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Holiday rentals in Poggiolino

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Top-rated holiday rentals in Poggiolino

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

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Guest favourite
The villa features a classic facade adorned with climbing plants, framed by lush greenery. A gravel pathway leads to the entrance, complemented by stone steps. The surroundings create a serene rural atmosphere, inviting visitors to explore the expansive outdoor area.
Villa
5 out of 5 average rating, 12 reviews

The Castellaccio of Figline 2

The accommodation is located on the GROUND FLOOR of a villa surrounded by greenery called "Il Castellaccio", which owes its name to the proximity to the ruins of the old castle that belonged to the Uberti family. The house enjoys a magnificent view of the surrounding countryside and is ideal for a relaxing holiday for families or groups of friends, with the possibility of visiting cities of art and enjoying the beautiful landscapes of Chianti, as well as the food and wine specialties of the area.

Top guest favourite
Townhouse
4.89 out of 5 average rating, 333 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

Guest favourite
Holiday home
5 out of 5 average rating, 9 reviews

La Chiocciola Tuscany Apartment

Prenditela con calma in questo spazio unico e rilassante. Situato in un complesso residenziale immerso nel verde, l'appartamento è in posizione strategica per poter visitare le principali città d'arte toscane e la campagna del Chianti. A poca distanza a piedi da vari supermercati, dista pochi minuti di macchina dalla stazione ferroviaria e dal casello autostradale. Godetevi il vostro tempo nel calore di un monolocale in stile toscano con spazio esterno privato tutto a vostra disposizione!

Top guest favourite
The panoramic swimming pool is surrounded by a spacious patio and offers stunning views of the lush Tuscan hills. Sun loungers are placed nearby, providing a comfortable area for relaxation under the clear blue sky.
Villa
5 out of 5 average rating, 31 reviews

Mathis House Best View in Chianti, Exclusive Pool

Mathis House is the ideal place for your family vacation and to discover the beauty of the Tuscan countryside. Overlooking where the Chianti hills descend placidly towards the Arno valley, it's just 30 minutes by car or 20 minutes by train to Florence city center. Enjoy a peaceful and private stay with breathtaking views, luxurious design, a panoramic swimming pool, private parking with automatic gate, and air conditioning in every room and living area. Welcome to your Tuscan paradise.

Top guest favourite
The exterior of the castle is showcased at sunset, with vibrant orange and purple skies providing a dramatic backdrop. Stone towers rise from the landscape, surrounded by greenery and colorful flora, reflecting the historic charm of the property.
Castle
4.99 out of 5 average rating, 222 reviews

The Castle of Ferrano - Castle in Tuscany

Try the experience of staying in a real Castle! Il Castello di Ferrano offers to its hosts the chance of living an unforgettable experience: you will be the only guests in the castle, and everything will be for you (private pool from June to September, gardens etc..). Historical building, surrounded by nature, finely decorated, frescoes/moulding on the ceiling, ample terrace w/ stone and terracotta floor, private outdoor pool.. Good position. Preferably come by car.

Top guest favourite
A charming stone building surrounded by lush greenery features a wooden terrace with a parasol and flower pots. Two loungers are placed on the well-maintained lawn, providing a relaxing outdoor space.
Farm stay
4.99 out of 5 average rating, 475 reviews

Old hayloft on the Chianti hills

Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, overlooking the Chianti valleys and enjoying splendid views of the surrounding hills and the city of Florence. The apartment is completely independent, on two internally connected floors, and features a private garden lined with centuries-old oaks and Tuscan cypresses. The restoration maintained the original Tuscan architectural style of rural barns.

Top guest favourite
The historic tower-penthouse villa is surrounded by lush greenery and trees. The three-story structure is characterized by its earthy facade and wooden shutters. Well-maintained gardens with various plants create a serene outdoor environment, enhancing the villa's tranquil charm and historical significance.
Castle
4.96 out of 5 average rating, 136 reviews

Tower Penthouse in small castle near Florence

900 year old tower-penthouse apartment in Chianti Villa, spacious & super-scenic historical home that combines magical atmosphere with space, light, character, convenience. Painting-like 360° views of Tuscan Hills all the way to Florence; sun-filled, private grounds. Perfect location for an unforgettable family stay. Ample private property (including forest). Walking distance from village shops. Convenient location, Florence in sight.

Superhost
Holiday home
4.87 out of 5 average rating, 209 reviews

Barrel Suite Tuscany • Hot Tub • Vineyard View

Sleep inside a wine barrel in Tuscany — one of the largest in the world (3.5 m × 8 m) — nestled in an olive grove in Reggello, with panoramic views over the hills and vineyard. Private bathroom, kitchenette, veranda, private courtyard and exclusive hot tub: everything for a total escape from the world. 40 min from Florence, with Siena, Arezzo, The Mall Luxury Outlet and Vallombrosa all within easy reach. Free private parking included.

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, 312 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
Holiday home
4.89 out of 5 average rating, 315 reviews

[Authentic StoneHouse]Jacuzzi & Viewpool Apartment

Nestled in a medieval village in the heart of Chianti, this exclusive historical apartment blends Tuscan charm with refined contemporary design. Enjoy a panoramic pool overlooking the hills, multiple terraces, and a unique hot tub Jacuzzi suite and bathroom carved in travertine. Designed for two, it’s the perfect place to slow down, reconnect, and experience Tuscany in total peace.

Top guest favourite
The stone cottage is set amidst lush greenery, featuring a sloped roof and a large glass door that opens onto a sunlit terrace. Sun loungers are positioned nearby, surrounded by flowering plants, with olive trees visible in the background against a clear blue sky.
Farm stay
4.92 out of 5 average rating, 368 reviews

Chianti La Pruneta, Raphael Apartment

Stunning apartment in the heart of Tuscany set in the middle of vines and olives trees. The apartment has been totally refurbished keeping the lovely old features, beamed ceilings, marble floors with antique furniture. Patio doors lead to a private terrace with sun loungers for relaxing and space. With table and chairs you can eat 'Al fresco' enjoying the beautiful views.

Top guest favourite
A spacious living area features a modern design, with a prominent stone fireplace and minimalist furniture. Large glass doors open to a serene outdoor view, while natural light brightens the room, highlighting the soft tones of the walls and furnishings.
Tower
4.95 out of 5 average rating, 214 reviews

A Big Dream in a Little Tower.

The Tower was created in the late 1800s by an illustrious Englishman, Sir John Temple Leader, in one of the oldest and most important stone quarries belonging to the Medici family. From the same quarry were extracted many important works such as the columns of the Medici chapels, the steps of the Laurenziana library .. all just 5 km from the historic center of Florence.

Popular amenities for Poggiolino holiday rentals