Some info has been automatically translated. Show original language

Holiday rentals in Val di Paglia

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Val di Paglia

Guests agree: these stays are highly rated for location, cleanliness and more.

%{current} / %{total}1 / 1
Top guest favourite
A vibrant garden features an array of colorful flowers, with delicate white blooms prominently displayed. In the background, rolling hills are seen under a dramatic sky, creating a serene landscape filled with natural beauty.
Home
4.95 out of 5 average rating, 107 reviews

Da nonna Ornella - nest in Val d'Orcia

Spectacular views and relaxation guaranteed in this romantic studio in the heart of the Val d'Orcia, province of Siena, immersed in the beautiful Tuscany. Ideal for couples. It has a living area, equipped kitchen, bathroom, heating, courtyard, private parking and a large and panoramic garden with sun loungers and a hammock. Close to iconic destinations: PIENZA, Montepulciano, Montalcino, Bagno Vignoni, Bagni San Filippo, San Quirico d'Orcia, Radicofani, Castiglione d'Orcia and Monte Amiata. Unforgettable!

Top guest favourite
An aerial view showcases a historic building with a tiled roof, situated against a rocky cliff. A terrace with seating and a small table is visible, surrounded by greenery below, evoking a sense of tranquility and connection to nature.
Apartment
4.99 out of 5 average rating, 143 reviews

Le Antiche Viste - The Zen Terrace

Enjoy the tranquillity and the stunning views. Treat yourself to an aperitivo on the terrace, and relax in the zen living room. A stylish 100 sq m gem just for you, with 1.5 bathrooms, TV, kitchen, and fast wi-fi for remote working. Perfect for a couple (or a solo traveller). Bedroom is equipped with air conditioning! If you're passionate about combating climate change, you can opt for the ceiling and floor fans available in every room. They ensure a refreshing stay, even on the warmest days.

Top guest favourite
An inviting interior features exposed brick walls and a blend of modern and rustic design elements. A staircase leads to the upper floor, while large doors open to reveal a view of the outdoors. A wooden table and a cozy chair enhance the living space.
Flat
4.97 out of 5 average rating, 119 reviews

Under the sunset, Montepulciano

In 2023 my son Guglielmo and I decided to restore the old oratory of a church from the 1600s by creating a two floor apartment: upstairs we have 2 bedrooms equipped with AC and 2 en-suite bathrooms with shower; downstairs a spacious living room with stereo Available a table outside with great view and a nice garden 50 mt away where to have a private wine tasting for all the guests of our 4 apartments We can organize barbecue with paired wines after 7 pm. Large free parking area 100 mt away

Top guest favourite
A spacious rooftop terrace is showcased, featuring a black chair and a table positioned near flowering red plants. Sunlight casts shadows on the tiled floor, highlighting the surrounding terracotta rooftops and greenery in the distance, offering a scenic view of the medieval town.
Home
4.98 out of 5 average rating, 161 reviews

La Casetta di Alice - with panoramic terrace -

The house is in the heart of the medieval historic center of Abbadia S. S. Distributed over several levels, it has two independent entrances, and a large roof terrace, equipped solarium, from which you can admire a beautiful view. Recently renovated, it offers a unique and welcoming atmosphere. TV in the living room and in the bedroom. Ultra-fast FASTWEB Wi-Fi. For a couple with a child, there is also the option to add a single bed in the room with the parents. Self check-in is available.

Top guest favourite
A charming cottage is shown with a terracotta facade and a tiled roof. A small table with two chairs is set on a patio, surrounded by potted plants. Lush greenery and trees can be seen in the background under a clear blue sky.
Guest house
4.97 out of 5 average rating, 199 reviews

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.

Guest favourite
A spacious bedroom features a large, inviting bed adorned with a light blanket. Natural light floods through sheer curtains draped over a large window, revealing views of the lush valley outside. The rustic walls, made of tufo, add a unique character to the room.
Flat
4.94 out of 5 average rating, 243 reviews

The Cellar (Palazzo Pallotti)

The apartment is two floors below the square, entirely dug into the tuff. Overlooking the valley, it is isolated from the noises of the street, quiet, private, and very welcoming. The tuff walls give it an ancient vibe to transport you to another time. It can be reached on foot, via a footbridge that takes you directly to the square where the property is located. It is perfect for short stays of complete relaxation, but with the fully equipped kitchen you can make the most of it.

