San Casciano in Val di Pesa

We selected the [listingCount] homes worth renting in this location

Book a stay in one of the best homes in [destination]

Set close to the Chianti town of Tavernuzze and with postcard-perfect Florence just a short drive away, the location of this traditional villa is spot on. Perfect for a multi-generational family getaway, along with the main house, there is an annexe en-suite bedroom – perfect for guests looking for extra privacy. It’s worth noting that the homeowner and their dog live on the wider grounds, and the family may occasionally use the pool. But those terraces with a pizza oven and built-in barbecue are all yours for alfresco evening meals. Time it right, and you’ll be rewarded with magnificent sunsets over the surrounding vineyards and cypress trees. 

Umberto Hills

Elegant and unique, this home makes for an excellent base in Tuscany. It’s in the village of Impruneta on the outskirts of Florence, surrounded by countryside, olive groves and vineyards – it also borders the Chianti Classico region. The centre of Florence is only 13 kilometres away, making day trips a breeze. The decor is traditional, with antiques at every turn, so it may not suit everyone. But for a break to Italy that feels a little like stepping back in time, it’s a great choice. 

The Falling Stones

Surrounded by olive groves and vineyards, this dreamy abode is nestled right in the heart of the Chianti hills. It's coated with a sense of tranquility from morning til night, enhanced by the completely fenced 3 hectares of gardens which look out across the breathtaking scenery. 

That garden is where you'll spend most of your time. It's built around the luscious pool and cosy seating space, a dreamy spot that's made for alfresco dining. Next to the pergola is a picturesque arbor, decorated by rose plants, which is ideal for spending sleepy afternoons with a good book.

When you fancy shelter from the summer sun, the lavish interior lures you into a restful comfort. Lounge in front of the TV, with a film from the DVD collection, refreshed by a cool drink from the fridge. 

All that lolling around can prompt the will to explore the local scenery. San Casciano is just ten minutes away by car and showcases authentically Italian restaurants, shops and cafes. If you spread further afield, the vibrant city of Florence is less than forty minutes away.

Olive Vineyards

This apartment, overlooking the beautiful vineyards of Tuscany, is situated in a historic palace that dates back to the 14th century. The place is packed with character, from the arched brick ceilings and terracotta tiles, to the chandeliers and antique furnishings.  Outside, the neat terrace is the perfect place to come together for lunch. Pick your spot at the table as tasty dishes are passed around and glasses are topped up with Chianti. Slip into the hot tub on cool evenings, with your favourite beverage in hand as a purple dusk falls across the landscape. And when it’s time to wind down, bedrooms strike a balance between elegance and comfort, so you’re guaranteed a restful night’s sleep. You’ll find this home in the small village of Marcialla, where family-run restaurants offering the very best of Tuscan cuisine are minutes from your doorstep. If you’d like to explore further afield, take to forty-minute drive into Florence for its world-famous sights – the iconic Galleria dell'Accademia, Duomo and Uffizi gallery await. 

Glass of Chianti

In a sleepy town in Tuscany, this breathtaking apartment is a unique find. Set in a former palazzo, it boasts classical Tuscan features like high ceilings, traditional archways, and a grand red brick exterior. Neutral colours inside contrast with the spectacular frescoed walls. We love the Rococo-style cherub fresco above the bed, lending the room a celestial aura. There is plenty of space to relax in the large open plan living area, and the fully stocked kitchen is perfect for practising your Italian home cooking. 

Certaldo Alto is a charming walled Medieval town, home to winding cobbled streets, picturesque churches, family run restaurants, and sprawling views of the verdant Tuscan countryside. It is 35km from Florence, making a day trip to the city easy. While you are there, be sure to sample some of the excellent wines from the region. After a day of exploring, kick back on the sofa in your opulent living room, before retreating to the serene calm of the bedroom for a perfect night’s sleep. With its romantic setting and unbeatable location, this would be the perfect getaway for couples. 

Fairytale in Fresco

Wine connoisseurs will appreciate the location of this rustic Tuscan farmhouse in the Chianti hills. It's surrounded by countryside views, vineyards and olive groves and has its very own tranquil garden – where you'll find a hot tub and plenty of outdoor seating for alfresco dinners and drinks. There's also a long dining table in the large living and dining area and plenty of quiet corners for curling up with a book. You'll find the quaint village of Impruneta a five-minute drive away, where you can sample local food and drink or tour some of the local vineyards. For a full day out, you can drive to Florence in half an hour.

