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Holiday rentals in Sant'Annapelago

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Top-rated holiday rentals in Sant'Annapelago

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

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Guest favourite
The stone farmhouse is surrounded by lush greenery and tall cypress trees, with a gentle slope leading to the entrance. A shaded terrace is visible in front, offering a place to relax and enjoy the outdoor setting. The sky is partly cloudy, enhancing the tranquil ambiance.
Farm stay
4.91 out of 5 average rating, 117 reviews

Piccionaia apartment with garden for 2 people

In Montespertoli, among the rolling hills of Chianti, there is Podere Paglieri, a small family-run farm where wine and oil have been produced for generations. We are located halfway between Florence and Siena, in a perfect position to discover San Giminiano, Volterra, Siena, Lucca, and the Tyrrhenian coast, which are just a few kilometers away. The farm is surrounded by vineyards, olive groves and woods where you can walk freely, has a large and well-kept garden and a beautiful shaded terrace.

Guest favourite
The stone exterior of the house is framed by lush greenery and flowering plants. A covered entryway is visible, with a chair placed alongside. Large windows allow natural light to fill the interior, while the surrounding landscape features mountains in the background.
Villa
4.91 out of 5 average rating, 47 reviews

Villa Buriconti - Peaceful Countryside Retreat

Villa Buriconti is nestled in the Tuscan countryside, surrounded by woods that offer peace and privacy. From the house, enjoy open views of the valley and mountains, with the Apuan Alps on one side and the Apennines on the other. It has an authentic charm, with historic furnishings and details that tell the story of this land’s tradition. It’s the perfect retreat for those seeking tranquility, a connection with nature, and moments of peace. Here, time slows down, surrounded by nature and calm.

Top guest favourite
A stone structure with a tiled roof is framed by greenery, surrounded by rolling hills. A spacious outdoor area features a wooden table, inviting relaxation. Large trees and thriving shrubs enhance the tranquil setting, with a backdrop of a serene sunset illuminating the landscape.
Home
4.98 out of 5 average rating, 222 reviews

The Chianti Classico Sunset

Se cercate una location idilliaca nel cuore del Chianti classico, immersi nei vigneti e oliveti delle splendide colline toscane, nel podere di una Villa storica del ‘500, allora venite nel nostro fienile!! Ha una posizione dominante con una vista strepitosa, dove è possibile godersi tramonti mozzafiato. La totale indipendenza della casa, l'accogliente giardino, il grande loggiato permettono di trascorrere soggiorni in totale tranquillità. Le nostre recensioni sono la vostra migliore garanzia.

Top guest favourite
An inviting swimming pool is bordered by lush greenery, with sun loungers and a shaded seating area nearby. The elegant villa stands in the background, featuring large windows and a traditional design, surrounded by tall cypress trees against a clear blue sky.
Villa
5 out of 5 average rating, 31 reviews

Villa Montefalcone: Charm, Private Pool, and Chef

Sfuggi alla routine quotidiana e immergiti nel lusso di Villa Montefalcone, un gioiello nascosto nelle colline di Lucca. Qui, nel cuore pulsante della Toscana, potrai creare ricordi indimenticabili insieme ai tuoi cari. Lasciati sedurre dall'eleganza dell'architettura Liberty e dai giardini rigogliosi che abbracciano la villa, un connubio perfetto di storia e modernità. Rilassati a bordo piscina e goditi la nostra cucina esterna completamente attrezzata, perfetta per serate festose o intime.

Top guest favourite
Villa
4.98 out of 5 average rating, 88 reviews

Tuscany Villa in Lucca With Private Infinity Pool

Experience the charm of Villa Herb & Stone, a beautifully restored stone farmhouse featuring an award-winning infinity saltwater pool, a vineyard, interiors styled by London-based designers, and strong Wi-Fi. Set in the wild beauty of Tuscany’s Garfagnana region, it’s the perfect base to explore Barga, Lucca, and Florence. Enjoy curated experiences like wine tastings, organic catering, pizza classes, and massages. Every detail is crafted for relaxation, culture, and a connection to Tuscany.

