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Vacation rentals in Monteresi

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Top-rated vacation rentals in Monteresi

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

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Guest favorite
The stone farmhouse, characterized by a rustic façade, features arched doorways and shuttered windows. Lush greenery surrounds the entrance, offering a serene landscape. A gravel driveway leads to the main entrance, highlighting the spaciousness of the property.
Farm stay in Monteriggioni
4.9 out of 5 average rating, 107 reviews

Podere Casalino - Il Gatto

Set in the peaceful countryside near the Monteriggioni Castle, Il Casalino is the result of our love for restoring an old Tuscan farmhouse. My husband and I have carefully created two apartments for our guests: Il Gatto and La Pergola. We want you to feel at home from the very first moment. If you have any questions, feel free to message me: I will reply as quickly as possible. We truly look forward to welcoming you to Il Casalino and sharing this special place with you! Warm regards, Laura

Guest favorite
Home in Asciano
4.96 out of 5 average rating, 131 reviews

Palazzo Monaci - Piscina nelle crete Senesi

Benvenuti a Palazzo Monaci ! Un' oasi di natura e bellezza unica, nel cuore delle Crete Senesi, in Toscana. Un residence con piscina e vista mozzafiato sulle crete senesi. Perfetta per coppie o famiglie in cerca di una vacanza rilassante. La posizione è perfetta per esplorare le zone limitrofe. Potrete fare escursioni nella campagna toscana, visitare i borghi medievali caratteristici, assaggiare i vini locali prelibati e immergervi nella cultura e nella storia di questa affascinante regione.

Top guest favorite
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
A charming outdoor dining area features a round table set with delicate dishware and a pink tablecloth. Surrounding the table are intricately designed white chairs. A gazebo provides shade, and lush greenery is visible in the background, creating a serene setting for leisurely meals.
Farm stay in Ruscello
4.99 out of 5 average rating, 498 reviews

Agriturismo Fattoria La Parita

Appartamento in stile provenzale immerso tra il vigneto e gli olivi. Godrete della tranquillità della campagna a 10 km dalla città e 4 dall'autostrada. Il canto di ghiandaie e cucù faranno da colonna sonora al soggiorno mentre i caprioli brucano tra gli olivi. E' inclusa una colazione base all'italiana (caffè, tè, latte, biscotti ecc.), se invece preferite una colazione più ricca e servita al tavolo il costo è 15€ a persona (10€ da 5 a 15 anni, gratis meno di 5 anni). Disponibile wallbox EV.

Top guest favorite
An outdoor patio area features rustic furnishings and is framed by gracefully draping curtains. The space is adorned with comfortable seating and a communal dining table, set against a backdrop of tall cypress trees and a clear blue sky, inviting relaxation in a serene environment.
Home in Simignano
4.98 out of 5 average rating, 176 reviews

Casa al Gianni - Il Fienile di Simignano

Trasformato da un antico fienile, questo rifugio lussuoso offre 5 camere, 4 bagni, grande cucina attrezzata, ampio living, un ampio giardino privato con parcheggio, hot tub, patio con divani, BBQ, fire pit e cucina esterna. Ideale per chi cerca un'esperienza unica, unisce fascino rustico a comfort moderni. Perfetto per famiglie o gruppi, promette serate magiche sotto le stelle, tra relax nell'hot tub e cene all'aperto. Una fuga memorabile vi aspetta in questo angolo di paradiso!

Top guest favorite
A lush green garden is framed by a rustic pergola made of wooden beams. Grassy paths lead deeper into the garden, where vibrant flowers and trees provide a natural backdrop. Rolling hills and a clear blue sky are visible in the distance, creating a serene outdoor setting.
Home in Castellina in Chianti
4.98 out of 5 average rating, 130 reviews

Private Chianti Cottage, Garden & Vineyard Views

Set in a picturesque hamlet, overlooking the Chianti hills, this charming country house is just 10 minutes from Siena and Castellina in Chianti. Recently renovated, it blends authentic Tuscan charm with modern comforts. The house features two bedrooms, two bathrooms, a cozy living area and a fully equipped kitchen with a dishwasher, two fridges, and a washing machine. Outside, enjoy a beautiful garden and relax in the outdoor marble hot tub, soaking in the breathtaking views.

