
Guesthouse holiday rentals in Province of Siena
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Top-rated Guesthouses in Province of Siena
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Family-Friendly guesthouses

Guesthouse in Monte Antico
4.4 out of 5 average rating, 10 reviewsBeautiful Apartment with Pool in Maremma
JessicaRating, 5 stars37 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, 184 reviewsAppartment 1 surrounded by Tuscan Nature
RobertRating, 5 stars2 months ago
We can just highly recommend staying and this place. Dagmar is a great host with plenty of usefuly tipps and amazing activities on site. The house is exactly as described and was perfect for the four of us. It is surrounded by pure nature and a lot of animals (dogs, horses, sheeps etc.) which are superfriendly.

Guesthouse in Montieri
4.86 out of 5 average rating, 21 reviewsPodere Rachele - Ghiandaia House
LoïcRating, 5 stars22 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 stars7 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 stars9 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, 130 reviewsA charming Tuscan retreat
janeRating, 5 stars2 weeks ago
A very peaceful retreat in a beautiful garden with lots of private places to sit or eat and an extended view over the valley towards Arezzo and mountains beyond. Caroline was helpful but did not intrude. The cottage has an authentic Tuscan style and furniture to match and although quite dark there are big windows looking out onto the garden and view. We enjoyed using the private pool and exploring the local area as well as a National Park to the north (lovely beech forest) and Siena. The TV isn’t ‘smart’ and there is no dishwasher but this is reflected in the price (however there’s a large book collection including lots of guidebooks). It was a very relaxing stay for us, thank you.
Superhost

Guesthouse in Castiglione della Pescaia
4.5 out of 5 average rating, 4 reviewsLa Rondine - big windows & pool
NicoleRating, 5 stars8 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, 161 reviewsDouble room with two beds and a view
TizianoRating, 5 stars1 month ago
very nice and very nice Romanite
Guesthouses with a patio

Guesthouse in Binami
The Orion Villa
JosephRating, 5 stars1 month ago
Just what our family wanted! Quiet and peaceful with privacy for our group. Valerie was so helpful and gave us some great local places to try. Hope to be back soon!
Top Guest favourite

Guesthouse in San Gimignano
5 out of 5 average rating, 27 reviewsSan Gimignano Relaxation
ElkeRating, 5 stars4 weeks ago
the accommodation is absolutely quiet and in the middle of nowhere. Nevertheless, you have a wonderful view of San Gimignano and can be there in a few minutes. The cottage was away from the main house and was perfect for two single women with two bathrooms and two bedrooms. Cedric is a perfect host, who always responded immediately to our requests. We enjoyed our stay very much and can only recommend the cottage.
Top Guest favourite

Guesthouse in Solaia
4.94 out of 5 average rating, 31 reviewsApartment "Cerbaia" in rural house with pool
ViktoriaRating, 5 stars2 weeks ago
My girlfriend and I were allowed to spend 4 wonderful and relaxing days with Bengt and Katya in Solaia. The apartment is located in a very small and quiet place. It also has a huge outdoor area with a pool, olive trees, vines, lots of flowers, a pizza oven and even a small outdoor gym. So, if you just want to switch off, you're in the right place. You have an incredibly beautiful view of the forests and can perceive nature with all its sounds, as you are far away from all the noise of the city. A car is highly recommended for the area, as unfortunately you cannot get there by train or bus. We are very grateful for the time we were able to spend there and for the loving hospitality. I think we'll come back at some point.
Superhost

Guesthouse in Caldana
Small, charming pool house - country house

Private room in Castellina in Chianti
New place to staynikki’s room
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- Kid-friendly rentals Province of Siena
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- Santa Maria Novella
- Duomo di Firenze
- Ponte Vecchio
- Lake Trasimeno
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Basilica of Santa Maria Novella
- Mugello Circuit
- 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
- Palazzo Vecchio
- Things to do Province of Siena
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