Family-friendly holiday rentals in Castiglioncello

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.

5 out of 5 average rating, 284 reviews

Podere Vergianoni nestled in Chianti with a pool

Podere Vergianoni is an ancient and authentic farmhouse dating back to the 17th century located in the beautiful hills of Chianti in Tuscany. The apartment is impeccably furnished in the traditional local style of old Tuscany: ancient wooden beams, terracotta floors, and unique furniture. In the large outdoor courtyard, you'll find a large swimming pool on a panoramic terrace at your disposal, overlooking the valley with breathtaking views of vineyards and olive groves, where you can enjoy spectacular sunsets.

A rustic dining area features a long wooden table set with linens and decorative items. The space is illuminated by a chandelier and has large windows offering views of the surrounding landscape, with a stone fireplace and traditional frescoes adorning the walls.

4.96 out of 5 average rating, 225 reviews

Giglio Blu Charming Loft

The accommodation is a portion of a historical noble residence dating back to the 14th century, adorned with frescoes and tastefully restored. It is located on the ground floor of a quiet and safe street, with a private and independent entrance and self check-in. The space is cozy, comfortable, and elegant, perfect for guests seeking an authentic Tuscan experience with modern comfort and technology. It is situated just a few kilometers away from Florence, Pisa, Lucca, Vinci, San Gimignano...

A spacious terrace is surrounded by lush greenery, featuring terracotta pots filled with plants. Comfortable wooden chairs are positioned to invite relaxation, overlooking scenic hills in the distance. A soft canopy provides shade, enhancing the tranquil atmosphere of this outdoor space.

4.99 out of 5 average rating, 133 reviews

House with a breathless view in Tuscany

Halfway between Pisa and Florence this house comes with a large panoramic terrace, equipped with sunchairs and a large table for outdoor dining. Below, an hanging garden on the property overlooks one of the most striking views in Tuscany. The location is strategic, in the beating heart of an ancient medieval village, now home to an open-air contemporary art museum. Peccioli is a great starting point for those who want to visit the art cities of Tuscany, or immerse yourself in local life,

A charming entrance is highlighted by a white door and green shutters flanking a window adorned with blooming flowers in pots. A blue bicycle rests next to a small table and chairs, creating a welcoming outdoor space with vibrant plants.

4.99 out of 5 average rating, 154 reviews

La casa dei remi, discover Tuscany near the sea

My house is located in Livorno, in the characteristic Antignano district, close to the center and a stone's throw from the beautiful coves of the Lungomare, perfect for a dip and sunbathing. Ideal base for discovering the treasures of our city and the famous Tuscan art cities. You can enjoy our sea and cuisine based on fresh fish. Coffee, tea, herbal teas, milk and cookies are offered. The quiet and picturesque neighborhood is a 10-minute drive or 20-minute bike ride from the Center.

A spacious bedroom features a large bed with green accents, complemented by softly glowing bedside lamps. Light enters through a sizable window with sheer curtains, illuminating the room's bright walls. Artistic frames are displayed along the walls, enhancing the room's inviting atmosphere.

4.93 out of 5 average rating, 568 reviews

REFURBISHED apartment, 75 sqm 10 min from the sea.

Ideal for a family vacation, the apartment is located about 10 km (10 minutes) from the sea and is located on the second floor of a small building where we also live, measures about 75 square meters and is completely renovated. Consisting of a small entrance, 2 large bedrooms, a kitchen, a bathroom and a closet, it is very comfortable, bright and spacious. Bus stop about 20 meters away, pharmacy, supermarket and other services ALL within walking distance, restaurants in the area

A serene garden area features two lounge chairs positioned on lush green grass, overlooking the sea in the distance. White lilies bloom in the foreground, complemented by a rustic shade structure nearby, providing a tranquil setting for relaxation.

4.95 out of 5 average rating, 146 reviews

Casa del Poggio, with a beautiful sea view

The Casa del Poggio (house at the hill) is located in the hills of Castagneto Carducci and is part of our organic farm. It is immersed in a peaceful countryside surrounded by olive groves, vineyards and woodland and enjoys a beautiful view of the sea and the castle of Castagneto Carducci. At the same time its position allows you to reach the village in just 10 minutes by foot and the beaches of Marina di Castagneto in 10 minutes by car or bus.

Superhost

A bright interior features large double windows, allowing natural light to fill the space. The view displays the sea and a nearby promenade, with soft, flowing curtains framing the scenic outlook. A simple white bed is positioned close to the windows.

