Boutique hotel vacation rentals in Province of Siena

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Top-rated boutique hotel rentals in Province of Siena

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Top guest favorite

A comfortable seating area features a white sofa adorned with decorative cushions, positioned by large glass windows. An elegant wooden table complements the space, while natural light pours in, illuminating the room. Outside, a stone pathway and greenery are visible, enhancing the inviting atmosphere.

Hotel room in Panzano

5 out of 5 average rating, 14 reviews

Villa La Petraia Suite Anam Cara

MelisaRating, 5 stars7 months ago

Christine was the most amazing host!! I was blown away by every single detail at this property. Not only was it extremely clean I had everything I needed at my fingertips. It is absolutely absolutely stunning. The rooms are beautiful and the breakfast is delicious. You can tell there is so much thought and care put into taking care of this property. Christine had offered some local recommendations for wine tours and restaurants which all were amazing. I highly recommend this as a top stay!! If I could, I would give it 10 stars. I almost don’t want to share this good review because I don’t want the secret to get out. Thank you for an amazing stay and opening your home to us. 💗

Aerial view of the organic farm showcases a large outdoor pool surrounded by well-maintained grass, a wooden pergola, and lush vineyards. The farmhouse, with a rustic stone exterior, is nestled in a vast valley, bordered by rolling green hills and distant trees.

Hotel room in Torrita di Siena

5 out of 5 average rating, 5 reviews

Follonico - Standard Room Montefollonico

AngieRating, 5 stars67 months ago

Let your soul dangle and enjoy the toskana landscape from the best side. 360degrees panorama in the middle of the wineyards. You have the feeling you are part of the picture postcard. Warm hosts, perfect spot with love for antique things, you feel like in a museum with instagram scenary everywere. Authentic Toskana Design with a touch of bohemian chic. Wonderful organic breakfast from the garden and their small farm. perfect tips for daytrips, car needed. Besides the doubleroom, Follonico provides also 4 suites which are amazing. We would recommend a minimum of 3 nights to enjoy and feel this place. We highly recommend and appreciate.

Top guest favorite

The exterior of the hotel showcases a rustic building with terracotta roof tiles and a staircase leading to the entrance. Surrounding greenery and a landscaped garden are visible, complemented by a glass-enclosed veranda and vibrant flowers in the foreground.

Hotel room in San Gimignano

4.96 out of 5 average rating, 51 reviews

Boutique Hotel in San Gimignano

DaveRating, 5 stars6 months ago

We were scheduled to stay at Luca's for 2 nights in Oct. The day prior saw an unprecedented rain/thunder/wind story across the Tuscany region and Luca's home was impacted by an overflowing river. We could tell the place was beautiful and were very disappointed we could not stay there due to power/services impact. Luca and his family were very busy trying to restore/clear the grounds when we arrived. The best part was Luca had already made arrangements at a local hotel for us, to not impact us with the stress of finding last minute accommodations. Luca arranged all payment terms with the hotel and all we had to do was show up and enjoy. A true testament to his focus on his customers. We'll be back to try Luca's place in the future.

Guest favorite

An airy room is defined by tall windows, allowing natural light to fill the space. A rustic wooden chest sits on the floor, accompanied by a white chair and desk, enhancing the cozy atmosphere. The ceiling features exposed beams, and scenic rooftop views are visible through the glass.

Hotel room in Siena

4.97 out of 5 average rating, 128 reviews

Sleeping on Siena roof

JoRating, 5 stars2 weeks ago

My husband and I had a lovely stay in Siena. The accommodation was just as described and perfect for our needs. Our only problem was we didn’t have enough time to stay another night. The location was ideal, close to absolutely everything. We would definitely stay again. Francesca was extremely responsive and allowed us to check in a little earlier.

Guest favorite

An aerial view captures the medieval village of Campagnatico, nestled among rolling green hills and trees. The stone buildings exhibit rustic architecture, with a prominent clock tower and terracotta roofs dotting the landscape. A winding road leads through the village, outlining its charming layout.

