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Italy Country: Italy (7128) | Region: Tuscany (2161)
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    Found 964 Tuscany Houses for vacation rental

    House • 37 People • 18 20 pool wifi
    From
    7,650 /night
    Min Stay 1 night


    Florence, Italy 

    € 7,650 /Night (minimum stay 1 night)
  • Swimming Pool
    Air Conditioning
    WiFi

    The Chianti Farm


    Consisting of three separate stone villas, this is a beautiful home located in the Chianti wine region of Tuscany, between Florence and Siena. The village of Panzano is just a short walk away, where you can find supermarkets and a weekly market. Each villa has its own garden with a swimming pool and its own kitchen, living and dining room. So, the group can spread out and enjoy some privacy before gathering together in the vast outdoor spaces. Outside you’ll find a hot tub for four people, several terraces including a covered dining area with tables and chairs and a state-of-the-art barbecue. Each villa is a little slice of luxury, but one stands out with an indoor swimming pool and spa in the basement. *This home consists of three separate villas each with its own private swimming, sharing 20 acres of grounds.\n *Daily cleaning (6 hours a day) is included with a stay here and linen is changed weekly.\n *Four of the double bedrooms can...More Details


    • Booked Available
    House • 27 People • 14 14 pool wifi
    From
    5,453 /night
    Min Stay 1 night


    Siena, Italy 

    € 5,453 /Night (minimum stay 1 night)
  • Swimming Pool
    Air Conditioning
    WiFi

    The Art of Tuscany


    With a team of staff on-hand to help at this decadent home, you won't have to lift a fingertip during your stay. Spread across a main house, guest house and suite, you also won't have to compromise on space. The swimming pool, Roman baths, and sauna ensure relaxation. When you're not traversing the hundreds of acres on bicycle or horseback, the on-site observatory allows you to admire the stars. We think some of the decor is a little dated, and it might not be to everyone's taste. But whether you're throwing a wedding, a yoga or tai chi retreat, or you're simply looking for a scenic escape to the Tuscan countryside, this home has it all. *This home consists of a main house (sleeping nineteen), a guest house (sleeping six), and a guest suite (sleeping two). Each has a combination of living rooms, bathrooms, and bedrooms. Some bedrooms may only have external access. Several beds can be configured as twins or doubles on request.\n *Not al...More Details


    • Booked Available
    House • 28 People • 14 13 pets pool wifi
    From
    5,246 /night
    Min Stay 7 nights


    Lucca, Italy 

    € 5,246 /Night (minimum stay 7 nights)
  • Swimming Pool
    Pets Allowed
    Air Conditioning
    WiFi

    Villa Medici


    If you’re celebrating something special or simply looking for a huge, luxury home to gather together in the beautiful Tuscan countryside (ten minutes from Lucca), this is the spot for you. Dating back to the 17th century, you can feel the history of this home in the frescoed ballroom (seating up to 50 people for dinner), lounges set around ancient fireplaces and the shining farmhouse-style kitchen. Bedrooms are spread across the main villa, a converted hunting lodge and former stables in the grounds. Speaking of, the rose gardens, herb gardens and vine-twisted pergolas seem to go on forever. Apart from an inviting outdoor swimming pool, the crowning glory is the dedicated spa with its Turkish bath, sauna and hydrotherapy centre. *This home consists of three separate buildings – the main villa, a former hunting lodge housing four apartments, and the former stables housing two bedrooms.*For those with limited mobility, there's a lift to ...More Details


    • Booked Available
    House • 10 People • 5 5 pets pool wifi
    From
    4,410 /night
    Min Stay 1 night


    Florence, Italy 

    € 4,410 /Night (minimum stay 1 night)
  • Swimming Pool
    Pets Allowed
    Air Conditioning
    WiFi

