
Villa holiday rentals in Reggello
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Top-rated villa rentals in Reggello
Guests agree: These villas are highly rated for location, cleanliness and more.

Manor House - IlVillinoFarmhouse
Entire upper floor of the newly renovated Manor House in traditional Tuscan style. High ceilings with exposed beams make the place cozy and perfect for families or groups of friends. In the house, there are two large functional fireplaces (in the living room and kitchen). Private, non-shared accommodation. The house has a large covered terrace, garden with sofas, BBQ, fire pit, private parking. The swimming pool among the olive trees and vineyards is ideal for relaxation and has private access to the shared area
FamilyLocationGetting around
4.93 out of 5 average rating, 256 reviews
Tuscan charm of villa - countryside - Villa Senaia
In the charming Tuscan countryside, among olive trees and vineyards, a stone villa, in a strategic position to grasp the secrets of Tuscany and Umbria air conditioning and swimming pool with wellness area for your relaxation and comfort Villa Senaia is a large house with wooden beams, in a beautiful hillside location with idyllic views overlooking one of the favorite places in the Tuscan countryside, an attractive setting for outdoor dining, drinking Tuscan wine and listening to crickets and cicadas
FamilyValueWi-Fi
4.9 out of 5 average rating, 241 reviews
Poggio del Fattore-Villa with pool, hilltop, Chianti
Poggio del Fattore is situated at the eastern edge of the Chianti region in Valdambra, a green valley that joins the lands of Florence, Siena and Arezzo. The farmstead is on the top of an hill and lies at the end of a long private road through a large olive growing estate; therefore you absolutely need a car. The breathtaking landscapes and the location of the villa offer the privacy needed for a peaceful and relaxing holiday and a perfect departure point from which to explore central Tuscany.
ValueFamilyLong stay
4.99 out of 5 average rating, 131 reviews
La Vignaccia (Farmhouse) - villa w/private pool
Nestled amidst the rolling hills of Tuscany, La Vignaccia beckons you to experience the true essence of Italian living. This enchanting villa, set within a sprawling estate, offers a haven of tranquility, where you can unwind and immerse yourself in the beauty of the Tuscan countryside. A secluded garden awaits, providing a serene setting for relaxation and alfresco dining. Take a refreshing dip in the sparkling pool, surrounded by breathtaking views of the Tuscan landscape.
LocationFamilyCleanliness
4.96 out of 5 average rating, 102 reviews
Tuscan Dream Villa @ Rustic Elegance Near Florence
🌿Welcome to Villa La Conigliera🌿, an ideal retreat for a romantic getaway or a relaxing stay, just a few kilometers from Florence. 🌟Set in the peaceful Tuscan countryside, overlooking an ancient courtyard, it blends rustic charm with modern comfort. Perfect for couples or families with a newborn, with a crib available upon request 👶. Two adjacent villas for 4 and 6 guests complete the hamlet. 🚗 A car/motorbike is recommended for exploring the beautiful surroundings.
FamilyLocationKitchen
4.94 out of 5 average rating, 150 reviews
Il Vichiaccio: Florence Villa with Jacuzzi
Cozy Chianti Villa close to Florence. This 135sqm stone house has a rustic kitchen with a fireplace. It sleeps 9 guests in 3 rooms, but for groups of 11, a 4th bedroom is included. Smaller groups can add it for extra comfort (extra fee). Enjoy the private garden with a covered dining area, a patio with armchairs and parking. The ground floor is fully wheelchair-friendly (kitchen, bedroom, bath). Plus, A/C and a private Jacuzzi (extra fee) for relaxing under the stars!
ValueLocationCheck-in
4.95 out of 5 average rating, 202 reviews
Podere Tignano, 4-bedroom villa in the Chianti!
Nestled among the rolling hills of Chianti between Florence and Siena, Podere Tignano offers breathtaking views over vineyards, olive groves, and golden grain fields. This charming Tuscan stone villa blends authentic rural character with modern comfort and welcomes up to 8 guests in 4 bedrooms. Surrounded by peaceful countryside and featuring a private swimming pool, it is the perfect retreat for those seeking relaxation, nature, and the true spirit of Tuscany.
ValueLocationCheckout
4.98 out of 5 average rating, 107 reviews
Luxury Villa in the very heart of Chianti
The views, the views, oh my word the VIEWS! Originating in the early 12th century this spectacular home once served as the bakery for the entire village. Now fully renovated, the entrance and ground level have been opened with glass arches allowing natural light to illuminate the exposed walls, 4 large bedrooms, 3 with ensuite baths ( including a jacuzzi ). Only Minutes away from the famous Wineries of Chianti, this is THE Spot for a glass amongst friends.
ValueLocationWalkability
4.98 out of 5 average rating, 120 reviews
The Tower
Ancient Tuscan villa, beautiful, with exclusive private garden, completely renovated, surrounded by the beautiful and gentle Tuscan hills. The villa has a breathtaking view, is very sunny, well furnished and equipped with all amenities, quiet and not isolated. The house is located in Bagnolo, a small hamlet of Impruneta at the gates of Chianti, an area of olive groves, vineyards and peace. The house is about 10 km by car from the center of Florence.
LocationValueWi-Fi
5.0 out of 5 average rating, 190 reviews
Villa Capanna, Private Pool, Breathtaking Views
Ancient restored barn with up to 6 bedrooms and 6 bathrooms, immersed in a historic wine estate, just 6 km from Siena. One of the most beautiful views that the Tuscan panorama can offer, airconditioned bedrooms, exclusive swimming pool, large triple garden, BBQ, poolside table, terrace to enjoy the sunset over the medieval towers on the horizon while sipping the organic wines of the estate, fireplace, parking free, WI-FI internet.
ValueLocationCondition
4.89 out of 5 average rating, 309 reviews
Villa Isabella
Villa Isabella is a comfortable Tuscan style villa located in the splendid Chianti hills in Tuscany with a large garden and a spectacular breathtaking panoramic swimming pool for exclusive use where you can experience the Tuscan tradition in full local style with the possibility of organizing private shuttles service for reach the property traditional experiences, services and tours only and exclusively for our guests.
LocationFamilyCheckout
4.96 out of 5 average rating, 209 reviews
Farmhouse on Florence hill
Two levels 800th rustic country house, on the hills surrounding the town with original forniture and a stunning view of the facing valley, a beautiful patio and large garden. 15 min driving from center, well placed for Chianti area, Siena, San Gimignano. 1hr driving to Pisa, Lucca, Volterra, Arezzo, Cortona and much more! Possible to have cooking class or dinners with my personal chefs Mirella and Stefano!
LocationValueBreakfast
4.98 out of 5 average rating, 147 reviewsPopular amenities for Reggello villa rentals
Private villa rentals

