When you’re hunting for your dream Tuscany villa with a pool, it’s surprisingly easy to fall into one very sneaky trap that you only discover once you arrive. Booking sites are full of hundreds of gorgeous listings promising a refreshing dip, but in reality it’s very often a pool shared with several other apartments, where a handful of families crowd together all summer long. If you’re dreaming of total peace with a view of the cypress trees, you’ll need to choose much more carefully and read between the lines.
I went through the current listings for you and put together a detailed overview of the 20 most beautiful villas and houses with a pool, all with fantastic reviews from previous guests. I focused on different corners of this picturesque region so you can pick exactly what suits you — whether you’re after wine tastings or peace and quiet in the countryside. For each recommendation I also make it clear how the swimming situation really works, so you know exactly what you’re signing up for.
Everything you need — how to reliably spot a private pool, why fencing is crucial for families with small children, and which hidden fees to watch out for — is below. Renting a whole house works by slightly different rules than an ordinary hotel booking, so it pays to know the details before you type in your card number.
TL;DR
- Private vs. shared pool: Borgo-style complexes almost always have a pool shared by all guests.
- Fenced pool for kids: Look for the phrase “piscina recintata” in listings, which guarantees safety for the little ones.
- Swimming season: Outdoor pools are usually open only from June to September.
- Minimum stay: In high season, villas are often rented exclusively Saturday to Saturday.
- Deposit and cleaning: Budget for an extra final cleaning fee and a security deposit held on your card.
- No air conditioning: Traditional stone farmhouses often don’t have it at all, or only in some bedrooms.
- You’ll need a car: Most houses are reached via unpaved roads (strade bianche), so a car is essential.
- When to book: June and September offer the best value and weather, but sort out your stay up to six months ahead.
Private or shared pool? How to tell in advance
The biggest disappointment after arriving on holiday is realising you have to share the sun loungers with other people. If you absolutely insist on privacy, look for the phrase “private pool” or “exclusive pool” in the listing title, which is usually a reliable guarantee. Owners who offer the house to you alone are happy to show off this huge advantage right in the headline.
On the other hand, the description often includes the subtle phrase “shared pool”, which clearly signals sharing with other apartments. If you’re browsing complexes labelled borgo or case vacanza, you can be almost certain the pool is always communal for the whole property. These historic little villages converted into accommodation have wonderful atmosphere, but private swimming simply isn’t part of the deal.
If you’re not 100% sure from the photos and descriptions, don’t hesitate to message the owner directly through Booking.com. Italians usually reply very quickly and will happily confirm whether you’ll have the whole garden entirely to yourself. It’s a far better solution than spending your holiday disillusioned that your dream romance by the water looks more like a public swimming pool.
What renting a villa actually includes
Renting a whole private house works a little differently from booking a standard hotel room. A villa is always rented as a whole, with a minimum stay usually ranging from three to seven nights. In peak summer, owners often require both arrival and departure to fall on the weekend — most commonly you’ll come across a Saturday-to-Saturday rule, and a short mid-week stay is practically impossible.
Another specific feature is the security deposit, which is held on your payment card on arrival to cover any damage to the property. On top of that, there’s very often a one-off final cleaning fee that usually isn’t included in the base price shown in the search engine. So I recommend reading the booking terms carefully so you know exactly how much extra you’ll be paying.
It’s also important to remember that the pool is a seasonal thing and usually operates from May or June to September. Outside those months the water may be drained or covered with a tarp, even if the weather is gorgeous. Air conditioning is also far from standard in these old stone farmhouses — it’s often missing entirely, or only available in select bedrooms under the roof.
Absolutely essential is transport by your own or a rented car. Most of the loveliest secluded spots sit at the end of the so-called strade bianche — the typical unpaved white dusty roads that wind between the hills. Without a car you not only can’t get there, you also can’t nip out to buy fresh bread in the nearest village.
Where to stay: 20 of the most beautiful Tuscany villas with a pool
💡 Tip for accommodation and experiences: We prefer to look for accommodation on Booking.com, which usually has the best cancellation policies. For tickets, tours and activities, it’s worth comparing and booking through GetYourGuide.