    Tuscan Spirit


    Standing boldly amid the rolling hills and meadows of Tuscany, it’s easy to see why this home caught our eye. Not only is it visually striking, but it also boasts great views, a private pool and exceptional service. Breakfast is included in your stay, butler service is available throughout the day and a private chef can be arranged for lunch and evening meals. Tennis lovers will also appreciate the access to the estate courts (just a ten-minute drive away), while those in search of an Italian adventure will love exploring nearby Florence – just a thirty-minute drive away. *Due to this home's location, we recommend having a car to get the most out of your stay – please also note this home is located within a private estate. \n *Daily breakfast is included in your stay, along with butler service (from 8am to 12pm and from 6pm to 10pm).\n *There is also a linen and towel change every three days. \n *There are three levels here with no int...More Details


    • Booked Available
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    House • 10 People • 5 5
    From
    4,113 /night
    Min Stay 7 nights


    Monteroni D'Arbia, Italy 

    € 4,113 /Night (minimum stay 7 nights)
  • 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 bed...More Details


    • Booked Available
    House • 15 People • 7 9
    From
    4,107 /night
    Min Stay 1 night


    Grosseto, Italy 

    € 4,107 /Night (minimum stay 1 night)
  • Swimming Pool
    Air Conditioning
    WiFi

    The Artist's Academy


    Staying at this country manor feels like stepping back in time, with its tapestries, chandeliers and grand fireplaces. Though its decor may not be for everyone, it’s certainly a unique place. It’s also an ideal home to share with a large group of people, thanks to its three kitchens, several living areas and the added luxury of all bedrooms having their own en-suite. Outside you’ll find a large garden, boasting a heated pool with hydro-massage, as well as an outdoor terrace complete with bar and barbecue –perfect for alfresco dining. For a change of scenery you can take a fifteen-minute drive to spend the afternoon at Spiaggia Marina di Grosseto beach. *The traditional decor here might not be to everyone's taste. You'll also find expensive artwork and ornaments in this home, so it might not be the best choice if you're travelling with young children. \n \n *The swimming pool isn't fenced. If you're bringing little ones, they'll need to...More Details


    • Booked Available
    House • 16 People • 7 7
    From
    3,994 /night
    Min Stay 3 nights


    Florence, Italy 

    € 3,994 /Night (minimum stay 3 nights)
  • Swimming Pool
    Air Conditioning
    WiFi

    Glitter - Gold


    Perched atop the hills on the outskirts of Florence, this villa is surrounded by jaw-dropping vistas and is ideal for families, friends, or couples travelling together. The grounds boast a private pool, a fire pit, and no shortage of space for children to play and for groups to dine under the sun. For added luxury, your host can help arrange a variety of experiences for an additional fee, from breakfast on the terrace to in-villa massages. You'll definitely need a car here to make the most of this gorgeous location, with Florence just a short drive away, and all its restaurants, shops, and historical hotspots at your fingertips. *While two of the bathrooms aren't photographed, expect the style and quality to be consistent with the rest of the home.*There is space to park for free on the driveway here. Due to this home's location, we recommend hiring a car to get the most out of your stay.*Climbing stairs may be required at this home.*T...More Details


    • Booked Available
    House • 26 People • 13 13
    From
    3,958 /night
    Min Stay 1 night


    Siena, Italy 

    € 3,958 /Night (minimum stay 1 night)
  • Swimming Pool
    Pets Allowed
    Air Conditioning
    WiFi

    Marbled with Flowers


    Ten minutes from Sarteano town and an easy drive from Montepulciano, this charming Tuscan estate has its own outdoor pool and wellness facilities. The gym and spa are well-equipped, with a heated indoor pool, Finnish sauna and professional exercise equipment. Made up of a main home and an annexe, there's plenty of room for large groups to spread out, and for kids and pets to tire themselves out in the garden. You'll have privacy and countryside views, plus it's a great base to explore the Val d'Orcia and Valdichiana regions by car. *Not all bedrooms and bathrooms are photographed, but we expect consistency in style and quality throughout.\n *We highly recommend hiring a car to make the most of your stay.\n *This home is made up of a main house which sleeps sixteen guests, and an annexe which sleeps a further ten.\n *Several of the bedrooms can be configured as twins or doubles by pushing the beds together. The bedrooms in the annexe ar...More Details


