Don't have dates? Click here | Looking for a shorter stay? Inquire here
Experience the charm of Tuscany with our vacation rentals near the medieval city of Arezzo, set among rolling hills dotted with vineyards and charming hilltop villages. From cozy cottages nestled in a vineyard to spacious villas, each property offers a unique blend of history, relaxation and stunning views of the Chianti hills. Enjoy the serene beauty of medieval castles, lush gardens and private pools that are perfect for soaking up the Tuscan sun. Whether you’re exploring nearby towns or savoring local wines, our villa rentals near Arezzo provide the perfect backdrop for a memorable vacation in Tuscany.
Enjoy Chianti hill views while lounging on the large terrace of Belvedere on the Bucine vineyard estate. A perfect medieval castle overlooks the hamlet "borgo" that is now a vacation village of a cottages and apartments.
Enjoy the terrace at roomy Poggio. Located on the Bucine vineyard where you can enjoy a "borgo" feel in the private cottages and apartments along with Chianti hill views and a private restaurant.
The romantic Loggetta has a cute terrace and lovely setting on the Bucine vineyard estate complete with a medieval castle and charming hamlet with private restaurant and views of the Chianti hills.
Limonaia's lush garden patio beckons for a sweet Tuscan holiday. Tucked away on the Bucine vineyard with its lovely collection of vacation cottages. Take in views of the Chianti hills that you'll dream about.
Cotogno has two terraces and a garden and is set on the pretty Bucine vineyard estate. A medieval castle and Chianti hill views make this the perfect setting for your next Tuscany getaway.
Breathe in the fresh air as you pull into the ample driveway of this most traditional Tuscan villa. A classic, handsome villa awaits with massive vistas of the lush valley and far beyond.
This beautiful holiday villa near the medieval town Monterchi has a wonderful character that embraces the vistas and beauty of Tuscany while offering a setting of pure relaxation for your Italian getaway.
Enjoy a sweeping views of gently rolling hills dotted with olive orchards in the Valdambra area between Siena and Arezzo. Find unspoiled beauty at this peaceful and secluded Tuscan villa.
Enjoy beautiful the views of Tuscany hills while relaxing at the La Collina villa. Ideal location for venturing out for sightseeing, wine tasting, dining on Tuscan regional foods or a spa visit.
Discover the tranquil beauty of Tuscany with a convenient location near Florence at our exquisite vacation rentals on the Vecchietto Estate near Reggello. Surrounded by lush gardens and scenic views, each villa offers a private retreat with access to luxurious amenities, including private pools, on-site dining and the charm of Tuscany’s rustic elegance. Enjoy the perfect blend of relaxation and exploration, with nearby towns like charming Arezzo and wine tasting in Chianti just moments away.
The dreamy Aquila Villa is surrounded by trees and a beautiful garden. Enjoy a private tranquil retreat in the heart of Tuscany with the perk of access to the all of the Vecchietto Estate amenities.
A meticulously restored villa that marries old world charm with modern amenities located in an easily accessible location, near several scenic Tuscan towns, sightseeing, wine tasting, outlet shopping.
Villa Passera is a comfy home with a private pool, beautiful gardens and rustic fireplace. A private pool, garden area and the amenities available to all properties on the Vecchietto Estate.
The Tucano Villa enchants with its beautiful garden and private infinity swimming pool. Plus enjoy the on-site restaurant and the amenities available to all properties on the Vecchietto Estate.
The Maragone villa is an elegant take on the classic rustic Italian villa with a private pool plus on-site restaurant and all the amenities available to all properties on the Vecchietto Estate.
The beautiful, spacious Gabbiano Villa and adjacent cottage is grande and yet still manages to feel intimate. A private pool, garden area, and the amenities available to all properties on the Vecchietto Estate.
Book the Aquila Villa along with an adjacent cottage for even more space. Enjoy a private tranquil retreat in the heart of Tuscany with access to the all of the Vecchietto Estate amenities.
Perfect for larger groups, plan a stay at the Tucano Villa along with a nearby cottage for even more space. Includes on-site restaurant and all the amenities available on the Vecchietto Estate.
The beautiful, spacious Gabbiano Villa and adjacent cottage that still manages to feel intimate. A private pool, garden area, and the amenities available to all properties on the Vecchietto Estate.
Enjoy the splendid natural beauty of Tuscany with our beautiful vacation rentals near Montecatini Terme. Conveniently located between Florence and Pisa, these secluded villas offer panoramic views of olive orchards, rolling hills and the picturesque Val di Nievole. Here you’ll find the perfect blend of relaxation and adventure with private pools, comfortable amenities and easy access to Tuscany’s top sights as well as off-the-beaten-path villages and stunningly beautiful scenic drives.
On a hill overlooking Tuscan olive orchards and the valley below, this roomy and comfortable villa is located in a scenic region of Tuscany with many activities to see and do in the vicinity.
A comfortable villa above the Val di Nievole, the Valley of the Mists. Relax around the large swimming pool or sightsee galore. Spacious and bright, every room has a view and air conditioning.
This large and gracious Tuscan villa has all the amenities needed and is close to the charming town of Montecatini Terme. It overlooks rolling hills of olive groves and woods of chestnuts and oaks.
Spend an unforgettable holiday discovering the beauty of Tuscany’s Val d’Orcia with our luxury vacation rentals set amidst tranquil vineyards and rolling hills. Located in a UNESCO World Heritage site, these charming villas offer gorgeous countryside views and easy access to historic villages, renowned vineyards and thermal baths. Enjoy the perfect blend of rustic charm and modern comfort in one of Italy’s most picturesque regions!
