Arezzo Houses for rent With Pool, Rent Furnished or Unfurnished Detached Houses, Villas and Single Family Homes

House in Arezzo, Italy

€39,249 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Air Conditioning

WiFi

Rosewood Manor

This Tuscan villa was once a hotel, so it’s well set up for large groups. All of the bedrooms are en-suite, there’s an industrial kitchen, and the huge lounge has plenty of sofas. With an indoor and outdoor pool, you can swim in every season here. Plus there’s a sauna and two of the en-suites have Jacuzzi bathtubs. The decor feels a little dated – particularly the bathrooms – but we love the formal dining room and the conservatory overlooking the Tuscan countryside. Located in the centre of Valdichiana, there are plenty of opportunities for hiking in the area. Or you can jump in the car for a day trip to the hilltop town of Cortona or the Medieval city of Arezzo. *The swimming pools aren’t fenced. If you're bringing little ones, they'll need to be supervised at all times. *The traditional decor here might not be to everyone's taste. It feels a little dated in parts. *Due to this home's location, we recommend hiring a car to...

House • 8

• 8

• 4,036 ft2 • pets

€

54,705 EUR /Month

Term: Monthly

House in Arezzo, Italy

€54,705 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Green - White

With a tennis court, volleyball court, and a five-a-side football pitch, this home is perfect for those seeking an active holiday in Italy. It’s in the green hills of Valdarno Aretino, close to trails for hiking and mountain biking. You’ll also be within easy reach of Siena, Florence, and Arezzo, giving you plenty of inspiration for day trips. When you’re not out exploring, you’ll enjoy having this peaceful space to call home. One swimming pool has a counter-current system, and the other boasts a hydromassage feature for a more relaxing soak. Perfect for several family groups, this home is spread between the main villa and two annexes. *Your host can provide a cot and high chair for little ones. *The swimming pools are open from the last Saturday in April until the first Saturday in October. *Four tennis rackets are provided for the tennis court. *There’s free parking at this home. *This home comprises the main villa a...

House • 8

• 7

• 3,229 ft2 • pets

€

14,928 EUR /Month

Term: Monthly

House in Arezzo, Italy

€14,928 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Light of Tuscany

Sandwiched between Siena and Arezzo, this villa is ideally suited to large get-togethers. It consists of three cosy apartments, split between a stone villa (one on each floor) and a cottage. Safe to say, you'll have more than enough space here to spread out – plus plenty of spots to retreat to when you need a little quiet. We love the uninterrupted views across the rolling hills and fields. They're the perfect backdrop for alfresco dining or swimming in the private pool. With archery, table tennis, and a swing set for little ones, dull moments will be few and far between. *This home is divided between a converted barn-style cottage and a stone villa with two apartments. Each has its own kitchen and dining area. The two apartments in the main villa have their own living space. *Well-behaved dogs weighing up to 30kg are welcome to join you here. *Air conditioning is only available in the bedrooms. *Your host provides a free ...

House • 5

• 2

• 1,883 ft2 • pets

€

13,344 EUR /Month

Term: Monthly

House in Arezzo, Italy

€13,344 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

This quintessentially Italian home is nestled in the countryside just 5 kilometres from the beautiful town of Cortona. Days here can be spent hiking, cycling and exploring the historic hilltop towns of Tuscany. There’s also a private pool, a bocce court and a terrace with a barbecue – perfect for magical sunset meals. Inside, the rooms are traditional and full of character with plenty of space across the two floors to spread out. One of the rooms has bunk beds – making this a great option for families travelling with children. *Free parking is available for up to four cars. *This home is spread across two floors with stairs. *The two single beds in the fourth bedroom can be arranged as a double on request. *Please note the air conditioning is on the first floor only. *A weekly linen change is included in your stay. *If you're travelling with little ones, your host can provide a cot and high chair for free. You'll n...

