Boutique hotel vacation rentals in Province of Siena

Find and book unique boutique hotels on Airbnb

Top-rated boutique hotels in Province of Siena

Guests agree: these boutique hotel rentals are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Guest favourite

Boutique hotel in Panzano In Chianti

5.0 out of 5 average rating, 31 reviews

Villa La Petraia Elysian

Villa La Petraia is an ancient villa located within the historic centre, and was at the time, the first and only restaurant on the ancient route of the medieval road connecting Florence to Siena. With 5 rooms, individually furnished with antique elements combined with modern design without sacrificing a comfortable and luxurious atmosphere. With a large two-level garden and a swimming pool with breathtaking views, La Petraia is a magical place to experience the heart of Chianti.

Nov. 26 – Dec. 3

$368 CAD per night

Guest favourite

Boutique hotel in San Gimignano, Siena

5.0 out of 5 average rating, 32 reviews

Boutique Hotel in San Gimignano

Il nostro boutique hotel è nel mezzo di un ampio giardino mediterraneo con piscina. Facendo colazione sulla terrazza si può ammirare l'alba e il bellissimo panorama delle colline toscane. Siamo a 4 km dal bellissimo paese medievale di San Gimignano La piscina è aperta da aprile ad ottobre e non è riscaldata. Per ogni camera sono disponibili 2 lettini e 1 ombrellone. Il nostro parcheggio privato è a disposizione dei clienti gratuitamente.

Jan. 9 – 16

$203 CAD per night

Superhost

Boutique hotel in Roccalbegna

Albergo La Pietra - Classic

Albergo La Pietra, located in Roccalbegna, in the province of Grosseto, formerly known as Antica Locanda La Pietra, was founded in 1821 as the main and only inn in Roccalbegna. In 2021 it was extensively renovated by the current owner, Monica Patiño. As of April 1, 2023, the Davide Lazzaretti Community Cooperative opened the doors of the inn, offering 6 rooms with bed & breakfast and half board services. The price includes breakfast.

Mar. 30 – Apr. 6

$165 CAD per night

Guest favourite

Boutique hotel in Siena

4.98 out of 5 average rating, 59 reviews

Sleeping on Siena roof

Francesca welcomes her guests in the Residenza d'Epoca with its original charm the rooms are furnished with unique and vintage pieces, an ideal place for contemporary travellers in search of spontaneity. You can enjoy a fantastic breakfast served in your room at the price of 12,00 Euro per person to be paid at the property. For any information do not hesitate to contact the host. Enjoy your travel experience with Airbnb!

Jul. 31 – Aug. 7

$265 CAD per night

Guest favourite

Boutique hotel in Campagnatico

4.93 out of 5 average rating, 15 reviews

Deluxe Independent Room with Panoramic View

Fall asleep with all the stars of the world. Stay in a deluxe room with a king-size bed. Decorated with modern design but maintaining the characteristics of the context intact. Located on the first and last floor, it is served by an elevator, as well as by a staircase. Parquet, air conditioning, WiFi, satellite TV, private bathroom, electronic lock, safe, refrigerator.

Jan. 20 – 27

$137 CAD per night

Guest favourite

Boutique hotel in Siena

5.0 out of 5 average rating, 13 reviews

Suite Pandolfo Petrucci

La nostra Residenza d'epoca si trova proprio nel cuore della città, proprio di fronte al Battistero di Siena. Si tratta di un edificio storico dove ogni ospite può respirare la storia di questa città, un vero e porprio mini museo dove hanno soggiornato illustri personaggi come ad esempio Le Courbusier, Louis Khan, papa Alessandro VIi e Francesco di Giorgio Martini

Feb. 16 – 23

$289 CAD per night

Boutique hotel in Strove

4.72 out of 5 average rating, 57 reviews

Room with private bathroom and breakfast

Casalta Boutique Hotel is located in the heart of Strove, in the hamlet of Monteriggioni, a small village of Lombard origins, along the Via Francigena. All rooms are furnished with antique furniture and objects, expertly preserved and enhanced. In the morning a rich breakfast with home-made and fresh products will be served (included in the rate).

Jul. 9 – 16

$128 CAD per night

Guest favourite

Boutique hotel in Civitella In Val di Chiana

4.89 out of 5 average rating, 18 reviews

Romantic Living!

Large bedroom with views of the Chiana Valley, bright and comfortable has en-suite bathrooms, complimentary hairdryer kits included. Located on the first floor of an ancient building, accessible by a flight of stairs, it does not have a descender. In the historic centre of Civitella in Val di Chiana, in the charming Piazza Lazzeri.

Apr. 23 – 30

$127 CAD per night

Superhost

Hotel room in San Gimignano

4.74 out of 5 average rating, 19 reviews

San Gimignano Easy

Rooms are genuine in their simplicity and comfort in keeping with the fundamental L’Antico Pozzo style. They are perfectly suited for the essential holiday without sacrificing the quality and full service of our modern 3 star hotel. -> The room can have a double bed or 2 separate beds, please reconfirm at the time of booking.

Dec. 1 – 8

$154 CAD per night

Guest favourite

Boutique hotel in Piancastagnaio

4.93 out of 5 average rating, 28 reviews

Camera Antica Foresteria

A privileged room overlooking the Friars' Garden, from which you can see the top of Mount Amiata, ideal for those who go on vacation with their dog. The rooms are spacious and cool. Waking up in the morning and enjoying the views of the lush garden of flowers and fruits is a true privilege.

Apr. 3 – 10

$232 CAD per night

Guest favourite

Hotel room in Siena

4.88 out of 5 average rating, 146 reviews

Charming Room one step from Duomo 3

The Property Quattro Cantoni is located in the heart of the historic center of Siena, in front of the National Art Gallery and a short walk from the Duomo. It 'consists of four elegant rooms with private bathroom, equipped with every comfort.

Mar. 30 – Apr. 6

$173 CAD per night