Villa Rental Tuscany Chianti Pool
Are you looking for the perfect villa in Tuscany with a pool? Imagine waking up surrounded by vineyards, olive groves, and hills dotted with cypress trees. The Chianti region, located between Florence and Siena, offers iconic landscapes and luxurious accommodations with private pools. Whether you are planning a family holiday, a group getaway, or a romantic stay, choosing a villa in Chianti with a private pool means combining relaxation, privacy, and authentic Tuscan charm like no other experience.
The Chianti landscape is not only beautiful—it’s iconic. Famous worldwide for its wine, Chianti also offers medieval villages, historic architecture, exceptional cuisine, and breathtaking views. Staying in a villa with a pool means maximum privacy surrounded by vineyards and olive groves, spectacular views of the Chianti hills, rustic elegance combined with luxury, and a strategic location close to Florence, Siena, San Gimignano, Certaldo, and numerous wineries. Refreshing yourself in the pool after a day of sightseeing or wine tasting is an unforgettable experience. The pool naturally becomes the focal point for sunset aperitifs and Tuscan evenings.
Castello di Montegufoni – Historic castle with panoramic pool
A former medieval castle renovated in the 1600s, Montegufoni is surrounded by olive groves and vineyards. Its outdoor swimming pool (12×6 m), open from April to October, is set among terraced Italian gardens with a ping pong area and green lawns. The estate includes apartments managed by the Posarelli family, a Tuscan cuisine restaurant, and services like cooking classes and guided tours. Ideal for those who love culture and wine. 👉 [See Castello di Montegufoni]
Villa Simone – Elegant 15th-century manor in Chianti
Villa Simone, a refined 15th-century residence, hosts up to 14 guests in seven bedrooms. It offers a large swimming pool, billiard room, gym, wellness area with sauna and Jacuzzi—all with views over the Chianti hills. Perfect for families or groups seeking comfort, history, and modern amenities. 👉 [See Villa Simone]
Villa Orchidea – Seventeenth-century elegance with pool and garden
Villa Orchidea combines historic architecture with modern and elegant interiors. Located in manicured gardens in the heart of Chianti, it offers a panoramic pool, barbecue area, and spaces for events or weddings up to 15 guests across the main villa and annex. A refined choice for those who want charm and comfort. 👉 [See Villa Orchidea]
Villa Maggiano – Privacy and spectacular views
Located in Lucardo, on the edge of Chianti, this stone villa offers a raised private pool with panoramic valley views. It can host up to 10 guests in five air-conditioned bedrooms. Guests appreciate the tranquility, privacy, and pool area—ideal for families seeking relaxation. 👉 [See Villa Maggiano]
La Ruota & Casa Lucia
Among Chianti villas, La Ruota and Casa Lucia feature private pools, typical Tuscan stone architecture, terraces, and peaceful gardens—ideal for couples or small groups looking for relaxation. 👉 [See La Ruota] – 👉 [See Casa Lucia]
All the villas have private panoramic pools, perfect for cooling off and relaxing. Outdoor spaces include sun terraces, barbecue areas, and well-kept gardens to fully enjoy the Tuscan outdoors. From the medieval Castello di Montegufoni to the 15th-century elegance of Villa Simone and the 17th-century charm of Villa Orchidea, these properties combine historic architecture with modern comforts: air conditioning, Wi-Fi, cozy bedrooms, and fully equipped kitchens.
All villas are located near Florence, Siena, San Gimignano, and Certaldo, making day trips easy. The central location allows visits to wineries, olive oil mills, and local markets, as well as participation in food and wine tours. Many properties offer private chefs, guided tours, cooking lessons, and concierge support via WhatsApp for a tailored stay.
The best time to visit Chianti is spring (April–June), with mild weather and fewer tourists, and autumn (September–October), when vineyards turn red and gold. Summer (July–August) is perfect for enjoying the pool, though busier. Pools are generally open from mid-April to late October.
We carefully select only luxury properties in Tuscany. Each villa is chosen for exceptional comfort and privacy, authentic character and unique design, privileged locations in Chianti, and personalized assistance to plan your stay. We help organize extra services and guarantee a hassle-free experience.
📲 Contact us now on WhatsApp to receive a personalized quote and discover the best villas available for your dates!
