Pet-friendly holiday rentals in San Gimignano

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!

WalkabilityPetsTV

A vibrant square is depicted, featuring medieval buildings with distinct stone facades. Several people are seen walking through the area, with tables and umbrellas set up for outdoor dining. The historical architecture, including tall towers and archways, forms a significant backdrop.

4.95 out of 5 average rating, 116 reviews

San Gimignano house old town

The apartment, located in the heart of the historical center of San Gimignano, overlooking the main square of the Duomo, overlooking the three most important medieval buildings. The Collegiate Cathedral of Santa Maria Assunta, the Old Palazzo del Podestà and the Palazzo del Com The Collegiate Church built in the 12th century, The People's Palace from the picturesque courtyard that preserves works of considerable importance. We also see the main tower. During the winter the cost of heating is extra

WalkabilityOutdoor spacesLayout

4.96 out of 5 average rating, 255 reviews

Casa Irene

Casa Irene is a delightful Tuscan-style apartment, located on the second and top floor of a building just a 5-minute walk from the center, 50 meters to Porta San Matteo and another 50 meters to Via Francigena. Given the secluded location, it is easily reached by car to park in the immediate free parking. The apartment equipped with WiFi and air conditioning is divided into an open space living room/kitchen, bedroom and bathroom with shower and a large terrace overlooking the walls of San Gimignano

WalkabilityOutdoor spacesLayout

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.

4.97 out of 5 average rating, 182 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.Parking available in a private garage at a cost of €9.00 per day,6 min walk.

WalkabilityOutdoor spacesCondition

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

Outdoor spacesPetsCheckout

Holiday home in Poggibonsi

An aerial view captures a charming Tuscan farmhouse nestled within lush green vineyards and rolling hills. The property features a rustic stone exterior and a terracotta roof, complemented by surrounding greenery and a clear blue sky.

Vittoria Chianti Vacations 🍇🍷

Vittoria Chianti Vacations is the ideal solution for those seeking peace and tranquility in the heart of Chianti, close to all comforts. Typical Tuscan farmhouse halfway between Florence and Siena, is located in a strategic position to quickly reach Florence, Siena, San Gimignano, Monteriggioni, Volterra and the Chianti hills. Siena Eye Laser Clinic 2 min. Private parking, two bedrooms, equipped kitchen, private bathroom, Wi-Fi, private garden, barbecue, a wonderful view of the Chianti hills.

Outdoor spacesWalkabilityComfort

4.94 out of 5 average rating, 205 reviews

4.85 out of 5 average rating, 101 reviews

A rustic kitchen features a wooden dining table with matching chairs, inviting guests to enjoy meals together. Sunlight filters through an open window with wooden shutters, illuminating the space. The kitchen is equipped with modern appliances integrated into dark cabinetry, blending functionality with traditional charm.

Home in San Gimignano

A stone's throw from the towers

Brand new gem just outside the ancient walls of SAN GIMIGNANO, one of the most beautiful villages in the world and a UNESCO World Heritage site since 1990. Beautifully renovated with high-quality materials to offer a perfect balance of comfort and functionality, making it the ideal choice for those visiting the city for leisure or business. Strategic location to explore some of the most important cities and discover cultural, scenic, and gastronomic itineraries of the wonderful Tuscany!

WalkabilityLocationValue

4.88 out of 5 average rating, 376 reviews

HOUSE OF THE MIDDLE AGES

The entire apartment and the external courtyard are for the exclusive use of the single guest. The apartment has been renovated respecting all the values of the time lived. It is located in the center, surrounded by tall towers. You will have a wonderful outdoor courtyard with views of the towers for your exclusive use for an extraordinary outdoor dinner or enjoy a glass of wine in peace. You will easily find: Restaurants, bars and ice cream parlors. We look forward to seeing you:)

WalkabilityOutdoor spacesLocation

A dining area features a round wooden table surrounded by four wooden chairs. The table is set with bright orange placemats and dishes. A small TV stands in the corner beside a fan, and kitchen cabinets are visible in the background.

