Family-friendly holiday rentals in Certaldo

4.98 out of 5 average rating, 221 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

Welcome to the delightful cottage of Riccardo and Pauline, a small corner of love where colors and details are designed to give peace and quiet. You will find yourself immersed in the green Tuscan hills, in a breathtaking landscape where the renowned Chianti Classico wine is born. The area is ideal for walking and cycling. You will be close to the cities of art, such as Florence, Siena and Arezzo. Upon request and according to availability, we offer a paid shuttle service. We look forward to seeing you ❤️

FamilyIndoor spacesCleanliness

4.94 out of 5 average rating, 160 reviews

A wooden dining table is positioned on a shaded patio, featuring a decorative pine cone sculpture at its center. Surrounding greenery includes blooming flowers, with distant hills visible in the background, creating a peaceful outdoor setting ideal for al fresco dining.

Condo in Scandicci

Florentine Hills 'Le Scalette'

The property is a portion of a 16th Century Casa Colonica (a typical Tuscan farmhouse) situated atop a hill surrounded by vineyards, olive groves and sprawling views of the surrounding hills. The village of San Vincenzo a Torri and of Ginestra Fiorentina are respectively 2km away grocery and bakery stores, pharmacy, bank, restaurant, news stands, and petrol stations are within minutes from the house. Only 16km (10miles) to Florence the toll free highway is 3km from the house. Car is a must.

KitchenIndoor spacesLong stay

Home in San Casciano In Val di Pesa

A stone structure with a tiled roof is framed by greenery, surrounded by rolling hills. A spacious outdoor area features a wooden table, inviting relaxation. Large trees and thriving shrubs enhance the tranquil setting, with a backdrop of a serene sunset illuminating the landscape.

4.98 out of 5 average rating, 235 reviews

The Chianti Classico Sunset

If you are looking for an idyllic location in the heart of the Chianti Classico region, surrounded by the vineyards and olive groves of the beautiful Tuscan hills, on the estate of a historic 16th-century villa, then come to our barn!! It has a dominant position with an amazing view, where you can enjoy breathtaking sunsets. The complete independence of the house, the welcoming garden and the large loggia allow you to enjoy your stay in total tranquillity. Our reviews are your best guarantee.

KitchenFamilyLayout

5 out of 5 average rating, 336 reviews

An aerial view captures Podere Vergianoni nestled in the Chianti hills, surrounded by lush vineyards. The property features a clear blue pool, shaded terraces, and carefully landscaped gardens. Rolling hills and rows of grapevines create a serene backdrop, highlighting the natural beauty of the Tuscan countryside.

Condo in Noce

Podere Vergianoni nestled in Chianti with a pool

Podere Vergianoni è un antica e storica proprietà risalente al 1600 situato nelle splendide colline del Chianti in Toscana con la possibilità di organizzare servizio navetta e esperienze esclusive su misura per voi . L'appartamento è disponibile per 2 adulti con possibilità aggiunta divano letto per 2 bambini sotto i 12 anni . Nel grande cortile esterno troverete una piscina a sale con area relax su terrazza panoramica con vista su castello colline e vigneti con tramonti unici.

FamilyKitchenHeating

4.99 out of 5 average rating, 121 reviews

Condo in Gambassi Terme

Cosy Tuscan Home near Florence & San Gimignano

UN NIDO ACCOGLIENTE dove tradizione e confort moderno s'incontrano. Perfetto per chi desidera rallentare, rilassarsi e vivere la Toscana più autentica, lontano dal caos. Immagina di svegliarti nel cuore di un borgo toscano, affacciarti sulla piazza e iniziare la giornata con la tranquillità e I ritmi locali. L'appartamento completamente ristrutturato e arredato con gusto, si trova nel centro storico di Gambassi Terme, un punto strategico per eslorare le meraviglie della Toscana.

KitchenIndoor spacesDecor

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.

4.98 out of 5 average rating, 208 reviews

Stone House with Exclusive Pool Codilungo in Chianti

Welcome to your Tuscan dream between Florence & Siena. Perfect for families or romantic getaways. • 360° views of iconic Chianti hills. •Huge Exclusive Infinity Pool (17x9m), lit at night (open from May 1st to October 15th) • Total privacy, yet restaurants/shops are 10-15 mins away. • Comfort for 6: 3 bedrooms (2 double, 1 twin) & 3 full baths. • Modern amenities: Fully equipped kitchen area, Smart TV. • Outdoor bliss: Large dining loggia, professional BBQ, poolside porch & bath.

FamilyIndoor spacesOutdoor spaces

5 out of 5 average rating, 218 reviews

An aerial view of the property reveals a charming red house surrounded by lush greenery. Tall cypress trees and vibrant bushes create a tranquil landscape, while an expansive lawn features relaxing loungers, inviting guests to enjoy the serene atmosphere of the Tuscan countryside.

