House • 2 People • 1

• 1

•

From

€

160 /night

Min Stay 1 night

Grosseto, Italy

€ 160 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Maremma Dreaming

Tailor-made for two, this ground-floor villa boasts modern touches throughout, along with an indoor Jacuzzi to unwind in after a busy day exploring the local area. Keen for a morning swim? After breakfast on the private terrace, head to the communal pool area for a refreshing dip to start the day. Locally, within three kilometres, there’s a selection of villages with Tuscan eateries and small grocery shops. If you’re looking for a little more, it’s a sixteen-minute drive to Roccalbegna – packed with a lot more amenities, it's definitely worth a visit. *This home is set on a resort alongside neighbouring homes. Expect to bump into other guests during your stay. *You'll have access to three on-site swimming pools here, open between May and October. They're shared with the resort's other residents. *The swimming pools aren't fenced. If you're bringing children, they'll need to be supervised at all times. *Your host can provide a cot an...More Details

Booked

Available

Arezzo, House for rent

House • 10 People • 5

• 5

•

From

€

718 /night

Min Stay 1 night

Arezzo, Italy

€ 718 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Peaceful Love

Escape to the beautiful Tuscan countryside, with a stay in this traditional Italian home. You’ll be welcomed by a serene garden with a pool and a covered veranda with an outdoor kitchen for alfresco dining. There’s also a wellness area with a sauna and a hot tub to ensure optimum relaxation. Inside, you’ll find tradition and contemporary comfort with all five bedrooms featuring en-site bathrooms for privacy. We recommend hiring a car to get around here, but it’s just a short drive to Ambra where you’ll find the nearest restaurants and shops. You can also drive to Arezzo, Florence and Siena for inspiring day trips. *Private parking is available for up to eight cars. There is also a charging station for electric vehicles. *A weekly linen change is included in your stay. *Please note this home is set across two floors with stairs. *If you're travelling with little ones, your host can provide a cot and two high chairs for free on req...More Details

Booked

Available

Siena, House for rent

House • 6 People • 3

• 3

•

From

€

476 /night

Min Stay 1 night

Siena, Italy

€ 476 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Chianti Splendour

With far-reaching views of the rolling Chianti hills, it’s impossible not to relax in this villa. Traditional yet modern, this home promises a true taste of Tuscany, alongside plenty of space to relax. We love the three tiered terraces, each offering something different – alfresco dining on the top terrace, bowls on the middle, and a private pool on the lower. And, being situated next to a working winery, you’re perfectly placed for a spot of wine tasting and some authentic Tuscan food – all of which can be organised by your host. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *The twin bedroom can be set up as a double upon request. *There are stairs to climb here, including in the outdoor space to access different terraces. It may not be the best option for those with reduced mobility. *We recommend hiring a car to get the most out of your stay – on-site parking is available f...More Details

Booked

Available

Florence, House for rent

House • 12 People • 5

• 4

•

From

€

2,465 /night

Min Stay 1 night

Florence, Italy

€ 2,465 /Night (minimum stay 1 night)

Swimming Pool

WiFi

Villa Chianti

This stunning home is nestled amid 600 hectares of vineyards and olive groves in Chianti Classico. It’s a great area for hiking and cycling, visiting wineries, and taking day trips to Florence – it’s only thirty-five minutes away. The villa has been beautifully renovated to preserve its original features, so you can expect exposed oak beams, terracotta floors, and rustic Tuscan furniture. The original stable has been converted into an event venue. Outside, the vast garden is centred around a swimming pool, and there’s a covered dining area with a barbecue. *There’s free parking at this home. We recommend hiring a car to get the most out of your stay. *At full occupancy, two guests will sleep in the study. *The swimming pool is open from 13th April to 12th October. *There’s a ground-floor twin bedroom. The rest of the bedrooms are on the first and second floors. *Your host can provide a cot and high chair for little ones. *The stable...More Details

