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Vacation rentals in Monticiano

Find and book unique accommodations on Airbnb

Quick stats about vacation rentals in Monticiano

  • Total vacation rentals

    Explore 70 vacation rentals in Monticiano

  • Nightly prices starting at

    Monticiano vacation rentals start at G$10,459 GYD per night before taxes and fees

  • Verified guest reviews

    Over 1,190 verified reviews to help you choose

  • Family-friendly vacation rentals

    40 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 30 rentals that welcome pets

  • Vacation rentals with a pool

    30 properties feature pools

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    60 of Monticiano vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Monticiano rentals

  • 4.8 Average rating

    Monticiano stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated vacation rentals in Monticiano

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

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Guest favorite
Villa in Siena
4.8 out of 5 average rating, 295 reviews

XIII Century Tower with Private Panoramic Pool

Ancient country tower property with 5 airconditioned bedrooms for up to 10 guests at the heart of the peaceful Montechiaro organic wine estate. From your private pool, soak in the Tuscan sun and enjoy unforgettable views of the Chianti rolling hills and the medieval towers of Siena. The property also boasts access to the endless olive grove, a large patio area for outside dining in the shade, ping pong table for fun family matches, WIFI & free parking. Silence and time are the real luxury here.

Top guest favorite
Cottage in Monticiano
5.0 out of 5 average rating, 40 reviews

Typical Tuscan Cottage with swimming pool and park

Il Country Cottage è ubicato nel cuore della Toscana autentica, in un territorio incontaminato, con una biodiversità unica. Sito a soli 5 minuti di auto dalla famosa Abbazia di San Galgano e da l'Eremo di Montesiepi, dove è custodita la prestigiosa "Spada nella Roccia". Viene affittata l'intera proprietà: la tipica casa toscana di campagna, la piscina, il giardino e il parco recintato. Una location perfetta per rilassarsi con la massima privacy, senza lo stress ed il logorio della vita moderna

Top guest favorite
Condo in Monticiano
4.98 out of 5 average rating, 65 reviews

Il TramontO

Il TramontO è un appartamento completamente ristrutturato elegante e rustico immerso nella natura della toscana, con vista panoramica, giardino, terrazza e minipiscina idromassaggio ad USO Esclusivo. Spiccano moltissimi dettagli in legno naturale e pietra antica. A pochi passi dall’Abbazia di San Galgano, raggiungibile anche con un incantevole sentiero di 5 km dal paese. A 35 km da Siena e 92 da Firenze, ricavato da una torre Storica del 1200, offre charme, relax e tramonti indimenticabili.

Top guest favorite
An elegant dining area is centered around a large wooden table surrounded by soft, upholstered chairs. Beams of natural light filter through skylights and windows, highlighting the warm wooden ceiling and contemporary kitchen space in the background.
Vacation home in Monteroni d'Arbia
5.0 out of 5 average rating, 35 reviews

Tuja

Il Tuja di Casanova di Campriano è un appartamento di 120mq ristrutturato con eleganza e funzionalità nel rispetto dello stile toscano per un soggiorno di relax immersi nella natura. Dal suo terrazzino e dal suo tavolo in giardino puoi godere di una vista unica a 180° che spazia dalle Crete Senesi fino a Montalcino e al Monte Amiata. La piscina con vista panoramica incanta ad ogni sguardo. Questa struttura è perfetta per visitare Siena e i bellissimi borghi medievali della Val d'Orcia.

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
4.97 out of 5 average rating, 194 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 rustic stone building features a wooden balcony with a lantern overhead, reflecting traditional architecture. Red roses bloom at the base, adding color to the scene, while wooden shutters frame the windows above, harmonizing with the natural surroundings.
Home in Castello di Tocchi
4.97 out of 5 average rating, 66 reviews

Appartamento nel borgo di Castello di Tocchi

L' alloggio è situato in un'area naturale protetta con boschi di castagno, fiumi e torrenti (Farma) e intensa presenza di fauna locale (caprioli, istrici, daini, cinghiali, uccelli diurni e notturni ). E' a sud di Siena (30 km) in un contesto di città d'arte (Valdorcia e Valdimerse), giacimenti archeologici e strutture termali. L'appartamento, vissuto nel tempo da una famiglia di boscaioli, restaurato riportando in luce le specifiche architettoniche e decorative tradizionali.

Top guest favorite
A bright living area features a cozy blue sofa adorned with patterned cushions. A wooden dining table is positioned nearby, with four chairs available. Shelves on the walls hold various items, and windows are present, allowing natural light to fill the space.
Apartment in Monticiano
4.92 out of 5 average rating, 62 reviews

piccolo appartamento

The apartment is located on the first floor of an early 20th century building, in the historic center of the municipality of Monticiano. The entrance opens onto a room with a small kitchen. In the apartment there are two small bedrooms. In the first bedroom, the queen-size bed (1.40x2.00 m) is hanging off the ground approximately 1.70 m high. The second bedroom has a single bed equipped with a pull-out extension that allows it to be transformed into a double bed.

