
Holiday rentals in Castiglion del Bosco
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Top-rated holiday rentals in Castiglion del Bosco
Guests agree: these stays are highly rated for location, cleanliness and more.
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Top guest favourite

Farm stay in San Quirico d'Orcia
4.99 out of 5 average rating, 83 reviewsPodere Pereti Nuovi-modern Tuscan Villa
MichaelRating, 5 stars5 days ago
Fabulous. Spectacular. Breath taking. Phenomenal. Not sure what other superlatives I can use. Incredible stay at an incredible property with an incredible host in an incredible location. We will be back. Eight of us staying in this beautiful home. San Quirico d’Orcia is an absolute perfect place to stay in Tuscany if you are planning to go to the hill towns. Can’t recommend enough.
Guest favourite

Home in Castelmuzio
4.93 out of 5 average rating, 42 reviewsCasa Ora d"Oro - Panoramic Views
Jason AllenRating, 5 stars3 weeks ago
first I love his neighbors who checked us in. Cinzia was amazing. She not only showed us our place but took our kids to show us her farm. she also makes her own olive oil and gifted us with some! Wonderful Italian neighbors!! I contacted Rocky in advance and he provided me with specific recommendations for where we should go during a long drive we took. we went where he suggested and was not disappointed! Amazing quiet location with great near by wineries. would 100% recommend to everyone!
Guest favourite

Villa in Buonconvento
4.95 out of 5 average rating, 57 reviewsBellagatta, an Enchanting spot in Val d'Orcia
MartinRating, 5 stars8 months ago
We had an amazing four weeks staying at Bellagatta, using it as a base to explore Tuscany & surrounds, and it met all our expectations and more. Bellagatta is a positioned on a hilltop with stunning 360 degree panoramic views, more beautiful than the photos. The annexe that we stayed in was exceptionally clean and comfortable and well fitted out. Air con was useful on the first few days of our stay which were very hot. The property is well situated, 10 minute drive into Buonconvento (not quite an easy return walk up the hill!) which was convenient for restaurants & shopping. Gaetano was a most delightful host, very welcoming, & always taking interest in which towns we were travelling to and providing useful tips for our visits. His property manager, Susil, was also readily available and looked after us with anything we needed , even providing fresh eggs, vegetables & olive oil from the property. Highly recommended!

Apartment in Sinalunga
5 out of 5 average rating, 4 reviewsThe Secret
JonathanRating, 5 stars2 days ago
We had a wonderful time in this charming accommodation in Tuscany! Everything was just like in the pictures – clean, tastefully furnished and with great attention to 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!
Top guest favourite

Home in Montalcino
5 out of 5 average rating, 8 reviewsNew Palazzo in City Center: 4 King Bedrms 6 Bath
RiteshRating, 5 stars1 month ago
Thank you Brian for sharing your beautiful home with us for a couple of days. Your home is by far the best maintained and most well equipped and pristine places that we have stayed so far. We had the most amazing time in the house as well as walking around the city in the evenings. The location is perfect for everything from shopping to restaurants and wine tastings. Thank you Valentina for taking care of our needs during the stay, we would definitely return to stay at your house the next time when we visit. Thank you so much🙏
Guest favourite

Home in Montalcino
4.88 out of 5 average rating, 8 reviewsNEW Panoramic loft with garden in Montalcino
VicRating, 5 stars2 weeks ago
Tatsiana and Lorenzo’s Airbnb was such a beautiful place to stay. We were deciding between an agriturismo and this private loft, and I’m glad we made the right decision. The tiny home has two floors with ample space for a couple, and was remarkably clean and tidy when we arrived. It was recently renovated so the upstairs bedroom feels very clean and new. If you’re looking specifically for privacy, room to unplug, and some space away from the crowds, I would definitely recommend. We had breakfast outside each morning and packed a picnic one day. During the days and evenings, we were about 30-45min drive from Pienza / Siena which was very manageable. Highly rec Drogheria Locanda only a 10min walk from the loft if looking for some delicious modern and innovative Italian food. The driveway leading up to the loft is quite tight - a smaller car would be recommended to navigate the tight turns. Wish we could stay longer! What a special place

Home in Buonconvento
4.94 out of 5 average rating, 17 reviewsDimora del Vino
LouisRating, 5 stars1 week ago
it was a wonderful place. great views, great amenities, great all round. would give it a 6 out of 5 if it were possible
Guest favourite

Farm stay in Montalcino
4.95 out of 5 average rating, 59 reviewsGinepro Apartment Podere Giardino
DavidRating, 5 stars5 days ago
Daniela and Giuliano's place is really a 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 kittens were the icing on the cake!
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- Santa Maria Novella
- Duomo di Firenze
- Ponte Vecchio
- Lake Trasimeno
- Lake Bolsena
- Feniglia
- Gulf of Baratti
- Basilica of Santa Maria Novella
- Cala Violina
- Fortezza da Basso
- Uffizi Gallery
- Parco delle Cascine
- Piazza della Repubblica
- Piazzale Michelangelo
- Marina di Grosseto beach
- Kite Beach Fiumara
- Mercato Centrale
- Pitti Palace
- Stadio Artemio Franchi
- Giardino Bardini
- Avignonesi Winery Fattoria Le Capezzine
- Medici Chapels
- Cavallino Matto
- Teatro Verdi