Pet-friendly vacation rentals in Montepulciano

4.97 out of 5 average rating, 250 reviews

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

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 spacesWalkabilityCleanliness

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.

4.98 out of 5 average rating, 165 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

WalkabilityOutdoor spacesTV

4.93 out of 5 average rating, 334 reviews

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

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 spacesWalkabilityParking

Villa in Castiglione d'Orcia

A serene outdoor pool area is surrounded by lush greenery and rustic stone pathways. Lounge chairs are positioned beside the pool, creating a space for relaxation. The picturesque villa can be seen in the background, framed by trees and gentle hillside.

4.95 out of 5 average rating, 146 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.

WalkabilityOutdoor spacesValue

Aerial view of a serene agriturismo surrounded by lush vineyards and golden fields. The property features a pool set amidst well-kept gardens and tall cypress trees. Rolling hills in the background extend towards the horizon, contributing to the peaceful landscape.

4.94 out of 5 average rating, 107 reviews

Tuscan farmhouse stay with restaurant and pool

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.

WalkabilityOutdoor spacesView

4.96 out of 5 average rating, 168 reviews

A large, rectangular swimming pool is set within a green lawn, surrounded by tall trees and blooming shrubs. Sun loungers are placed around the pool, providing a space for relaxation. The lush Tuscan countryside stretches into the distance under a clear blue sky.

Villa in Montepulciano

A paradise in Montepulciano...

Villa Il Cubo has a large private park and swimming pool and marvellous views on the Tuscan countryside. It is fully air-conditioned and the decoration has been updated with charming details that will make you enjoy the best Tuscany has to offer. We have electric vehicle charging point at a moderate extra contribution. IN JULY AND AUGUST WE LET FOR A MINIMUM OF 7 DAYS FROM SATURDAY TO SATURDAY. Exceptions are possible only if don't create unrentable gaps between one guest and the next.

PetsOutdoor spacesHeating

5.0 out of 5 average rating, 513 reviews

An open kitchen area features a large window that offers a panoramic view of the surrounding landscape. A dining table is set for two, with modern chairs and colorful decor elements. Light reflects off the terracotta floor, highlighting the wooden beams overhead.

Loft in Montepulciano

La Piazzetta - Cozy open space in the historic center of Montepulciano

Pour yourself a glass of wine and sit next to the fireplace of this open space with a warm Tuscan atmosphere: wooden beams, terracotta floors, stone walls. Then go outside and admire the magnificent view of the Valdichiana. Pour yourself a glass of wine and sit next to the fireplace of this open space with a warm Tuscan atmosphere: wooden beams, terracotta floors, and stone walls. Enjoy yourself and relax! Then go out and admire the magnificent view of the Valdichiana Valley.

Outdoor spacesWalkabilityHospitality

4.97 out of 5 average rating, 158 reviews

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

Stone farmhouse in Val D'Orcia

19th-century Tuscan farmhouse with exposed stones immersed in the wonderful Tuscan countryside with a splendid view of the Val di Chiana. It is surrounded by a 6-hectare park with an olive grove of 300 plants. It is located in Sarteano, in the village, an ancient medieval village with a dream castle, known for the Music and Jazz Festival that takes place at the end of summer. We are in the beautiful Val d'Orcia, a UNESCO World Natural Heritage Site since 2004.

WalkabilityOutdoor spacesComfort

4.98 out of 5 average rating, 182 reviews

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

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 spacesValue

5.0 out of 5 average rating, 162 reviews

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

Tuscan rural home in Mascagni Farmhouse Pienza

Climb the iconic Tuscan hills to Mascagni Organic Farm, an organic farm where your new home awaits: a finely restored 16th-century barn nestled among olive trees and wheat fields. Relax with a cup of tea, pick rosemary and lavender in the garden with breathtaking views of the Val d'Orcia. Rediscover your true nature among the pristine fields and olive trees: here, walks and bike rides have no limits! Ready to create memories that will last a lifetime?

Outdoor spacesPetsBathroom

A small wooden table set for two is adorned with fine china cups and a delicate flower vase. The balcony offers a panoramic view of the rolling hills, as the sun sets, casting warm hues over the landscape.

