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Apartment holiday rentals in Montescudaio

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Top-rated apartment rentals in Montescudaio

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Top guest favourite
The open-plan living area features wooden beams across the ceiling. Natural light filters through multiple windows, illuminating the cozy seating and dining areas. A rustic stone wall adds character, while a wooden table and light-colored chairs provide a functional dining space.
Flat in San Gimignano
4.97 out of 5 average rating, 237 reviews

Casa Irene

Casa Irene is a delightful Tuscan-style apartment, located on the second and top floor of a building just a 5-minute walk from the center, 50 meters to Porta San Matteo and another 50 meters to Via Francigena. Given the secluded location, it is easily reached by car to park in the immediate free parking. The apartment equipped with WiFi and air conditioning is divided into an open space living room/kitchen, bedroom and bathroom with shower and a large terrace overlooking the walls of San Gimignano

Top guest favourite
An inviting living space features a cozy fireplace framed by a rustic stone wall. Natural light filters through floral-patterned curtains, illuminating a spacious sitting area with a two-seater sofa. A four-poster bed draped in sheer fabric enhances the room's charm, complemented by decorative lanterns.
Flat in Caminino
4.91 out of 5 average rating, 183 reviews

Pieve di Caminino Historic Farm

Solo per amanti della natura. L'antica fattoria Pieve di Caminino, biologica, è un importante sito storico: ex pieve medievale sorta all'incrocio di due strade romane, ospitò due santi (la chiesa del XII secolo è oggi un museo privato, visitabile dagli ospiti, su appuntamento). Oggi copre 200 ettari di proprietà privata recintata, posta su una collina panoramica. Sette alloggi condividono una tenuta con piscina (stagionale), due laghetti, un uliveto centenario, vigneto e una foresta di sughere.

Top guest favourite
The image showcases a view of the Torre del Diavolo framed by lush greenery. Two bottles of wine are positioned in the foreground, enhancing the peaceful garden setting. Historic buildings with textured stone facades are visible, complementing the charming medieval atmosphere.
Flat in San Gimignano
4.98 out of 5 average rating, 151 reviews

Apartment at ground floor with garden

A refined and very central setting, between Piazza della Cisterna and Piazza del Duomo. The house has the rare value of combining a comfortable ground floor, with independent entrance, to a stunning view of the famous Devil's tower.The exclusive garden, equipped to dine outdoors, read or stay between flowers and towers, is an extraordinary oasis of peace and silence, just around the corner of the two lively main squares.Possibility of parking in a private box for a fee at a cost of €8.00 x day.

Top guest favourite
A terrace showcases a small table set with glasses and a bottle, complemented by two chairs. A scenic view of the Tuscan countryside can be seen in the background, revealing rolling hills and traditional rooftops under a bright sky.
Flat in San Miniato
4.99 out of 5 average rating, 156 reviews

San Miniato - Panoramic terrace in the historic center

Brand new apartment in the historic center of San Miniato. Recently renovated, it is ideal for those seeking tranquility in the heart of the city, with a beautiful view of the Tuscan countryside thanks to the panoramic terrace perfect for a breakfast in the sun or a special aperitif. Immersed in the historic part of the city, typical restaurants, shops and all the beauties of San Miniato can be easily reached on foot. Thanks to its central location, it is ideal for visiting all of Tuscany.

Top guest favourite
The rustic exterior of the stone cottage features a traditional red-tiled roof and large arched windows. Lush greenery and flowering plants surround the building, while the rolling hills of Tuscany are visible in the background under a clear sky.
Flat in Poggibonsi
4.91 out of 5 average rating, 105 reviews

San Martino Cottage with large panoramic terrace

45 sqm apartment in San Martino ai Colli, located along Via Cassia and surrounded by beautiful Tuscan countryside. Perfect for those who want to visit the attractions of the area: San Gimignano, Monteriggioni, Chianti, Siena (20 min.), Florence (30 min.), Volterra (40 min.). 2 minutes from the Florence-Siena highway junction and close to the urban center of Poggibonsi and Barberino-Tavarnelle. The house has a large terrace where you can relax and admire the Chianti hills.

Top guest favourite
A modern kitchen and dining area feature sleek cabinetry and a spacious dining table. White chairs surround the table, complemented by a vase of flowers. Large windows enhance the room's brightness, while neutral-colored tiles create a clean and inviting atmosphere.
Flat in Montescudaio
4.93 out of 5 average rating, 162 reviews

Elegant and bright apartment in Montescudaio

The apartment has been recently renovated, very bright and welcoming, the furnishings are modern and practically new. Located in the residential area of Montescudaio, quiet and peaceful from where you can easily reach the most characteristic places of Tuscany: medieval villages, enchanting hills and all the splendid historic cities (Pisa, Florence, Siena...) that make Tuscany such a popular destination. Just 20 minutes to the sea. Your vacation will be unforgettable!

