Pet-friendly holiday rentals in Cavriglia

4.93 out of 5 average rating, 294 reviews

A rustic building is seen under a starry night sky, with a partial roof providing shelter. Soft light glows from the interior, illuminating the entrance. Lush greenery and trees surround the scene, adding depth to the serene nighttime landscape.

Farm stay in Simignano

Casa al Gianni - Hut

Hi, we’re Cristina and Carmelo! We look forward to welcoming you to ‘Casa al Gianni’, our farm stay in the woods of the Montagnola Senese, just 20 minutes from Siena. Here, life slows down: just the scent of the earth, the song of the birds and the companionship of our animals. It’s an invitation to rediscover the beauty of the little things, surrounded by the greenery of the most authentic Tuscany. It’s not just a holiday; it’s a return to our roots. This haven of peace will stay with you in your heart. We look forward to welcoming you!

4.88 out of 5 average rating, 343 reviews

Townhouse in Scandicci

Florence Sunset Hills • Giogoli

Escape to the peaceful hills of Giogoli where authentic Tuscan charm meets breathtaking views of Florence.Just 15 minutes from the city center and the Chianti countryside, this elegant home is the perfect base for exploring Tuscany while enjoying quiet mornings, unforgettable sunsets, and the beauty of the surrounding landscape. Surrounded by nature but close to the region's most iconic spots, it's the ideal retreat for anyone looking for comfort, tranquility, and a genuinely Tuscan experience

4.99 out of 5 average rating, 155 reviews

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

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.

4.95 out of 5 average rating, 107 reviews

The kitchen area features wooden cabinetry and modern appliances, including a microwave and coffee maker. A round wooden table with simple chairs is surrounded by natural light from large windows, offering views of the surrounding vineyards.

Home in Greve in Chianti

Casa Giulia di Sopra Farmhouse

The CASA GIULIA DI SOPRA apartment, renovated in 2022 and located on the first floor, is a portion of an ancient farmhouse located in the heart of Chianti Classico. It is surrounded by the vineyards of Villa Calcinaia, an estate owned by the Capponi Counts since 1524. The apartment is 130 meters away from the shared swimming pool, open from May to October. The apartment has an outdoor area with a table and chairs where guests can dine and enjoy a glass of wine at sunset.

4.93 out of 5 average rating, 155 reviews

Home in Il Poggetto

The Loggia

Immerse yourself in the authentic Tuscan dream. "La Loggia" is a charming home in the heart of Chianti Classico, just 300 meters on foot from the historic center of Radda. It offers the perfect blend of countryside quietness and village convenience, featuring a large private garden with breathtaking panoramic views over vineyards and a beautiful glass-enclosed loggia. The perfect oasis to relax and enjoy the sunset after exploring Siena, Florence, and nearby wineries.

Villa in Greve in Chianti

The exterior of a charming stone villa is showcased, with a refreshing swimming pool in the foreground. Lush green grass surrounds the pool area, and a shaded gazebo with seating is positioned nearby. Rolling hills and a clear blue sky form a picturesque backdrop.

Villa La Doccia, Greve in Chianti

Villa La Doccia is located approximately 8 minutes by car from the centre of Greve in Chianti, in the area of Casole, in the heart of the beautiful Chianti countryside. The villa is located in a quiet, peaceful area, on a small farm surrounded by vineyards and olive groves, where guests can enjoy nature and the typical Tuscan landscape. The location is perfect for those who want to relax in the countryside while still being close to the centre of Greve in Chianti.

4.85 out of 5 average rating, 180 reviews

Farm stay in Loro Ciuffenna

The exterior of the villa is showcased, featuring stone walls and greenery. A spacious stone patio is visible, furnished with a dining table and chairs, surrounded by neatly trimmed bushes and potted plants, creating an inviting space for outdoor gatherings.

Il Roseto: your Villa in Tuscan Countryside

In the heart of Tuscany between Arezzo, Florence and Siena but far away from the bustle of the cities, you will find a pristine landscape where to enjoy nature and relaxing, amazing views and much more for a perfect getaway with your friends or family. A villa of 190 mq with 600 mq garden,where you can enjoy lunch outdoors, have fun making pizza and baking it in the wood- oven, or savour a wonderful barbeque. A comfortable Villa for guests who love being together.

