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Vacation rentals in San Regolo

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Popular amenities for San Regolo vacation rentals

Other great vacation rentals in San Regolo

Guest favorite
An aerial view of the Borgo Iesolana estate is captured, showcasing the lush green landscape dotted with olive trees. The property features multiple swimming pools surrounded by well-maintained lawns, blending seamlessly into the tranquil countryside.
Apartment in Pogi
4.94 out of 5 average rating, 89 reviews

Borgo Iesolana Suite Superior

RobertRating, 5 stars3 weeks ago
5 Stars – A Tuscan Dream Come True! Our stay at Francesco’s private resort-style retreat in the hills of Tuscany was absolutely magical. The location is stunning—peaceful, picturesque, and the perfect escape into the beauty of the Italian countryside. The rustic room had so much charm and comfort, and the property itself was amazing, with not one but two beautiful pools to relax by. One of the highlights was the on-site restaurant. The free breakfast was far beyond the typical offering—not just muffins, but a full, authentic Italian breakfast that we looked forward to each morning. Dinner was just as impressive, showcasing delicious local flavors and warm hospitality. It was also a great jumping-off point for exploring the region—we took a lovely day trip to Siena with ease. This place is a hidden gem, and we’d return in a heartbeat. Highly recommended for anyone looking to experience the best of Tuscany!
Top guest favorite
A stone farmhouse is framed by lush greenery and a vibrant sky. Outdoor seating is provided under a wide umbrella, surrounded by potted plants. Steps lead down from the patio area, enhancing accessibility to the garden.
Home in Castelnuovo Berardenga
4.97 out of 5 average rating, 35 reviews

Casa il Cipresso

DebbieRating, 5 stars3 weeks ago
Guilia, Donatella & Antonio were excellent to deal with responding very quickly to any questions. This is the cleanest air b & b I have ever stayed in and very well equipped (lots of coat hangers!!) The view from the patio at the rear of the property is so beautiful and peaceful. All we wanted to do was sit and enjoy the nature. Village centre only 5 minutes by car where there is several restaurants (best to make reservation) of varying price ranges. You can also walk into village. If you cross the main road at the bottom of the track to the air b & b you can walk on a track through the olive trees and come out in the village centre save walking on road). Small but excellent supermarket (closed on Sunday) 10 minute by car. Lots of interesting places to visit nearby. Enjoy your stay.
Top guest favorite
An independent stone house is framed by a wooden fence, set against a backdrop of green hills. Bright blue skies enhance the natural scenery, while a large window invites views of the surrounding landscape.
Home in Bucine
4.96 out of 5 average rating, 80 reviews

The Biricocolo Cottage

PaulRating, 5 stars1 month ago
Serene, tranquil, verdant: a profoundly beautiful place. We just loved it. Chiara and her mother could not have been more friendly and helpful. We were there a few days for a wedding nearby. We can't wait to return for a full holiday. Well done super hosts! Thank you. Paul and Bridget
Guest favorite
A modern kitchen is showcased, featuring sleek cabinetry in neutral tones. A sink and gas cooktop are present, accompanied by a decorative arrangement of glassware and a small plant on the shelf above. Soft lighting enhances the clean lines and minimalist design.
Apartment in Castelnuovo Berardenga
4.88 out of 5 average rating, 26 reviews

Colle ai Lecci: Design Apartment in Tuscany

JamesRating, 5 stars2 weeks ago
Beautiful property and a spotless, stylish room. The host was incredibly kind and attentive—made us feel right at home. Would definitely stay again!
Top guest favorite
The stone exterior of the villa features rustic architecture with wooden shutters. Sunlight casts shadows across the lawn, highlighting the surrounding trees. A pathway leads to the entry, framed by lush greenery.
Home in Radda in Chianti
5 out of 5 average rating, 20 reviews

Villa le Scope 5*

ColeRating, 5 stars3 weeks ago
Beautiful home. Extremely clean. Riccardo was extremely responsive and made our check in process very easy. Definitely would stay again!
Top guest favorite
An ornate wrought iron gate stands open, revealing a pathway lined with autumn leaves and greenery. The archway is adorned with climbing vines, leading into a serene garden filled with various plants and flowers. A soft natural light bathes the scene.
Farm stay in Greve in Chianti
4.98 out of 5 average rating, 59 reviews

Casa Giulia di Sopra Farmhouse

DarioRating, 5 stars3 weeks ago
What a great winery! The location is really unique, the accommodation is in the middle of the vineyard and very quiet. Alessandro our host was very nice, gave us a warm welcome and took a lot of time to show us everything (including the wines). We were also very happy with the accommodation, which was beautifully furnished and had everything we needed.
Top guest favorite
The image features a rustic stone guesthouse with large windows, situated on a lush green lawn. Wooden lounge chairs are positioned outside, inviting relaxation. Surrounding trees and olive groves complement the pastoral landscape, contributing to the serene rural setting.
Cottage in Geggiano
4.99 out of 5 average rating, 133 reviews

Villa di Geggiano – Guesthouse

CharlesRating, 5 stars3 weeks ago
Everything about this place was magical and refined and peaceful. It was like stepping out of time and into a space of beauty and peace. Birds singing, frogs chirping, fire flies lighting up the night. Andrea was so friendly and so helpful and so generous. I definitely want to come back and stay longer. I can even imagine my daughter’s wedding there. We look forward to our next opportunity to stay!
Top guest favorite
A contemporary outdoor patio area features a wooden deck, dining table with several chairs, and an umbrella for shade. Lush green grass surrounds the space, complemented by various plants and shrubs in the background, providing a harmonious connection to nature.
Farm stay in San Quirico d'Orcia
4.98 out of 5 average rating, 44 reviews

Wine Loft in the vineyards

HilaryRating, 5 stars2 weeks ago
The Wine Loft is incredibly peaceful and beautiful. The modern architecture is gorgeous and the views are magical. We traveled by trains and it was easy to take a taxi (arranged by the Wine Loft) from the station. Additionally, we enjoyed walking the country path through the woods and meadow to Bagno Vignoni. We highly recommend this beautiful property. The wines were a phenomenal addition to the stay.

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Province of Siena
  5. San Regolo