The 13 Best Boutique Family Hotels in San Casciano In Val Di Pesa (2025)

Nestled within the rolling hills of Chianti, Villa Il Fedino is a splendid 14th-century villa that whispers tales of romance and history. With its elegant period furnishings, breathtaking views from the panoramic terrace, and an enchanting outdoor space, it offers a serene haven where luxury intertwines seamlessly with timeless charm.

Romantic Retreat - Sink into intimacy as you embrace the luxurious suites adorned with antique furnishings, high ceilings, and stunning vistas of lush vineyards and cypress trees, creating an idyllic backdrop for lovebirds.

Culinary Delights - Awake to the enticing aroma of fresh pastries and sizzling breakfast delights crafted by the talented chef Lorenzo, whose culinary creations transform each morning into a gastronomic experience, often filled with laughter and shared stories at the scenic patio.

Cultural Exploration - Embark on a journey through the rich tapestry of Tuscany with organized excursions to nearby Florence and Siena, where the charming hosts provide local insights that lead you to hidden gems and unforgettable experiences.

Guest Experiences - Picture yourself savoring breakfast indoors amidst historic decor, where the smell of freshly baked bread and sweet fruit dances in the air while the distant sound of laughter echoes from other guests sharing their plans for the day. Every moment feels like being part of a warm, family gathering.

Nestled among the enchanting hills of Chianti, Castello di Bibbione offers an intimate escape steeped in history and romance. With its sprawling gardens and breathtaking vistas, this elegant haven invites you to unwind by the shimmering outdoor pool or savor a glass of exquisite Chianti wine as the golden sun sets over the undulating landscape.

Romantic Break - Every corner of this majestic castle whispers romance—from the charming terracotta floors to the flickering lights of cozy fireplaces, perfect for lovers seeking a serene retreat.

Spa & Relaxation Lovers - Indulge in personalized massage treatments amidst tranquil surroundings, allowing the gentle sounds of nature to wash over you as you surrender to pure bliss.

Local Exploring - Venture out to discover the hidden gems of Tuscany with complimentary bicycles at your disposal, riding through quaint villages and lush vineyards that embody the essence of Italian charm.

Guest Experiences - Awakening each morning to the scent of freshly brewed coffee mingling with warm pastries, guests have relished making their own breakfast creations—a delightful start before exploring the stunning, rolling landscapes that feel like living art.

Nestled in the sun-kissed hills of the Chianti countryside, Villa I Barronci Resort & Spa is a luxurious Tuscan retreat that beckons lovers and adventurers alike. With breathtaking views that stretch across rolling vineyards and olive groves, this elegant villa offers an intimate escape where every moment feels like a whisper of romance.

Romantic Escape - Experience unparalleled privacy with enchanting surroundings that create a perfect backdrop for love. The soft rustle of leaves and the gentle serenade of birds provide a serene soundtrack as you lounge by the panoramic pool, sipping local Chianti wine.

Wellness Sanctuary - Indulge in rejuvenation at our exquisite spa, where the scent of essential oils mingles with warm steam from the Turkish bath. A soak in the hot tub eases tension as captivating views take your breath away, creating a sanctuary for total relaxation.

Culinary Delights - Awaken your senses with a sumptuous buffet breakfast featuring homemade pastries and fresh fruit, all prepared with love. Dine al fresco at the Panorama restaurant, where the aroma of traditional Tuscan dishes fills the air, promising unforgettable culinary experiences against a stunning valley backdrop.

Guest Experiences - Guests often marvel at the spectacular views, describing them as "ammmazing," while savoring the fresh offerings each morning. Many have shared moments of tranquility in their beautifully appointed rooms, reminiscing about the soft linens and the gentle sounds of nature that made their stay feel both luxurious and inviting.

Nestled amidst the rolling hills of the Chianti region, Castello di Cafaggio is a breathtaking retreat that echoes the charm of a bygone era while offering modern indulgences. With its sun-drenched terraces and luxuriant gardens, this enchanting property invites couples and families alike to experience the romance and tranquility of Tuscany in an intimate setting where every detail whispers comfort and elegance.

