Pet-friendly vacation rentals in San Gimignano

The open-plan living area features wooden beams across the ceiling. Natural light filters through multiple windows, illuminating the cozy seating and dining areas. A rustic stone wall adds character, while a wooden table and light-colored chairs provide a functional dining space.

4.96 out of 5 average rating, 239 reviews

Casa Irene

Casa Irene è un delizioso appartamento in stile Toscano, situato al secondo ed ultimo piano di una palazzina a soli 5 minuti a piedi dal centro,50 mt per porta San Matteo ed altri 50 mt per la via Francigena. Data la posizione defilata si raggiunge facilmente in auto per parcheggiare nell'immediato parcheggio libero. L'appartamento dotato di wifi ed aria condizionata si suddivide in sala/cucina openspace,camera e bagno con doccia ed un terrazzo abitabile con affacci sulle mura di San Gimignano

The image showcases a view of the Torre del Diavolo framed by lush greenery. Two bottles of wine are positioned in the foreground, enhancing the peaceful garden setting. Historic buildings with textured stone facades are visible, complementing the charming medieval atmosphere.

4.98 out of 5 average rating, 153 reviews

Apartment at ground floor with garden

A refined and very central setting, between Piazza della Cisterna and Piazza del Duomo. The house has the rare value of combining a comfortable ground floor, with independent entrance, to a stunning view of the famous Devil's tower.The exclusive garden, equipped to dine outdoors, read or stay between flowers and towers, is an extraordinary oasis of peace and silence, just around the corner of the two lively main squares.Possibility of parking in a private box for a fee at a cost of €8.00 x day.

4.95 out of 5 average rating, 265 reviews

An aerial view of the historic Monteriggioni Castle showcases its medieval architecture surrounded by lush countryside. The fortified walls encircle the village, which is dotted with trees and buildings, while rolling hills extend into the distance under a sunset sky.

Cottage in Monteriggioni

Monteriggioni Castello, holiday house in Tuscany

Il nostro alloggio è un edificio storico che risale alla costruzione del castello. È stato recentemente restaurato e arredato con cura in tutti i dettagli. È molto accogliente e dispone di tutti i più moderni servizi. I turisti che decideranno di essere nostri ospiti, avranno il vantaggio di vivere nell' ambiente medievale del castello, usufruendo di tutti i confort. Si sentiranno coccolati e avranno l'opportunità di tornare indientro vivendo un' esperienza unica e indimenticabile.

4.91 out of 5 average rating, 235 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

Ciao, siamo Cristina & Carmelo! Vi invitiamo a vivere un’esperienza autentica nel nostro agriturismo “Casa al Gianni” situato 20 min da Siena. Il nostro marchio è la vita semplice a stretto contatto con la natura e gli animali della nostra fattoria. Immerso tra i boschi e la splendida campagna toscana trascorrerai una vacanza indimenticabile. Questo angolo di paradiso ti rimarrà nel cuore!

Home in Tavarnelle Val di Pesa

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.

4.96 out of 5 average rating, 310 reviews

Casa Al Poggio & Chianti view

Casa al Poggio is a typical country house of Chianti area is spread in 145 square meters on two floors, the ground floor is a large living area, with kitchen and sofa ,fireplace ,up stairs there is 2 large double bedrooms and a sofa bed in the middle open room , always setable as 2 singles or a double bed bed and a relaxing bathroom with shower and bath with Chianti view.

Vacation home in Peccioli

A spacious living area features a light-colored sofa with a decorative throw, complemented by wooden beams overhead. The open kitchen with modern appliances is visible in the background, alongside large windows that provide natural light and a view of the exterior.

4.9 out of 5 average rating, 215 reviews

Michelangelo: entire space in the heart of Tuscany

Come and take a vacation at our beautiful apartment in Peccioli, Tuscany! Enjoy a renovated space, beautifully decorated, with new appliances and furniture, Air conditioner in all spaces, high-speed internet, and all you need to enjoy your time in Italy. Peccioli is a gem in the heart of Tuscany, near all the big cities and touristic attractions.

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.

4.88 out of 5 average rating, 117 reviews

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.

Superhost

A warm and inviting fireplace is surrounded by various decorative elements, including potted plants and wall art. Baskets filled with logs are neatly arranged, enhancing the cozy ambiance. Natural light enters through nearby windows, creating a bright and comfortable space.

