
Guesthouse vacation rentals in Province of Siena
Find and book unique guesthouse rentals on Airbnb
Top-rated guesthouses in Province of Siena
Guests agree: these guesthouses are highly rated for location, cleanliness, and more.
0 of 0 items showing
1 of 3 pages
Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Province of Siena guesthouses
Family-friendly guesthouses

Guesthouse in Monte Antico
4.4 out of 5 average rating, 10 reviewsBeautiful Apartment with Pool in Maremma
JessicaRating, 5 stars35 months ago
Beautiful home! The pool and views were incredible. The host was always available and kind in responding to any questions we had. We lived our experience staying here!

Guesthouse in Caldana
4.8 out of 5 average rating, 182 reviewsAppartment 1 surrounded by Tuscan Nature
EsterikaRating, 5 stars3 weeks ago
Had an amazing vacation Dagmar is a wonderful host, her farm is entirely inviting you to enjoy and rest. The scenery is beautiful, the animals are so friendly and good, there is plenty of nature around. In the cabin itself I had everything, comfortable for a short or long stay. Within a short drive there are grocery stores, coffee shops, excellent wineries and restaurants, and approximately 1 hour drive to Siena and other interesting towns in the area. In my eyes the place was perfect, for nature lovers it is an amazing experience highly recommended. I definitely intend to go back

Guesthouse in Montieri
4.9 out of 5 average rating, 20 reviewsPodere Rachele - Ghiandaia House
LoïcRating, 5 stars20 months ago
We had a great time, the setting and location allowed us to gather as a family and enjoy the surroundings without stress. ( no noise, the essentials nearby...) The view is beautiful, the pool is very pleasant. The accommodation is functional and spacious enough. Many thanks to Francesco!!

Guesthouse in Montieri
4.72 out of 5 average rating, 18 reviewsPodere Rachele - Owl's House
ChiRating, 5 stars6 months ago
We stayed at Francesco’s place for two nights. It was raining so we didn’t have the full benefit of the area. He was very helpful with everything. However, there aren’t many amenities so come prepared. It was a very comfortable place.

Guesthouse in Croce
4.85 out of 5 average rating, 62 reviewsSecret Haven
KatoRating, 5 stars7 months ago
It was a great place to stay. Highly recommendable! Close to all kinds of attractions. Hosts are quick to respond and helpful. Pool was great!
Guest favourite

Guesthouse in Antria
4.92 out of 5 average rating, 126 reviewsA charming Tuscan retreat
EricRating, 5 stars6 months ago
Gorgeous stay! Views were stunning and the villa exceeded expectations. This was a perfect place to unwind and relax. Highly recommend.
Superhost

Guesthouse in Castiglione della Pescaia
4.5 out of 5 average rating, 4 reviewsLa Rondine - big windows & pool
NicoleRating, 5 stars6 months ago
We had a great time in this very lovely apartment with a fantastic view! On a rainy day you can cuddle up, have some tea and enjoy the foggy view. The place is great with lots of attention to detail :) The kitchen unit is not shown in the pictures but was good and totally sufficient for some simple cooking👍🏻 We will recommend this airbnb to friends!

Private room in Radda in Chianti
4.81 out of 5 average rating, 159 reviewsDouble room with two beds and a view
EvelynRating, 5 stars7 months ago
We absolutely loved our stay at Romanita’s place. The house was charming, the views were incredible and it was extremely relaxing and peaceful. Meeting Romanita was a highlight - she is so warm and makes you feel like an old friend. We could not communicate well as we don’t speak Italian but through google translate, tone and hand gestures, it felt like we had some beautiful conversations together. We recommend Romanita’s place to stay! It is close to town where we had some meals and we were able to easily park the car nearby.
Guesthouses with a patio
Top guest favourite

