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Hotel vacation rentals in Province of Siena

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Popular amenities for Province of Siena hotel rentals

Family-friendly hotel rentals

Superhost
Hotel room in Pilli
5 out of 5 average rating, 3 reviews

Elegant suite with breakfast.

SeherRating, 5 stars24 months ago
We loved our stay. Pierre was so attentive and the place was immaculate. Plus the breakfast was absolutely amazing.
Guest favorite
Hotel room in Bettolle
4.92 out of 5 average rating, 48 reviews

Suite in villa Garibaldi Red

ZhuoqiRating, 5 stars2 months ago
Very good host, gave us a very memorable experience!Very attentive, very friendly, we love itđź’•
Superhost
Hotel room in San Quirico
4.81 out of 5 average rating, 94 reviews

Flat in Val d'Orcia

SaraRating, 5 stars6 months ago
Great stay at Tigliolo...the apartment was very comfortable and equipped, a great place to spend a relaxing holiday in the middle of nature.
Guest favorite
Hotel room in Gambassi Terme
4.92 out of 5 average rating, 25 reviews

Tenuta Quadrifoglio - Bedroom 3 Iris

AndrewRating, 5 stars2 weeks ago
The staff was incredibly friendly throughout the duration of our stay! We enjoyed breakfast one morning and wine one afternoon in the gorgeous grounds. Between the pool and various seating areas, there are many places to sit, lounge, relax and take it the breeze and wonderful sights! The room was exactly as described and we were very happy with our stay! Thank You all again!
Guest favorite
Hotel room in Barberino Val d'Elsa
4.98 out of 5 average rating, 97 reviews

Room in the Argenna Mill, Chianti, Tuscany

AriRating, 5 stars2 weeks ago
Hands down, our favorite place we’ve stayed in during our 2 weeks in Italy! Elisa and Alessandro’s hospitality was unmatched. They are amazing hosts and their property was absolutely stunning. Elisa and Alessandro were very friendly, attentive, and caring. They welcomed us with wine and snacks and had great recommendations. They noticed it was my husband’s birthday so they hung a birthday banner up for him before breakfast and set out a candle, the sweetest gesture! The room we stayed in was beautifully designed and very clean, so was the library (breakfast area). I couldn’t stop admiring their beautiful place! They also have a dog and 2 cats on their property, we fell in love with them! They were the perfect addition to our stay. We’ll be recommending their place to our friends and family and will 100% be back during our next trip! Thank you Elisa and Alessandro!
Hotel room in Panzano
4.88 out of 5 average rating, 107 reviews

Chianti Red 1

ValRating, 5 stars11 months ago
Our stay with Marina at Rosso del Chianti was fantastic. Her home and the town were both quaint & beautiful. When we come back to Panzano, we'll stay with Marina again.
Top guest favorite
Private room in Montepulciano
4.96 out of 5 average rating, 53 reviews

Charming room with pool

RebeccaRating, 5 stars3 weeks ago
Alex was an exceptional host—welcoming, attentive, and friendly. His property is beautifully maintained, and the room was clean, spacious, and thoughtfully presented. We thoroughly enjoyed our stay and would highly recommend it to others. The pool, with its stunning view, was a delightful bonus, especially during the warmer months.
Superhost
Hotel room in Province of Siena
4.83 out of 5 average rating, 12 reviews

San Giovan d'Asso - Apartment in Val d'Orcia

ValentinaRating, 5 stars36 months ago
After a dirt road you reach the farm: the place is charming, immersed in the Tuscan hills and nature; the accommodation is very nice, it retains the original spirit of the place... to finish the pool complete everything, for a refresh especially on the hottest days!

Hotel rentals with a pool

Guest favorite
Hotel room in Bettolle
4.92 out of 5 average rating, 24 reviews

Villa Vignacce - apartment Giardino

AlexRating, 5 stars1 month ago
Beautiful and peaceful. The villa had everything you needed for a quite getaway. The village was nice and had good spots to eat. Perfect
Hotel room in Montepulciano
4.45 out of 5 average rating, 121 reviews

Albergo Ristorante San Biagio_Montepulciano(Siena)

DávidRating, 5 stars3 weeks ago
A good place to stay!
Hotel room in San Gimignano
4.57 out of 5 average rating, 7 reviews