Booked

Available

Grosseto, House for rent

House • 16 People • 7

• 6

•

From

€

4,420 /night

Min Stay 1 night

Grosseto, Italy

€ 4,420 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Quiet - Serene

It might not look it, but this home is just a short walk from a private beach in Roccamare. Nestled in a tranquil pine forest, the villa is made for beach days with family or friends – on the shoreline, you'll have access to a private cabana with a dining table and a separate cabin, perfect for storing beach equipment. Cool off in your private pool, shaded by the surrounding pine trees, or relax on a deck chair in the garden. The spacious outdoor sofa is the perfect spot to gather for drinks in the evening, while the sleeping arrangements are ideal for little ones – we particularly love the five-person bedroom and double bunk beds. While there's plenty to occupy your time with here, you're also just a short drive from Follonica. *If you're travelling with little ones, your host can provide a cot and baby bed for free on request. Please supervise children around the swimming pool, as it is unfenced. *Due to this home's location, we re...More Details

Booked

Available

Grosseto, House for rent

House • 4 People • 2

• 1

•

From

€

138 /night

Min Stay 1 night

Grosseto, Italy

€ 138 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

The Tuscan Sunset

This charming villa is located in the heart of the Tuscan countryside, just a short drive from the historic town of Grosseto. Sure, its traditional interiors may not be everyone’s cup of tea, but you’ll find everything needed for a relaxing stay here and the outdoor space will tick all your holiday boxes. The private terrace is just the ticket for alfresco meals and the perfect place to soak up the valley views. And when the heat gets too much, take your pick of three on-site shared pools to cool off in the Tuscan sun. *This home is set on a resort alongside neighbouring homes. Expect to bump into other guests during your stay. *You'll have access to three on-site swimming pools, open between May and October, and a Jacuzzi here. They're shared with the resort's other residents *The swimming pools aren't fenced. If you're bringing children, they'll need to be supervised at all times. *If you're travelling with little ones, your host ...More Details

Booked

Available

Siena, House for rent

House • 8 People • 4

• 3

•

From

€

2,009 /night

Min Stay 1 night

Siena, Italy

€ 2,009 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

The Vine Song

Accessible via an unpaved, cypress-lined road and perched on sloping, vineyard-covered hills, this stylish stone villa is Tuscany at its best. Whether you’re here for an intimate wedding or a big family holiday, the place will set your heart pounding. The interiors have preserved the grace of earlier ages while adding the essential modern cons and amenities. Exposed wood beam ceilings, tiled floors covered with vibrant carpets, and gorgeous vintage furniture make you feel at home, yet so far away from the current era. The master bedroom comes with a four-poster bed, and overall, all sleeping quarters exude a pampering feel accentuated by the gorgeous period furniture. We love the huge dining room, the walls of which are lined with well-stocked bookshelves. After a hearty meal, grab a book, amble outside to the sundeck and lose yourself in another world. When the warmth overwhelms you, take a cooling dip in the massive pool. In the eveni...More Details

Booked

Available

Lucca, House for rent

House • 2 People • 1

• 1

•

From

€

141 /night

Min Stay 1 night

Lucca, Italy

€ 141 /Night (minimum stay 1 night)

Swimming Pool

WiFi

Italian Stone

Tranquil doesn’t even begin to describe this wonderful apartment. It’s tucked away in the hills above Bagni di Lucca, in a tiny village that’s quiet even in the height of summer. You’ll share the grounds and outdoor pool with four villas, but there’s plenty of space. Stunning views can be admired from almost every angle here, with far-reaching vistas of the surrounding hills and forests. The apartment is rustic in style, with exposed stone walls and terracotta floor tiles. It’s the perfect retreat for a romantic getaway. *There’s free parking at this home. We recommend hiring a car to get the most out of your stay. *There are stairs to climb at this home so it may not be suitable for those with reduced mobility. *The communal swimming pool is open from May-September. It’s not heated and the water can be chilly even in summer. The pool is shared between the four villas in this hamlet. *You’ll need to bring your own pool towels. *If yo...More Details

