Montescudaio vacation rentals
Vacation rentals in Montescudaio by owner — compare homes, condos and cabins, message verified hosts, and book direct with no service fees.
Montescudaio in Tuscany, Italy, offers a unique blend of historical architecture and scenic landscapes. With vineyards and olive groves dotting the backdrop, this quaint town provides an authentic Tuscan experience. On Houfy, you can book accommodations in Montescudaio, ensuring a more personal and cost-effective stay. Walk along the narrow streets where history echoes through ancient buildings, and enjoy local wines at traditional trattorias. Explore nearby attractions such as the medieval towns of Volterra and San Gimignano for a full exploration of Tuscany's rich offerings.
Recommended Homes in Montescudaio
Handpicked properties we think you'll love in Montescudaio.
€241.00 EUR total for 3 nights
Oct 9 – 12, 2026
€272.00 EUR total for 3 nights
Sep 26 – 29, 2026
€624.00 EUR total for 5 nights
May 17 – 22, 2027
Why visit Montescudaio
Discover what makes Montescudaio a perfect vacation rental destination.
Etruscan Heritage Sites
Discover Etruscan ruins just outside town.
Explore the ancient site of Parco Archeologico di San Silvestro, located 12 miles from Montescudaio, showcasing Etruscan and Roman artifacts.
Tuscan Wine and Cuisine
Savor local Chianti and authentic dishes.
Visit Azienda Agricola Serni Fulvio Luigi, just 2 miles from the city center, for tastings of local wines and olive oils.
Rolling Tuscan Countryside
Hiking trails with scenic views.
Hike through the Cecina River Park, located just 5 miles away, offering trails surrounded by lush Tuscan landscapes.
Family-Friendly Activities
Amusement parks and wildlife centers nearby.
Spend a day at Cavallino Matto amusement park, 22 miles away, offering rides and attractions for all ages.
Where to stay in Montescudaio
The best areas and neighborhoods for your vacation rental in Montescudaio.
Centro Storico
Marvel at narrow cobblestone streets lined with medieval architecture and enjoy local shops and cafes.
Val di Cecina
Known for its stunning landscapes and outdoor activities, Val di Cecina offers hiking and nature exploration.
Querceto
A charming village with a focus on organic farming and sustainable living, offering unique agritourism experiences.
Guardistallo
Offers panoramic views of the sea and hills, with several bed and breakfasts and traditional restaurants.
Find Montescudaio vacation rentals that suit your style
Villas and more — pick the kind of Montescudaio vacation rental you want, then book it direct with the host.
Montescudaio vacation rentals with free WiFi, air conditioning or kids friendly
Free WiFi, air conditioning, kids friendly and more — every Montescudaio vacation rental here is listed by a verified host and bookable direct, with the price the host set.
Top attractions in Montescudaio
All within driving distance of Montescudaio vacation rentals.
Chiesa di Sant'Alessandro
This historical church dates back to the Middle Ages and features stunning frescoes. · 0.2 miles
Riserva Naturale di Montenero
A protected area offering trails through lush forest and rare wildlife. · 15 miles
Etruscan Museum of Cecina
Displays an extensive collection of Etruscan artifacts and history. · 12 miles
Il Giardino Sospeso
An adventure park offering tree climbing and zip-lining, perfect for families. · 18 miles
La Carabaccia
A local favorite serving traditional Tuscan dishes with homemade ingredients. · 0.1 miles
Teatro Comunale di Guardistallo
Hosts musical and theatrical performances year-round in a historic venue. · 3 miles
Getting to and around Montescudaio
Navigating Montescudaio is best done by car for flexibility in exploring its beautiful surroundings.
- PISA INTERNATIONAL AIRPORT
- Located 38 miles from Montescudaio with numerous international and domestic flights.
- FLORENCE AIRPORT
- Situated 70 miles away, offering a range of European connections.
- CAR RENTAL
- Available at Pisa Airport and in the town center, ideal for regional exploration.
- PARKING
- Free parking spots are available in most neighborhoods and town areas.
Similar vacation rentals near Montescudaio
Homes within 60 miles of Montescudaio, from verified hosts.
€1,604.00 EUR total for 3 nights
Oct 7 – 10, 2026
€383.50 EUR total for 3 nights
Sep 26 – 29, 2026
€493.05 EUR total for 3 nights
Sep 26 – 29, 2026
$1,228.00 USD total for 3 nights
Oct 17 – 20, 2026
€365.85 EUR total for 3 nights
Sep 26 – 29, 2026
€360.00 EUR €306.00 EUR total for 3 nights
Sep 29 – Oct 2, 2026
€423.50 EUR total for 3 nights
Sep 29 – Oct 2, 2026
€648.00 EUR €591.60 EUR total for 3 nights
May 1 – 4, 2027
€180.00 EUR €162.00 EUR total for 3 nights
Oct 11 – 14, 2026
€425.00 EUR total for 3 nights
Sep 27 – 30, 2026
€680.00 EUR total for 3 nights
Jan 2 – 5, 2027
$355.00 USD total for 7 nights
Sep 26 – Oct 3, 2026
Explore near Montescudaio
Cities and towns within driving distance of Montescudaio, each bookable direct with the host.
Direct with the host
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Itemised pricing
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More vacation rental destinations around Montescudaio
Frequently asked questions
Quick answers about booking vacation rentals in Montescudaio and what direct booking on Houfy actually means.
Vacation rentals in Montescudaio average around €80-€150 per night depending on location and amenities.
Yes, several rentals in Montescudaio welcome pets. Always check individual listings for specific pet policies.
Centro Storico and Querceto are popular neighborhoods for their charm and proximity to attractions.
The best time to visit is during spring (April to June) and autumn (September to October) for mild weather and fewer tourists.
Houfy offers a variety of rentals in Montescudaio, from rustic farmhouses to modern apartments with stunning views.
Vacation rentals offer more space and home-like amenities. You can cook your meals and enjoy more privacy compared to hotels.
Experience Tuscan farm life in Val di Cecina or explore medieval ruins and Etruscan history just outside the town.
Houfy is a platform for vacation rentals. Guests book directly with hosts, paying the listed price.
Yes, Houfy is a secure platform that connects guests directly with hosts for transparent and safe transactions.