4.99 out of 5 average rating, 124 reviews

Home in Castelnuovo Berardenga

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.

The Chianti window

A wonderful place to spend a few days in pleasant company. A large living room with fireplace where you can relax after returning from beautiful walks, bike rides, and excursions. The independent apartment is 15 km from Siena, 20 km from the Thermal Baths and 40 minutes from the villages of San Gimignano and Monteriggioni. Overall, there is a farm that produces wines and oil with the possibility of guided tours and tasting of our products with themed dinners.

4.9 out of 5 average rating, 136 reviews

4.95 out of 5 average rating, 222 reviews

A spacious living area features a modern design, with a prominent stone fireplace and minimalist furniture. Large glass doors open to a serene outdoor view, while natural light brightens the room, highlighting the soft tones of the walls and furnishings.

Tower in Fiesole

A Big Dream in a Little Tower.

The Tower was created in the late 1800s by an illustrious Englishman, Sir John Temple Leader, in one of the oldest and most important stone quarries belonging to the Medici family. From the same quarry were extracted many important works such as the columns of the Medici chapels, the steps of the Laurenziana library .. all just 5 km from the historic center of Florence.

Holiday home in Castelnuovo Berardenga

A sparkling swimming pool is surrounded by sun loungers and umbrellas, offering a relaxing space for guests. The rustic farmhouse, with its stone exterior, is visible in the background, amidst lush greenery and trees under a partly cloudy sky.

PIERFANTINI private Chianti house ♿️ 🏊‍♂️ 🐶

Pierfantini is a rustic farmhouse. It is located on a hill in the middle of a natural park. Isolated from the vitta, the nearest town is the medieval village of San Gusmè. The house is renovated and the ground floor adapted for disabled people or wheelchair users There are three apartments but I never rent them separately. The house rent is for all the property

4.91 out of 5 average rating, 101 reviews

Farm stay in Castelfranco di sopra

Romantic apartment in the Tuscan village

The house is located in an ancient medieval village that has been completely renovated while maintaining the charm of its history. In the village you will find two swimming pools, a restaurant, many gardens and much more... It is in a strategic position to be able to reach the main attractions such as the Chianti Region, Florence, Arezzo and Siena!

4.89 out of 5 average rating, 345 reviews

Castle in Barberino Tavarnelle

An elegant medieval castle is surrounded by lush olive trees, showcasing its stone façade and characteristic towers. Soft lighting emanates from the windows, creating a warm ambiance as dusk approaches. The castle is set against a backdrop of gently rolling hills, enhancing its historic charm.

Suite in Castello di Valle

A unique experience in a historical dwelling located in the Chianti region. This medieval castle is situated in a strategic position, surrounded by the major Tuscan touristic attractions. The suite is at the entrance floor level: double bedroom with bathroom, sofa bed for two people, kitchenette, fireplace.

4.88 out of 5 average rating, 129 reviews

Popular amenities for Cavriglia pet-friendly home rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.88 out of 5 average rating, 204 reviews

An expansive outdoor deck offers a serene view of rolling hills under a clear sky. An infinity pool transitions seamlessly into the landscape, with two soft seating cushions placed nearby, inviting relaxation and contemplation of the stunning panoramic scenery.

Home in Casale

Infinity view

4.96 out of 5 average rating, 249 reviews

A charming pathway leads to the entrance of the house, surrounded by lush greenery. Flower pots are positioned along the stone walkway, with a seating area visible to the side, inviting guests to enjoy the serene landscape of rolling hills in the background.

Home in Greve in Chianti

Love in Chianti

Home in Barberino Tavarnelle

SuiteLouise.pool, Hot Tub,homeGym & private Garden

4.9 out of 5 average rating, 129 reviews

4.98 out of 5 average rating, 222 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

Home in Barberino Tavarnelle

Nada Home

4.87 out of 5 average rating, 218 reviews

4.99 out of 5 average rating, 187 reviews

The exterior view features a rustic stone house surrounded by greenery, including trees and flowering plants. Sun loungers are positioned on the lawn, creating a space for relaxation. A spacious terrace extends from the house, providing access to the inviting garden area.