Let’s take a look at the specific places to stay that earned the best ratings from previous guests. I’ve neatly divided all the tips into six popular areas, so you can choose the location that best fits your travel plans.
Villas in the Val d’Orcia and around Pienza
This area is exactly the landscape you know from postcards, calendars and films. Here you’ll find the most iconic rolling hills, solitary cypress avenues and historic little towns like Pienza and Montalcino. It’s an ideal spot for lovers of photography, sweeping views and the famous pecorino sheep’s cheese.
1. Poggio ai Gelsi
This beautiful house sits right beside picturesque Pienza and offers absolutely breathtaking views over the surrounding UNESCO-listed landscape. It boasts a rating of 9.1 Wonderful and a huge 439 reviews, making it one of the most tried-and-tested options in the whole area. Guests return again and again not just for the great location, but also for the incredible peace this place radiates.
You’ll have a gorgeous outdoor pool with a view over the valley, a spacious sun terrace for topping up your tan, and reliable air conditioning for hot summer days. Another plus is hassle-free free parking right on the property, which saves plenty of worry on day trips. The approximate starting price per night here is around €235, though it always depends on the specific dates and availability.
The place is absolutely ideal for couples and small groups of friends who want the best of the Italian countryside right at their fingertips. Mist in the valley in the morning, wine and sunset in the evening. At €235 per night you’d be hard pressed to find better value.
👉 Booking: Check availability and prices on Booking.com
2. Villa Fonte all’Oppio con area piscina recintata
If you’re heading off on holiday with little explorers, this house near Pienza should be top of your list. It has an excellent rating of 8.6 Excellent from 41 guests and offers something that’s surprisingly rare in Italy. The owners proudly announce right in the name that their property has a specially adapted pool area.
The biggest treasure for parents here is the properly fenced pool, which ensures your little ones can’t reach the water without your supervision. This safety feature is an absolutely crucial factor for families with small children — one that, sadly, hardly ever gets mentioned on blogs. So you can read a book on the terrace in peace while the kids run around the garden without you having to watch them every single second.
Beyond safety, the villa offers beautiful rustic interiors with exposed beams and a spacious kitchen where you can easily whip up dinner for the whole family. It sits on a gentle slope, so it offers lovely views of the surrounding rolling countryside that’s so typical of this part of the region.
👉 Booking: Check availability and prices on Booking.com
3. Casa Guaitoli
This charming property is located near the historic thermal baths of Terme di Petriolo and is a great choice for budget-conscious travellers. It boasts a fantastic rating of 9.3 Wonderful based on 174 reviews, proving that quality doesn’t always mean an empty wallet. Guests most love the amazing hospitality and the perfectly maintained outdoor spaces.
Waiting for you is a lovely outdoor pool with a view over the greenery, a well-kept sprawling garden full of shade, and a handy grill for evening gatherings. With an approximate starting price from around €90 per night, this is probably the best value for money in our whole roundup. Of course, in August you’ll pay more, but off-season it’s an absolute steal.
The location near the thermal springs also offers a great alternative for days when it might be a touch too chilly by the outdoor pool. You can head to the baths, warm up in the healing water, and return in the afternoon to your peaceful countryside retreat.
👉 Booking: Check availability and prices on Booking.com
4. Casa vacanze Raggio di Sole
This holiday home in the Grotte area is made for those who demand total privacy and don’t want to share their space with strangers. It’s earned a brilliant rating of 9.6 Exceptional from 111 happy guests, who in their reviews often highlight the spotless cleanliness and peaceful location. The owners look after the house with enormous care, and you can see it at every turn.
The biggest draw here is undoubtedly the genuinely private pool, reserved just for you and your family throughout your entire stay. For an approximate starting price from around €125 per night you also get free parking right by the house and every comfort imaginable. It’s a great opportunity to experience the luxury of your own swimming without paying astronomical sums.
