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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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Top guest favourite
Home
4.99 out of 5 average rating, 97 reviews

Relaxation and charm in the Chianti hills

Beautiful stone farmhouse, detached, surrounded by olive trees and the Chianti hills, with private garden and panoramic swimming pool. Ground floor with large living rooms, antique fireplace and wood-burning oven, bright living room and fully equipped kitchen. On the first floor, three suites consisting of a bedroom, study and private bathroom. Access via gate and white road on private property just 500 meters from the village of Strada in Chianti. Ideal for peace and relaxation. Convenient location for visiting Tuscany.

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
5 out of 5 average rating, 315 reviews

Podere Vergianoni nestled in Chianti with a pool

Podere Vergianoni is an ancient and authentic farmhouse dating back to the 17th century located in the beautiful hills of Chianti in Tuscany. The apartment is impeccably furnished in the traditional local style of old Tuscany: ancient wooden beams, terracotta floors, and unique furniture. In the large outdoor courtyard, you'll find a large swimming pool on a panoramic terrace at your disposal, overlooking the valley with breathtaking views of vineyards and olive groves, where you can enjoy spectacular sunsets.

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
A traditional stone house with a sloped roof features wooden shutters and a central door. An awning provides shade over a dining table set on a well-maintained lawn. Surrounding flowers and greenery create a peaceful outdoor setting, reflecting a serene countryside ambiance.
Home
5 out of 5 average rating, 67 reviews

Romantic Tuscan Retreat • Pool&Views

A peaceful Tuscan retreat surrounded by vineyards and rolling hills. Perfect for couples seeking privacy, views and authentic Chianti charm. Enjoy the pool, outdoor dining and unforgettable sunsets. 1-Bedroom-House ca. 70 squared meters Entrance through Terrace in Living / Bed Room, through partition wall. Sectioned Bedroom with Double bed (1,60 m wide). Through an open round arch you get in the kitchen with dining area. Shower and Wc. Built in traditional Tuscan Style with modern flair.

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
An inviting kitchen space is highlighted by an arched brick entry. A large wooden dining table is set in the foreground, adorned with a decorative centerpiece. The kitchen features modern appliances, including a silver refrigerator, and warm lighting enhances the rustic ambiance.
Villa
4.94 out of 5 average rating, 122 reviews

Tuscany Country House Villa Claudia

Vivi l’incanto della nostra Country House: un antico casale toscano di pregio, finemente restaurato, con vista mozzafiato sul borgo di Canneto (785 d.C.). Immersa nel verde di San Miniato e dotata di ogni lusso moderno, la villa è un rifugio esclusivo per rigenerarsi. Scegli tra il relax totale nella Jacuzzi in giardino, tour enogastronomici d'eccellenza o visite alle vicine città d’arte toscane. Un’esperienza sensoriale indimenticabile tra storia e natura. Prenota il tuo sogno in Toscana!

Top guest favourite
An outdoor dining area is illuminated softly by warm lights, surrounded by lush greenery and climbing roses. A stone patio features a table set for guests, with several chairs positioned nearby, creating an inviting space for al-fresco meals.
Cottage
4.96 out of 5 average rating, 107 reviews

Tuscan cottage, sea view and private olive garden

Metato26 is a unique, newly renovated residence blending traditional Tuscan soul with contemporary comfort. High-speed internet facilitates remote working in silence. Ideal for multigenerational privacy, we include a complimentary pasta class and local insight. Outside: a 200sqm garden with wisteria and rose pergolas, a jacuzzi, and a fenced 600sqm sea-view olive grove. Pet-friendly and authentic, moments from the Italian Riviera and the art cities of Tuscany. This is the real thing.

Guest favourite
A tranquil outdoor area features a private swimming pool surrounded by lush greenery. The rustic stone building is visible in the background, nestled among trees. A well-maintained garden area is present, blending harmoniously with the natural landscape.
Home
4.92 out of 5 average rating, 26 reviews

Ancient mill in the "green hearth" of Tuscany

This ancient mill, in the past one of the most important of Garfagnana, has been carefully restored preserving its peculiarities that make it a place full of history and traditions. Perfect for a relaxing holiday in a unique place, with a surreal atmosphere and far from the everyday reality. The town of Pieve Fosciana and the medieval village of Sillico can be reached within a few minutes by car. Consisting of 2 buildings, it has a swimming pool and private parking.

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
Villa
4.92 out of 5 average rating, 13 reviews

Villa Amore, a Romantic Hilltop Farmhouse in Lucca

Nestled atop the enchanting hills of Tuscany, a mere 8-minute drive from the historic Lucca city centre, lies a haven of romance and elegance - Villa Amore, a hilltop Farmhouse. This idyllic retreat seamlessly blends rustic charm with sophisticated style, offering an unparalleled escape for those seeking the perfect blend of tranquillity and luxury.<br><br>Step into a world of timeless beauty as you enter this tastefully appointed farmhouse.

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.

Top guest favourite
A rustic stone villa is framed by greenery and features a terrace with outdoor seating. Flower pots line the garden area, showcasing vibrant blooms. In the background, the structure's windows and shaded patio create a welcoming ambiance under the clear blue sky.
Home
5 out of 5 average rating, 99 reviews

Coppori Estate Dependance

Extremely cozy dependance of a 1400 villa on Lucca's hills, deep inside the tuscany countryside, with access to the private swimming pool and garden which includes a pretty tiny lake populated by fish. Graziosa dependance di un rustico del 1400, situato sulle colline lucchesi, immerso nel verde della campagna toscana, con accesso alla piscina privata della proprietà ed al parco che include un piccolo laghetto con pesci.

Popular amenities for Sant'Annapelago holiday rentals

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