Montelupo Fiorentino

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Nestled among the vineyards and olive groves of Chianti, this canary-hued 13th-century villa offers sweeping views as far as San Gimignano. Once a noble hunting lodge, it’s been lovingly restored with vaulted ceilings, terracotta floors and gilded paintings – plus modern comforts like air conditioning and daily maid service. One bedroom is named after Julia Roberts, a former guest, but the standout is the tower room with its own rooftop terrace. Outside, lush gardens surround a private pool and shaded terraces perfect for summer lunches. You’re on a working estate with wine, olive oil and honey for sale. And with Florence, Siena and hilltop villages all within easy reach, this is your gateway to the best of Tuscany.

Lady Julia

This contemporary villa is a stunning base for an Italian escape. It’s just a sixteen-minute drive from San Gimignano, with a winery only ten minutes away. The villa looks out over the surrounding hills and boasts views of San Gimignano and its historic towers. The outside space is beautiful, with a heated infinity pool at its heart. There’s also a great spot for alfresco dining on the terrace. Inside, the villa is timeless. It’s comfortable and stylish, a beautiful home-from-home with all the amenities you could wish for – there’s even a sauna. 

Tuscan Time

Perfectly tucked into the Tuscan hills yet only a thirty-minute drive from Florence, this home balances peaceful seclusion with easy access to sightseeing. Here you can laze away the day in the garden and cool off in your own private pool. Inside, you’ll find the rooms are just as inviting with large windows that let in the light and a rustic Italian feel. There’s a full kitchen to cook meals and plenty of room to relax. Plus, the location is ideal with Greve in Chianti and San Gimignano (just to name a couple of Tuscan towns) all within easy reach.

A Chianti Cottage

If forest bathing is your thing, this converted riverside mill is just the ticket. Slap bang in the beautiful Tuscan countryside, the abode is surrounded by mature trees, olive groves and rambling woodland trails that lead to a secret waterfall. Inside the main house, there’s a rustic yet refined approach. Expect exposed stone and timber beams with plenty of modern conveniences to ensure your stay as fuss-free as possible. Plus, there’s a private apartment with a bedroom, kitchen and en-suite bathroom – ideal for holidays with extended family or friends. There are village restaurants and shops a short drive away in the Montalbano hills and Florence is only 20 kilometres away, so you can get your culture fix in the morning and be back by the pool in time for an afternoon swim followed by a glass of something chilled on the expansive terrace. 

Verdant Possibilities

This home is a haven of tranquillity in Tuscany. It’s surrounded by vineyards, olive groves, and forested hills, with beautiful valley views at every turn thanks to its hilltop setting. The villa – comprising two apartments – has been thoughtfully restored to bring together traditional Tuscan charm, character, and modern convenience. Look forward to original terracotta floors and exposed wood beams inside, and a beautiful swimming pool outside. Ask your host to arrange a private chef and enjoy alfresco feasts on the terrace. 

Tuscany Terracotta

Perched in the Florentine hills of Chianti, this lavish villa is a great base for a laid-back Tuscan getaway. Inside, there's a cosy double living room with a fireplace, and a big kitchen and dining room that’s made for family feasts. Outside, the patio overlooks an infinity pool and classic cypress-lined views – a solid spot for an evening aperitivo. When you’re ready to head out, you’re a short drive from the picturesque towns of Certaldo and Montespertoli, and within easy reach of Florence and San Gimignano. 

Tuscan Sunbeam

Surrounded by silvery olive trees and architectural Italian cypresses, this traditional Tuscan farmhouse's bucolic setting would make even the Mona Lisa grin from ear to ear. Out and about, the birthplace of Leonardo Da Vinci is just down the road. If you prefer countryside pursuits, there's plenty of walks right on your doorstep. But you don't even have to leave the grounds for picturesque strolls – the large, sunny garden offers plenty to explore. Immerse yourself in your holiday read by the pool, or sit on one of the comfy outdoor sofas under an umbrella, listening to birdsong. With its charming wicker lampshades, wooden beams and window shutters, along with terracotta and terrazzo flooring, this home is full of character and warmth. On chillier nights, gather around the fireplace, flanked by vintage wine barrels, with a glass of Sangiovese wine in hand, and let the conversation flow. Whatever the season, like a fine work of art this joyful place will always delight. 

Luogo Gioioso

Enchanting doesn't even begin to describe this old farmhouse in the heart of Tuscany. At first glance, we were captivated by the apple red shutters, ivy-clad stone walls and serene country setting, but once we stepped inside, we fell even more in love with the romantic, welcoming and rustic interior. Wooden ceilings adorned with beams, traditional antique furniture, elegant bedrooms – this home has charm in abundance, and, what's more, there's plenty of space to spread out and get comfortable. 

Our favourite part was the pretty garden. Day or night, the beautiful views across the hills paint the perfect backdrop for your stay. Dig into alfresco meals underneath the shady pergola and savour a glass of wine as the day slowly fades on the outdoor sofa – your host leaves a local bottle of vino, fresh flowers and a cake for you to enjoy. Once the chill sets in, gather around the brick fire pit and enjoy a laughter-packed evening underneath the starry sky.

