Montescudaio Vacations from $1,240
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The Latest Montescudaio Vacation Packages
- Aurum Uffizi
Aug 23 - Aug 29Aurum Uffizi + Flight
Historic Centre of Florence5 nights4.0 star property7.6/10 - Good (1,001 reviews)"Clean room, close to all major attractions, friendly staff ready to help always, good breakfast."Reviewed July 13, 2026Roundtrip • Boston (BOS) - Florence (FLR)BOS - FLR • 1 stop FLR - BOS • 1 stop$1,731$1,240found 1 day agoper traveler - Residenza Florentia
Sep 27 - Oct 3Residenza Florentia + Flight
Historic Centre of Florence5 nights1.0 star property8.4/10 - Very Good (53 reviews)"Staff was helpful, the property was not very well maintained."Reviewed June 1, 2026Roundtrip • Miami (MIA) - Florence (FLR)MIA - FLR • 1 stop FLR - MIA • 1 stop$1,986$1,373found 2 days agoper traveler - Relais Uffizi, Tailor made Hotel
Sep 27 - Oct 3Relais Uffizi, Tailor made Hotel + Flight
Historic Centre of Florence5 nights4.0 star property9.4/10 - Exceptional (152 reviews)"Firstly this hotel is on a side street and not easy to find. We arrived with two young children on an intense heat wave day to check in for a confirmed, family room booked through Expedia. At check-in we were told the air conditioning in our room was broken. They made no attempt to inform us in advance of the issue or rebook us into a different room. The front desk declined to move us to another room and offered only a refund — which doesn’t help when an equivalent room for the same dates now..."Reviewed July 2, 2026Roundtrip • Miami (MIA) - Florence (FLR)MIA - FLR • 1 stop FLR - MIA • 1 stop$2,104$1,503found 2 days agoper traveler - Hotel Regency
Sep 15 - Sep 21Hotel Regency + Flight
Historic Centre of Florence5 nights5.0 star property9.4/10 - Exceptional (457 reviews)"The staff at the hotel were really at our service. The knew my name, responded quickly and were happy to help. The breakfast area is a beautiful place to eat. The marble bathroom was stunning and are the bedroom was decorated in such a grand way. I would stay there again happily."Reviewed June 19, 2026Roundtrip • Boston (BOS) - Florence (FLR)BOS - FCO • 1 stop FCO - BOS • 1 stop - Il Rivalta - Place of Charme
Sep 19 - Sep 24Il Rivalta - Place of Charme + Flight
Historic Centre of Florence4 nights4.0 star property9.2/10 - Wonderful (561 reviews)"Location was fabulous by the river. Staff attentive and helpful. Rooms bright and airy with great view of the river. Would definitely recommend. Thanks"Reviewed July 16, 2026Roundtrip • Boston (BOS) - Florence (FLR)BOS - FLR • 1 stop FLR - BOS • 1 stop
Montescudaio Hotel Deals
Residence Riva degli Etruschi
Residence Riva degli Etruschi
Podere l'Agave
Podere l'Agave
Acquaviva Experience Hotel
Acquaviva Experience Hotel
Frequently Asked Questions
How much does a Montescudaio vacation package cost?
You can snap up a vacation package to this destination from $1,240 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.