4.98 out of 5 average rating, 122 reviews

La Casa di Elio

Located within the walls of San Gimignano, La Casa di Elio is the perfect solution for exploring and getting to know the City of Towers. Apartment suitable for families or couples who want to relax and enjoy the artistic and historical beauties of the medieval town. La Casa di Elio is located in the heart of San Gimignano, a stone's throw from the town's main squares, Piazza Duomo and Piazza della Cisterna, surrounded by the best bars and restaurants. Parking nearby

WalkabilityPetsHeating

A serene bedroom is showcased with a queen-size bed neatly covered with a light quilt. A bedside lamp is positioned on a simple nightstand. The room features exposed brick walls, wooden beams, and soft lighting, creating a cozy and tranquil ambiance.

4.79 out of 5 average rating, 165 reviews

Stunning 4 people apt in the center - SanGimignano

Bright apartment completely renewed with 2 bathrooms!! In the heart of the historical center of San Gimignano medieval village. 100% Quiet and safe area with many nice restaurants and shops in the immediate nearby! Fast Wifi always at your free disposal. Ideal for people traveling by transportation or by car too! A payment parking area is less then 5 minute walking. There are also other cheaper parking areas around the village. You can walk everywhere here!

WalkabilityTVCleanliness

Superhost

Home in Barberino Tavarnelle

Nada Home

3 comfortable, fully air-conditioned double bedrooms, each with its own private bathroom, in the heart of Chianti, ideally located between Florence, Siena and San Gimignano. A welcoming, well-kept home in the peaceful Tuscan countryside. Fully equipped kitchen with dishwasher, oven and bar area, plus a laundry room with washing machine and dryer. Private garden for your exclusive use with a private hydromassage pool, heated in winter upon request 🌷

PetsWalkabilityShared spaces

4.87 out of 5 average rating, 215 reviews

Holiday home in San Gimignano

La Casa dei Ricordi - car/motorcycle garage at 650m

Welcome to La Casa dei Ricordi, a 17th-century home full of soul: this is where I was born and raised. Today, it opens its doors to offer you an authentic experience. Located in an incredibly quiet and peaceful area, it’s the perfect place to relax just steps away from Piazza del Duomo and Piazza della Cisterna. A charming retreat in the heart of the historic center, where history meets the peace of a true family home.

PetsWalkabilityKitchen

4.96 out of 5 average rating, 139 reviews

Popular amenities for San Gimignano pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.88 out of 5 average rating, 144 reviews

Home in San Gimignano

Giovanna apartment 100m from San Gimignano

Outdoor spacesWalkabilityBiking

4.95 out of 5 average rating, 250 reviews

Home in San Gimignano

My country house: garden, quiet, sun, towers view!

WalkabilityOutdoor spacesIndoor spaces

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

Outdoor spacesPetsAmenities

4.96 out of 5 average rating, 330 reviews

Home in Barberino Tavarnelle

SuiteLouise.pool, Hot Tub,homeGym & private Garden

Outdoor spacesWalkabilityGetting around

4.91 out of 5 average rating, 124 reviews

4.91 out of 5 average rating, 126 reviews

An aerial view captures a rustic countryside villa nestled within lush greenery and olive groves. The structure features a tiled roof and surrounded by trees, with a separate building visible nearby. The serene landscape enhances the sense of privacy and tranquility.

Home in Montespertoli

Costalmandorlo, a rustic home in the heart of Tuscany

WalkabilityOutdoor spacesParking

4.95 out of 5 average rating, 200 reviews

A cozy bedroom is highlighted with a floral wallpaper featuring vibrant colors. A bedside table made of wood stands beside a spacious bed dressed in pink bedding. A modern lamp provides warm lighting, enhancing the inviting details of the room.

