Boutique hotel vacation rentals in Province of Siena

5 out of 5 average rating, 14 reviews

An aerial view captures the spacious surroundings of the villa, featuring a rectangular pool and a large stone patio. Sun loungers are arranged around the pool, while lush greenery and cypress trees frame the area, enhancing the serene outdoor environment.

Hotel room in Panzano

Villa La Petraia, Anam Cara Suite

MelisaRating, 5 stars6 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.

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.

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.

4.97 out of 5 average rating, 126 reviews

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

Sleeping on Siena roof

JoshRating, 5 stars1 week ago

We had a lovely one night stay during our Tuscany trip. The room was clean, cozy, and the view is very special. Francesca gave clear instructions that made our visit seamless. In our room we found a list of her personal local recommendations for where to eat, walk, and shop. We enjoyed these very much.

Hotel room in Montepulciano

A tranquil infinity pool is framed by well-maintained greenery and manicured lawn areas. The rustic farmhouse stands in the background, featuring distinct architecture with a tiled roof. Lavender plants and trees create a serene atmosphere, enhancing the connection with the Tuscan countryside.

5 out of 5 average rating, 27 reviews

Wellness and relaxation in the Tuscan hills

AshleighRating, 5 stars3 weeks ago

I can’t recommend this stay enough. The property itself is stunning - quiet and peaceful, surrounded by beautiful gardens, with the rolling hills of Tuscany. The room contains all modern ammenities with rustic touches to match the vibes - everything is very clean, large comfortable bed and a huge bathroom to enjoy a cosy, relaxing stay. The host Raffaele is fantastic - he was extremely prompt with communication, gave us local recommendations and took care of making any reservations (including advising best parking options making things easy to navigate). He really goes above and beyond. We also organised to do a cooking class on site with the chef, Carlotta, which was amazing. She has such a good energy and we had so much fun learning how to make pasta etc and felt very lucky to be able to do that in an intimate setting. You even get copies of the recipes and an apron to keep afterwards! If you’re looking for a place to switch off and enjoy an authentic Tuscan experience, go here!

Hotel room in Campagnatico

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.

4.95 out of 5 average rating, 19 reviews

Independent Deluxe Room with Panoramic View

SilviaRating, 5 stars5 months ago

On a weekend on a motorcycle, passing through the area we stayed in Servilio's wonderful guest house. The village of Campagnatico is a small gem worth visiting, getting lost in the streets to discover the cistern, the spring, the sundial and the steps of Dante Alighieri. Servilio's room, his home and hospitality are worth the trip alone. The renovated and tastefully furnished room has a beautiful view of the surrounding countryside and part of the town, and has everything you need to relax: a very comfortable king size bed, air conditioning, fridge, TV, kettle. The bathroom is huge, with a beautiful window with a view and a large walk-in shower. The host also allowed us to put the bike indoors and safely in his garage, making my partner so happy😉. He gave us tips on places to visit and recommended dining at the village restaurant and it was really worth it. Highly recommended! Silvia and Giovanni

4.95 out of 5 average rating, 21 reviews

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

Pandolfo Petrucci Suite

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!

Hotel room in Piancastagnaio

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.

4.93 out of 5 average rating, 81 reviews

Antica Foresteria Room

MaresaRating, 5 stars1 week ago

This place is a treasure! So historic and preserved beautifully by dedicated family members. So beautiful, friendly host and staff, very comfortable. Also, so much to see in the area such as Bagni San Filippo Hot Springs, Montalcino, Pienza, Monticchiello , and more. Make the time. The is a bucket list destination.

Vacation rentals for every style

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Quaint homes, peaceful surroundings

Popular amenities for Province of Siena boutique hotel rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly boutique hotels rentals

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.

4.7 out of 5 average rating, 40 reviews

San Gimignano 2 rooms 4/5 persons with view

BernardoRating, 5 stars1 month ago

Very helpful and professional host. He showed a lot of patience and I can only thank him for the wonderful stay

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.

4.76 out of 5 average rating, 276 reviews

San Gimignano rooms private fast Wi-Fi -10

AaronRating, 5 stars1 week ago

What a beautiful unique and beautiful place to stay! You are literally in a medieval palace with 2foot thick stone walls, but it feels like a cozy home. Absolutely stunning! The town is beautiful with lots of shops and restaurants. Highly recommend!

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.

4.64 out of 5 average rating, 206 reviews

Private double room San Gimignano WiFi -6

DollyRating, 5 stars3 weeks 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.

4.61 out of 5 average rating, 47 reviews

San Gimignano private double room -4

JulieRating, 5 stars7 months ago

Very nice room and common room and courtyard, right in the center of San Gimignano, easily accessible, wonderful communication. You feel like you jumped in time. Bathroom is small.

4.92 out of 5 average rating, 37 reviews

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

Superior double room in Leopoldina house

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.

4.89 out of 5 average rating, 150 reviews

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

Charming Room one step from Duomo 3

JavierRating, 5 stars1 month ago

Good location. Nice and quiet place. The room was very clean, just as shown in the photos. Fabio answered all our questions quickly and was kind at all times. Recommended.