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Villa holiday rentals in Arezzo

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Top-rated villa rentals in Arezzo

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Guest favourite
A stone villa surrounded by greenery is featured under a clear blue sky. A large swimming pool reflects the sunlight, complemented by sun loungers and colorful potted flowers along the edges. The outdoor area is perfect for relaxation with scenic views of the Tuscan hills.
Villa in Castiglion Fiorentino

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, 240 reviews
Top Guest favourite
A private pool area is surrounded by lush greenery and offers stunning views of the landscape below. Several sun loungers are positioned on the pool deck, with large umbrellas providing shade. The serene ambiance invites relaxation amid nature.
Villa in Castiglion Fiorentino

Tuscany Villa Mammi

Large, renovated stone villa in the woods of Castiglion Fiorentino, close to Cortona, Arezzo and Siena. A haven of privacy featuring a swimming pool, a panoramic hot tub with breathtaking views of the valley, and table tennis. Enjoy magical evenings under the stars, thanks to the authentic stone barbecue and the wood-fired pizza oven. The ideal getaway for those seeking relaxation, nature and comfort in the heart of Tuscany, perfect for families or groups dreaming of a truly unforgettable holiday.

4.99 out of 5 average rating, 89 reviews
Top Guest favourite
Villa in Arezzo

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, 27 reviews
Top Guest favourite
Villa in Cortona

Tuscan Villa Luigina with Pool & Panoramic View

If you want to live in a postcard .... Villa Luigina is the ideal place, all the rooms have a panoramic view, a dining room with a view ... a breakfast room with a view, or you can eat outside in the garden in front of the house and enjoy the spectacular view of the old town!! In the fascinating Tuscan hills, among olive trees and vineyards, a stone villa in perfect harmony with the environment in a strategic position to discover the secrets of Tuscany and Umbria. CIN:IT051012C2129WHTZX

4.81 out of 5 average rating, 108 reviews
Top Guest favourite
An infinity pool is framed by stone decking and wooden lounge chairs, inviting relaxation. Umbrellas provide shade, while terraced gardens with olive trees rise in the background. The surrounding landscape features gently rolling hills and clear blue skies, enhancing the serene outdoor setting.
Villa in Cortona

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.

5.0 out of 5 average rating, 96 reviews
Top Guest favourite
The exterior of a charming villa is surrounded by lush greenery, with vines climbing along the walls. A gravel pathway leads to the entrance, framed by well-kept gardens. Sunlight filters through the trees, creating a peaceful atmosphere ideal for relaxation and outdoor gatherings.
Villa in Pergine Valdarno

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, 101 reviews
Top Guest favourite
The pool is illuminated with soft lighting, creating a calming ambiance during the evening. Surrounding greenery provides privacy, and seating areas are visible. The smooth water surface reflects the gentle glow, inviting relaxation in a serene outdoor setting.
Villa in Monte San Savino

Villa Tonacato - Charming Villa with private pool

Ancient rural farmhouse, located on the Tuscan hills with views of the surrounding countryside. Isolated and ideal for those who want to relax but close to the main Italian tourist cities. Each room is equipped with air conditioners with windfree technology, in the living room there is an 82" ULTRA HD TV with SKY and international channels. The pool is equipped with Philips Hue lighting to create the right atmosphere at all times and a Bose Soundtouch bluetooth sound system

4.99 out of 5 average rating, 107 reviews
Guest favourite
The spacious kitchen and dining area features rustic wooden beams and well-lit windows that invite natural light. A large dining table is surrounded by white chairs, accommodating several guests. An inviting seating area with a sofa and decorative elements enhances the communal atmosphere.
Villa in Arezzo

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, 73 reviews
Top Guest favourite
The image features a serene outdoor area with a spacious swimming pool surrounded by lounge chairs. Lush greenery and flowering plants line the poolside, while a stone wall and distant hills provide a peaceful backdrop under a clear sky.
Villa in Pieve a Socana