Booked

Available

Tuscany, House for rent

House • 16 People • 11

• 9

•

From

€

2,603 /night

Min Stay 1 night

Tuscany, Italy

€ 2,603 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

The Gem of Tuscany

Experience the grandeur of the past with a stay at this magnificent home situated in the heart of Tuscany. With its history stretching back all the way to the eleventh century, this castello has seen it all – from medieval feuds to Renaissance splendour, and beyond. Arrive to be wowed by the impressive exterior set against the lush greenery of its gardens and the stunning views of the Tuscan countryside surrounding it. You’ll no doubt fall under the spell of this place before even crossing the front door – outside you’ll find a glistening pool, inviting you to take a dip in on those hot Italian afternoons. You can lounge about on the comfy sun loungers, working on your tan and catching up on your holiday reads. As the sun begins to set over the green hills, gather everyone outside for an evening of cocktails and conversation. Inside you'll be greeted by a beautifully preserved interior, which retains its historic glory while at the s...More Details

Booked

Available

Siena, House for rent

House • 10 People • 5

• 5

•

From

€

3,942 /night

Min Stay 1 night

Siena, Italy

€ 3,942 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Dream of Beauty

From its privileged spot in the heart of Crete Senesi, this home opens its doors to classic Tuscan views and timeless Italian charm. Nestled within two acres of private land, you'll find the main house consists of two floors, while the independent annexe has a bedroom and private living area with a mini-fridge. You can also enjoy access to a salt-water pool, Jacuzzi and gym along with a range of personal touches – including private-labelled house wine and a concierge service. From here, leisurely days can be spent in the sweeping gardens or out exploring the region – the historic streets of Siena are just 12 kilometres away, while Montalcino is a twenty-minute drive. *Please note the fifth bedroom is located in the independent annexe which has its own entrance and living area with a mini-fridge. *Daily housekeeping and complimentary toiletries are included in your stay. *It is possible for the twin beds to be arranged as a king-sized...More Details

Booked

Available

Grosseto, House for rent

House • 4 People • 2

• 2

•

From

€

188 /night

Min Stay 1 night

Grosseto, Italy

€ 188 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Maremma's Secret

Situated on a resort with views leading down to distant Grosseto and the sea, this home is all about relaxation. Enjoy alfresco dining on the sun-drenched terrace or simply kick back and relax in the private hot tub. Need to cool off from the heat of the Tuscan sun? The communal swimming pools are just the ticket. Locally, the surrounding villages offer restaurants and small grocery shops, or you can venture a little further to the charming town of Roccalbegna, nine kilometres away and well worth a visit. *This home is set on a resort alongside neighbouring homes. Expect to bump into other guests during your stay. *You'll have access to three on-site swimming pools here, open between May and October. They're shared with the resort's other residents. *The swimming pools aren't fenced and there are open-sided stairs here. If you're bringing children, they'll need to be supervised at all times. *Your host can provide a cot and high cha...More Details

Booked

Available

Siena, House for rent

House • 15 People • 7

• 6

•

From

€

870 /night

Min Stay 1 night

Siena, Italy

€ 870 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Sun of Splendour

If you’re in search of a traditional Italian stay in a beautiful location, this home delivers a great solution. Nestled in a private garden overlooking the Chianti countryside, you’ll be welcomed by stunning views and a private pool with a Jacuzzi. The main house consists of three independent apartments (each with its own kitchen), while an additional annexe provides a cosy space for two guests. It’s worth noting some of the furnishings and decor are a little dated, but you will find plenty of character. Plus, you can explore some of Tuscany’s most beautiful sights. From here, it’s just a thirty-minute drive to Siena, while San Gimignano and Monteriggioni are also within driving distance. *Please note the main house consists of three independent apartments that are not internally connected. There is also an independent annexe with a double room, bathroom and kitchen. *The traditional decor here might not be to everyone's taste. It fe...More Details

Booked

Available

Viterbo, House for rent

House • 9 People • 5

• 4

•

From

€

700 /night

Min Stay 1 night

Viterbo, Italy

€ 700 /Night (minimum stay 1 night)