Hotel room in Campagnatico

4.95 out of 5 average rating, 20 reviews

Camera Indipendente Deluxe con vista Panoramica

SilviaRating, 5 stars5 months ago

In un weekend in moto, di passaggio in zona abbiamo soggiornato nella meravigliosa guest house di Servilio. Il paese di Campagnatico è un piccolo gioiellino che vale la pena visitare, perdendosi per le stradine alla scoperta della cisterna, della fonte, della meridiana e dei passi di Dante Alighieri. La camera di Servilio, la sua casa e la sua ospitalità valgono da soli il viaggio. La camera ristrutturata e arredata con molto gusto, ha una bellissima vista sulla campagna circostante e su una parte del paese, ha tutto quello che occorre per rilassarsi: letto king size comodissimo, aria condizionata , frigo, tv, bollitore. Il bagno è enorme, con bella finestra con vista e ampia doccia walk in . L’host ci ha anche permesso di mettere al chiuso, e al sicuro la moto in un suo garage, rendendo così felice il mio compagno 😉. Ci ha ha dato consigli sui luoghi da visitare e consigliato di cenare al ristorante del paese e ne è valsa proprio la pena. Consigliatissimo! Silvia e Giovanni

Guest favorite

The room features a curved ceiling with exposed wooden beams, creating a unique architectural element. Large windows allow natural light to fill the space, enhancing the light-colored walls. A vintage chair and a wooden door complete the serene and inviting atmosphere.

Hotel room in Siena

4.95 out of 5 average rating, 21 reviews

Suite Pandolfo Petrucci

EmmaRating, 5 stars7 months ago

We highly recommend staying with Rita if you are ever in Siena. The suite is stunning, bigger and cosier than the photos! The location of the suite is very central to Sienna and close to everything you need. Not to mention a beautiful view of the Baptistery of Siena from your window… We were made to feel very welcome by all of the staff, and the team were incredibly helpful and responsive. We went for the valet parking option that they offered, which is well worth the money and stress free parking (if driving). Thank you again for hosting us!

Guest favorite

An outdoor swimming pool is framed by lush greenery and features several sun loungers arranged around it. The expansive views showcase rolling hills under a clear blue sky, enhancing the serene environment. A peaceful and inviting atmosphere is created by the well-maintained lawn.

Hotel room in Piancastagnaio

4.93 out of 5 average rating, 82 reviews

Camera Antica Foresteria

MadisonRating, 5 stars2 weeks ago

Such a gorgeous and unique place to stay. This was definitely one of the nicest places we have ever stayed. The room was clean and spacious, the surrounding gardens and pool were also amazing and the food in the restaurant is also very nice. We will definitely be returning in the future!

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Popular amenities for Province of Siena boutique hotel rentals

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Family-friendly boutique hotels rentals

Superhost

A narrow street is lined with historical buildings showcasing brick facades and arched doorways. The atmosphere is enhanced by the tall towers in the background, offering a glimpse of the medieval architecture characteristic of the area.

Hotel room in San Gimignano

4.71 out of 5 average rating, 41 reviews

San Gimignano 2 rooms 4/5 persons with view

CarolineRating, 5 stars1 week ago

Really enjoyed our stay, beautiful accommodation and very comfortable . Made to feel very welcome

Guest favorite

A charming courtyard is framed by brick arches, featuring a few tables with ornate metal chairs. Potted plants with vibrant flowers add a touch of color, while cozy seating is arranged in the background, inviting relaxation and quiet moments.

Hotel room in San Gimignano

4.76 out of 5 average rating, 277 reviews

San Gimignano rooms private fast Wi-Fi -10

JosepRating, 5 stars2 weeks ago

De todas las estancias que hemos realizado en nuestro viaje a la Toscana, ha sido el mejor alojamiento y la mejor anfitriona de todas, 1000% recomendable, volveremos seguro en nuestro proximo viaje, muchas gracias por todo

Superhost

A double bed with an ornate headboard is dressed in a gold patterned bedspread. A delicate lamp illuminates the bedside table, while a small antique chair and a decorative fireplace are visible in the background, enhancing the room's classic Tuscan style.