Top guest favorite
An outdoor patio area features a modern seating arrangement with a mix of light and dark furniture. A fabric sunshade is positioned overhead, providing shade. Surrounding the space, a landscaped garden includes colorful flowers and greenery, creating a relaxing atmosphere.
Home in Siena
4.97 out of 5 average rating, 114 reviews

Relais moderno a Siena

Questo elegante alloggio, a soli 5km dal centro di Siena, è vicino alla città e al Chianti . Adatto a coppie amanti del relax, a famiglie e a sportivi ( perfetto punto di partenza tour del Chianti). L'alloggio comprende due camere matrimoniali e una camera studio con divano letto, due bagni con doccia e un bagno di servizio. Posteggio ampio e gratuito, giardino con spazio solarium, campo da calcetto in erba, ricovero custodito e coperto per biciclette.

Top guest favorite
A rustic rural complex is depicted, featuring a stone building with a terracotta roof. Surrounding greenery enhances the setting, and a gravel path leads to the entrance. The scene is accentuated by a large tree and the clear sky above.
Condo in Monteriggioni
4.93 out of 5 average rating, 139 reviews

Il Vecchio Noce

Nell’antico complesso rurale del Caggio, “Il vecchio noce” offre un appartamento interamente ristrutturato (recentemente, questo inverno passato 2025/26) che può ospitare da 2 a 4 persone. Il complesso è situato nel cuore della campagna toscana, sulla Montagnola senese, nei pressi del borgo medievale di Monteriggioni e del tracciato della Via Francigena. L’alloggio è denominato “granaio” del borgo essendo esposto a sud ed al piano terra.

Top guest favorite
The aerial view captures the historic structure nestled among rolling green hills, framed by tall trees. The stone walls reflect medieval architecture, while a terrace offers an inviting space below. The surrounding landscape showcases farms and cypress trees against a clear blue sky.
Home in Monticchiello
4.98 out of 5 average rating, 215 reviews

"La Lambarda" tower Suite

In Val d'Orcia there is a small medieval village called Monticchiello, surrounded by walls and protected by four towers; one of these is the "La Lambarda", which stands at the highest point of the country and enjoys a panoramic view across the valley.

Guest favorite
The outdoor area features a spacious stone-paved patio surrounded by lush greenery. A large umbrella provides shade over a seating space, complemented by garden chairs and a table. Olive trees are visible, enhancing the natural surroundings.
Hut in Monteriggioni
4.94 out of 5 average rating, 103 reviews

Romantic Siena summer spa Francigena road

Recently renovated barn in the countryside at the foot of the hills of Siena just 10 minutes away from the city. The large garden with olive trees and the spacious yard make your stay pleasant and relaxing. *Hot tub included from may to september*

Guest favorite
A spacious living room is presented with terracotta flooring and wooden beams overhead. A comfortable sofa arrangement surrounds a wooden coffee table, with a flat-screen TV positioned nearby. Natural light filters through the windows, enhancing the inviting ambiance.
Home in Monteriggioni
4.9 out of 5 average rating, 213 reviews

Siena Countryside Colle Ciupi

Countryside Villa apartment. Located in the nearby of Siena (Colle Ciupi, 10 kms away) Ground floor: Kitchen, living room with fireplace, bathroom with shower. First Floor: 3 Double Bedrooms and 2 bathrooms, outdoor with courtyard and huge garden

Top guest favorite
An aerial view of the historic ex-convent showcases its rustic architecture surrounded by lush Tuscan countryside. The property is framed by pathways and green fields, revealing manicured gardens and trees. Nearby roads lead into the tranquil landscape, emphasizing the serene setting.
Apartment in Monteriggioni
4.9 out of 5 average rating, 110 reviews

La Senesina, Monteriggioni, Siena

“La Senesina” - Enchanting apartment immersed in the exquisitely beautiful Tuscan countryside, 4 km from Siena and 8 km from Monteriggioni. Ideal location from which to explore the most important towns and cities, rich in history, art and culture.

Popular amenities for Monteresi vacation rentals

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Siena
  5. Monteresi