Guest favorite
Home in Monteroni d'Arbia
4.97 out of 5 average rating, 64 reviews

Golden View - Casale da sogno in Toscana

Un angolo di pace tra splendidi cipressi, dove regnano silenzio e tranquillità. Rilassati nella cascata idromassaggio in giardino, accendi il caminetto nelle sere più fresche o goditi una grigliata al barbecue. La camera master ti coccola con vasca idromassaggio e sauna privata. La vasca esterna sarà utilizzabile dal 1 maggio al 1 novembre di ogni anno, successivamente potrà essere usata su richiesta ma l'acqua interna non riuscirà a superare i 25 gradi.

Guest favorite
Villa in Monteroni d'Arbia
4.95 out of 5 average rating, 171 reviews

"Villa Daisy" con vista su Siena

Meravigliosa villa con ingresso indipendente all'interno del podere "Caggiolo", riportato alla luce con curata e profonda ristrutturazione che ha mantenuto intatti i lineamenti tipici di un podere toscano. Splendida vista panoramica su Siena. Situato alle Ville di Corsano, a soli 14 km dalla città. Luogo ideale per trascorrere giorni in totale relax e godere delle meraviglie che questa zona offre (Chianti, Val d'Orcia, Crete Senesi..).

Top guest favorite
A stone patio is shown, featuring a small table set with two chairs. The entrance to the cottage is visible, accompanied by wooden shutters. Lush greenery surrounds the area, providing a serene environment.
Cottage in Ponte Feccia
4.95 out of 5 average rating, 200 reviews

Country cottage C&M immerso nel verde love Tuscany

Country cottage in pietra , indipendente nella campagna Toscana in provincia di Siena ,con ampio giardino, portico e gazebo. La nostra casa e' situata nella campagna del comune di Chiusdino, a soli 5 minuti dai due paesi principali Monticiano e Chiusdino e 10 minuti dalla splendida Abbazia di.Galgano . 30 minuti da Siena , da Monteriggioni , un'ora da Firenze e 30/40min minuti dal mare. Soli 20 minuti dalle belle Terme del Petriolo .

Superhost
Villa in Monticiano
4.67 out of 5 average rating, 18 reviews

Independent country house with private pool

Situated in a panoramic position overlooking a green landscape of wooded hills, this beautiful stone house, surrounded by a wide fenced garden, has been restored and furnished simply and comfortably for holiday use. The house is surrounded by a wide fenced garden where the pool is set (6x 12 m – depth from 1,20 to 1,50m, seasonal opening) and guests have a covered loggia furnished with table and chairs for outside dinners.

Top guest favorite
A charming rural building features large windows and stone walls, surrounded by lush greenery. The entrance includes a few steps leading to a door framed by vibrant flower pots, while a well-maintained lawn extends in front.
Farm stay in Monticiano
5.0 out of 5 average rating, 37 reviews

Romantic and quiet stay near Siena, with garden

The apartment is great for 2 people. In the apartment there are a kitchen, a large double bedroom and a bathroom. In the bedroom you can add a bed for baby. FREE WIFI - Mbps download 25,45 e Mbps in upload 3,03 THE PRICE INCLUDES ALL CONSUMPTION AND TOURIST TAX The car is necessary, parking is free and next to the house.

Popular amenities for Monticiano vacation rentals

When is the best time to visit Monticiano?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$24,473 GYDG$24,682 GYDG$24,055 GYDG$24,264 GYDG$21,963 GYDG$37,023 GYDG$21,963 GYDG$20,917 GYDG$21,963 GYDG$20,080 GYDG$21,754 GYDG$24,473 GYD
Avg. temp8°C8°C11°C13°C18°C22°C25°C25°C21°C17°C12°C9°C

Frequently Asked Questions

  • Are there family-friendly vacation rentals in Monticiano?

    Monticiano has more than 40 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in apartment rentals in Monticiano?

    Experience the best of Monticiano with our apartment rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly vacation rentals in Monticiano?

    Four-legged friends are welcome in Monticiano. Choose from more than 30 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Monticiano?

    Yes! Work meets play with ease at over 20 vacation rentals in Monticiano featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there Monticiano villa rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 10 villa rentals with pools in Monticiano, available on Airbnb. Make a splash and soak up the sun in style!

  • Do apartment rentals in Monticiano have a kitchen?

    Absolutely! We offer over 20 apartment rentals with a kitchen in Monticiano. Enjoy a tailored experience with all the comforts you desire.

  • Do villa rentals in Monticiano have wifi?

    Absolutely! We offer over 10 villa rentals with wifi in Monticiano. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Monticiano have free parking?

    Absolutely! We offer over 10 apartment rentals with free parking in Monticiano. Enjoy a tailored experience with all the comforts you desire.