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Guesthouse vacation rentals in Province of Siena
Find and book unique guesthouse rentals on Airbnb
Top-rated guesthouse rentals in Province of Siena
Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.
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Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Province of Siena guesthouse rentals
Family-friendly guest house rentals
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Guest favorite
Guesthouse in Castellina In Chianti
4.88 out of 5 average rating, 17 reviewsLovely barn in a Tuscan winery
![](https://a0.muscache.com/im/pictures/5125547/ac7fb155_original.jpg?im_w=720)
Guesthouse in Caldana
4.74 out of 5 average rating, 72 reviewsCottage in horse farm 20 min sea
![](https://a0.muscache.com/im/pictures/a9d5d2f0-61fa-48a2-b845-46e0f809a997.jpg?im_w=720)
Guesthouse in Malafrasca-San Frustino
5 out of 5 average rating, 11 reviewsSan Frustino - "Cipressi" Apartment
![](https://a0.muscache.com/im/pictures/miso/Hosting-4562785/original/88319d69-a86b-41b8-8628-df53cf0dc662.jpeg?im_w=720)
Guesthouse in Monte Antico, Grosseto
4.4 out of 5 average rating, 10 reviewsBeautiful Apartment with Pool in Maremma
![](https://a0.muscache.com/im/pictures/4c5de829-67b2-49b6-8ac8-6edc3ab081ff.jpg?im_w=720)
Guesthouse in Pievasciata
small magic cottage on hillside in Chianti
![](https://a0.muscache.com/im/pictures/miso/Hosting-25108129/original/748f0873-b3d5-44b6-b803-51ab80256259.jpeg?im_w=720)
Guesthouse in Giuncarico
4.33 out of 5 average rating, 6 reviewsApartment near the sea Castiglione della Pescaia
![](https://a0.muscache.com/im/pictures/8b28d52e-71f6-4b49-a247-d543def5467c.jpg?im_w=720)
Guesthouse in Boccheggiano
Casa Fabiano
![](https://a0.muscache.com/im/pictures/5a45eb7c-40ef-4023-a929-bb552663fdb7.jpg?im_w=720)
Guest favorite
Private room in Siena
4.9 out of 5 average rating, 123 reviewsSimo&Frank Vacation in Siena
Guest house rentals with a patio
![](https://a0.muscache.com/im/pictures/c53ec489-0feb-4d46-8ede-724e4ac80aa2.jpg?im_w=720)
Guesthouse in Chiusi
5 out of 5 average rating, 4 reviewsCasetta del Nonno
![](https://a0.muscache.com/im/pictures/miso/Hosting-1338372/original/572d34dd-ee5e-4429-8862-3fa4df1e9e36.jpeg?im_w=720)
Guest favorite
Guesthouse in San Gimignano
5 out of 5 average rating, 15 reviewsSan Gimignano Relax
![](https://a0.muscache.com/im/pictures/miso/Hosting-1115723356844767456/original/8e9029f8-39f1-4120-b0ed-e324dae701a4.jpeg?im_w=720)
Guesthouse in Pieve Vecchia
Romantic Tuscan Villa with Pool
![](https://a0.muscache.com/im/pictures/miso/Hosting-689708824242405019/original/20bec262-558c-4306-8399-24217c25c51f.jpeg?im_w=720)
Guesthouse in San Gimignano
Charming, Rustic Barn in Tuscan Countryside
![](https://a0.muscache.com/im/pictures/miso/Hosting-1106617120679356003/original/2a260af1-2afe-4068-b30f-d3c87879d8c1.jpeg?im_w=720)
Private room in Campagnatico
Apt 2
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