The house is surrounded by greenery and offers a beautiful terrace where you can enjoy your morning espresso or an evening glass of wine. The garden provides plenty of shade and space to relax, so you may well find you don’t want to set foot off the property for the whole week.
Villas near Montepulciano and Vino Nobile
If your main goal is discovering great wine, the area around Montepulciano will absolutely delight you. This part of Italy is home to the famous Vino Nobile wine, and the surrounding hills are densely dotted with endless vineyards. The local historic towns also brim with excellent restaurants and cosy wine bars.
5. Borgo del Faggio – Case Vacanza
This sprawling complex near Montepulciano is one of the best-known and most sought-after places to stay in the whole area. It boasts a great rating of 8.9 Excellent and holds the largest number of reviews in our roundup — an impressive 475, which speaks to its enormous popularity. The estate resembles a little historic village, where the genuine countryside atmosphere of times past washes over you.
It’s very important, though, to point out one crucial thing so there’s no disappointment on arrival. Since this is a borgo-style complex, the pool here is shared with other guests staying in the other apartments. If you don’t mind a bit of company and enjoy chatting with fellow travellers by the water, this will be a perfect choice full of holiday cheer.
The property offers beautifully maintained gardens, typical stone and wood architecture, and a very strategic location for wine day trips. Each apartment has its own outdoor seating, so you’ll definitely have privacy for dinner or morning coffee. The atmosphere here just works. Stone walls, that proper Tuscan air, and yet you don’t have to worry about where the wifi is. Ideal for anyone who loves history without the hard work.
👉 Booking: Check availability and prices on Booking.com
6. Le Corolle
This charming house sits in a strategic spot near the renowned wine town of Montepulciano. It enjoys an excellent rating of 9.3 Wonderful from 132 guests, who can’t praise enough the warm welcome and carefully maintained grounds. It’s exactly the kind of place where you feel like you’re visiting good friends from the very first minute.
On warm summer days you’ll appreciate the beautiful outdoor pool with a breathtaking view over the surrounding countryside of vineyards and olive groves. The house also has a sprawling garden, a handy grill for al fresco dinners, fast wifi and free parking. Everything is set up so you can enjoy your holiday without any worries or compromises.
The surroundings invite endless walks among the vineyards and the discovery of small family wineries. In the evening you can drive into the centre of Montepulciano, pick up fresh ingredients at the market, and grill them back in the garden.
👉 Booking: Check availability and prices on Booking.com
7. Corolle2
Right next door to the previous property you’ll find this smaller but all the more cosy sister listing. So far it has a superb rating of 9.6 Exceptional from just 7 guests, but the quality of service and attention to detail is at exactly the same level. It’s an ideal retreat for couples or small families looking for a more intimate atmosphere.
Guests have every comfort at their disposal, including access to refreshing water, all at a very appealing approximate starting price from around €135 per night. The interiors are furnished with incredible feeling for tradition, so there’s no shortage of terracotta floors, solid wooden furniture and cosy textiles. You’ll feel like you’re in a romantic Italian film from the 1980s.
The location is absolutely ideal for day trips all across the southern tip of the region. You can easily set off for a tasting of the famous Vino Nobile, cycle a rented bike through the surrounding hills, or just laze about with a book in the shade of the old trees.
👉 Booking: Check availability and prices on Booking.com
8. Podere Pisinano – Tuscan villa with swimming pool
This gorgeous countryside villa has its greatest asset spelled out clearly right in its name, so you know exactly what to look forward to. It boasts an absolutely excellent rating of 9.6 Exceptional from 5 guests, and even though there aren’t many reviews yet, every single one heaps incredible praise on this place. The owners take care over every detail to make your stay utterly flawless.
Swimming takes centre stage here, and the wonderful pool is set right into the greenery with views over the endless vineyards around Montepulciano. The villa has undergone a very sensitive renovation, so from the outside it looks like a historic farmhouse, but inside it offers every modern comfort imaginable. It’s a great choice for a group of friends who want to spend evenings together around a big table on the terrace.
