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Holiday rentals in Montescudaio

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Top-rated holiday rentals in Montescudaio

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
A modern kitchen features sleek cabinetry in light tones and equipped with essential appliances. A small dining area is present, with minimal decor. Natural light enters through a glass door that opens to a small balcony, enhancing the space's airy feeling.
Flat
4.94 out of 5 average rating, 170 reviews

Appartamento elegante e luminoso a Montescudaio

L'appartamento è stato ristrutturato recentemente, molto luminoso e accogliente, gli arredi sono moderni e praticamente nuovi. Situato nella zona residenziale di Montescudaio, tranquilla e silenziosa da dove si possono raggiungere facilmente le più caratteristiche località della toscana: borghi medievali, colline incantevoli e tutte le splendide città storiche(Pisa,Firenze,Siena...)che fanno della Toscana una meta tanto ambita. A soli 20 minuti dal mare. La vostra vacanza sarà indimenticabile!

Guest favourite
A natural stone pool surrounded by a brick border reflects the greenery of the surrounding trees. A charming cottage with large windows can be seen in the background, accompanied by a small dining setup, enhancing the serene outdoor setting.
Home
4.96 out of 5 average rating, 127 reviews

Open space immerso nella natura

Casa namaste è un piccolo casolare in pietra con interni curatissimi a 1 km dal borgo medievale di Montescudaio La casa è completamente circondata da bosco e querce secolari a 150 metri scorre il fiume Cecina nel giardino di 5000 metri quadrati c'è una sorgente naturale con una grande vasca in pietra per rinfrescarsi e una doccia calda esterna immersa nel verde..abbiamo una linea adsl Vodafone con download 33 e upload 1.4..da questa primavera è inoltre disponibile smart TV e climatizzatore

Superhost
Apartment
4.88 out of 5 average rating, 8 reviews

La "Tana del Riccio"

Located in a monastery from the 1700s, just a few steps from the delightful medieval village of Montescudaio, the "Tana del riccio" is a small nest immersed in the peace and greenery of the Tuscan countryside. Conceived as a place of retreat and "good rest" here you can enjoy that silence. In this place, you will not find anything that could represent a distraction from the most beautiful things that nature can offer: no internet, television, no connection other than that with yourself.

Superhost
A spacious glass-enclosed veranda features a large dining table surrounded by comfortable chairs. The high wooden ceiling adds charm, while views of the lush garden and grassy area create a serene atmosphere. Natural light floods the space through expansive glass windows.
Farm stay
4.72 out of 5 average rating, 90 reviews

Countryside apartment in villa close to the beach

Montescudaio, one of the most beautiful villages in Italy and located in the Val di Cecina, is the setting for the Agriturismo Il Polveraio, located in the open countryside and in the middle of an olive grove, with a view of the nearby Tyrrhenian Sea and the Tuscan Archipelago. The agriturismo offers various accommodations located in the main house, dating back to the 11th century AD, and in two outbuildings and will allow you to experience a stay in total peace and tranquillity.

Top guest favourite
An aerial view of the property reveals a charming red house surrounded by lush greenery. Tall cypress trees and vibrant bushes create a tranquil landscape, while an expansive lawn features relaxing loungers, inviting guests to enjoy the serene atmosphere of the Tuscan countryside.
Home
5 out of 5 average rating, 217 reviews

Il Fienile, Luxury Apartment in the Tuscan Hills

‘Il Fienile’ is in an enchanting position immersed in the beauty of the Tuscan hills, with a breathtaking view of the surrounding countryside. It is located in the hamlet of Catignano in Gambassi Terme, just a few kilometres from San Gimignano. The house sits in a protected oasis surrounded by a beautiful private park with olive trees, a pond, pine trees and woods, where you can walk, relax and enjoy the pleasures of unspoilt nature. A unique experience entirely to be enjoyed.

Top guest favourite
Apartment
5 out of 5 average rating, 49 reviews

AnticaVista, Luxury Apartment with Tower Views

A hidden gem nestled within the ancient walls of a 14th-century tower house, right in the heart of San Gimignano, a UNESCO World Heritage Site. This one-of-a-kind apartment is where history meets contemporary elegance. Look out the window and you’ll feel like you can almost touch the medieval towers. The view is breathtaking: unforgettable glimpses of the majestic Torre Grossa, framed by the iconic skyline that earned San Gimignano its nickname, the “Medieval Manhattan.”