    • Booked Available
    House • 10 People • 5 6
    From
    3,831 /night
    Min Stay 1 night


    Radda in Chianti, Italy 

    € 3,831 /Night (minimum stay 1 night)
  • Swimming Pool
    Air Conditioning
    WiFi

    Chianti Sangria


    At this rustic villa, rolling vineyards are on your doorstep. We mean that quite literally – the owners are local winemakers, and they offer tastings in the medieval tower-turned-wine bar. They'll also arrange welcome dinners, cooking classes, private chefs, and other special touches during your stay. As for the home itself, we think it's pretty spectacular. A private pool, sun-kissed garden, and Chianti views await outside, while the somewhat-traditional interior has a few surprises in store – namely, a chef's kitchen, a small gym and a wellness centre boasting a Turkish bath and steamy sauna. Location-wise, Radda is less than 2 kilometres away, and Florence and Siena are great options for day trips. *The fifth bedroom is located in a guest annexe, which has a kitchen, double bedroom and bathroom. It's a good option for guests wanting a bit more privacy.\n *Daily housekeeping (excluding Sundays) is included with your stay. There's a l...More Details


    • Booked Available
    House • 18 People • 10 7
    From
    3,616 /night
    Min Stay 1 night


    Lucca, Italy 

    € 3,616 /Night (minimum stay 1 night)
  • Swimming Pool
    Air Conditioning
    WiFi

    In the Garden of Paradise


    Set within Mediterranean landscaped gardens, this villa is full of charm, with original 17th-century frescoed ceilings demonstrating its impressive history. These days, it keeps its nod to tradition, but even if the style isn’t quite to your taste, you’ll find everything you need here for a restful retreat. Outdoors, the generous gardens offer ample opportunity for little ones to tear around and have fun in the sun, while the grown-ups can relax poolside – or for a real treat, an afternoon spent in the wine cellar will create lasting memories. *While not all bedrooms and bathrooms are photographed, we expect the style and quality to be consistent with the rest of the home.\n *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.\n *The swimming pool isn't fenced. If you're bringing children, they'll need to be supervised at all times. \n *There are stairs to ...More Details


    • Booked Available
    House • 14 People • 7 7
    From
    3,074 /night
    Min Stay 1 night


    Florence, Italy 

    € 3,074 /Night (minimum stay 1 night)
  • Swimming Pool
    Air Conditioning
    WiFi

    The Lavender Rose


    Wine connoisseurs, this one’s for you. Set amongst rolling Tuscan countryside in the Chianti region, you’ll find an abundance of vineyards and wineries in the local area. If you’re not on a tour or a tasting, this villa provides plenty of entertainment at home. With comfortable interiors and all the mod-cons you could wish for, the really special part of this home is the outdoor space. Whether you’re swimming in the private pool or dining alfresco, the peacefulness of your location and panoramic views won’t be lost on you. *If you're travelling with little ones, your host can provide a high chair for free. You'll need to request it in advance.\n *The swimming pool isn't fenced. If you're bringing children, they'll need to be supervised at all times. \n *For those with reduced mobility, there are three ground floor bedrooms with en-suite bathrooms here. Some of the bedrooms in this home feature in-room baths and showers.\n *While we lov...More Details


    • Booked Available
    House • 9 People • 5 5
    From
    3,039 /night
    Min Stay 7 nights


    Grosseto, Italy 

    € 3,039 /Night (minimum stay 7 nights)
  • Swimming Pool
    Air Conditioning
    WiFi

