Family-friendly holiday rentals in San Gimignano

Holiday home in loc. Simignano

A charming rustic farmhouse is set against a dramatic sky, framed by lush green trees. The exterior features warm-toned walls and a tiled roof, while a spacious yard includes seating arrangements for outdoor relaxation, inviting guests to enjoy the serene countryside.

Casa al Gianni - Oak

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!

FamilyKitchenCondition

4.93 out of 5 average rating, 244 reviews

5.0 out of 5 average rating, 218 reviews

An aerial view captures the sprawling vineyards and olive groves surrounding Podere Vergianoni. The property features a salt-water pool positioned on a terrace, offering panoramic views of the lush Chianti landscape and medieval castle in the distance. Rustic buildings line the garden area.

Condo in Noce

Ancient Podere of the 1600s in Chianti in Tuscany

Podere Vergianoni is an ancient and historic property dating back to the 1600s, located in the beautiful Chianti hills in Tuscany, with the possibility of organising exclusive services and experiences tailored to you. The apartment is available for 2 adults with the possibility of adding a sofa bed for 2 children under 12 years of age. In the large outdoor courtyard, you will find a saltwater swimming pool with a relaxation area on a panoramic terrace with a wonderful view of the castle, hills and vineyards, with breathtaking sunsets.

Indoor spacesKitchenAccuracy

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.

Indoor spacesFamilyWalkability

Farm stay in San Gimignano

A scenic view captures a hillside vineyard with neatly arranged rows of grapevines. Olive trees dot the landscape, leading to a rustic farmhouse in the foreground, while the skyline of San Gimignano rises against a clear blue sky in the background.

Montegonfoli 5 apartment in farmhouse, 4+2 guests

Comfortable apartment for 4 adults and 2 babies under 12yo, in San Gimignano countryside, in a resort/farmhouse. Here in Montegonfoli you can spend a vacation in absolute relax, in an enchanted natural context, far from the noise but at the same time very close to the most beautiful attractions of the world. First floor with amazing views on San Gimignano and Chianti Hills. No aircon, but every bedroom has a large fan for the few hot nights we are getting in July/August. We usually have 15°C!

KitchenIndoor spacesAir conditioning

4.84 out of 5 average rating, 264 reviews

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:)

Indoor spacesFamilyLaundry

Holiday home in San Gimignano

A bright bedroom features a spacious bed with crisp white linens and a decorative pillow. A vivid landscape painting hangs above, while a window with wooden frames reveals a scenic view of the Tuscan hills, complemented by soft natural light filtering through sheer curtains.

Breathe in Tuscany: 180° view of the hills

Please note that the second bedroom is divided from the hallway by a curtain and not by a door. Experience San Gimignano with a splendid view of the Tuscan hills! In the heart of San Gimignano, experience the city with a separate entrance, second floor and breathtaking views of the Tuscan hills. Private parking is available upon request. Entrance, living room, 2 double bedrooms, kitchen and large bathroom. city tax to be added to the price, €2.50 per person per night.

Indoor spacesKitchenAir conditioning

4.98 out of 5 average rating, 163 reviews

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

FamilyKitchenLaundry

4.97 out of 5 average rating, 132 reviews

The image showcases the exterior of an ancient stone building within the historical walls of San Gimignano. Sunlight illuminates the textured facade, highlighting the charming architectural details, including windows and balconies. A quiet pathway leads to the entrance, surrounded by greenery.

Home in San Gimignano

Casa Maurino

"Casa Maurino", in the historic center of San Gimignano, is a delightful apartment nestled in the ancient city walls. Ideal place to spend short stays, immersing yourself in the evocative atmosphere of the medieval village. Located in a quiet and peaceful position with a panoramic terrace overlooking the Tuscan hills to indulge in romantic moments of relaxation. Independent entrance from a characteristic stone staircase, panoramic terrace. Suitable for couples.

FamilyKitchenGetting around

A bright living area features a light wooden dining table surrounded by four white chairs. A dark blue sofa is positioned against the wall, and two windows allow natural light to enhance the space. The view outside includes hints of greenery.

4.99 out of 5 average rating, 188 reviews

The Tuscan Dream-modern in the center of San Gimignano

The Tuscan Dream, an exclusive apartment in the historic center of San Gimignano! This 100 m² apartment, located a few steps from the famous medieval towers, is the ideal base for exploring the UNESCO heritage village. The apartment has large bright spaces, a fully equipped kitchen, a living room with panoramic views of the Tuscan hills, two elegant bedrooms and two spacious bathrooms. Enjoy a spectacular view and relax at sunset with a good glass of local wine.

FamilyIndoor spacesAccess

Villa in Barberino Tavarnelle

A large swimming pool surrounded by a brick patio and manicured lawns is highlighted in this image. Sun loungers are positioned along the pool's edge, with lush greenery and trees creating a serene backdrop. The villa's charming structure is visible in the distance under a partly cloudy sky.

Podere Tignano, 4-bedroom villa in the Chianti!

Nestled among the rolling hills of Chianti between Florence and Siena, Podere Tignano offers breathtaking views over vineyards, olive groves, and golden grain fields. This charming Tuscan stone villa blends authentic rural character with modern comfort and welcomes up to 8 guests in 4 bedrooms. Surrounded by peaceful countryside and featuring a private swimming pool, it is the perfect retreat for those seeking relaxation, nature, and the true spirit of Tuscany.

FamilyKitchenGetting around

4.98 out of 5 average rating, 105 reviews

A tranquil landscape is captured at sunrise, with the sun rising above a misty valley. Soft golden light filters through layered clouds, illuminating the distant hills. The scene conveys a sense of peace and natural beauty, set against a backdrop of serene fog.

