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Holiday rentals in Pillo

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Top-rated holiday rentals in Pillo

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Top guest favourite
Villa in Montaione
4.98 out of 5 average rating, 50 reviews

Private Villa with semi-Olympic pool and Tennis

On the ground floor there is a large eat-in kitchen which is very well and functionally equipped with dishwasher, oven, microwave, toaster, kettle, etc. , annexed pantry. The window of the kitchen over the sinks opens into a marvelous Tuscan panorama. Next to the kitchen there is the laundry, with the 2 washing machines and iron equipment. The laundry is shared with the property during your stay. On the other side, still next to the kitchen, there is a dining room with a 10 seats wooden table. Then, there is a large living room with 3 comfortable sofas and there is a sit in fireplace. Due to security reasons the fireplace cannot be used. Totally there are 4 bedrooms: 3 with kings size beds on the first floor and 1 with twin beds on the ground floor. 2 rooms have air conditioning , the remaining 2 have a portable fan. 2 rooms are with en-suite bathrooms with WC, bidet and shower, 1 bathroom with WC, bidet and shower and 1 bathroom with WC. Fresh linen, towels and pool towels are provided weekly. Change of linen and towels for any extra week at € 100. The villa is furnished as a home and the dining and sitting room of the villa are furnished with beautiful antiques and paintings and have old terracotta tiles. So you will not get the feeling of staying in a rented accommodation. Upon prior request we can arrange for 2 extra beds for babies. Outside the villa there is a nice garden with hedges and roses and a beautiful old lime tree under which guests will love to eat their breakfast or dine. In front of the garden there is an ancient and renovated chapel where, once a year, a Mess in memory of the owner's parents is celebrated. Cleaning services are available upon request, also we will bring you the hot dinner (or lunch) when you prefer (even on the day of your arrival) proposing delicious typical Tuscan dishes. Car is needed. We live nearby and are willing to offer you any help you may need. On the top of the nearby hill, 5 minutes walk from the villa, there is the private semi-Olympic pool 25x12.5 m, a pool house with bathroom, changing room, shower, kitchen, dining room, panoramic veranda for relaxing or alfresco dining and a built-in barbecue. Here you can spend most of the time of your vacation as it is a breathless location where you would admire a 360° idyllic typical Tuscan landscape! Just near the private pool, there is a green tennis court for the sole use of guests and a wide lawn where guests can exercise or relax. The pool will be the greatest attraction for all the guests; it will be open June, July, August, September, please ask for May. There is no fence and no surveillance, so children must be supervised at all times as it is up to 4 meter deep in the part of the springboards. In any case guests ' use of the swimming pool is at their own risk. The guests will enjoy their days with long stays at the pool since the pool house provides all comforts of a home. Here you can lean, rest, swim, run, cook, eat, read and appreciate the marvelous surrounding panorama. There are sun loungers, couches, armchairs and tables and a ping pong table. The main attraction of this place is its exclusivity and the possibility to practice sport, i.e. swimming, tennis, ping pong, gym in open lawns or in the large space between the pool and the pool house, soccer. The tennis court can be used anytime. Portable wifi hotspot available at the villa and at the pool and pool house. Notes on prices: Prices for the property (9 sleeps) are meant per day/Euro. They include: villa, private pool and pool house, private tennis, electricity, gas, water, use of the washing machine, firewood, linen, towels, parking Not included: Stay tax € 1.00 per person per day (per max 6 days) for persons over 14 years of age is to be paid directly at arrival. Change of linen and towels for any extra week at € 100, is to be paid directly at arrival. We accept small dogs upon prior agreement and for their stay we ask a contribution of € 10 per day. Check in is from 16.00 to 19.00; late arrivals are possible but we need to be informed in time and they may be charged. Notes: You will be responsible for any damage to the rental property that is caused by you or your party during your stay.

Top guest favourite
Apartment in Gambassi Terme
4.99 out of 5 average rating, 127 reviews

Cosy Tuscan Home near Florence & San Gimignano

A WELCOMING NEST where tradition and modern comfort meet. Perfect for those who want to slow down, relax, and experience the most authentic Tuscany, far from the hustle and bustle. Imagine waking up in the heart of a Tuscan village, looking out onto the square, and starting the day with the tranquility and rhythms of the local life. The apartment, completely renovated and tastefully furnished, is located in the historic center of Gambassi Terme, a strategic point for exploring the wonders of Tuscany.

Guest favourite
Townhouse in Scandicci
4.88 out of 5 average rating, 338 reviews

Florence Sunset Hills • Giogoli

Escape to the peaceful hills of Giogoli where authentic Tuscan charm meets breathtaking views of Florence.Just 15 minutes from the city center and the Chianti countryside, this elegant home is the perfect base for exploring Tuscany while enjoying quiet mornings, unforgettable sunsets, and the beauty of the surrounding landscape. Surrounded by nature but close to the region's most iconic spots, it's the ideal retreat for anyone looking for comfort, tranquility, and a genuinely Tuscan experience

Top guest favourite
Home in Montespertoli
5.0 out of 5 average rating, 23 reviews

Villa la scuderia quiet luxury private garden pool

Once a 19th-century horse stable, this Tuscan home was discovered by my mother : a Dutch artist and traveller, she moved here in search of beauty, nature and light. She stayed for twenty years. My brother and my daughter grew up running barefoot on these ancient terracotta floors. Even today I still fall in love with the light that enters through the old arches and reflects into the house and the flower-filled private garden.its not an hotel is a lifetime experience, welcome to” La scuderia “.

