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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
A panoramic view reveals rolling hills adorned with vineyards and olive groves, stretching under a dramatic sky. The tan-coloured buildings of the property are nestled among lush greenery, while a serene pool reflects the surrounding landscape.
Apartment in Quercegrossa
5 out of 5 average rating, 9 reviews

Tuscany gem: The Chianti Farmer's House

NickRating, 5 stars1 day ago
A wonderful space - just tucked away from town but easy to get in. Beautiful spaces and very welcoming hosts. We had a wonderful time!
A rustic stone house is framed by lush greenery and trees, creating a serene natural ambiance. Sunlight casts gentle shadows on the facade, highlighting the textures of the stone. A small outdoor table is visible in front of the house, surrounded by manicured grass.
Apartment in Galenda
5 out of 5 average rating, 3 reviews

Apartment Lippi

FrancescaRating, 5 stars3 weeks ago
Great little apartment, very quiet
Guest favorite
Apartment in Bossi
4.9 out of 5 average rating, 59 reviews

Villino Ersilia, the charm of Chianti

LamaRating, 5 stars1 week ago
Peaceful and beautiful place! Gorgeous scenery! Just what we were looking for. We very much enjoyed being able to cook and spend time relaxing at home, but also easily drive around and explore the surrounding areas. Thanks Mattia for sharing your home with us!
A modern stone cottage is situated on a hilltop, surrounded by lush greenery and overlooking a serene landscape. The soft hues of twilight fill the sky, while a private pool is visible nearby. The property is enclosed by a fence, providing a sense of privacy.
Home in Rosennano
4.64 out of 5 average rating, 11 reviews

Dolcevista Cottage

ErinRating, 5 stars1 week ago
What an absolutely perfect place! Myself and my partner stayed here for 4 nights during our Italian road trip and it was hands down the best place we stayed. Just the view from the garden alone is a reason for us to return! Absolutely beautifully decorated and the communication from the host was amazing. We will definitely be returning!
A brick arch frames a lush green garden featuring a large tree and tall cypress trees in the background. A gravel pathway leads towards a rustic building, creating a serene view of the surrounding Tuscan countryside under a clear blue sky.
Condo in Sinalunga
5 out of 5 average rating, 4 reviews

The Secret

JonathanRating, 5 stars1 day ago
We had a wonderful time in this charming accommodation in Tuscany! Everything was just like in the pictures – clean, tastefully furnished and with a lot of love for detail. The host and his wife were incredibly friendly and helpful, which made our stay even more enjoyable. We felt completely comfortable and can wholeheartedly recommend this place!
Guest favorite
A stunning view from a hillside captures a serene pool area at sunset. The scene is filled with vibrant colors in the sky, with lounge chairs arranged beside a sparkling pool. Trees and distant hills are visible in the background, adding depth to the landscape.
Hotel room in Castelfranco di sopra
4.89 out of 5 average rating, 163 reviews

Romantic Medieval Village with pool

OguRating, 5 stars1 week ago
We had a great stay and the host Oscar and crew were very friendly and helpful. You can really relax at this place, the atmosphere was very nice and cozy. The service was very good, when we arrived the kitchen was closed but we still got lunch. Furthermore this place is an oasis of peace with a beautiful view. If you are looking for quiet place, then this is the spot.
Guest favorite
Aerial view of a Tuscan agriturismo set amidst lush greenery, featuring a well-maintained garden with tall cypress trees and a sparkling blue pool. The serene landscape of rolling hills stretches into the distance, framed by vibrant fields and a calm pond.
Private room in Buonconvento
4.93 out of 5 average rating, 120 reviews

"Querce Room" Agriturismo Quarantallina

EliciaRating, 5 stars1 week ago
This is a BEAUTIFUL place located in the rolling hills of Tuscany. Everything was great - the room, the check in experience, the pool, the breakfast (which is included in the price of the room!) Our room was gorgeous, super clean with plenty of towels and storage, efficient air con and a comfy bed. There is also a small fridge in the room so you’re able to keep drinks and food cold. On the grounds there is plenty of seating including a bar area, hammocks and more so you’re not short of places to sit, relax and take in the lovely views. Pool was also lovely and quiet. I will say it’s pretty much a must to have/hire a car to get here as you’re driving on gravel tracks for about 15 minutes to get here. This also means that you’re a bit out of the way from supermarkets etc so keep this in mind when planning on when/if you bring food and drink there. Also if you love animals that’s a plus because there were 3 dogs, 2 cats, 2 donkeys and a horse roaming the grounds. Thank you!
Guest favorite
A stone farmhouse is set against a clear blue sky, surrounded by green olive trees and lush gardens. A wooden door is featured at the entrance, complemented by terracotta roof tiles that reflect natural tones. Scenic hills are visible in the distance.
Farm stay in Montalcino
4.95 out of 5 average rating, 59 reviews

Ginepro Apartment Podere Giardino

DavidRating, 5 stars4 days ago
Daniela and Giuliano's stay is a real gem! The room is compact, with a small bathroom and kitchen, but perfect for two people. The view from the room is truly beautiful. Outside, you can sit in the sun or shade, with the same view over the Tuscan hills. The swimming pool is wonderfully quiet and offers a nice place to relax. Daniela and Giuliano are fantastic hosts. They are happy to help you with everything and run their own small vineyard. The wine tasting with them is an absolute must! And the sweet cats were the cherry on top!

Destinations to explore

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