
Pet-friendly holiday rentals in Monticiano
Find and book unique pet-friendly homes on Airbnb
Quick stats about holiday rentals that are pet-friendly in Monticiano

Total holiday rentals
Explore 30 holiday rentals in Monticiano

Nightly prices starting at
Monticiano holiday rentals start at $87 NZD per night before taxes and fees

Verified guest reviews
Over 550 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space and kid-friendly amenities

Holiday rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
30 of Monticiano holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Monticiano rentals

4.8 Average rating
Monticiano stays are highly rated by guests—averaging 4.8 out of 5!
Top-rated pet-friendly home rentals in Monticiano
Guests agree: These pet-friendly homes are highly rated for location, cleanliness and more.

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.
PetsOutdoor spacesValue
4.99 out of 5 average rating, 155 reviews
Tuscan cottage with an heavenly view
Heaven's Window takes your breath away. As our only guests, you will be surrounded by infinite views, endless tranquility, sounds of singing birds and calling deer. Down the valley and on your walks you may spot foxes ferrets and wild boar. Collect porcupine quills. Breathe! Halfway between Rome and Florence. Close to Siena, Val d’Orcia and countless hot springs . A private paradise surrounded by divine dining and hilltop jewels of antiquity like Montepulciano and Montalcino of sublime wines.
Outdoor spacesPetsAccuracy
4.97 out of 5 average rating, 251 reviews
Agriturismo Poggio Bicchieri ap. Memoria
Rilassati con tutta la famiglia in questo alloggio. L’agriturismo si compone di due appartamenti indipendenti con sala, cucina, camera e bagno. Non dovrai condividere nulla con il altri ospiti poiché é stata nostra cura organizzare tutto in maniera che ognuno abbia i propri spazi e tutto sia separato. All'esterno c’é un barbecue, tavolo con sedie e le sdraio. Nelle vicinanze Pienza, San Quirico d'Orcia, Bagno Vignoni, Montalcino e Bagni San Filippo. Per raggiungerci 1,5 km di strada sterrata!
WalkabilityPetsNearby
4.92 out of 5 average rating, 626 reviews
Wp Relais Borgo Vignalunga
Discover Borgo Vignalunga by WP Relais, an charming hamlet set in a 46-hectare estate in the heart of the Val D'Orcia, a UNESCO World Heritage Site. Surrounded by woodland, pastures, a lush vegetable garden, cultivated fields and three olive groves with 1,500 olive trees, Borgo Vignalunga is the ideal place to experience the true essence of Tuscany. The property is close to historical villages, evocative architecture, unspoilt natural landscapes and renowned restaurants, bars and wineries.
Outdoor spacesWalkabilityValue
4.95 out of 5 average rating, 146 reviews
Amazing Tuscany Villa, FREE parking
Modern villa with panoramic view in Montepulciano, a few steps from San Biagio. The villa is lovingly furnished and equipped with all comforts for a pleasant holiday. Enjoy breathtaking views of the surrounding countryside from the terrace, or relax in the two spacious gardens at your disposal. You will also have at your disposal a large kitchen to dabble in the magnificent art of cooking, something much loved by us Italians!!! Also available: Free Wi-fi Self check-in Reserved car parking
Outdoor spacesWalkabilityHot tub
4.93 out of 5 average rating, 335 reviews
Villa dei 2 Ulivi (Abbadia Isola)
FULLY AIR CONDITIONED, modern 6BR/4BA VILLA on Via Francigena: an enchanted paradise for friends & families with kids (trampoline, basketball area, soccer & volley/beach tennis nets, fossball, table tennis) & w. pets (fenced garden). Located in the small village Abbadia Isola in the shadow of the medieval castle of Monteriggioni, right on the path the ancient road & pilgrim route running from France to Rome (via Francigena) A.k.A FAMILY GROUPS KIDS FRIENDS dream VILLA Siena 12mn (ABB)
PetsWalkabilityBiking
4.97 out of 5 average rating, 174 reviews
Your Tuscan oak tree house, enchanting Val d'Orcia
The house enjoys a rare and enchanting view of the Val d’Orcia and Monte Amiata, ensuring maximum privacy. The interiors mirror the charm of the Tuscan style, with antique furniture and finishes made by local artisans. It is equipped with a double bedroom, a large living room with a big table, a fully equipped kitchenette, a double sofa bed in front of the fireplace, in the living room. Outside, the patio will allow you to eat with the colors of the sunset as a backdrop.
WalkabilityOutdoor spacesLocation
5.0 out of 5 average rating, 116 reviews
Casa al Gianni - Capanna
Ciao, siamo Cristina e Carmelo! Vi aspettiamo a "Casa al Gianni", il nostro agriturismo tra i boschi della Montagnola Senese a soli 20 minuti da Siena. Qui la vita rallenta: Solo il profumo della terra, il canto degli uccelli e la simpatia dei nostri animali. È un invito a riscoprire la bellezza delle piccole cose, immersi nel verde della Toscana più vera. Non è solo una vacanza, è un ritorno alle origini. Questo angolo di pace vi resterà nell'anima. Vi aspettiamo!
WalkabilityOutdoor spacesComfort
4.93 out of 5 average rating, 293 reviews
Tuscan Barn Apartment for 6 with panoramic pool
Panoramic Tuscan apartment converted from an old barn, with direct access to the garden and a shared panoramic swimming pool overlooking the Senese hills. Ideal for families or small groups of friends looking to enjoy for an authentic rural experience, privacy and relax. The apartment features three double bedrooms each with private bathroom, air-conditioning and WI-FI. A perfect place to enjoy nature, silence and unforgettable Tuscan sunsets.
Outdoor spacesPetsLong stay
4.89 out of 5 average rating, 100 reviews
Luxury frescoed apartment in the historical center
The Palazzo Pannilini Superior apartment is composed of a bright entrance enriched by an elegant coffered ceiling, a large fully frescoed lounge, a large foyer, a kitchen equipped with a terrace, a dining room topped with a frescoed vault, four bedrooms, three bathrooms, a wardrobe room, and a panoramic terrace where you can sunbathe and relax. The apartment is located at the second floor with no elevator. The apartment has air conditioning.
WalkabilityOutdoor spacesValue
4.97 out of 5 average rating, 116 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..).
PetsOutdoor spacesHeating
4.95 out of 5 average rating, 174 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 .
PetsWalkabilityLong stay
4.94 out of 5 average rating, 203 reviewsPopular amenities for Monticiano pet-friendly home rentals
Pet-friendly house rentals