Top guest favourite
A scenic view captures a rustic stone house set amid rolling hills and olive trees. The expansive landscape features golden fields and lush green foliage, with a winding path leading to the home. The sky is clear, enhancing the serene countryside atmosphere.
Apartment
4.96 out of 5 average rating, 388 reviews

Romantic Yellow apartment in Crete Senesi

Apartment consisting of 1 comfortable double bedroom (it is possible to make 2 single beds on request), equipped kitchen, living room and bathroom. TV, BBQ, (if necessary, we provide the washing machine from 9 a.m. to 8 p.m., which is located in our laundry room). A car is recommended as we are in the countryside, so you can be self-sufficient and so you can visit the magnificent Tuscan countryside as well. Free parking and wifi. I look forward to showing you the real Tuscany!

Top guest favourite
An exterior view of a charming Tuscan house featuring warm stone walls. The surrounding garden includes manicured grass and potted plants. A spacious patio with a table for outdoor dining is visible, alongside a stone pathway leading to the entrance.
Guest house
4.97 out of 5 average rating, 113 reviews

Casale Santa Barbara - Exclusive Apartment

At a glance: • Location: perfect entry door to the Val d’Orcia between Pienza (8,5 km) and Montepulciano (8,5 km). • Charming warm old stones Tuscan house – completely restored in 2016 • Big apartment (100m2), designed for 2 persons, completely independent, fully furnished, Tuscan style with modern equipment. • Exclusivity: we are living on the 1st floor; the ground floor is yours. You are our only guests. • Spacious private garden (+ 300m2) • Stunning view on the Tuscan hills.

Top guest favourite
An outdoor wood-fired hot tub is surrounded by lush green grass, offering a scenic view over the expansive landscape. A stone pathway leads to the hot tub, while the rustic stone cottage is visible in the background under a partly cloudy sky.
Cottage
4.99 out of 5 average rating, 150 reviews

Your Private Tuscan Retreat

This beautiful sheepherder’s stone cottage is equipped with modern comforts and spa facilities free of charge. The large grounds of forest and meadow span a ridge and provide panoramic views of the valley toward Val d’Orcia to the north, the expansive Maremema to the south, and the ancient volcano of Amiata to the west. This is the perfect getaway for those wanting a private retreat from which to explore the rich wine, food, culture, history, and landscape of southern Tuscany.

Top guest favourite
An aerial view showcases a charming stone cottage surrounded by lush greenery and mature trees. The roof is partially covered with natural foliage, blending the structure harmoniously into the landscape. The area features rocky outcrops and dense vegetation, highlighting the peaceful rural setting.
Farm stay
4.99 out of 5 average rating, 259 reviews

Terra Delle Sidhe, Seggiano, Tuscany, Italy

Terra delle Sidhe is a small organic farm located in southern Tuscany overlooking a beautiful valley located on the slopes of Monte Amiata, between the medieval towns of Castel del Piano and Seggiano. A 250 year old chestnut dryer stone house in use till 30 years ago, the holiday cottage we offer is surrounded by an organic chestnut forest and olive trees that are hundreds of years old. This charming cozy house it has now been lovingly renovated with taste and simplicity.

Top guest favourite
A view from the window reveals a serene landscape of rolling hills and valleys bathed in soft morning light. The garden below is adorned with colorful flowers and greenery, enhancing the tranquil atmosphere of the Tuscan countryside.
Home
4.99 out of 5 average rating, 218 reviews

Alma Vignoni - Vignoni Val d'Orcia - Bagno Vignoni

Alma Vignoni is an elegant and exclusive holiday house in Vignoni Alto that recalls Tuscan style and is enriched by unusual and personal details. The house consists of an open-space with fireplace in the center. On the one hand the room with stunning views over the surrounding hills (Pienza, Monticchiello and Montepulciano) on the other the kitchen area. Two cozy rooms overlook the ancient Via Francigena and the Orcia river valley. The bathroom has a large shower.

Guest favourite
A traditional stone casale is set among lush greenery, featuring wooden shutters on the upper windows. Olive and fruit trees frame the home, enhancing its natural setting. A well-maintained lawn extends around the property, inviting relaxation in this peaceful environment.
Cabin in Cetona
4.96 out of 5 average rating, 139 reviews

Poggio dell'orso.Traditional Casale. Amazing views

Fantastic, recently restored, 150 years old Casale in Tuscany with amazing views. Two bed rooms, a spacious living room with a double sofa bed, a 85" smart TV, a corner with a desk and a fully equipped kitchen. Outside a stone table, a huge garden, a gazebo, a state of art warmed Jacuzzi (optional if available) a fantastic 6 x 12 infinity pool . All the property is fenced. Pet friendly.

Popular amenities for Val di Paglia holiday rentals

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Siena
  5. Val di Paglia