Home in Gambassi Terme

Il Fienile, Luxury Apartment in the Tuscan Hills

‘Il Fienile’ is in an enchanting position immersed in the beauty of the Tuscan hills, with a breathtaking view of the surrounding countryside. It is located in the hamlet of Catignano in Gambassi Terme, just a few kilometres from San Gimignano. The house sits in a protected oasis surrounded by a beautiful private park with olive trees, a pond, pine trees and woods, where you can walk, relax and enjoy the pleasures of unspoilt nature. A unique experience entirely to be enjoyed.

Indoor spacesFamilyView

An outdoor lounge area is presented, featuring comfortable sun loungers and a low coffee table. A spacious arched doorway leads to the interior. Warm yellow walls are complemented by artistic wall decor, and the surrounding landscape includes greenery and hills.

4.93 out of 5 average rating, 115 reviews

SuiteLouise.pool, Hot Tub,homeGym & private Garden

SuiteLouise, in the chianti region is the perfect retreat for those seeking design,comfort and authentic tuscan vibes.Relax in the outdoor lounge,enjoy a bbq in the rose garden, or unwind in the private hot tub or home gym. Feel at home embraced by the rolling tuscan hills, whille i help you create tailor-made stays with 10+experiences. Contact me to craft your tuscan escape and create unforgettable memories in this strategic and amazing area between Florence and Siena.

FamilyKitchenSleep quality

4.92 out of 5 average rating, 217 reviews

Farm stay in Sovicille

House at Gianni - Leccio

Ciao, siamo Cristina e Carmelo! Vi aspettiamo a "Casa al Gianni", il nostro agriturismo tra i boschi della Montagnola Senese a soli 20 minuti da Siena. Qui la vita rallenta: Solo il profumo della terra, il canto degli uccelli e la simpatia dei nostri animali. È un invito a riscoprire la bellezza delle piccole cose, immersi nel verde della Toscana più vera. Non è solo una vacanza, è un ritorno alle origini. Questo angolo di pace vi resterà nell'anima. Vi aspettiamo!

KitchenFamilyValue

4.84 out of 5 average rating, 103 reviews

A clear view of a swimming pool is presented, surrounded by a well-maintained grassy area. Sun loungers are positioned near the pool, with umbrellas providing shade. In the background, a building is visible, set among trees and shrubs, enhancing the serene landscape.

Condo in Certaldo

Tenuta di Pomine Certaldo (Fi) Edera Apartment

Located on the 1st floor, 65 m2, spacious, bright, Tuscan-style furnishings consisting of a living room/kitchen, a double bedroom, a bedroom with two beds. Kitchenette (4-burner stove), oven, refrigerator, freezer, dishwasher. Bathroom with shower/sink/bidet/toilet, swimming pool (6x12 m.), shared washing machine on the ground floor, Wi-Fi. Terrace equipped with garden furniture, grill. Linen change once a week. There are two other apartments in the house

Indoor spacesKitchenDecor

4.78 out of 5 average rating, 126 reviews

A spacious living area is depicted, featuring a dining table set with plates and cups. A comfortable sofa is positioned beside the table, and a staircase leads to the upper level. Natural light enters through the open terrace doors, providing a view of the outdoor area.

Condo in Certaldo

In the center of Certaldo

The apartment is located in the heart of Certaldo, a small and quiet town nestled among the unmistakable Tuscan hills, just a 5-minute walk away you will find the train station from where you can reach Siena or Florence, and also other cities, or by car. Certaldo has a unique medieval charm: the historic center in the upper part is in fact beautifully preserved and from our apartment you can reach it on foot in a few minutes or with a panoramic funicular.

KitchenIndoor spacesAccuracy

4.98 out of 5 average rating, 129 reviews

An aerial view captures the medieval village of Certaldo, featuring terracotta rooftops and winding streets. The lush greenery surrounding the village adds a natural touch, while historic buildings stand prominently, showcasing varied architectural styles. The placement of the highlighted property is evident within the quaint atmosphere.

Apartment in Certaldo

House in a medieval tower with a view in Certaldo

Vacation home located in the heart of the medieval village of Certaldo. Second floor apartment without elevator consisting of kitchen with dining room, bedroom with plasma TV and terrace, bathroom with shower, bedroom with sofa bed, relaxation area and panoramic view. Large garden with barbecue! Sleeps 4. Free Wi-Fi!!!

KitchenIndoor spacesBackyard

Popular amenities for Certaldo 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, 211 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.

FamilyKitchenShared spaces

4.85 out of 5 average rating, 141 reviews

A charming house is framed by lush greenery, with several trees dotting the manicured lawn. The exterior features warm tones, complemented by a covered porch area. Various plants provide a natural ambiance, enhancing the serene outdoor space.