Borgo Ripostena – n. 9 Frantoio
PetsOutdoor spacesSleep quality
4.94 out of 5 average rating, 118 reviews
Podere Piazza casa con vista panoramica
Outdoor spacesWalkabilityCleanliness
4.97 out of 5 average rating, 197 reviews
Secret Garden Siena
WalkabilityOutdoor spacesCleanliness
4.98 out of 5 average rating, 221 reviews
La finestra del Chianti
Outdoor spacesPetsCondition
4.9 out of 5 average rating, 136 reviews
RESIDENZA LECCIONE
Outdoor spacesWalkabilityHospitality
4.93 out of 5 average rating, 145 reviews
La Casa di Nada Home
WalkabilityPetsShared spaces
4.87 out of 5 average rating, 217 reviews
Eleutherìa: Cozy Cottage in the heart of Tuscany
PetsWalkabilityGetting around
4.96 out of 5 average rating, 123 reviews
Casolare nel Chianti, Siena Toscana
Outdoor spacesWalkabilityBathroom
4.83 out of 5 average rating, 169 reviewsPet-friendly home rentals with a pool

Pieve di Caminino Historic Farm
PetsOutdoor spacesKitchen
4.92 out of 5 average rating, 204 reviews
La Pieve - the house next to the church
Outdoor spacesWalkabilityKitchen
4.97 out of 5 average rating, 117 reviews
Suite, private apt for 2/4, pool
Outdoor spacesWalkabilityParking
4.95 out of 5 average rating, 104 reviews
LUXURY VILLA SALTWATER POOL 35 min FROM CORTONA
Outdoor spacesWalkabilityAccuracy
4.99 out of 5 average rating, 116 reviews
PIERFANTINI private Chianti house ♿️ 🏊♂️ 🐶
Outdoor spacesWalkabilityBeach
4.91 out of 5 average rating, 100 reviews
EcoLodge – modernes Design in ruhiger Panoramalage
WalkabilityOutdoor spacesBreakfast
4.94 out of 5 average rating, 111 reviews
Agriturismo La Villa - Il Castagno, Pool & Garden
PetsOutdoor spacesComfort
4.98 out of 5 average rating, 222 reviews
Unique view 3 bdr villa with pool & A/C in Pienza
WalkabilityOutdoor spacesShared spaces
4.95 out of 5 average rating, 104 reviewsPrivate, pet-friendly home rentals

Apartment in a Tuscan farmhouse at Le Pietre Vive
WalkabilityPetsComfort
4.92 out of 5 average rating, 359 reviews
La Casetta di Brunello,very panoramic with terrace
Outdoor spacesWalkabilityAccess
4.9 out of 5 average rating, 324 reviews
Casale in pietra in Val D’Orcia
Outdoor spacesWalkabilityAccess
4.98 out of 5 average rating, 160 reviews
Celeste - Il colore del cielo d'estate in Toscana
Outdoor spacesDecorAmenities
4.98 out of 5 average rating, 326 reviews
Casa Sabina
PetsOutdoor spacesBreakfast
4.98 out of 5 average rating, 129 reviews
Typical Tuscan Cottage with swimming pool and park
PetsWalkabilityPool
4.95 out of 5 average rating, 42 reviews
Independent country house with private pool
WalkabilityOutdoor spacesLaundry
4.7 out of 5 average rating, 20 reviews
Golden View - Casale da sogno in Toscana
Outdoor spacesPetsCheckout
4.97 out of 5 average rating, 65 reviewsDestinations to explore
- Lake Trasimeno
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Stazione Santa Maria Novella
- Cala Violina
- Parco Regionale Della Maremma
- Mercato Centrale
- Spiagge Bianche
- Fortezza da Basso
- Gulf of Baratti
- Uffizi Gallery
- Piazza della Repubblica
- Parco delle Cascine
- Piazzale Michelangelo
- Palazzo Vecchio
- Del Chianti
- Piazza della Signoria
- Pitti Palace
- Boboli's Garden
- Spiaggia di Capo Bianco
- Mount Amiata





