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Family-friendly vacation rentals in Monteriggioni

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Top-rated family-friendly rentals in Monteriggioni

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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.

Villa in Castellina in Chianti

4.93 out of 5 average rating, 226 reviews

Il Villino Farmhouse

Intero piano superiore della Villa Padronale appena ristrutturata in stile tradizionale toscano.Gli alti soffitti con le travi a vista rendono il posto accogliente e perfetto per famiglie o gruppi di amici.Nella casa si trovano due grandi camini(in salotto e cucina)funzionali.Alloggio privato, non condiviso. La casa ha una ampia terrazza coperta,giardino con divani,bbq,firepit,parking privato. La piscina tra gli ulivi e i vigneti e' ideale per il relax ha un accesso privato alla zona condivisa

Top guest favorite

A sitting room features ornate wooden beams on the ceiling and rich golden walls. A shell-shaped sofa is positioned prominently, surrounded by decorative wooden furnishings and a bookshelf. A classic rug covers the floor, adding warmth. Wooden accents infuse the space with historical charm.

Apartment in Centro Storico

5 out of 5 average rating, 522 reviews

Renaissance Apartment Touch the Dome

Inspired by the most fascinating artistic era in human history, the Renaissance, each of my homes is a tribute to the elegance, harmony, and craftsmanship that defined that golden age. Step inside and be transported. You’ll not only see the Renaissance — you’ll feel it in the atmosphere, in the light, and in the soul of each space. Discover also The Renaissance & Baroque apartment: https://www.airbnb.it/rooms/30229178?guests=1&adults=1&s=67&unique_share_id=c0087742-7346-4511-9bcd-198bbe23c1b4

Top guest favorite

A charming cottage is shown with a terracotta facade and a tiled roof. A small table with two chairs is set on a patio, surrounded by potted plants. Lush greenery and trees can be seen in the background under a clear blue sky.

Guesthouse in Macciano

4.97 out of 5 average rating, 177 reviews

Tuscan cottage with an heavenly view

Heaven's Window takes your breath away. As our only guests, you will be surrounded by infinite views, endless tranquility, sounds of singing birds and calling deer. Down the valley and on your walks you may spot foxes ferrets and wild boar. Collect porcupine quills. Breathe! Halfway between Rome and Florence. Close to Siena, Val d’Orcia and countless hot springs . A private paradise surrounded by divine dining and hilltop jewels of antiquity like Montepulciano and Montalcino of sublime wines.

Top guest favorite

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, 266 reviews

Podere Vergianoni immerso nelChianti con piscina

Podere Vergianoni è un antica e autentica casa colonica risalente al 1600 situata nelle splendide colline del Chianti in Toscana . L'appartamento è arredato in perfetto stile tradizionale locale dell'antica Toscana : antiche travi in legno, pavimenti in cotto e arredamenti unici. Nel grande cortile esterno troverete a vostra disposizione una grande piscina con terrazza panoramica che si affaccia su una valle con vista mozzafiato su vigneti e oliveti dove godersi tramonti spettacolari.

The stone farmhouse, characterized by a rustic façade, features arched doorways and shuttered windows. Lush greenery surrounds the entrance, offering a serene landscape. A gravel driveway leads to the main entrance, highlighting the spaciousness of the property.

Farm stay in Monteriggioni

4.89 out of 5 average rating, 101 reviews

Podere Casalino - Il Gatto

Nestled near the enchanting Monteriggioni Castle, "Il Casalino" embodies our passion and dedication to restoring a historic farmhouse. My husband and I have poured our hearts into crafting two apartments for rent: Il Gatto and La Pergola. If you have any questions, please reach out to me. Your inquiries are of the utmost importance, and I am committed to promptly responding to your messages. We eagerly anticipate the opportunity to welcome you to "Il Casalino" soon! Best regards, Laura

Top guest favorite

An outdoor dining area is presented under a wooden pergola, featuring a long table surrounded by matching chairs. A well-maintained garden is visible in the background, with grassy patches and stone walls adding to the serene ambiance.

Villa in Monteriggioni

4.97 out of 5 average rating, 159 reviews

Villa dei 2 Ulivi (Abbadia Isola)

FULLY AIR CONDITIONED, modern 6BR/4BA VILLA on Via Francigena: an enchanted paradise for friends & families with kids (trampoline, basketball area, soccer & volley/beach tennis nets, fossball, table tennis) & w. pets (fenced garden). Located in the small village Abbadia Isola in the shadow of the medieval castle of Monteriggioni, right on the path the ancient road & pilgrim route running from France to Rome (via Francigena) A.k.A FAMILY GROUPS KIDS FRIENDS dream VILLA Siena 12mn (ABB)

Top guest favorite

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

4.96 out of 5 average rating, 251 reviews

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.

