Best Villas in Tuscany with Private Pools: Curated by Area & Style

This is a curated list of 19 villas in Tuscany with private pools, organised by area – from the Pisa-Lucca corridor in the north through Chianti and Arezzo in the centre, down to the Val d’Orcia in the south and out to the Tuscan coast.

I’ve spent extended time in Tuscany and have stayed in the Chianti countryside and the Val d’Orcia, so I know how much difference the right location makes to a trip here. 

The area section introductions below reflect that – each one gives you a genuine steer on what you’ll actually be able to do and see from each base, not just a description of the landscape.

Renting a villa with a private pool is, in my view, the best way to do Tuscany if you have a week or more. 

You get the countryside on your doorstep, a base to return to after day trips into the hilltop towns, and – on the days you don’t want to go anywhere at all – a pool, a view, and a very good reason to open the wine early.

19 Villas in Tuscany with Private Pools: Quick Overview

What is the best part of Tuscany to stay in?

The right area depends on what kind of trip you’re planning. Here’s a quick orientation before we get into the properties:

In short, you should consider the areas of:

• Northern Tuscany: to include the area around Pisa and Lucca
• Central Tuscany & Chianti: stretching from Florence to Siena and including towns like San Gimignano
• The Val d’Orcia: just south of Siena and including towns like Montepulciano, Montalcino and Pienza
• The Tuscan coast: consider the full stretch of coast, depending on your needs. North will give you access to city of Pisa, Elba island is a complete retreat and the Maremma offers unspoilt coastline.

Best villas in Tuscany with private pools by area

Northern Tuscany

The north of Tuscany is a little more mountainous than the rest of the region, and is also a little less visited than the rest of Tuscany. The city of Pisa and town of Lucca are, however, immediately recognisable names, so the area still does receive quite a bit of footfall. 

A well-placed villa with a private pool in the Pisa–Lucca corridor (they’re only about 20km apart) makes a convenient launch point for exploring both of these compact, character-rich cities.

As well, the Garfagnana valley (famed for its chestnuts and mushrooms) and the Mugello to the north of Florence, which was the original homeplace of the Medici family. Florence itself is also relatively close and can be reached by car or train from both cities in around an hour or so.

Villas in Lucca with pools

Olive Grove Luxury Villa near Lucca

This wonderful villa is the perfect choice for groups searching for luxe Lucca vacation rentals with pools. Located a mere 12 minute drive from the walled town of Lucca, the villa is nestled in the heart of the Tuscan countryside and is surrounded by olive groves.

This is a seriously well-appointed property – contemporary interiors, a large pool, and plenty of outdoor space for dining and unwinding. There is a large pool and ample space for outdoor dining, lounging and wine-sipping.

Sleeps: sleeps up to 8 people // 4 bedrooms // 4 bathrooms

Why you should book: 12 minutes from the walled town of Lucca, with generous outdoor space and interiors that feel genuinely luxurious without losing the Tuscan character of the property.

Design Villa with Pool, Lucca

If you’re after a villa with a pool near Lucca, this newly built holiday home fits the bill. Situated in a residential area just on the outskirts of Lucca, guests will be close to local restaurants and will be in the town centre in mere minutes if you hop in the car. 

The house is furnished with in a modern style, offering a contemporary retreat in which to luxuriate. The enclosed garden makes this a property worth considering if you are traveling with children, with good views of the back yard too from upstairs. There’s also a covered outdoor dining area and barbecue. 

Sleeps: sleeps up to 6 people // 3 bedrooms // 3 bathrooms

Why you should book: Just on the outskirts of Lucca, with a contemporary finish and an enclosed garden that makes it a sensible choice for families travelling with children.

Three Stone Cottages with Infinity Pool and Panoramic Views of Lucca

This Lucca villa with pool commands an extremely imposing perch, boasting fabulous views of the medieval town of Lucca below. Comprising three individual stone cottages (all part of the rental), its piece de resistance is the incredible infinity pool and its stunning vistas.

Views are not just limited to the pool, however, and there is an impressive outdoor set up. There are several separate areas for outdoor dining, including a stunning lavender-draped nook, along with a large eating space on a shaded terrace, that also comes with an outdoor kitchen and barbecue.

Sleeps: sleeps up to 12 people // 4 bedrooms // 5 bathrooms

Why you should book: Commanding views of Lucca from an elevated rural position, with extensive outdoor cooking and dining facilities that make self-catering here genuinely appealing.

Villas near Pisa with pools

Private villa Tuscany with pool near Private Villa with Pool near Pisa

Those searching for villas in Tuscany near Pisa will be delighted with this one. Located in a prominent position on the edge of the picturesque town of Calci (reachable on foot), the villa is surrounded by olive trees and vineyards.

