Villa holiday rentals in Province of Grosseto

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Top-rated villa rentals in Province of Grosseto

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Guest favourite

Villa in Montalcino

5.0 out of 5 average rating, 44 reviews

Breathtaking Views from a Tuscan Villa

We are offering our luxury villa as the setting for your dream Tuscan holidays. The restored tower-house is set within its own olive grove and surrounded by Brunello vineyards. High on the Val D'Orcia side of Montalcino, it enjoys picture perfect views. The village can be reached by a footpath in 15 minutes or by car in 5 mins. The villa benefits from air-conditioning throughout and underfloor heating; bedroom windows also have mosquito nets. The laundry room has a washing machine, iron and ironing board for guests’ use. The villa is perfect for a large family or two to four couples with children. The entire place is available to guests, with the exception of storage rooms in an annex outside the main building. Guests will enjoy exclusive use of the villa and its ground (including swimming pool). For extra safety, the swimming pool area is fenced and can be locked for children. Throughout the stay the guests will be able to contact our professional property managers who will also be able to help with extra activities (to be arranged separately). The villa is set high on the Val D'Orcia side of Montalcino and surrounded by Brunello vineyards. From here, the village is a picturesque 15-minute walk away where exceptional family-owned bistros and boutique shops are just waiting to be discovered. Notwithstanding the history of place, we strived to provide all modern comforts, such as TV with sound bar, a music system, a kitchen radio and a bluetooth speaker. Wifi is provided free of charge throughout the villa and also in the main outdoor spaces - including the pool area. The swimming pool is un-heated, however thanks to its natural, darker colour usually the water warms up more than white or light blue coloured pools. Please note that the swimming pool will be open from 15 May to 15 October - exceptions to be agreed upon based on length of stay / at extra cost.

4–11 Oct

$1,506 SGD per night

Guest favourite

Villa in Castiglion d'orcia

4.95 out of 5 average rating, 77 reviews

Villa Vignalunga

Discover paintings, found art, and original sculptures from room to room in this spacious villa. Old and new worlds collide as chic bathrooms share the space with ancient beamed ceilings. Admire sweeping countryside views from a stone terrace. Villa Vignalunga has been recently, uniquely constructed with traditional materials and preserves all the architectural details of the historic Tuscan farmhouses. Furnished with extreme taste with a mix of still old and modern but always in a rustic original style The villa is surrounded by 46 hectares of picturesque land boasting olive groves, lush vineyards, plentiful orchards, and meadows for grazing horses. Go for a scenic hike or drive to a nearby town for fresh local cuisine.

13–20 Nov

$1,055 SGD per night

Guest favourite

Villa in Castel del piano

5.0 out of 5 average rating, 48 reviews

Podere Noceto

Podere Noceto is the perfect place to discover the beauty of Tuscany with family and friends on all fours! The house is located between chestnut trees and olive trees on the slopes of Mount Amiata. It is the ideal base for exploring Pienza (30 minutes), Montalcino (30 minutes), Siena (1 hour), the sea of the Maremma (1 hour), thermal waters (Saturnia, San Filippo), and the local culture and gastronomy. The nearest village is Castel del Piano (2 Km) where you can find typical restaurants, supermarkets, pharmacy, etc.

6–13 Sep

$106 SGD per night

Guest favourite

Villa in Talamone

4.91 out of 5 average rating, 44 reviews

Villa Il Molinaccio with terrace and private beach

Large villa with panoramic terrace overlooking the sea and direct access from the house to the private sassed beach. It has large outdoor and indoor spaces for dining with company, garden, deckchair, umbrella, ping-pong and barbecue. Recently purchased kitchen and furniture. A 10-minute walk from the port and downtown, it offers privacy but accessibility to all amenities, including windsurfing, diving, beaches, and boat rentals. Large private garage in front of the house on private street. Recently renovated.

24–31 Dec

$767 SGD per night

Guest favourite

Villa in Monticchiello

4.95 out of 5 average rating, 44 reviews

Villa with garden. Il Giardino del Cardinale.

Villa "Il Giardino del Cardinale" is located in the historic center of the medieval village of Monticchiello, a hamlet of Pienza. The village is located in the heart of Val d 'Orcia inscribed on the list of Unesco sites. Stylish but at the same time characteristic villa is built over 3 levels. The peculiarity of the house is the enchanting private garden with beautiful views of the hills of Val d 'Orcia and all the comforts of staying in a historic center. In addition, the possibility of lunches and dinners

2–9 Dec

$984 SGD per night

Guest favourite

Villa in Capalbio

4.95 out of 5 average rating, 21 reviews

Capalbio, beautiful terrace overlooking the sea!