Put down your luggage, this is just the beggining!
ValueFamilySleep quality
4.89 out of 5 average rating, 99 reviews
Villa La Doccia, Greve in Chianti
LocationValueBiking
4.85 out of 5 average rating, 180 reviews
Farmhouse in Chianti
LocationValueBackyard
4.95 out of 5 average rating, 221 reviews
"Villa Daisy" overlooking Siena
ValueFamilyEV charging
4.95 out of 5 average rating, 174 reviews
In the Heart of Tuscany near Florence
FamilyLocationBackyard
4.97 out of 5 average rating, 559 reviews
Church of the Vaioni
LocationValueIndoor spaces
4.98 out of 5 average rating, 87 reviews
Tuscan Villa with Private Jacuzzi & River
ValueFamilyOutdoor spaces
5.0 out of 5 average rating, 53 reviews
[Villa Poggio ai Sassi] Private Villa & Pool
LocationFamilyCondition
5.0 out of 5 average rating, 16 reviewsLuxury villa rentals

Villa of the 2 Olive Trees (Abbadia Isola)
LocationValueCondition
4.97 out of 5 average rating, 174 reviews
THE CASTELLACCIO CYPRESSES (Cip 1 + Cip 2)
FamilyLocationIndoor spaces
5.0 out of 5 average rating, 17 reviews
L'Apparita del Peruzzi | Villa | Private pool & air conditioning
LocationFamilyLayout
5.0 out of 5 average rating, 22 reviews
Villa Holm stunning view 10 mn walk to city centre
LocationFamilyOutdoor spaces
5.0 out of 5 average rating, 56 reviews
Villa with pool in Chianti Area
ValueFamilyPool
4.95 out of 5 average rating, 73 reviews
Stunning Tuscan Villa & Panoramic Infinity Pool
ValueLocationBiking
5.0 out of 5 average rating, 96 reviews
Villa with swimming pool on the Florentine hills
FamilyValueHeating
4.97 out of 5 average rating, 30 reviews
Sestuccia
LocationFamilySleep quality
4.99 out of 5 average rating, 75 reviewsVilla rentals with a pool

Mathis House Best View in Chianti, Exclusive Pool
FamilyLocationWalkability
5.0 out of 5 average rating, 37 reviews
Romantic accomodation within Tuscan hills
LocationFamilyView
4.81 out of 5 average rating, 21 reviews
Coaching House
FamilyLocationAir conditioning
5.0 out of 5 average rating, 67 reviews
Fossatino Barn
LocationFamilyKitchen
4.92 out of 5 average rating, 36 reviews
VILLA with Pool - 2 Bedrooms
LocationValueIndoor spaces
4.92 out of 5 average rating, 89 reviews
Villa in Tuscany with a private panoramic pool
FamilyLocationAmenities
5.0 out of 5 average rating, 35 reviews
Chianti Tuscany: villa with a view
FamilyLocationCondition
4.93 out of 5 average rating, 81 reviews
Casa Faraona, villa with private pool
FamilyLocationLaundry
5.0 out of 5 average rating, 32 reviewsDestinations to explore
- Lake Trasimeno
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Stazione Santa Maria Novella
- Mugello Circuit
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Mercato Centrale
- Fortezza da Basso
- Uffizi Gallery
- Piazza della Repubblica
- Parco delle Cascine
- Piazzale Michelangelo
- Palazzo Vecchio
- Del Chianti
- Piazza della Signoria
- Pitti Palace
- Boboli's Garden
- Autodromo Enzo e Dino Ferrari
- Stadio Artemio Franchi
- Medici Chapel
- Basilica of Santa Croce