Villa Montanina - exclusive relaxation in Tuscany

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, 83 reviews
Top Guest favourite
Villa in Arezzo

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, 122 reviews
Guest favourite
The traditional stone house is surrounded by a well-maintained lawn, showcasing a multi-level structure with a picturesque roofline. Large arched windows accentuate the façade, providing ample natural light. A clear blue sky serves as a backdrop, highlighting the tranquil rural setting.
Villa in Castiglion Fiorentino

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 swimming pool is available from 23 May to 17 October, closing and opening dates may vary depending on the weather)

4.95 out of 5 average rating, 19 reviews
Guest favourite
Villa in Siena

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, 307 reviews

Popular amenities for Arezzo villa rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Private villa rentals

Top Guest favourite
Villa in Castiglion Fiorentino

Beautiful and cozy country-house, sleeps 11

5.0 out of 5 average rating, 25 reviews
Top Guest favourite
Villa in Modine

Tuscan Villa with Private Jacuzzi & River

5.0 out of 5 average rating, 51 reviews
Superhost
The villa is surrounded by a lush garden, featuring manicured lawns and blooming plants. A terrace with outdoor seating is visible, along with a decorative umbrella. The two-story structure showcases a traditional roof and large windows, set against a backdrop of green foliage.
Villa in Laterina

Villa Mona Lisa

4.85 out of 5 average rating, 39 reviews
Top Guest favourite
A charming stone cottage is set among lush green hills, featuring large arched windows and a shaded patio area with outdoor seating. Olive trees surround the property, providing a connection to the natural landscape, while a gravel pathway leads to the entrance.
Villa in Sinalunga

The twigs

5.0 out of 5 average rating, 97 reviews
Top Guest favourite
An infinity pool sits on a green terrace, surrounded by lush greenery and olive groves. Several loungers are positioned on the lawn, offering views of the expansive valley and distant hills under a clear blue sky.
Villa in Loro Ciuffenna

The Lazy Oak

4.97 out of 5 average rating, 71 reviews
Superhost
The exterior view of a single-story villa features a private pool surrounded by a wooden deck and several lounge chairs. A shaded portico with seating overlooks a garden filled with greenery and flowers, providing a serene outdoor space.
Villa in Arezzo

At Elena's

4.65 out of 5 average rating, 17 reviews
Superhost
A saltwater swimming pool is framed by lush greenery, with sunbeds positioned on the grass nearby. A natural fence enhances the privacy of the outdoor area, which is surrounded by trees that provide shade and a serene environment.
Villa in Pierle

Historic Villa Getaway with 6BR/9BA, Pool, Views

4.89 out of 5 average rating, 46 reviews
Guest favourite
Villa in Poppi

Poggelleri the postcard on Poppi and Tuscan hills

5.0 out of 5 average rating, 5 reviews

Luxury villa rentals

Guest favourite
A serene pool area features a turquoise pool surrounded by well-maintained greenery. Sun loungers are positioned nearby, offering views of the lake and distant mountains. A terracotta pot adds a decorative touch against a backdrop of blue skies and lush nature.
Villa in Passignano sul Trasimeno

Villa Le Murate

4.94 out of 5 average rating, 16 reviews
Top Guest favourite
A serene pool area is framed by lush olive trees and a spacious lawn. Two lounge chairs are positioned by the edge of the inviting pool, with the house visible in the background, showcasing its traditional architecture and surrounding greenery.
Villa in Lucignano

Unique Villa in Tuscany

4.93 out of 5 average rating, 42 reviews
Superhost
A private swimming pool is nestled among lush greenery and manicured hedges, framed by lounging chairs and umbrellas. The villa's rustic facade can be seen in the background, surrounded by trees and shrubs. The atmosphere reflects a serene and inviting outdoor space for relaxation.
Villa in Pozzo della Chiana

Villa al Pozzo, five bedrooms villa in Tuscany

4.85 out of 5 average rating, 62 reviews
Top Guest favourite
Villa in Civitella in Val di Chiana