San Gimignano countryside BB Superior room

ToddRating, 5 stars83 months ago
Beautiful setting, very quiet location, wonderful quiet pool. Very quaint and a great respite from the crowds.
Top guest favorite
Private room in San Gimignano
4.96 out of 5 average rating, 82 reviews

B&B Villa Baciolo-Room with Breakfast (2)

MassimoRating, 5 stars2 weeks ago
Better than the photos. This place is perfectly positioned away from busy S Geminiano but only 4kms away. Everything was perfect but the thing that stood out the most was Nadia’s and Sandra’s willingness to please our every need. Let’s not forget Ada, the black bundle of joy that welcomed us every day. We highly recommend Villa Baciolo. Thank you ragazze Baci
Superhost
Hotel room in San Gimignano

Tenuta Sovestro Luxe Room with Breakfast

StephanieRating, 5 stars11 months ago
We’ve stayed in numerous places all over the world and this room by far exceeded our expectations! It’s a very big room with a beautiful clean bathroom - the shower is everything! Super comfortable bed, air conditioning functioning, even a complimentary bottle of wine at check in. We loved this place! We were also able to use the Swimmingpools and the breakfast in the restaurant was absolutely next level!!! We also had dinner on both nights and it was spectacular! We did not want to leave! Everyone was also extremely friendly and helpful. If you can I would highly recommend staying here- there is also a short walk up to San Gimignano which is an added bonus!
Hotel room in Sant'Albino

Taddeo di Bartolo Double

IviRating, 5 stars11 months ago
The place is incredible and has a beautiful pool. Wine and food is exceptional. Breakfast from the Chef Albi was incredible. He is also an amazing host who is responsible and very helpful! Totally recommend!
Hotel room in Montepulciano
4.9 out of 5 average rating, 21 reviews

Junior Suite Sophia - Beautiful Tuscany

BenRating, 5 stars34 months ago
Absolute paradise. Don’t hesitate - book it. We could have spent every moment of every day on the grounds enjoying the pool, but would have to wonder into town for lunches. Karin and Antonio have curated the most peaceful getaway. Their staff are extremely kind and friendly. My favourite moment was enjoying my coffee every morning over looking the Tuscan hills. I hope one day we can return. This was the perfect baby moon for us!
Hotel room in San Gimignano
4.85 out of 5 average rating, 27 reviews

BB Ponte Nappo Country S Gimignano

DaveRating, 5 stars1 week ago
BEAUTIFUL property and kind people. The food was great and San Gimigano is just an incredible picture perfect town. The B&B has great food and a very friendly cat, Clara, who loves the company of humans. There’s a 15 minute picturesque walk into town and at night there were HUNDREDS of fireflies to enjoy. Highly recommend

Hotel rentals with a patio

Hotel room in Chianciano Terme
4.5 out of 5 average rating, 42 reviews

Hotel Villa Marina Double Room with View

PaulinaRating, 5 stars2 weeks ago
Recommended, the room is very clean, the view is beautiful and the Full breakfast.
Superhost
Resort in Montepulciano
5 out of 5 average rating, 3 reviews

Agriturismo Merigge with swimming pool

GeorgeRating, 5 stars9 months ago
Had a great stay thanks to Raffaele’s wonderful place and customer service. Definitely recommend and would look to re-visit. The pool is amazingly clean and the salt water was very pleasant in the summer weather. Raffaele’s agriturismo is perfect for a Tuscan country side stay. Thank you Raffaele.
Hotel room in Gaiole in Chianti

Borgo Le Noci Classic

MartinaRating, 5 stars9 months ago
Very pleasant experience, we will definitely be back
Resort in San Donato
4.57 out of 5 average rating, 14 reviews

La Papessa Agritourism - Robinia Ap. 10

KendraRating, 5 stars1 month ago
Lovely stay. Great to be able to walk to the village. Great wine tasting and added bonus that you get a discount as a guest.
Hotel room in Siena
4.68 out of 5 average rating, 19 reviews

Hotel Porta Romana - Standard Room with Patio

SimoneRating, 5 stars4 months ago
Great place outside the center but very close on foot, the view is crazy
Hotel room in Roccalbegna

Albergo La Pietra - Basic

Hotel room in San Gimignano

Boutique Hotel in San Gimignano

Hotel room in Civitella In Val di Chiana

Clarissa - Suite Classic

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