Swimming Pool

WiFi

Palazzo on the Hill

With stunning views across the Nature Reserve of Monte Rufeno, it’s easy to see why this home caught our eye. Located on the border of Tuscany and Umbria, it’s just a short drive to the village of Trevinano, with easy access to some of the region's most beautiful spots. And while there’s plenty to keep you busy in the surroundings, this home has a lot to offer too. The swimming pool can be heated, the garden is surrounded by olive trees and the terrace is perfectly positioned for idyllic sunset drinks. *Due to this home's location, we recommend hiring a car to get the most out of your stay – there is also free private parking. *For those with reduced mobility, there are four ground-floor bedrooms and two bathrooms here. *The main bedroom on the first floor has its own independent entrance from the outdoor stairs. *You won't find a welcome hamper or basic essentials here, so we'd recommend packing some bits and bobs to get you starte...More Details

Booked

Available

Grosseto, House for rent

House • 6 People • 3

• 4

•

From

€

1,051 /night

Min Stay 1 night

Grosseto, Italy

€ 1,051 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Rolling Hills of Tuscany

With far-reaching views and an abundance of places to enjoy them, it’s not hard to see why this contemporary villa caught our eye. Inside is modern and sleek, perfectly proportioned for a family or group of friends and with the added bonus of a gym and sauna. But outdoors is where this home comes alive. Swim in the private pool, play ping pong, relax on the sun-drenched terrace or dine alfresco – the options are endless. If you can tear yourself away, there’s plenty to keep you occupied in the surrounding area, too. Head to historic Grosseto, the wild beaches of the coast, the vineyards around Montalcino, or the hot springs at Terme di Saturnia. *One well-behaved dog (up to 30kg) is welcome to accompany you during your stay. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *The bedrooms can be set up as doubles or twins on request. *Due to this home's location, we recommend hiring ...More Details

Booked

Available

Siena, House for rent

House • 12 People • 6

• 6

•

From

€

2,939 /night

Min Stay 1 night

Siena, Italy

€ 2,939 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Golden Tuscan Sun

Traditional charm, stunning views and a private swimming pool – this home has everything you could need for a blissful Italian escape. There are two outdoor seating areas, a barbecue and a pizza oven for delicious evening meals. Inside, the rooms are filled with art along with a range of home comforts to ensure optimum relaxation. Exercise enthusiasts will also appreciate the home gym. Daily housekeeping is included in your stay and your host can help organise a range of extra services – including private chefs and wine tastings. You will need a car to get around here, but it’s just a short drive to the nearest amenities in Sarteano, while Montepulciano, Montalcino and Chianciano Terme are all within easy driving distance. *Housekeeping is included for four hours per day. *Please note this home is set across two floors with stairs. It is also possible for the bedrooms to be arranged with two single beds or as a double on request. *If...More Details

Booked

Available

Pisa, House for rent

House • 10 People • 5

• 5

•

From

€

721 /night

Min Stay 1 night

Pisa, Italy

€ 721 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

With Your Love

A serene garden, a private pool and a wonderful location – this home is the ideal base for a blissful Italian getaway. There’s also a solarium, table tennis and an outdoor terrace for alfresco dining and sunset drinks. Inside, the rooms are set across the main house, the annexe and an apartment – making this a great option for groups looking to stretch out and spend quality time together. You will need a car to get around here, but it’s just a short drive to the nearest amenities, while iconic destinations like Volterra, San Gimignano and Pisa are also within driving distance. *Please note the main house is accompanied by an annexe for two guests and an independent apartment for two guests. *If you’re travelling with little ones, your host can provide a cot for free on request. *The swimming pool is available for use from the 1st of May to the 1st of October. *Private parking is available here. Air Conditioning Barbeque Beach / P...More Details