Terracotta Jewel

For panoramic views of olive groves, vineyards and Tuscany's trademark landscapes, this restored country house tucked away in the Chianti region will do the trick. Surrounded by a hectare of beauty, easily admired from various seating areas and a private pool with a jacuzzi, this property offers a peaceful retreat for the whole family. And given the extra guest house bedroom – with its own kitchenette and living area – you can request, it has space for everyone too. There are many traditional features like terracotta tiles and beamed ceilings, but our favourite is the pizza oven outside. Florence and its renaissance art lie thirty minutes away.

La Dolce Spiaggia

Located on a hilltop in Florentine Chianti, this elegant, aristocratic home has glorious vistas over the surrounding hills, covered with vineyards and olive groves. It sits within a renowned wine estate producing excellent quality wines, which you can taste in the medieval cellar situated in the basement. The villa has a manicured lawn with a lovely swimming pool, a tennis court and a five-a-side football pitch to keep everyone entertained. Get some shade under the centuries-old pines and cedars of Lebanon, or pick some lemons and herbs for a G&T.

Inside, a grand staircase in pietra serena, a grey sandstone used extensively in Renaissance Florence, makes a stunning feature. Classical sculptures, opulent chandeliers and interesting artworks adorn the living spaces. After creating a Tuscan feast in the kitchen, entertain your guests at the piano. We adore the countryside views that stretch towards the centre of Florence and the towering dome of Brunelleschi from the two turrets, connected by a panoramic roof terrace.

This home is just a four-minute drive from Impruneta, a town renowned for its terracotta products and excellent red wine. Or head to historic Florence, where you'll find art masterpieces and beautiful renaissance architecture. For golf lovers, the Golf Club Ugolino is a fifteen-minute drive away. At this home, it's easy to create unforgettable holiday memories.



An Ode To Wine

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 time boasting all the modern comforts to make your stay here a comfortable and relaxing one. Wonder around the opulent rooms and find a place to kick off your shoes and unwind –  why not choose the main salon with a cosy fireplace? The country-style kitchen invites you to create delicious meals which can be enjoyed in the company of your family and friends at the elegant dining table. 

For a night of sweet dreams head upstairs where you’ll have a choice of eleven bedrooms – two of which are situated in a mezzanine – and all of which offer plush comfort and stylish elegance. Wake up well-rested and enjoy the fresh breakfast prepared for you. You can also stay on top of your fitness goals with a workout at the private gym.

Whether you’re here to enjoy a family get-together, a special event, or simply a relaxing holiday with your loved ones – you could hardly wish for a more special setting. Should you wish to explore beyond the walls of your castello, the breathtaking city of Florence is a mere half an hour by car, and the surrounding countryside offers countless opportunities for hiking and cycling while you discover the charming villages, lost in time. 

The Gem of Tuscany 

Enjoy a tranquil Tuscan getaway at this wisteria-draped villa, which has been beautifully converted from a historic mill. The river that once powered the mill passes nearby, the sound of flowing water adding to the sense of serenity as you gaze across the garden’s sun-kissed greenery or lounge beside the pool. Indoors, the rooms are cosy and characterful, where original details like exposed brickwork and timber beams have been paired with modern comforts. We wouldn’t blame you if you stayed right here for your entire holiday, but this villa is also an ideal springboard for seeing more of Tuscany’s treasures, from romantic vineyards to Renaissance towns.

Wisteria & Wine

Overlooking the rolling green hills of Chianti, this apartment sets the tone for a blissful Italian stay. Occupying the first floor of a private residence, the rooms are perfect for families and groups in search of timeless Italian charm. There’s a private terrace for evening drinks and a shared saltwater swimming pool as well as a barbecue area for alfresco dining. You will need a car to get around here, but private parking is available and it’s just a short drive to Florence and Siena. 


The Josephine  

This refurbished stone tower including wooden beam ceilings and terracotta details is in a gorgeously remote location close by to the hamlet of Tignano. The rustic interior makes you feel a million miles away from the hustle and bustle of your usual daily routine. 

Snuggle up on the sofa next to the antique stone feature wall with a new book or head outside to the garden to while away the afternoon by the glimmering pool. Take a swim in the refreshing water whilst overlooking the beautiful panoramic landscape, followed by a lush glass of red on the sun loungers – we love the details of the vines on the beams, giving that verdantly overgrown foresty feel.

The amazing city of Florence is only a drive away, the perfect destination to discover unique hidden gems and delicious eateries to sample some of the finest Italian cuisines. Visit historical landmarks and soak up the culture at the wide variety of museums found around the city. Tuscany is also full of some of the most delightful scenery, including authentic Italian vineyards.

