Montescudaio Vacations from $562

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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.
Castello di Bossi

Castello di Bossi

2 out of 5
Price was $685, price is now $562 per person
$562
per person
Dec 9 - Dec 13
found 8 hours ago
Roundtrip flight included
Tel Aviv (TLV) to Florence (FLR)
7.8/10 Good! (8 reviews)

The Place Firenze

The Place Firenze

5 out of 5
Historic Centre of Florence
Price was $2,138, price is now $1,616 per person
$1,616
per person
Dec 9 - Dec 13
just found
Roundtrip non-stop flight included
Tel Aviv (TLV) to Florence (FLR)
9.8/10 Exceptional! (203 reviews)

The Hoxton, Florence

The Hoxton, Florence

4 out of 5
Historic Centre of Florence
Price was $1,067, price is now $853 per person
$853
per person
Jan 16 - Jan 20
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
9.4/10 Exceptional! (370 reviews)
Very nice staff, clean rooms and great room service and nice furniture ! Close to the main touristy places in the city, maximum of 30 minutes walk radius from everything that I wanted to visit!

Reviewed on Nov 2, 2026

Donati Luxury Tower Suites

Donati Luxury Tower Suites

5 out of 5
Historic Centre of Florence
Price was $1,476, price is now $1,198 per person
$1,198
per person
Dec 9 - Dec 13
just found
Roundtrip non-stop flight included
Tel Aviv (TLV) to Florence (FLR)
9.8/10 Exceptional! (82 reviews)
Great location. Historical building. Rooms were stunning. Lovely breakfast box delivered daily. Nice staff. The only negative is the roof is €250 per 2 hour booking, which I didn't expect, and would have been a reason for booking. Hence 4/5.

Reviewed on Oct 19, 2026

Hotel Renaissance

Hotel Renaissance

3 out of 5
Historic Centre of Florence
Price was $6,292, price is now $4,649 per person
$4,649
per person
Dec 27 - Jan 1
found 12 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.4/10 Exceptional! (538 reviews)
The hotel was great with helping us arrange the hotel offered walking tour to introduce us to Florence. Sabina the owner/host was our tour guide, and she was excellent during our private tour of Florence, she was very knowledgeable about the city, and it was a perfect introduction and start to our trip. The hotel itself was great, located in an old monastery just minutes away from the Uffizi gallery. The Turkish steam shower was a great option in our chosen room. Everything about our stay was perfect and Both Sabina, her son, and the rest of the staff were extremely helpful and accommodating. Thanks again for a great stay and we hope to see you again soon someday.

Reviewed on Oct 21, 2026

Don't see what you're looking for?
See all available trips from Columbus to Montescudaio
View all trips

Montescudaio Hotel Deals

Hu Montescudaio Village

Hu Montescudaio Village

3 out of 5
Via Del Poggetto Montescudaio Montescudaio PI
9.4/10 Exceptional! (32 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

Get rates
Hu Montescudaio Village
Max Hotel Livorno

Max Hotel Livorno

4 out of 5
Via Giotto Ciardi, 28 Livorno LI
$93 nightly
The price is $107 total per night from Dec 4 to Dec 5
$107 total
Dec 4 - Dec 5
Total with taxes and fees
8.6/10 Excellent! (1,000 reviews)
"The bed was very hard and uncomfortable. There were barely any sheets on the bed so I was cold at night. The door to the bathroom is glass so going to the bathroom at night and turning on the light means your partner can be woken up by the light. Poor design. The room was quite small. The best thing ..."

Reviewed on Oct 15, 2026

Max Hotel Livorno
Tombolo Talasso & Beach Resort

Tombolo Talasso & Beach Resort

5 out of 5
Via Del Corallo 3 Castagneto Carducci LI
Fully refundableReserve now, pay when you stay
$251 nightly
The price is $282 total per night from Nov 13 to Nov 14
$282 total
Nov 13 - Nov 14
Total with taxes and fees
Tombolo Talasso & Beach Resort
See all 4,472 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

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Montescudaio vacation package cost?
You can snap up a vacation package to this destination from $562 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.