San Casciano in Val di Pesa Vacations from $1,285

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Your San Casciano in Val di Pesa Vacation

Lock in a San Casciano in Val di Pesa vacation package and get ready for a fantastic adventure. Renowned for its rich history and spectacular views, there's plenty to love about this interesting city. Eager to explore? Antinori nel Chianti Classico, Montegufoni Castle and Florence Charterhouse are just a few of the best places to visit during a trip to San Casciano in Val di Pesa. A few quick clicks is all it takes to create your perfect San Casciano in Val di Pesa vacation on Expedia.

The Latest San Casciano in Val di Pesa vacation packages

Price found within the past 48 hours. Click for updated prices.
Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

5 out of 5
Cortona Old Town
Price was $1,711, price is now $1,285 per person
$1,285
per person
Oct 11 - Oct 15
found 8 hours ago
Roundtrip flight included
New York (JFK) to Florence (FLR)
10/10 Exceptional! (295 reviews)
Beautiful oasis in a beautiful town

Reviewed on Jul 25, 2026

Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

5 out of 5
Price was $2,376, price is now $1,752 per person
$1,752
per person
Oct 11 - Oct 15
found 8 hours ago
Roundtrip flight included
New York (JFK) to Florence (FLR)
9.6/10 Exceptional! (154 reviews)
Magical location, pools, staff, property.

Reviewed on Jul 19, 2026

Grand Hotel Cavour

Grand Hotel Cavour

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $2,203, price is now $1,433 per person
$1,433
per person
Oct 17 - Oct 22
found 22 hours ago
Roundtrip non-stop flight included
New York (NYC) to Florence (FLR)
9.2/10 Wonderful! (1,000 reviews)
Great location, helpful staff, don’t miss the rooftop bar at night for a great view of the Duomo

Reviewed on Jul 29, 2026

Eurostars Florence Boutique

Eurostars Florence Boutique

4 out of 5
Historic Centre of Florence
Price was $2,156, price is now $1,536 per person
$1,536
per person
Oct 3 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
8.6/10 Excellent! (494 reviews)
Very good location. Clean hotel. Our ac was broken but they handled us a new room inmediately. The hotel is confortable and size of the rooms are decent. Bigger than average in the area.

Reviewed on Jun 26, 2026

The Moon Boutique Hotel & Spa

The Moon Boutique Hotel & Spa

4 out of 5
Historic Centre of Florence
Price was $1,977, price is now $1,429 per person
$1,429
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.6/10 Exceptional! (577 reviews)
The hotel was very well-maintained with helpful staff. The breakfast was fantastic. The only problem was, it was a far walk to the city centre. Despite the walk , I highly recommend this hotel

Reviewed on Jul 20, 2026

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Stay near popular San Casciano in Val di Pesa attractions

Antinori nel Chianti Classico

9.4/10 (16 reviews)
You can enjoy a tasting or tour at Antinori nel Chianti Classico during your travels to Bargino. Check out the churches and wineries in this walkable area.
See properties

What to do in San Casciano in Val di Pesa

City Sightseeing Florence Hop-on Hop-off

City Sightseeing Florence Hop-on Hop-off Bus Tour

$33
per adult
76% of travellers recommend
City Sightseeing Florence Hop-on Hop-off Bus Tour
The Best of Tuscany in One Day Sightseeing Tour

The Best of Tuscany Tour: Siena, San Gimignano, Pisa and Lunch at a Winery

$78
per adult
98% of travellers recommend
The Best of Tuscany Tour: Siena, San Gimignano, Pisa and Lunch at a Winery
People riding scooters in Tuscany

Florence Vespa Tour: Tuscan Hills, Food and Chianti Wine

$126
per adult
100% of travellers recommend
Florence Vespa Tour: Tuscan Hills, Food and Chianti Wine
See all activities in San Casciano in Val di Pesa

San Casciano in Val di Pesa Hotel Deals

Villa I Barronci Resort & Spa

Villa I Barronci Resort & Spa

4 out of 5
Via Sorripa 10 San Casciano in Val di Pesa FI
Fully refundableReserve now, pay when you stay
$148 nightly
The price is $170 total per night from Jul 31 to Aug 1
$170 total
Jul 31 - Aug 1
Total with taxes and fees
Villa I Barronci Resort & Spa
The Social Hub Florence Lavagnini

The Social Hub Florence Lavagnini

4 out of 5
Viale Spartaco Lavagnini 70 72 Florence FI
Fully refundableReserve now, pay when you stay
$83 nightly
The price is $107 total per night from Aug 12 to Aug 13
$107 total
Aug 12 - Aug 13
Total with taxes and fees
9/10 Wonderful! (1,482 reviews)
"No parking in the facility and no coffee machine in the room"

Reviewed on Jul 29, 2026

The Social Hub Florence Lavagnini
Plus Florence - Hostel

Plus Florence - Hostel

Via Santa Caterina D'Alessandria, 15 Florence FI
Fully refundableReserve now, pay when you stay
$79 nightly
The price is $96 total per night from Aug 7 to Aug 8
$96 total
Aug 7 - Aug 8
Total with taxes and fees
8.6/10 Excellent! (1,008 reviews)
"Todo está muy limpio, tienen una piscina muy bonito con un restaurante que la comida estaba deliciosa y está situado en un lugar estratégico para caminar"

Reviewed on Jul 15, 2026

Plus Florence - Hostel
See all 15,047 properties in San Casciano in Val di Pesa
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.