The villa is completely independent, all rooms have a private bathroom and there is a large kitchen. There is also a rustic living room with a fireplace, a large garden and of course – a swimming pool.

The Villa is ideal for families and groups of friends who plan on exploring the region of northern Tuscany and Chianti. Nearby cities: Pisa is reachable within about 10 minutes, Lucca within about 20 minutes, Florence city within 50 minutes. At 2 km is a Certosa di Calci and its natural history museum.

Sleeps: sleeps up to 6 people // 3 bedrooms // 3 bathrooms

Why you should book: A well-positioned base for northern Tuscany – Pisa within 10 minutes, Lucca within 20, Florence within 50. Good for those who want to move around without covering too much ground each day.

Central Tuscany & Chianti

One of the two main areas (the other one being the Val d’Orcia) that brings visitors to the Tuscan countryside, Central Tuscany is a wonderful base to explore the province of Tuscany and some of its towns and cities from. 

The area is famed for Chianti wine, and the vineyards and estate cantinas along the SR222 are among the best reasons to be based here.

The area is verdant and lusciously green and I can still hear the melodic birdsong that I woke to each morning when I stayed in the area. 

On the edges of Chianti is the town of San Gimignano and its medieval skyscrapers, as well as the fantastically medieval city of Arezzo, the home of Renaissance artist and architect Vasari, who designed Vasari’s Corridor and the Uffizi in Florence. 

If it’s your first time visiting Tuscany, then I would probably start here, as you’ll get that quintessentially Tuscan experience that you are craving. 

Villas near Florence with pools

Luxury Villa with Infinity Pool and Views of Florence

Set in classic Tuscan countryside, this four-bedroom villa with a pool has been recently renovated and is just a short five-minute drive from the heart of Florence.

It is part of a 20 hectare organic farm, immersed in a natural environment of olive groves, fruit-trees and flowers. The villa has been newly renovated to the highest standards, preserving all its original features and character. 

The private infinity pool with wonderful views of Florence comes fully furnished, with day beds, loungers and a BBQ grill.

The outdoor area is equipped with a shaded dining loggia perfect for relaxing, al-fresco dining or having a barbecue. Surrounded by greenery and stillness, the gardens here set a calm, one-of-a-kind tone from the moment you arrive.

The village of Settignano is less than 1km away and can be reached on foot. It is home to 3 great restaurants/pizzerias and a number of other essential stores.

Sleeps: up to 8 people // 4 bedrooms // 4 bathrooms

Why you should book: an incredible choice if you’re looking for villas in Tuscany near Florence. You’ll be in central Florence in a jiffy, while also being immersed in a beautiful countryside location that offers easy access to Chianti. 

Rustic & Historic Villa near Florence (sleeps 18)

Rustic yet refined, this poolside villa in Tuscany has a story to tell. Once home to Marsilio Ficino, astrologer and educator to the Medici family, you’ll be staying in a piece of classical Italian history.

This villa is absolutely exquisite and is a wonderful choice if you’re searching for villas for rent in Tuscany near Florence that can hold a large group of people – this can take up to 18 guests. 

While this is a high-end stay, it hasn’t lost its local soul. Terracotta floors and wooden ceiling beams keep the feel distinctly Tuscan.

Rooms are spread across three separate houses at this Florence villa, but everything orbits around the large pool and striking outdoor lounge area that ties the whole place together.

Located on 27 hectares of private land in the Tuscan countryside and approached via a laneway flanked by cyprus trees, the city of Florence can be reached within 30 minutes.

Sleeps: up to 18 people // 9 bedrooms / 10 bathrooms

Why you should book: If you’re looking for Tuscany villas near Florence with pools and history that can cater for a large group

San Gimignano vacation rentals with pools

Converted Hayloft near San Gimignano

Those eyeing villas near San Gimignano will appreciate the setting here with its peaceful countryside spot with that classic Tuscan feel.

Housed in a former hayloft, this home wears its roots proudly with unmistakably details of stone walls, wood-beamed ceilings, and terracotta tiles underfoot—you’re left in no doubt as to what part of Italy you’re in!

It has a large terrace where guests can embrace outdoor living and dine outdoors, together with an incredibly idyllic pool. Set in the heart of Chianti, there are sweeping views of the rolling hills, vineyards and olive groves nearby. San Gimignano is also located a few minutes drive away.

Sleeps: sleeps up to 6 people // 3 bedrooms // 2 bathrooms

Why you should book: An idyllic country retreat for couples or small groups who want easy access to San Gimignano and the Chianti wine country around it.

