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Hotel holiday rentals in Siena

Find and book unique hotels on Airbnb

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Family-Friendly hotels

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.
Superhost
Hotel room in Gavinana
4.73 out of 5 average rating, 40 reviews

B&B mòsì -ROOM E- DOUBLE ROOM WITH TERRACE

JakobRating, 5 stars14 months ago
Wonderful apartment with a beautiful backyard in a quiet area, still close to the city center.
Top Guest favourite
Private room in Montepulciano
4.92 out of 5 average rating, 39 reviews

Bedroom w/Swimming Pool in Tuscany - Montepulciano

EmmaRating, 5 stars6 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!
Guest favourite
Hotel room in Gambassi Terme
4.93 out of 5 average rating, 27 reviews

Tenuta Quadrifoglio - Bedroom 3 Iris

SamanthaRating, 5 stars2 weeks ago
We had an amazing time at this hotel! The views and grounds are absolutely stunning! Gorgeous view of the Tuscan hills from your window and all around! The staff are super friendly and we’re so kind! There was a wedding on the property the first night we were there, and the staff notified us in advance and offered to upgrade us or comp our breakfast. We went with breakfast, and it was a delicious spread! Plenty of food and drink options. Dinner at their own restaurant was exceptional! And they had the best hot chocolate I’ve ever had! The location is so close to local towns, we visited 3 in a one day drive (Pisa, Volterra and San Gimignano). Pisa was the most far away but just 1 hour to get there. Overall, you can’t beat the incredible views and amazing service here! Do yourself a favor and book it and get ready for a relaxing and beautiful stay!
Guest favourite
Hotel room in Radda in Chianti
4.9 out of 5 average rating, 119 reviews

Chianti Apartment - 5/6 People

TheRating, 5 stars2 weeks ago
Words cannot even describe how perfect this was for us. Two adults and two teenagers. Plenty of room. A perfect place for our Tuscany get away.
Guest favourite
Hotel room in Centro Storico
4.93 out of 5 average rating, 30 reviews

B&B Casa Tintori - Yellow Room

AllisonRating, 5 stars2 months ago
This is a true gem! I almost didn't write this review because I don't want to let this secret hideaway become overcrowded and unable to book when I go back to Florence. An authentic Florentine bed and breakfast, centrally located, safe, clean, and the best part are the hosts that treat you like family! Breakfast and coffee-phenomenal! Not only are you getting a lovely and quaint place to stay, but you also get the assistance and care from Riccardo and his wife to have the best experience in Florence. Both were so helpful in arranging a tour of the Chianti region, being present for my lost luggage so I didn't worry and waste time waiting for the delivery, making reservations to places I couldn't get into, giving advice for sites to see, even ordering a taxi for departure, and offering historical information about the city and its many changes. They go over and above what is expected from an air bnb! Will definitely stay again if they will have me!
Guest favourite
Hotel room in Montevettolini
4.91 out of 5 average rating, 33 reviews

La Mangiatoia

InaRating, 5 stars2 weeks ago
This is the second time we visit Sabrina's lovely place. Sabrina and the family are always sweet, welcoming and very friendly. The place is so clean and tidy and you feel at home. The pool area is also really nice. If you need peace and quiet and the most beautiful view, then this is the place.
Superhost
Hotel room in Florence
4.74 out of 5 average rating, 241 reviews

On the hill, close to the center

ChristinaRating, 5 stars2 weeks ago
We found a perfect quiet place in close proximity to Florence with a great host Carla. A really nice house from the 15th century (I think) the garden invites you to linger and rest between the sightseeing tours in Tuscany. Over a delicious breakfast, you can chat with the other guests. Really recommended 👍

Hotels with a pool

Guest favourite
Hotel room in San Gimignano
4.97 out of 5 average rating, 61 reviews

Boutique Hotel in San Gimignano

LisaRating, 5 stars2 weeks ago
Our stay was outstanding! We spent 5 nights and would 100% recommend this property to anyone. Lucas and his team at the hotel were exceptional, and we felt like members of the family. Surroundings beautiful with lots to do locally and you can easily drive to Siena or Florence for visits whilst there. Big benefit was the all day/eve snacks, and dinner 3 times a week if you don’t want to drive into town everyday. Fabulous experience, and we will return!
Guest favourite
Hotel room in Sassetta
4.88 out of 5 average rating, 43 reviews

Carlo Sassetta B and B Field, Sassetta

RosarioRating, 5 stars2 weeks ago
We loved our stay , everything was beautiful and just as described, Christine and Monica we’re both great host and made us feel at home. The countryside is beautiful. The recommendation for restaurants were all great, I would definitely go back again !
Guest favourite
Hotel room in Rignano sull'Arno
4.86 out of 5 average rating, 28 reviews

Bedroom in Villa with Pool - Breakfast on request

SergioRating, 5 stars5 months ago
Beautiful place and very welcoming, we had a great time
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 region as well as the cities he advised us to visit depending on the time 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 note: plan to have cash to pay the tourist tax (about €2/day/person).
Top Guest favourite
Private room in San Gimignano
4.96 out of 5 average rating, 83 reviews