Total Relaxation - Unwind by the shimmering pool, where the gentle rustle of the olive trees dances with the soft melodies of chirping birds, creating a serene backdrop for total rejuvenation. Whether lounging on a plush sunbed or savoring a refreshing drink, every moment here feels like a blissful escape.

Outstanding Location - Just a stone's throw from Florence’s artistic heart and the rustic allure of local markets, guests will find themselves perfectly positioned to explore Italy’s rich culture and breathtaking landscapes. The panoramic views from the castle provide an ever-changing tapestry of colors at sunset, making every evening a picturesque memory.

Romantic Break - Experience the magic of shared moments as you stroll hand-in-hand through lush gardens, or enjoy breakfast al fresco, where the scent of freshly baked pastries mingles with the crisp morning air. Each cozy nook offers a whisper of romance, perfect for honeymooners and lovers seeking unforgettable experiences together.

Guest Experiences - One guest recalled the delightful surprise of finding a secluded terrace adorned with twinkling lights; it became their secret viewing spot for sunsets that painted the sky in vibrant hues. Families enjoyed playful afternoons by the pool, laughing over friendly games of ping pong as the captivating Tuscan landscape framed their joyful moments.

Nestled in the rolling hills of Mercatale Val Di Pesa, the Castello Di Gabbiano is a 14th-century treasure that radiates warmth and timeless elegance. Surrounded by lush vineyards and fragrant olive groves, this enchanting castle invites you to indulge in a romantic escape where the whispers of history dance with modern comforts.

Romantic Hideaway - With its stunning architecture and intimate nooks, every corner of the Castello inspires romance. Enjoy leisurely strolls through the picturesque gardens or relax under the Tuscan sun beside the sparkling outdoor pool, making each moment feel like a stolen getaway.

Culinary Delights - Awaken your palate with sumptuous Tuscan breakfasts served in charming drawing rooms, or dine al fresco amidst blooming flowers. The restaurant, located just a stone's throw away, tantalizes with regional dishes crafted from the freshest local ingredients, inviting guests to savor the essence of Italy.

Artistic Oasis - The blend of classic decor and contemporary art exhibitions creates an atmosphere that is both visually captivating and deeply inspiring. Wander the halls and discover thoughtfully curated artworks that add a unique flair to this historical gem, making each visit a feast for the senses.

Guest Experiences - Guests often find themselves enchanted by the delightful aroma of fresh-baked pastries wafting through the castle during breakfast, while the warm smiles and attentive gestures of the staff make every interaction feel personal and heartfelt, leaving a lasting impression long after departure.

Nestled amidst the enchanting hills that cradle Florence, I Parigi Corbinelli Residenze unveils a tapestry of history and serenity, offering an idyllic escape from the city's vibrant pulse. Set within a 14th-century complex, this elegant haven invites you to bask in breathtaking views from its medieval tower, where romance flourishes and tranquility reigns supreme.

Romantic Getaway - Experience the allure of a bygone era as you stroll through beautifully manicured gardens, hand in hand with your loved one, listening to the gentle rustle of olive trees swaying in the soft Tuscan breeze.

Historic Charm - Step into a world steeped in history, where the echoes of the past create a unique ambiance; wander through spacious accommodations adorned with rich textures that evoke centuries of stories waiting to be told.

Total Relaxation - Rejuvenate your senses by the inviting pool, where the sun's golden rays dance on the water’s surface, and the aroma of fresh coffee mingles with the scent of blooming lavender as you savor delightful breakfasts served alfresco during the warm summer days.

Guest Experiences - Amidst the serene backdrop, guests have marveled at the whimsical charm of their rooms, many recalling moments spent in a tower suite, sipping wine while gazing out over a magical landscape that felt like stepping into a painting.

Nestled amidst the rolling hills of the enchanting Chianti region, Antica Pieve B&B is a sanctuary of rustic charm and refined elegance. As sunlight dances across the vibrant landscape, this Tuscan haven invites couples and travelers alike to indulge in an authentic Italian experience steeped in warmth and hospitality.

Romantic Break - Whisk your partner away for a dreamy escape where candlelit dinners are accompanied by the soft glow of the setting sun, and each morning unfolds with fresh pastries wafting through the air, beckoning you to savor the day together.

