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Luxury rentals in Tuscany

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Top-rated luxury holiday rentals in Tuscany

Guests agree: these stays are highly rated for location, cleanliness, and more.

Entire villa · Cortona
Villa Laura
Renowned villa on the Cortona hills
$3,816 SGD per night
Entire villa · Tavarnelle Val di Pesa
Sole del Chianti
$1,909 SGD per night
Entire villa · Buonconvento
Villa Di Montesoli
$2,159 SGD per night

Luxury rentals for every style

The right home for your next dream getaway

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Popular amenities for Tuscany luxury holiday rentals

Other great luxury holiday rentals in Tuscany

Entire villa · Palaia
Villa Larino
$1,137 SGD per night
Entire villa · Umbertide
Casa Lazzari
$1,425 SGD per night
Entire villa · Palaia
$3,213 SGD per night
Entire villa · Siena
Il Fienile Di Montesoli
$1,024 SGD per night
Entire villa · Radicofani
Villa Poggio Fibbia
$1,526 SGD per night
Entire villa · Gaiole in Chiant
La Maccinaia
$1,307 SGD per night
Entire villa · Montespertoli
Villa Leonardo
$1,550 SGD per night
Entire villa · Allerona
Torre Bisenzio
$3,012 SGD per night
Entire villa · Tavarnelle Val di Pesa
Villa Chianti Fornace
$1,606 SGD per night
Entire villa · Lucca
Villa Clara
$2,019 SGD per night
Entire villa · Palaia
$2,840 SGD per night
Entire villa · Orvieto
Villa Barbi
$2,108 SGD per night

All about Tuscany

Luxury Retreats - the expert in Tuscany vacations

World-famous sights

With such a storied history, it’s no surprise that Tuscany is packed with must-visit wonders and Unesco heritage sites. Perhaps the most famous across the world is the leaning tower of Pisa. The bell tower with its wedding-cake tiers started to lean while it was being built during the 12th century, and rather than start over, construction simply continued, with one side built taller than the other in an effort to compensate. The lean was stabilized through restoration work in the late 20th century and has been featuring in amusing vacation photos ever since.

Down the road from Pisa, the city of Florence boasts multiple world-famous attractions - including Michelangelo’s David. This bigger-than-life-size statue (it’s an incredible 17ft tall) was completed in 1504 and has been considered one of the finest works of sculpture ever created, ever since. Located in Florence’s famed Uffizi gallery, crowds gather daily to marvel at the work. If you want to see it for yourself book tickets ahead of time - or if time is short, keep an eye out for the replica statue that stands outside the museum, in Piazza della Signoria.

Also in Florence, the green and white marble facade of the immense cathedral known as Il Duomo will take your breath away when you see it for the first time. Topped by an immense red-tiled dome, built by Brunelleschi, it is a staggering feat of Renaissance building expertise and is a must-visit for anyone interested in history or engineering. Our Florence vacation rentals made a great base for days spent exploring the rich history of these two cities.

A feast for foodies

Besides being the home of the Renaissance, Tuscany is famous the world over for another captivating export - red wine. For many years Italian wine was synonymous with Chianti served in straw-covered bottles on red-checkered tablecloths in Italian restaurants across the world. In reality, there’s a lot more to the wines of the region if you look below the surface.

One you really must try is Brunello di Montalcino, produced in the vineyards surrounding the town of Montalcino an hour’s drive south of Florence. Made from 100% Sangiovese grapes. The most famous are produced by the Biondi-Santi vineyard - and you can taste the magic for yourself with a winery tour. It’s one of the world’s most collectible wines, great for storing and enjoying in years to come, so try to bring back a bottle or two if you can. If you’re interested in learning more about Italian wine on vacation, your Luxury Retreats concierge can organize vineyard tours, private wine tastings and more.

Tuscany most famous dishes pair perfectly with the bold red wines of the region - perhaps none more so than bistecca Fiorentina -  a huge T-bone steak (most often the dish is served for two people) cooked over a charcoal fire and served rare with nothing more than a sprinkle of good quality salt. If a meat feast is not for you, Tuscany is also famous for hearty and delicious soups - such as Ribollita - a delicious reduction of tomatoes, cannellini beans and bread that will keep you going for hours.

Where to stay in Tuscany

From charming stone estates to city apartments in the heart of the action, whatever you’re looking for, we have a luxury home in Tuscany to fit the bill.

At home in the city

Exploring Florence is on many traveler’s bucket lists - and our centrally located apartments are just the ticket for an inspiring city break. If you’re planning a romantic escape, our charming one-bedroom apartments will be ideal. Alternatively, if you’re traveling with friends and family we have apartments sleeping up to 8 people that you’ll love. What they all have in common is their excellent locations - which will leave you walking distance from the Uffizi gallery, il Duomo and the many fabulous gelaterias and restaurants that surround them.

Country living

Have you been dreaming of really getting away from it all? Then nothing will suit you better than our gorgeous homes in the Tuscan countryside. Nestled in the heart of Chianti country with nothing but green hills covered with vines as far as the eye can see, if you’re looking for some serious R&R we have just the place. With homes sleeping as little as two people or as many as 44, you choose who to bring along with you and we will take care of the rest. Many homes have shaded courtyards, sun terraces or swimming pools that invite you to relax and leave your cares behind. Deep in the countryside you can snooze the day away, head out for a bike ride along the quiet lanes or set off for a tour of the local vineyard; the choice is yours.

The best of both worlds

If you enjoy mixing up city days or exploring with plenty of down time, our luxury rentals in Siena could be the perfect choice. Many of our homes in the region are just a short drive from the beautiful Medieval city but boast private swimming pools, landscaped grounds and plenty of room for your extended family or group of friends. With sweeping views of the countryside and plenty of peace and quiet, you can choose to spend your days relaxing by the pool, and then dip into city life when the mood strikes.

Similarly, our vacation rentals in Lucca offer the best of city and country living- plenty of space, swimming pools and well-equipped kitchens mean that children and adults alike will be entertained, playing in the pool, catching up on summer reading or cooking up a storm with a glass of Tuscan red in hand.

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