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Pet-friendly holiday rentals in Pienza

Find and book unique pet-friendly homes on Airbnb

Quick stats about holiday rentals that are pet-friendly in Pienza

  • Total holiday rentals

    Explore 30 holiday rentals in Pienza

  • Nightly prices starting at

    Pienza holiday rentals start at $153 NZD per night before taxes and fees

  • Verified guest reviews

    Over 1,780 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space and kid-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    30 of Pienza holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Pienza rentals

  • 4.9 Average rating

    Pienza stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated pet-friendly home rentals in Pienza

Guests agree: These pet-friendly homes are highly rated for location, cleanliness and more.

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Top Guest favourite
The exterior of a charming stone villa is surrounded by a lush garden featuring vibrant lavender plants. Stairs lead to a welcoming entrance adorned with potted flowers and a shaded seating area. The rustic façade reflects traditional Tuscan architecture against a clear blue sky.
Villa in Chianciano Terme
4.97 out of 5 average rating, 128 reviews

Charming Tuscan Villa with View forFamily&Friends

The house is a typical podere of the late 1800, stone walls, chestnut beams, and hand-made tiles have all been kept; what has changed is the comfort behind them. The Host Fulvia lives in the ground-floor apt. and she's on hand throughout your stay without ever intruding — a rhythm that guests consistently single out. Total accommodation is 8 guests across 2 bdr and 2 bathrooms. Visit Montepulciano, Pienza, Bagni Vignoni and iconic Unesco sites in Val d'Orcia within short and easy driving away

Outdoor spacesWalkabilitySleep quality

Top Guest favourite
Two comfortable chairs are positioned on a lush green lawn, complemented by a small wooden table. A basket of vibrant yellow flowers is nearby, set against a backdrop of rolling hills and cypress trees under a clear blue sky.
Apartment in Monticchiello
4.97 out of 5 average rating, 187 reviews

Casa Bonari - un paradiso per gli occhi

Casa Bonari è un appartamento indipendente, non condiviso, su un unico livello all'interno di una villa ai piedi di Monticchiello. E' composto da 3 camere da letto, 2 bagni, cucina full optioned e salotto. Le stanze sono arredate in stile toscano, con vecchi mobili di famiglia ristrutturati uniti ad elementi contemporanei. La cucina è completamente attrezzata e l'appartamento circondato su ogni lato da un grande giardino, così che tutte le stanze vantano un bellissimo panorama sulla campagna.

WalkabilityOutdoor spacesBackyard

Top Guest favourite
A charming cottage is shown with a terracotta facade and a tiled roof. A small table with two chairs is set on a patio, surrounded by potted plants. Lush greenery and trees can be seen in the background under a clear blue sky.
Guesthouse in Macciano
4.97 out of 5 average rating, 246 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.

PetsWalkabilityBackyard

Top Guest favourite
An inviting interior features exposed brick walls and a blend of modern and rustic design elements. A staircase leads to the upper floor, while large doors open to reveal a view of the outdoors. A wooden table and a cozy chair enhance the living space.
Apartment in Montepulciano
4.98 out of 5 average rating, 163 reviews

Under the sunset, Montepulciano

In 2023 my son Guglielmo and I decided to restore the old oratory of a church from the 1600s by creating a two floor apartment: upstairs we have 2 bedrooms equipped with AC and 2 en-suite bathrooms with shower; downstairs a spacious living room with stereo Available a table outside with great view and a nice garden 50 mt away where to have a private wine tasting or barbecue for all the guests of our 4 apartments, after 7pm if booked large in advance Large free parking area 100 mt away

Outdoor spacesWalkabilityCheck-in

Top Guest favourite
The villa's exterior is highlighted by a modern structure with large glass doors and a gently sloping roof. It is surrounded by lush greenery and features a patio area with steps leading to the entrance. Soft lighting illuminates the garden, creating a serene evening ambiance.
Villa in Montepulciano
4.92 out of 5 average rating, 331 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 spacesPetsAir conditioning

Top Guest favourite
A charming outdoor seating area is set against a backdrop of rolling green hills. Two green metal chairs and a matching table are surrounded by flowering plants, with cypress trees rising in the distance under a partly cloudy sky.
Condo in Pienza
5.0 out of 5 average rating, 159 reviews

Casa rurale toscana in Mascagni Farmhouse Pienza

Risali le iconiche colline toscane fino a Mascagni Organic Farm, un'azienda biologica dove ti aspetta la tua nuova casa: un fienile del 1500 finemente ristrutturato immerso tra olivi e campi di grano. Rilassati prendendo una tazza di tè, raccogli rosmarini e lavande nel giardino con vista mozzafiato sulla Val d'Orcia. Riscopri la tua vera natura tra i campi incontaminati e gli olivi: qui le passeggiate e i giri in bici non hanno confini! Pronto a creare ricordi che dureranno tutta la vita?