Home in Montespertoli

I Limoni Apartment in Tuscany

KitchenIndoor spacesHot tub

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, 121 reviews

Torretta Apartment

FamilyKitchenBiking

Villa in San Casciano In Val di Pesa

A heated jacuzzi is situated under a shaded pergola, surrounded by lush greenery and colorful flowers. The serene outdoor space is complemented by a gravel path leading towards vineyards in the background, inviting relaxation and privacy.

4.94 out of 5 average rating, 197 reviews

Il Vichiaccio: Accessible Chianti Villa & Jacuzzi

FamilyIndoor spacesQuiet

4.99 out of 5 average rating, 151 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

KitchenIndoor spacesWi-Fi

Superhost

A cozy living area features a fireplace with stacked logs, complemented by a comfortable armchair and decorative wall art. A spacious bed is visible in the background, framed by wooden beams that enhance the room's rustic charm.

4.86 out of 5 average rating, 205 reviews

Nada Home

KitchenFamilyOutdoor spaces

4.97 out of 5 average rating, 108 reviews

Dome in Volterra

Green Dome @ The Land Before Time Retreats

Indoor spacesFamilyHot tub

4.93 out of 5 average rating, 187 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 spacesKitchenAmenities

Family- and pet-friendly home rentals

4.89 out of 5 average rating, 329 reviews

A spacious living area features large arched windows offering panoramic views of the Tuscan hills. A black leather sofa and a rocking chair are arranged around a decorative coffee table, with a subtle light from a chandelier above. A fireplace adds warmth to the serene space.

Townhouse in Scandicci

Florence Country Side: Giogoli a place to be!

FamilyIndoor spacesLong stay

4.96 out of 5 average rating, 112 reviews

An aerial view of a private pool surrounded by a well-maintained garden. Sun loungers are arranged next to the pool, which is bordered by a stone pathway. Lush greenery and trees provide a serene backdrop to the inviting outdoor space.

Guest suite in Empoli

Private pool & panoramic garden on the countryside

Indoor spacesFamilyValue

4.99 out of 5 average rating, 457 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!!!

FamilyIndoor spacesNearby

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, 326 reviews

Casa Al Poggio in Chianti Shire

FamilyKitchenComfort

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

Indoor spacesFamilyCheckout

4.95 out of 5 average rating, 196 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

Indoor spacesKitchenHospitality

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.

4.95 out of 5 average rating, 113 reviews

Casa Luigi Suite with exclusive pool

KitchenFamilyCleanliness

4.86 out of 5 average rating, 107 reviews

A rustic stone building is framed by a large, leafy tree in the foreground. A wooden chair is positioned beside the tree. The scene captures a view of rolling hills in the background, evoking a peaceful countryside setting.

Home in Gambassi Terme

House in the heart of Tuscany

Indoor spacesFamilyWalkability

Family-friendly home rentals with a pool

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.

4.9 out of 5 average rating, 173 reviews

App.with pool and beautiful view, 5 adults

Indoor spacesFamilyPool

4.99 out of 5 average rating, 330 reviews

Farm stay in Pisa

Tenuta Chiudendone in Tuscany

Indoor spacesKitchenCheck-in

Home in Castellina in Chianti

A lush green garden is framed by a rustic pergola made of wooden beams. Grassy paths lead deeper into the garden, where vibrant flowers and trees provide a natural backdrop. Rolling hills and a clear blue sky are visible in the distance, creating a serene outdoor setting.

4.98 out of 5 average rating, 131 reviews

Private Chianti Cottage, Garden & Vineyard Views

Indoor spacesKitchenLayout

Home in Barberino Tavarnelle

The image showcases a refreshing pool surrounded by lounge chairs and umbrellas, enhancing the outdoor relaxation area. The pool is framed by lush greenery and a stone wall, with the charming rustic house visible in the background under a clear blue sky.

5 out of 5 average rating, 127 reviews

Infinity pool in Chianti area

Indoor spacesFamilyTV

4.96 out of 5 average rating, 135 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

KitchenFamilyWi-Fi

Farm stay in Badia a Passignano

A refreshing swimming pool is surrounded by a stone wall adorned with blooming flowers. Olive trees are visible in the background, leading up to a rustic building with a red door. Sunlight reflects off the clear water, creating a serene atmosphere.

4.8 out of 5 average rating, 248 reviews

A barn in Chianti

Indoor spacesFamilyDecor

Farm stay in Lastra a Signa

A modern swimming pool is surrounded by a spacious wooden deck, lined with lounge chairs, offering expansive views of the rolling hills and olive groves. A large tree provides shade next to the pool, creating a serene outdoor space for relaxation.

4.98 out of 5 average rating, 105 reviews

Authentic Farmhouse Apartment

FamilyKitchenHospitality