House • 8

• 8

• 4,844 ft2 • pets

€

45,171 EUR /Month

Term: Monthly

House in Arezzo, Italy

€45,171 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Tuscan Muse

With views of cypress trees, vineyards and rolling hills, this home delivers the perfect setting for a rustic Italian escape. The rooms are traditional and family-friendly, the garden features a private pool (open seasonally), plus there is a jacuzzi and steam room. Your host can also help organise a range of lovely extras, including private chefs and wine tastings. And while there is plenty to keep you at home, this is a great base from which to explore the region. The nearest small town is just a short walk away, while Arezzo is just a forty-minute drive from here. *Due to this home's location, we recommend hiring a car to get the most out of your stay – there is also private parking for up to four cars. *This home is spread across three floors with two ground floor bedrooms and bathrooms. Please also note three of the bedrooms have a mezzanine level. *There is daily housekeeping included in your stay (from 9.30am to 12.30...

House • 5

• 5

• 1,938 ft2 •

€

19,803 EUR /Month

Term: Monthly

House in Arezzo, Italy

€19,803 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

The Garden Table

Buried deep within the vineyards and olive groves, this rural retreat offers ample outside space for those wanting a quiet getaway to Tuscany. The interiors are rustic and traditional, so the decor won't be to everyone's taste, but most of your time will be spent outside. With a well-kept garden and private swimming pool, there's plenty of space to while away the afternoons here. Alfresco meals are best enjoyed on the covered dining patio, although, the neighbouring hamlet of Montegonzi offers authentic eateries and bars if you don't feel like cooking. You'll need a car to explore but prepare for a hilly, uneven drive at times. *Due to this home's location, you'll need a car to get the most out of your stay. There’s free parking for up five cars. *There's a double bedroom on the ground floor, although you'll need to climb stairs to reach the other bedrooms. *The double beds can be configured as twins if required – you’ll nee...

House • 3

• 3

• 2,153 ft2 •

€

25,536 EUR /Month

Term: Monthly

House in Arezzo, Italy

€25,536 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Tuscany Soul

With a private swimming pool, sun-drenched terraces and a private spa that includes a sauna, Turkish bath and massage table, it’s impossible not to relax here. Set just five kilometres from the centre of historic Cortona, this charming villa is an ideal retreat for a family or group of friends. With daily breakfast included, you can start the day in a leisurely fashion on the terrace, just the spot for sunny alfresco dining. And if having breakfast prepared has given you the taste for taking it easy, you’ll find a selection of eateries nearby for authentic Tuscan food. *While not all bathrooms are photographed, expect the style and quality to be consistent with the rest of the home. *If you're travelling with little ones, your host can provide a cot for free. You'll need to request it in advance. *The swimming pool, open between 1st May and 30th September, isn't fenced and there are open tread stairs here. If you're bringing ...

House • 9

• 8

• 3,229 ft2 •

€

19,056 EUR /Month

Term: Monthly

House in Arezzo, Italy

€19,056 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Tuscany in Bloom

Made for outdoor living and large family gatherings, this home is sure to jump high up on your wishlist. We love the space this home has, and with two apartments independent from the main villa, it’s perfect for extended families where two couples are seeking a bit of added privacy. With traditional interiors, it’s a comfortable place to call home – but it was the outdoor space that caught our eye. Sun-kissed terraces, alfresco dining opportunities, a private pool and hot tub, and all a short drive from the beautiful hilltop town of Cortona. *This home has two independent apartments on the first floor, accessed via an external staircase. Each apartment has a bedroom, bathroom and kitchenette. *The swimming pool, open between 20th May and 30th September, isn't fenced. If you're bringing children, they'll need to be supervised at all times. *The hot tub is available for use between April and October. *If you're travelling...

House • 4

• 2

• 1,399 ft2 •

€

12,048 EUR /Month

Term: Monthly

House in Arezzo, Italy

€12,048 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

A Taste of Nature

This rustic hillside villa boasts gorgeous views from its multi-level garden and private pool. We think it's great for families – the sleeping arrangements have some flexibility, with one of the twin beds able to be converted to a double, and the mosquito screens in every room add some extra practicality. Furry friends are welcome, and your host can provide a free cot and high chair for little ones. Not to mention the location – despite the rolling green landscape, you'll be an easy drive from the Chianti region's charming towns, known for their food and wine. *The road up to this house is even but not paved, and there is space for up to two cars to park. *One well-behaved dog is welcome to accompany you during your stay. *Your host can provide a cot and high chair for free. *The pool is open from May to September. *One of the twin rooms can be converted to a double bed if you request this at the time of booking. *Tw...

