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House holiday rentals in Monticchiello

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Top-rated house rentals in Monticchiello

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Top guest favourite
An outdoor patio area is featured, showcasing a spacious covered space with large, light curtains that gently sway in the breeze. Comfortable seating options consist of bean bags and a dining table, all surrounded by lush greenery and tall cypress trees.
Home in Simignano
4.97 out of 5 average rating, 150 reviews

Casa al Gianni - The Simignano Barn

Transformed from an old barn, this luxurious retreat offers 5 bedrooms, 4 bathrooms, large equipped kitchen, large living room and a large private garden with parking, hot tub, patio with sofas, BBQ, fire pit and 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, between relaxation in the hot tub and outdoor dinners. A memorable getaway awaits you in this slice of paradise!

Top guest favourite
A scenic view reveals a medieval village perched on a hillside, surrounded by lush greenery and rolling hills. The buildings display a blend of architectural styles, set against a clear blue sky, illustrating the charm of the Tuscan countryside.
Home in Cetona
4.96 out of 5 average rating, 100 reviews

Case Aneris, Tosca - The most beautiful view of Cetona!

The stories of four generations have unfolded in the Aneris Houses. Thanks to the care and commitment of Aneris' children, today the Houses are two apartments equipped with all comforts, in an ideal location to enjoy the village - a three-minute walk from the square and the historic center - and explore enchanting places, where culture, nature, food and wine, and relaxation have been watchwords for centuries. The view of the Tuscan countryside and the medieval heart of the village are priceless.

Top guest favourite
The bedroom features a spacious bed adorned with floral bedding. Exposed wooden beams highlight the ceiling, while a decorative bicycle hangs on the wall. A contemporary fireplace adds to the room's character. Natural light filters through the open doorway, enhancing the inviting ambiance.
Home in Monticchiello
4.97 out of 5 average rating, 210 reviews

Il Focolare - Superior Tuscany Apartment

The "Il Focolare" apartment is located in the small medieval village of Monticchiello, inside the historic center, between the ancient walls. Immersed in the classic and enchanting landscapes of Tuscany with cypresses, rolling hills as far as the eye can see and winding white roads. Newly renovated (2019), it perfectly blends its historical soul with modern furnishings, giving the environment personality and charm, while the fireplace in the bedroom adds that extra touch of romance. Total 52 sqm

Guest favourite
A spacious outdoor pool is surrounded by neatly arranged lounge chairs and framed by lush greenery and tall cypress trees. The inviting blue water reflects the clear sky and the structure of the residence sits elegantly in the background.
Home in Asciano
4.96 out of 5 average rating, 101 reviews

Palazzo Monaci - Pool in the Crete Senesi

Welcome to Palazzo Monaci! An oasis of nature and unique beauty, in the heart of the Crete Senesi, in Tuscany. A residence with a pool and a breathtaking view of the Crete Senesi. Perfect for couples or families looking for a relaxing vacation. The location is perfect for exploring the surrounding areas. You can hike in the Tuscan countryside, visit the characteristic medieval villages, taste the delicious local wines, and immerse yourself in the culture and history of this fascinating region.

Top guest favourite
A quaint terrace is presented with a small round table and two chairs. Potted flowers add natural color, while a beautiful view of rolling hills and vineyards is visible in the background under a clear blue sky.
Home in Panzano
4.98 out of 5 average rating, 467 reviews

Old Farmhouse near Panzano Castle Abbacìo

The Abbacio apartment is part of an old farmhouse that has been restored respecting the original structure and style. Its location is just on the top of the hill, facing the valley. Surronded by vineyards and olive trees, but also attached to the village. From the house you can easily reach by feet wineries, farms and restaurants. Panzano is halfway between Florence and Siena, easily reached with car. By bus there is a good service from and to Florence, not from and to Siena. A very quiet spot!

Guest favourite
A view of the rolling hills and vineyards is framed by a window. The landscape features lush greenery and a clear blue sky in the distance, offering a serene and tranquil atmosphere.
Home in Montepulciano
4.92 out of 5 average rating, 145 reviews

Montepulciano Historic Center

nice and comfortable apartment in the old town of Montepulciano Placed in the Historical Centre, just a few steps to the most beautiful and oldest wine cellar in Montepulciano (Cantina del Redi dè Ricci) an amazing sixteenth-century structure, great-looking with its huge wine barrels. The apartment is in a perfect position: just a few minutes walk from the main square of the town, Piazza Grande(where, every summer, there are theatre and music events) but at the same time is a quiet district.