Total Relaxation - Unwind in the inviting embrace of our swimming pool, where the soothing sounds of nature harmonize with the gentle rustle of leaves, creating a tranquil oasis perfect for lazy afternoons under the Tuscan sun.

Cultural Explorers - Venture beyond the serene grounds to discover the rich tapestry of nearby villages, where wine tastings and artisanal markets await, allowing you to immerse yourself in the culinary traditions that define this captivating region.

Guest Experiences - Imagine waking to the aromatic scent of seasonal fruit and freshly baked bread; guests have often shared how Mama Katia’s warm smile and attentive service made breakfast feel like a cherished family gathering, showcasing the essence of true Italian hospitality.

Nestled among the rolling hills of Montespertoli, Villa Le Calvane is a luxurious escape where elegance dances with authenticity. Surrounded by lush vineyards and fragrant olive groves, this enchanting retreat invites you to unwind in an atmosphere rich with Tuscan charm, making it the perfect haven for couples seeking romance or friends looking for a serene getaway.

Culinary Delights - Indulge in a gastronomic journey at the on-site restaurant, where each meal is a celebration of local flavors crafted with fresh, seasonal ingredients. Dinners unfold like cherished rituals, as guests savor exquisite tasting menus paired with fine wines, leaving them enchanted by every bite.

Serene Wellness Retreat - Rejuvenate your spirit in the inviting hot tub or take a refreshing dip in the stunning infinity pool that seems to spill into the horizon. The tranquility of the surroundings envelops you, allowing moments of reflection while soaking up the breathtaking views of the Chianti landscape.

Intimate Luxury - Each room at Villa Le Calvane is a sanctuary of comfort, designed with elegant touches and modern amenities. Guests are greeted with soft textiles, plush bathrobes, and the sweet aroma of nature wafting through their windows, creating a space that feels both intimate and refined.

Guest Experiences - As dawn broke, one guest savored the warm croissants, still flaky from the oven, accompanied by rich, aromatic coffee—a moment enhanced by the gentle sounds of birds chirping outside. Another shared how the staff’s genuine smiles felt like a warm embrace, turning simple greetings into delightful connections that lingered long after their stay.

Nestled among the rolling green hills of Tuscany, Tenuta Torre Rossa Farm & Apartments is a serene retreat where rustic charm meets modern luxury. With the majestic backdrop of Florence just a stone's throw away, this charming country house invites you to unwind in its spacious, artfully decorated apartments, each offering breathtaking views and an intimate connection to the pastoral landscape.

Artworks - Every corner of Tenuta Torre Rossa tells a story, with vibrant floral designs and elegant white furnishings that create a canvas of warmth and comfort, echoing the rich artistic heritage of Tuscany.

Total Relaxation - Bask in tranquility by the shimmering swimming pool, surrounded by olive groves and shaded gardens, where the gentle rustle of leaves creates a soothing symphony that invites you to lose track of time.

Country Escape - Amidst 20 hectares of lush farmland, experience the simple joy of picking fresh olives or strolling through sun-drenched fields, a perfect way to reconnect with nature and savor the essence of Italian countryside life.

Guest Experiences - As the sun dipped below the horizon, guests relished the magical moment when the pool transformed into a mirror reflecting Florence’s twinkling lights, while fragrant aromas from nearby Tuscan kitchens wafted through the air, evoking a sense of home-cooked warmth.

Nestled in the heart of Tuscany's enchanting Chianti wine region, COMO Castello Del Nero beckons with its rich history and breathtaking vistas. This elegantly restored 12th-century castle envelops guests in a world where luxury meets authentic Italian charm, creating an intimate sanctuary perfect for romantic getaways or serene retreats.

Total Relaxation - Indulge in the tranquil oasis of the COMO Shambhala Retreat, where the soothing scent of essential oils wafts through the air as you unwind by the outdoor pool, surrounded by lush olive groves that whisper stories of centuries past.

Culinary Excellence - Savor Michelin-starred creations at La Torre Restaurant, set in the former stables of the castle; here, the aroma of freshly baked bread mingles with local wines, promising a culinary journey that dances on your palate while offering sweeping views of the rolling Tuscan hills.

Historic Charm - Every corner of this majestic castle tells a story; from the intricately painted frescoes in your uniquely designed room to the creaking wooden beams above, the atmosphere exudes the warmth of history while providing modern luxury and comfort.

