Montescudaio Vacations from $1,122
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The Latest Montescudaio Vacation Packages
- Aurum Firenze
Oct 15 - Oct 20Aurum Firenze + Flight
Historic Centre of Florence4 nights4.0 star property7.4/10 - Good (1,001 reviews)Roundtrip • Boston (BOS) - Florence (FLR)BOS - FLR • 1 stop FLR - BOS • 1 stop$1,565$1,122found 1 day agoper traveler - Aurum Uffizi
Oct 15 - Oct 20Aurum Uffizi + Flight
Historic Centre of Florence4 nights4.0 star property7.6/10 - Good (1,002 reviews)"The location of this hotel is fantastic and central to all the major sights. We were able to walk to every major landmark between 4-10 minutes. The staff were lovely and hard working. The AC, shower/hot water worked great. The breakfast was a typical continental style and I found it satisfactory to a hotel this size. The one thing that was challenging was getting a regular wifi signal. Overall, great stay for a family of 4."Reviewed July 24, 2026Roundtrip • Boston (BOS) - Florence (FLR)BOS - FLR • 1 stop FLR - BOS • 1 stop$1,726$1,157found 1 day agoper traveler - Hotel La Scaletta Al Ponte Vecchio
Oct 15 - Oct 20Hotel La Scaletta Al Ponte Vecchio + Flight
Historic Centre of Florence4 nights4.0 star property9.0/10 - Wonderful (1,000 reviews)"Never stayed in a palace! What an experience! Everything was 100% or more!"Reviewed July 21, 2026Roundtrip • Boston (BOS) - Florence (FLR)BOS - FLR • 1 stop FLR - BOS • 1 stop$1,955$1,363found 1 day agoper traveler - Hotel Palazzo Ognissanti
Sep 9 - Sep 15Hotel Palazzo Ognissanti + Flight
Historic Centre of Florence5 nights4.0 star property7.8/10 - Good (493 reviews)"Front of house was friendly, helpful and polite. Showed us where to go, stored our luggage safe and when we came back to check in they had taken cases upstairs for us! Room was basic but clean. Lovely view of Duomo. I was offered a complementory bottle of wine which was red(i only drink white) and they were so accomodating- bringing up a tray eith crisps and ice bucket too. Breakfast was nice, basic bit almost we needed. Closest to the train station, supermarket and fruit and veg shop...."Reviewed May 21, 2026Roundtrip • New York (NYC) - Florence (FLR)JFK - FLR • 1 stop FLR - JFK • 1 stop$2,142$1,601found 10 hours agoper traveler - L'Andana
Sep 19 - Sep 24L'Andana + Flight
Castiglione della Pescaia4 nights5.0 star property9.4/10 - Exceptional (91 reviews)"Breathtaking views of the Tuscan countryside, as well as incredibly attentive staff."Reviewed June 9, 2026Roundtrip • New York (NYC) - Florence (FLR)EWR - FCO • 1 stop FCO - JFK • 1 stop$2,331$1,772found 1 day agoper traveler
Montescudaio Hotel Deals
Riparbella Country Suite
Riparbella Country Suite
Hotiday Toscana Riparbella
Hotiday Toscana Riparbella
Casa Cerboneschi
Casa Cerboneschi
Punti Di Vista B&B Food&Wine Experience
Punti Di Vista B&B Food&Wine Experience
Vintage Hotel Tornese - Business & Events
Vintage Hotel Tornese - Business & Events
Relais Sant'Elena
Relais Sant'ElenaFrequently Asked Questions
How much does a Montescudaio vacation package cost?
You can snap up a vacation package to this destination from $1,122 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.