Villa vacation rentals in Gaiole in Chianti

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Top-rated villa rentals in Gaiole in Chianti

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Guest favorite

Villa

4.94 out of 5 average rating, 106 reviews

VillaCortevecchia PrivatePoolVineyard 15minFlorenc

Villa Cortevecchia (Superhost) is a 700 yr-old Tuscan Farm House renovated w/ western standards. Rustic & modern comfort! Top of a gorgeous, panoramic hill, pool, A/C, huge garden. Directly off Chianti Strada .5 min walk to Le Corti Winery. 17 min to Florence, Piazza Mich. Perfect Location! Stunning! *always “super hosts” in past but stopped renting for a few yrs so we lost that status but see all reviews! ❤️We replaced white sofas as they were 13 yrs old. added more furniture outside! Upgrades!

Guest favorite

Villa

5 out of 5 average rating, 13 reviews

Exclusive farmhouse, pool, en-suite A/C rooms

Tuscany Villa with privatepool,max 8 pax, SienaView. Siena only 8km driving; less than 5 minutes driving you have supermkt, pizzeria, bank, restaurants. 2 Floors only for you, about 250 sqm 4 bathrooms en suite, Airconditioning, Private pool and garden NO AREAS SHARED WITH OTHER GUESTS Inside an organic Farm, where you can see the real Farm work, to know Farmers and visit their Organic Pasta factory, to have Farm Experience on demand, purchase and taste our organic products ENJOY YOUR TUSCANY!

Superhost

Villa

4.8 out of 5 average rating, 264 reviews

XIII Century Tower with Private Panoramic Pool

Ancient country tower property with 5 airconditioned bedrooms for up to 12 guests at the heart of the peaceful Montechiaro organic wine estate. From your private pool, soak in the Tuscan sun and enjoy unforgettable views of the Chianti rolling hills and the medieval towers of Siena. The property also boasts access to the endless olive grove, a large patio area for outside dining in the shade, ping pong table for fun family matches, WIFI & free parking. Silence and time are the real luxury here.

Guest favorite

Villa

5 out of 5 average rating, 105 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.

Superhost

Villa

4.82 out of 5 average rating, 51 reviews

Florence & Tuscany. Pool, jacuzzi, parking & relax

Charming 15th century Tuscan Villa, 5bdr, restored respecting local traditions, fenced and furnished with international taste. A 360° view and exclusive comfort. Strategic position -in the heart of Tuscany- 10 minutes from Thermal Spa "Grotta Giusti" and from the motorway, to easily reach Florence, Lucca, Pisa, Siena, beaches & Cinque Terre. Surprising, 30 steps away: you can discover a restaurant of excellence, for unforgettable dinners. We are absolutely certain: it will not disappoint you!

Superhost

Villa

4.72 out of 5 average rating, 32 reviews

Private Villa: Panoramic Pools and Wellness

la Villa è immersa tra le vigne e gli olivi: Siamo nel cuore del chianti storico ma in posizione strategica per raggiungere Siena , Firenze e San Gimignano. Ideale per riunioni familiari, piccole cerimonie, pizza party nel forno a legna o rilassarsi nella spaziosa piscina con splendida vista.Sempre ad uso esclusivo degli ospiti una suggestiva Spa all'interno di una loggia panoramica, direttamente collegata con la casa, con bagno turco, sauna, Jacuzzi e sala massaggi.

Guest favorite

Villa

4.97 out of 5 average rating, 106 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.

Superhost

Villa

4.94 out of 5 average rating, 17 reviews

A Romantic Villa in the heart of Tuscany

The old country villa is the ideal location for an unforgettable vacation, suitable for families and small groups: where you can rest and enjoy the fresh and spacious interiors, the shade of the loggia and the scent of the aromatic herbs in the wide garden. Where you may work, read, write and relax in a peaceful atmosphere, visit the nearby artistic cities, take quiet walks or a gourmet tour through the many trattorias of the area.

Guest favorite

Villa

4.94 out of 5 average rating, 126 reviews

"Villa Daisy" overlooking Siena

Wonderful villa with independent entrance inside the "Caggiolo" estate, returned to light with careful and deep renovation that has kept the typical guidelines of a Tuscan farm intact. Beautiful panoramic view of Siena. Located in the Villas of Corsano, only 14 km from the city. Ideal place to spend days in total relaxation and enjoy the wonders that this area offers (Chianti, Val d 'Orcia, Crete Senesi...).

Superhost

Villa

4.91 out of 5 average rating, 23 reviews

Lovely villa heated outdoor pool & tennis court

A spectacularly located and comfortable holiday accomodation offers an inviting heated swimming pool (size 10x5x1,40 m deep), tennis court, Jacuzzi and gym a large furnished terrace overlooking the beautiful Casentino valley and its breathtaking views. The property can accomodate up to 12 guests and has 6 bedrooms each bedroom comprises its own bathroom.