Guest Experiences - As the sunlight filtered through the ancient windows, one guest cherished those quiet moments spent lounging in a plush bathrobe, listening to the distant laughter of a couple enjoying a romantic picnic amidst the vineyards, perfectly framing their idyllic escape.

Nestled in a sun-kissed corner of the Tuscan countryside, Il Paluffo is a romantic sanctuary where time flows gently like the wine from nearby vineyards. This enchanting 15th-century farmhouse, with its rustic charm and historic features, invites couples and travelers alike to immerse themselves in the serene beauty of ancient stone walls and wooden beams, all while enjoying modern comforts and eco-friendly luxury.

Natural Oasis - Dive into the refreshing embrace of our ecological pool, surrounded by lush gardens where resident frogs croak their evening serenades. Experience the soothing sensation of swimming under the open sky as the sun sets behind rolling hills, creating a picturesque backdrop that soothes the soul.

Culinary Delights - Savor a delightful breakfast served al fresco in our charming courtyard, where the aroma of freshly baked pastries mingles with the sweet scent of blooming flowers. Each bite is a taste of Tuscany, crafted with love and local ingredients, making mornings here a memorable ritual.

Cultural Exploration - With bicycles available for free, embark on a spontaneous adventure through the enchanting landscapes dotted with olive groves and vineyards. The breathtaking views transform each ride into a pastoral painting, beckoning you to discover the hidden gems of Certaldo and beyond.

Guest Experiences - Guests often recount how they lounged on the communal terrace, enveloped by gentle breezes, while sharing stories amidst cozy sofas. The helpful staff, especially Claudia, are known for their warm hospitality, going above and beyond, whether it was recommending quaint local eateries or sharing the joy of spotting playful frogs by the natural pool.

Nestled in the sun-kissed hills of Chianti, Agriturismo Villa Ulivello offers an enchanting retreat where rustic charm meets modern elegance. Surrounded by lush olive groves and breathtaking vineyards, this intimate sanctuary invites you to unwind, breathe deeply, and savor the slow rhythm of Italian countryside life.

Romantic Break - With its cozy rooms featuring private terraces and stunning views, every corner of this haven is designed for romance, from shared sunsets over the rolling landscape to candlelit dinners with local delicacies.

Country Escape - Escape the hustle and bustle of everyday life as you explore winding paths through vineyards or sip on a glass of Chianti while basking in the serene ambiance of the beautifully landscaped gardens.

Spa & Relaxation - Indulge in moments of tranquility with holistic wellness treatments that let you reconnect with nature, all while the gentle sound of rustling leaves and distant birdsong serenades your soul.

Guest Experiences - Guests recount waking up to the rich aroma of fresh pastries wafting through sunlit corridors, often greeted with warm smiles from staff who make you feel like family amidst the peaceful silence, occasionally punctuated by laughter from fellow travelers enjoying a leisurely breakfast.

Perched majestically in the rolling hills of Greve in Chianti, Castello Vicchiomaggio invites you to step back in time, where luxury meets romance in a historic castle dating back to the 1400s. Surrounded by sprawling vineyards and breathtaking views of the Val di Greve valley, this enchanting retreat offers an intimate escape, perfect for couples and those seeking a slice of Tuscan paradise.

Romantic Getaway - Whisk your loved one away to this charming haven, where candlelit dinners in a Renaissance-style dining room are enhanced by the soft glow of arched ceilings, creating an ambiance steeped in history and intimacy.

Culinary Delights - Savor authentic Tuscan cuisine made from local ingredients, with every dish crafted to perfection. The restaurant’s exquisite offerings, paired with the estate's own Chianti wine, promise a delectable experience that lingers long after your meal.

Stunning Views - Relax by the shimmering swimming pool, where the gentle sound of rustling leaves harmonizes with panoramic vistas of the undulating hills, forming a picturesque backdrop that transforms each moment into a postcard-perfect memory.

Guest Experiences - As twilight descends, guests often find themselves enchanted by the fragrance of blooming flowers wafting through their open window, while the laughter and clinking of glasses from nearby tables create a joyful symphony of celebration under the starry Tuscan sky.