Pet-friendly vacation rentals in Gaiole in Chianti

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.

4.93 out of 5 average rating, 224 reviews

The Farmhouse Cottage

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

4.97 out of 5 average rating, 175 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.

4.86 out of 5 average rating, 212 reviews

A spacious bed is dressed in soft white linens, complemented by decorative pillows. Two bedside tables with lamps stand on either side, providing gentle illumination. The walls feature warm tones and framed artwork, contributing to a calming and serene atmosphere.

Home in Rietine

Gaiole in Chianti Poggio Casabianca

We invite you in the heart of Chianti area. Poggio Casabianca is a little family homestead located in the Chianti Classico region exactly in the hearth of Tuscany. The owners live here and they offer at their guests an apartment with a big living room-kitchen with a big door that open directly to the garden, a bathroom with shower and a confortable doublebed room. Outside in the garden ther is a pool, shared with the owner, where you can refreshing and relaxing during the summer.

Villa in Monteroni d'Arbia

A sunlit swimming pool is situated in an expansive landscaped area, surrounded by neatly trimmed grass and lush trees. The charming building stands in the background, showcasing traditional architecture, while cypress trees line the horizon, adding to the tranquil countryside atmosphere.

4.98 out of 5 average rating, 102 reviews

San Giovanni in Poggio, villa Meriggio 95mq

Detached house, two double bedrooms, two bathrooms with shower, living room with fully equipped kitchen (dishwasher, washing machine, oven, microwave), double sofa bed, private garden with equipped pergola. Satellite TV and free Wi-Fi. Additional services at the property, upon reservation, include Focus brand Jarifa2 6.7 pedal-assisted bicycles and a wellness area with a Forest outdoor Finnish sauna and a heated mini-pool with hydromassage and chromotherapy with panoramic views.

4.99 out of 5 average rating, 237 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

Price includes the WELLNESS & COMFORT package as follow: - Organic Wooden Fired Hot Tub w/Jacuzzi (1 water filling good for 4 days of use) - Infrared Sauna - Wood for Fireplace & Hot Tub - Fire starters - Heating/Air Conditioning - Laundry/Dryer - Shower Gel/Shampoo/Bathrobes - Welcome Appetizer w/Wine - Italian Ground Coffee - Treats during your stay Extra activities (not included) : - Massages, Cooking Classes, Tours & Tasting Please INQUIRE for price & availability.

4.92 out of 5 average rating, 131 reviews

A charming country house is set against a backdrop of expansive blue sky and lush green hills. The exterior features a combination of stone and plaster, with large arched windows and a welcoming entrance. A pebbled path leads to the front, flanked by garden beds.

Home in Il Poggetto

The Loggia

Country house located in Radda, the heart of the Chianti, within walking distance from the historical center and other services such as; Coffee shops, Post Office,grocery stores and restaurants. The house is composed of a full equipped kitchen, living room with a sofa bed, bedroom, loggia and bathroom. The property is surrounded by a garden and there is a nice wooden table in the garden to eat in an open space and another lounge spot to enjoy the magnificent landscape.

Guest suite in Greve in Chianti

A charming stone farmhouse is set within a lush garden, surrounded by vibrant red flowers and greenery. The building features wooden window shutters and a tiled roof, blending harmoniously with the natural landscape under clear blue skies.

4.97 out of 5 average rating, 399 reviews

Selvabella in Chianti B&B Il Riccio

Selvabella is a farmhouse situated in the heart of Tuscany, half way between Greve and Panzano in Chianti. Just 35 km from Florence and Siena it is a perfect place to enjoy the beauty of Chianti. Il Riccio is an apartment of 45 square meters. It has a double bedroom, a living-room/bedroom with two sofas/ single beds, a large bathroom and a kitchenette (fridge, sink, small oven and 2 buners gsafire). It is the perfect place for lovers of nature, cooking and pottery.