In the evening, grill up a storm on the barbeque and enjoy an alfresco homecooked meal at the outdoor dining table while you watch the sunset. Why not take a dip in the pool under the amber glow? Finish off the day by heading back inside to watch a movie on the TV – you'll soon fall asleep to dream of the charming Tuscan hills.

Tower Of Vines

United Kingdom luxury cottages

England luxury cottages

Wales luxury cottages

Scotland luxury cottages

Edinburgh airbnb alternatives

York airbnb alternatives

Cornwall luxury cottages

Cumbria luxury cottages

Devon luxury cottages

Dorset luxury cottages

Kent luxury cottages

Norfolk luxury cottages

Northumberland luxury cottages

Pembrokeshire luxury cottages

Somerset luxury cottages

Suffolk luxury cottages

The Cotswolds luxury cottages

Yorkshire cottages

United Kingdom

London airbnb alternatives

London luxury aparthotels

London luxury serviced apartments

London luxury short stay rentals

London luxury vacation rentals

London

Paris airbnb alternatives

Paris luxury aparthotels

Paris luxury short stay rentals

Paris luxury vacation rentals

Paris

Los Angeles airbnb alternatives

Los Angeles luxury vacation rentals

New York airbnb alternatives

New York luxury short stay rentals

New York luxury vacation rentals

Joshua Tree airbnb alternatives

Palm Springs airbnb alternatives

Palm Springs luxury vacation rentals

San Diego airbnb alternatives

United States

Italy luxury villas

Rome airbnb alternatives

Rome luxury vacation rentals

Milan airbnb alternatives

Florence airbnb alternatives

Venice airbnb alternatives

Apulia Luxury Villas

Sicily luxury villas

Tuscany luxury villas

Lake Como

Sorrento airbnb alternatives

Amalfi Coast airbnb alternatives

Italy

Spain luxury villas

Barcelona airbnb alternatives

Barcelona luxury aparthotels

Barcelona luxury vacation rentals

Madrid airbnb alternatives

San Sebastian airbnb alternatives

Canary Islands luxury villas

Costa del Sol luxury villas

Ibiza luxury villas

Malaga airbnb alternatives

Mallorca luxury villas

Marbella luxury villas

Spain

Portugal luxury villas

Lisbon airbnb alternatives

Porto airbnb alternatives

Algarve luxury villas

Madeira luxury villas

Portugal

Greece luxury villas

Athens airbnb alternatives

Crete luxury villas

Corfu airbnb alternatives

Mikonos airbnb alternatives

Rhodes luxury villas

Santorini airbnb alternatives

Greece

Berlin airbnb alternatives

Cape Town

Copenhagen airbnb alternatives

Dubai airbnb alternatives

Tel Aviv airbnb alternatives

Barbados luxury villas

Cyprus luxury villas

French Riviera luxury villas

Other

Top Destinations

Destinations

San Casciano in Val di Pesa Accommodation

San Casciano in Val di Pesa Accommodation for Groups

San Casciano in Val di Pesa Airbnb Alternatives

San Casciano in Val di Pesa Aparthotels

San Casciano in Val di Pesa Boutique Hotel Alternatives

San Casciano in Val di Pesa Corporate Housing

San Casciano in Val di Pesa Cottages

San Casciano in Val di Pesa Dog Friendly Rental Accommodation

San Casciano in Val di Pesa Family Friendly Hotel Alternatives

San Casciano in Val di Pesa Family Friendly Rentals

San Casciano in Val di Pesa Holiday Homes with Hot Tubs

San Casciano in Val di Pesa Holiday Rentals

San Casciano in Val di Pesa Homes with Swimming Pools

San Casciano in Val di Pesa Hotel Alternatives

San Casciano in Val di Pesa Long Stay Rentals

San Casciano in Val di Pesa Luxury Rentals

San Casciano in Val di Pesa Monthly Rentals

San Casciano in Val di Pesa Pet Friendly Rental Accommodation

San Casciano in Val di Pesa Self-Catering Apartments

San Casciano in Val di Pesa Serviced Apartments

San Casciano in Val di Pesa Short Stay Rentals

San Casciano in Val di Pesa Unique Homes

San Casciano in Val di Pesa Vacation Rentals

San Casciano in Val di Pesa Villas

Types

Book a stay in one of the best homes in San Casciano in Val di Pesa

We selected the 3770 homes worth renting in this location

Who's coming along?

Home spotlights in San Casciano in Val di Pesa

We selected the top 3% holiday homes in San Casciano in Val di Pesa

Most popular homes in San Casciano in Val di Pesa

Check upcoming rates & availability for San Casciano in Val di Pesa

Frequently asked questions