Hotel room in San Gimignano

4.64 out of 5 average rating, 206 reviews

Private double room San Gimignano WiFi -6

DollyRating, 5 stars1 month ago

I had a wonderful stay in San Gimignano and absolutely loved this place! The location is perfect—peaceful and full of charm, just like the town itself. The accommodation was cozy, welcoming, and had a lot of character, which added to the overall experience. While the bathroom is a bit old, it was spotless and well-maintained, so it didn’t bother me at all. The warmth of the place and the beauty of the surroundings more than made up for it. I’d happily stay here again and recommend it to anyone looking for an authentic and relaxing stay in San Gimignano.

Superhost

This double room features a traditional Tuscan design with original wooden furniture and terracotta flooring. Natural light filters through the large window, highlighting the intricate carvings on the bed's headboard. A cozy area rug adds warmth, while bedside lamps provide a soft glow.

Hotel room in San Gimignano

4.61 out of 5 average rating, 47 reviews

San Gimignano private double room -4

JulieRating, 5 stars8 months ago

Sehr schönes Zimmer und Aufenthaltsraum und -hof, mitten im Zentrum von San Gimignano, gut erreichbar, wunderbare Kommunikation. Man fühlt sich als wäre man in der Zeit gesprungen. Bad ist klein.

Top guest favorite

A spacious red brick building is set within a lush green landscape, featuring manicured lawns and flower beds. Outdoor seating is offered under canopies, with expansive skies in the background showcasing scattered clouds. Open fields extend beyond the property, creating a serene environment.

Hotel room in Bettolle

4.92 out of 5 average rating, 37 reviews

Camera matrimoniale Superior in casa Leopoldina

BenRating, 5 stars6 months ago

Good stay at Walter’s place in Tuscany. Place wasn’t as out in the country as we expected but it was convenient near a town and the rooms were very clean and well kept with friendly service.

Guest favorite

A well-appointed bedroom features a plush, light-colored headboard above a spacious bed. Two wall-mounted lamps provide soft lighting, while minimalist side tables flank the bed. The walls are painted in a warm hue, contributing to a restful ambiance.

Hotel room in Siena

4.89 out of 5 average rating, 150 reviews

Charming Room one step from Duomo 3

JavierRating, 5 stars2 months ago

Buena ubicación. Sitio bonito y tranquilo. La habitación estaba muy limpia, tal y como en las fotos. Fabio respondió a todas nuestras cuestiones de forma rápida y fue amable en todo momento. Recomendable.

Guest favorite

The exterior of a historic brick building is illuminated at dusk, highlighting architectural details such as arched windows and a staircase. Lush greenery and lavender plants enhance the landscaped garden, while soft lighting creates a welcoming ambiance throughout the property.

Hotel room in Bettolle

4.94 out of 5 average rating, 205 reviews

Nice double room in a charming B&B

JINYIRating, 5 stars3 weeks ago

This place is simply a dream! Every window in the house looks like a painting—nature is framed so beautifully that it takes your breath away. The room itself was stunning, full of warmth and style. The host was incredibly kind and respectful. We truly appreciated the upgrade to a better room and all the thoughtful help we received. From showing us how to buy train tickets, to calling a taxi and even helping with our luggage—it felt like staying with a dear friend who truly cared. And yet, they were never intrusive—just wonderfully supportive when needed. And the food—wow! Every meal was delicious and generous. The breakfast croissants and fresh milk are unforgettable, and the cleanliness and cozy environment made everything feel perfect. We genuinely didn’t want to leave. “Home away from home” doesn’t even begin to describe it. It was beyond amazing. We wholeheartedly recommend this place to everyone—it’s an experience you don’t want to miss!❤️❤️❤️☺️

Hotel room in Castenuovo di Val di Cecina

4.25 out of 5 average rating, 4 reviews

Agriturismo "Le Cerinaie": Two-bedroom apartment

LucaRating, 5 stars8 months ago

Molto ospitali, molto gentili, ottimo rapporto qualità prezzo!

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Boutique hotel vacation rentals in Province of Siena

Top-rated boutique hotel rentals in Province of Siena

Vacation rentals for every style

Popular amenities for Province of Siena boutique hotel rentals

Family-friendly boutique hotels rentals

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