The 6 Best Boutique Hotels with Private Pool in Chianti (2025)

Nestled in the rolling hills of the Chianti Region, Hotel Le Fontanelle is a timeless sanctuary where history embraces modern luxury. With its enchanting 13th-century stone façade and breathtaking panoramic views of lush vineyards and serene woodlands, this upscale retreat offers couples and romantic travelers an idyllic escape from the ordinary, all while being just a stone's throw from Siena's vibrant culture.

Total Relaxation - Unwind in the tranquil oasis of our wellness area, where the gentle sound of bubbling water mingles with the soothing aroma of essential oils. The indoor pool invites you to bask in hydromassage bliss, while the sauna envelops you in warmth, ensuring every moment spent here is one of pure indulgence.

Outstanding Location - Set against a backdrop of breathtaking landscapes, each room offers captivating views that change with the light—from golden sunrises to the deep hues of twilight. Explore the picturesque countryside on complimentary bicycles, where the scent of fresh herbs and blooming flowers fills the air, leading you to hidden gems of Tuscany.

Romantic Break - Dine under the stars at La Colonna restaurant, where every dish is a symphony of local flavors with a creative twist. Imagine savoring a delectable meal on the panoramic terrace as the sun sets, painting the sky in shades of orange and pink—a perfect setting for unforgettable moments together.

Guest Experiences - One guest shared how their evening was transformed by the attentive staff, especially Carlo, who anticipated their needs with remarkable care; when a forgotten cardigan left them chilly, he swiftly provided a soft scarf, ensuring their romantic dinner remained seamless and warm amidst the tranquility of the hills.

Nestled amidst the rolling hills of Tuscany, Villa Lecchi Hotel Wellness is a sanctuary where romance and relaxation blend seamlessly. The air is fragrant with the scent of blooming jasmine and freshly prepared Italian cuisine, inviting couples and solitude seekers to unwind in an oasis of beauty and tranquility. With panoramic views that stretch across olive groves and vineyards, this elegant retreat promises an unforgettable escape into the heart of Tuscany's lush landscape.

Romantic Getaway - Each moment at Villa Lecchi whispers romance, from intimate dinners on the terrace overlooking Chianti’s stunning hills to lazy afternoons spent lounging by the sun-kissed pool, where laughter dances on the breeze.

Spa Retreat - Indulge in total relaxation at our wellness center, featuring a heated hydromassage pool that cradles you in soothing warmth, allowing you to melt away your cares while the tranquil sounds of nature play in the background.

Culinary Delights - Savor exquisite meals crafted from local ingredients at our acclaimed restaurant, where the aroma of freshly baked pastries wafts through the air during breakfast, and evenings invite you to sip carefully selected wines under a starlit sky.

Guest Experiences - Imagine waking up to the gentle chirping of birds and the golden sunlight streaming through your window as you step onto your private terrace, mesmerized by the breathtaking views of San Gimignano’s iconic skyline—moments like these linger long after you leave.

Nestled amidst the rolling hills of Tuscany, Castello di Spaltenna Exclusive Resort & Spa is a treasured sanctuary where time feels delightfully suspended. This ancient 10th-century monastery envelops you in luxury and romance, offering an intimate escape filled with enchanting views and indulgent comforts that whisper sweet tranquility into your soul.

Romantic Retreat - Bask in the glow of candlelit dinners in the courtyard, serenaded by the gentle rustle of leaves and soft Tuscan breezes, while savoring exquisite local wines that elevate your dining experience to pure bliss.

Wellness Oasis - Immerse yourself in total relaxation at the spa, where the calming scents of essential oils mingle with the soothing sound of tranquil waters, inviting you to unwind in steam rooms, ice showers, and the blissful jacuzzi overlooking the picturesque countryside.

Gourmet Delights - Every morning, the breakfast terrace transforms into a vibrant tapestry of fresh fruits, artisanal breads, and robust cappuccinos, creating a sensory feast that awakens both the palate and the spirit as you gaze over vineyards kissed by the golden sun.

Guest Experiences - Imagine starting your day with the aroma of freshly baked pastries wafting through the air, as you sink into a plush chair on the terrace, enjoying the sight of emerald hills unfolding before you—a moment punctuated by laughter and joy from families splashing in the infinity pool nearby.

