Vacation rentals in Siena

5 out of 5 average rating, 257 reviews

Aerial view showcases the rustic property nestled among the lush vineyards. Sunlight casts a warm glow over the hills, while a sparkling pool is situated near the residences, surrounded by greenery. The tranquil landscape includes gently rolling hills and rows of grapevines.

Condo in Noce

Podere Vergianoni immerso nelChianti con piscina

Podere Vergianoni is an ancient and authentic farmhouse dating back to the 17th century located in the beautiful hills of Chianti in Tuscany. The apartment is impeccably furnished in the traditional local style of old Tuscany: ancient wooden beams, terracotta floors, and unique furniture. In the large outdoor courtyard, you'll find a large swimming pool on a panoramic terrace at your disposal, overlooking the valley with breathtaking views of vineyards and olive groves, where you can enjoy spectacular sunsets.

Farm stay in Castelnuovo Berardenga

4.92 out of 5 average rating, 284 reviews

Apartment in Tuscan farm house.

Small, cosy apartment with independent access, consisting of charming bedroom with a beautiful view, equipped with ample closet space, a comfortable canopy bed and private bathroom and pretty living room / breakfast area, with sofa-bed. A delicious breakfast is included in the price and from April through October guests also have the option of dining on-site in our traditional farm restaurant. If dates are not available the property includes other rooms in charming cottage also on Airbnb.

4.96 out of 5 average rating, 167 reviews

A swimming pool is framed by a shaded pergola adorned with green vines. Tan lounge chairs are arranged beside the pool, surrounded by lush olive and cypress trees. A small table with a potted flower adds a touch of color to the inviting outdoor space.

Guesthouse in Macciano

Tuscan cottage with an heavenly view

Heaven's Window takes your breath away. As our only guests, you will be surrounded by infinite views, endless tranquility, sounds of singing birds and calling deer. Down the valley and on your walks you may spot foxes ferrets and wild boar. Collect porcupine quills. Breathe! Halfway between Rome and Florence. Close to Siena, Val d’Orcia and countless hot springs . A private paradise surrounded by divine dining and hilltop jewels of antiquity like Montepulciano and Montalcino of sublime wines.

4.96 out of 5 average rating, 241 reviews

Cottage in Monteriggioni

Monteriggioni Castello, holiday house in Tuscany

Il nostro alloggio è un edificio storico che risale alla costruzione del castello. È stato recentemente restaurato e arredato con cura in tutti i dettagli. È molto accogliente e dispone di tutti i più moderni servizi. I turisti che decideranno di essere nostri ospiti, avranno il vantaggio di vivere nell' ambiente medievale del castello, usufruendo di tutti i confort. Si sentiranno coccolati e avranno l'opportunità di tornare indientro vivendo un' esperienza unica e indimenticabile.

4.99 out of 5 average rating, 179 reviews

Home in Gambassi Terme

Il Fienile, Luxury Apartment in the Tuscan Hills

‘Il Fienile’ is in an enchanting position immersed in the beauty of the Tuscan hills, with a breathtaking view of the surrounding countryside. It is located in the hamlet of Catignano in Gambassi Terme, just a few kilometres from San Gimignano. The house sits in a protected oasis surrounded by a beautiful private park with olive trees, a pond, pine trees and woods, where you can walk, relax and enjoy the pleasures of unspoilt nature. A unique experience entirely to be enjoyed.

4.93 out of 5 average rating, 140 reviews

A spacious garden is featured, surrounded by well-established trees. A wooden dining table with several chairs is positioned in the foreground, while a rustic building is set back in the landscape, creating a serene outdoor environment.

Farm stay in Sovicille

House at Gianni - Olmo

Hi, we're Cristina & Carmelo! We invite you to discover the rustic charm and authenticity of "Casa al Gianni," our farmhouse in the heart of the Tuscan countryside, 20 minutes from Siena. After a recent renovation, our accommodations are ready to welcome you with all modern comforts without losing the essence of tradition. In the Olmo Apartment, brand new beds await you, a promise of peaceful and regenerating sleep, a new kitchen and a new bathroom.