Guest favourite
Holiday home in San Gimignano
4.95 out of 5 average rating, 91 reviews

Tuscan House with Private Jacuzzi in Chianti

An oasis of peace in the heart of Tuscany, along the wine route! - Exclusive Jacuzzi in your own private garden - Strategic location between the medieval towns of Certaldo, San Gimignano, Siena, and Florence - A 700 sqm private garden filled with the sweet sound of birds singing - A newly renovated home where history meets modern comfort and unique design - The warmth of a wood-burning fireplace to heat your beautiful winter dreams - The perfect place to regenerate and completely unplug

Top guest favourite
An aerial view captures Podere Vergianoni nestled in the Chianti hills, surrounded by lush vineyards. The property features a clear blue pool, shaded terraces, and carefully landscaped gardens. Rolling hills and rows of grapevines create a serene backdrop, highlighting the natural beauty of the Tuscan countryside.
Apartment in Noce
5.0 out of 5 average rating, 350 reviews

Podere Vergianoni nestled in Chianti with a pool

Podere Vergianoni is a family-run, historic property dating back to the 1600s, located in the beautiful hills of Chianti in Tuscany. Our family can arrange a private shuttle and local experiences directly. The apartment is available for 2 adults with the option of adding a sofa bed for 2 children under 12 years of age. In the large outdoor courtyard you'll find a saltwater pool with a relaxation area on a panoramic terrace overlooking the castle and vineyards with unique sunsets.

Guest favourite
A private swimming pool is surrounded by lounge chairs, offering a relaxing space. Umbrellas provide shade, and lush greenery frames the area. The villa, with its rustic architecture, stands in the background against a clear blue sky, enhancing the serene outdoor setting.
Villa in Montaione
4.98 out of 5 average rating, 51 reviews

Exclusive villa Lionella with private pool

Villa Lionella is an exclusive residence within 2 hectares of private park with swimming pool and independent entrance and private parking. It consists of a large living room with fireplace, dining room, kitchen with second fireplace, library with sofa bed. Upstairs 5 bedrooms with 3 bathrooms. In the basement billiard room, poker table, fitness area with sauna. Equipped with air conditioning, WiFi, linen and private pool. The villa is for the exclusive use of those who book it only

Top guest favourite
An aerial view of the property reveals a charming red house surrounded by lush greenery. Tall cypress trees and vibrant bushes create a tranquil landscape, while an expansive lawn features relaxing loungers, inviting guests to enjoy the serene atmosphere of the Tuscan countryside.
Home in Gambassi Terme
5.0 out of 5 average rating, 230 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.

Guest favourite
A private swimming pool is framed by manicured lawn and positioned under two large umbrellas. Four lounge chairs are arranged around the pool, offering views of rolling hills and the Tuscan countryside beyond. The pool features a sleek, modern design with clear water reflecting the sky.
Villa in Gambassi Terme
4.96 out of 5 average rating, 72 reviews

Villa Via Francigena

Splendid recently renovated villa on Tuscan hills. Arranged on three floors for a total of 240 m2, surrounded by a private garden of 2000 square meters fenced and illuminated. Private swimming pool (6mt * 12mt h1.30mt) with shower and patio for outdoor lunches and dinners and barbecues. Free Wi-Fi in every room and air conditioning. Pets Allowed. 2 covered indoor parking spaces with automatic gate. Electricity (0.40€/Kwh) and water (2€/m3) consumption not included in the price.

Top guest favourite
A large swimming pool surrounded by a brick patio and manicured lawns is highlighted in this image. Sun loungers are positioned along the pool's edge, with lush greenery and trees creating a serene backdrop. The villa's charming structure is visible in the distance under a partly cloudy sky.
Villa in Barberino Tavarnelle
4.98 out of 5 average rating, 105 reviews

Podere Tignano, 4-bedroom villa in the Chianti!

Nestled among the rolling hills of Chianti between Florence and Siena, Podere Tignano offers breathtaking views over vineyards, olive groves, and golden grain fields. This charming Tuscan stone villa blends authentic rural character with modern comfort and welcomes up to 8 guests in 4 bedrooms. Surrounded by peaceful countryside and featuring a private swimming pool, it is the perfect retreat for those seeking relaxation, nature, and the true spirit of Tuscany.

Guest favourite
A modern swimming pool is surrounded by a neatly manicured lawn and vibrant flower beds. Sun loungers are positioned beside the pool, while a shaded area is provided by an umbrella. The villa features a terracotta roof, with inviting outdoor spaces visible in the background.
Villa in Gambassi Terme
4.93 out of 5 average rating, 14 reviews

La Capannina Di Pillo

Ground floor: entrance, kitchen (6 burners, fridge freezer, oven, dishwasher, coffee machine, toaster, microwave oven), dining room, living room with fireplace, satellite TV with access to the external loggia equipped for outdoor lunches and dinners, bathroom with shower. Lower floor: a large bedroom with double bed and a double sofa bed with bathroom with shower; air conditioning. First floor: 2 double bedrooms with air conditioning, 1 bathroom with shower

Guest favourite
The image presents an aerial view of a rustic villa surrounded by rolling hills and vineyards. A rectangular swimming pool is situated in the foreground, and the greenery of the surrounding gardens enhances the serene landscape. The property showcases traditional architecture with terracotta roofs.
Flat in San Gimignano
4.81 out of 5 average rating, 64 reviews

Il Castro Luxury San Gimignano. Michelangelo Suite

Il Castro is a group of apartments finely recovered from a careful renovation, which has left the signs of the past unchanged. The classic furnishings, meticulously decorated by local artisans, blend in perfect harmony with elements of fine design, giving a minimalist and refined effect. The finishes of the bathrooms are extraordinary, where the search for detail and the quality of the materials transform the environment into something unique.

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