    The Fortune Teller


    In many ways, this is the quintessential Tuscan villa. Formerly a farmhouse belonging to a member of the Borghese family, it sits within a large garden filled with ancient olive trees, herbs and aromatic flowers. From the elevated position, there's a gorgeous view of the Tyrrhenian Sea and local hillsides. In addition to this stunning setting, there's a private swimming pool out in this space, as well as a wisteria-covered pergola complete with an alfresco dining area and a lounge underneath. Heading In through the arched doorways, the interior lives up to the high expectations set by the exterior. A tasteful selection of antique furnishings — like the marble fireplace in the living room — sit next to artworks hanging on the walls and some more contemporary fittings.And to top it all off, there's such a wide range of distractions to be found in the local Monte Argentario peninsula, from the long Fenigila Beach ten minutes' drive away an...More Details


    • Booked Available
    House • 14 People • 7 6
    From
    2,907 /night
    Min Stay 4 nights


    Siena, Italy 

    € 2,907 /Night (minimum stay 4 nights)
  • Swimming Pool
    Air Conditioning
    WiFi

    Little Hills


    You can't beat the views of the beautiful Val D'Orcia, itself a UNESCO World Heritage Site, from this Tuscan farmhouse lying in the Siena Province on a private two-acre estate. Tear yourself away from the vistas, and you'll find a deft renovation, combining contemporary interiors and historic charm. An excellent choice for a large group of friends or family, there's plenty of space to spill out and feel at home here. Cool off from the Tuscan sun in the infinity pool. Put to use the vast, chef-worthy kitchen (we're talking two dishwashers, two ovens, and some) for a big dinner party – a private chef is bookable for fine dining. Or keep things easy and fire up the barbecue or pizza oven outside as breath-taking views of the valley spread out before you – best seen beneath the pergola at sunset with a glass of something chilled. And on chiller nights, hunker down beside the fireplace with a good book – there are two living rooms to choose...More Details


    • Booked Available
    House • 14 People • 6 6
    From
    2,739 /night
    Min Stay 4 nights


    Siena, Italy 

    € 2,739 /Night (minimum stay 4 nights)
  • Swimming Pool
    Air Conditioning
    WiFi

    Farmhouse Modern


    Built in the eighteenth century, this former farmhouse combines rural living with the best of the modern world. Boasting sweeping views of the Val D’Orcia from the infinity pool, we can’t imagine a more perfect place to hang out as the hot Italian sun makes its way across the horizon. Enjoy alfresco dining on the lush patio, fire up the pizza oven for an authentic Italian experience or prepare wonderful meals with ultra-fresh fruit and veg straight from the garden and the famous Chianti wine in the contemporary kitchen inside. Several living areas allow the group to spread out, and have all been immaculately styled and designed – think sleek fireplaces and dazzling modern art against white-wash wooden ceilings and exposed stone walls. Bedrooms are just as stylish and some come with direct garden access and luxurious free-standing tubs. If you want to keep on top of your fitness game, there’s a gym on the first floor with a glorious pict...More Details


    • Booked Available
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    House • 10 People • 5 5
    From
    2,626 /night
    Min Stay 7 nights


    Pisa, Italy 

    € 2,626 /Night (minimum stay 7 nights)
  • Swimming Pool
    Pets Allowed
    Air Conditioning
    WiFi

    A Glass of Brunello


    This rural, pet-friendly villa offers equal amounts of elegance and tradition. Accessed through an electric gate and up an avenue of olive trees, you'll enjoy privacy and tranquillity on the outskirts of Siena. The private pool is available seasonally, so may not be open in the colder months, but there are plenty of other features that make this home stand out. The spa comes complete with a hot tub and sauna, and every bedroom has its own ensuite bathroom. For that extra dash of luxury, your host can arrange a private chef for a memorable dining experience. *There is free parking on-premises for up to six cars – due to the location of this home, we recommend hiring a car to make the most of your stay*Your host can provide a travel hot upon request, and a high chair and baby bath are also available – your host can also give babysitter recommendations*This home is spread over three floors with no internal lift, so may not be the best cho...More Details