Home in Pievescola

Borgo Ripostena – No. 8 Casa Vecchia

Outdoor spacesPetsLocation

4.93 out of 5 average rating, 201 reviews

The rustic stone house features a facade adorned with climbing greenery, offering a blend of natural beauty and architectural charm. Large wooden doors open onto a welcoming terrace, which is surrounded by greenery, providing a serene outdoor space for relaxation.

Home in Volterra

Collina Power

Outdoor spacesWalkabilityView

4.9 out of 5 average rating, 290 reviews

A spacious living area features exposed stone walls and a rustic fireplace with a television positioned nearby. A light-colored sideboard complements the warm tones of the wooden beams above. A dining table with red chairs is set beside large glass doors that open to a green outdoor space.

Home in Poggibonsi

Tuscan Counrtry Detached House. Wi-Fi Free

WalkabilityOutdoor spacesLocation

Pet-friendly home rentals with a pool

4.92 out of 5 average rating, 386 reviews

An aerial view reveals the rustic stone farmhouse surrounded by lush greenery and vineyards. The inviting pool is set within a well-maintained garden, complemented by outdoor seating and barbecue areas, offering a peaceful retreat in the heart of the Tuscan countryside.

Apartment in Gavignano

Poggio Massiccioli

WalkabilityPetsLong stay

4.98 out of 5 average rating, 126 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

Outdoor spacesWalkabilityQuiet

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

Outdoor spacesWalkabilityHospitality

4.93 out of 5 average rating, 254 reviews

4.95 out of 5 average rating, 219 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

Farmhouse in Chianti

Outdoor spacesWalkabilityLong stay

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.

Belforti Tower

PetsWalkabilityAmenities

4.99 out of 5 average rating, 137 reviews

Holiday home in Barberino Val d'Elsa

An aerial view of a charming countryside property surrounded by olive trees and greenery. The image showcases a rustic stone building with a tiled roof, complemented by a private pool in the foreground. Well-maintained pathways weave through the landscape, enhancing the tranquil setting.

Linearis apt B (4+2) Toscana

WalkabilityOutdoor spacesSleep quality

4.89 out of 5 average rating, 155 reviews

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.

WalkabilityOutdoor spacesNearby

4.89 out of 5 average rating, 307 reviews

Villa in Siena

Villa Capanna, Private Pool, Breathtaking Views

Outdoor spacesWalkabilityTV

Private, pet-friendly home rentals

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

PetsOutdoor spacesBackyard

A cozy living area features a wooden dining table surrounded by colorful chairs. A soft, yellow sofa adds warmth to the space. Natural light enters through the windows, highlighting artwork on the walls and creating a welcoming ambiance. The entrance door is made of wood.

4.9 out of 5 average rating, 178 reviews

Il Nespolo - "Girasole" apartment with kitchen

WalkabilityPetsComfort

4.99 out of 5 average rating, 470 reviews

A rolling landscape showcases neat rows of lush green vineyards under a softly lit sky. A charming village, featuring a prominent clock tower, is nestled among the trees and hills in the background. The tranquil atmosphere highlights the area's natural beauty.

Apartment in San Gusmè

Beautiful medieval village!!!

WalkabilityPetsCheckout

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

PetsWalkabilityCondition

4.88 out of 5 average rating, 126 reviews

4.89 out of 5 average rating, 89 reviews

A spacious private terrace is furnished with outdoor seating arrangements and surrounded by greenery. Pots with plants and flowers accentuate the area. Soft sunlight filters through the trees, creating a serene environment perfect for relaxation.

Condo in San Gimignano

Relax in San Gimigano: Terrace + free Parking.

WalkabilityOutdoor spacesAccuracy

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.

5.0 out of 5 average rating, 43 reviews

The Penthouse of Dreams

WalkabilityAccuracySleep quality

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.

Casa Renai - holidays with friends in San Gimignano

Outdoor spacesPetsHospitality

5.0 out of 5 average rating, 48 reviews

A dining area features a wooden table set with dishes and drinks. The adjacent kitchen includes a counter with seating, while a cozy living space is visible in the background, equipped with a television and plant. Natural light enhances the space.