
Villa vacation rentals in Arezzo
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Top-rated villa rentals in Arezzo
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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
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.
4.99 out of 5 average rating, 131 reviews
Casa Napoleone - Tuscan Villa w/ pool near Cortona
A villa set on a hill, overlooking a magnificent Tuscan valley, yet only 10 mins drive from Castiglion Fiorentino train station. A 20 min drive from Arezzo and Cortona, a town made famous by the book and movie “Under The Tuscan Sun”. The Villa is the perfect base and within striking distance of Florence, Siena, Assisi and Montepulciano, famous for its Brunello wine, either by car or train. And after all that exploration you’ll return to soak in the pool whilst enjoying the stunning views.
4.96 out of 5 average rating, 28 reviews
Tuscany Villa Mammi
Large renovated stone villa in the woods of Castiglion Fiorentino, near Cortona, Arezzo, and Siena. A haven of privacy with a swimming pool, a panoramic hot tub with breathtaking views of the valley, and ping pong. Enjoy magical evenings under the stars thanks to the authentic stone barbecue and wood-fired pizza oven. The ideal retreat for those seeking relaxation, nature, and comfort in the heart of Tuscany, perfect for families or groups dreaming of a truly unforgettable vacation.
4.99 out of 5 average rating, 90 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.
4.96 out of 5 average rating, 102 reviews
Tuscany Country House with swimming pool
Casa di Sasso is a holiday home surrounded by greenery, just 10 minutes drive from the town center of Arezzo. The villa, recently renovated in a cozy, bright and elegant country style, is divided into 3 apartments that can be communicating and can accomodate up to 16 people. All rooms are equipped with air conditioning and free wi-fi. Outside you will find a panoramic terrace, gazebos, relaxing areas and a beautiful seasonal swimming pool with hydromassage.
4.95 out of 5 average rating, 75 reviews
Villa Montanina - relax in esclusiva in Toscana
A typical Tuscan villa exclusively immersed in the views, greenery and peace of the Casentino Valley where you can spend moments of relax, fun and experiences where nature, culture and taste come together. During your stay you can enjoy cooking classes, yoga classes, wine tastings, massages, personalized experiences and relax in the large swimming pool. The Villa with its many large green spaces is also perfect for celebrating your dream wedding in Tuscany.
4.99 out of 5 average rating, 85 reviews
Ortaglia di Sotto Farm
Located in the Tuscan countryside, a 10-minute drive from Castiglion Fiorentino, Podere Ortaglia di Sotto offers a private pool with enclosed garden, WiFi and free private parking. The holiday home features 5 bedrooms, 6 bathrooms, a flat-screen TV, a dining area, a fully equipped kitchen and a terrace with mountain and valley views.(The pool is available from the last week of May to the second week of October .The dates may vary depending on the weather.)
4.95 out of 5 average rating, 19 reviews
Tuscany View - Villa Arianna
This beautiful villa, which can accommodate up to ten (10) people, will provide an unparalleled Tuscan experience. While positioned perfectly to allow easy access to the most beautiful towns and villages of southern/central Tuscany (such as Arezzo, Florence, Siena, Cortona, Montepulciano) and northern Umbria (such as Perugia, Orvieto, Assisi); you’ll find this villa offers complete privacy as well as a sense of peace and tranquility to all who visit.
4.99 out of 5 average rating, 123 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.
4.89 out of 5 average rating, 309 reviews
Villa Poggio a Mandria in Chianti
Villa Poggio a Mandria is the gateway to the Chianti; it is a good base to reach the most beautiful art cities of Tuscany (Arezzo, Florence, Siena, San Gimignano, Volterra) in about one hour time. On the surrounding hills there are medieval villages, which offer visitors a charming atmosphere of the past and the opportunity to take walks in an unspoiled countryside.
4.99 out of 5 average rating, 162 reviews
Villa il Laghetto with Infinity Pool in Tuscany
PERFECT LOCATION FOR YOUR WEDDING, SPECIAL EVENTS & PRIVATE PARTY! PAY ATTENTION: You can book Food&Wine services such as Chef in Villa, Cooking Class and delivery shopping. The ideal location to spend days in the tranquillity of a natural oasis with breathtaking views. It's divided in a main building and a dependance, it offers pool and Jacuzzi (not hot)
4.96 out of 5 average rating, 56 reviewsPopular amenities for Arezzo villa rentals
Private villa rentals

Beautiful and cozy country-house, sleeps 11
5.0 out of 5 average rating, 25 reviews
Tuscan Villa with Private Jacuzzi & River
5.0 out of 5 average rating, 51 reviews
VILLA LAMA - A window overlooking the river
4.96 out of 5 average rating, 78 reviews
At Elena's
4.67 out of 5 average rating, 18 reviews
Villa La Foce
4.95 out of 5 average rating, 21 reviews
Sestuccia
4.99 out of 5 average rating, 75 reviews
Villa Bruna, entire house in Chitignano
4.94 out of 5 average rating, 80 reviews
Casanova di Bricciano
5.0 out of 5 average rating, 25 reviewsLuxury villa rentals

Tuscan Villa Luigina with Pool & Panoramic View
4.8 out of 5 average rating, 110 reviews
Villa San Martino, on the Tuscany/ Umbria border
4.9 out of 5 average rating, 59 reviews
Villa Le Vigne, 8 pax, private pool, Top Comfort
4.91 out of 5 average rating, 91 reviews
Villa Pergo is an ancient charming country villa
5.0 out of 5 average rating, 65 reviews
Villa marielena chianti farmhouse with hot tub - v
5.0 out of 5 average rating, 10 reviews
Podere on the Crete Senesi
4.96 out of 5 average rating, 92 reviews
Lucignano Secondo – La Villa
4.89 out of 5 average rating, 35 reviews
Il Posto Umbria - full property with large pool
5.0 out of 5 average rating, 9 reviewsVilla rentals with a pool

Podere il Trebbio
4.92 out of 5 average rating, 88 reviews
Villa Eleonora
4.85 out of 5 average rating, 20 reviews
Poggelleri the postcard on Poppi and Tuscan hills
5.0 out of 5 average rating, 5 reviews
Villa Nicole by Anita Villas
4.8 out of 5 average rating, 5 reviews
Villa La Pieve
4.67 out of 5 average rating, 36 reviews
Villa Aurora
4.97 out of 5 average rating, 67 reviews
Villa il Balocco
4.98 out of 5 average rating, 43 reviews
Il Fienile del Fossatino (The Fossatino Barn)
4.92 out of 5 average rating, 36 reviewsDestinations to explore
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- 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
- Mount Amiata
- Stadio Artemio Franchi
- Medici Chapel
- Basilica of Santa Croce
- Things to do Arezzo
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- Things to do Italy
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- Wildlife Italy
- Landmarks Italy
- Museums Italy
- Performances Italy
- Art workshops Italy
- Dining Italy
- Galleries Italy
- Outdoors Italy
- Architecture Italy
- Water sports Italy