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.

Farm stay in Sovicille

4.98 out of 5 average rating, 212 reviews

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

Immersed in the green woods of the Senese hills, the beating heart of Tuscany, lies the La Villa estate. Characterized by a large park with swimming pool, gazebo, barbecue area and relaxation area, the farmhouse stands out for its strong link with the Tuscan tradition: a suggestive path will guide you to discover the woods surrounding the farm among olive trees and fields of lavender in bloom, among which you can forget the passage of time and enjoy the charms of nature.

The countryside property is nestled among lush greenery, featuring rustic architecture and terracotta roofs. Surrounded by rolling hills and trees, the natural landscape creates a peaceful setting. A gravel path leads to the house, enhancing the connection to the serene outdoor environment.

Farm stay in Sovicille

4.93 out of 5 average rating, 147 reviews

Casa al Gianni - Olmo

Ciao, siamo Cristina & Carmelo! Ti invitiamo a scoprire il fascino rustico e l'autenticità di "Casa al Gianni", il nostro agriturismo nel cuore della campagna Toscana a 20 minuti da Siena. Dopo una recente ristrutturazione, i nostri alloggi sono pronti ad accoglierti con tutto il confort moderno senza perdere l'essenza della tradizione. Nell'Appartamento Olmo, ti aspettano letti completamente nuovi, promessa di sonni tranquilli e rigeneranti, nuova cucina e nuovo bagno.

Top guest favorite

A charming country loft is enveloped in lush green vines, with steps leading from a grassy area to the entrance. Sun loungers are situated on the lawn, providing a serene space for relaxation. This rustic exterior is framed by trees and open skies.

4.95 out of 5 average rating, 239 reviews

Siena Country Loft Hideway

Country loft, ideal gateway for a couple looking to experience the flavour of Tuscan countryside 2 bathrooms, one with shower and one with bath tub with unique windows view Fully equipped kitchen Eclectic style with antique accents Endless rolling hills view, modern amenities in typical country side setting Concierge service upon request Wifi Internet connection Only 7km far from Siena town

Top guest favorite

The image features a serene infinity pool reflecting the surrounding trees and villa during sunset. Sun loungers are positioned beside the pool, and the well-maintained outdoor area offers a tranquil ambiance enhanced by the natural landscape.

Farm stay in Pisa

4.99 out of 5 average rating, 304 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.

Top guest favorite

An infinity pool reflects the sky, surrounded by olive trees and well-manicured gardens. Comfortable lounge chairs are placed neatly along the pool deck under shaded umbrellas. A gradual elevation creates a seamless transition between the pool area and scenic countryside views.

Farm stay in Palaia

4.98 out of 5 average rating, 171 reviews

Countryside Dream farm in Tuscany

Great place in the middle of Tuscan Hills, you will be surrounded 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.

Vacation rentals for every style

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Popular amenities for Monteriggioni family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

An outdoor dining area is surrounded by lush greenery and flowering plants, featuring a circular table with four elegant wrought iron chairs. A cozy blanket is draped over one chair, and a scenic view of rolling hills extends in the background under a muted sky.

Apartment in Monteroni d'Arbia

4.96 out of 5 average rating, 252 reviews

Appartamento "Red Rose" con vista su Siena.

Top guest favorite

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.

Home in Barberino Tavarnelle

5 out of 5 average rating, 114 reviews

Infinity pool in Chianti

The villa's exterior is highlighted by a modern structure with large glass doors and a gently sloping roof. It is surrounded by lush greenery and features a patio area with steps leading to the entrance. Soft lighting illuminates the garden, creating a serene evening ambiance.

Villa in Montepulciano

4.95 out of 5 average rating, 230 reviews

Amazing Tuscany Villa, FREE parking

Top guest favorite

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.

Home in Figline e Incisa Valdarno

4.96 out of 5 average rating, 108 reviews

Torretta Apartment

A sunlit swimming pool is situated in an expansive landscaped area, surrounded by neatly trimmed grass and lush trees. The charming building stands in the background, showcasing traditional architecture, while cypress trees line the horizon, adding to the tranquil countryside atmosphere.

Villa in Monteroni d'Arbia

4.98 out of 5 average rating, 102 reviews

San Giovanni in Poggio, villa Meriggio 95mq

A rustic dining area features a long wooden table set for eight, with simple tableware and napkins. A large window allows natural light to fill the space, offering a view of the vibrant garden outside, where a hammock is visible in the background.

Home in Anghiari

4.86 out of 5 average rating, 143 reviews

Tuscan dream in the ancient Tobacco's villa, sauna

A wooden hot tub is positioned against a stone wall, surrounded by lush greenery. Two individuals relax within the tub, illuminated by soft lighting from nearby lanterns, creating a serene evening atmosphere.

