Vacation rentals in Montecastello

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Montecastello

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

0 of 0 items showing

1 of 3 pages

Top guest favorite

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.

Condo in Noce

5 out of 5 average rating, 266 reviews

Podere Vergianoni immerso nelChianti con piscina

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 favorite

An outdoor seating area is illustrated with four black wicker chairs arranged around a small table. Lush greenery surrounds the space, featuring a mix of tall trees and vibrant shrubs. Sunlight filters through the leaves, creating a peaceful ambiance in the garden.

Apartment in Treggiaia

5 out of 5 average rating, 38 reviews

Volpe Sul Poggio - Country Suite

An oasis of relaxation in the Valdera countryside, ideal for visiting the main Tuscan destinations. Renovated in April 2024 from the old cellars of the family farmhouse, it enjoys an exclusive 5000 sqm park, where you can experience full immersion in nature and, with a little luck, you can see foxes and roe deer that live on the estate. Ideal for hiking and mountain biking enthusiasts, it is located 30/40 minutes from the coastal areas and the main Tuscan provinces of Lucca, Pisa, Florence and Siena

Top guest favorite

A window offers a scenic view of the rolling hills and lush greenery of the Tuscan countryside. A round wooden table is set with plates and glasses, complemented by wicker placemats, creating an inviting dining area under soft morning light.

Apartment in Palaia

5 out of 5 average rating, 17 reviews

Casa Billi

Accogliente appartamento di mq 90 con bellissimo panorama sulla campagna al secondo e ultimo piano (no ascensore) di antico edificio ristrutturato recentemente. Due camere da letto matrimoniali, soggiorno con cucina, uno studio, due bagni di cui uno con doccia e un ripostiglio. Uso esclusivo di una bella terrazza(non al piano dell'appartamento). Pochi minuti a piedi e sarete nel centro del vivace paese di Palaia dove troverete piccole botteghe per fare la spesa, ristoranti, pub e un Bar.

Top guest favorite

A spacious terrace is surrounded by lush greenery, featuring terracotta pots filled with plants. Comfortable wooden chairs are positioned to invite relaxation, overlooking scenic hills in the distance. A soft canopy provides shade, enhancing the tranquil atmosphere of this outdoor space.

Home in Peccioli

4.99 out of 5 average rating, 129 reviews

House with a breathless view in Tuscany

Halfway between Pisa and Florence this house comes with a large panoramic terrace, equipped with sunchairs and a large table for outdoor dining. Below, an hanging garden on the property overlooks one of the most striking views in Tuscany. The location is strategic, in the beating heart of an ancient medieval village, now home to an open-air contemporary art museum. Peccioli is a great starting point for those who want to visit the art cities of Tuscany, or immerse yourself in local life,

Top guest favorite

A historic tower rises prominently against a blue sky dotted with fluffy clouds. Surrounding greenery complements the stone structure, with trees and small buildings visible along the hillside, collectively conveying a sense of tranquility.

Villa in Montecatini Val di Cecina

4.99 out of 5 average rating, 123 reviews

Belforti Tower

Torre dei Belforti is the perfect place for people who love beauty, nature and art. Sleeping at the Tower is like traveling trough the time, between knights and princesses. The wonder of this place is enriched by a big garden, with its swimming pool, the cypresses alleys and the olive trees. The village is also a magic place well preserved and still alive. We are Emilia and Luca, we live here and our mission is to give the best to our guests, to fully enjoy this marvelous place.

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

4.99 out of 5 average rating, 185 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.

Superhost

An aerial view showcases a spacious patio with two large umbrellas providing shade. Comfortable seating arrangements are visible, along with decorative potted plants. The sparkling pool is in the background, surrounded by lounge chairs. Solar panels are installed on the roof, reflecting sustainability.

Apartment in Forcoli

4.88 out of 5 average rating, 17 reviews

"La casa delle Rondini" open space

Relax in thisoasis of quiet and elegance. Studio with private terrace, open space with kitchen and living room ; very comfortable sofa bed, very high and comfortable mattress, air conditioning and smart TV. Pool view. Bathroom with shower . Outdoor area with table and chairs and private parking. Swimming pool with deck chairs and umbrellas and a small BBQ corner The pool could be shared with 3 other two-room apartments. Quiet area but close to downtown and all amenities

Top guest favorite

An outdoor seating area is shown with a sturdy wooden table surrounded by several chairs. An umbrella provides shade, while the rustic stone walls of the ancient structure frame the picturesque view of the valley beyond. A grassy area with a terracotta floor enhances the inviting ambiance.

Home in Palaia

4.94 out of 5 average rating, 211 reviews

AT THE CASTELLO DELLA MONTACCHITA WHOLE APARTMENT

REGISTRATION No. 50024LTN0077 Entire small private house overlooking the valley, with 1250 sqm of garden for the exclusive use of guests, renovated in rustic style inside an ancient medieval fortress. Unique place, great starting point for visiting Pisa, Lucca, Florence, San Gimignano and just 40 minutes from the sea and located in the truffle area. Remember before booking: those who are not named in the reservation will not be able to enter the property.

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

4.95 out of 5 average rating, 112 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

A newly constructed swimming pool features clear turquoise water, surrounded by landscaped grass. Sun loungers sit next to the pool, while manicured hedges and olive trees frame the space, offering a serene outdoor environment. The house stands in the background under a clear blue sky.

Home in Palaia

5 out of 5 average rating, 46 reviews

Casolare Ceppeto di Casapieri - Italy, Pisa

Il Casolare, located in the heart of Tuscany at 145 m. high, entirely surrounded by olive trees and vineyards, with 13,000 square meters. of agricultural land, where you can stay in peace and tranquility in contact with nature. The cottage has 8 beds, 2 bathrooms, a kitchen and a dining room, as well as a large outdoor area where you can eat and living comfortably under the roof, is completed by a newly built swimming pool (13.5x5.5).

Guest favorite

A rustic building is seen under a starry night sky, with a partial roof providing shelter. Soft light glows from the interior, illuminating the entrance. Lush greenery and trees surround the scene, adding depth to the serene nighttime landscape.

Farm stay in Simignano

4.9 out of 5 average rating, 212 reviews

Casa al Gianni - Capanna

Hi, we're Cristina & Carmelo! We invite you to live an authentic experience in our farmhouse “Casa al Gianni” located 20 minutes from Siena. Our hallmark is simple life in close contact with nature and the animals of our farm. Immersed in the woods and the beautiful Tuscan countryside, you will spend an unforgettable vacation. This slice of paradise will remain in your heart!

Top guest favorite

The image features a serene infinity pool reflecting the surrounding trees and villa during sunset. Sun loungers are positioned beside the pool, and the well-maintained outdoor area offers a tranquil ambiance enhanced by the natural landscape.

Farm stay in Pisa

4.99 out of 5 average rating, 304 reviews

Tenuta Chiudendone in Tuscany

Great place in the middle of Tuscan Hills, you will be sorrounded by nature but close to all the beautiful cities of Tuscany! We rent two apartments, one on the upper floor called Balla and one on the ground floor called Modigliani. Tell us which one you prefer. PLEASE NOTE YOU WILL NEED A CAR DURING YOUR STAY.