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Vacation rentals in Monteresi

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Top-rated vacation rentals in Monteresi

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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, 109 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

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, 153 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
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, 339 reviews

Podere Vergianoni immerso nelChianti con piscina

Podere Vergianoni è un antica e storica proprietà risalente al 1600 situato nelle splendide colline del Chianti in Toscana con la possibilità di organizzare servizio navetta e esperienze esclusive su misura per voi . L'appartamento è disponibile per 2 adulti con possibilità aggiunta divano letto per 2 bambini sotto i 12 anni . Nel grande cortile esterno troverete una piscina a sale con area relax su terrazza panoramica con vista su castello colline e vigneti con tramonti unici.

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, 181 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
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, 223 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 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, 131 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
Home in Siena
4.97 out of 5 average rating, 115 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.

Guest favorite
A bright bedroom is showcased with a spacious canopied bed, featuring soft linens. White curtains frame the open window, which reveals a scenic view of lush greenery. A bedside lamp adds a touch of warmth, complementing the serene atmosphere.
Condo in Monteriggioni
4.94 out of 5 average rating, 17 reviews

Loggiato di Lorena - Lungo la Via Francigena

❤ Loggiato di Lorena ❤ ✔ Appartamento di pregio (100 m²) in dimora storica con vista sui colli senesi ✔ Ambiente molto silenzioso e rilassante ✔ Parcheggio gratuito e riservato in loco ✔ 5 minuti in auto dal borgo storico di MONTERIGGIONI e di STOMENNANO ✔ Tracciato VIA FRANCIGENA per escursioni: noleggio E-Bike e Maneggio nelle vicinanze ✔ Wi-fi veloce e GRATUITO ✔ SmartTV ✔ Adatto a smart working ✔ 15 minuti in auto dal centro di SIENA

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
Condo in Monteriggioni
5 out of 5 average rating, 11 reviews

Tramonti mozzafiato in Toscana | Vista e relax

Benvenuti a Il Poggiolo, una casa vacanze dal sapore autentico immersa nel cuore della Toscana, a pochi chilometri da Siena. Situata in una posizione panoramica tra dolci colline e paesaggi da cartolina, questa dimora è perfetta per chi cerca tranquillità, bellezza e tradizione. tutti gli ospiti che hanno soggiornato si sono innamorati del panorama e della tranquillità che si respira a due passi da tutte le mete del nostro territorio.

Guest favorite
The image captures a charming garden courtyard surrounded by lush greenery. A villa with green window shutters is partially covered in climbing vines. Neat hedges and terracotta pots with plants create structured pathways, while dappled sunlight filters through the trellised canopy overhead.
Home in Siena
4.86 out of 5 average rating, 36 reviews

Villa Saracino

Appartamento al primo piano di una villa signorile alle porte di Siena. Alloggerete in un ambiente elegante con mobili e suppellettili di pregio circondati da un giardino all'italiana e da una grande oliveta. Avrete la possibilità di posteggiare in sicurezza e gratuitamente all'interno del parco e da qui raggiungere comodamente il centro di Siena a 600 metri di distanza Arrivando in treno la casa si trova a pochi minuti.

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, 217 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.

Popular amenities for Monteresi vacation rentals

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