House • 3

• 2

• 1,184 ft2 •

€

8,616 EUR /Month

Term: Monthly

House in Arezzo, Italy

€8,616 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

The Tuscany Groove

Rustic and cosy, this typically Tuscan home sits in a peaceful spot within walking distance of Pergine Valdarno, as well as being ideally located for dreamy day trips to Siena, Florence and Arezzo. Outside, you'll find a lush garden filled with fragrant herbs, as well as an elegant infinity pool which provides some beautiful views over this home's hilly surroundings, and a hot tub on a covered terrace is ideal for soaking in at sunset. Inside is characterful, with exposed beams and quaint furniture, and although the light is a little lacking, it makes a snug space to retreat to after busy days in the sunshine. *While the home can sleep up to five people, the maximum occupancy is four guests. *Well-behaved dogs under 30kg are welcome to accompany you during your stay. *The swimming pool is only available for use between 1st May and 1st September. It isn't fenced, so children will need to be supervised at all times. *Due to...

House • 4

• 3

• 2,153 ft2 •

€

11,712 EUR /Month

Term: Monthly

House in Arezzo, Italy

€11,712 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

WiFi

Sweet Orange Peel

Tucked away amongst olive groves and vineyards in the countryside of Chianti, within easy reach of the vibrant cities of Florence, Siena, and Arezzo, this home makes a great base for exploring gorgeous Tuscany. The home itself is typically Tuscan, with antique decor and terracotta tiled floors – but the garden is the sparkliest jewel in the crown, where you'll find a gorgeous dining terrace with climbing vines that provide ample shade, plus a private outdoor pool for making happy memories in the sunshine. *Well-behaved dogs under 30kg are welcome to accompany you during your stay. *The swimming pool is only available for use between 1st May and 1st October. It isn't fenced, so children will need to be supervised at all times. *Due to this home's location, we recommend hiring a car to get the most out of your stay. There is free parking for up to four cars at the home. *Some of the bedroom curtains here don't fully block o...

House • 2

• 2

•

€

13,128 EUR /Month

Term: Monthly

House in Arezzo, Italy

€13,128 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Air Conditioning

WiFi

A Sweet Symphony

Set amidst the verdant greenery of the Tuscan countryside, this elegant home invites you to experience the timeless charm of Italian living. And from the moment of arrival, the atmospheric presence of the villa feels inspiring. Formerly a church that belonged to an old noble property, the owners have sensitively restored this building into a home that shines with character and poetic beauty. From the traditional features to the art and objects, every detail brings a quality of joy to daily life. And whether you’re gazing at the garden views from the kitchen, sipping coffee on the terrace or soaking in the bathtub, it’s easy to settle in and feel at home here. Stepping outside, you’ll discover an idyllic sanctuary – a natural haven perfectly poised for refreshing morning swims, long lunches and sunset drinks. Take a short stroll and you’ll find the village of Pergo is just fifteen–minutes away – there’s a supermar...

House • 6

• 6

• 5,382 ft2 •

€

27,510 EUR /Month

Term: Monthly

House in Arezzo, Italy

€27,510 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Air Conditioning

WiFi

The Sun Rose

Time stands still at this 18th-century villa nestled in the heart of the Tuscan countryside. The rooms perfectly embody traditional Italian charm, while the garden offers sweeping views across the hills – making this the ideal setting for a restorative retreat or intimate celebration. There’s also a private pool and jacuzzi (available on request), with multiple lounging spots to sit back and savour the stillness of this rural location. And when you’re in search of adventure, it’s just a short drive to the amenities in Monterchi, while the majestic cities of Arezzo, Siena and Florence are close enough for day trips. *Due to this home's location, we recommend having a car to get the most out of your stay – there is also free private parking. *This home is spread across three levels with no internal lift – there are also steps leading down to the pool. *Please note the swimming pool is only available from the 11th of April to th...

