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Holiday rentals in Reggello

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Top-rated holiday rentals in Reggello

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
A two-story house is nestled among olive trees, surrounded by lush green hills. The structure features a balcony offering views of the natural landscape. A wooden fence delineates the property, which is set in a serene environment with a vibrant grassy area in the foreground.
Flat
4.85 out of 5 average rating, 131 reviews

La casa del Grillo, on the Tuscan hill

The "Grillo" house is located in the beautiful Tuscan hills, close to restaurants, and "The Mall" outlet. You'll appreciate the landscapes, the cool summer, and nature. The house is suitable for couples, large families and furry friends. A 5-minute walk to the center of Reggello and a 25-minute drive to Florence. The house is close to wonderful panoramic views, restaurants, and the "The Mall" outlet. You'll love the quiet, the cool summer, and the nature. The house is perfect for families, couples, and pets. It is 25 minutes away from Florence

Guest favourite
A serene hillside property is surrounded by lush greenery and ornamental trees. The inviting swimming pool glistens in the sunlight, with stairs leading into the water. The structure features a rustic design, blending with the natural landscape, and offers access to outdoor lounging areas.
Farm stay
4.87 out of 5 average rating, 112 reviews

Relaxing Holiday near Florence

located in Tuscany, halfway between Florence and Arezzo, an area that is appreciated all over the world for its climate and the beauty of the hilly landscape, that enables visitors to spend a unique and Relaxing Holiday in the Countryside in Italy. Located 500m above sea level and next to the ancient woods of Vallombrosa, The house dominates the valley of the river Arno and the Chianti hills, with its famous Olive Trees and Vineyards. The price does not include the heating and the tax that must be paid on the spot.

Top guest favourite
A charming outdoor dining area features a round table set with delicate dishware and a pink tablecloth. Surrounding the table are intricately designed white chairs. A gazebo provides shade, and lush greenery is visible in the background, creating a serene setting for leisurely meals.
Farm stay
4.99 out of 5 average rating, 502 reviews

Farmhouse Fattoria La Parita

Provencal-style apartment nestled between vineyards and olive trees. You will enjoy the tranquility of the countryside 10 km from the city and 4 km from the highway. The song of jays and cuckoos will be the soundtrack to the stay while the roe deer graze among the olive trees. A basic Italian breakfast is included (coffee, tea, milk, biscuits, etc.), but if you prefer a richer breakfast served at the table, the cost is €15 per person (€10 from 5 to 15 years, free under 5 years). EV wallbox available.

Top guest favourite
A stone structure with a tiled roof is framed by greenery, surrounded by rolling hills. A spacious outdoor area features a wooden table, inviting relaxation. Large trees and thriving shrubs enhance the tranquil setting, with a backdrop of a serene sunset illuminating the landscape.
Home
4.98 out of 5 average rating, 235 reviews

Sunset on Chianti Classico

Se cercate una location idilliaca nel cuore del Chianti classico, immersi nei vigneti e oliveti delle splendide colline toscane, nel podere di una Villa storica del ‘500, allora venite nel nostro fienile!! Ha una posizione dominante con una vista strepitosa, dove è possibile godersi tramonti mozzafiato. La totale indipendenza della casa, l'accogliente giardino, il grande loggiato permettono di trascorrere soggiorni in totale tranquillità. Le nostre recensioni sono la vostra migliore garanzia.

Top guest favourite
The rustic farmhouse is set against a clear blue sky, featuring a textured stone façade with wooden window shutters. A gravel courtyard is visible, adorned with potted plants and outdoor seating, offering a welcoming entrance to the tranquil countryside surroundings.
Farm stay
4.97 out of 5 average rating, 184 reviews

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.

Superhost
The image features a serene garden area with a sparkling pool surrounded by lush greenery. Comfortable lounge chairs are provided under shaded gazebos, while ancient olive trees add to the tranquility. The backdrop showcases sunlit hills and well-maintained landscaping, creating a peaceful retreat.
Home
4.74 out of 5 average rating, 65 reviews

-Il Fienile- Apartment in Reggello

Apartment in a portion of a villa, Podere Piazza di Sopra, in Reggello. The Fienile has two floors with a private entrance: a living room, two double bedrooms, one single bedroom, and one bathroom on the upper floor, and a full bathroom with shower in the ground-floor bedroom. The apartment has a private garden and a shared panoramic park with centuries-old olive trees, as well as a beautiful panoramic swimming pool shared with other guests. All this will make your stay magical.

Top guest favourite
The exterior of the castle is showcased at sunset, with vibrant orange and purple skies providing a dramatic backdrop. Stone towers rise from the landscape, surrounded by greenery and colorful flora, reflecting the historic charm of the property.
Castle
4.99 out of 5 average rating, 218 reviews

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.

Top guest favourite
Home
5 out of 5 average rating, 73 reviews

Relaxing Country Home in Tuscany with View

An incredible experience between flavor, nature and relax in the heart of Chianti. Situated between Barberino Tavarnelle, San Gimignano, Greve in Chianti, and Florence, Belvedere 27/A overlooks the Santa Maria Novella Castle, amidst olive groves and vineyards with an amazing view. A countryside Tuscan home, surrounded by olive’s fields and greenery, equipped with every comfort. Reconnect in this serene, one-of-a-kind stay, for a relaxing and peaceful holiday.

Top guest favourite
A charming stone building surrounded by lush greenery features a wooden terrace with a parasol and flower pots. Two loungers are placed on the well-maintained lawn, providing a relaxing outdoor space.
Farm stay
4.99 out of 5 average rating, 471 reviews

Old hayloft on the Chianti hills

Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, overlooking the Chianti valleys and enjoying splendid views of the surrounding hills and the city of Florence. The apartment is completely independent, on two internally connected floors, and features a private garden lined with centuries-old oaks and Tuscan cypresses. The restoration maintained the original Tuscan architectural style of rural barns.

Superhost
A private swimming pool is framed by a lush garden, featuring several lounge chairs and shaded areas provided by umbrellas. The pool area, lined with tile, is surrounded by greenery, including olive trees, creating a serene outdoor retreat.
Apartment
4.89 out of 5 average rating, 64 reviews

3 bedroom apt in Tuscan farmhouse w/ private pool

Welcome to Podere Piagge Reggello, a peaceful retreat in Tuscany’s “olive oil town.” Our house sits in the countryside, surrounded by olive trees, vineyards, woods, and cliffs. Enjoy your private 10×6 m pool (June–mid-Sept), a spacious park, and a private game room with ping pong, pool, and foosball. We live on the ground floor with a separate entrance and garden—nearby if you need us, but your space and pool are fully private for your stay.

Top guest favourite
The historic tower-penthouse villa is surrounded by lush greenery and trees. The three-story structure is characterized by its earthy facade and wooden shutters. Well-maintained gardens with various plants create a serene outdoor environment, enhancing the villa's tranquil charm and historical significance.
Castle
4.96 out of 5 average rating, 133 reviews

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, character, convenience. 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.

Guest favourite
Holiday home
4.89 out of 5 average rating, 202 reviews

Barrel Suite Tuscany • Hot Tub • Vineyard View

Sleep inside a wine barrel in Tuscany — one of the largest in the world (3.5 m × 8 m) — nestled in an olive grove in Reggello, with panoramic views over the hills and vineyard. Private bathroom, kitchenette, veranda, private courtyard and exclusive hot tub: everything for a total escape from the world. 40 min from Florence, with Siena, Arezzo, The Mall Luxury Outlet and Vallombrosa all within easy reach. Free private parking included.

Popular amenities for Reggello holiday rentals