Find the Best San Casciano in Val di Pesa Vacation Packages

San Casciano in Val di Pesa Essential Information

Language
Italian
Currency
Euros
Local Welcome
Ciao
Local Goodbye
Ciao
Closest Airport
Peretola Airport (FLR)
Population
6,200
Max Temp Winter
50ºF
Max Temp Summer
85ºF
Top Sights
Cathedral of Santa Maria del Fiore, Uffizi Gallery and Pitti Palace

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Frequently asked questions

How much does a San Casciano in Val di Pesa vacation package cost?
You'll find cheap prices from $1,285 on Expedia for your San Casciano in Val di Pesa escape. However, factors like the length of stay, hotel choice and season will influence how much your vacation to San Casciano in Val di Pesa costs.
What are the cheapest months to go to San Casciano in Val di Pesa?
You can generally find reduced prices and better availability in September, November and December. Browse our cheap San Casciano in Val di Pesa vacation packages and you could land some excellent off-season deals.
How many days is enough for San Casciano in Val di Pesa?
With about 3 days, you'll have enough time to visit popular neighborhoods such as Tavarnuzze and Montegufoni during your San Casciano in Val di Pesa vacation. Make sure to also add Monastary of Sorelle Clarisse and Church of San Martino ad Argiano to your must-see list. Searching for more adventures? Consider venturing outside of San Casciano in Val di Pesa on day trips and tours.
Is it worth booking a vacation package to San Casciano in Val di Pesa?
San Casciano in Val di Pesa has all the ingredients you need for a memorable getaway — views, bars and pubs and dining are just the start. Whether you'd like to check out attractions such as Monastary of Sorelle Clarisse and Torre Del Chianti, or venture off the beaten track, you'll find plenty to do on your San Casciano in Val di Pesa vacation.
How to find the best San Casciano in Val di Pesa package deals?
Finding a cheap San Casciano in Val di Pesa package deal is a breeze with Expedia. After you've entered your travel dates and destination under our "Packages" tab, set your budget range, add some filters and see what's available. You can tailor your search by "Property class," "Number of bedrooms," "Traveler experience" and more. Sort the results by "Price: low to high" to discover the most affordable San Casciano in Val di Pesa package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider traveling on a weekday, when prices are generally lower.
Is it cheaper to book a San Casciano in Val di Pesa 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 generally land a better deal than booking each component separately. And you'll still get the freedom to create a customized San Casciano in Val di Pesa vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to San Casciano in Val di Pesa?
If you've got your San Casciano in Val di Pesa travel dates finalized, book early to grab some incredible deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spur-of-the-moment adventures? Our last-minute deals are ideal for impromptu escapes.
How to plan a trip to San Casciano in Val di Pesa?

  1. Pick the ideal time to travel: Your schedule, favorite season and the type of weather you like can all impact your decision on when to travel to San Casciano in Val di Pesa.
  2. Set a budget: Factor in expenses such as food, flights and transportation when calculating how much to put aside for your trip to San Casciano in Val di Pesa. Then, pick a property that matches your budget, whether that's a wallet-friendly stay or a more luxurious retreat.
  3. Use Expedia's trip planning tool to discover San Casciano in Val di Pesa: Research every aspect of your trip to San Casciano in Val di Pesa with this comprehensive planner. Invite your friends and family to collaborate on a group trip, search for stays or things to do and make bookings.
  4. Decide how long to go for: Now that you're more familiar with San Casciano in Val di Pesa, you can work out the perfect length of your break. Put together a rough itinerary and give yourself enough time to cover everything you want to see.
  5. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. All that's left is to find a San Casciano in Val di Pesa vacation package that brings all your bookings together.
  6. Book experiences or activities in advance: Whether it's entrance to a big attraction or a day trip in nature, you won't have to worry about missing out on San Casciano in Val di Pesa's highlights. Find all the incredible things to do in San Casciano in Val di Pesa with our dedicated activity guide.

Does Expedia offer Book Now, Pay Later San Casciano in Val di Pesa vacation packages?
If you're anything like us, you love traveling the world but are not a fan of the big price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the overall cost of your San Casciano in Val di Pesa trip across 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can snap up great vacation packages with payment plans as soon as you see them.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.