The proximity to Montepulciano means you’re just a few minutes’ drive from the best restaurants and historic sights. And yet you sleep in total silence surrounded by nature, far from the noise of tour buses. Evenings around the big table on the terrace, vineyards outside the window in the morning. For a group of friends, you’ll struggle to find a better backdrop.
👉 Booking: Check availability and prices on Booking.com
9. Villetta Toscana – Montepulciano
If you’re travelling just as a couple or with a small child, this delightful little villa near the vineyards definitely shouldn’t slip past you. It’s earned a beautiful rating of 9.6 Exceptional based on 11 reviews from previous visitors, who most often praise the perfect cleanliness and very warm welcome. It’s a compact but incredibly cosy spot for a peaceful holiday.
This smaller villa for a couple or a small family offers complete privacy and a beautifully landscaped outdoor space for summer days. The house is surrounded by a carefully maintained garden, where you’ll find plenty of shady nooks for reading or an afternoon siesta. The kitchen is very well equipped, so you can easily cook up anything you bring back from the local market.
Thanks to its strategic location, you’ll be a short drive from both shopping and culture in town and long walks in nature. The owners will also happily advise you on choosing the best wineries in the area — the kind ordinary tourists usually never reach.
Villas near San Gimignano
The town of San Gimignano — often nicknamed the medieval Manhattan thanks to its tall stone towers — is one of the most famous symbols of the whole of Italy. Staying in this area lets you admire the town’s unmistakable skyline right from the water, and you’ll also be very close to other gems like Siena and Florence.
👉 Booking: Check availability and prices on Booking.com
10. Villa Remignoli
This gorgeous property lies right beside the famous medieval towers and offers an incredibly romantic setting for your holiday. Guests rated it 9.6 Exceptional based on 19 reviews, in which they often mention the fantastic location and very spacious rooms. It’s a classic example of robust Tuscan architecture that will charm you at first sight.
The garden with its spacious seating is made for long summer evenings with a glass of white Vernaccia, grown right on the surrounding slopes. The views over the countryside are breathtaking and the peace around you is a real balm for the soul after a day in the bustling town centre. The house is ideal for a larger family looking for plenty of space and privacy.
Thanks to the great accessibility, you can set off into San Gimignano early in the morning, before the day-trip crowds arrive. Wander the empty streets, stop for the famous gelato on the square, and retreat safely back into the shade of your villa before the midday heat. It’s the best way to truly enjoy this famous town to the full.
👉 Booking: Check availability and prices on Booking.com
11. PAPAVERO ROSSO
This accommodation gem near San Gimignano boasts a truly exceptional status that’s sure to catch your eye. It’s earned an absolutely incredible rating of 9.8 Exceptional from 15 guests, making it the highest-rated place to stay in our whole roundup today. Such a high score guarantees that a truly extraordinary experience awaits you, without a single hitch.
Guests agree that here you don’t have to worry about a thing and everything works as it should. The outdoor spaces are an absolute oasis of calm, where you can relax after a day of exploring and gather strength for the next. The owners look after their guests with such care that nobody wants to leave for home.
The location is absolutely strategic for discovering the biggest hits of central Tuscany. Within less than an hour’s drive you can reach Volterra, Siena and Florence. And yet in the evening you return to a place where you hear only crickets and the wind in the olive tree crowns. If you’re after flawless quality, you definitely won’t go wrong here.
👉 Booking: Check availability and prices on Booking.com
12. Dolce Villa Toscana – private pool, air conditioning
If for you a holiday is a synonym for absolute luxury and you refuse to make any compromises, this stunning villa will instantly win you over. It boasts a fantastic rating of 9.7 Exceptional from 11 guests, who spare no superlatives in their reviews and highlight the utterly professional approach. It’s a place that fulfils even the most demanding ideas of perfect accommodation.
As the name suggests, waiting for you is a genuine private pool plus air conditioning, which in these historic houses is a huge and very rare advantage. I must warn you, though, that we’re in the highest luxury segment here, so the approximate starting price begins at around €990 per night. For that sum, however, you get service, facilities and privacy that are hard to match.