4.91 out of 5 average rating, 309 reviews

I Tramonti di Eramo, Montepulciano centro.

Welcome to Montepulciano, the jewel of the Tuscan hills! Our apartment in the heart of the historic center offers breathtaking views of the surrounding countryside, providing an authentic and unforgettable experience. Step outside and savor the historic atmosphere of Montepulciano. Just a few steps away, you will find the extraordinary Piazza Grande, excellent restaurants, and all kinds of services. Tuscany awaits you for a unique experience.

WalkabilityDecorBathroom

Vacation home in Monticchiello

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.

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 spacesPetsSleep quality

Popular amenities for Montepulciano pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.97 out of 5 average rating, 198 reviews

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

Casa al Gianni - The Simignano Barn

Outdoor spacesWalkabilityQuiet

4.98 out of 5 average rating, 220 reviews

A shaded outdoor terrace features a wooden pergola draped with green vines. A round table is set with a potted plant at its center, surrounded by several chairs. Stone paths lead to the entrance of the house, framed by blooming flowerbeds.

Home in Siena

Secret Garden Siena

PetsWalkabilityParking

4.99 out of 5 average rating, 273 reviews

A rustic living area features a wooden table surrounded by two elegant armchairs and a beige sofa. A stone fireplace, stocked with logs, stands as a focal point, while wooden beams adorn the ceiling. An inviting atmosphere is created by warm, natural colors and soft furnishings.

Home in Anghiari

Casa Rosmarino Eco-Wellness Country Home

WalkabilityOutdoor spacesView

Superhost

A serene bedroom features a spacious bed with a simple white coverlet. A wooden chair with a striped cushion is placed beside a bench. Natural light filters through the two wooden windows, revealing views of the lush vineyards outside.

Home in Castelnuovo Berardenga

4.9 out of 5 average rating, 135 reviews

The Chianti window

PetsOutdoor spacesFamily

4.97 out of 5 average rating, 112 reviews

A rustic stone house is surrounded by lush greenery, featuring wooden shutters and a tiled roof. A shaded outdoor dining area is visible, complemented by potted plants. The serene garden setting invites relaxation and enjoyment of the natural landscape.

Home in Torreone Cortona

Tuscany House | View Breathtaking

PetsWalkabilityHiking

4.87 out of 5 average rating, 134 reviews

A bright, open living space is featured with a spacious bed adorned with a plaid blanket. Light blue cabinetry and a small dining table create a cozy kitchen area. Exposed wooden beams add character to the ceiling, while a television is mounted on the wall.

Home in Montepulciano

Iole's little house

WalkabilityNearbyAccess

4.95 out of 5 average rating, 222 reviews

A spacious bedroom features a large bed with a floral coverlet. Natural light enters through two windows, accentuated by wooden shutters. A pink chair and small desk are positioned against one wall, while a decorative rug adds warmth to the wooden floor.

Home in Monticchiello

La casa nel Borgo - Superior Tuscany Apartment

PetsWalkabilityNearby

Home in Castiglione d'Orcia

A spacious living area features a gray sofa adorned with patterned cushions. A rustic wooden table and bookshelves filled with books are visible in the background, illustrating an inviting open layout that connects the living space to the dining area.

4.96 out of 5 average rating, 179 reviews

Apartment in a detached villa - Val d'Orcia

PetsOutdoor spacesBackyard

Pet-friendly home rentals with a pool

The image depicts a serene swimming pool surrounded by sun loungers and umbrellas, set against a backdrop of lush greenery and the distant Monte Amiata. The clear water reflects the sky, offering a tranquil atmosphere for relaxation and enjoyment.

4.95 out of 5 average rating, 104 reviews

Unique view 3 bdr villa with pool & A/C in Pienza

WalkabilityOutdoor spacesWifi

A warm and inviting open space features a wooden dining table surrounded by chairs, illuminated by natural light from several windows. A red sofa is positioned nearby, while a television and kitchen appliances, including a stove and oven, are visible in the background.

4.93 out of 5 average rating, 129 reviews

Casa Crociani - Amazing Pool & Free Parking

WalkabilityOutdoor spacesDecor

4.96 out of 5 average rating, 169 reviews

A traditional stone casale is set among lush greenery, featuring wooden shutters on the upper windows. Olive and fruit trees frame the home, enhancing its natural setting. A well-maintained lawn extends around the property, inviting relaxation in this peaceful environment.