Top guest favourite
The exterior of a rustic farmhouse is highlighted, featuring warm-colored walls and a traditional tiled roof. A large tree stands prominently, while outdoor seating is arranged on the grassy area, offering a serene atmosphere surrounded by lush greenery and a partially cloudy sky.
Farm stay
4.94 out of 5 average rating, 179 reviews

Casa al Gianni - Olmo

Ciao, siamo Cristina e Carmelo! Vi aspettiamo a "Casa al Gianni", il nostro agriturismo tra i boschi della Montagnola Senese a soli 20 minuti da Siena. Qui la vita rallenta: Solo il profumo della terra, il canto degli uccelli e la simpatia dei nostri animali. È un invito a riscoprire la bellezza delle piccole cose, immersi nel verde della Toscana più vera. Non è solo una vacanza, è un ritorno alle origini. Questo angolo di pace vi resterà nell'anima. Vi aspettiamo!

Guest favourite
An outdoor patio features a large umbrella providing shade over a black dining table and four chairs. A lounge chair is positioned on the grassy area, surrounded by lush green plants and shrubs. A stone wall and arched window add rustic charm to the setting.
Flat
4.82 out of 5 average rating, 129 reviews

Casetta Sole View over Tuscany Hills and Sea

Casetta Sole is a cozy Tuscan home with equipped garden, at the foot of Montescudaio village, Costa degli Etruschi, a step from the countryside. View over green hills, vineyards, olive groves and sea in the valley. Super-fast Wi-Fi (ideal for smart working), free parking + EV charging station. Garden with barbecue. Few km from the sea, on the Wine Route: near Volterra and San Gimignano, perfect for relaxation, wine tours and DOC tastings. Welcome to our Tuscany!

Top guest favourite
Home
4.99 out of 5 average rating, 141 reviews

House with a breathless view in Tuscany

Halfway between Pisa and Florence, this dreamy Tuscan house is your perfect escape. Lounge on the panoramic terrace with sun-kissed views, sip your morning coffee, or enjoy al fresco dinners under the golden sunset. Nestled in the heart of a charming village turned open-air contemporary art museum, every corner feels like a picture-perfect moment. Peccioli is your gateway to Tuscany’s art cities or a serene hideaway to savor the magic of authentic local life.

Guest favourite
Dome
4.97 out of 5 average rating, 104 reviews

Green Dome @ The Land Before Time Retreats

Nestled among Tuscan olive groves between Volterra and San Gimignano, The Land Before Time – Quad & Saddle Retreats offers 4 Green Domes with private jacuzzi, en-suite bathroom, air conditioning and Wi-Fi. Enjoy breakfast each morning in the Cupola Lounge with stunning views. During your stay, experience horseback rides through scenic trails, quad tours to discover hidden Tuscany, or simply relax under the starry sky.

Guest favourite
Flat
4.93 out of 5 average rating, 84 reviews

La Suite del Borgo

Confortevole e grazioso bilocale appena ristrutturato situato nel cuore del centro storico di Montescudaio. La Suite dispone l 'utilizzo di un'ampia terrazza che offre un panorama mozzafiato che va dalle colline al mare con affaccio sulle isole dell'arcipelago toscano. Situato in posizione strategica sia per godersi una vacanza al mare che per rilassarsi nella tranquillita' di un borgo medioevale

Top guest favourite
Holiday home in Lajatico
5 out of 5 average rating, 27 reviews

Rosa: Tuscan Views & Pool, Walk to Town

Welcome to La Lunaria di Lajatico, an elegant residence in the Tuscan hills, just a 7-minute walk from the village of Lajatico, hometown of Andrea Bocelli. With two pools, panoramic terraces overlooking rolling hills, olive groves, BBQ, and full modern comfort, it offers four rustic-chic apartments—ideal for families, couples, or groups seeking authentic Tuscany close to town.

Popular amenities for Montescudaio holiday rentals

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Pisa
  5. Montescudaio