The villa is fitted with the latest technology while still keeping its historic charm and authenticity. You can hire a private chef to prepare dinner, or simply laze on designer loungers and enjoy views reminiscent of Renaissance paintings. You’ll pay extra for this, but when you’re celebrating an anniversary or on your honeymoon, €990 per night suddenly becomes a very understandable amount. 😉
Villas near Cortona and in the Val di Chiana
The town of Cortona, made famous by the celebrated book and film Under the Tuscan Sun, sits high on a hilltop and looks down over the fertile Val di Chiana. This area offers a calmer, more authentic atmosphere than the overcrowded north, great restaurants in the winding streets, and beautiful views all the way to Lake Trasimeno.
👉 Booking: Check availability and prices on Booking.com
13. Villa Augusto
This impressive villa near Cortona looks like it’s been cut straight out of an interiors magazine and is guaranteed to charm you with its atmosphere. It achieved an excellent rating of 9.4 Wonderful based on 109 reviews, which is very strong proof of its long-term quality and reliability. Guests especially love the generous space and the amazing terrace that practically invites evening lounging.
You’ll have a lovely shady terrace and, of course, a refreshing pool where you can spend hot summer afternoons. The approximate starting price is from around €190 per night, which for such a large and beautiful property in this location is a very fair deal. The rooms are bright, airy and furnished with respect for local traditions.
The location below Cortona is absolutely ideal for day trips to nearby Umbria or to the huge Lake Trasimeno, where you can rent a boat. In the morning you can run up the hill into the historic centre for fresh bread, and in the afternoon just laze by the water with a view over the valley.
👉 Booking: Check availability and prices on Booking.com
14. Il Pozzo degli Angeli
This beautiful holiday home is a great choice for those seeking modern comforts in a historic wrapping. It’s earned an absolutely brilliant rating of 9.7 Exceptional, though so far only from 6 guests, but the photos and reviews speak for themselves. The whole property recently underwent a complete and very sensitive renovation.
Thanks to this recent refresh you’ll find modern bathrooms and a new kitchen, as well as a wonderful pool with a view over the countryside, a blooming garden and a handy grill. With an approximate starting price from around €140 per night, it’s a very tempting offer for couples and small families looking for quality at a reasonable price. Everything here smells of newness and cleanliness.
The area around Cortona is criss-crossed with plenty of hiking and cycling trails, so if you like an active holiday you won’t be bored for a minute. In the evening you can relax your tired muscles in the water and prepare a great dinner from local ingredients under the starry sky.
👉 Booking: Check availability and prices on Booking.com
15. Villa Serena & Dépendances
This charming property offers very pleasant facilities for a family holiday within reach of famous Cortona. It holds a solid rating of 8.8 Excellent based on 29 reviews, with guests often enthusiastically praising the outdoor spaces and writing that “the pool is very nice” and perfectly maintained. It’s a house that relies on traditional atmosphere and comfort.
The grounds offer plenty of space for lazing and active relaxation, with an approximate starting price from around €205 per night. The garden is full of mature trees that provide merciful shade during the summer heat, and the outdoor seating is ideal for long shared breakfasts. The interiors are classic, with dark wood and typical tiling.
Since the main villa also comes with a smaller annexe, this accommodation is absolutely ideal for multi-generational families who want to spend time together while still having their own privacy. You can head off together to the markets in nearby Arezzo or simply explore Cortona’s winding streets. It offers enormous flexibility for larger groups.
👉 Booking: Check availability and prices on Booking.com
16. Borgo Syrah
This very elegant apartment complex near Cortona blends history with modern Italian design. It enjoys a very good rating of 8.7 Excellent from 29 happy guests, who especially admire the architecture and tasteful interiors. The accommodation is set right in the heart of a renowned winery, which gives it an unmistakable atmosphere.
