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Holiday rentals in San Leonino

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Top-rated holiday rentals in San Leonino

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Top guest favourite
An aerial view showcases the expansive grounds of La settecentesca Villa di Geggiano, surrounded by manicured gardens and lush vineyards. The main villa is prominent, with a circular driveway leading to it, while gentle hills extend into the background.
Cottage in Geggiano
4.99 out of 5 average rating, 145 reviews

Villa di Geggiano - Guesthouse

PLEASE NOTE THAT BEING IN THE COUNTRYSIDE WITH FEW PUBLIC TRANSPORTATION OTHER THAN TAXI, THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A CAR. The 18th century Villa di Geggiano, surrounded by vineyards and lovingly cared gardens, is located in the Chianti area near Siena, one of the most beautiful regions of Italy which will provide an idyllic and enchanting backdrop to your vacation. Our guesthouse is located in one of the garden pavilions of the villa.

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 in Macciano
4.97 out of 5 average rating, 207 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.

Top guest favourite
A lush green garden is framed by a rustic pergola made of wooden beams. Grassy paths lead deeper into the garden, where vibrant flowers and trees provide a natural backdrop. Rolling hills and a clear blue sky are visible in the distance, creating a serene outdoor setting.
Home in Castellina in Chianti
4.98 out of 5 average rating, 127 reviews

StageROOM03 - Idyllic Chianti cottage near Siena

Set in a picturesque hamlet, overlooking the Chianti hills, this charming country house is just 10 minutes from Siena and Castellina in Chianti. Recently renovated, it blends authentic Tuscan charm with modern comforts. The house features two bedrooms, two bathrooms, a cozy living area and a fully equipped kitchen with a dishwasher, two fridges, and a washing machine. Outside, enjoy a beautiful garden and relax in the outdoor marble hot tub, soaking in the breathtaking views.

Guest favourite
Flat in Poggibonsi
4.97 out of 5 average rating, 58 reviews

Capanna, typical house in Chianti with pool

The Capanna apartment is located in a typical Tuscan village in the middle of the hills and not far from San Gimignano, Siena, Florence, Volterra and in the center of Chianti where you can discover magnificent wineries to taste good Chianti wine. The apartment is furnished with original Tuscan furniture and other details, swimming pool with splendid views and large garden. Inside everything you need to cook and relax reading a book or a good glass of wine, bbq, free parking.

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Villa in Badia a Passignano
4.67 out of 5 average rating, 3 reviews

Guardia di Badia a Passignano

Guardia di Badia a Passignano is a lovingly restored villa which is ideal for couples or small families. Once a guard’s post, it now offers a peaceful and stylish retreat in the heart of Chianti, surrounded by the renowned vineyards of Antinori, one of Italy’s most respected wine producers. Just a short walk away lies the impressive Badia a Passignano, a thousand-year-old abbey with a Last Supper fresco by Domenico Ghirlandaio.

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The outdoor swimming pool features a spacious area for relaxation, surrounded by well-maintained sun loungers. A gentle slope leads down to the pool, with scenic views of rolling hills and olive trees in the distance. Sun umbrellas provide shade on sunny days.
Flat in Montepulciano
5 out of 5 average rating, 4 reviews

Apt 2: Montepulciano 800 yr old Monastery

Our self catering accommodation is in an 800 year old converted monastery situated 5 minutes drive from the Renaissance town of Montepulciano, renowned for its Vino Nobile wines, close to art and culture, with great views, restaurants, coffee bars and enotecas. Our local area is a paradise for hikers, cyclists, joggers or simply walking through the incredible Tuscan country side that offers memorable sights of farmland, forests and rolling hills.

Top guest favourite
A stone facade is viewed from a well-maintained garden, featuring lush green grass and neatly trimmed hedges. A wooden door is visible, leading into a charming interior, while the house's rustic architecture complements the serene landscape under a clear blue sky.
Home in Castellina in Chianti
4.98 out of 5 average rating, 111 reviews

Explore Chianti from a Charming Stone House

Awaken in a bedroom with beamed ceilings, open doors to a private garden, and take an early morning dip in the pool. Return to a classically designed house with terra cotta floors, wood-burning fireplace, and bathrooms with exuberant tile work. Casa Marinella is the perfect place to discover Chiantishire. Fully equipped kitchen, AC in each bedroom, private garden and barbecue.

Top guest favourite
The exterior of the country house is framed by tall, narrow cypress trees and well-maintained gardens featuring various plants. A terracotta pot stands prominently, and gravel pathways lead to the entrance, which is characterized by stone walls and an arched doorway.
Home in Tavarnelle Val di Pesa
4.96 out of 5 average rating, 318 reviews

Casa Al Poggio & Chianti view

Casa al Poggio is a typical country house of Chianti area is spread in 145 square meters on two floors, the ground floor is a large living area, with kitchen and sofa ,fireplace ,up stairs there is 2 large double bedrooms and a sofa bed in the middle open room , always setable as 2 singles or a double bed bed and a relaxing bathroom with shower and bath with Chianti view.

Guest favourite
Apartment in Fonterutoli
4.93 out of 5 average rating, 27 reviews

Charme toscano a Fonterutoli Travi a vista & relax

Benvenuti nel borgo storico di Fonterutoli, un luogo incantevole immerso tra le colline del Chianti, a metà strada tra Siena e Castellina in Chianti. L’appartamento si trova all’interno di un piccolo resort vinicolo che offre un’atmosfera unica: privacy, tranquillità e panorami autentici, perfetti per chi cerca un soggiorno rilassante nella Toscana più vera.

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Villa in IT
4.5 out of 5 average rating, 14 reviews

Stone house with private pool Vacavilla Exclusive

Property for exclusive use Casale San Donatino is an old stone house, 480 sq mt, holding up to 12 persons with 6 double bedrooms and 3 bathrooms. The house has a splendid, panoramic, private swimming pool, WiFi and a barbecue. It is ideal for groups of friends or large families.

Guest favourite
A tranquil garden space is visible, featuring a large, white umbrella providing shade over two reclining chairs. Lush green grass surrounds the area, complemented by potted greenery and flowering plants, creating a serene outdoor escape.
Flat in Siena
4.93 out of 5 average rating, 113 reviews

Casa Borgianni at Villa Caprera

Distinguish historic family villa with a bucolic charm for a true Tuscan holiday in a set of olive trees, gardens, vineyards, old churches. Just five minutes from Siena centre with an amazing view of the city. A relaxing place with all comforts

Top guest favourite
A bright bedroom features a spacious bed with a soft yellow quilt. Natural light enters through a window and glass doors that open to a private garden area. A bedside lamp and a wooden nightstand add to the room's functionality.
Farm stay in Siena
4.98 out of 5 average rating, 276 reviews

Typical Tuscan Country House WITH A/C

L'appartamento "Fienile" (75 mq), è una delle due unità abitative indipendenti che compongono l'agriturismo Terra Rossa, situato nel cuore della campagna senese a pochissimi minuti di macchina dal centro storico.

Popular amenities for San Leonino holiday rentals

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Siena
  5. San Leonino