Pet-friendly holiday rentals in Cavriglia

4.97 out of 5 average rating, 194 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

Transformed from a former barn, this luxurious retreat offers 5 bedrooms, 4 bathrooms, a large, fully equipped kitchen, a spacious living room, and a large private garden with parking, a hot tub, a patio with sofas, a BBQ, a fire pit, and an outdoor kitchen. Ideal for those seeking a unique experience, it combines rustic charm with modern comforts. Perfect for families or groups, it promises magical evenings under the stars, complete with relaxation in the hot tub and al fresco dining. A memorable getaway awaits you in this slice of paradise!

PetsOutdoor spacesHospitality

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

Entire upper floor of the newly renovated Manor House in traditional Tuscan style. High ceilings with exposed beams make the place cozy and perfect for families or groups of friends. In the house, there are two large functional fireplaces (in the living room and kitchen). Private, non-shared accommodation. The house has a large covered terrace, garden with sofas, BBQ, fire pit, private parking. The swimming pool among the olive trees and vineyards is ideal for relaxation and has private access to the shared area

Outdoor spacesWalkabilityBathroom

4.93 out of 5 average rating, 254 reviews

4.88 out of 5 average rating, 338 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

PetsWalkabilityBackyard

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.

Outdoor spacesPetsLayout

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

ID Code: 051025 AAT 0017 Wisely renovated 1600 exclusive original tuscanian stone house, superbly positioned up on a hill in total privacy. This villa is placed in a real postcard with a 360˚ view. Just 30 minutes drive from Cortona and less than 10 minutes drive from A1 Monte San Savino motorway exit, the villa is reachable through a boulevard flanked by secular trees and it boasts a stunning view on the Valdichiana valley with its towns and villages such as Monte San Savino and Cortona.

Outdoor spacesWalkabilityAmenities

4.99 out of 5 average rating, 113 reviews

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 about an 8-minute drive from the center of Greve in Chianti, in the area of Casole, in the heart of the beautiful Chianti countryside. The villa is located in a quiet and peaceful area, on a small farm surrounded by vineyards and olive groves, where guests can enjoy nature and the typical Tuscan landscapes. The location is ideal for those who want to relax in the countryside but at the same time be close to the center of Greve in Chianti.

PetsOutdoor spacesLocation

4.85 out of 5 average rating, 179 reviews

4.93 out of 5 average rating, 152 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.

PetsOutdoor spacesGetting around

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.

Outdoor spacesPetsIndoor spaces

4.9 out of 5 average rating, 133 reviews

Cottage in San Casciano In Val di Pesa

The jacuzzi is featured outdoors, illuminated with blue lights, creating a calming atmosphere at night. The surrounding stone walls provide privacy, and a dining table can be seen nearby. Steam rises, indicating the water is warm and inviting.

Il Fienile, Cottage in the country with Jacuzzi

Surrounded by wineyards, close to Florence, a charming accomodation in a cozy cottage with heated jacuzzi at your exclusive use. Perfect starting point to discover Florence and Siena. Kitchen, wide living room, bathroom, two double bedroom (one with an extra single bed). In the living room a sofa bed for other 2 people. Tasteful furniture, Air Conditioning, barbecue, private parking. Partnership for: bike rental, private chef, private driver

PetsOutdoor spacesBreakfast

4.96 out of 5 average rating, 194 reviews

4.89 out of 5 average rating, 307 reviews

Villa in Siena

Villa Capanna, Private Pool, Breathtaking Views

Ancient restored barn with up to 6 bedrooms and 6 bathrooms, immersed in a historic wine estate, just 6 km from Siena. One of the most beautiful views that the Tuscan panorama can offer, airconditioned bedrooms, exclusive swimming pool, large triple garden, BBQ, poolside table, terrace to enjoy the sunset over the medieval towers on the horizon while sipping the organic wines of the estate, fireplace, parking free, WI-FI internet.

WalkabilityOutdoor spacesCleanliness

4.95 out of 5 average rating, 219 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.

Outdoor spacesWalkabilityBreakfast

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!

WalkabilityPetsBathroom

4.89 out of 5 average rating, 339 reviews

Popular amenities for Cavriglia pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.86 out of 5 average rating, 101 reviews

A bright living area features a wooden coffee table at its center, flanked by a light-colored sofa and a darker green couch. Two windows with wooden shutters offer views of the surrounding vineyards, while exposed wooden beams add character to the ceiling.

Home in Greve in Chianti

Country Rentals - La Canonica

WalkabilityOutdoor spacesLayout

Home in Barberino Tavarnelle

Nada Home

PetsWalkabilityValue

4.87 out of 5 average rating, 215 reviews

Home in Barberino Tavarnelle

The exterior of the country house is framed by tall, narrow cypress trees and well-maintained gardens featuring various plants. A terracotta pot stands prominently, and gravel pathways lead to the entrance, which is characterized by stone walls and an arched doorway.