    • Booked Available
    House • 46 People • 18 13
    From
    2,615 /night
    Min Stay 7 nights


    Colle di Val d'Elsa, Italy 

    € 2,615 /Night (minimum stay 7 nights)
  • Swimming Pool
    Pets Allowed
    WiFi

    Antico Borgo San Lorenzo


    "Antico Borgo San Lorenzo", 25-room cottage 650 m2 on 2 levels. Object suitable for 39 adults + 6 children. Spacious, fully renovated, very comfortable and tasteful furnishings: living/sleeping room with 1 double sofabed, dining table, kitchen corner and satellite TV. Exit to the terrace. Open living/sleeping room with curtain with 1 bed (80 cm), 1 double bed, open-hearth fireplace, dining table, kitchen corner, bath/shower/bidet/WC, double hand-basin and satellite TV. Exit to the terrace. Living/sleeping room with 1 double sofabed, open-hearth fireplace, dining table, kitchen corner and satellite TV. Exit to the terrace. Living/sleeping room with 1 sofabed, open-hearth fireplace, dining table and kitchen corner. Exit to the terrace. Living/dining room with dining table, kitchen corner and satellite TV. Living/sleeping room, on 2 levels with 1 double bed, dining table, kitchen corner, bath/bidet/WC and satellite TV. Living/dining room. ...More Details


    • Booked Available
    House • 13 People • 7 8
    From
    2,596 /night
    Min Stay 1 night


    Florence, Italy 

    € 2,596 /Night (minimum stay 1 night)
  • Swimming Pool
    Pets Allowed
    Air Conditioning
    WiFi

    Nature's Abundance


    Amid the olive trees of a private Tuscan estate, this home delivers an abundance of Italian charm. Dating back to the 1400s, you’ll be welcomed by a wonderful sense of character along with a range of comforts – including a private pool, hot tub and elegant rooms. Other highlights include the estate wine and olive oil, the nearby tennis courts and the open-air theatre held through the summer months (in the nearby woodland). It’s worth noting the grounds are shared with two neighbouring homes, but it still feels refreshingly private. You’ll also find this is a great base from which to explore the region – from here it’s just a forty-minute drive to Florence. *Please note some areas of the estate are shared with the neighbouring residents. *The owners offer a complimentary welcome dinner for your arrival – speak to your host to arrange the timing. *Housekeeping is included in your stay for two days per week (except Sundays and festivities...More Details


    • Booked Available
    House • 11 People • 6 5
    From
    2,501 /night
    Min Stay 1 night


    Florence, Italy 

    € 2,501 /Night (minimum stay 1 night)
  • Swimming Pool
    Air Conditioning
    WiFi

    Vineyards - Vines


    Only thirty minutes away from Florence, this home is nestled on a 16th-century private estate, where a shared bistro and tennis courts await. Comprised of a main villa and a separate cottage, the traditional interior design offers cosy fireplaces for all seasons. Whether business calls or you enjoy reading for pleasure, we especially love the library workspace. For your downtime in sunny Tuscany, the pool and alfresco dining table encourage outdoor living. Fancy more day trips? Arezzo and Siena sit within driving distance. *This home consists of a main villa and a separate cottage.\n *At full occupancy, one guest will be sleeping on the sofa bed in the sixth bedroom.\n *This home is located on a historic estate with free private parking. The reception, bistro, and tennis courts are shared with your neighbours.\n *If you're travelling with little ones, your host can provide a cot and high chair for free.\n *The swimming pool isn't fence...More Details


    • Booked Available
    House • 10 People • 5 4
    From
    2,452 /night
    Min Stay 7 nights


    Tuscany, Italy 

    € 2,452 /Night (minimum stay 7 nights)
  • Swimming Pool
    Air Conditioning
    WiFi