Condo in Casole d'Elsa

4.93 out of 5 average rating, 162 reviews

La Casetta

Top guest favorite

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.

Farm stay in Greve in Chianti

4.99 out of 5 average rating, 386 reviews

Typical Tuscan country house

Family- and pet-friendly home rentals

Top guest favorite

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 in Montecatini Val di Cecina

4.99 out of 5 average rating, 122 reviews

Torre dei Belforti

Top guest favorite

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.

Apartment in San Gimignano

4.97 out of 5 average rating, 222 reviews

Casa Irene

Top guest favorite

The image captures a serene outdoor setting featuring a swimming pool surrounded by a well-maintained lawn. Several sun loungers positioned around the pool invite relaxation, while the rustic house and lush greenery complete the idyllic scene.

Vacation home in Panzano

4.97 out of 5 average rating, 156 reviews

Fienile Santa Teresa

The image captures a green hillside landscape, with a stone farmhouse situated at the center. Lined cypress trees create a pathway in the background, while the garden surrounding the home features a pool. The sky is clear and bright, enhancing the serene environment.

Farm stay in Campiglia D'orcia

4.94 out of 5 average rating, 433 reviews

Agriturismo Poggio Bicchieri ap. Poesia

Top guest favorite

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.

Home in Tavarnelle Val di Pesa

4.96 out of 5 average rating, 302 reviews

Casa Al Poggio & Chianti view

Top guest favorite

A decorative wall shelf is embedded in a stone wall, featuring a small potted plant and a light fixture above. Below the plant, a set of wine glasses is arranged on a glass surface, adding a touch of elegance to the rustic backdrop.

Home in Colle di Val d'Elsa

4.96 out of 5 average rating, 251 reviews

Casa per la Costa

Top guest favorite

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

4.94 out of 5 average rating, 181 reviews

Antico Borgo Ripostena – n. 8 Casa Vecchia

Top guest favorite

A rustic rural complex is depicted, featuring a stone building with a terracotta roof. Surrounding greenery enhances the setting, and a gravel path leads to the entrance. The scene is accentuated by a large tree and the clear sky above.

Condo in Monteriggioni

4.92 out of 5 average rating, 127 reviews

Il Vecchio Noce

Family-friendly home rentals with a pool

Top guest favorite

A private pool is situated amid well-maintained gardens, surrounded by varied greenery and tall trees. Colorful loungers are arranged along the patio, inviting relaxation. The clear water of the pool reflects the sky, enhancing the serene outdoor setting.

Home in Castiglion Fiorentino

5 out of 5 average rating, 40 reviews

Hidden gem in Tuscany

Top guest favorite

Villa in Poggibonsi

4.92 out of 5 average rating, 50 reviews

Villa with pool in Chianti Area

Top guest favorite

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.

Home in Barberino Tavarnelle

4.97 out of 5 average rating, 75 reviews

Podere Tignano, 4-bedroom villa in the Chianti!

A stone facade is viewed from a well-maintained garden, featuring lush green grass and neatly trimmed hedges. A wooden door is visible, leading into a charming interior, while the house's rustic architecture complements the serene landscape under a clear blue sky.

Home in Castellina in Chianti

4.98 out of 5 average rating, 104 reviews

Explore Chianti from a Charming Stone House

Top guest favorite

A traditional Tuscan farmhouse is set against a backdrop of rolling hills. The property features a spacious pool surrounded by lush green grass and neatly trimmed hedges. Tall cypress trees provide natural framing, enhancing the serene outdoor atmosphere.

Villa in Montenero d'Orcia

5 out of 5 average rating, 28 reviews

Tuscany Villa With Pool & Magnificent Garden

Top guest favorite

The charming barn features a rustic stone exterior, framed by lush greenery. A spacious patio can be seen, adorned with vibrant flowers and equipped with outdoor seating and a shaded area. The structure is surrounded by well-maintained lawn and trees, enhancing the tranquil atmosphere.

Barn in Monteriggioni

5 out of 5 average rating, 50 reviews

Charming Barn with Pool - Chianti Area

4.94 out of 5 average rating, 16 reviews

Il Fienile del Borgo - Monteriggioni

Top guest favorite

An infinity pool reflects a clear blue sky, offering expansive views of rolling hills and lush valleys. A sun umbrella provides shade beside the pool, while a charming rustic structure is positioned nearby, surrounded by trees and Mediterranean flora.

Barn in Castellina in Chianti

5 out of 5 average rating, 71 reviews

Cipressini 1 - Swimming pool and stunning view

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