Casa Al Poggio in Chianti Shire

WalkabilityOutdoor spacesDecor

4.96 out of 5 average rating, 330 reviews

4.83 out of 5 average rating, 166 reviews

A charming stone farmhouse is showcased, featuring traditional architecture with a tiled roof and multiple windows. A wheelbarrow filled with flowers is positioned on the grassy front lawn, complemented by potted plants and an outdoor light fixture, enhancing the rural setting.

Home in Quercegrossa

Farmhouse in Chianti, Siena Tuscany

WalkabilityOutdoor spacesAccuracy

4.98 out of 5 average rating, 218 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

WalkabilityPetsWi-Fi

4.8 out of 5 average rating, 158 reviews

A shaded outdoor area features a table surrounded by several chairs on lush green grass. A reclining sculpture is visible in the background, alongside trees that provide dappled sunlight across the scene. Rolling hills are seen in the distance, enhancing the natural setting.

Home in Casole d'Elsa

House in Heart of chianti

WalkabilityOutdoor spacesValue

Home in Rignano sull'Arno

A rustic two-story structure is framed by lush greenery, showcasing stone and brick elements. Windows are adorned with decorative iron bars and window boxes, adding character. The inviting exterior is complemented by a blue sky and gentle hillside, creating a serene countryside setting.

LA CASA DELL' AMBRA-ANCIENT BARN RENOVATED-

WalkabilityPetsBreakfast

4.92 out of 5 average rating, 157 reviews

4.96 out of 5 average rating, 121 reviews

A tranquil terrace is surrounded by vibrant greenery, featuring a wooden table set for dining. Soft sunlight bathes the area, casting gentle shadows. The expansive view showcases rolling hills and distant mountains, creating a serene backdrop for outdoor relaxation.

Home in Pontassieve

The charming cottage in Tuscany with breathtaking views

PetsOutdoor spacesQuiet

Pet-friendly home rentals with a pool

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

Outdoor spacesKitchenView

4.99 out of 5 average rating, 123 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

WalkabilityOutdoor spacesHot tub

4.9 out of 5 average rating, 240 reviews

Holiday home in Panzano in Chianti

The image captures a serene outdoor setting featuring a swimming pool surrounded by a well-maintained lawn. Several sun loungers positioned around the pool invite relaxation, while the rustic house and lush greenery complete the idyllic scene.

Fienile Santa Teresa

WalkabilityOutdoor spacesBackyard

4.98 out of 5 average rating, 174 reviews

Holiday home in Dimezzano

[Authentic StoneHouse]Jacuzzi & Viewpool Apartment

WalkabilityOutdoor spacesAccess

4.89 out of 5 average rating, 320 reviews

4.97 out of 5 average rating, 246 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

WalkabilityOutdoor spacesLocation

4.88 out of 5 average rating, 201 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

Outdoor spacesPetsBarbecue

4.86 out of 5 average rating, 275 reviews

A serene pool area is highlighted by lounge chairs set along a stone terrace. The water reflects a golden sunset, providing a tranquil atmosphere. Surrounding greenery adds to the natural beauty, creating a peaceful environment for relaxation.

Apartment in La Presura

Countryhouse 9 kms to Florence-3+2,free park, wine

PetsWalkabilityIndoor spaces

4.94 out of 5 average rating, 97 reviews

A serene outdoor space features a large, clear swimming pool surrounded by carefully manicured hedges and tall trees. The rustic stone house stands in the background, complemented by a few lounge chairs near the pool, offering a peaceful setting for relaxation.

Home in Cavriglia

Wonderful country house

WalkabilityPetsLayout

Private, pet-friendly home rentals

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

Outdoor spacesPetsComfort

4.98 out of 5 average rating, 274 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

WalkabilityOutdoor spacesLaundry

4.88 out of 5 average rating, 126 reviews

4.98 out of 5 average rating, 113 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

Outdoor spacesWalkabilityCleanliness

4.92 out of 5 average rating, 331 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

Outdoor spacesPetsQuiet

Home in Barberino Tavarnelle

beautiful farmhouse in the Chianti region with panoramic garden

Outdoor spacesGetting aroundBathroom

4.96 out of 5 average rating, 47 reviews

4.98 out of 5 average rating, 52 reviews

A rustic stone house stands with warm lighting illuminating its facade. The building features various window styles and a large, wooden front door. Lush green grass surrounds the property, and a friendly dog is seen resting nearby.

Home in Cavriglia

La Casa del Briga

PetsOutdoor spacesFamily

Farm stay in San Giovanni Valdarno

A shaded terrace features a wrought iron table and two chairs, overlooking a lush garden. Greenery encompasses the area, with a gazebo in the distance and vibrant foliage outlining the space, all under a clear blue sky.

Tuscan Farmhouse between Chianti & Florence

WalkabilityOutdoor spacesCheck-in

4.84 out of 5 average rating, 62 reviews