The house is newly renovated, located in the medieval village of Capalbio, the house has a wonderful terrace overlooking the beaches and the Argentario sea. It is equipped with independent heating, the Wi-Fi, a beautiful terrace, a garden adjacent to the house and all the comforts. It is ideal for families ,couples of friends, and those who want to spend pleasant moments at the sea and in nature, going to the Baths, walking and enjoying a great cuisine! Considering the possibility of hosting pets

13–20 May

$251 SGD per night

Guest favourite

Villa in Grosseto

4.89 out of 5 average rating, 18 reviews

Cheerful Villa with Pool First Floor

Independent apartment that occupies the entire first floor of a villa designed following ecological principles (solar panels, legnobloc). Large, quiet and comfortable; furnished with unique pieces in which the ancient blends with the contemporary, you can enjoy the spacious living area, immerse yourself in the tub in the lush bathroom or take a swim in the pool. Distances: historic center 5 minutes on foot; sea 12km; thermal baths 50 km; Maremma natural park 20 km; Rome/Florence/Pisa 1.5 h.

1–8 May

$170 SGD per night

Guest favourite

Villa in Montepulciano

4.98 out of 5 average rating, 99 reviews

Amazing Tuscany Villa, FREE parking

Modern villa with panoramic view in Montepulciano, a few steps from San Biagio. The villa is lovingly furnished and equipped with all comforts for a pleasant holiday. Enjoy breathtaking views of the surrounding countryside from the terrace, or relax in the two spacious gardens at your disposal. You will also have at your disposal a large kitchen to dabble in the magnificent art of cooking, something much loved by us Italians!!! Also available: Free Wi-fi Self check-in Reserved car parking

18–25 Dec

$354 SGD per night

Guest favourite

Villa in Montepulciano

4.96 out of 5 average rating, 74 reviews

Wine Experience Villa in Montepulciano

Villa Talosa è una residenza immersa tra i vigneti di "Fattoria della Talosa",Azienda vitivinicola di Montepulciano ove produciamo il Vino Nobile di Montepulciano d.o.c.g . Un luogo per godere di relax con una fantastica vista da ogni finestra della Villa. Distiamo 1.5 km dal centro storico,dove sarà possibile visitare la ns Cantina Storica risalente al 1500 A.D. e collocata sotto piazza Grande . Nota: Riscaldamento ed l’Aria condizionata sono dei costi aggiuntivi, in base al consumo.

7–14 Apr

$883 SGD per night

Guest favourite

Villa in Buonconvento

4.96 out of 5 average rating, 45 reviews

Bellagatta, an Enchanting spot in Val d'Orcia

A beautiful spot in the rustic Tuscan beauty. This untouched landscape of endless rolling hills covered with grain or sunflowers is the absolute protagonist in Valdorcia. Also a rich green valley encompasses the Orcia river, and don’t forget the vineyards for the renowned wines of Brunello or one of the many thermal baths of the region, such as the ones in Bagno Vignoni, where you can relax yourself. It is no wonder that this territory is protected as a World Heritage Site by UNESCO.

11–18 May

$470 SGD per night

Guest favourite

Villa in Montepulciano

4.95 out of 5 average rating, 116 reviews

A paradise in Montepulciano...

Villa Il Cubo is a full centralized air conditioned private house with large private swimming pool placed in the best garden spot for incredible views on the countryside around. Decoration has been updated with charming details that will make you enjoy the best Tuscany has to offer. We have electric vehicle charging point. Supermarkets, restaurants, grocery stores, wineries are just a few minutes away. IN JULY AND AUGUST WE LET FOR A MINIMUM OF 7 DAYS FROM SATURDAY TO SATURDAY!!!!!!

2–9 Feb

$547 SGD per night

Guest favourite

Villa in Monticchiello

4.98 out of 5 average rating, 111 reviews

Villa unesco heritage, Jacuzzi & garden. BB Daria

Carefully renovated and refurbished over a sustained period in order to maintain the original quality of its architecture, San Lorenzo Villa is open to guests. You are invited to enjoy the beauty, comfort and privacy of a beautiful independent villa in the centre of Monticchiello, from where you can have an incredible view on the Val d'Orcia, the UNESCO heritage! Don't forget a delicious breakfast (whatever you like) in our so close typical restaurant

9–16 Jan

$873 SGD per night