Luxury rentals in Province of Grosseto

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Popular amenities for Province of Grosseto luxury vacation rentals

Other great luxury vacation rentals in Province of Grosseto

Luxe
The villa is set amidst rolling hills, with a large pool surrounded by manicured grass. The driveway leads to the main house and guest house, framed by vibrant greenery and vineyards. A beautiful sunset casts a warm glow over the serene landscape.
Villa in Buonconvento
5 out of 5 average rating, 6 reviews

Podere Maiano

AnthonyRating, 5 stars26 months ago
Villa di Montesoli was an amazing experience for our entire multigenerational family. Our group consisted of 9 adults and 4 children including an 18 month infant. Pietro and the entire staff were beyond accommodating to all of us the entire week. The accommodations were fantastic with plenty of space for the entire family, with bonus spa room (hot tub, sauna and pool table). Outdoors we enjoyed family bocce. We were not in season to use the pool but it would be ideal for a summer stay. The location of the Villa is perfect for a memorable Tuscan vacation. The property expands many acres with fantastic views of hills and valleys within Val d’Orcia. We were able to visit Pienza, Montalcino, Montepulciano, Cortona, Siena and even Florenece from the Villa, in addition to a local farm, olive oil producer and wineries for tastings/tours all within our 7 day stay. We took advantage of breakfast and dinner each day at the Villa and the house cooks Giovanna and Daniela were wonderful and the food was amazing- true home cooked italian meals. They were also helpful shopping on our behalf at the local COOP for anything that we may require during the stay. We also enjoyed a fun and delicious pizza night with Ciro at the Villa - he was awesome. Pietro was very attentive during our stay and also had great communication prior to our trip. If you are looking for a true Tuscan experience, in an ideal location with a fabulous host look no further than Villa di Montesoli.
Luxe
A spacious terrace is showcased, framed by large potted plants and surrounded by sea views. The building features a modern design with large windows, allowing natural light to enhance the outdoor space, which is ideal for relaxation.
Place to stay in Porto Santo Stefano

Orietta

SusanRating, 5 stars13 months ago
The villa is modern and comfortable with private spaces and spectacular views of the sea and surrounding area. The differentiating factor for this property is the staff-Alex and Analyn, who are friendly and do everything to ensure guests feel at home. They made it a special holiday for all of us!
Luxe
An aerial view captures the villa surrounded by lush greenery and vineyards. The hilltop town of Montepulciano is visible in the distance, framed by rolling hills and an expansive sky featuring scattered clouds. The landscape showcases a harmonious blend of nature and historical charm.
Villa in Montepulciano
5 out of 5 average rating, 7 reviews

Villa Benefizio

SuzieRating, 5 stars8 months ago
A group of 7 friends just spent a wonderful week at Villa Beneficio. I have stayed in many AirBnBs around the world and the quality of service we received there was outstanding. Weeks before our arrival, we were in communication with Valentina and Tanjot, and they made sure that everything was ready for us. From organizing gravel bikes and e-bikes, delivered to the Villa, to a cooking class with Daniela and a visit to the cheese farm, everything was taken care of. One member of the group had a medical emergency during the week and they did everything they could to help him. Every day started with Natasha's delicious breakfast and cappuccinos. The pool area is beautiful with a view of Montepulciano in the background. We had a great time and hope to go back one day.
Luxe
A classic stone villa is set on manicured green lawns, with a private swimming pool reflecting the skies. Sun loungers are positioned nearby, inviting relaxation. Towering trees and shrubs frame the villa, enhancing its natural surroundings.
Villa in Siena
5 out of 5 average rating, 21 reviews

Il Fienile Di Montesoli

JenniferRating, 5 stars9 months ago
We loved our time at Pietro's villa - very clean, spacious and peaceful. It was extremely hot during our stay, but the A-C in the villa was strong and we were comfortable in the house. The beds are extremely comfortable. The villa's kitchen and bathrooms are well-appointed - plenty of cookware, towels, etc. We appreciated the cleaners restocking the tissues, shampoo & toilet paper during our stay. Having a washer and dryer was so convenient. Pool and grounds were very well maintained during our stay. Housekeeping came on Monday and Wednesday, but never came on Friday. No problem, except the kitchen trash can should be larger or extra trash bags supplied. We never had the chance to meet Pietro in person, but very much enjoyed talking with his warm and friendly father, Ghino. The views are lovely from the house, but a bit limited when sitting by the pool. Loved the pizza chef and cook experiences. Highly recommend this villa and would return!
Luxe
An infinity pool with a clear water surface extends towards the horizon, surrounded by lush green grass. A wooden pergola provides shaded seating, while rolling hills are visible in the background under a soft sky.
Villa in Val D'Orcia

Villa Ranuncolo

LoriRating, 5 stars23 months ago
Wonderful villa. Exceptional staff. Incredible views. Have stayed twice and will do so again.
Luxe
Villa in Radicofani
5 out of 5 average rating, 11 reviews

Villa Poggio Fibbia

JohnRating, 5 stars22 months ago
We have just returned from an amazing week staying at Villa Poggio Fabbia, where we were welcomed by the wonderful hosts Luis and Paloma. Nothing was too much trouble for them and the attention to the tasteful detail of the villa was a joy to experience. We were a group of six adults and a toddler of 2 years old; the villa was so luxurious, but felt so comfortable and homely. We cooked in for some evenings and found the kitchen well equipped and easy to use; we sourced all our shopping in Radicofani. Other evenings we did the short walk to the local vilage of Radicofani and followed some of te excellent recommendations of Luis as to where to eat and drink. We loved the villa gardens, stunning views and the gorgeous pool; each part of the day seemed to bring a different, but special charm to the the secluded setting of the villa. We also hired e-bikes from the village, which enabled us to explore the local area. We highly reccommend this villa and its generous and welcoming hosts.
Luxe
An aerial view showcases the villa set amidst rolling hills, surrounded by lush vineyards and greenery. A swimming pool reflects the sunlight, while the landscape extends toward distant mountains, creating a serene backdrop for relaxation.
Home in Buonconvento

Villa di Montesoli

Laurel LeeRating, 5 stars1 day ago
This is the greatest place on earth. It is more beautiful than the pictures even show. Every room is truly enormous and so beautifully designed. The view from every room is a dream - and from the outdoor dining and lounge area just heaven. We couldn’t stop saying it doesn’t look real. We were here on a work retreat from NYC and there is so much room for everyone to have privacy. It’s also more luxury than I even realized with really nice huge brand new bathrooms. The host helped us with everything and every recommendation was excellent. We hired the local chefs that were recommended and they were perfect - pizza in the outdoor pizza oven, delicious pasta and meats from local nonnas. Some of us came by the train from Florence and it was so easy into Buonconvento. Others drove (beautiful!!) and others took the recommended driver who took us at all hours to Rome and Florence airports - use him he’s great. The food at the local town is so good and easy to get to. Magical!!
Luxe
The outdoor area features a private swimming pool surrounded by wooden decking and sun loungers. Towering cypress trees are visible, along with a cozy gazebo. The farmhouse blends rustic architecture with modern amenities, set against a clear blue sky.
Villa in Radicofani

Beautiful modern villa with pool in Val D'Orcia

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