Vacation rentals in Pillo

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Top-rated vacation rentals in Pillo

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Top guest favorite

Vacation home in San Gimignano

4.97 out of 5 average rating, 118 reviews

Breathe in Tuscany: 180° view of the hills

Please note that the second bedroom is divided from the hallway by a curtain and not by a door. in Experience your experience in San Gimignano with a splendid view of the Tuscan hills! In the heart of San Gimignano, experience the city with an independent entrance, first floor and breathtaking views of the Tuscan hills. Private parking space available upon request. Entrance, living room, 2 double bedrooms, kitchen, and large bathroom. city tax to add to the price, €2.5 per person per night.

Top guest favorite

A traditional Tuscan villa is captured from an exterior view, showcasing its stone facade and arched doorways. Lush greenery surrounds the property, with well-maintained gardens and planters. The scene is complemented by a clear blue sky, adding to the serene countryside atmosphere.

Home in Barberino Tavarnelle

4.97 out of 5 average rating, 72 reviews

Podere Tignano, 4-bedroom villa in the Chianti!

Podere Tignano is located on the gentle green hills of Chianti between Florence and Siena, Podere Tignano enjoys stunning views of the countryside surrounding with grain fields, vineyards and olive groves. The villa has been restored preserving the original characteristics of its Tuscan stone structure harmoniously divided in two levels. The villa is 180 square meters and can accommodate 8 persons in 4 bedrooms with 3 bathrooms. Private pool for the exclusive use of the guests.

Top guest favorite

A spacious lawn gently slopes up towards a beautifully restored two-level house, featuring warm yellow and red hues. Tall cypress trees line the property, complementing the lush greenery of the surrounding gardens. Soft clouds drift above, enhancing the serene countryside setting.

Home in Gambassi Terme

4.99 out of 5 average rating, 178 reviews

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.

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Aerial view of the villa complex surrounded by lush greenery and olive groves. A spacious pool is centrally located, with well-maintained lawns and trees framing the property. Rolling hills and a clear sky are visible in the distance, enhancing the tranquil countryside setting.

Villa in Rignano sull'Arno

4.95 out of 5 average rating, 138 reviews

Tuscan Dream Villa @ Rustic Elegance Near Florence

🌿Welcome to Villa La Conigliera🌿, an ideal retreat for a romantic getaway or a relaxing stay, just a few kilometers from Florence. 🌟Set in the peaceful Tuscan countryside, overlooking an ancient courtyard, it blends rustic charm with modern comfort. Perfect for couples or families with a newborn, with a crib available upon request 👶. Two adjacent villas for 4 and 6 guests complete the hamlet. 🚗 A car/motorbike is recommended for exploring the beautiful surroundings.

Top guest favorite

Villa in San Casciano

4.97 out of 5 average rating, 110 reviews

Luxury Villa in the very heart of Chianti

The views, the views, oh my word the VIEWS! Originating in the early 12th century this spectacular home once served as the bakery for the entire village. Now fully renovated, the entrance and ground level have been opened with glass arches allowing natural light to illuminate the exposed walls, 4 large bedrooms, 3 with ensuite baths ( including a jacuzzi ). Only Minutes away from the famous Wineries of Chianti, this is THE Spot for a glass amongst friends.

Guest favorite

A historic villa is situated amidst lush, rolling hills, surrounded by vineyards. The exterior features a traditional stone facade, large windows, and terracotta roof tiles. Manicured gardens with circular patterns enhance the property's charm, complemented by tall cypress trees framing the serene landscape.

Apartment in Castelnuovo Berardenga

4.93 out of 5 average rating, 161 reviews

Villa di Geggiano - Perellino Suite

The 700 years old Villa di Geggiano, surrounded by our working vineyard and lovingly maintained gardens, is located in Chianti in Tuscany which is one of the most beautiful regions of Italy. Our guesthouse is located in one of the original garden pavilions of the villa. PLEASE NOTE THAT WE ARE IN THE COUNTRYSIDE WITH VERY FEW PUBLIC TRANSPORT OTHER THAN TAXI SO THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A RENTAL CAR.