Stone Barn Conversion near San Gimignano

In the hills just outside San Gimignano, this stone-built barn conversion is the kind of place that makes a holiday feel well spent. It is surrounded by nature and offers you the chance to relax in its private garden and enjoy the sweeping views over the surrounding area.

Inside, the style leans rustic, balanced by all the mod-cons that make a stay smooth and stress-free. It’s also wonderfully located if you plan on exploring the area of Chianti and slightly further afield, as it’s only 8km from the Siena/Florence dual carriageway.

You’ll also find shops with essential services nearby in the village of Ulignano, which is less than 2km away. 

Sleeps: sleeps up to 5 people // 2 bedrooms // 1 bathroom  

Why you should book: Classically rustic, well-priced for its size, and positioned within 8km of the Siena-Florence dual carriageway – which makes it one of the better-connected options on this list.

Villas near Arezzo with pools

Luxury Stone Villa above Arezzo with Valley Views

High above Arezzo, this quietly elegant villa sits among the hills, comes with a pool and wide-open stretching across the valley. Designed to highlight its historical character, the house pairs original stone walls with soft neutrals and natural fabrics that let the details shine.

In the main farmhouse there is a spacious kitchen with an Aga-style oven, glass fronted cabinets and vintage dining table, as well as spacious bedrooms and luxury bathrooms. 

There are also two separate apartments with smaller, well-equipped kitchens that pay homage both to their humble origins and to their sophisticated style. The master bedroom is relaxed and comfortable, with a gauzy bedspread and smart lighting making for a boutique stay.

Outside there is a children’s playground, a ping pong table, a hot tub and a Roman-style swimming pool surrounded by sun loungers that boasts incomparable views of the countryside below.

Sleeps: sleeps up to 12 people // 6 bedrooms // 8 bathrooms

Why you should book: the perfect balance of rustic and luxurious, this exceptional property is perfect for those looking for Arezzo province vacation rentals for a special occasion or family gathering. 

Apartment in Elegant Tuscan Villa near Arezzo

A smart choice for smaller groups, the two-bedroom apartment delivers the full villa experience in Arezzo, complete with a pool and plenty of space to unwind.

Found at the base of an elegant Tuscan villa, the apartment offers a well-rounded stay with everything in place for comfort and ease. Double bedrooms have a four-poster bed and there is also a lovely private outdoor space covered with loggias.

While not exclusive, the pool is shared only with guests from the villa’s four additional apartments—so it still feels peaceful and uncrowded. Among the amenities available to all guests are barbecues, a delightful swimming pool, a large garden area, a spa with sauna, and a rather sweet view of the valley and Chianti hills.

Also one for the wine lovers, the villa’s owner is from Valpolicella, from where he produces wines like Amarone and Ripasso. You can purchase these from the reception at reasonable prices and can compare to the local Tuscan wines!

Sleeps: up to 4 people // 2 bedrooms // 2 bathrooms

Why you should book: a great option for a couple or small group who want that Tuscany pool villa experience at a price that is suited to the size of their group. 

Siena & the Val d’Orcia

Val d’Orcia is a rich, green valley located in the south of Tuscany stretching between the provinces of Siena and Grosseto.

Time seems to move slower in this incredibly scenic area and the region has an extremely rich cultural heritage, as well as being an exceptional producer of fine wines in the form of Brunello di Montalcino and Vino Nobile de Montepulciano.

Home of amazing sunsets, the whole province itself is also a designated UNESCO World Heritage site. 

Towns to visit in order to sample these wines include their namesakes, respectively; the hilltop towns of Montalcino and Montepulciano.

Val d’Orcia is also home to a number of other ridiculously picturesque towns, although its jewel is arguably the town of Pienza, the Renaissance’s “perfect city” and its sweeping views of the gently undulating valley from its walls. 

Siena sits within the province and makes a natural day trip from any Val d’Orcia base – it’s covered in full in my one-day Siena itinerary if you want the detail on what to prioritise.

Villas near Siena with pools

Gorgeous Farmhouse near Siena (shared pool)

Don’t hold it against me for not sticking entirely to the brief with this charming farmhouse near Siena, where the pool is communal rather than exclusive to the villa. Still, the draw of this beautiful farmhouse is, however, just too good to pass over.

With seven individual units under one roof, this property near Siena suits everything from solo getaways to couples’ trips and can easily accommodate a larger group if needed.

You’ll still get all the benefits that a larger Tuscan villa would bring, while still retaining your own privacy and sticking within your budget. 

