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Family-friendly holiday rentals in Monteriggioni

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Top-rated family-friendly rentals in Monteriggioni

Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

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Top Guest favourite
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

Podere Casalino - Il Gatto

Set in the peaceful countryside near the Monteriggioni Castle, Il Casalino is the result of our love for restoring an old Tuscan farmhouse. My husband and I have carefully created two apartments for our guests: Il Gatto and La Pergola. We want you to feel at home from the very first moment. If you have any questions, feel free to message me: I will reply as quickly as possible. We truly look forward to welcoming you to Il Casalino and sharing this special place with you! Warm regards, Laura

Indoor spacesKitchenLocation

4.91 out of 5 average rating, 117 reviews
Top Guest favourite
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 immerso nelChianti con piscina

Podere Vergianoni è un antica proprietà del 1600 a gestione familiare situato nelle splendide colline del Chianti in Toscana con la possibilità di organizzare navetta privata e esperienze locali direttamente con la nostra famiglia . 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 e vigneti con tramonti unici.

Indoor spacesFamilyBarbecue

5.0 out of 5 average rating, 352 reviews
Top Guest favourite
The living area features polished wooden floors and a cozy sofa. A painting is displayed above a brick fireplace, while a television is placed on a small cabinet. A staircase with a wooden handrail leads to the upper level, illuminated by soft wall lights.
Condo in Colle di Val d'Elsa

DorminColle - Appartamento in stile toscano

Appartamento luminoso e spazioso, composto da confortevole camera matrimoniale con tv, condizionatore portatile, con al suo interno bagno completo di doccia e servizi igienici. Terzo posto letto situato in caratteristica area soppalcata con travi in legno dotato di letto. Ampia cucina dotata di lavastoviglie, macchina del caffè, microonde, erogatore acqua filtrata, Salone con tv e divano, sala da pranzo con vista sul Borgo Antico. Parcheggio gratuito a 150 mt visibile dell’appartamento.

FamilyIndoor spacesDecor

4.97 out of 5 average rating, 253 reviews
Top Guest favourite
Home in Colle di Val d'Elsa

La Casa nel Vicolo - Colle di Val d'Elsa

Posizione centralissima, casa completamente ristrutturata nel 2023, accogliente e silenziosa, dotata di ogni confort. Ingresso indipendente. Situata a 50 mt. da Piazza Arnolfo di Cambio e a 300 mt. dal centro storico (raggiungibile a piedi o con l'ascensore), per chi viaggia in autobus la fermata è a soli 100 mt. Posizione strategica per visitare Siena, Firenze, San Gimignano, Volterra, Colline del Chianti e per chi vuole percorrere la Via Francigena o visitare il Parco Fluviale dell'Elsa.

FamilyIndoor spacesLaundry

4.99 out of 5 average rating, 135 reviews
Guest favourite
Villa in Monteriggioni

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)

KitchenIndoor spacesLaundry

4.97 out of 5 average rating, 174 reviews
Top Guest favourite
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

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.

KitchenIndoor spacesCheck-in

4.95 out of 5 average rating, 297 reviews
Top Guest favourite
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.
Holiday home in loc. Simignano

Casa al Gianni - Quercia

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!

FamilyIndoor spacesLaundry

4.93 out of 5 average rating, 244 reviews
Top Guest favourite
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.
Villa in Barberino Tavarnelle

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.

FamilyIndoor spacesBathroom

4.98 out of 5 average rating, 107 reviews
Top Guest favourite
Farm stay in Sovicille

Agriturismo La Villa - Il Ciliegio, Pool & Garden

We are pleased to welcome you to our Cherry Tree House, the last newly renovated jewel of the Agriturismo La Villa. Located on second floor, built among the rocks of the typical Senese countryside, our new home will be ready to lull you into all kinds of comforts: free wifi, swimming pool, barbecue area, air conditioning, smart TV. private parking, wood and garden, just 40 steps away, overlooking our lavender and olive grove.