Loft

4.8 out of 5 average rating, 493 reviews

the sunset loft

Ideal for enjoying the magnificent climate of our city and its endless waterfront of the nineteenth century, SUNSET LOFT is a romantic studio apartment overlooking the iconic "TERRAZZA MASCAGNI" with a unique view of the Mediterranean sunset. Private parking, wireless internet, smart TV, full kitchen with dishwasher, ceiling / floor, wooden floors and large bathroom with ceiling light complete the picture for a romantic and relaxing stay.

A rustic stone house blends with the natural surroundings, situated on a hillside. The pathway, composed of natural stones, leads to the entrance. Lush greenery envelops the home, and a shaded area with wooden seating is visible nearby.

4.97 out of 5 average rating, 176 reviews

The Fox's Lair

The house is a rustic stone and wood house in the Apuan Alps park, an ideal place for those who want to take walks in the woods and get to know and visit the attractions of Versilia and Tuscany between the sea and mountains. The house consists of a full kitchen and has a wood stove or heat pumps for heating, a double sofa bed, and on the second floor the full bedroom and full bathroom, and outside a terrace, then a loft with a single bed.

A welcoming living area features a light-colored sofa set arranged around a small coffee table. Natural light enters through a doorway, illuminating the space. A potted plant adds a touch of greenery, and a staircase leads to the upper floor.

4.98 out of 5 average rating, 130 reviews

Casa Gianguia apartment 100 meters from the sea

Villa type "viareggina", with the name "Gianguia", located in an excellent position with respect to the center of Castiglioncello and Rosignano, a short walk to the sea, and the main services. Recently renovated, with practical and modern furniture but tasteful; equipped with all the comforts to guarantee guests a pleasant and relaxing stay. Ideal for couples and families who love the sea and relaxation.

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.

4.91 out of 5 average rating, 232 reviews

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!

4.9 out of 5 average rating, 213 reviews

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.

Holiday home

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.

4.99 out of 5 average rating, 309 reviews

Tenuta Chiudendone in Tuscany

Great place in the middle of Tuscan Hills, you will be sorrounded by nature but close to all the beautiful cities of Tuscany! We rent two apartments, one on the upper floor called Balla and one on the ground floor called Modigliani. Tell us which one you prefer. PLEASE NOTE YOU WILL NEED A CAR DURING YOUR STAY.

Popular amenities for Castiglioncello family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

An infinity pool reflects the sky, surrounded by olive trees. A figure enjoys a swim, with panoramic views of the Tuscan hills in the distance. Soft clouds drift overhead, enhancing the serene landscape.

5 out of 5 average rating, 122 reviews

Infinity pool in Chianti area

4.98 out of 5 average rating, 176 reviews

The bedroom features a luxurious bed adorned with soft linens and decorative pillows. A unique round door, resembling a submarine hatch, creates a striking focal point. Art pieces depicting nautical themes enhance the space, set against elegantly finished wooden walls.

Casa particular

[Near Florence] Nautilus loft

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

Beautiful renovated barn in Tuscany

A tranquil scene of a swimming pool reflects the blue sky and surrounding greenery. Lush trees and rustic buildings are visible in the background, providing a serene backdrop. Wooden deck chairs line the poolside, inviting relaxation in a natural setting.

4.98 out of 5 average rating, 221 reviews

Agriturismo La Villa - L'Olivo, Pool & Hot Tub

Superhost

The modern studio features a spacious bed with soft linens, flanked by bedside shelves. A minimalist kitchenette is visible in the background, complemented by light-colored cabinetry. Natural light filters in through the window, highlighting the tasteful green accent wall.

4.86 out of 5 average rating, 107 reviews

Japan Apartment Port Area with Balcony and Jacuzzi

Superhost

An exclusive terrace features a relaxing hot tub surrounded by a spacious seating area with light-colored cushions. Two sleek lounge chairs are positioned nearby, with the checkerboard floor adding a modern touch. Lush greenery complements the serene outdoor space.

4.84 out of 5 average rating, 223 reviews

The terrace of the olive trees in Lucca

The charming stone house showcases traditional Tuscan architecture, surrounded by lush greenery, including an olive tree. A small seating area with table and chairs is visible on the patio, offering a serene outdoor space. A clean, gravel driveway leads to the entrance.

