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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.
Hotel room in Siena
4.84 out of 5 average rating, 56 reviews

Double Classic room Duomo

benoitRating, 5 stars3 months ago
Very good stay with Dominico. Great place to visit Siena.
Top guest favorite
Private room in Montepulciano
4.92 out of 5 average rating, 39 reviews

Bedroom w/Swimming Pool in Tuscany - Montepulciano

EmmaRating, 5 stars5 days ago
The most amazing stay! You won’t regret it! 5 min drive from Montepulciano and a great location to explore Pienza and hop over to Umbria. Fav park was sitting outside drinking wine from their vineyard. HIGHLY recommend staying here. Everything was clean and instructions were clear. We met Alex and his mom they were wonderful. Take a walk around the property too! We wish we could stay longer! Great water pressure, comfy bed and wine glasses :) The AC was also nice. Grazi Alex!
Superhost
Hotel room in San Quirico
4.81 out of 5 average rating, 96 reviews

Flat in Val d'Orcia

ClémentRating, 5 stars3 weeks ago
The place is very quiet and has a great view. However, you must count 15/20 minutes of gravel road to reach San Quirico (the nearest village). Paolo provided us with a lot of information about the area as well as the cities he advised us to visit depending on how long we stayed. The accommodation allows you to stay longer thanks to the kitchen and outdoor BBQ (in addition to the activities available: swimming pool, ping pong, petanque etc). Small clarification: plan to pay the tourist tax in cash (about €2/day/person).
Guest favorite
Hotel room in Barberino Val d'Elsa
4.98 out of 5 average rating, 100 reviews

Room in the Argenna Mill, Chianti, Tuscany

MichaelRating, 5 stars1 week ago
Fantastic place, with beautiful quiet surroundings. Thank you so much for a wonderful stay - it was exactly what we needed. Peace, beautiful nature and natural sounds. And how lucky you are to be allowed to live right next to a babbling brook! We felt both warmly received and very welcome. Thank you for letting us visit the winery – it was a great experience. The pool was lovely, and breakfast was a highlight every day with new, delicious cakes. The location is also absolutely perfect – peaceful, but still close to everything. We would recommend the place to others without hesitation ❤️ Sincerely, Birgitte and Michael 😍
Hotel room in Panzano
4.88 out of 5 average rating, 107 reviews

Chianti Red 1

ValRating, 5 stars12 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
Hotel room in Siena
4.71 out of 5 average rating, 80 reviews

B&BP in Ancient Fortress in organic farmSiena10min

CarolineRating, 5 stars10 months ago
The accommodation and its surroundings are even more beautiful and pleasant than in the listing photos, we had a great time, always well supported and advised by Bice. (@ Bice, we couldn't say goodbye to Yolenda when we left, can you pass her our regards, please? Thank you) Caroline and Sandrine
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 stars37 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 stars1 month 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 stars84 months ago
Beautiful setting, very quiet location, wonderful quiet pool. Very quaint and a great respite from the crowds.
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!
Private room in Massa Marittima

Triple room with terrace Massa Marittima

KilianRating, 5 stars11 months ago
The stay was wonderful. I would like to highlight the friendliness of the service staff. It's a fun vacation!
Hotel room in Montepulciano
4.9 out of 5 average rating, 21 reviews

Junior Suite Sophia - Beautiful Tuscany

BenRating, 5 stars35 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 stars3 weeks 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

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