Montescudaio Vacations from $1,214

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Your Montescudaio Vacation

With plenty of highlights as well as some hidden gems, this city is best experienced with a Montescudaio vacation package. Book a hotel in Marina di Bibbona, which is great for watersports, dining and nature. You'll want to take in some sights during your trip to Montescudaio. Swing by popular attractions like Pista Del Mare Srl, Parco Gallorose and Archaeological Park of Villa Romana of San Vincenzino. No matter your travel plans or budget, putting together a tailored Montescudaio vacation is a piece of cake with Expedia.

The Latest Montescudaio vacation packages

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

Aurum Firenze

4 out of 5
Historic Centre of Florence
Price was $1,939, price is now $1,214 per person
$1,214
per person
Sep 2 - Sep 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Florence (FLR)
7.4/10 Good! (1,039 reviews)
This was a great place to stay, especially if your planning, like we did, to take trips on the Train to other cities during the day!(for us, we went to Pisa one day & Venice another day) Staff was friendly, and breakfast was amazing with the rooftop views. Definitely would suggests this hotel, if your looking for easy access to the train system, and a nice walking distance to local attractions.

Reviewed on Jun 24, 2026

Donati Luxury Tower Suites

Donati Luxury Tower Suites

5 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $2,396, price is now $1,588 per person
$1,588
per person
Aug 26 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.8/10 Exceptional! (68 reviews)
Agradable estancia. Excelente servicio. La habitación la mantenían siempre limpia. Todo queda cerca del área. Muy recomendable

Reviewed on May 23, 2026

Hotel La Scaletta Al Ponte Vecchio

Hotel La Scaletta Al Ponte Vecchio

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $2,981, price is now $2,025 per person
$2,025
per person
Sep 2 - Sep 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Florence (FLR)
8.8/10 Excellent! (1,000 reviews)
We had a wonderful stay at this hotel in Florence. From the moment we arrived, the staff was kind, welcoming, and very helpful. The communication before and during our stay was excellent, which made everything feel smooth and easy. The location was perfect for enjoying Florence, and the hotel itself felt comfortable, clean, and well cared for. After long days walking through the city, it was a great place to come back to and relax. What stood out most was the hospitality. The staff made us feel taken care of without it ever feeling forced. You can tell they genuinely care about their guests having a great experience. We would absolutely stay here again and highly recommend it to anyone visiting Florence.

Reviewed on Jun 16, 2026

Relais Uffizi, Tailor made Hotel

Relais Uffizi, Tailor made Hotel

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $3,333, price is now $2,280 per person
$2,280
per person
Sep 2 - Sep 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Florence (FLR)
9.4/10 Exceptional! (145 reviews)
Great location for our purposes and centrally located. Breakfast was good and the room was quiet.

Reviewed on Jun 17, 2026

Residenza Florentia

Residenza Florentia

1 out of 5
Historic Centre of Florence
Price was $1,966, price is now $1,376 per person
$1,376
per person
Sep 6 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Florence (FLR)
8.4/10 Very Good! (53 reviews)
Staff was helpful, the property was not very well maintained.

Reviewed on Jun 1, 2026

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Montescudaio Hotel Deals

Hu Montescudaio Village

Hu Montescudaio Village

3 out of 5
Via Del Poggetto Montescudaio Montescudaio PI
9.6/10 Exceptional! (25 reviews)
"Super, family of 4. Everything easily available for our stay even things we didn’t know we needed, like an air compressor to blow up pool toys"

Reviewed on Jul 21, 2025

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Hu Montescudaio Village
Max Hotel Livorno

Max Hotel Livorno

4 out of 5
Via Giotto Ciardi, 28 Livorno LI
Fully refundableReserve now, pay when you stay
$80 nightly
The price is $97 total per night from Jun 28 to Jun 29
$97 total
Jun 28 - Jun 29
Total with taxes and fees
8.6/10 Excellent! (1,000 reviews)
"The restaurant food was really excellent, and server was very nice and proficient in English so was able to have good conversation about italy"

Reviewed on May 27, 2026

Max Hotel Livorno
Castelfalfi

Castelfalfi

5 out of 5
Loc. Castelfalfi Montaione FI
$879 nightly
The price is $979 total per night from Jul 7 to Jul 8
$979 total
Jul 7 - Jul 8
Total with taxes and fees
9.6/10 Exceptional! (171 reviews)
"The property has so much to offer. The amenities and the grounds are impeccable. The 2 restaurants are well managed and the food was excellent. Compliments the 2 sommeliers like Maurizio. The highlight of our stay was the spa and pool at the spa. The landscape is beautiful. Overall, my wife and I ..."

Reviewed on Jun 23, 2026

Castelfalfi
See all 4,831 properties in Montescudaio
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 Montescudaio Vacation Packages

Montescudaio Essential Information

Language
Italian
Currency
Euros
Local Welcome
Ciao
Local Goodbye
Ciao
Closest Airport
Galileo Galilei Airport (PSA)
Population
840
Max Temp Winter
55ºF
Max Temp Summer
80ºF
Top Sights
Teatro del Silenzio, La Regola Azienda Vitivinicola and Parco Avventura Il Giardino Sospeso

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Frequently asked questions

How much does a Montescudaio vacation package cost?
You can snap up a vacation package to this destination from $1,214 on Expedia. However, how much your vacation to Montescudaio costs will depend on factors like the length of stay, hotel choice and season.
What are the cheapest months to go to Montescudaio?
If you'd like to book a cheap Montescudaio vacation package, consider planning a trip in November, December and January. You'll generally find better prices on flights and hotels during these months — perfect for travelers wishing to save money.
How many days is enough for Montescudaio?
Typically, a handful of days is enough to tick off the major sights during your Montescudaio vacation. But if you'd like to have time to chill out or go on day trips, think about extending your trip.
How to find the best Montescudaio package deals?
Use Expedia's filter tool to find some of the best Montescudaio 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 adventure for midweek, or browse for Montescudaio package deals in the off-season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to book your vacation package as early as possible.
Is it cheaper to book a Montescudaio vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your hotel, flight and car rental into one great-value price and you could save hundreds of dollars. You'll generally get a better deal than booking each component individually. And you'll still enjoy the freedom to create a personalized Montescudaio vacation by choosing your favorite type of stay, airline and car class.
When to book a vacation package to Montescudaio?
Secure incredible discounts by booking your flights early with Expedia. If spontaneity is more your thing, take advantage of our last-minute deals for a spur-of-the-moment Montescudaio trip.
Does Expedia offer Book Now, Pay Later Montescudaio vacation packages?
If you're like us, you love jet-setting around the world but don't love the price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the cost of your Montescudaio vacation over 3, 6 or 12 months. There are also no hidden or late payment fees, so you can snap up great vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.