Interiors feature traditional Tuscan touches—weathered wood, stone, and sun-warmed colours—the apartment near Siena is a great way to experience both the city and the wider Val d’Orcia. Siena is 30 minutes away, Montalcino is on your doorstep, and Montepulciano is less than half an hour’s drive.

Sleeps: sleeps up to 3 people // 1 bedroom // 1 bathroom

Why you should book: perfect for a couple of want all the amenities of a larger villa, who want easy access to the Val d’Orcia’s most popular spots. 

Rolling in Olives: Villa with Pool and Views near Siena

Slightly north of Siena, on the edge of Chianti, this is a wonderful option for those looking for villas in Tuscany near Siena that let you dip into the Val d’Orcia and Chianti alike, with their distinct flavours and famously scenic towns.

At this villa for rent, you’ll be within easy reach of idyllic villages such as Castellina and Radda, while also being able to easily reach of Val d’Orcia hotspots like Montalcino, Pienza and Montelpulciano.

The pool comes with wide-open countryside views, while inside, stone archways and timber-beamed ceilings give the home a classic Tuscan feel.

Groups can make use of its numerous outdoor seating areas, set amongst both the Italian garden and a patio. There is also a barbecue that makes dining al fresco, surrounded by views, a real winner for this property.

Sleeps: sleeps up to 14 people // 7 bedrooms // 7 bathrooms

Why you should book: perfect for large groups searching villas for rent in Tuscany near Siena who want to do different things during their stay. In a beautiful location, it sits on a wonderful axis for exploring both Chianti and the Val d’Orcia.

Villas near Montepulciano Italy with pools

Sienese Farmhouse in the Shadow of Montepulciano

Podere Poggio al Sole is located only 2 km from Montepulciano and in fact sits in the town’s shadow, immersed in a hunting reserve. It has a 2-bedroom apartment with a large living room with comfy sofas and a fully equipped modern kitchen.

Recently renovated, the original building is a typical Sienese farmhouse from the 18th century, with renovations remaining sympathetic to this. There is also a large garden with deck chairs, sun beds, a BBQ and of course – an outdoor pool, which comes with spectacular views of the surrounding Orcia Valley.

Montepulciano is a fantastically medieval hilltop town with some great restaurants and is a wonderful base from which to explore the nearby towns of Pienza and Montalcino. 

Sleeps: sleeps up to 4 people // 2 bedrooms // 1 bathroom

Why you should book: if you’re looking for a relaxing vacation spent exploring the towns of the Val d’Orcia and whiling away hours by the pool, this is a fantastic base. 

Unique Villa in a Former Water Mill near Montepulciano

A former water mill turned into an exceptional holiday home, it’s a place where traditional character meets elevated comfort—perfect for a stylish stay in Tuscany.

This villa rental with pool is located amongst woodland and 1.5 acres of private grounds, offering complete privacy. There is a glorious, expansive pool perfect for sunbathing and lounging.

Expect a thoughtful mix of time-worn textures and polished details, where weathered wood meets plush fabrics and cosy, considered design. It’s easy to see the love and care that went into restoring this beautiful stone-built property and the personal taste of its owners through a mix of antique and custom pieces used to furnish throughout.

The home also boasts its own vineyards and guests can avail of some wine produced from the same. 

When you’re ready to trade the kitchen for a table out, the restaurants of Montepulciano are only five minutes down the road.

Sleeps: sleeps up to 14 people // 7 bedrooms // 8 bathrooms

Why you should book: an incredible choice for those searching for villas with pools near Montepulciano. A thoroughly special villa in southern Tuscany that is perfect for family reunions, or when privacy is desired.

Villas near Montalcino with pools

Farmhouse amongst Brunello Vineyards near Montalcino

Brunello di Montalcino is amongst the best wines in Italy – if not the world – and if a few days immersed in the vineyards where it’s produced sounds like your idea of a good time, this is the villa for it.

Just outside town but surrounded by countryside, this farmhouse is ideal for those seeking a Montalcino villa with privacy and offers complete tranquility for total relaxation!

The pool offers plenty of space for either catching some sun, or sitting in shade beside it and there is also a lovely sheltered area for dining al fresco. The owner can even arrange for a chef to drop in and cook for you or if you’d like to learn how to create some Tuscan dishes, a cooking lesson can also be arranged. 

You’ll have the chance to visit the owners’ own cellar, where they produce Brunello. If you are a real wine lover, they can host you at their main wine cellar by the Tenuta di Nozzole near Greve in Chianti, where we hold proper wine tastings.