Each apartment has its own entrance and offers a lovely view over the carefully maintained garden full of herbs and flowers. The approximate starting price here is from around €245 per night, and you should be aware that the pool and wellness zone are shared with other guests. So it’s not absolute privacy, but on the other hand you gain access to great facilities on the level of a boutique hotel.
During your stay, definitely don’t miss the local wine tasting, as the borgo is one of the renowned producers in the area. You can walk through the vineyards, visit the old cellars and learn plenty of fascinating facts about winemaking. If you like to know more about wine than just “it’s good” and also enjoy a nicely furnished room, this is the place for you.
Villas near Lucca and in the north
The northern part of the region around the beautiful city of Lucca offers a slightly different landscape, where gentle hills slowly give way to dramatic mountains. It’s an ideal base for those who want to combine a countryside stay with trips to the sea on the nearby Versilia coast or to the wild marble quarries of Carrara.
👉 Booking: Check availability and prices on Booking.com
17. Villa Camilla – WIDE – EXCLUSIVE POOL
This impressive historic villa lies right beside the centre of Lucca and is a genuine one-off. It boasts a great rating of 8.8 Excellent from 46 guests, who especially value the incredible accessibility of the sights combined with countryside calm. It’s a huge house that easily fits even a truly large family or group of friends.
The absolute biggest draw here is the enormous ⭐ exclusive (non-shared) pool, which is yours alone throughout your entire stay. The villa also has a large outdoor grill and a lovely garden, all just an amazing 1.2 kilometres from the famous church of San Michele in Foro. Such an enormous private space within walking distance of the historic city centre is something truly unheard of.
So you can have a leisurely morning swim, breakfast in the garden, and then walk to explore Lucca’s famous walls, which you can cycle around in full on a rented bike. In the afternoon you can relax undisturbed on a lounger with a book in hand.
👉 Booking: Check availability and prices on Booking.com
18. Il Nido
This immensely cosy stone house hides in the green hills north of Lucca and guarantees a perfect escape from civilisation. It’s earned a fantastic rating of 9.6 Exceptional based on 19 reviews, in which guests keep repeating how magical and peaceful this place is. The owners renovated the house with enormous respect for the original architecture.
Instead of a classic pool, waiting for you here is an outdoor plunge pool and spacious seating in the garden, from where you have the whole valley spread out before you. The house is about 22 kilometres from the Leaning Tower of Pisa, so the famous sights are within reach, yet you sleep in the total silence of the mountain wilderness. It’s an incredibly romantic retreat for couples.
The surrounding forests and hills are laced with plenty of trails that practically beg for hikes or mountain biking. In the evening you can head to the nearby village for a simple but hearty country dinner, where you won’t run into a single tourist.
👉 Booking: Check availability and prices on Booking.com
19. Tenuta Fagnani
This sprawling estate offers a great chance to spend your holiday in the hills near Lucca at a very affordable price. It holds a solid rating of 8.0 Very Good from 34 guests and represents the cheapest segment in this northern location. Despite the lower price, you’ll find everything essential here for a relaxed summer holiday full of sunshine.
The estate’s greatest pride is the beautiful outdoor pool and the amazing view straight to the mountains, which will charge you with energy every morning. The rooms are furnished rather simply and traditionally, but the outdoor spaces are very generous and perfectly maintained. It’s a great choice for families who aren’t after luxury but want to enjoy beautiful nature and water.
From the estate you can easily set off on trips into the nearby Garfagnana mountains, which offer stunning scenery, deep gorges and old stone bridges. After a demanding hike, there’s nothing better than jumping into refreshing water and grilling something delicious in the evening.
Villas in the Maremma and the south
The southern part of the region known as the Maremma is noticeably wilder, sunnier and also more affordable than the famous north. It’s a land of pastures, deep forests and hot thermal springs that has kept its rugged and very authentic face, luring you to explore off the main tourist routes.
👉 Booking: Check availability and prices on Booking.com
20. Villa Il Turchetto
This gorgeous stone house near the little town of Manciano represents the best of the southern countryside. It’s earned a great rating of 9.4 Wonderful based on 23 reviews, with enthusiastic guests often mentioning that here you’ll find an “amazing pool, incredibly clean” and superbly maintained. It’s a place that instantly grabs you by the heart with its genuine atmosphere.
