Discover the most popular places to visit in Pentolina

Abbazia di San Galgano

4.5/5(3 reviews)

You can learn about the history of Chiusdino when you stop by Abbazia di San Galgano. Discover the area's countryside and spas.

Abbazia di San Galgano

Unmissable things to do in Pentolina

From Florence: Siena & San Gimignano Day Trip with Lunch & Wine Tasting

From Florence: Siena & San Gimignano Day Trip with Lunch & Wine Tasting

£71
per adult
90% of travellers recommend
From Florence: Siena & San Gimignano Day Trip with Lunch & Wine Tasting
From Siena: Chianti and Castles Tour with Wine Tastings

From Siena: Chianti and Castles Tour with Wine Tastings

£72
per adult
From Siena: Chianti and Castles Tour with Wine Tastings
Siena, San Gimignano, Monteriggioni & Chianti from Florence

Siena, San Gimignano, Monteriggioni & Chianti from Florence

£47
per adult
88% of travellers recommend
Siena, San Gimignano, Monteriggioni & Chianti from Florence
See all activities in Pentolina

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.