4.93 out of 5 average rating, 120 reviews

A scenic view of rolling hills and lush greenery is visible from a window. Terracotta roofs and a winding path can be seen below, enhancing the historic charm of the medieval surroundings.

Condo in San Gimignano

Luxury Medieval Tower - Penthouse

Step into the past... San Gimignano Luxury Medieval Tower is right in the heart of the UNESCO town. You will be caught by the sight of San Gimignano's beautiful landscapes and at the same time you will be able to enjoy the luxury amenities of in-town living: walk downstairs to the cafes, bread shop, butcher, restaurants and local shops. Hear the church bells directly from your windows. Walking distance to all of San Gimignano main attractions.

Villa in Monteroni d'Arbia

A simple work nook is presented with a white chair and a natural wood desk, positioned near a window. A vase with delicate flowers sits on the desk, with soft light enhancing the serene view of the surrounding landscape.

4.95 out of 5 average rating, 137 reviews

"Villa Daisy" overlooking Siena

Wonderful villa with independent entrance inside the "Caggiolo" farm, brought to light with careful and thorough renovation that has kept intact the typical features of a Tuscan farm. Beautiful panoramic view of Siena. Located in Ville di Corsano, just 14 km from the city. An ideal place to spend days in total relaxation and enjoy the wonders that this area offers (Chianti, Val d'Orcia, Crete Senesi etc).

A panoramic view showcases the charming rooftops of the city, with terracotta tiles and historic buildings. The Torre del Mangia stands prominently in the background, alongside lush greenery and the distant valley. The cloudy sky adds depth to this serene urban landscape.

4.95 out of 5 average rating, 358 reviews

The rooftop terrace

Bright and cozy 95 sqm apartment located on the 4th floor without elevator of a notified building in the heart of the city a few steps from Piazza del Campo, the Duomo and the major attractions of the city. A splendid view overlooking the rooftops will frame your apartment from which you can see the Torre del Mangia, the Basilica dei Servi and the wonderful Val d'Orcia.

The image captures an impressive view of the Torre del Mangia, a tall brick tower rising above the historic architecture of Siena. Surrounding buildings feature a blend of warm colors, while the expansive Piazza del Campo is visible below, framed by cobblestone paths and open spaces.

4.9 out of 5 average rating, 470 reviews

Apartment in Piazza del Campo-Balcone delle Aquile

A cozy apartment with a terrace with unparalleled views of the Torre del Mangia tower and Piazza del Campo. The apartment has three comfortable bedrooms, a living room, a large bathroom and a fully equipped kitchen. A perfect terrace from which to see the Palio, as indicated in the reviews.

Farm stay in Gaiole in Chianti

A spacious bedroom features a large bed adorned with soft linens and two neatly rolled towels. Warm terracotta tiles cover the floor, complemented by pale yellow walls and wooden beam ceilings. Natural light fills the room through two windows with dark shutters, creating a calming ambiance.

4.94 out of 5 average rating, 233 reviews

Il Nido - a romantic hearth

Lui non esisteva, è stato ricavato in un angolo della grande casa in cui chissà quante persone della stessa famiglia vivevano. Per questo è diventato il nostro piccolo Nido, la casa da cui partire per scoprire il borgo. Non un piano ma addirittura due, con tanto cotto, legno e colori caldi.

A narrow alleyway is framed by historic stone buildings, their windows reflecting the warm glow of twilight. The sky displays a gradient of pink and purple hues as the sun sets, complemented by softly illuminated window panes that hint at life within.

4.98 out of 5 average rating, 356 reviews

In Siena, between roofs and sky.

In the center of Siena's history, between roofs and sky, you will be accommodated in a cozy and spacious apartment that you can share with your family and with your friends. Located in the heart of the city, it's just a few steps from the Cathedral and the marvelous Piazza del Campo.