The villa offers total peace, beautiful views over the wild landscape and plenty of outdoor space for evening dining. A huge advantage is the proximity to the famous thermal springs of Saturnia, where you can head for an evening dip once the temperatures drop a little. The house is very spacious and ideal for a larger family or group of friends who want to spend time together.
The Maremma also offers great access to the sea, so you can take a day trip to the beautiful beaches of the Argentario peninsula and return to your peaceful retreat in the evening. Don’t forget to also explore the ancient little towns carved into the tufa rock, like Pitigliano or Sorano, which are very close by.
And if twenty houses aren’t enough for you, I recommend also checking out Agriturismo Capricorni near Massa Marittima. It has a rating of 9.3 from 150 guests and works as a cheaper alternative — just note that the villas here share a separate pool with other guests.
How to choose based on your type of holiday
| I want… | where | why |
|---|---|---|
| classic Tuscan hills and photos | Val d’Orcia, Pienza | iconic landscape, close to Montalcino and Montepulciano |
| wine and tastings | Montepulciano, Chianti | Vino Nobile and Chianti Classico on the doorstep |
| a family with small children | Pienza (fenced pool), Cortona | shallower and safer facilities |
| peace and lower prices | Maremma, around Grosseto | cheaper than the north, close to sea and thermal baths |
| a mix of town and countryside | Lucca, Cortona | a short hop to the centre, but you sleep in the greenery |
| luxury without compromise | San Gimignano | Papavero Rosso and the like |
When to go and when to book
If swimming is your number one priority, you’ll need to plan very carefully. The local pool season runs roughly from June to September, and in May and October the water tends to be very cold and owners often don’t even open the pool. So always check in advance whether it will actually be filled during your stay.
With your budget in mind, definitely be prepared that the highest prices reign in July, August and especially around the Ferragosto holiday (15 August), when even Italians themselves flock to the region. During this period you’ll not only pay the most, but you’ll also have to reckon with enormous heat and ever-present crowds on the roads and in restaurants.
The best value for money, on the other hand, comes in June and September, when the pools work reliably, prices are noticeably lower, and the weather is pleasantly summery without the exhausting extremes. Whichever month you choose, the loveliest villas vanish incredibly fast, so I recommend booking at least six months ahead so you have plenty to choose from and can keep an eye on the stricter cancellation terms too.
What to ask before booking
Before you finally enter your payment card details, I recommend sending the owner a short message. This little numbered checklist of 8 questions could save you from a very unpleasant surprise on arrival.
1. Is the pool really private just for us, or is it shared with other apartments? 2. From which date to which date is the pool filled and fully operational? 3. Is working air conditioning available in all bedrooms, or only in some parts of the house? 4. Exactly how much is the final cleaning fee and how large a security deposit is held on site? 5. How long is the stretch of unpaved road (strade bianche) to the villa, and can an ordinary car handle it without trouble? 6. Are all bed linens, bath towels and special pool towels included in the base price? 7. Is the pool fully fenced with a gate (if you’re travelling with very small children)? 8. What is the set minimum stay, and does the rule apply that you arrive exclusively on Saturday?
What you’ll cook in the villa
Renting a house with a fully equipped kitchen practically invites you to cook for yourself on at least some days. Stop by the local market. Pecorino from Pienza, olive oil pressed a few kilometres away, and tomatoes still warm in your hands from the evening sun. You don’t need more than that. You’ll see that cooking with great ingredients is incredibly easy and fun.
Among the simplest meat-free dishes, I definitely recommend trying the traditional pappa al pomodoro or the refreshing bread salad panzanella, which really anyone can put together. Also great are the typical thick pici pasta with a simple sauce of garlic and tomatoes — and don’t forget to open a bottle of local wine alongside, and end the evening with hard almond biscuits cantucci dipped in sweet Vin Santo.