    Pool Of Honey


    Enjoy the verdant countryside of Tuscany in this beautiful home, fit with a lush garden – perfect for spending hours outdoors with your loved ones. Take a dip in the refreshing pool under the Italian sunset or rest on a sun lounger with your new favourite book found in the extensive library included with the villa. If the weather isn't on your side, then head into the home to find an extra indoor pool – the cool water is fantastic after you've taken part in an energising workout in the at-home gym. There's plenty of space for leisurely activities too such as sitting in front of the contemporary fireplace while you socialise with your loved ones, or heading upstairs to stretch out on the sofa in front of the TV. For the competitive members of your family, they'll love spending time at the pool table in the communal space. Adventure outdoors to find a beach within driving distance (10 minutes) for an afternoon in the sun by the sea or at ...More Details


    • Booked Available
    House • 20 People • 9 9
    From
    2,430 /night
    Min Stay 3 nights


    Siena, Italy 

    € 2,430 /Night (minimum stay 3 nights)
  • Swimming Pool
    Pets Allowed
    Air Conditioning
    WiFi

    Citrus Pavillion


    Overlooking vineyards, olive groves, and ancient oak forests, this collection of restored farmhouses offer the ultimate relaxed country retreat. With a refreshingly refurbished interior, saltwater infinity pool, bubbly outdoor jacuzzi, private spa and gym, and enough alfresco dining opportunities to shake a stick at, we are positive that this home offers something for each and every guest. Enjoy poolside sunbathing on plush sun loungers, before taking a dip in the cool, refreshing waters. Mornings are the perfect time to cuddle up on the veranda with a mug of something warm, looking out over rolling hills and lush vistas as the sun begins to warm your day. When the day is just too good to be spent at home, take a walk through the Tuscan countryside, before heading to Radda to sample some of the most refreshing wine and cuisine Chianti has to offer. * Due to the location of this home, we recommend hiring a car to get the most out of you...More Details


    • Booked Available
    House • 8 People • 5 6
    From
    2,313 /night
    Min Stay 2 nights


    Grosseto, Italy 

    € 2,313 /Night (minimum stay 2 nights)
  • Swimming Pool
    Air Conditioning
    WiFi

    As Free As The Sea


    Perched on a cliffside on the edge of Monte Argentario, the sunset views from this home are sublime. From the dining table on the terrace, you can gaze out over the sea and there are plenty of seating nooks in the shade. The real highlight is the private staircase leading down the cliffside to a rocky swim platform set up with loungers and parasols. Just remember, it’s quite a climb back up to the villa. The living room is huge, so big groups will feel at home here, and a wall of windows shows off the sea view inside. Tiles in the bathrooms might be a little garish for some, but who cares when the outside space comes with that view. *While not all of the bedrooms and bathrooms are photographed, expect the style and quality to be consistent with the rest of the home.*This villa has a private staircase to the sea, but there are quite a lot of stairs to the bottom and it's a rocky shore rather than a sandy beach.*A stay here includes a da...More Details


    • Booked Available
    House • 20 People • 11 11
    From
    2,241 /night
    Min Stay 1 night


    Tuscany, Italy 

    € 2,241 /Night (minimum stay 1 night)
  • Swimming Pool
    Air Conditioning
    WiFi

    The Magnolia Oak


    This magnificent home stands proud amongst a lush oak forest, with three separate houses and a large private pool. The decor is traditionally Tuscan, and there's a rooster that crows each morning, giving you a taste of countryside life. With multiple terraces and expansive gardens, there's more than enough outdoor space. You'll need a car here, though – the home is reached by a winding private road, and the location is ideal for exploring Tuscany's Archipelago, Belgheri's vineyards, sandy beaches and the city of Pisa. *Not all bedrooms and bathrooms are photographed, but we expect consistency in style and quality throughout this home. *There is private on-site parking for up to five cars here. Due to the location, we highly recommend hiring a car here. *Your host can provide a cot and high chair for free. *There is bed space for up to twenty-five guests here, but the maximum guest count is still twenty. *This home is spread over three ...More Details