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

MarleneRating, 5 stars3 weeks ago
Villa Baciolo was truly enchanting. The rooms were spacious and beautifully decorated, with fantastic bathrooms and a peaceful, serene atmosphere throughout the property. Sandra, her sister, and their entire family were incredibly kind and always available when needed. The complimentary breakfast each morning was a delight—fresh juice, local fruits, pastries, yogurt, and cereal. In the evenings, we enjoyed drinks from the bar and dinner onsite while taking in the unforgettable view of San Gimignano’s medieval skyline. This place holds a special place in our hearts. My husband and I will never forget the warmth of the people—or their fluffy dog Ada! Highly recommend booking this gem.
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 Villa a Sesta
4.73 out of 5 average rating, 37 reviews

Apartment with large veranda in Chianti

LaurenRating, 5 stars2 weeks ago
We had a fabulous time at Villa Di Sotto! Giulia and her family were incredibly hospitable. We felt so welcomed and adored the property. Would totally stay again!
Hotel room in Trequanda
4.67 out of 5 average rating, 92 reviews

Abbadia Sicille - Junior Suite with sauna

DianaRating, 5 stars9 months ago
The place on the outside definitely looks different (outdated in some parts) from pictures, but they were very welcoming and the area is so peaceful. When we arrived in our room there was a book full of recommendations about things to do and restaurants which was very helpful. The room was very beautiful and spacious. The service was wonderful. We didn’t try the restaurant because we stayed for a short time but hopefully will do that next time :) …

Hotels with a patio

Casa particular in Casciana Terme
4.67 out of 5 average rating, 12 reviews

Tenuta La Casetta Farmhouse - Chianti

KatarzynaRating, 5 stars13 months ago
Beautiful views that make you no longer want to move. Super located, beautiful landscape on every side. The pool is clean and well-maintained. Lots of space for walking, safe for children who ran around the property on their own. Elevations are pleasant, which makes cycling easier. The apartment is clean, fully equipped, and a big plus. Great contact with the owner, she was very helpful, she responded very quickly to any doubts if they appeared, explained right away. I recommend the place! I'll be sure to go back :)
Top Guest favourite
Casa particular in Calenzano
4.99 out of 5 average rating, 141 reviews

[Near Florence] Nautilus loft

EdwinRating, 5 stars4 days ago
The Airbnb was beautiful and very easy to check in. Davide and his co-host was very nice and very informative before we even had arrived. We got both restaurant and café recommendations which was really pleasant. The place was very cool and special, a great experience overall! Would definitely come back if I ever get the chance!
Superhost
Shared room in Centro Storico
4.71 out of 5 average rating, 49 reviews

1 Bed In a 6 Female Ensuite Dorm - YellowSquare

NicolleRating, 5 stars2 months ago
Easy to access location, good and clean rooms, with dryer in the bathroom, hot water, bed well ok. Hostel structure very good. They perform various activities, welcome drink and pasta at night for guests free of charge. It is worth remember: they only provide towel by means of rent.
Guest favourite
Hotel room in Piancastagnaio
5 out of 5 average rating, 20 reviews

Antica Foresteria Room 2

JasminRating, 5 stars8 months ago
This was a wonderful experience. we really recommend it! the place is beautiful, full of history and wonderful hospitality. we'll visit again for sure.
Guest favourite
Hotel room in Guardistallo
5 out of 5 average rating, 10 reviews

Vittoria by Beata Relais

vieriRating, 5 stars4 weeks ago
Thank you for all your support. Always ready and responsive to requests. Really everything perfect thanks V
Guest favourite
Hotel room in Greve in Chianti
4.92 out of 5 average rating, 39 reviews

Villa Gioietta - 2-Bedroom Suite

EmilyRating, 5 stars1 month ago
This home is something special. Very clean. Very aesthetically interesting. The beds were very comfortable. Linens lovely. Everything in the space had a story to tell. Lots of history. Stefano was very flexible and informative. We never met Stefano due to the fact that we came in late from travels and had to leave early for a flight home. But we had all we needed to feel at home when we arrived. Coffee in the AM and wonderful seating areas outside to watch the sunrise and hear the birds:) thank you Stefano for leaving us with a very cozy last night in Tuscany. We will never forget it.
Guest favourite
Hotel room in Centro Storico
4.84 out of 5 average rating, 140 reviews

Ricasoli Boutique 5

MatthewRating, 5 stars1 month ago
Great location, great unit and a great host. I would highly recommend.
Superhost
Resort in Il Castagno
5 out of 5 average rating, 3 reviews

Chianti Resort - Casa Lavanda

AgnieszkaRating, 5 stars21 months ago
When I was watching videos about Tuscany, I dreamed of living in a house like this from a movie… and it worked! It's an amazing home…. There's such a vibe…. Ech…. Additionally a beautiful pool, super location, property on such hectares that ohhhoohooo… service for 6👍 me and my family - we are DELIGHTED and heartily recommend🌸🤗👍

Quick stats about hotel rentals in Siena

  • Total rentals

    20 properties

  • Nightly prices starting at

    $116 NZD before taxes and fees

  • Total number of reviews

    510 reviews

  • Pet-friendly rentals

    10 properties allow pets

  • Wi-Fi availability

    20 properties include access to Wi-Fi

  • Popular amenities

    Kitchen, Wi-Fi and Pool

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Province of Siena
  5. Siena
  6. Hotel rentals