4.96 out of 5 average rating, 192 reviews

Il Fienile di Tigliano (former barn in Vinci-Florence)

The exterior of the farmhouse showcases a three-story stone structure with a rustic charm. Surrounded by a grassy area, the building features a variety of windows and a distinct roofline, with a tree providing shade nearby.

4.93 out of 5 average rating, 135 reviews

"La Casa di Gigi" (GG House)

Family- and pet-friendly home rentals

A traditional stone farmhouse is set against a backdrop of lush greenery and a bright blue sky. The structure features a terrace with a sail canopy, surrounded by a well-kept garden with olive trees and flowering plants, offering a peaceful outdoor atmosphere.

4.95 out of 5 average rating, 128 reviews

Nature, mountains and relaxation: holidays in Alta Versilia

4.99 out of 5 average rating, 129 reviews

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.

Villa

Belforti Tower

An outdoor seating area is shown with a sturdy wooden table surrounded by several chairs. An umbrella provides shade, while the rustic stone walls of the ancient structure frame the picturesque view of the valley beyond. A grassy area with a terracotta floor enhances the inviting ambiance.

4.95 out of 5 average rating, 219 reviews

AT THE CASTELLO DELLA MONTACCHITA WHOLE APARTMENT

A spacious living area features a comfortable sofa with accent pillows, positioned in front of a large television. An accessible kitchenette and dining area can be seen in the background, while a patterned area rug adds texture to the floor. The room is illuminated by natural light from an unseen source.

4.96 out of 5 average rating, 106 reviews

"LA BADESSA" APARTMENT

An open kitchen and dining area is displayed, featuring a central wooden table surrounded by four chairs. A charming cabinet and modern appliances can be seen. Natural light filters in through a large window, and pale green curtains add a touch of color.

4.9 out of 5 average rating, 309 reviews

Apt. with garden a stone's throw from the tower!

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.

4.95 out of 5 average rating, 188 reviews

Antico Borgo Ripostena – n. 8 Old House

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.

4.95 out of 5 average rating, 208 reviews

Casa Gave - Nature and relax in Tuscany

4.94 out of 5 average rating, 125 reviews

Villa

La Conchetta – Bolgheri

Family-friendly home rentals with a pool

A swimming pool is foregrounded with vibrant red roses, offering a striking contrast against the clear blue water. The panoramic view features rolling hills and the medieval towers of San Gimignano in the distance, with sun loungers arranged around the pool area.

4.95 out of 5 average rating, 139 reviews

Adalberto Apartment inside the Manor of Fulignano

4.97 out of 5 average rating, 148 reviews

An aerial view captures the serene layout of the estate, surrounded by lush greenery and rolling hills. The inviting pool is situated centrally, accompanied by sun loungers. Stone buildings harmonize with the natural landscape, reflecting the tranquil beauty of the Montagnola Senese.

Holiday home

Podere La Castellina - No. 1 COTTAGE

An independent stone cottage is surrounded by greenery, featuring a terracotta patio framed by a pergola. The cottage showcases wooden beams and green shuttered windows, with a gentle slope leading to the lush garden and distant trees.

4.92 out of 5 average rating, 146 reviews

Holiday in antique farm, Belvedere

A vintage-styled kitchen and dining area feature a small wooden table with colorful chairs, accompanied by a bicycle and a wall-mounted television. Kitchen appliances include a microwave and a minimalist cabinetry design. Natural light filters through a balcony door, opening to a garden view.

4.95 out of 5 average rating, 116 reviews

Vintage apartment with swimming pool in Chianti

4.92 out of 5 average rating, 108 reviews

An outdoor dining area features a spacious wooden table surrounded by dark wooden benches. The space is partially shaded by a terracotta-tiled roof, and greenery can be seen in the background, creating a natural setting for meals or gatherings.

Cottage

Tuscan cottage with swimming pool, Pet Friendly

An inviting living space features a cozy fireplace framed by a rustic stone wall. Natural light filters through floral-patterned curtains, illuminating a spacious sitting area with a two-seater sofa. A four-poster bed draped in sheer fabric enhances the room's charm, complemented by decorative lanterns.

4.91 out of 5 average rating, 182 reviews

Pieve di Caminino Historic Farm

4.96 out of 5 average rating, 105 reviews

A serene outdoor area features a newly constructed pool surrounded by a spacious patio. Sun loungers are positioned nearby, and vibrant yellow roses are visible in the foreground. Rolling hills and greenery create a picturesque backdrop under a clear blue sky.

Cottage

LIKE AT HOME! FAMILY COUNTRY HOUSE!

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.