FamilyKitchenGetting around

4.95 out of 5 average rating, 146 reviews
Top Guest favourite
An outdoor pool area is surrounded by olive trees and vineyards, with sun loungers and shaded umbrellas arranged on the deck. Soft sunlight bathes the scene, highlighting the peaceful setting. A gravel path leads around the pool, inviting relaxation amid the natural landscape.
Apartment in Monteriggioni

Comfort Apartment tra i vigneti del Chianti

Appartamento al piano superiore della struttura caratterizzato da una vista meravigliosa sulle colline del Chianti, uliveti o sul patio. Ristrutturato mantenendo il fascino delle loro antiche mura ma aggiungendo ogni comfort. Comprende soggiorno, angolo cottura, una camera da letto matrimoniale, un bagno privato con doccia, aria condizionata.

FamilyIndoor spacesLong stay

4.93 out of 5 average rating, 455 reviews
Guest favourite
Home in Monteriggioni

Next to castle of Villa-Siena. heart Francigena

The house has a special charm that I'm sure will captivate you. You will be excited to sip a glass of wine in the beautiful Hague or stroll through the ancient paths of the Via Francigena (stage n. 32 from Monteriggioni to Siena) which overlooks the living room .

KitchenFamilyBreakfast

4.84 out of 5 average rating, 158 reviews
Guest favourite
A spacious living room is presented with terracotta flooring and wooden beams overhead. A comfortable sofa arrangement surrounds a wooden coffee table, with a flat-screen TV positioned nearby. Natural light filters through the windows, enhancing the inviting ambiance.
Home in Monteriggioni

Siena Countryside Colle Ciupi

Countryside Villa apartment. Located in the nearby of Siena (Colle Ciupi, 10 kms away) Ground floor: Kitchen, living room with fireplace, bathroom with shower. First Floor: 3 Double Bedrooms and 2 bathrooms, outdoor with courtyard and huge garden

KitchenIndoor spacesHospitality

4.9 out of 5 average rating, 217 reviews

Popular amenities for Monteriggioni family-friendly rentals

KitchenWi-FiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Top Guest favourite
The lounge features elegant walls adorned with intricate frescoes and moldings. A large mirror reflects the refined decor. Two white armchairs and a colorful sofa provide seating, while a coffee table rests on a patterned rug before a decorative fireplace.
Apartment in Siena

Luxury frescoed apartment in the historical center

Indoor spacesFamilyQuiet

4.97 out of 5 average rating, 116 reviews
Top Guest favourite
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

KitchenFamilyTV

4.99 out of 5 average rating, 155 reviews
Top Guest favourite
An elegantly furnished living room features classic decor, including a chandelier and ornate details. Large windows offer views of the city's architectural highlights. Comfortable seating arrangements, including a tufted sofa and armchairs, are arranged around a glass coffee table, enhancing the room's inviting ambiance.
Home in Siena

Domus Nannini - Loggia Salimbeni SPA

FamilyIndoor spacesHospitality

4.96 out of 5 average rating, 156 reviews
Top Guest favourite
A warm living area is presented, featuring a comfortable sofa adorned with soft pillows and a round dining table. The space is illuminated by wall sconces, while an arched entryway leads to another room. Large windows allow natural light to fill the area.
Farm stay in Gaiole in Chianti

La Pieve - the house next to the church

KitchenIndoor spacesLong stay

4.97 out of 5 average rating, 117 reviews
Top Guest favourite
Farm stay in Greve in Chianti

Agriturismo nel Chianti con Piscina

FamilyIndoor spacesValue

4.99 out of 5 average rating, 516 reviews
Guest favourite
A sparkling swimming pool is surrounded by sun loungers and umbrellas, offering a relaxing space for guests. The rustic farmhouse, with its stone exterior, is visible in the background, amidst lush greenery and trees under a partly cloudy sky.
Holiday home in Castelnuovo Berardenga

PIERFANTINI private Chianti house ♿️ 🏊‍♂️ 🐶

FamilyIndoor spacesLocation

4.91 out of 5 average rating, 100 reviews
Top Guest favourite
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.