This home is within easy reach of Florence (thirty-five minutes), Siena (fifty minutes) or San Gimignano (forty minutes) when you fancy a change of scenery. Although there aren't a lot of eateries within walking distance, there are picturesque hiking and biking routes to explore and Poppiano Castle – now a vineyard and winery – is just a short stroll away.

Vintage Vines

Located near Montaione, this farmhouse offers a truly authentic Tuscan experience. Outside, the private garden has a pool for cooling off from the sun, and there’s a gazebo too. Plus, there’s a pizza oven and barbecue for alfresco dining. We love the stunning countryside views as well. Inside, the traditional interiors are homely, and there are more vistas from the bedroom windows. And, when you want to explore, this home is only a thirty-minute drive from San Gimignano and Volterra.

Tuscan Fields

Just a stone's throw away from Leonardo da Vinci’s birthplace, you’ll find this villa, surrounded by a small garden and beautiful views of the Tuscan countryside. There’s a shaded terrace, private pool and sundeck here to enjoy the Italian sun. Inside, there are plenty of character features and a mix of antique and modern furnishings, as well as more vistas from the bedroom windows over the landscape. When you feel like exploring, the Casa Natale di Leonardo museum is within walking distance, while the medieval town of Vinci is a short drive away.

Leonardo's Place

Arriving along a cypress avenue to a neoclassical villa in the heart of Empoli, you'd be forgiven for thinking you'd stepped into another century. The early 1900s architecture holds up beautifully – marble interiors, original detailing, and a grand staircase that connects four floors with quiet ceremony. Outside, sweeping parkland wraps the villa in seclusion, while the heated pool and glazed veranda mean long afternoons whatever the weather. A basement wellness area with a Turkish bath adds downtime potential. Piazza Farinata degli Uberti, with its classic Tuscan street life, is a twelve-minute walk away.

Marble Empoli

Pack your bags and make your way to this beautiful hideaway in the San Miniato region in Italy. Enter through the gates and up the grand, stone-paved driveway to a peach-orange typically Tuscan villa with wooden shutters. You’ll immediately want to drop everything to explore the green expanse, jump straight into the infinity pool and stretch out to catch some rays on the plush outdoor armchairs. High-beamed ceilings, arched entryways, terracotta floors and tiled bathrooms give the sense of traditional Italy. This is the kind of home where chandeliers light the formal dining room, baths come with claw feet, and fireplaces are crowned with antique trinkets. This is the perfect opportunity to try your hand at pizza making with the kitchen’s wood-burning oven, and there’s an old-fashioned pasta maker in the alcove for an Italian feast like nonna used to make. Show off your culinary skills as you gather around for a meal at the long, wooden table under the shaded terrace, where views over the rolling Tuscan countryside pair perfectly with a bottle of local red.

Book a stay in one of the best homes in Montelupo Fiorentino.

We selected the 3816 homes worth renting in this location

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Home spotlights in Montelupo Fiorentino

LADY
JULIA

TUSCAN
TIME

A CHIANTI
COTTAGE

We've selected the top 3% homes in Montelupo Fiorentino.

Most popular homes in Montelupo Fiorentino.

Verdant
Possibilities

Tuscany
Terracotta

Tuscan
Sunbeam

Luogo
Gioioso

Vintage
Vines

Tuscan
Fields

Leonardo's
Place

Marble
Empoli

Verdant
Possibilities

Tuscany
Terracotta

Tuscan
Sunbeam

Luogo
Gioioso

Vintage
Vines

Tuscan
Fields

Leonardo's
Place

Marble
Empoli

Tales of
Tuscany

Check rates and availability for Montelupo Fiorentino.

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Frequently Asked Questions

Book a stay in one of the best homes in Montelupo Fiorentino.

We selected the 3816 homes worth renting in this location

Home spotlights in Montelupo Fiorentino

LADYJULIA

TUSCANTIME

A CHIANTICOTTAGE

We've selected the top 3% homes in Montelupo Fiorentino.

Most popular homes in Montelupo Fiorentino.

VerdantPossibilities

TuscanyTerracotta

TuscanSunbeam

LuogoGioioso

VintageVines

TuscanFields

Leonardo'sPlace

MarbleEmpoli

VerdantPossibilities

TuscanyTerracotta

TuscanSunbeam

LuogoGioioso

VintageVines

TuscanFields

Leonardo'sPlace

MarbleEmpoli

Tales ofTuscany

Check rates and availability for Montelupo Fiorentino.

Book with Plum Guide.

Frequently Asked Questions

Can I see the best in Montelupo Fiorentino?

LADY
JULIA

TUSCAN
TIME

A CHIANTI
COTTAGE

Verdant
Possibilities

Tuscany
Terracotta

Tuscan
Sunbeam

Luogo
Gioioso

Vintage
Vines

Tuscan
Fields

Leonardo's
Place

Marble
Empoli

Verdant
Possibilities

Tuscany
Terracotta

Tuscan
Sunbeam

Luogo
Gioioso

Vintage
Vines

Tuscan
Fields

Leonardo's
Place

Marble
Empoli

Tales of
Tuscany