Home in Tavarnelle Val di Pesa

4.89 out of 5 average rating, 173 reviews

La Casa di Nada Home

My house is immersed in the Tuscan countryside among olive trees and vineyards in the heart of Chianti, wonderful views, relaxation, I offer cooking schools and exclusive dinners, my garden can be the perfect setting for a wonderful candlelit dinner prepared exclusively for my guests 🤗

Villa in Tavarnelle Val di Pesa

A serene pool area is featured, surrounded by well-maintained greenery. Several lounge chairs are positioned along the pool's edge, inviting relaxation. The sky is clear and blue, complementing the tranquil setting of the property.

4.94 out of 5 average rating, 164 reviews

Podere Guidi

Appartamento in Villa panoramica tra Firenze e Siena, nel cuore del Chianti, in un borgo incantevole. Piscina aperta da maggio a fine settembre. Dal 2026 la piscina sarà aperta dalle ore 9 alle 13 con utilizzo esclusivo per gli ospiti in questo orario.

4.84 out of 5 average rating, 256 reviews

A well-equipped kitchen is featured, highlighted by earthy green cabinetry and a tiled countertop. A wooden dining table with matching chairs is positioned nearby. An arched doorway leads to a separate room, while ample natural light enters through the windows, emphasizing the warm tones of the tiled flooring.

Condo in San Gimignano

Historic centre - cozy apartment

Beautifully renovated apartment located in the heart of the historic center , near the Porta San Matteo. The apartment consists of: fully equipped kitchen, double bedroom with air conditioner, bathroom and small terrace. Free wi fi Many parkings are nearby

Vacation 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.

4.92 out of 5 average rating, 111 reviews

Stunning Tuscan apartment for 2

This apartment - tucked away privately and enjoying a stunning view from its terrace - is part of an 'agriturismo' farm which produces organic Chianti Classico. Spacious and light, it has 1 double bedroom, 1 sitting room, 1 bathroom and a kitchen.

4.84 out of 5 average rating, 230 reviews

A stone cottage is nestled amidst a lush green lawn, surrounded by flowering shrubs. The structure features a classic design with a tile roof and large windows. A clear sky enhances the serene garden setting, providing a peaceful and inviting environment.

Cottage in San Gimignano

Countryside Cottage With View - Le Rondini apt

The cottage is part of a charming traditional Tuscan farmhouse, built in stone and situated in one of the most beautiful areas of Tuscany.A lovely garden surrounds the house and has magnificent views of the medieval town with its famous towers.

Popular amenities for San Gimignano pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.99 out of 5 average rating, 186 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

Amore in Chianti

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.

4.97 out of 5 average rating, 116 reviews

Torretta Apartment

4.92 out of 5 average rating, 143 reviews

A shaded outdoor dining area features a large table surrounded by several chairs, nestled under a pergola with lush greenery. The shared swimming pool glistens in the background, framed by terracotta tiles and scenic views of the Tuscan landscape.

Home in San Miniato

Private villa/swimming pool in Tuscany

4.99 out of 5 average rating, 172 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

4.91 out of 5 average rating, 155 reviews

A spacious garden area is featured, framed by trees and manicured grass. A sun lounger is positioned beneath the shade of a tree. The building in the background showcases arched windows and red shutters, enhancing the outdoor setting.

Home in San Gimignano

Historic house in heart of Tuscany

4.95 out of 5 average rating, 237 reviews

Home in San Gimignano

House in Tuscany: San Gimignano view

Home in Tavarnelle Val di Pesa

A bright living area is highlighted by a white sectional sofa, complemented by red throw pillows. An elegant area rug sits on terracotta tiles, with wooden beams and a staircase leading to the upper level visible. Light streams through a window, enhancing the warm atmosphere.

4.94 out of 5 average rating, 109 reviews

Suite Casa Luigi con piscina esclusiva

4.97 out of 5 average rating, 186 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

Pet-friendly home rentals with a pool

Villa in Montecatini Val di Cecina

A historic tower rises prominently against a blue sky dotted with fluffy clouds. Surrounding greenery complements the stone structure, with trees and small buildings visible along the hillside, collectively conveying a sense of tranquility.

4.99 out of 5 average rating, 129 reviews

Torre dei Belforti

Villa in Monteroni d'Arbia

A heated mini hydro-massage pool is surrounded by greenery, featuring subtle chromotherapy lighting in shades of purple. In the background, a rustic farmhouse is set against a serene twilight sky, with tall cypress trees lining the space.