If you come across the huge bistecca alla fiorentina, wild boar (cinghiale) or the ever-present cured meats and salumi in restaurants or on the butcher’s board, know that these are the famous local meat specialities. This region is very renowned for them, but genuine rural home cooking always relied more on vegetables, bread and pulses, with which you can work wonders in the kitchen.
Where to go next
- Tuscany: 30 most beautiful places and a 7-day itinerary
- Agriturismo in Tuscany: 20 tips, prices and how to choose
- Weather in Tuscany: temperatures month by month and when to go
- Tuscany by car: a 7-day itinerary
- Siena and San Gimignano: 8 tips on what to see
- Lucca: 22 tips on what to see and why to cycle the walls
- Wellness hotels in Tuscany: 12 thermal baths
- Where to go on holiday in Italy: 20 best places
Frequently asked questions
Before you make your final decision and confirm your booking, you might still have a few practical things on your mind. Here are the answers to the most common questions I get about accommodation in Italy.
How much does a villa with a pool cost?
Indicative starting prices per night range from around €90 for the cheaper and smaller houses. You can usually get a standard property for €150 to €250 per night, while luxury and historic estates are priced significantly higher, easily reaching around €1,000.
Is the pool private?
Unfortunately, this is not always the case, so you need to read the descriptions carefully. With accommodations like borgo and case vacanza, the pool is usually shared with other apartments. Look for a private pool under the keywords “private pool” or “exclusive pool”.
When is the pool open?
Outdoor pools are usually filled and fully operational from around June until the end of September. However, always check with the owner in advance, as in May or October the water may already be drained or covered.
What is the minimum rental period?
You usually need to count on a minimum stay of 3 to 7 nights. In high summer season (July and August), owners often require arrivals and departures exclusively on weekends, so a strict Saturday-to-Saturday rule applies.
Do I need a car?
Yes, you will need a car practically always and everywhere. Most of the most beautiful farmhouses are not located on the main road, but you have to reach them via the so-called strade bianche, dusty unpaved roads.
When should I book?
If you’re planning to go during the holidays (July and August), you should sort out your booking as much as six months in advance. The best offers disappear incredibly quickly, and at the last minute only the most expensive or the least desirable ones remain.
Is it suitable for small children?
Absolutely, but always ask specifically whether the house has a fenced pool (piscina recintata). It’s a crucial safety feature that will save you as parents a lot of nerves and ensure a much more relaxed holiday.
Are there any extra charges?
When renting an entire house, you will almost always pay a one-time final cleaning fee, which is not included in the accommodation price. Additionally, a security deposit is typically blocked on your card upon arrival in case you damage anything in the house.
👉 Booking: Check availability and prices on Booking.com
Tips and Tricks for Your Vacation
Don’t Overpay for Flights
Search for flights on Kayak. It’s our favorite search engine because it scans the websites of all airlines and always finds the cheapest connection.
Book Your Accommodation Smartly
The best experiences we’ve had when looking for accommodation (from Alaska to Morocco) are with Booking.com, where hotels, apartments, and entire houses are usually the cheapest and most widely available.
🚗 Car rental on the roadVerified rental cars in ItalySearch with the DiscoverCars comparison engine — it compares prices from dozens of local and international rental companies, and most bookings come with free cancellation.
Compare car prices in Italy →Don’t Forget Travel Insurance
Good travel insurance will protect you against illness, accidents, theft, or flight cancellations. We’ve had a few hospital visits abroad, so we know how important it is to have proper insurance arranged.
Where we insure ourselves: SafetyWing (best for everyone) and TrueTraveller (for extra-long trips).
Why don’t we recommend any Czech insurance company? Because they have too many restrictions. They set limits on the number of days abroad, travel insurance via a credit card often requires you to pay medical expenses only with that card, and they frequently limit the number of returns to the Czech Republic.
Find the Best Experiences
Get Your Guide is a huge online marketplace where you can book guided walks, trips, skip-the-line tickets, tours, and much more. We always find some extra fun there!
