There's a reason Tuscany is one of the most visited regions in Italy. Its pastoral landscapes, rolling hills and sunflower fields dotted with historic hilltop towns are straight from a postcard. Tuscany is also one of Italy's best wine areas, home to some of the most scenic vineyards in the country. Some of our favourites are found in Chianti, Montalcino and Montepulciano. Our travel experts here at Plum Guide know Tuscany very well, and have spent plenty of time tasting their way through the region (strictly for research purposes, of course). If you're heading out here on a wine-tasting holiday, nothing beats staying close to a vineyard. After all, what can top picturesque views and private wine tastings? Keep reading for the very best Airbnb alternatives in Tuscany near a vineyard.
Grand Rusticana
Grand Rusticana, Plum Guide home in Tuscany
Set among the olive groves and vineyards of the Chianti region, this villa is the right choice for those who like historic homes. With its foundations dating back to the 13th century, you’ll spot plenty of period features inside, from exposed beams and large fireplaces to the vaulted stone ceiling. There are six luxurious bedrooms to choose from – some of which offer plush canopy beds fit for royalty. While the interiors are stunning, it’s the grounds which are really something to write home about. Whether you’re cooling off in the private swimming pool, strolling through the flower-filled gardens or sipping wine in the shade, you’ll be treated to breathtaking panoramas of the lush Tuscan countryside. If you’ve consumed a little too much pasta (we’re not judging), there’s both a tennis and boules court should you feel like stretching your legs, as well as plenty of wine-tasting experiences just a short drive away.
Chianti Cheers
Chianti Cheers, Plum Guide home in Tuscany
Searching for Airbnb alternatives in Tuscany near a vineyard? It doesn’t get better than this apartment, which boasts a vineyard right on your doorstep. Located on a family-run farm in Montespertoli, this rustic abode is the perfect choice for a rural getaway. While most of our Chianti villas are quite large, this one is perfectly sized for a small family or two couples. We like that one of the bedrooms opens up onto the tiny private garden, so you can let the breeze in whenever you like. Spend long days roaming the countryside and the grounds, whether you choose to lace up the walking boots, go for an e-bike ride or take a classic Italian Fiat 500 for a spin. In the afternoon, arrive back at your digs and pop open a bottle of the farm’s very own wine, best enjoyed on the shaded terrace as you watch the sun setting a golden glow over the hills.
Panzano Panoramas
Panzano Panoramas, Plum Guide home in Tuscany
As far as villas go, this one is hard to beat. It's surrounded by Panzano’s sprawling hills, a charming town in the heart of the Chianti wine region – and trust us, the 360-degree panoramas of Tuscany’s bucolic countryside speak for themselves. Our advice is to nab the luxe main bedroom, where you can admire the scenery without getting out of bed. It even leads out onto a terrace where you can savour a morning coffee before joining the rest of the group. We say group as there are seven bedrooms to choose from, so it’s an excellent option for large gatherings of family and friends. When you’re not making the most of your private Jacuzzi tub or whipping up meals in the high-spec kitchen, you’ll want to spend most of your time outdoors. A large pool, sprawling lawns, and alfresco dining areas make it perfect for outdoor living.
The Maestro’s Daughter
The Maestro's Daughter, Plum Guide home in Tuscany
Just outside Panzano, this home is everything we could've dreamed of in a Tuscan getaway. The first thing you'll lay eyes on as you arrive is the view – looking out over the rolling fields, it's almost as if you've stepped into a postcard. There are plenty of places to appreciate the vistas, whether from the swimming pool, the alfresco dining table or the more casual seating area in the shade. The home is equally spectacular inside, with luxe furnishings, rustic touches, and a hint of Italian elegance. After a day of exploring the captivating Tuscan countryside, come home and tuck into a delicious meal around the dining table, going over the best parts of the day. Although the sumptuous bedrooms will have you looking forward to going to bed each night (we particularly like the main bedroom with its four-poster bed and freestanding bath), you may want to fit in a pamper session in the sauna and Jacuzzi first.
Wrapped in Jasmine & Aloe
Wrapped in Jasmine & Aloe, Plum Guide home in Tuscany
This home really stands out on our list of Airbnb alternatives in Tuscany near a vineyard. You couldn’t ask for a better location, overlooking the breathtaking Val di Chiana valley dotted with wineries, thermal waters and medieval towns. While days out are just on your doorstep, the home’s delightful features make staying in equally appealing. We’ll start with the infinity pool and its telescopic closure system – close the transparent walls and roof and you have an ‘indoor’ pool accessible directly from the living room. And what a living room it is, with an open-plan layout, a sunken seating area and sliding doors beckoning the outside in. The lounge shares a space with a farmhouse-style kitchen, complete with a fireplace and long communal table designed for big Italian dinners. Outside, you and your loved ones can get the wood-fired oven going and create your own pizzas while sharing good wine and conversation by the alfresco dining area. Multiple annexes ensure everyone has their own space to retreat to after a long day.
Mellow Top
Mellow Top, Plum Guide home in Tuscany
Sleeping up to forty people, this beautiful countryside retreat is one of our best homes for large groups. Although there are ample communal spaces, you’ll still have plenty of privacy with bedrooms split between the main villa and six self-contained apartments. The interiors are what you’d expect from a Tuscan country home – think high beamed ceilings, arched doorways and exposed brick. It may be rustic, but the luxe finishings make it that much more special. Set between Florence and Siena, this is the ideal base for exploring Tuscany’s stunning Renaissance cities, as well as day trips to Panzano’s and Chianti's vineyards. When you don’t feel like getting out and about, the home offers plenty of opportunities to unwind and disconnect from the world, including a private spa to a large swimming pool and sun loungers in the shade. The toughest decision you’ll have to make here is choosing which one you’d like to enjoy first.
Honey & Fig
Honey & Fig, Plum Guide home in Tuscany
If you're surprising your other half with a wine-tasting getaway, this studio is the perfect love nest for you. You'll find it in the heart of Montalcino, a medieval hilltop town renowned for its Brunello di Montalcino red wine. Overlooking the Sangiovese vineyards, it has everything you could want in a romantic getaway – a cosy bedroom with a log burner, a barbecue and alfresco dining area for dinner under the stars, and a hot tub where you can enjoy a glass of wine with a view. The modern kitchen is kitted out for home cooking, but if you fancy some traditional Italian dishes, then you're just a short stroll from the town's main square, Piazza Garibaldi, home to an array of restaurants. Finish off strong with a trip to one of the local wineries – we recommend Enoteca Grotta del Brunello for one of the best wine-tasting experiences you've ever had.
Yellow Harvest Moon
Yellow Harvest Moon, Plum Guide home in Tuscany
When it comes to Airbnb alternatives in Tuscany near a vineyard, this farmhouse-style home is in a league of its own. The garden stretches over 6 hectares, with plenty of room for a walk through the vineyards and olive groves surrounding you. Even better are the fantastic views of the ancient town of Montepulciano, famous for its Vino Nobile red wine. Drink in the scenery from the pool or with a glass of wine in the hot tub. While you relax, kids will love how much lawn there is to run around and play ball games on, as will the four-legged members of the family. There’s plenty of room to socialise inside, with a large kitchen diner, formal dining room and seating area leading towards the terrace. It may not be the most luxurious home in our collection, but with such incredible views, we’re sure you’ll want to spend most of your time under the Tuscan sun.
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