    • Booked Available
    House • 18 People • 9 9
    From
    2,219 /night
    Min Stay 1 night


    Arezzo, Italy 

    € 2,219 /Night (minimum stay 1 night)
  • Swimming Pool
    WiFi

    Lavender - Lemons


    Amid the rolling hills and verdant countryside of Tuscany, this home delivers rustic Italian charm and idyllic views. Inside, the rooms unfold across three floors in the main house and two floors in the adjoining annexe – providing an abundance of space and a wonderful sense of character. Outside, the garden lends itself perfectly to lazy days by the pool (open seasonally) and long soaks in the heated jacuzzi. You will need a car to get around here, but it's just 6 kilometres to the nearby town of Ambra (don’t miss the weekly market), plus it’s also within easy reach of Siena, Arezzo, and Cortona. *While not all of the rooms are photographed, expect the style and quality to be consistent with the rest of the home.\n *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 for up to five cars.\n *The main house is spread across three floors while the annexe (with two d...More Details


    • Booked Available
    House • 16 People • 11 9
    From
    2,205 /night
    Min Stay 5 nights


    Florence, Italy 

    € 2,205 /Night (minimum stay 5 nights)
  • 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 same ...More Details


    • Booked Available
    House • 14 People • 6 6
    From
    2,089 /night
    Min Stay 4 nights


    Siena, Italy 

    € 2,089 /Night (minimum stay 4 nights)
  • Swimming Pool
    Pets Allowed
    Air Conditioning
    WiFi

    Casa Rossa


    Tucked away at the end of a four-kilometre dirt road, Casa Rossa provides guests with complete privacy and serenity for a most relaxing stay in the rolling hills of the Valdichiana. Welcoming up to twelve guests, this is an excellent choice for a group of friends or a family gathering. Casa Rossa boasts a contemporary look that creates both a refreshing contrast to its rural setting and offers guests plenty of modern luxuries, from the sleek kitchen to the indoor fire pit. Step outside and make the most of the expansive lawn, large pool and outdoor dining set up. Although you're about an hour and a half from Florence, you can always create your own Bistecca alla Fiorentina on the barbecue. What a way to spend a vacation. *The fireplace here is just for decoration. You won't be able to use it during your stay. Air ConditioningBarbequeBathtubCentral HeatingDishwasherDryerElectricity AdaptorsEspresso MachineFreezerFridgeGardenHair DryerH...More Details


    • Booked Available
    House • 11 People • 6 7
    From
    2,075 /night
    Min Stay 1 night


    Siena, Italy 

    € 2,075 /Night (minimum stay 1 night)
  • Swimming Pool
    WiFi

    Olive Garden


    Charming and traditional, this Tuscan villa sits in a serene spot near San Casciano Dei Bagni, and is ideal for those looking to get away from it all and enjoy some relaxing days amongst nature. Featuring a main house and a separate annexe, this home is ideal for large groups who'd occasionally like to split up and enjoy more privacy. The interiors are dreamy and elegant, with a neutral colour scheme that invokes a sense of calm. This vibe carries through to the outside of the home, where you'll find a gorgeous private pool that you can soak in while you stare out at the stunning views that surround you here. *While the home can sleep up to twelve people, the maximum occupancy is eleven guests.\n *The house is made up of the main house and a separate annexe.\n *For those with reduced mobility, there's a ground floor bedroom and bathroom here.\n *The swimming pool isn't fenced. If you're bringing little ones, they'll need to be supervis...More Details


    • Booked Available
    House • 13 People • 7 4
    From
    2,072 /night
    Min Stay 3 nights


    Florence, Italy 

    € 2,072 /Night (minimum stay 3 nights)
  • Swimming Pool
    Air Conditioning
    WiFi