Sleeps: sleeps up to 6 people // 3 bedrooms // 2 bathrooms

Why you should book: The owners produce Brunello and can arrange a private tasting at their main cellar near Greve in Chianti. For wine lovers, this is the most immersive option on the list.

Villa with Hot Tub in the Centre of Montalcino

A beautiful villa in Tuscany with a private outdoor jacuzzi in the town of Montalcino, just opposite the famous fortress dating back to the year 1301. It’s a great choice if you’d rather stay in town, with restaurants and local life just steps away.

Carefully restored and elegantly furnished, the villa blends classic Tuscan features with modern touches—including a curated selection of contemporary art.

There is a large outdoor terrace that’s perfect for al fresco dining that offers panoramic views and there is also an outdoor jacuzzi that’s perfect for a dip in warmer months. The villa also supplied e-bikes for guests, making exploration of the surrounding area a cinch.

Wine enthusiasts will feel right at home as the owner of this chic Montalcino villa also runs a wine bar just around the corner. Tastings can be arranged with expert sommeliers at the nearby fortress, which holds the region’s largest selection of Brunello di Montalcino.

Sleeps: sleeps up to 6 people // 3 bedrooms // 3 bathrooms

Why you should book: If you’re after a luxury villa with easy access to wine tastings and restaurants within walking distance, this one is a fabulous choice. 

The Tuscan Coast

People are often surprised to hear that Tuscany has a coast, but it’s a key part of the region—stretching for 230km along its western border and dotted with beaches, ports, and laid-back seaside towns.

Beach lovers are spoilt for choice here from the glitzy town of Versilia in the north, the sandy beaches of the Etruscan coast, to the crystal-clear waters of the Maremma. 

There is even the island of Elba to consider. Elba is the largest Island of the National Park of the Tuscan Archipelago and is renowned for its mild climate, its beautiful beaches and crystal-clear sea, as well as being the place of Napoleon’s exile in 1814-15.

Tuscany villas by the sea with pools

Elba Island Holiday Home with Sea Views

Those searching for a coastal villa in Tuscany should consider Elba—a less obvious but wonderfully rewarding choice. This one sits near the Arcipelago Toscano National Park, where you can swim in clear waters, hike scenic trails, and even explore coastal caves.

It’s also close to Mineral Park, where you can visit the mineral museum and learn about the importance of mining to Elba.

This large, 4-bedroom villa is perfect for gatherings of family or friends and is within easy reach of the beach. It also offers a gorgeous outdoor pool with breathtaking views of the sea and a gorgeous garden with plenty of space for dining outdoors.

The interiors are finished in natural materials, giving at once both a contemporary yet cosy feeling. 

Sleeps: sleeps up to 9 people // 4 bedrooms // 4 bathrooms

Why you should book: The right choice if you want a coastal retreat rather than a countryside base – sea views, proximity to the Arcipelago Toscano National Park, and a genuine sense of escape from the mainland.

Bellissimo Blue: Luxury Coastal Villa with Private Beach Access

As beach villas in Tuscany go, this is the benchmark. This beautiful luxury villa is possible the best to be found on the region’s shoreline and offers direct access to the sea from its cliffside position.

The perfect setting for an uber-chic seaside holiday, the house is designed to frame perfectly the azure waters of the Tyrrhenian Sea from as many aspects as possible. 

The interiors of this airy villa are distinctly nautical, but in a chic and classy way. Perfect for a luxury family escape, there are several outdoor terraces (so everyone has enough space) as well as a tranquil garden.

The private beach access is the headline feature – direct access to the Tyrrhenian Sea from a cliffside position that most coastal villas in the region can’t match.

Sleeps: sleeps up to 12 people // 6 bedrooms // 3 bathrooms

Why you should book: If the budget allows, this is the strongest coastal option on the list. Suave, airy, and finished to a standard that justifies the price.

Finding Your Base in Tuscany

The right villa depends almost entirely on what you want from the trip. 

Chianti and central Tuscany give you the quintessential Tuscan experience – the rolling hills, the wine estates, the medieval towns – and the easiest access to Florence. 

The Val d’Orcia is slower, more dramatic, and better suited to a week based in one place rather than a lot of moving around. The coast is a different kind of trip altogether.

If you’re still deciding which part of Tuscany to anchor in, these posts cover the ground in more detail:

• For wine tours worth building into your stay: 15 Best Wine Tours in Tuscany

• For a self-drive route through Florence, Chianti, Val d’Orcia and Siena: Tuscany Road Trip: Florence, Chianti, Val d’Orcia & Siena by Car

• For the best towns to build your itinerary around: Best Towns in Tuscany, Italy: 11 Worth Adding to Your Itinerary