Nestled within the enchanting medieval heart of Radda in Chianti, Palazzo Leopoldo Dimora Storica & Spa is a luxurious sanctuary where history and elegance intertwine. This former patrician villa, dating back to 1310, invites discerning travelers to soak in the authentic essence of Tuscany, surrounded by rolling vineyards and breathtaking landscapes. Every corner whispers romance, making it a perfect retreat for couples and seekers of tranquility alike.

Historic Charm - Step into a world where ancient architecture meets modern luxury; each room is adorned with unique frescoes and original fireplaces that evoke tales of yesteryears. The air is imbued with the scent of aged wood and fine linens, creating an ambiance that feels both timeless and intimate.

Wellness Retreat - Indulge in pure relaxation at the hotel’s wellness area, featuring a serene indoor pool with hydromassage jets and two outdoor hot tubs nestled under the stars. Enjoy blissful spa treatments or unwind on the sun terrace, enveloped by the soothing sounds of nature—a true escape for the soul.

Culinary Delights - Savor the rich flavors of Tuscany at La Perla Del Palazzo, where local dishes are crafted with passion and served amidst the lush gardens. Sipping wine on the sun-drenched terrace while admiring sweeping views of the Chianti hills is an experience that lingers long after the meal has ended.

Guest Experiences - One guest recounted how a staff member's warm smile greeted them each morning as they savored the aroma of fresh pastries wafting from the kitchen, while another cherished evenings spent in their spacious suite, enjoying a glass of wine on their private terrace, the quiet village streets below illuminated by soft lantern light.

Nestled in the heart of Radda in Chianti, Hotel Palazzo San Niccolò & Spa is a sanctuary where elegance intertwines with historic charm. The flicker of candlelight dances across original frescoes as guests wander through antique-laden halls, creating an alluring atmosphere that beckons both romance and relaxation amidst the rolling Tuscan hills.

Romantic Escape - With enchanting views of verdant vineyards, this hotel offers intimate corners perfect for whispering sweet nothings, whether on the garden patio or while savoring exquisite local wines by the fireplace.

Spa Retreat - Indulge in tranquility at the hotel's spa, where the soothing sounds of gentle music complement the aromatic scents of essential oils, inviting you to unwind and rejuvenate after a day of exploration.

Historic Charm - The property exudes character with its beautifully preserved architecture, allowing guests to step into a living piece of history while enjoying modern conveniences like hydro-massage showers that offer a blissful touch of luxury.

Guest Experiences - Picture this: the aroma of freshly baked pastries wafts through the air each morning as attentive staff prepare delightful breakfast bags for those with early departures, ensuring no moment is overlooked during your stay.

Nestled in the heart of Tuscany, Castel Monastero whispers tales of its storied past from every stone and archway. This exquisite retreat, set within a meticulously restored medieval hamlet, offers an ambiance of timeless elegance, where rustic charm meets modern luxury, creating an intimate sanctuary for couples and adventurers alike.

Total Relaxation - Indulge in the serene embrace of the sprawling 10,700 ft² spa, where the soothing scent of herbal teas mingles with the soft sounds of nature. Choose from an array of rejuvenating massages and therapies designed to awaken the senses and restore harmony.

Outstanding Location - With panoramic views of rolling hills adorned with vineyards and olive groves, guests are treated to a stunning tapestry of colors that shift with the light. Just a short drive away, the enchanting streets of Siena await exploration, offering rich cultural experiences steeped in history.

5* Luxury - Every corner of Castel Monastero reflects opulence, from the elegantly appointed rustic rooms featuring rich wood and stone decor to the gourmet dining experiences infused with Tuscan flavors. The attentive staff ensures that every detail is taken care of, crafting a stay that feels both exclusive and welcoming.

Guest Experiences - As you settle into your well-appointed room, the aroma of fresh-baked pastries wafts through the air each morning, inviting you to savor an exceptional breakfast served in a sun-drenched courtyard. Guests reminisce about the gentle rustling of leaves overhead and the laughter shared over fine wines in the bar square, creating memories that linger long after checking out.