House • 10

• 9

•

€

37,086 EUR /Month

Term: Monthly

House in Arezzo, Italy

€37,086 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Enchanted Delight

Escape to the Tuscan countryside when you stay at this charming villa. The accommodation is set across three traditional buildings and an annexe, providing plenty of space for a big family holiday or group getaway with friends. Lounge by the scenic swimming pool to savour the Italian sunshine. Gather on the terrace for an al fresco feast. Or head out to explore the rolling hills and vineyard vistas that make Tuscany so special. This rustic retreat is ideal for getting away from it all, where the only task on your to do list is embracing what the locals call la dolce vita. *The accommodation is set over three separate buildings and an annexe. *While the home can sleep up to twenty people, the maximum occupancy is eighteen guests. *The swimming pool isn't fenced. If you're bringing little ones, they'll need to be supervised at all times. *The swimming pool is only available for use between May and October. *While not all ...

House • 11

• 12

•

€

37,170 EUR /Month

Term: Monthly

House in Arezzo, Italy

€37,170 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Etruscan Garden

Escape to Tuscany at this rustic countryside villa, perfect for large groups. Surrounded by rolling hills and expansive gardens, you can unwind by the pool, dine under the shaded gazebo, or simply admire the countryside. Nearby treasures like the Etruscan city of Cortona, the medieval villages of Castiglione Fiorentino and Lucignano, and the historic Montecchio Vesponi Castle are all a short drive away. After a day of exploring Tuscany, fire up the barbecue for an alfresco dinner or challenge your fellow guests to a game of pool. *If you're travelling with little ones, your host can provide a cot and high chair for free. You'll need to request them in advance *The swimming pool isn't fenced. If you're bringing little ones, they'll need to be supervised at all times. The pool is only available for use between 1st May and 15th October, with other periods available upon request. *Due to this home's location, we recommen...

House • 5

• 5

• 3,767 ft2 •

€

27,363 EUR /Month

Term: Monthly

House in Arezzo, Italy

€27,363 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Courtyard Sunsets

Immerse yourself in the peace and prettiness of the Tuscan countryside from a stunning 15th-century villa. The villa is split into four apartments, making it perfect for several family groups travelling together. It’s perched on a hill within a wine- and oil-cultivating estate, amid beautiful scenery. The views can be admired from the private pool and from the courtyard, where you can dine alfresco. Inside, there’s a wellness area with a gym, a hammam, and a hydromassage tub. You’ll be within easy reach of the shops and restaurants of Monte San Savino, and can take day trips to Siena, Arezzo, and Florence. *This home comprises four individual residential units, each with a separate entrance. Two of the apartments are on the first floor, accessible via a flight of stairs. *Two of the double beds can be unzipped into twin beds if preferred Air Conditioning Barbeque Central Heating Child Friendly Coffee Maker Co...

House • 8

• 6

• 3,767 ft2 •

€

13,656 EUR /Month

Term: Monthly

House in Arezzo, Italy

€13,656 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

The Tuscan Song

If you’re in search of a traditional Tuscan escape, this home delivers a great solution. Just 10 kilometres from Cortona, this rustic sanctuary consists of three independent apartments (each with its own entrance) – making it a great option for groups and families. It’s worth noting some of the furnishings are a little dated, but you will find a peaceful garden, a private pool and a large terrace with a barbecue. Your host can also help organise a range of extra services, including cooking classes and spa treatments. From here, it’s just a short drive to local amenities, while majestic cities like Arezzo and Siena are also within easy reach. *Please note this home is spread across three floors and consists of three apartments. Each floor has its own kitchen and entrance. There is also an adjoining annexe with a dining room. *While not all of the rooms are photographed, expect the style and quality to be consistent with the rest ...