Top guest favourite
A cozy sitting area features a vintage leather sofa with colorful accents, positioned against a light wall adorned with contemporary wall art. Soft bedding is seen at the back, complemented by warm wooden flooring. Natural light filters through a nearby window, enhancing the inviting space.
Home in Montalcino
5 out of 5 average rating, 133 reviews

Montalcino Townhouse with Private Garden & Spa

A luxury apartment that blends traditional elements with all the modern comforts and some contemporary wall art. The apartment is centrally located in the upper part of town, only around the corner from the main square, in the limited traffic area. You can drive close by to download the luggage. The closest free car park is located at less than 10 minutes walk. Please note that to reach the house you need to walk a fairly steep street: it may not be ideal for those with mobility problems.

Top guest favourite
A vibrant garden features an array of colorful flowers, with delicate white blooms prominently displayed. In the background, rolling hills are seen under a dramatic sky, creating a serene landscape filled with natural beauty.
Home in Castiglione d'Orcia
4.95 out of 5 average rating, 106 reviews

Da nonna Ornella - nest in Val d'Orcia

Spectacular views and relaxation guaranteed in this romantic studio in the heart of Val d 'Orcia, province of Siena, immersed in beautiful Tuscany. Ideal for couples. It has a living area, equipped kitchen, bathroom, heating, private parking and a large and panoramic garden with sun loungers and hammock. Close to iconic destinations: PIENZA, Montepulciano, Montalcino, Bagno Vignoni, Bagni San Filippo, San Quirico d 'Orcia, Radicofani, Castiglione d 'Orcia, and Monte Amiata. Unforgettable!

Top guest favourite
A spacious living area features a gray sofa adorned with patterned cushions. A rustic wooden table and bookshelves filled with books are visible in the background, illustrating an inviting open layout that connects the living space to the dining area.
Home in Castiglione d'Orcia
4.95 out of 5 average rating, 152 reviews

Apartment in a detached villa - Val d'Orcia

In a detached villa, a cozy Tuscan-style apartment recently and tastefully renovated and located in a land rich in history. A few kilometers from the city of art and on the Via Francigena, the apartment can be a base for nature or food and wine tours. From a beautiful terrace overlooking the panorama you can enjoy your meals, admire the sunset and observe the majestic and magnificent medieval fortress From 03/22/18, municipal tourist tax: €1 per person from 12 years old

Top guest favourite
A view from the window reveals a serene landscape of rolling hills and valleys bathed in soft morning light. The garden below is adorned with colorful flowers and greenery, enhancing the tranquil atmosphere of the Tuscan countryside.
Home in San Quirico d'Orcia
4.99 out of 5 average rating, 218 reviews

Alma Vignoni - Vignoni Val d'Orcia - Bagno Vignoni

Alma Vignoni is an elegant and exclusive holiday house in Vignoni Alto that recalls Tuscan style and is enriched by unusual and personal details. The house consists of an open-space with fireplace in the center. On the one hand the room with stunning views over the surrounding hills (Pienza, Monticchiello and Montepulciano) on the other the kitchen area. Two cozy rooms overlook the ancient Via Francigena and the Orcia river valley. The bathroom has a large shower.

Top guest favourite
The exterior view captures a rustic stone house bordered by tall trees. A pathway leading to the dwelling is visible, accompanied by lounge chairs set on a grassy area. The tranquil setting reflects the peaceful ambiance of the countryside.
Home in Scrofiano
4.97 out of 5 average rating, 159 reviews

Jenny's Barn

The ancient barn, now finely restored, is located in the heart of the Valdichiana a few steps from the characteristic medieval village of Scrofiano. From the house you can enjoy a breathtaking view of the green Sienese hills where centuries-old olive trees and vineyards alternate from which the prestigious Chianti is obtained. Ideal for 2 people looking for a relaxing stay away from the chaos of the city. On request it is possible to add a baby bed and a cot.

Top guest favourite
A serene bedroom features a spacious bed with a simple white coverlet. A wooden chair with a striped cushion is placed beside a bench. Natural light filters through the two wooden windows, revealing views of the lush vineyards outside.
Home in Castelnuovo Berardenga
4.93 out of 5 average rating, 107 reviews

The Chianti window

A wonderful place to spend a few days in pleasant company. A large living room with fireplace where you can relax after returning from beautiful walks, bike rides, and excursions. The independent apartment is 15 km from Siena, 20 km from the Thermal Baths and 40 minutes from the villages of San Gimignano and Monteriggioni. Overall, there is a farm that produces wines and oil with the possibility of guided tours and tasting of our products with themed dinners.

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