Villa vacation rentals in Gaiole in Chianti

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Top-rated villa rentals in Gaiole in Chianti

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Superhost

Villa in Chianciano Terme

5 out of 5 average rating, 10 reviews

3bdr deLux Villa in Montepulciano Tuscany,Top View

Live your own true experience as a local at LaVittoria 10 in Val d'Orcia, short driving to Montepulciano, Pienza, Cortona,Siena Huge apt on top floor of the Villa, with 2 magnificent suites, panoramic lounge and professional kitchen, plus The Cottage,for 2+1 , with private entrance, kitchen, large bdr and bathroom with Jacuzzi for 2! Outdoor Hot tub with top view and relax area with comfy sofas !Your local host arranges private dinners and Wineries tour & tasting. E-bikes tour with guide. Wifi

Superhost

Villa in Siena

4.8 out of 5 average rating, 267 reviews

XIII Century Tower with Private Panoramic Pool

Ancient country tower property with 5 airconditioned bedrooms for up to 10 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.

Top guest favorite

An aerial view captures the expansive Poggio del Fattore estate, showcasing lush greenery and neatly arranged olive trees. The two main buildings, characterized by terracotta roofs, are complemented by the blue of the swimming pool, surrounded by vibrant gardens and cypress trees.

Villa in San Leolino

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

A serene outdoor pool is surrounded by landscaped gardens and trees, illuminated by soft lighting. Sun loungers and umbrellas provide shade, while a wooden railing enhances the scenic view of the surrounding Tuscan landscape under a twilight sky.

Villa in Monsummano Terme

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!

Top guest favorite

An aerial view showcases the Tuscan villa nestled within olive groves, with a private infinity pool reflecting the surrounding hills. The rustic architecture features terracotta roofs and a stone exterior, complemented by lush greenery and tranquil pathways leading to the entrance.

Villa in Cortona

5 out of 5 average rating, 71 reviews

Stunning Tuscan Villa & Panoramic Infinity Pool

Stunning Tuscan hilltop Villa, with infinity edge swimming pool, has sweeping 180° panoramic views to Cortona, Lake Trasimeno and the entire Val Di Chiana. The perfect family retreat within ancient sun-drenched olive groves. 5 Double bedrooms; 4 bathrooms; new fully integrated kitchen & dining living space; living room with fireplace; TV snug; stone BBQ & outdoor kitchen within dining terraces and gardens; covered breakfast porch; parking; private infinity pool with sunset views.

Superhost

A serene pool area features a clear blue swimming pool surrounded by lush greenery and blooming flowers. A natural stone waterfall adds a calming element, while nearby, vibrant plants line the edges, enhancing the peaceful outdoor setting.

Villa in Castelnuovo Berardenga

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.

Top guest favorite

Villa in San Casciano

4.97 out of 5 average rating, 108 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.

Top guest favorite

The villa, constructed from warm stone, is positioned amidst lush hills. It features a panoramic pool with sun loungers and umbrellas, surrounded by greenery. An outdoor pergola provides shaded seating, while ample parking is located nearby.

Villa in Radicondoli

5 out of 5 average rating, 8 reviews

Villa PoggiAlto, panoramic pool and spa in Tuscany

Villa PoggiAlto, recently renovated residence, with materials for incomparable luxury and comfort. It is located in the province of Siena, in a dominant position on the top of a hill. Its large panoramic swimming pool and wonderful spa will offer an unforgettable holiday in both summer and winter. Villa Poggialto is the ideal place for those who want to spend a holiday in Tuscany full of culture, nature, relaxation and good food with friends and family.

Superhost

A charming stone villa is framed by lush greenery and vibrant flower beds. The building features three arched windows with planters, a terracotta roof, and steps leading to the entrance. The expansive lawn offers a serene atmosphere, complemented by distant views of the rolling hills.

Villa in Radicondoli

4.94 out of 5 average rating, 18 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.

Superhost

An oversized saltwater pool is showcased, surrounded by a stone patio and eight lounge chairs. Lush green hills and vineyards stretch into the distance, with clear blue skies above. The area is accented by well-maintained gardens and natural vegetation, enhancing the scenic landscape.

Villa in Castiglione d'Orcia

5 out of 5 average rating, 10 reviews

#1 Luxe Farmhouse, Hilltop Views, Saltwater Pool

With outstanding 360 degree views of vibrant olive groves, cypress trees, and endless vineyards, this outstanding villa sits on top of the world. Surrounded by lush, rolling green hills, one of the most unique getaway experiences awaits. Equipped with a large saltwater pool and a modern interior with just the right amount of Tuscan flair, immerse yourself in the old country with a few added luxuries.

Superhost

A serene outdoor area features a private swimming pool surrounded by lush greenery. Two lounge chairs and a small table are positioned beside the water, offering a relaxing space. The villa stands in the background, framed by trees and garden foliage.

Villa in Montopoli

4.81 out of 5 average rating, 54 reviews

Villa Belvedere vista stupenda immersa nel verde

Il mio alloggio è vicino a arte e cultura, splendide viste panoramiche, attività per la famiglia, ristoranti e spiaggia. Ti piacerà il mio alloggio per questi motivi: l'atmosfera, gli spazi esterni e la luce. Il mio alloggio è adatto a coppie, avventurieri solitari, chi viaggia per lavoro, famiglie (con bambini) e amici pelosi (animali domestici).

Guest favorite

A well-maintained garden surrounds the entrance of the villa, featuring a variety of greenery and flowering plants. A paved pathway leads to the door, with a small seating area visible just beyond it. Solar panels are installed on the roof, emphasizing sustainability.

Villa in Figline e Incisa Valdarno

5 out of 5 average rating, 26 reviews

Villa Siveri - private swimming pool - air con

Affascinante e lussuosa villa con piscina privata. Grandissima villa con cucina, sala da pranzo, sala con caminetto, 2 camere matrimoniali, 1 camera singola , 1 camera con letto alla francese, 1 divano letto matrimoniale nel soggiorno al primo piano (tra le due camere), 2 bagni di cui uno con vasca idromassaggio e uno con doccia.