House • 7

• 7

• 4,306 ft2 •

€

18,600 EUR /Month

Term: Monthly

House in Arezzo, Italy

€18,600 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Take Me to Toscana

Halfway between Arezzo and Siena, this 18th-century farmhouse makes a fantastic base for exploring Tuscany. The garden will surely be a hit, featuring a private pool (open seasonally), a loggia with a brick barbecue, and a terrace where you can tuck into alfresco meals – not to mention plenty of lawn space where kids and pets can let off some steam. Inside, though dated, certainly doesn't lack charm. We love all the character features, from the timber beams on the ceiling down to the terracotta floors. With seven en-suite bedrooms (including two on the ground floor), it’s a great option for extended families and large friend groups. *Up to two well-behaved pets are welcome to join you. *If you're travelling with little ones, your host can provide two cots and two high chairs on request. *The dated interiors here aren’t up to Plum’s typical standards. We let this one into our collection on behalf of the garden and the location...

House • 2

• 1

• 915 ft2 •

€

5,424 EUR /Month

Term: Monthly

House in Arezzo, Italy

€5,424 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Tuscan Barn Retreat

In the heart of the Tuscan countryside, this lovingly restored stone barn offers an ideal retreat. From this home's hilltop location, there are stunning views of the surrounding olive-covered hills. You can enjoy the vistas from the terrace and private saltwater pool, while inside, the traditional and rustic decor creates a homely feel. Just 500 metres from this place, you’ll find the local town with all of its amenities or go wine tasting at the renowned Petrolo winery just 2 kilometres away. *This converted barn is set over two levels. *While the home can sleep up to four people, the maximum occupancy is three guests. *Well behaved pets are welcome here. *The swimming pool is only available for use between May and October. *There's free parking for three cars here. Air Conditioning Barbeque Beach / Pool Towels Central Heating Child Friendly Coffee Maker Dishwasher EV Charger Fan Fenced ...

House • 5

• 4

• 4,090 ft2 •

€

21,864 EUR /Month

Term: Monthly

House in Arezzo, Italy

€21,864 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Tuscan Geraniums

Set on a 3-hectare estate featuring woodland and olive groves, this rural idyll offers peace and relaxation. Surrounded by a beautiful garden filled with flowers and herbs, there’s an outdoor living area with a gazebo and barbecue, as well as a swimming pool with whirlpool jets. Inside, there’s a large living room, a study, and a dining room connected to the traditional kitchen. There’s also another kitchen and diner with a wood stove in the portico. When you want to explore, Bucine is a short drive, while designer outlets, including Prada, are around 2 kilometres away – Arezzo and Siena can also be easily reached by car. *This home is set over two levels. *The owners live in an annexe about 50 metres from the house and are available if you need them. *The swimming pool is only available for use between the end of April and the beginning of October. *Your host can provide a cot and high chair for free. You'll need to requ...

House • 8

• 8

• 3,444 ft2 •

€

65,037 EUR /Month

Term: Monthly

House in Arezzo, Italy

€65,037 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Chianti Vista

Views of the verdant hills surrounding this home make it a splendid spot for relaxation. The villa boasts a gym, yoga, and massage space in an annex near the swimming pool, within the well-kept garden. Dine under a pergola while watching the sun set over the Val d’Orcia, after a day spent outside in the sunshine. The stone-clad main house and renovated barn have classic Italian features including exposed wooden beams, but these are combined with modern furniture and art. The result? A stylish home-from-home perfect for a large group. *Your host can provide a cot and high chair for little ones. *There’s free parking at this home. *This home comprises the main house, a barn, and an annex. *Your host has arranged daily housekeeping services. *The caretaker lives on the estate, a ten-minute drive away. *Six of the bedrooms can be set up with double beds or twins Air Conditioning Barbeque Bathtub Blender<b...