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Apartments

Convenient locations with everyday essentials

Villas

Luxurious estates for the ultimate escape

Popular amenities for Siena vacation rentals

Laptop-friendly workspace

Boutique hotels in Siena

4.95 out of 5 average rating, 22 reviews

A view from an open window reveals the intricate façade of a historic building, providing sight of decorative doors and columns. Outdoor seating with umbrellas is visible at the base, along with people enjoying the space, framed by the surrounding architecture.

Hotel room in Siena

Pandolfo Petrucci Suite

4.97 out of 5 average rating, 145 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

Hotel room in Centro Storico

A hallway is framed by a brick arch, featuring a combination of light-colored walls and tiled flooring. Artwork hangs on the walls, alongside decorative items on a wooden console table. Natural light fills the space, enhancing its welcoming ambiance.

4.86 out of 5 average rating, 147 reviews

Single Room

Hotel room in Centro Storico

A well-lit hallway features wooden flooring and framed artwork along the walls. A cozy seating area is positioned beside a window, with a small table holding a vase of fresh flowers. Natural light brightens the space, enhancing the welcoming atmosphere.

4.95 out of 5 average rating, 311 reviews

AM Collection Florence

Hotel room in Castelfranco di sopra

A stunning view from a hillside captures a serene pool area at sunset. The scene is filled with vibrant colors in the sky, with lounge chairs arranged beside a sparkling pool. Trees and distant hills are visible in the background, adding depth to the landscape.

4.89 out of 5 average rating, 169 reviews

Romantic Medieval Village with pool

Superhost

The image captures a historic street view featuring rustic brick buildings with arched windows. A flag flies above, adding a touch of color. Motorcycles are parked along the cobblestone street, which gently curves around the corner. The scene reflects the charming architecture of Siena.

Hotel room in Siena

4.79 out of 5 average rating, 116 reviews

Charming Room at the Duomo 2

Superhost

Hotel room in Rifredi

4.84 out of 5 average rating, 110 reviews

The Villino Fiorentino, superior king room

5 out of 5 average rating, 77 reviews

A stone staircase leads up through landscaped gardens under the shade of a large tree. Potted plants are arranged along the steps. Tables and chairs are set along the path, offering inviting spots to enjoy the surrounding views of the Tuscan landscape.

Hotel room in Panzano

Villa La Petraia Elysian

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Other great vacation rentals in Siena

4.98 out of 5 average rating, 109 reviews

A small terrace is showcased, featuring a bistro table with two chairs. Scenic views of lush greenery and rolling hills extend beyond, with several trees dotting the landscape. The sky is bright and clear, creating an inviting outdoor space.

Hut in Siena

Guido's Cabin

A view from the window reveals a historic brick building featuring white marble accents. Stairs lead down alongside the structure, while decorative flags hang in the foreground. The sky above showcases scattered clouds, providing a sense of openness to the scene.

4.94 out of 5 average rating, 142 reviews

Luce in Provenzano

4.87 out of 5 average rating, 128 reviews

Elegant flat+ rooftop 450mt from Piazza del Campo

The elegantly structured Villa di Geggiano is set amidst lush vineyards and well-maintained gardens. Its classic stone facade and terracotta roof harmonize with the surrounding greenery, while neatly manicured pathways and symmetrical garden beds create a picturesque landscape under a partly cloudy sky.

4.99 out of 5 average rating, 158 reviews

Villa di Geggiano – Alfieri Suite

Superhost

4.92 out of 5 average rating, 239 reviews

Palazzo Casini Piccolomini Apartment

4.97 out of 5 average rating, 231 reviews

Farm stay in Arezzo

Explore nature in the center of Vigneti Chianti

Villa in Tavarnelle Val di Pesa

An outdoor dining area is presented under a shaded canopy, featuring a long table set with decorative plates and colorful glasses. A view of rolling hills and a swimming pool is visible in the background, creating a serene atmosphere for al fresco meals.

4.93 out of 5 average rating, 149 reviews

GUIDI POWER