Villa vacation rentals in Castiglion Fiorentino

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Top-rated villa rentals in Castiglion Fiorentino

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Top guest favorite

The exterior of the villa showcases a rustic stone facade under a clear blue sky. A swimming pool is visible in the foreground, with white lounge chairs positioned nearby. A covered patio area features a dining set, providing a welcoming space for outdoor relaxation.

Villa in Poppi

5 out of 5 average rating, 13 reviews

Villa Lux Poggelleri with a unique view of the Casentino

The unique 360-degree view of the entire Casentino valley characterizes Villa Lux, which thanks to its dominant position enjoys an unforgettable panorama. Immersed in the greenery of a 3-hectare private property, it guarantees relaxation and tranquility. Recently renovated with quality materials. Villa Lux is a great starting point for visiting the Casentino with its hermitages, castles and unspoiled nature, just a stone's throw from the art cities of Tuscany: Florence, Arezzo, Cortona, Siena, Pisa.

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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

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Villa in Siena

4.81 out of 5 average rating, 268 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.

Guest favorite

The villa is surrounded by lush greenery, showcasing an inviting infinity pool that reflects the sky. The stone exterior of the house features warm wooden shutters, with outdoor seating visible on the terrace. Nearby, lavender plants create a serene ambiance against the landscape.

Villa in Lisciano Niccone

4.85 out of 5 average rating, 41 reviews

Villa San Martino, on the Tuscany/ Umbria border

Villa San Martino is not just another holiday in Tuscany or Umbria - this is a really special place. With spectacular views across the world famous Niccone Valley towards Mercatale di Cortona, relax in the infinity pool, or dine alfresco on the terrace. From the villa you can easily access the enchanting towns of Cortona, Pienza, Montepulciano, Siena, Perugia, Assisi and Florence. The Niccone valley is home to delightful restaurants and you can sample great local Tuscan & Umbrian cuisine.

Top guest favorite

A serene backyard features a private grey stone swimming pool surrounded by lush greenery. There are several lounge chairs positioned nearby for relaxation, with a simple side table completing the outdoor setting. The villa is visible in the background among the trees.

Villa in Cortona

5 out of 5 average rating, 10 reviews

Villa Leopoldina, 6 pax, Private Pool

Magnifica nuovissima villa, tra Cortona e Montepulciano e a pochi minuti dal Lago Trasimeno. L’abitazione dispone di 3 camere da letto, ognuna con bagno privato, wi-fi, cucina perfettamente attrezzata e parcheggio privato. L'idilliaco giardino di 2000 mq, comprende querce, faggi, pini marittimi e una bellissima piscina privata in pietra grigia. Circondato da campi di girasole, vigneti e da boschi di querce e castagni, garantisce un assoluto relax e la massima privacy. Ideale per 6 persone.

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.

Superhost

The rustic villa is surrounded by lush greenery, offering a serene landscape. Its terracotta roof complements the natural setting, while pathways are lined with shrubs and trees. An inviting courtyard can be seen, creating a peaceful entrance to the home.

Villa in Castelnuovo Berardenga

4.89 out of 5 average rating, 9 reviews

Elegant Chianti Villa w/ Stunning Views + Starlink

Villa Adagio, in the compound of Casale Fornaci, is a magnificent country house inside the beautiful Tenuta of Arceno in the Chianti Classico. Surrounded by a grove of olive trees atop lush green hillsides, this 13th-century restoration with its terracotta floors, wood-beamed ceilings, and stone walls is the perfect vacation villa for families and friends wanting to enjoy Tuscan life at its finest. Enjoy memorable day trips to Florence, Siena, wineries & more.

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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.

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.

Superhost

A spacious living area is highlighted by exposed wooden beams and terracotta flooring. Natural light floods through large windows, adorned with soft curtains. An ornate wooden cabinet and decorative plants enhance the cozy feel, while a colorful rug adds warmth to the inviting atmosphere.

Villa in Asciano

5 out of 5 average rating, 4 reviews

Villa Le Liscaie [Sienese Crete]

Private Villa in the Crete Senesi - Stunning swimming pool surrounded by olive grow - 4 bedrooms: one master bedroom, one room with two single beds, one with a single bed and another room with a comfortable double sofa bed - large outdoor space and private forest - 5 minutes from the highway

Guest favorite

The historic villa displays a vibrant yellow façade, flanked by lush greenery and cypress trees. An inviting infinity pool is visible in front, surrounded by a stone patio. A shaded seating area offers a relaxing retreat near the steps leading to the entrance.

Villa in Greve in Chianti

4.92 out of 5 average rating, 25 reviews

Luxury villa in Tuscany Panzano in Chianti

Luxury villa surrounded by vineyards in walking distance from Panzano in Chianti. Infinity pool, pizza oven, pétanque area, outdoor fitness and breathtaking views over the rolling hills of Tuscany. The villa also has its own winery and produces both red and sparkling wine of high quality.