PetsOutdoor spacesFamily

Guest favourite
Aerial view of a scenic agriturismo surrounded by vineyards and rolling hills. The property features a pool and is framed by tall cypress trees, enhancing the natural landscape of lush green and golden fields under a partly cloudy sky.
Farm stay in Montepulciano
4.96 out of 5 average rating, 115 reviews

Rural Tuscany | Family farmstay with restaurant

Via della Stella is a charming agriturismo with a housing surface of 530m², divided over nine separate apartments. Each apartment has its own living room, kitchen and one or more bath & bedrooms. The farmhouse has a wonderful panoramic swimming pool. Its great position with view over the hills heading up to Montepulciano create a serene atmosphere. The farmhouse has been carefully decorated in rural Tuscan style. Activities such as wine tastings and cooking classes are available onsite.

PetsOutdoor spacesPool

Top Guest favourite
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!

WalkabilityPetsView

Top Guest favourite
A charming stone cottage is set within lush greenery, featuring a covered porch with outdoor seating. Olive trees surround the area, enhancing the natural beauty. A bicycle leans against the wall, inviting exploration of the peaceful countryside.
Cottage in Osteria delle Noci
5.0 out of 5 average rating, 115 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.

WalkabilityPetsCheckout

Top Guest favourite
An aerial view highlights a stone farmhouse nestled within lush greenery, surrounded by mature trees. The structure features a terracotta-tiled roof and a charming porch. A pathway leads to a smaller stone building, providing a sense of harmony with the natural landscape.
Villa in Sarteano
4.97 out of 5 average rating, 158 reviews

Casale in pietra in Val D’Orcia

Casale toscano del '800 con pietre a vista immerso nella meravigliosa campagna Toscana con uno splendido panorama sulla Val di Chiana. E' circondato da un parco di 6 ettari con un uliveto di 300 piante. Si trova a Sarteano, nel paese, un antico borgo medioevale con un castello da sogno, conosciuto per il Festival della Musica e del Jazz che si svolge alla fine dell'estate. Siamo nella bellissima Val d'Orcia, patrimonio naturale dell'umanità dall'UNESCO dal 2004.

WalkabilityPetsGetting around

Top Guest favourite
A serene garden area features a lounging chair with a folded towel placed neatly on it. Stone planters and lush greenery surround a small hot tub, complemented by flowering plants and trees. The backdrop includes rustic architecture under a clear sky.
Villa in Monticchiello
4.98 out of 5 average rating, 182 reviews

Villa unesco heritage, Jacuzzi & garden. BB Daria

Carefully renovated and refurbished over a sustained period in order to maintain the original quality of its architecture, San Lorenzo Villa is open to guests. You are invited to enjoy the beauty, comfort and privacy of a beautiful independent villa in the centre of Monticchiello, from where you can have an incredible view on the Val d'Orcia, the UNESCO heritage! Don't forget a delicious breakfast (whatever you like) in our so close typical restaurant

WalkabilityOutdoor spacesAccess

Top Guest favourite
An outdoor seating area features a small table surrounded by two chairs, adorned with a light breakfast setup. The stone facade of the house is complemented by climbing vines and a bright flower arrangement, inviting guests to enjoy the fresh air.
Holiday home in Monticchiello
4.96 out of 5 average rating, 137 reviews

In Toscana Camere

**Your Dream Retreat in the Heart of Val d'Orcia** Welcome to In Toscana Camere, a charming holiday home located in the historic center of Monticchiello, a Tuscan village full of charm and authenticity. Surrounded by stone walls and enhanced by modern, comfortable interiors, this home offers the perfect balance between tradition and contemporary style. Wake up every morning to a breathtaking view of the stunning Val d'Orcia.

Outdoor spacesPetsLong stay

Popular amenities for Pienza pet-friendly home rentals

Pet-friendly home rentals with a pool

When is the best time to visit Pienza?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$201 NZD$192 NZD$195 NZD$240 NZD$245 NZD$223 NZD$211 NZD$229 NZD$240 NZD$221 NZD$207 NZD$194 NZD
Avg. temp5°C6°C9°C12°C16°C21°C23°C24°C19°C14°C9°C5°C

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