Villa Vacation Packages
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Your Villa Vacation
The easiest way to experience this city is with a customized Villa vacation package. Stay in the neighborhood of Badia Coltibuono, which is good for families, nature and walking or go someplace else — our package deals are all about you. A trip to Villa is a terrific opportunity to go sightseeing. Be sure to stop by popular attractions like Castello di Albola, Castello di Radda Winery and Borgo di Vescine - Tenute di Castelvecchi. Check out Expedia's extensive range of travel options and begin planning your perfect vacation to Villa today.
Top Villa Vacation Deals
Price found within the past 48 hours. Click for updated prices.
La Villa di STR
Siena Historical Center
CA $1,242
per person
Dec 6 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Florence (FLR)
9.2/10 Wonderful! (450 reviews)
We had a great stay at La Villa. We spent 4 days bicycling and our rental company was able to coordinate drop off and pick up without us needing to be involved. They had a storage area for our bikes. Location was away from the crowds but close enough to walk to all of the sites. Breakfast was excellent.
Reviewed on Oct 13, 2026
The Moon Boutique Hotel & Spa
Historic Centre of Florence
CA $3,085
per person
Dec 26 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Florence (FLR)
9.6/10 Exceptional! (605 reviews)
Very clean room with cold ac . Well thought out bathroom . Nice size room for Europe . And for the ladies the lighting in the bathroom was excellent .
Reviewed on Oct 13, 2026
Grand Hotel Cavour
Historic Centre of Florence
CA $2,188
per person
Dec 25 - Dec 30
found 2 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Florence (FLR)
9.4/10 Exceptional! (1,000 reviews)
Staff was friendly and accommodating! Rooms were very clean and SPACIOUS!
Would definitely return!
Reviewed on Oct 5, 2026
Eurostars Florence Boutique
Historic Centre of Florence
CA $2,833
per person
Dec 27 - Jan 2
found 6 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
8.6/10 Excellent! (503 reviews)
The bed was comfortable but low to the floor. The shower was very slippery and could have used a shower mat. The breakfast was great. The staff were very nice and helpful.
Reviewed on Oct 10, 2026
Hotel Certosa Di Maggiano
CA $1,655
per person
Dec 6 - 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 Villa?
Villa Hotel Deals
Radisson Blu Hotel, Florence
Via Giovanni Agnelli 33 Florence FI
CA $152
CA $190 total
Nov 1 - Nov 2
includes taxes & fees
8.8/10 Excellent! (185 reviews)
"Everything was very clean and fresh. Great experience!"
Reviewed on Oct 11, 2026
Hotel Athena
P Mascagni 55 Siena SI
Fully refundableReserve now, pay when you stay
CA $168
CA $189 total
Nov 13 - Nov 14
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 $463
CA $519 total
Nov 13 - Nov 14
includes taxes & fees
9.2/10 Wonderful! (638 reviews)
"Gorgeous hotel in the heart of historic Siena."
Reviewed on Oct 13, 2026
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 Villa
Siena: Cathedral Complex Pass with Audio Guide (OPA SI PASS)
CA $29
per adult
Chianti Half Day Wine Tour from Florence
CA $39
per adult
88% of travellers recommend
Siena, San Gimignano, Monteriggioni & Chianti from Florence
CA $104
per adult
88% of travellers recommend
Frequently asked questions
How much does a Villa vacation package cost?
Offering great value package deals from CA $1,242 on Expedia, you'll be pleasantly surprised at how much a vacation to Villa costs! Our packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Villa?
January, February and November are great times to search for cheap Villa vacation packages. Opting to travel in quieter months means you can usually find reduced prices on hotels and flights.
How many days is enough for Villa?
With a well-organized schedule, you can easily tick off the top Villa sights in a few days. But if you want to discover hidden gems or take day trips, think about booking your Villa vacation for longer.
How to find the best Villa package deals?
Use Expedia's filter tool to find some fabulous Villa package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or look for Villa package deals in the off-season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to book your vacation package well in advance.
Is it cheaper to book a Villa vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your hotel, flight and car rental into one great-value price and you could save hundreds of dollars. You'll usually snag a better deal than booking each component separately. And you'll still get the freedom to create a tailored Villa vacation by choosing your favourite accommodation type, airline and car class.
When to book a vacation package to Villa?
Secure incredible discounts by booking your flights in advance with Expedia. If being spontaneous is more your thing, grab one of our last-minute deals for a spur-of-the-moment Villa break.
How to plan a trip to Villa?
- Choose your dates: The things you want to do in Villa and your preferred season can help you decide when to travel.
- Plan your budget wisely: As well as the cost of your hotel, you'll need to consider other expenses too. These include flights, food and transportation. Also, set aside some extra funds for unexpected expenses that may come up during your trip to Villa.
- Decide how long to go for: Now that you're more familiar with Villa, you can work out the ideal length of your break. Create a rough plan and allocate enough time to cover everything you want to do.
- Combine your flights and hotel: Epic destination, check. Length of stay, check. All that's left is to choose a Villa vacation package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