Guesthouse in San Gimignano
5 out of 5 average rating, 24 reviewsSan Gimignano Relaxation
CedricRating, 5 stars7 months ago
Very good stay. Very nice location for visiting the area. Excellent communication with Cédric and his mom who always had great advice for visiting the area.
Top guest favourite

Guesthouse in Solaia
4.93 out of 5 average rating, 28 reviewsApartment "Cerbaia" in rural house with pool
MatildaRating, 5 stars7 months ago
What a wonderful time we had here! The place is lovely, especially by the pool it looks just as nice as in the pictures. The hosts were extremely friendly. Unfortunately, we had terrible traffic on the way there and didn't arrive until 10 PM. However, we were able to stay in touch via text the entire time and were warmly welcomed despite the late hour! A few days later, the two of them even gave us a wine because ours was bad. Thanks again! We had a great week and would come back at any time :)
Destinations to explore
- Castle rentals Province of Siena
- Condo rentals Province of Siena
- Apartment rentals Province of Siena
- Tiny house rentals Province of Siena
- Townhouse rentals Province of Siena
- House rentals Province of Siena
- Farmstay rentals Province of Siena
- Family-friendly rentals Province of Siena
- Smoking-friendly rentals Province of Siena
- Rentals with breakfast Province of Siena
- Rentals with pools Province of Siena
- Kid-friendly rentals Province of Siena
- Barn rentals Province of Siena
- Rentals with a washer and dryer Province of Siena
- Loft rentals Province of Siena
- Bed and breakfasts Province of Siena
- Villa rentals Province of Siena
- Fitness-friendly rentals Province of Siena
- Vacation home rentals Province of Siena
- Rentals with a patio Province of Siena
- Rentals with a sauna Province of Siena
- Rentals with a kayak Province of Siena
- Rentals with a fireplace Province of Siena
- Rentals with lake access Province of Siena
- Rentals with a balcony Province of Siena
- Rentals with an EV charger Province of Siena
- Luxury rentals Province of Siena
- Rentals with a hot tub Province of Siena
- Serviced apartment rentals Province of Siena
- Rentals with a firepit Province of Siena
- Rentals with outdoor seating Province of Siena
- Cottage rentals Province of Siena
- Nature eco lodge rentals Province of Siena
- Rentals with an accessible height bed Province of Siena
- Private suite rentals Province of Siena
- Pet-friendly rentals Province of Siena
- Waterfront rentals Province of Siena
- Hotel rentals Province of Siena
- Boutique hotel rentals Province of Siena
- Guesthouse rentals Tuscany
- Guesthouse rentals Italy
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Santa Maria Novella
- Duomo di Firenze
- Ponte Vecchio
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Mugello Circuit
- Basilica of Santa Maria Novella
- Fortezza da Basso
- CavallinoMatto
- Uffizi Gallery
- Piazzale Michelangelo
- Parco delle Cascine
- Stadio Artemio Franchi
- Marina di Grosseto beach
- Mercato Centrale
- Piazza della Repubblica
- The Boboli Gardens
- Teatro Verdi
- Pitti Palace
- Basilica di Santa Croce
- Santa Maria della Scala
- Avignonesi Winery Fattoria Le Capezzine
- Teatro Tuscanyhall
- Palazzo Vecchio
- Kite Beach Fiumara
- Things to do Province of Siena
- Sightseeing Province of Siena
- Tours Province of Siena
- Art and culture Province of Siena
- Food and drink Province of Siena
- Nature and outdoors Province of Siena
- Sports activities Province of Siena
- Things to do Tuscany
- Art and culture Tuscany
- Nature and outdoors Tuscany
- Wellness Tuscany
- Entertainment Tuscany
- Sightseeing Tuscany
- Tours Tuscany
- Sports activities Tuscany
- Food and drink Tuscany
- Things to do Italy
- Food and drink Italy
- Tours Italy
- Sports activities Italy
- Sightseeing Italy
- Nature and outdoors Italy
- Wellness Italy
- Art and culture Italy
- Entertainment Italy