House • 9

• 7

• 6,781 ft2 •

€

17,856 EUR /Month

Term: Monthly

House in Arezzo, Italy

€17,856 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

WiFi

Tuscan Views

This traditional Tuscan home is located in the stunning Chianti hills. Made up of two stone farmhouses rented as one, it’s a great choice for a family reunion or group getaway. You’ll be doubling up on living rooms, kitchens, and dining rooms so there’s plenty of space for everyone, and two of the bedrooms have three beds – perfect for families or children. While the rustic decor inside won’t appeal to everyone, we think the outdoor space, with its panoramic views, private pool, and alfresco dining terrace, will be a crowd-pleaser. Location-wise, you’ll find a shop and a restaurant 1 kilometre away, and for day trips, the Medieval town of Arezzo is a 25-kilometre drive. *This home comprises two farmhouses, each with its own bedrooms, bathrooms, living room, kitchen, and dining room, rented as one. *The swimming pool is only available for use between 27 April and 19 October. The pool isn't fenced so children will need to be super...

House • 5

• 5

• 4,047 ft2 •

€

20,328 EUR /Month

Term: Monthly

House in Arezzo, Italy

€20,328 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Tuscan Shadows

Set high in the Tuscan hills, this villa has everything you need for a carefree stay. With a private pool and two terraces, you'll probably spend most of your time in the garden. The hot tub is the icing on the cake – it's the best spot to admire those sweeping views. While the traditional interior isn't as impressive, there's no shortage of space. The fifth bedroom is in a separate cottage, complete with a lounge and kitchenette – perfect for grandparents or a couple wanting extra privacy. A car is a must here, but you'll be within driving distance of Arezzo (25km), Cortona (13km), and the small village of Castiglion Fiorentino (5km). *The fifth bedroom is in an independent cottage. It also has a kitchenette, a living area, and a private entrance. *The first floor is divided into two separate areas, with no connecting door between them. *If you're travelling with little ones, your host can provide a free cot and high chair ...

House • 5

• 5

• 2,583 ft2 •

€

16,392 EUR /Month

Term: Monthly

House in Arezzo, Italy

€16,392 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

The Chard Rose

This beautiful Tuscan home caught our attention due to its inspiring views and ample outside living space. Consisting of a farmhouse and a cottage, you'll have access to the well-kept gardens and lovely terraces to help you soak up the rural setting. We think it's a perfect fit for families, due to the abundance of space and fully-fenced swimming pool (complete with a diving board) – plus you've got a table tennis area, sun loungers, a pergola with deck chairs and a covered patio for alfresco suppers. Though you will need a car to explore the region, you'll find the beautiful town of Levane nearby for local amenities. *Due to this home's location, you'll need a car to get the most out of your stay. There’s free parking on-site parking for two cars. *The swimming pool is only available for use from mid-May to September. *If you're travelling with little ones, your host can provide a cot and high chair for free. You'll need to...

House • 11

• 11

•

€

28,014 EUR /Month

Term: Monthly

House in Arezzo, Italy

€28,014 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Air Conditioning

WiFi

Sweet Vita

Overlooking vineyards, rolling hills and woodland, this private estate sits like a gateway to the natural beauty of Tuscany. There are two villas here, one of which dates back to 1700 while the other is a traditional Tuscan farmhouse – together they set the tone for a restorative retreat or intimate celebration. You’ll also find two private pools, a barbecue and multiple terraces to relax and savour the unique charm of this location. From here, it's just a 250-metre stroll to a winery and restaurant – perfect for sampling local produce. And for explorations further afield, it's just a ten-minute drive to the hilltop city of Arezzo. While not all of the rooms are photographed, expect the style and quality to be consistent with the rest of the home. *Please note this home consists of two independent villas each with its own swimming pool. The first villa sleeps 12 guests and has two floors connected by external stairs. The second ...

House • 4

• 3

• 2,045 ft2 •

€

18,672 EUR /Month

Term: Monthly

House in Arezzo, Italy

€18,672 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Tuscan Sunflower

A few kilometres from Cortona, this old farmhouse makes a rustic retreat for families. With a private pool, sprawling gardens, and a panoramic terrace, you'll have plenty of time to enjoy the Tuscan sun. The inside, meanwhile, is filled with traditional details like wooden beams and exposed stone. You'll need to be comfortable climbing stairs here, and it's worth noting that air conditioning is only available in the bedrooms. Still, we think this villa is perfect if you want a characterful, cosy home in the heart of Tuscany. *If you're travelling with little ones, your host can provide a cot and high chair upon request. *Air conditioning is only available in the bedrooms. *Two bedrooms are connected internally and share a terrace, though they also have independent entrances from the outside. *The swimming pool is only available to use between the last Saturday in April and the first Saturday in October. *There are two i...