Top guest favourite
A scenic view captures a lush landscape with rolling hills, vineyards, and olive trees under a colorful sunset. The traditional Tuscan casolare is visible in the background, surrounded by greenery, while the horizon features soft hues of orange and pink.
Flat in Poggibonsi
4.99 out of 5 average rating, 297 reviews

Laura Chianti Holidays

Laura Chianti Vacanze is the ideal solution for those seeking peace and tranquility immersed in the Chianti countryside. The apartment, halfway between Florence and Siena, is conveniently located for quick access to Florence, Siena, San Gimignano , Volterra, as well as the beautiful Chianti hills. The apartment offers private parking, two bedrooms, a fully equipped kitchen, private bathroom, private garden, barbecue, and a wonderful view of the Chianti hills.

Top guest favourite
A scenic view features a gentle hillside dotted with wildflowers, leading to the ancient Montemassi Castle perched atop. Olive trees are visible in the background, with a sky presenting a soft blend of clouds and blue hues.
Flat in Montemassi
4.97 out of 5 average rating, 115 reviews

Casa Sabina

The apartment, which provides your own private entrance, has been recently renovated and furnished with care. It is located at the foot of the ancient Castle of Montemassi in a historic square in the characteristic medieval village. With only pedestrian access allowed in this square, you can be assured to have a tranquil and peaceful stay. A 5 minute walk from the apartment, the Castle of Montemass provides visitors with a cultural activity during their stay.

Top guest favourite
An outdoor terrace features a round table adorned with colorful tiles at its center. Wooden folding chairs surround the table, and a large potted plant sits prominently. The view encompasses rolling hills and distant hilltop towns, framed by lush greenery.
Flat in Terricciola
4.88 out of 5 average rating, 130 reviews

Casa Cielo Independent and with amazing views

Immagina di svegliarti con le colline ornate di borghi e campanili a perdita d'occhio oltre la finestra della camera da letto: un'alcova con soffitti spioventi, travi e travicelli, pavimento in legno, in cima ad un antico casolare. Immagina da ogni affaccio della casa il sole che splende sulle vigne, oppure immagina il verde acceso degli uliveti dopo la pioggia primaverile oltre la grande terrazza adiacente alla cucina.

Top guest favourite
An independent building is surrounded by lush greenery, featuring blue shutters and a terracotta patio area. Small tables are set for outdoor seating. The expansive garden includes mature trees and various plants, creating a serene outdoor environment.
Flat in Palaia
4.96 out of 5 average rating, 124 reviews

Podere Le Murella "Sunset"

A cozy retreat for two, set among the green Tuscan hills. Enjoy a private patio for outdoor dining, large garden, free Wi-Fi, fully equipped kitchen, coffee machine, washing machine, dryer, barbecue area, and linens included. Private parking. Ideal for a romantic escape or relaxing stay near Pisa, Florence, Volterra, and charming villages. A perfect base to explore nature, art, and local life—all year round.

Guest favourite
A spacious living area features exposed wooden beams and warm, neutral tones. Comfortable seating is arranged around a light coffee table, with decor including a magazine and a small centerpiece. A fully equipped kitchen is visible in the background, complemented by natural light from nearby windows.
Flat in Peccioli
4.88 out of 5 average rating, 109 reviews

Da Vinci: entire space in the heart of Tuscany

Come and take a vacation at our beautiful apartment at Peccioli, Tuscany! Enjoy a renovated space, with A/C in the center if a medieval town next to bars, restaurants and shops. Beautifully decorated, with new appliances and furniture, high-speed internet, and all you need to enjoy your time in Italy. Peccioli is a gem in the heart of Tuscany, near all the big cities and touristic attractions.

Guest favourite
An outdoor dining area is highlighted by a wooden table surrounded by four white chairs. A parasol provides shade above the table, while a lemon tree adds greenery to the space, creating an inviting spot for al fresco meals.
Flat in Cecina
4.93 out of 5 average rating, 240 reviews

Cozy apartment in Cecina

45 sqm apartment arranged on a single floor with small garden that can be used for lunches and dinners outdoors. It includes: a living room with a sofa bed and kitchen, a bathroom and a bedroom. In the residential area of Cecina, 10 minute drive to sea. Parking is free throughout the apartment's street. The apartment is 15 minutes walk from Cecina train station. Bus stop 2 minutes on foot.

Popular amenities for Montescudaio apartment rentals

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Pisa
  5. Montescudaio
  6. Flat rentals