4.98 out of 5 average rating, 107 reviews

San Giovanni in Poggio, villa Meriggio 95mq

4.91 out of 5 average rating, 323 reviews

An aerial view of a beautiful countryside property is shown, featuring a stone farmhouse surrounded by lush greenery, gardens, and vineyards. A shared swimming pool is visible, along with outdoor seating areas and well-maintained landscaping that highlights the tranquil rural setting.

Apartment in Gavignano

holidays with swimming pool in Tuscany

Apartment in Gambassi Terme

A swimming pool with clear blue water is featured, accompanied by a large pink inflatable flamingo. Several sun loungers are arranged around the pool area, surrounded by greenery and trees, providing a relaxed outdoor atmosphere.

4.97 out of 5 average rating, 216 reviews

La Fabbrichina

Farm stay in San Casciano In Val di Pesa

A dining table is set under the shade of lush trees, featuring a bottle of wine and glasses. The surrounding garden is filled with tall cypress trees and vibrant greenery, creating a serene atmosphere for outdoor dining.

4.78 out of 5 average rating, 163 reviews

Sperone: two floors apartment with pool

4.94 out of 5 average rating, 195 reviews

A well-kept garden features neatly trimmed grass and a variety of trees, including tall pines, providing shade and a natural atmosphere. A subtle hammock is visible between two trees, inviting relaxation in the serene outdoor space.

Villa in Montespertoli

Colonica nel Chianti

4.95 out of 5 average rating, 209 reviews

A rustic dining area features a large wooden table set for meals, complemented by transparent chairs. A cozy fireplace, built into a stone wall, adds warmth to the space. Soft lighting is provided by hanging fixtures, enhancing the inviting atmosphere.

Apartment in Sorana

Casa Gave - Nature and relax in Tuscany

4.98 out of 5 average rating, 113 reviews

A sunlit pool area features a spacious salt-water pool with a surrounding deck. Several lounge chairs are arranged with umbrellas, providing shaded seating. A rustic stone building serves as a backdrop, displaying traditional Italian architectural elements and large windows that invite natural light.

Villa in Orentano

Villa Gourmet Food, Pizza, Chef, Pool and Nature

Private, pet-friendly home rentals

4.97 out of 5 average rating, 77 reviews

A stone cottage is surrounded by lush greenery, featuring a rustic facade with wooden accents. Potted plants are placed near the entrance, and the roof is topped with a small chimney. A pathway of stones leads to the door, inviting guests to explore.

Cottage in San Gimignano

Romantic House in Tuscany with jacuzzi

4.93 out of 5 average rating, 149 reviews

A sweeping view of lush vineyards stretches across gentle hills, blanketed in morning mist. Soft hues of gold and green are present, with a clear sky above. The serene landscape conveys a sense of tranquility and natural beauty.

Condo in San Miniato

Renaissance Residence In San Miniato with a view

A window draped with light, flowing curtains frames a view of distant hills and town rooftops. A small table holds stacked books, a pair of glasses, and a coffee cup with a cookie, creating a serene reading nook.

4.93 out of 5 average rating, 74 reviews

Cozy 18th century house

4.92 out of 5 average rating, 145 reviews

The exterior of the property features a rustic stone façade complemented by wrought iron details. A spacious terrace is equipped with a large umbrella and an outdoor dining area, surrounded by lush greenery, enhancing the natural setting.

Cottage in Radicondoli

Splendido fienile ristrutturato in Toscana

Historic architecture is prominently displayed in the square, featuring stone buildings with arched doorways and textured walls. A clock is visible near a stone pillar, while people gather in the space, enjoying the atmosphere under a partly cloudy sky.

5 out of 5 average rating, 37 reviews

L'Attico dei Sogni

Home in Barberino Tavarnelle

5 out of 5 average rating, 32 reviews

To be happy in Tuscany with comfort & view!

Farm stay in San Gimignano

An aerial view of a large swimming pool is surrounded by lush green grass. Sun loungers with umbrellas are placed around the pool, providing ample space for relaxation. The area is well-maintained, with pathways leading to different outdoor sections.

5 out of 5 average rating, 29 reviews

Casa Renai - vacanze con amici a San Gimignano