
House vacation rentals in Montescudaio
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Top-rated house rentals in Montescudaio
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Casa al Gianni - The Simignano Barn
Converted from an old barn, this luxurious retreat offers 5 bedrooms, 4 bathrooms, a large fully equipped kitchen, a spacious living room, a large private garden with parking, a hot tub, a patio with sofas, a BBQ, a fire pit, and an outdoor kitchen. Ideal for those looking for a unique experience, it combines rustic charm with modern comforts. Perfect for families or groups, it promises magical evenings under the stars, including relaxation in the hot tub and outdoor dinners. A memorable getaway awaits you in this slice of paradise!

The Gegia Matta
In the green of Tuscany La Gegia Matta is the guesthouse of Villa Ruschi, a magnificent eighteenth-century property characterized by the typical Tuscan style. It is located in the center of Calci, in Val Graziosa and is easily accessible both by car and motorcycle. Nearby you will find restaurants, wine bars, groceries and you can also visit the beautiful Certosa di Calci. It is 10 minutes from Pisa, 20 minutes from Lucca , 1 hour from Florence and 20 minutes from the beaches of the Tyrrhenian coast.

Podere Quercia al Santo [Quercia al Santo Estate]
Portion of a farmhouse, located in the hills of Lajatico overlooking the Teatro del Silenzio. The perfect place for those who want to spend a regenerating vacation, in contact with nature, in tranquility, but at the same time love to visit nearby villages and cities. Suitable for couples, families with children and 4-legged friends. The house, surrounded by a beautiful garden, has a double bedroom, a small bedroom, a living room with a sofa and an equipped kitchen. Parking space and private garden

Open space surrounded by nature
Casa Namaste is a small stone cottage with well-kept interiors 1 km from the medieval village of Montescudaio. The house is completely surrounded by woods and centuries-old oaks. 150 meters away flows the Cecina river. In the 5000 square meter garden there is a natural spring with a large stone tub to cool off and an outdoor hot shower surrounded by greenery. We have a Vodafone adsl line with download 33 and upload 1.4. Smart TV and air conditioning are also available starting this spring

Design loft with private SPA in Tuscany
Welcome to Loft SPA, your personal refuge in the heart of Massa Marittima, an exclusive accommodation equipped with a private indoor swimming pool. This unique property offers an unparalleled stay experience, combining elegance and comfort, the accommodation has been designed with attention to detail and quality, The highlight is the indoor swimming pool with its accessories, an oasis of relaxation. This exclusive accommodation offers a stay experience you will not easily forget.

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.

Casa Maurino
"Casa Maurino", in the historic center of San Gimignano, is a delightful apartment nestled in the ancient city walls. Ideal place to spend short stays, immersing yourself in the evocative atmosphere of the medieval village. Located in a quiet and peaceful position with a panoramic terrace overlooking the Tuscan hills to indulge in romantic moments of relaxation. Independent entrance from a characteristic stone staircase, panoramic terrace. Suitable for couples.

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.

Nada Home
In my home, you can experience the most authentic side of Tuscany, filled with peace, warmth and family traditions. Surrounded by olive groves and vineyards in the heart of Chianti, you will have a private garden all to yourself, where you can relax in complete tranquillity. On request, you can join a cooking class in the house, preparing our family recipes handed down by Grandma Graziella, or share a special dinner in an intimate and welcoming atmosphere.

Enjoy Amazing View in Tuscany in Our Country House
An amazing experience between nature, flavor and relax in the heart of Chianti. Situated between Barberino Tavarnelle, San Gimignano, Greve in Chianti, and Florence, Belvedere 27/A overlooks the Santa Maria Novella Castle, amidst vineyards and olive groves with an amazing view. A countryside Tuscan home, surrounded by greenery and olive’s fields, equipped with every comfort. Reconnect in this serene, one-of-a-kind stay, for a peaceful and relaxing holiday.

Frontemare house with exclusive sea access
Casa Frontemare is a completely renovated property with direct access to the sea, from which you can enjoy a panoramic view of the sea, the Tuscan islands and wonderful sunsets. It is a perfect place for those who love a relaxing and private vacation. The proximity to the Tuscan art cities and the small typical villages means that it is also possible to discover new places and discover the flavors of Italian cuisine.

Cercis - La Palmierina
The apartment is part of a completely fenced estate of 60 hectares of unspoiled nature: more than 1000 olive trees, countless cypresses and fragrant forests create an idyllic environment for those seeking tranquility and silence. The Palmierina estate is near Castelfalfi (a true jewel of medieval architecture) and close to Florence (50 Km), Siena (50 Km), and Pisa (50 Km). There are two golf courses nearby.
Popular amenities for Montescudaio house rentals
House rentals with a pool

Collina Power

Infinity pool in Chianti 1

Borgo Ripostena – n. 8 Casa Vecchia

Ancient Barn in Chianti with Pool

SuiteLouise.pool, Hot Tub,homeGym & private Garden

Paluffo Torre House

Le Rose Apartment in Tuscany

Casa Luigi Suite with exclusive pool
Weekly house rentals

Chalet i Poggetti,

Japandi apartment with a view!

Countryside-panoramic sea Casale Marittimo Tuscany

Stylish Gem in Historic Lajatico

La Romantica (Hot Whirlpool)

La Bandita Dependance

The Porrine Ferienhaus IV

Appartamento La Mignola
Private house rentals

[10 min from the sea] Apartment with garden + Jacuzzi

Villino Isotta (exclusive private villa)

House with view of olive trees, 10 minutes from the sea

Charming Tuscan Villa with pool

Le Piccole Scalette "Under the Tuscan Sun"

Old country house with a view!

Villa Siloral a jewel in the Etruscan Coast

Panoramic villa with swimming pool, Volterra view
Destinations to explore
- Elba
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Piazza del Duomo (Pisa)
- Cala Violina
- Stazione Santa Maria Novella
- Pisa Centrale Railway Station
- Uffizi Gallery
- Spiagge Bianche
- Fortezza da Basso
- Gulf of Baratti
- Piazza della Repubblica
- Parco delle Cascine
- Del Chianti
- Gorgona
- Piazzale Michelangelo
- Capraia
- Pitti Palace
- Palazzo Vecchio
- Piazza della Signoria
- Boboli's Garden