4.93 out of 5 average rating, 131 reviews

Apartment with panoramic garden in San Gimignano

Located close to the walls of San Gimignano, the apartment is surrounded by nature with every desirable comfort and an amazing panoramic view. The apartment consists of 1 kitchen, 1 double bedroom, 1 living-dining room, panoramic garden and reserved parking next to the house. - 2 minutes' walk from the city center, surrounded by nature - panoramic view - every desirable comfort -private parking - 1 kitchen, 1 bedroom, 1 bathroom, 2 living rooms

KitchenIndoor spacesAir conditioning

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.

Indoor spacesKitchenValue

4.96 out of 5 average rating, 139 reviews

Popular amenities for San Gimignano family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.95 out of 5 average rating, 169 reviews

Dome in Volterra

Green Dome @ The Land Before Time Retreats

Indoor spacesFamilyAir conditioning

4.93 out of 5 average rating, 194 reviews

A spacious living area features a large wooden table set for a meal, adorned with fresh fruits and glassware. A comfortable red couch is positioned nearby, complemented by framed black and white photographs on the wall and stylish pendant lights above.

Condo in Casole d'Elsa

La Casetta

Indoor spacesKitchenLayout

Superhost

Home in Barberino Tavarnelle

Nada Home

KitchenFamilyCleanliness

4.87 out of 5 average rating, 215 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.

Indoor spacesKitchenValue

Farm stay in Greve in Chianti

A spacious outdoor area features a swimming pool surrounded by lush green lawns and dotted with comfortable sun loungers. Umbrellas provide shade, and the serene landscape is framed by tall trees and gentle hills in the background.

Typical Tuscan country house

Indoor spacesKitchenLocation

4.99 out of 5 average rating, 431 reviews

4.99 out of 5 average rating, 148 reviews

A tranquil pool area is highlighted by a clear blue pool flanked by sun loungers under white umbrellas. Lush greenery surrounds the property, with a charming farmhouse visible in the background, and inviting pathways guide guests through the scenic landscape.

Villa in Capannori

Farmhouse , pool, 13 px. Lucca 10km

KitchenFamilyOutdoor spaces

Home in Barberino Tavarnelle

SuiteLouise.pool, Hot Tub,homeGym & private Garden

Indoor spacesFamilyBarbecue

4.91 out of 5 average rating, 124 reviews

Villa in Barberino Tavarnelle

A charming stone villa is set amidst a lush green lawn. The building features wooden window shutters and a terracotta tile roof. A covered porch, adorned with flower pots, offers a welcoming outdoor space, complemented by a backdrop of blooming plants and trees.

CasaDiManuela:TotallyPrivateChiantiVilla withTub

Indoor spacesKitchenValue

4.97 out of 5 average rating, 105 reviews

Family- and pet-friendly home rentals

4.84 out of 5 average rating, 262 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

Indoor spacesFamilyComfort

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 Casa Centro Storico

FamilyIndoor spacesAir conditioning

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

Indoor spacesKitchenWi-Fi

4.96 out of 5 average rating, 255 reviews

Casa Irene

FamilyKitchenGetting around

4.94 out of 5 average rating, 200 reviews

The kitchen and dining area is presented with green cabinetry and a white table set for six. A modern black refrigerator complements the space. Light fixtures hang above, and the wooden ceiling beams add warmth. A portion of the wall features decorative artwork.

Home in San Gimignano

Casa Aurora 100m from San Gimignano

FamilyKitchenEV charging

4.88 out of 5 average rating, 338 reviews

Townhouse in Scandicci

Florence Sunset Hills • Giogoli

Indoor spacesFamilyAir conditioning

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

FamilyKitchenLong stay

Holiday home in Poggibonsi

Sangi Chianti Vacations

KitchenFamilyBackyard

4.91 out of 5 average rating, 112 reviews

Family-friendly home rentals with a pool

4.96 out of 5 average rating, 144 reviews

A winding driveway is lined with tall cypress trees on either side. The green landscape stretches into the distance, revealing rolling hills and a distant rustic building surrounded by nature, creating a serene and inviting setting.

Home in Montaione

Cercis - La Palmierina

KitchenFamilySleep quality

Home in Barberino Val d'Elsa

Villetta La Colombaia Farm

FamilyKitchenAir conditioning

4.96 out of 5 average rating, 161 reviews

Cottage in Barberino Tavarnelle

The stone house features a welcoming entrance with large arched windows. A vibrant flower box filled with geraniums complements the lush green lawn. A shaded area with wooden seating offers a place to relax, while the infinity pool and surrounding vineyards are visible in the background.

Stone House with Exclusive Pool Codilungo in Chianti

KitchenIndoor spacesDecor

4.98 out of 5 average rating, 216 reviews

4.96 out of 5 average rating, 207 reviews

A well-maintained garden surrounds a refreshing pool, bordered by manicured grass. A comfortable seating area, featuring two lounger chairs and a shaded umbrella, provides a serene spot for relaxation. Soft greenery and flowering shrubs form a natural backdrop, enhancing the tranquil atmosphere.

Villa in Tignano

Villa Isabella

Indoor spacesKitchenQuiet

Farm stay in Castelfiorentino

A vibrant flower garden enhances the view of a rectangular swimming pool surrounded by green grass. Sun loungers and shaded seating areas are available nearby, inviting relaxation. Rolling hills and a cloudy sky form a serene backdrop, adding to the tranquil atmosphere of the outdoor space.

App.with pool and beautiful view, 5 adults

KitchenIndoor spacesWalkability

4.9 out of 5 average rating, 181 reviews

4.99 out of 5 average rating, 113 reviews

Home in Greve in Chianti

Relaxation and charm in the Chianti hills

Indoor spacesKitchenLong stay

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

FamilyIndoor spacesShared spaces

4.89 out of 5 average rating, 155 reviews