    Tuscan Glory


    A twenty-minute drive from Florence's historic centre, this villa on the outskirts of the city is an excellent option for group gatherings. Come summertime, the garden is an absolute dream. There's a private swimming pool (open from April to October), an alfresco dining area, and sweeping views of Bagno a Ripoli's rolling hills (best enjoyed from the second-floor balcony). Traditional character abounds inside, which some may find dated but we find charming. While the villa owner lives on-site, you'll have plenty of privacy here – not to mention ample amounts of space to make yourself at home. *The swimming pool is only available for use between 1st April and 30th October.*Though we think the traditional interiors here are charming, some may find them dated.*This home is spread over four floors. A lift goes from the ground level to the first floor. However, the second floor and basement laundry room are only reachable by stairs.*If you'...More Details


    • Booked Available
    House • 12 People • 6 6
    From
    2,020 /night
    Min Stay 1 night


    Siena, Italy 

    € 2,020 /Night (minimum stay 1 night)
  • Swimming Pool
    Pets Allowed
    WiFi

    On Tuscan Hill


    Tuscan charm abounds at this rustic villa near Sarteano. Even with dated interiors, every room here conveys cosiness – picture arched stone walls, wood and terracotta ceilings, book-lined shelves, and a traditional fireplace. Outside, dappled terraces, a football field, and a private swimming pool will keep both grown-ups and little ones entertained. What's more, the rural location puts you within striking distance of Tuscany's old-world villages and rolling hills. Sarteano and Cetona are just minutes away, while Perugia and Siena are about an hour's drive and make good options for day trips. *While not all bedrooms and bathrooms are photographed, we expect the style and quality to be consistent with the rest of the home. As this villa is traditionally decorated and somewhat dated, the design may not suit everyone's tastes.\n *There are two ground-floor bedrooms and bathrooms here, ideal for guests with limited mobility.\n *The pool is...More Details


    • Booked Available
    House • 14 People • 7 5
    From
    1,944 /night
    Min Stay 1 night


    San Casciano dei Bagni, Italy 

    € 1,944 /Night (minimum stay 1 night)
  • Swimming Pool
    Air Conditioning
    WiFi

    Serenity in the Hills


    Set amid the vineyards and olive groves of the Val di Chiana, this 18th-century home delivers the ideal setting for a rustic Italian retreat. From the peaceful garden and private pool to the shaded terrace and traditional rooms, every detail has been considered to bring ease and comfort to your stay. Daily housekeeping is included and you will receive a complimentary welcome dinner. It’s also family-friendly with children’s amenities available on request and plenty to explore in the surroundings. From here, it’s just 2 kilometres to San Casciano dei Bagni, while Montepulciano, Siena and Perugia are also within driving distance. *Due to this location, we recommend hiring a car to get the most out of your stay. There is also private parking.*Please note this home is spread across two floors. There are also steps leading down to the pool. *Daily cleaning is included in your stay. There is also a towel change twice per week and a weekly li...More Details


    • Booked Available
    House • 12 People • 6 7
    From
    1,872 /night
    Min Stay 1 night


    Siena, Italy 

    € 1,872 /Night (minimum stay 1 night)
  • Swimming Pool
    Pets Allowed
    Air Conditioning
    WiFi

    Peace in Tuscany


    With idyllic views stretching across vineyards, olive groves and rows of cypresses, it’s not hard to see why this home caught our eye. Dating back to the 18th-century, the house has since been restored into a restorative retreat – one that will leave you feeling refreshed from the moment of arrival. Outside, you can soak in the natural beauty while swimming in the pool or relaxing in the shade. It’s worth noting that some of the furnishings are a little dated, but you will find plenty of rustic charm and family-friendly rooms. Housekeeping is available for an additional fee and children’s amenities can be arranged on request. And for adventures further afield, it’s just 4 kilometres to Montepulciano, while Cortona and Siena are also within driving distance. *There is free private parking for up to four cars here.*Please note this home is spread across three floors. One of the bedrooms and bathrooms is adapted for guests with reduced mo...More Details


    • Booked Available
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