Montescudaio Holidays

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Top Flight + Hotel Deals in Montescudaio

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

Aurum Firenze

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was €833, price is now €393 per person
€393
per person
22 Sept - 25 Sept
found 3 hours ago
Return direct flight included
Dublin (DUB) to Florence (FLR)
7.4/10 Good! (1,014 reviews)
Room was clean, breakfast was decent. In general, it was a good stay. Would likely consider staying again.

Reviewed on 30 Jun 2026

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Price was €890, price is now €412 per person
€412
per person
22 Sept - 25 Sept
found 3 hours ago
Return direct flight included
Dublin (DUB) to Florence (FLR)
7.6/10 Good! (1,004 reviews)
Highly recommended

Reviewed on 30 Jun 2026

Hotel San Luca

Hotel San Luca

4 out of 5
Cortona Old Town
Price was €816, price is now €489 per person
€489
per person
22 Sept - 28 Sept
found 1 day ago
Return flight included
London (LON) to Florence (FLR)
8.6/10 Excellent! (430 reviews)
Wonderful hotel with great view for Tuscany, good breakfast, perfect location to visit Cortona

Reviewed on 30 Jun 2026

Grand Hotel Torre Fara

Grand Hotel Torre Fara

4 out of 5
Save 100% on your flight
Price was €1,451, price is now €897 per person
€897
per person
19 Aug - 24 Aug
found 20 hours ago
Return flight included
London (LON) to Pisa (PSA)
9.6/10 Exceptional! (174 reviews)
Wonderful hotel, great location and fantastic staff

Reviewed on 15 Jun 2026

Hotiday Room Collection - Tirrenia

Hotiday Room Collection - Tirrenia

5 out of 5
Save 100% on your flight
Price was €939, price is now €610 per person
€610
per person
16 Aug - 21 Aug
found 14 hours ago
Return flight included
London (LON) to Florence (FLR)
7.6/10 Good! (31 reviews)
Front desk helpful 1 st day , 2 nd day man was rude . Property is clean except the showers have mold

Reviewed on 8 Jun 2026

Top hotels in Montescudaio

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 21 Jul 2025

Get rates
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
The price is €106 per night from 12 Jul to 13 Jul
€106
12 Jul - 13 Jul
includes taxes & 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 27 May 2026

Max Hotel Livorno
Castelfalfi

Castelfalfi

5 out of 5
Loc. Castelfalfi Montaione FI
The price is €863 per night from 7 Jul to 8 Jul
€863
7 Jul - 8 Jul
includes taxes & 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 2 Jul 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.

Frequently asked questions

How much does a Montescudaio holiday package cost?
You can snap up a holiday package to this destination from €393 on Expedia. However, how much your holiday 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?
Travel in the low or shoulder season and you're likely to score cheap Montescudaio holiday packages. Bear in mind that school holiday periods and local events and festivals can impact prices, so do some research before you go.
How many days is enough for Montescudaio?
With a well-organised itinerary, you can easily tick off the top Montescudaio attractions in a handful of days. But if you want to discover hidden spots or go on day trips, consider booking your Montescudaio holiday for longer.
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 holiday package as early as possible.
Is it cheaper to book a Montescudaio holiday as a package?
Expedia holiday 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 personalised Montescudaio holiday by choosing your favourite type of stay, airline and car class.
When to book a holiday 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.
How to plan a trip to Montescudaio?

  1. Choose the best time to travel: Your schedule, favourite season and the type of weather you like can all impact your decision on when to travel to Montescudaio.
  2. Set a budget: Factor in expenses such as food, flights and transportation when working out how much to set aside for your trip to Montescudaio. Then, select a hotel that works with your budget, whether that's an economical option or a deluxe retreat.
  3. Decide your trip length: Think about how much time you'd like to spend discovering Montescudaio. Plan your itinerary so you can get to all the experiences and attractions you're interested in without rushing.
  4. Combine your hotel and flights: Awesome destination, check. Length of stay, check. All that's left now is to choose a Montescudaio holiday package that brings all your bookings together.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.