Pentolina Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
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Your Pentolina Vacation
Come and discover this vibrant city for yourself with a Pentolina vacation package. Consider spending some time in the neighborhood 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, organizing your ultimate tailored Pentolina vacation is a breeze with Expedia.
Top Pentolina Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Hotel La Scaletta Al Ponte Vecchio
Historic Centre of Florence
CA $1,414
per person
Nov 19 - Nov 25
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Florence (FLR)
9/10 Wonderful! (1,002 reviews)
Great location! Staff was friendly and helpful. Had a wonderful stay Highly recommend!
Reviewed on Oct 11, 2026
Hotel Certosa Di Maggiano
CA $1,774
per person
Dec 5 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Florence (FLR)
10/10 Exceptional! (217 reviews)
Our stay for our honeymoon was amazing. We loved our room and we were upgraded to a suite because they had it available. All the staff were kind and helpful. They carried our luggage up two flights of stairs to our room, helped make reservations, called taxis for us, etc.
The property was beautiful, maintained nicely, and was very quiet.
Really have no complaints. To note it is outside of city Centre of Siena so you will need taxis back and forth to the city for meals etc. which can get quite pricey so just plan ahead. Our room could’ve been cleaned a little better in between each day but overall it was still very clean. We would definitely stay there again!!
Reviewed on Sep 28, 2026
Ready to book your vacation to Pentolina?
Pentolina Hotel Deals
Hotel Athena
P Mascagni 55 Siena SI
Fully refundableReserve now, pay when you stay
CA $181
CA $204 total
Nov 9 - Nov 10
includes taxes & fees
9.2/10 Wonderful! (1,002 reviews)
"Reception staff very friendly and helpful. Room on top floor had two full length windows with spectacular views. Older property but updated nicely; not modern but comfortable. Comfy bed, linens and pillows. Nice breakfast with lots of variety. There are two floors that have breakfast - the lowest ..."
Reviewed on Oct 11, 2026
Grand Hotel Continental Siena – Starhotels Collezione
Banchi Di Sopra 85 Siena SI
Fully refundableReserve now, pay when you stay
CA $455
CA $511 total
Nov 11 - Nov 12
includes taxes & fees
9.2/10 Wonderful! (636 reviews)
"Beautiful hotel and very helpful staff. Excellent location in the heart of Siena. Disappointed with our hotel room. Not up to our expectations."
Reviewed on Oct 6, 2026
Hotel Chiusarelli
Viale Curtatone 15 Siena SI
Fully refundableReserve now, pay when you stay
CA $156
CA $176 total
Nov 10 - Nov 11
includes taxes & fees
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.
What to do in Pentolina
Siena: Cathedral Complex Pass with Audio Guide (OPA SI PASS)
CA $29
per adult
Florence: San Gimignano, Siena, Monteriggioni, Chianti & Lunch with Wine
CA $127
per adult
88% of travellers recommend
At Your Own Pace: Discovering Siena & Tuscany
CA $5
per adult
Frequently asked questions
How much does a Pentolina vacation package cost?
Offering great value package deals from CA $1,216 on Expedia, you'll be surprised at how little a vacation to Pentolina costs! Our packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Pentolina?
You can usually find lower rates and better availability in January, February and November. Browse our cheap Pentolina vacation packages and you could get some excellent off-season deals.
How many days is enough for Pentolina?
Typically, a handful of days is enough to explore the main attractions during your Pentolina vacation. But if you'd like to have time to rest or take day trips, consider extending your itinerary.
How to find the best Pentolina package deals?
Use Expedia's filter tool to help you find some fabulous Pentolina package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your break for midweek, or look for Pentolina package deals in the off-peak season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to book your vacation package well in advance.
Is it cheaper to book a Pentolina vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your flight, car rental and hotel into one great-value price and enjoy significant savings. You'll generally score a better deal than booking each component individually. And you'll still enjoy the flexibility to create a tailored Pentolina vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Pentolina?
If you're planning a spontaneous Pentolina adventure, check out our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can land awesome deals on your flights and hotels by booking ahead.
How to plan a trip to Pentolina?
- Choose when to get away: Check your calendar and get your bags packed. Your favourite time of year and the activities on offer will also help you decide when to escape to Pentolina.
- Work out your budget: Make sure you have enough money to pay for everything from transportation and meals to experiences and flights. Your accommodations will probably be the biggest expense during your trip to Pentolina.
- Determine how many days away: Start by listing all the sights and activities you'd like to get to in Pentolina. Then, estimate how long you'll need for each, as well as any travel time.
- Bundle your accommodations and airfare: After you've nailed down your travel dates and duration, book the perfect Pentolina vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