Top guest favorite

A view is provided from a window overlooking a narrow street in a historic area. A stone well is visible at the center of the square, surrounded by rustic buildings. The scenery includes distant hills, enhancing the sense of tranquility in the surroundings.

Condo in Gambassi Terme

4.99 out of 5 average rating, 100 reviews

CASA NELLA Apartment in the Historic Center

The recently renovated apartment is located in the historic center of the village in a central and quiet area. On the second floor of a historic building. It consists of a large and bright living room with two windows overlooking the picturesque square of the cistern with a kitchenette also equipped with a dishwasher, a spacious double bedroom with a bathroom with shower and bidet. Kitchen equipment, linens, towels and bath towels are available for guests.

Guest favorite

A covered outdoor seating area is framed by arches, offering views of lush greenery and trees. Two light-colored chairs are positioned around a small table, while potted plants add a touch of color to the serene environment.

Home in Montaione

4.94 out of 5 average rating, 105 reviews

Cercis - La Palmierina

E' un appartamento facente parte di una tenuta completamente recintata di 60 ettari di natura incontaminata: più di 1000 ulivi, innumerevoli cipressi e foreste profumate creano un ambiente idilliaco per coloro che ricercano tranquillità e silenzi. La tenuta Palmierina è in prossimità di Castelfalfi (un vero gioiello di architettura medievale) e nelle vicinanze di Firenze (50 Km), Siena (50 Km), Pisa (50 Km). Nelle vicinanze ci sono due campi da golf.

Top guest favorite

A freestanding, oval-shaped bathtub is filled with water, adorned with floating candles and flowers. Two small wooden side tables hold toiletries and spa essentials. A woven rug lies on the floor alongside a pair of slippers, adding texture to the space.

Home in Fiesole

5 out of 5 average rating, 245 reviews

"La limonaia" - Romantic Suite

Romantic Suite immersed in the enchanting hills of Fiesole. It is the ideal place fot those looking for unique and exclusive experience of its kind characterized by suggestive views and unforgettable sunsets. The accommodation is part of an old 19th century Tuscan farmhouse surrounded by its own olive groves and woods. This is an ideal place for a relaxing holiday and privileged base for visiting the major centers of interest in Tuscany.

Guest favorite

A charming terrace offers a view of the surrounding greenery, framed by an archway. A wooden table rests on the space, accompanied by a bench. Potted plants add a touch of vibrancy, while the sunlight enhances the inviting atmosphere of the outdoor setting.

Condo in Gambassi Terme

4.89 out of 5 average rating, 234 reviews

A View Over Tuscany's Countryside

A quite and peaceful apartment in the middle of Tuscany countryside, ideal for 3 people also, is about 60 squares meters with bath , double bed , living room with a sofa' bed, kitchen and a beautiful terrace overlooking the vineyards.There is, also, a private parking inside the condominium and a nice bar near by. It is located near the main tourist attractions, this apartment is ideal for travelers who wants to explore Tuscany.

Guest favorite

Villa in Gambassi Terme

5 out of 5 average rating, 6 reviews

Villa Oliva w/pool+ ensuite - Pillo Holiday Villas

Welcome to VILLA OLIVA, a beautiful structure equipped with every comfort and an amazing swimming pool for exclusive use ready to brighten your summer days, between visiting a famous city and a stop in one of the many cellars located in Tuscany. Here you will feel at home, with large outdoor spaces where you can relax, play sports or go for a walk without forgetting the comfort of the 5 bedrooms each with a private bathroom!

Guest favorite

A spacious green garden is visible, dotted with trees offering natural shade. A wooden dining table with chairs is positioned under the trees, providing an inviting setting for outdoor meals. The rustic brick building stands in the background, complementing the serene surroundings.

Farm stay in Simignano

4.89 out of 5 average rating, 198 reviews

Casa al Gianni - Capanna

Hi, we're Cristina & Carmelo! We invite you to live an authentic experience in our farmhouse “Casa al Gianni” located 20 minutes from Siena. Our hallmark is simple life in close contact with nature and the animals of our farm. Immersed in the woods and the beautiful Tuscan countryside, you will spend an unforgettable vacation. This slice of paradise will remain in your heart!