House • 3

• 4

•

€

24,087 EUR /Month

Term: Monthly

House in Arezzo, Italy

€24,087 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Air Conditioning

WiFi

A Tuscan Sunrise

Tucked between olive groves and a pine forest, this cosy villa is a scenic drive away from Cortona, Arezzo and Pienza – but you might not want to leave once you're here. The three bedrooms (each with their own bathroom) are downstairs, while upstairs it’s all about spending time together – cooking in the kitchen, chatting around the travertine island, or sharing a bottle of local wine at the glass-and-timber table made from a tree that once grew on the property. Outside, you’ve got a pool, a jacuzzi, and a rooftop terrace with front-row seats to the sunset over Castiglion Fiorentino. It’s peaceful, spacious and completely private – a proper countryside escape without feeling remote. *Due to this home's location, we recommend hiring a car to get the most out of your stay. There’s free parking for up to two cars onsite. *The swimming pool isn't fenced. If you're bringing little ones, they'll need to be supervised at all times. <br...

House • 4

• 5

• 2,691 ft2 •

€

15,840 EUR /Month

Term: Monthly

House in Arezzo, Italy

€15,840 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

WiFi

Celebrate the Moment

Nestled among the olive groves of Chianti, this home welcomes you to enjoy mesmerising views and ultimate relaxation. There’s a private pool and a perfectly positioned terrace for sunset drinks and alfresco dining. Inside, the rooms are traditional, simple and well suited to families. You’ll also find one of the bedrooms is located in the pool house – providing a sweet and private sanctuary for two guests. You will need a car to get around here, but it’s just a short drive to the nearest amenities, while the beautiful Castelnuovo Berardenga (renowned for its delicious wine, restaurants and castles) is also just a short drive away. *This home can accommodate eight guests with prior approval from the host. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *Please note the swimming pool is available for use from May to October. *Private parking is available for up to three...

House • 5

• 4

• 2,691 ft2 •

€

18,792 EUR /Month

Term: Monthly

House in Arezzo, Italy

€18,792 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Air Conditioning

WiFi

Valley Vista Villa

Located just one mile from the hilltop town of Cortona, this Tuscan villa is made up of two apartments in one charming and traditional farmhouse. Both apartments have their own separate entrances, making this a great choice for large groups. Outside, the private pool is fenced and perfectly placed for stunning views, and children will love the expansive grounds. Animal lovers can bring their furry friends along, but it's important to note that a couple of dogs and even a friendly donkey live on the land, and the owner of the home lives nearby. Despite this though, you'll be granted full privacy during your stay. *There are three private parking spaces outside this home. Cortona can be reached on foot, but we recommend hiring a car here to get the most out of your stay. *Well-behaved pets are welcome to join you at this home with prior host approval. *Two friendly dogs and a donkey live on the property, so it may not be suitab...

House • 2

• 2

•

€

9,624 EUR /Month

Term: Monthly

House in Arezzo, Italy

€9,624 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

A Tranquil Place

Set in the foothills fringing the medieval town of Cortona and surrounded by olive and fir trees, the setting of this traditional cottage couldn't be more Tuscan if it tried. The interiors may be too rustic for some, but they would perfectly suit a small family or group of friends looking for a fuss-free stay. That lengthy pool fringed by vast lawns for little ones to have a runabout is all yours – and there's a ping pong table to break up pool time. Location-wise, Cortona is within walking distance, just 800 metres away – albeit uphill. And just a little further, discover Lake Trasimeno in Umbria. *There is ample private parking outside the villa. *If you’re travelling with little ones, the pool area has gated access for added peace of mind. *This cottage is semi-detached alongside a separate dwelling which is permanently occupied. The owner's cottage is also within the grounds. The use of the swimming pool is solely for yo...