KitchenIndoor spacesQuiet

4.95 out of 5 average rating, 221 reviews
Guest favourite
A bright bedroom features a spacious bed with light linens and a decorative throw. Natural light enters through open double windows, revealing a private terrace. A television and a small desk with a chair are present, while two bedside tables with lamps offer soft lighting.
Holiday home in Monteroni d'Arbia

White lily con vista su Siena

Indoor spacesFamilyWalkability

4.92 out of 5 average rating, 113 reviews

Family- and pet-friendly home rentals

Top Guest favourite
A living area is seen with a light-colored sofa facing a flat-screen TV on a wooden unit. A glass coffee table is positioned in front of the sofa, and natural light filters through sheer curtains. A black chair and decorative items are present on shelves.
Condo in Castellina Scalo

Sopra la Posta

Indoor spacesKitchenPets

4.98 out of 5 average rating, 126 reviews
Top Guest favourite
A shaded outdoor terrace features a wooden pergola draped with green vines. A round table is set with a potted plant at its center, surrounded by several chairs. Stone paths lead to the entrance of the house, framed by blooming flowerbeds.
Home in Siena

Secret Garden Siena

FamilyIndoor spacesQuiet

4.98 out of 5 average rating, 220 reviews
Top Guest favourite
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

FamilyIndoor spacesHospitality

4.92 out of 5 average rating, 389 reviews
Guest favourite
A charming stone farmhouse is showcased, featuring traditional architecture with a tiled roof and multiple windows. A wheelbarrow filled with flowers is positioned on the grassy front lawn, complemented by potted plants and an outdoor light fixture, enhancing the rural setting.
Home in Quercegrossa

Casolare nel Chianti, Siena Toscana

Indoor spacesFamilyCondition

4.83 out of 5 average rating, 168 reviews
Guest favourite
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

Villa Padronale - IlVillinoFarmhouse

KitchenIndoor spacesLayout

4.93 out of 5 average rating, 255 reviews
Top Guest favourite
Farm stay in Siena

Typical Tuscan Country House WITH A/C

KitchenFamilyNearby

4.98 out of 5 average rating, 294 reviews
Guest favourite
Villa in Siena

Villa Capanna, Private Pool, Breathtaking Views

KitchenFamilyAir conditioning

4.89 out of 5 average rating, 309 reviews
Top Guest favourite
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

Bellissimo borgo medievale!!!

Indoor spacesKitchenHiking

4.99 out of 5 average rating, 473 reviews

Family-friendly home rentals with a pool

Top Guest favourite
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.
Home in Castellina in Chianti

Private Chianti Cottage, Garden & Vineyard Views

Indoor spacesFamilyCheckout

4.99 out of 5 average rating, 137 reviews
Top Guest favourite
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

Explore Chianti from a Charming Stone House

KitchenFamilyShared spaces

4.98 out of 5 average rating, 123 reviews
Top Guest favourite
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.
Home in San Filippo a Ponzano

Infinity pool in Chianti 1

KitchenIndoor spacesCondition

5.0 out of 5 average rating, 142 reviews
Top Guest favourite
Villa in Tignano

Villa Isabella

KitchenIndoor spacesAccess

4.96 out of 5 average rating, 209 reviews
Top Guest favourite
Apartment in Castellina in Chianti

Dolce vita nel Chianti. Piscina e Relax

FamilyIndoor spacesWalkability

4.85 out of 5 average rating, 354 reviews
Top Guest favourite
Home in Montaione

Cercis - La Palmierina

Indoor spacesFamilyHospitality

4.96 out of 5 average rating, 146 reviews
Top Guest favourite
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.
Cottage in Barberino Tavarnelle

Stone House with Exclusive Pool Codilungo in Chianti

FamilyKitchenNearby

4.98 out of 5 average rating, 218 reviews
Guest favourite
Aerial view of Podere degli Olivi, showcasing a rustic building surrounded by lush olive groves and cypress trees. A tranquil swimming pool is visible in the foreground, and the medieval towers of San Gimignano rise in the background against a clear blue sky.
Apartment in San Gimignano

Apartment Melogranowith great views

FamilyKitchenBathroom

4.88 out of 5 average rating, 183 reviews

Destinations to explore