Apartment in Castelnuovo Berardenga

A historic villa is situated amidst lush, rolling hills, surrounded by vineyards. The exterior features a traditional stone facade, large windows, and terracotta roof tiles. Manicured gardens with circular patterns enhance the property's charm, complemented by tall cypress trees framing the serene landscape.

4.93 out of 5 average rating, 164 reviews

Villa di Geggiano - Perellino Suite

The 700 years old Villa di Geggiano, surrounded by our working vineyard and lovingly maintained gardens, is located in Chianti in Tuscany which is one of the most beautiful regions of Italy. Our guesthouse is located in one of the original garden pavilions of the villa. PLEASE NOTE THAT WE ARE IN THE COUNTRYSIDE WITH VERY FEW PUBLIC TRANSPORT OTHER THAN TAXI SO THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A RENTAL CAR.

4.9 out of 5 average rating, 209 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 - Capanna

Hi, we're Cristina & Carmelo! We invite you to live an authentic experience in our farmhouse “Casa al Gianni” located 20 minutes from Siena. Our hallmark is simple life in close contact with nature and the animals of our farm. Immersed in the woods and the beautiful Tuscan countryside, you will spend an unforgettable vacation. This slice of paradise will remain in your heart!

Farm stay in Gaiole in Chianti

A spacious bedroom features a large bed adorned with soft linens and two neatly rolled towels. Warm terracotta tiles cover the floor, complemented by pale yellow walls and wooden beam ceilings. Natural light fills the room through two windows with dark shutters, creating a calming ambiance.

4.94 out of 5 average rating, 236 reviews

Il Nido - a romantic hearth

Lui non esisteva, è stato ricavato in un angolo della grande casa in cui chissà quante persone della stessa famiglia vivevano. Per questo è diventato il nostro piccolo Nido, la casa da cui partire per scoprire il borgo. Non un piano ma addirittura due, con tanto cotto, legno e colori caldi.

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Popular amenities for Gaiole in Chianti pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

5 out of 5 average rating, 162 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

4.95 out of 5 average rating, 478 reviews

An outdoor area features a quaint seating arrangement with a small table and four chairs, nestled under the shade of a rustic covered porch. Surrounding planters hold vibrant flowers, and a brick well adds charm to the lush green lawn.

Home in Cerreto Guidi

Casa del Giardino

Home in Figline e Incisa Valdarno

Well-maintained gardens feature a lush lawn surrounded by mature trees, providing shade. An old stone building is visible in the background, characterized by arched windows and a terracotta roof. A shaded outdoor seating area, under a rustic wooden eave, adds to the inviting exterior.

4.96 out of 5 average rating, 108 reviews

Torretta Apartment

4.88 out of 5 average rating, 66 reviews

A dining area features a wooden table surrounded by high-backed chairs, complemented by natural light filtering through a window. The kitchen space displays a marble countertop, a modern sink, and overhead shelves showcasing diningware. Exposed wooden beams add a rustic touch to the ceiling.

Home in Certaldo

Paluffo Tower House

Home in Gaiole in Chianti

A spacious living area features a wooden-beamed ceiling and large windows allowing for natural light. A red sofa and rustic wooden table create a comfortable setting. A stone fireplace is positioned in the corner, adding a warm element to the welcoming environment.

4.8 out of 5 average rating, 101 reviews

loft in the heart of Tuscan Chianti

4.97 out of 5 average rating, 173 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

5 out of 5 average rating, 127 reviews

A cozy sitting area features a vintage leather sofa with colorful accents, positioned against a light wall adorned with contemporary wall art. Soft bedding is seen at the back, complemented by warm wooden flooring. Natural light filters through a nearby window, enhancing the inviting space.

Home in Montalcino

Montalcino Townhouse with Private Garden & Spa

Home in Castelnuovo Berardenga

A rustic stone building is surrounded by green grass and vibrant flower pots filled with white and purple blooms. Tall cypress trees are visible in the background, under a clear blue sky, enhancing the peaceful Tuscan landscape.