Top guest favourite
The exterior of the cottage is surrounded by greenery, featuring a sunlit terrace with a dining table and umbrella. Potted plants add color to the entrance, while the rustic charm of the stone and tiled details enhances the natural setting.
Home
4.99 out of 5 average rating, 259 reviews

Tuscan cottages in an ancient villa with a garden

The Cottage is part of a property owned by the Bernocchi family, which was already on maps of the area in the 1500s and is located right on an ancient Roman road that crossed the Calvana Mountains. About 9 km from Prato and 20 km from Florence. The Cottage, open on three sides, is situated in a panoramic position surrounded by a private park, ideal for walking and sports. A real home fitted with kitchen, living room, bedroom and bathroom. Large outdoor spaces, garden, and botanical garden.

Top guest favourite
Two individuals are seated in comfortable chairs on a wooden deck, enjoying a serene moment as the sun sets. A bottle of wine and two glasses are placed on a small table nearby, surrounded by lush greenery and vibrant flowers.
Home
4.99 out of 5 average rating, 70 reviews

Relaxation and comfort in the hills of Florence

Apartment in a typical Tuscan stone farmhouse: measuring 160 square meters, it is finished with typical Tuscan materials, pietra serena and terracotta. It consists of a large living room at the entrance, dining room, kitchen, 2 bathrooms, storage room, 3 bedrooms, and a study area. Arranged in an east-west position thanks to a large terrace, a patio and a large private garden, it allows you to enjoy the sunrise for your breakfast and the sunset for a pleasant aperitif.

Guest favourite
An outdoor terrace is showcased, featuring a dining table set for meals under a draped canopy. String lights illuminate the space as the sun sets, casting a warm glow over the surrounding hills. Potted plants enhance the inviting ambiance.
Apartment
4.94 out of 5 average rating, 104 reviews

Golden View Attico in the heart of Tuscany

In the heart of Tuscany you will find a romantic dream hidden in the quaint village of Barga with all the comforts of home. You can dine on the splendid terrace surrounded by a magical view, eat good food and enjoy the “Dolce far niente" as the Italians do. Whether business or pleasure you Will be under a spell that Will keep you coming back for more. I invite you to transend to a place and time where the land Is Rich with authenticity . . . Welcome to my home

Top guest favourite
Farm stay
4.98 out of 5 average rating, 164 reviews

Romantic stay where Tuscany meets the sky!

The property is located on top of a very panoramic hill, near the medieval village of Sillico where is located also a very good restaurant. Perfect accommodation for romantic couples, families with children with their dogs. Perfect place to relax but also suitable for guests who like active holiday with many exiting trekking, canyoning, mtb and horse riding excursions. Nice panoramic pool and view on the entire valley. Welcome where Tuscany meets the sky!

Guest favourite
A spacious freestanding bathtub is filled with water, adorned with floating flowers and candles. A small wooden table beside it holds a bucket of champagne and two glasses. Soft towels and a decorative rose are also visible, contributing to a relaxing ambiance.
Home
4.99 out of 5 average rating, 286 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 favourite
A cozy living area features a plush sofa adorned with decorative cushions. Natural light enters through large glass doors that open to a garden view. A stone fireplace adds a classic touch, while decorative plants and flowers create a serene atmosphere.
Flat
4.84 out of 5 average rating, 32 reviews

Luxury Apartment with Private Garden inside Lucca

Move seamlessly from inside to out, enjoying the antique garden views from numerous vantage points. On nights in, bring in a private chef to show off a menu of local favorites to be served directly in your private garden. The air conditioning will make sure the apartment is fresh and ready for an unforgettable night.

Guest favourite
Home
4.98 out of 5 average rating, 41 reviews

La Veduta. Villa with private pool in Tuscany

Welcome to this charming villa, perfectly located in the Tuscan hills above Pescia. With its unique panoramic views and peaceful location, this villa offers a peaceful escape from everyday life. Here you can enjoy complete peace and tranquility in a scenic setting.

Popular amenities for Sant'Annapelago holiday rentals

  1. Airbnb
  2. Italy
  3. Emilia-Romagna
  4. Sant'Annapelago