Montescudaio Vacations from $1,149

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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.
Hotel La Scaletta Al Ponte Vecchio

Hotel La Scaletta Al Ponte Vecchio

4 out of 5
Historic Centre of Florence
Price was $1,627, price is now $1,149 per person
$1,149
per person
Aug 25 - Aug 31
found 3 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
8.8/10 Excellent! (1,001 reviews)
Room was great, super clean and roomy. Staff awesome and the rooftop bar with view of the city made the stay all the more memorable!

Reviewed on Jul 4, 2026

Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

5 out of 5
Save 100% on your flight
Price was $5,058, price is now $3,123 per person
$3,123
per person
Sep 5 - Sep 11
found 1 day ago
Roundtrip flight included
New York (NYC) to Florence (FLR)
9.6/10 Exceptional! (147 reviews)
It’s a beautiful property, but be aware that it is secluded and that the restaurant menu is quite limited and after a couple of days, we were happy to go elsewhere. The waiting staff was attentive and nice, front desk not as much (maybe the la guard barrier?)

Reviewed on Jun 19, 2026

Hotel degli Orafi

Hotel degli Orafi

4 out of 5
Historic Centre of Florence
Price was $2,126, price is now $1,452 per person
$1,452
per person
Aug 25 - Aug 31
found 3 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.6/10 Exceptional! (1,002 reviews)
Overall very good experience. Breakfast was good but coffee would have been better.

Reviewed on Jul 1, 2026

L'Andana

L'Andana

5 out of 5
Price was $3,252, price is now $2,337 per person
$2,337
per person
Sep 21 - Sep 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Florence (FLR)
9.4/10 Exceptional! (91 reviews)
Breathtaking views of the Tuscan countryside, as well as incredibly attentive staff.

Reviewed on Jun 9, 2026

The Moon Boutique Hotel & Spa

The Moon Boutique Hotel & Spa

4 out of 5
Historic Centre of Florence
Price was $2,317, price is now $1,693 per person
$1,693
per person
Sep 21 - Sep 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Florence (FLR)
9.6/10 Exceptional! (569 reviews)
Wonderful stay, attentive staff, very clean room. The spa facilities are very high quality and had a lovely massage. Good choices for breakfast. I would certainly recommend staying here, the spa was a particular highlight that is free for guests to use.

Reviewed on Jul 2, 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! (26 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
$95 nightly
The price is $113 total per night from Jul 12 to Jul 13
$113 total
Jul 12 - Jul 13
Total with taxes and fees
8.6/10 Excellent! (1,002 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
$887 nightly
The price is $987 total per night from Jul 7 to Jul 8
$987 total
Jul 7 - Jul 8
Total with taxes and fees
9.6/10 Exceptional! (173 reviews)
"Amazing all around! One of the best places I’ve ever stayed! Can’t wait to visit again"

Reviewed on Jul 2, 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 $1,149 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.