4.91 out of 5 average rating, 205 reviews

Bed and Breakfast CASA CERNANO

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Pet-friendly home rentals with a pool

4.95 out of 5 average rating, 91 reviews

A spacious bedroom features a large bed adorned with soft linens. Natural light enters through a window, complemented by warm lamplight. Stone walls and wooden beams add rustic charm. A dresser and side table provide functional decor, and framed images line the walls, enhancing the elegant atmosphere.

Apartment in Pogi

Borgo Iesolana Suite Superior

4.93 out of 5 average rating, 83 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

Villa in Radda in Chianti

An aerial view of a lovely bungalow surrounded by lush greenery. A private swimming pool is situated in front of the house, accompanied by elegantly arranged sun loungers. The stone façade of the bungalow is complemented by a tiled roof and vibrant flower pots framing the entrance.

5 out of 5 average rating, 5 reviews

La Casa di Radda

4.98 out of 5 average rating, 211 reviews

Farm stay in Sovicille

La Villa farm stay - L'Olivo, Pool & Hot Tub

4.97 out of 5 average rating, 155 reviews

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.

Vacation home in Panzano

Fienile Santa Teresa

Apartment in Gaiole in Chianti

4.61 out of 5 average rating, 18 reviews

Cozy studio in Chianti with use of swimming pool

4.94 out of 5 average rating, 134 reviews

A scenic view of a stone house surrounded by greenery shows a shared pool area with sun loungers and an umbrella. Olive trees dot the landscape, providing a serene backdrop of the Tuscan countryside.

Hut in Poggibonsi

Lovely barn with pool between Siena and Florence

Farm stay in Loro Ciuffenna

A panoramic view of a bright swimming pool surrounded by a lush garden. Comfortable lounge chairs are arranged on the stone patio. Olive trees and shrubs create a natural backdrop, emphasizing the serene outdoor setting under a clear blue sky.

4.99 out of 5 average rating, 108 reviews

Il Roseto: your Villa in Tuscan Countryside

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Private, pet-friendly home rentals

Condo in Gaiole in Chianti

A serene bedroom features a spacious bed adorned with a patterned duvet. Natural light filters in through a window, which complements the rustic wooden beams overhead. A blue dresser is positioned nearby, while a sleek bathtub is softly illuminated in the corner.

4.91 out of 5 average rating, 33 reviews

Divine Transit Gaiole

4.97 out of 5 average rating, 34 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

5 out of 5 average rating, 13 reviews

An inviting living space features a wooden dining table surrounded by chairs. A cozy daybed with decorative cushions is positioned near a window, providing natural light. Exposed wooden beams and a stone accent wall add warmth to the surroundings, creating a harmonious atmosphere.

Condo in Neri

La Finestra sul Lago in Cavriglia

4.92 out of 5 average rating, 24 reviews

A spacious bedroom is showcased with a large bed dressed in neutral linens, framed by rustic wooden beams overhead. A wooden dresser and bedside tables provide storage, while a rustic coffee table sits centrally on a soft area rug. A chair adds a cozy touch.

Home in Selvole

Chianti House on the woods

Apartment in Radda in Chianti

An inviting living area features a wooden door, a round table with a potted plant, and a warm-toned rug. Walls are lined with shelves and artwork, while a backdrop displays a modern kitchen and a spacious archway leading to additional living spaces.

4.91 out of 5 average rating, 85 reviews

La Casina

4.97 out of 5 average rating, 86 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

5 out of 5 average rating, 25 reviews

A charming stone villa is framed by lush greenery and tall trees. Natural stone pathways lead to the entrance, where wooden shutters are seen beside arched windows. Shadows from the surrounding foliage create a tranquil ambiance, reflecting the serene countryside setting.

Home in Radda in Chianti

Villa le Scope 5*