Casale La Querce-Tuscan Farmhouse with pool & view

5.0 out of 5 average rating, 23 reviews
Guest favourite
A rustic Tuscan farmhouse is surrounded by lush green vineyards, with a private pool visible in the grassy area. The structure features a mix of stone and terracotta, harmonizing with its natural landscape.
Villa in Cortona

Villa Le Vigne, 8 pax, private pool, Top Comfort

4.91 out of 5 average rating, 91 reviews
Top Guest favourite
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

Villa San Martino, on the Tuscany/ Umbria border

4.89 out of 5 average rating, 58 reviews
Guest favourite
The outdoor area showcases a spacious stone terrace adjacent to a private pool. A covered dining space is equipped with multiple chairs, and grassy lawns surround the property, offering a tranquil setting with views of the rolling Tuscan hills in the background.
Villa in Gaiole in Chianti

Riecine Capanna 4

5.0 out of 5 average rating, 9 reviews
Guest favourite
Villa in Gaiole in Chianti

Lucignano Secondo – La Villa

4.91 out of 5 average rating, 33 reviews

Villa rentals with a pool

Guest favourite
The crystal-clear swimming pool reflects the blue sky, bordered by a well-kept garden. In the background, a stone farmhouse features green shutters and a classic tiled roof. The pool area is complemented by shaded seating, offering a serene and private atmosphere.
Villa in Gaiole in Chianti

Podere il Trebbio

4.92 out of 5 average rating, 88 reviews
Superhost
A charming exterior of the villa is visible, showcasing a well-preserved façade that reflects its history as a former church. The building is surrounded by a lush garden featuring various greenery and colorful flowers under a clear blue sky.
Villa in Pergo

Villa La Pieve

4.67 out of 5 average rating, 36 reviews
Superhost
A serene view of a private pool, framed by lush greenery. The pool area is surrounded by neat hedges, and a wooden diving board extends over the water's edge, inviting relaxation in a tranquil setting.
Villa in Figline e Incisa Valdarno

Villa Rosa in Chianti with Pool and Jacuzzi

4.95 out of 5 average rating, 37 reviews
Guest favourite
An inviting infinity swimming pool is surrounded by a well-kept garden. Lounge chairs are positioned around the edge, allowing for relaxation under the clear blue sky. The villa is visible in the background, framed by lush greenery and trees.
Villa in Castiglion Fiorentino

Villa Degli Olivi

5.0 out of 5 average rating, 31 reviews
Guest favourite
A panoramic view of a lush garden features a rectangular swimming pool surrounded by tall green trees. The vibrant greenery of the landscape is visible, with blue skies punctuated by fluffy white clouds overhead, creating a serene outdoor atmosphere.
Villa in Rignano sull'Arno

VILLA with Pool - 2 Bedrooms

4.92 out of 5 average rating, 88 reviews
Top Guest favourite
A spacious outdoor area features a large swimming pool surrounded by a manicured lawn. Sun loungers and umbrellas are arranged along the poolside, with trees providing natural shade in the background. A gazebo is also present, enhancing the relaxing ambiance of the space.
Villa in Camucia

Apt. Rolando-Tenuta VillaAugusto

4.97 out of 5 average rating, 33 reviews
Top Guest favourite
An outdoor dining area is set with a green stone table, featuring neatly arranged plates, silverware, and glassware. A blue ceramic pot and a bottle of wine are included. The background reveals an infinity pool overlooking a lush forest with rolling hills under a partly cloudy sky.
Villa in Gaiole in Chianti

Montemarcoli

5.0 out of 5 average rating, 34 reviews
Guest favourite
An outdoor dining area is presented under a wooden pergola, featuring a long table set for meals. Soft lighting is provided by hanging fixtures, and the surrounding lush greenery complements the rustic stone structure in the background.
Villa in Lucignano

Villa Eleonora

4.82 out of 5 average rating, 17 reviews

Destinations to explore