Cabin in Cetona

Poggio dell'orso.Traditional Casale. Amazing views

Outdoor spacesWalkabilityPool

4.97 out of 5 average rating, 185 reviews

A rustic agriturismo is framed by vibrant greenery and blooming flowers. Outdoor seating is provided by several light-colored chairs and a patterned table. The stone building showcases large windows, which invite natural light into the space, while a welcoming atmosphere is suggested by the well-maintained garden.

Farm stay in Pienza

Spedaletto Castle, Val d'Orcia, Pienza

PetsOutdoor spacesAmenities

An elegant dining area features a solid wooden table surrounded by white chairs, with a decorative cloth placed at the center. The kitchen area, visible in the background, showcases wooden cabinetry, tiled backsplash, and a farmhouse-style sink. Natural light filters through arched windows.

4.83 out of 5 average rating, 145 reviews

La Casa delle Querce - "Policiano"

WalkabilityOutdoor spacesView

4.89 out of 5 average rating, 100 reviews

An aerial view captures the agriturismo's lush green landscape, featuring neatly arranged cypress trees lining the path. A sparkling swimming pool glimmers amidst the foliage, while sprawling fields extend into the background under a clear sky, showcasing the beauty of the Tuscan countryside.

Cottage in Buonconvento

Tuscan Barn Apartment for 6 with panoramic pool

WalkabilityOutdoor spacesAccuracy

Villa in Castiglion Fiorentino

A stone villa surrounded by greenery is featured under a clear blue sky. A large swimming pool reflects the sunlight, complemented by sun loungers and colorful potted flowers along the edges. The outdoor area is perfect for relaxation with scenic views of the Tuscan hills.

4.9 out of 5 average rating, 241 reviews

Tuscan charm of villa - countryside - Villa Senaia

Outdoor spacesPetsDecor

A dog sits in a grassy area, observing the expansive vineyard landscape that unfolds beyond, featuring rolling hills and rows of grapevines under soft morning light.

4.95 out of 5 average rating, 228 reviews

Separate room, between Cortona and Montepulciano

Outdoor spacesPetsPool

Private, pet-friendly home rentals

Cottage in Osteria delle Noci

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.

5.0 out of 5 average rating, 116 reviews

Your Tuscan oak tree house, enchanting Val d'Orcia

PetsOutdoor spacesBiking

4.85 out of 5 average rating, 153 reviews

Villa in Montepulciano

Montepulciano Central Villa – Sauna & Jacuzzi

WalkabilityOutdoor spacesCleanliness

Apartment in Monticchiello

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.

4.97 out of 5 average rating, 187 reviews

Casa Bonari - a paradise for the eyes

Outdoor spacesPetsLaundry

4.94 out of 5 average rating, 219 reviews

The living area features a combination of a soft beige sofa set and two armchairs, arranged around a small round table. A traditional area rug enhances the space, while a stone wall adds texture. A flat-screen television is mounted on the wall near a low cabinet.

Condo in Montepulciano

HOLIDAY APARTMENT IN HISTORICAL PALACE- MARINA

Outdoor spacesPetsCondition

A well-maintained garden area is featured, showcasing a barbecue grill, picnic tables, and lounge chairs under a shaded canopy. Verdant olive trees and rolling hills can be seen in the background, with a distant view of the historic town above.

4.97 out of 5 average rating, 167 reviews

Agriturismo Pescaia Montepulciano Appartamento 2

PetsWalkabilityCheck-in

4.92 out of 5 average rating, 188 reviews

A private terrace is visible, adorned with vibrant flowers and a small table set for two. A bottle of wine and two glasses are elegantly placed, inviting relaxation with a view of the terracotta rooftops and the distant landscape under a pastel sky.

Condo in Montepulciano

Amazing Apartment near Piazza Grande w/ Terrace

PetsWalkabilityCleanliness

Villa in Chianciano Terme

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.

4.97 out of 5 average rating, 130 reviews

Charming Villa in Montepulciano for Fam & Friends

Outdoor spacesWalkabilityValue