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Vacation rentals in Montaione

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Top-rated vacation rentals in Montaione

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Top guest favorite
An aerial view captures the sprawling vineyards and olive groves surrounding Podere Vergianoni. The property features a salt-water pool positioned on a terrace, offering panoramic views of the lush Chianti landscape and medieval castle in the distance. Rustic buildings line the garden area.
Condo in Noce
5 out of 5 average rating, 205 reviews

Ancient 17th-century farm in Chianti, Tuscany

Podere Vergianoni is an ancient and historic property dating back to the 1600s, located in the beautiful hills of Chianti in Tuscany, with the possibility of organizing exclusive services and experiences tailored to you. The apartment is available for 2 adults with the possibility of adding a sofa bed for 2 children under 12 years of age. In the large outdoor courtyard you'll find a saltwater swimming pool with a relaxation area on a panoramic terrace, with wonderful views of the castle, hills, and vineyards and breathtaking sunsets.

Top guest favorite
Home in Montaione
4.98 out of 5 average rating, 50 reviews

Private Tuscany Villa with jacuzzi | Casa Bonelli

'Fienile Toscano' covered with bricks and stones, completely independent, with a broad garden and a Jacuzzi whirlpool bath, for the sole use of our guests. Ideal for people who love relax, nature, (or need silence to work) and as a starting point for day trips. Florence, Siena, Lucca, Volterra, San Gimignano and other less known gems are within an hour travel. The sea is an hour and 20 minutes far. The minimum stay is 3 nights, while the maximum is 30 nights. (We grant weekly/monthly discount.)

Top guest favorite
An aerial view showcases the expansive grounds of La settecentesca Villa di Geggiano, surrounded by manicured gardens and lush vineyards. The main villa is prominent, with a circular driveway leading to it, while gentle hills extend into the background.
Cottage in Geggiano
4.99 out of 5 average rating, 151 reviews

Villa di Geggiano – Guesthouse

PLEASE NOTE THAT BEING IN THE COUNTRYSIDE WITH FEW PUBLIC TRANSPORTATION OTHER THAN TAXI, THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A CAR. The 18th century Villa di Geggiano, surrounded by vineyards and lovingly cared gardens, is located in the Chianti area near Siena, one of the most beautiful regions of Italy which will provide an idyllic and enchanting backdrop to your vacation. Our guesthouse is located in one of the garden pavilions of the villa.

Top guest favorite
The image features a rustic stone house surrounded by lush greenery, with a wooden door and shuttered windows. A set of stairs leads to a raised outdoor area, partially enclosed by a stone wall, providing a serene view of the surrounding nature.
Vacation home in San Gimignano
4.94 out of 5 average rating, 80 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

Guest favorite
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, 50 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 favorite
Condo in Gambassi Terme
4.99 out of 5 average rating, 122 reviews

Cosy Tuscan Home near Florence & San Gimignano

UN NIDO ACCOGLIENTE dove tradizione e confort moderno s'incontrano. Perfetto per chi desidera rallentare, rilassarsi e vivere la Toscana più autentica, lontano dal caos. Immagina di svegliarti nel cuore di un borgo toscano, affacciarti sulla piazza e iniziare la giornata con la tranquillità e I ritmi locali. L'appartamento completamente ristrutturato e arredato con gusto, si trova nel centro storico di Gambassi Terme, un punto strategico per eslorare le meraviglie della Toscana.

Top guest favorite
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 out of 5 average rating, 219 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.

Top guest favorite
A spacious living area features exposed brick walls, wooden beams, and warm lighting. A comfortable sofa and a mid-century modern coffee table sit invitingly, while a dining table and chairs are positioned nearby. Large windows enhance the natural light, which complements the earthy tones of the room.
Condo in San Gimignano
5 out of 5 average rating, 52 reviews

AnticaVista, Luxury Apartment with Tower Views

A hidden gem nestled within the ancient walls of a 14th-century tower house, right in the heart of San Gimignano, a UNESCO World Heritage Site. This one-of-a-kind apartment is where history meets contemporary elegance. Look out the window and you’ll feel like you can almost touch the medieval towers. The view is breathtaking: unforgettable glimpses of the majestic Torre Grossa, framed by the iconic skyline that earned San Gimignano its nickname, the “Medieval Manhattan.”

Top guest favorite
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, 97 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.

Top guest favorite
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 in Greve in Chianti
4.99 out of 5 average rating, 472 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 favorite
A winding driveway is lined with tall cypress trees on either side. The green landscape stretches into the distance, revealing rolling hills and a distant rustic building surrounded by nature, creating a serene and inviting setting.
Home in Montaione
4.96 out of 5 average rating, 135 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.

Guest favorite
Home in Tavarnelle Val di Pesa
5 out of 5 average rating, 7 reviews

Open Space Piscina e Giardino

La mia casa è immersa nella campagna toscana, tra olivi e vigne, nel cuore del Chianti. Intorno, panorami meravigliosi e un’atmosfera di pace e relax. Il giardino è uno spazio speciale, ideale per momenti da vivere all’aperto. Per chi lo desidera, è possibile – su richiesta – condividere esperienze legate alla cucina e alla convivialità, come cene preparate con cura, da gustare insieme, anche a lume di candela, in un contesto intimo e accogliente.

Popular amenities for Montaione vacation rentals