Booked

Available

Florence, House for rent

House • 12 People • 6

• 4

•

From

€

1,916 /night

Min Stay 1 night

Florence, Italy

€ 1,916 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Everyday Love

Nestled in a private estate surrounded by oak trees and olive groves, this eco-friendly home is a true Tuscan sanctuary. Days here can be spent lounging by the private pool, following hiking trails or exploring nearby Florence and San Gimignano (both within driving distance). Whether you’re looking to relax and unwind, host a gathering or simply enjoy the beauty of Tuscany, this home makes it easy to enjoy it all. Inside, the rooms are traditional and family friendly with the handy addition of two kitchens. There is also a renovated stable which can be used for special events. *Please note this home is spread across three floors with stairs. You'll also find two of the bedrooms and one bathroom are located on the ground floor. *It’s worth noting some areas of this home are dated. *Mid-stay linen and towel changes are included for stays longer than five days. *If you're travelling with little ones, your host can provide a cot and ...More Details

Booked

Available

Siena, House for rent

House • 2 People • 1

• 2

•

From

€

256 /night

Min Stay 1 night

Siena, Italy

€ 256 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

WiFi

Tuscan Couplet

We think this cosy little home is the perfect couple's retreat. Step inside and you'll discover rustic details like stone archways, beamed ceilings, and an open fireplace. Outside, the terrace makes a scenic spot to enjoy an alfresco dinner – your host can organise a private chef for a fee. The cherry on top is the private pool, where you can cool off as the sun goes down. With its convenient location near Florence and Siena, this home is the ideal base for exploring the region's rich history, culture, and culinary scene. *There's a double sofa bed here that may be available on request – please speak to your host for more information. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *The traditional decor here might not be to everyone's taste. It feels a little dated in parts. *The pool is only available to use between 1st June and 21st September. *You’ll need a car in this location...More Details

Booked

Available

Florence, House for rent

House • 4 People • 2

• 1

•

From

€

170 /night

Min Stay 1 night

Florence, Italy

€ 170 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

WiFi

Toscana Sunset

With views of the surrounding shared gardens and pool, this Tuscan stone villa is perfect for a relaxing holiday. There’s a private furnished terrace to take in the sunset, while inside, there’s a traditional, well-equipped kitchen for creating some home-cooked cuisine. Situated in the Val d'Elsa countryside you’ll be surrounded by rolling vineyards, olive groves and wooded areas. Places of interest nearby include San Gimignano, Volterra, Florence, and Siena. Or if you fancy a hike, 1 kilometre away you’ll find Sant'Appiano and its 1,000-year-old chapel. *There are five holiday rentals here. The pool, laundry room and barbeque are communal. *The shared swimming pool is only available for use between May and October. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *The second bedroom has twin beds which can be converted to a double bed. *There's free parking on the premises. Balco...More Details

Booked

Available

Tuscany, House for rent

House • 12 People • 6

• 5

•

From

€

636 /night

Min Stay 1 night

Tuscany, Italy

€ 636 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

WiFi

Eternal Joy

Experience the timeless charm of Tuscany with a stay in this traditional home. Nestled in the hills of Chianni, you’ll be treated to a peaceful garden, a private swimming pool and plenty of shaded spots for lazy afternoon siestas. It’s also family friendly with a children’s play area, table tennis and a volleyball net. Inside, the rooms are simple and cosy with all the basics you could need to settle in and unwind. Your host is on hand to help organise special extras like cooking classes and tours. Plus, it’s just a short drive to the nearest amenities in Castellina Marittima, while the nearest beaches are also within easy driving distance. *Please note this home is set within a private estate with two neighbouring homes where the owners live. *Private parking is available for up to ten cars. *A weekly linen and towel change is included in your stay. *If you’re travelling with little ones, your host can provide a cot and high chair...More Details

Booked

Available

Homes for rent in Tuscany Holiday rentals Italian vacation rentals of Detached House and Villas, Single Family Homes - Short term lettings

Found 1089 Tuscany Houses for rent

Grosseto, Italy

Arezzo, Italy

Siena, Italy

Florence, Italy

Grosseto, Italy

Grosseto, Italy

Siena, Italy

Lucca, Italy

Tuscany, Italy

Siena, Italy

Grosseto, Italy

Siena, Italy

Viterbo, Italy

Grosseto, Italy

Siena, Italy

Pisa, Italy

Florence, Italy

Siena, Italy

Florence, Italy

Tuscany, Italy