Home in Bagno A Ripoli

Tuscany .Countryhouse on the Florence's hills

4.86 out of 5 average rating, 160 reviews

Home in Villa A Sesta

Casa Nataly Chianti - Jeky Stay

4.88 out of 5 average rating, 821 reviews

A unique treehouse is highlighted among vibrant green grass adorned with clusters of purple flowers. Towering trees provide shade, and the structure features a deck that overlooks the surrounding natural landscape, inviting a sense of tranquility and harmony with nature.

Home in Galluzzo

TREEhouse / casaBARTHEL

Pet-friendly home rentals with a pool

Villa in Castellina in Chianti

A spacious kitchen showcases a large stone fireplace with a wooden mantle as its centerpiece. Light streams through the window, illuminating the wooden beams overhead. A dining table is set for a meal, while traditional utensils adorn the walls, enhancing the inviting ambiance.

Manor House - IlVillinoFarmhouse

4.93 out of 5 average rating, 256 reviews

4.89 out of 5 average rating, 311 reviews

Villa in Siena

Villa Capanna, Private Pool, Breathtaking Views

Farm stay in Monte San Savino

A serene pool area is showcased with two sun loungers positioned beside a tranquil salt-water pool. The expansive view of the valley and distant cityscape adds to the peaceful ambiance, while greenery surrounds the space, enhancing the sense of privacy and relaxation.

LUXURY VILLA SALTWATER POOL 35 min FROM CORTONA

4.99 out of 5 average rating, 116 reviews

5.0 out of 5 average rating, 100 reviews

A charming stone cottage is set among lush green hills, featuring large arched windows and a shaded patio area with outdoor seating. Olive trees surround the property, providing a connection to the natural landscape, while a gravel pathway leads to the entrance.

Villa in Sinalunga

The twigs

4.99 out of 5 average rating, 131 reviews

The stone farmhouse features vibrant red shutters and a terracotta roof. A spacious patio area contains a wooden dining set, surrounded by lush green grass and tall cypress trees. The exterior is complemented by well-maintained stone pathways, inviting guests to explore the outdoor space.

Villa in San Leolino

Poggio del Fattore-Villa with pool, hilltop, Chianti

Holiday home in Greve in Chianti

A terrace is showcased, featuring a wooden table accompanied by white chairs. The scene includes expansive views of rolling hills and vineyards, framed by tall cypress trees. The sky reveals warm sunset hues, creating a serene atmosphere.

Stunning Tuscan apartment for 2

4.9 out of 5 average rating, 131 reviews

Holiday home in Dimezzano

[Authentic StoneHouse]Jacuzzi & Viewpool Apartment

4.89 out of 5 average rating, 324 reviews

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.

Tuscan charm of villa - countryside - Villa Senaia

4.9 out of 5 average rating, 241 reviews

Private, pet-friendly home rentals

4.98 out of 5 average rating, 171 reviews

Lush vineyards stretch across rolling hills, showcasing rows of grapevines that lead the eye toward distant mountains. Tall cypress trees line the landscape, creating a serene backdrop that complements the greenery of the vines and the soft contours of the terrain.

Apartment in San Gusmè

La Dimora del Luca

Apartment in Santo Spirito

A light-filled living area features curved ceilings and large arched windows opening to a garden. A comfortable armchair and a striped sofa are arranged around a neutral coffee table. Bookshelves line the walls, displaying an assortment of decorative items and books.

Wonderful house with garden

4.98 out of 5 average rating, 275 reviews

4.97 out of 5 average rating, 117 reviews

The lounge features elegant walls adorned with intricate frescoes and moldings. A large mirror reflects the refined decor. Two white armchairs and a colorful sofa provide seating, while a coffee table rests on a patterned rug before a decorative fireplace.

Apartment in Siena

Luxury frescoed apartment in the historical center

4.98 out of 5 average rating, 294 reviews

Farm stay in Siena

Typical Tuscan Country House WITH A/C

Farm stay in Castelnuovo Berardenga

Apartment in a Tuscan farmhouse at Le Pietre Vive

4.92 out of 5 average rating, 359 reviews

4.92 out of 5 average rating, 338 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

4.88 out of 5 average rating, 230 reviews

Holiday home in Reggello

Barrel Suite Tuscany • Hot Tub • Vineyard View