Vacation rentals in Pelago

Relaxation and charm in the Chianti hills

Beautiful stone farmhouse, detached, surrounded by olive trees and the Chianti hills, with private garden and panoramic swimming pool. Ground floor with large living rooms, antique fireplace and wood-burning oven, bright living room and fully equipped kitchen. On the first floor, three suites consisting of a bedroom, study and private bathroom. Access via gate and white road on private property just 500 meters from the village of Strada in Chianti. Ideal for peace and relaxation. Convenient location for visiting Tuscany.

Florence Sunset Hills • Giogoli

Escape to the peaceful hills of Giogoli where authentic Tuscan charm meets breathtaking views of Florence.Just 15 minutes from the city center and the Chianti countryside, this elegant home is the perfect base for exploring Tuscany while enjoying quiet mornings, unforgettable sunsets, and the beauty of the surrounding landscape. Surrounded by nature but close to the region's most iconic spots, it's the ideal retreat for anyone looking for comfort, tranquility, and a genuinely Tuscan experience

Bellavista Tuscany 1- pool and garden

🏡Well-furnished apartment near Florence, surrounded by olive groves 🪔 and Tuscan vineyards 🍷. From your terrace and garden 🌱, you can admire the beautiful historic village of Pelago and the Tuscan countryside 🌻. In the house, you will find everything you need to cook, etc., and Guendalina is ready to welcome you with advice and suggestions to make your stay unforgettable✨️. From April 2026, a private swimming pool shared with Bellavista Tuscany 2 will be available during the summer months.

Tuscan house private heated pool

Podere Benedettino of 1700, recently renovated in full respect of its history, located on the slopes of the natural reserve of Vallombrosa, immersed in the woods, just 29 km from Florence. The portion of farmhouse dedicated to rent has about 110 square meters of property with three bedrooms, kitchen, hall, entrance hall and two bathrooms. Podere Gualpoli is the place to rediscover your peace and relax immersed in a unique setting, where you can enjoy a charming private garden with infinitypool

Tuscan Country house with panoramic pool

Old stone Country House located on the top of an uncontaminated hill in a secluded atmosphere, with stunning 360° panoramas over the hills and the Arno river. Surrounded by private olives grooves, the accommodation offers an ideal mix between peaceful relaxation and opportunities for outdoor activities. With easy access to Florence (18 km) and major arts sites of Tuscan region such as Siena, San Gimignano, Pisa, Lucca, the wine Chianti area and many others landscaping or trekking attractions.

Villa Carla – Florence View, Tennis & Hot Tub

Escape to a peaceful private Tuscan estate 20 minutes by car from Piazza del Duomo, in the heart of Florence. Villa Carla offers countryside tranquillity with panoramic views over the city. The property includes a main villa and a separate dependance, providing privacy and comfort for families and groups. Relax in the spa pool, play tennis, or dine under the gazebo as Florence lights up at sunset. A quiet retreat in nature, ideal for guests seeking privacy and space close to the city centre.

Stone farmhouse, exclusive private pool

Podere Montebono is located in the hills of Reggello just 30 km from Florence. Ideal for cities of art and naturalistic places. The farmhouse is isolated on a hill, surrounded by nature, surrounded by olive trees, garden and forest. The guest house is an independent wing of the large two-storey farmhouse: 3 bedrooms, a kitchen, a living room, and a bathroom. The private pool is exclusively for those who rent the house (max 4 people). We do not rent single rooms. BBQ area. Total privacy.

The Castle of Ferrano - Castle in Tuscany

Try the experience of staying in a real Castle! Il Castello di Ferrano offers to its hosts the chance of living an unforgettable experience: you will be the only guests in the castle, and everything will be for you (private pool from June to September, gardens etc..). Historical building, surrounded by nature, finely decorated, frescoes/moulding on the ceiling, ample terrace w/ stone and terracotta floor, private outdoor pool.. Good position. Preferably come by car.

Farmhouse in Chianti with Swimming Pool

Agriturismo Il Colle is located on one of the Chianti hills. The structure has been completely renovated, dominates the Chianti valleys and enjoys a splendid view of the surrounding hills and the city of Florence just 35 minutes by car The apartment is located on the ground floor of the main farmhouse, with independent access and private space. The care taken in the restoration and furnishing make the house particularly welcoming, respecting the rural style.

Tower Penthouse in small castle near Florence

900 year old Tower-Penthouse apartment in Chianti Villa, spacious & super-scenic historical home that combines magical atmosphere with space, light, history, convenience. (AC throughout). Painting-like 360° views of Tuscan Hills all the way to Florence; sun-filled, private grounds. Perfect location for an unforgettable family stay. Ample private property (including forest). Walking distance from village shops. Convenient location, Florence in sight.

Barn

Located in Fontisterni, a small village in Pelago near Pontassieve, the Fienile holiday apartment offers a relaxing stay. The 50 m² property has a living room with sofa bed for 2, a fully equipped kitchen, 1 bedroom, and 2 bathrooms, accommodating up to 4 guests. The open-plan layout uses partial walls to provide some privacy. Amenities include fast Wi-Fi (suitable for video calls) with workspace, TV, washing machine, baby cot, and air conditioning.

Villa with swimming pool on the Florentine hills

180sqm villa on 3 floors, private pool, 40.000sqm land of olive trees "Poggio Secondo" is a private historic villa built in 1700 and entirely renovated in 2012 in full respect of its history, original design and materials. It is a short drive away from Florence (25Km distance), located on the hills of the Tuscan countryside. The villa comes with a private 40.000sqm olive tree garden and a state-of-the-art swimming pool to relax.