Fine restored farmhouse with tranquil views set among 5 acres of beautiful orchards. Just minutes driving to scenic San Casciano dei Bagni, Villa Riposo Verde is a wonderful holiday retreat.
Enjoy Tuscan charm with luxury amenities at Borgo Vespa. Located on a stunning, vast estate in the unspoiled southeastern Tuscan countryside with unparalleled views and tranquil olive orchards.
Borgo Beco has spacious luxury and a working fireplace. Located on a stunning, vast estate in the unspoiled southeastern Tuscan countryside with unparalleled views and tranquil olive orchards.
Relax by the Borgo Bersagliere fireplace on crisp fall days. Located on a stunning, vast estate in the unspoiled southeastern Tuscan countryside with unparalleled views and tranquil olive orchards.
High beamed ceilings, comfort and luxury at Borgo Ronda. Located on a stunning, vast estate in the unspoiled southeastern Tuscan countryside with unparalleled views and tranquil olive orchards.
Borgo Tiglio delights with typical Tuscany decor and comfort. Located on a stunning, vast estate in the unspoiled southeastern Tuscan countryside with unparalleled views and tranquil olive orchards.
Handsome Borgo Fonte fulfills your Tuscany dreams for two. Located on a stunning, vast estate in the unspoiled southeastern Tuscan countryside with unparalleled views and tranquil olive orchards.
You'll be warmly welcomed at the Graziosa Villa located within walking distance of the scenic Tuscany village of San Casciano dei Bagni, famous for its thermal baths, upscale charm, restaurants and beautiful views.
Located in Tuscany’s scenic Val d’Orcia, this villa has stunning views of the incredible countryside. Near the picturesque town of Montechiello and the beautiful small city of Pienza.
Discover a tranquil side of Tuscany with our luxury vacation rentals near Lucca, set on the expansive and beautifully restored Perla estate. Just a 15-minute drive from the charming city of Lucca, these fully serviced villas combine old-world charm with modern elegance, offering an unparalleled level of service and comfort for a relaxed stay.
Fulfill your Tuscany vacation dreams at the regal Calla Villa. Located on the Perla estate, an impressive collection of luxury villas just a 15-minute drive from the beautiful city of Lucca.
The Fiore Villa boasts gorgeous views, old-world charm and traditional elegance. This luxury villa is part of the Perla estate of fully serviced villas located just a 15-minute drive away from lovely Lucca.
Rustic elegance meets Tuscan refinement at the Fresia Villa. The Perla estate is an impressive collection of fully serviced luxury villas located on an expansive estate just a 15-minute drive to nearby Lucca.
Savor the sweet life at the Villa Magnolia. The Perla estate is an impressive collection of fully serviced luxury villas located on an expansive estate just a 15 minute drive to the beautiful city of Lucca.
Explore the heart of Tuscany with a stay at one of our vacation rentals in the renowned Chianti wine region. Surrounded by rolling hills, vineyards and olive groves, these stunning villas offer a quintessential Tuscan stay. Enjoy breathtaking views, luxurious interiors and a serene atmosphere all with easy access to the charming villages of Chianti like Greve, Panzano and Gaiole. Ideal for wine enthusiasts looking to experience the ultimate Tuscan wine destination!
The ultimate Tuscany experience awaits you at La Rosetta Villa Grande. You'll be enchanted by the scenic views of vineyards and the gently rolling Chianti hills that stretch out into the distance.
Savor the best of Tuscan life in a beautifully restored villa in Italy’s coveted Chianti region. Enjoy views overlooking verdant vineyards and olive trees. Perfect for a truly restful vacation!
Escape to the hillsides just outside of Florence with a stay at a very special villa rental in Fiesole. Gorgeous views of Florence, a private swimming pool and lush gardens offer everything you’re looking for in a Tuscan retreat all with easy access to Florence - the very birthplace of the Renaissance!
Breathtaking views of Florence on the road to Fiesole as you approach the villa. The wonderful swimming pool and beautiful gardens of exquisite Divine Dante villa will make your villa dreams come true.
Experience the charm of Tuscany with our vacation rental in Lucignano, tucked away in a beautiful spot between Siena and Arezzo. Enjoy a stay surrounded by expansive grounds, spacious interiors and a sparkling pool along with easy access to the medieval hilltop town of Lucignano, renowned vineyards and untouched countryside.
Beautiful grounds, spacious inviting interiors, a sparkling blue pool surrounded by greenery and vistas, all well placed within easy reach of major vineyards & medieval towns. Savor the Tuscan life!
Discover the allure of Tuscany’s quietly beautiful coastline with our luxurious villa rentals in the Maremma, renowned for its stunning coast along the Tyrrhenian Sea and world-famous Super Tuscan wines. These villas offer the perfect blend of relaxation and indulgence, where you can lounge by the pool, enjoy ocean breezes and immerse yourself in the rich history and beauty of coastal Tuscany.
Idyllic oceanfront luxury villa with all amenities in Tuscany's Maremma territory famous for super-Tuscan wines. Picnic at the beach, lounge by the pool and immerse yourself in prime coastal Tuscany.
Soak up Tuscany's rich history, world-famous wines and heady coastal views in the Maremma. The Columbe Villa enjoys ocean breezes, a fantastic location plus an on-site staff for a most memorable stay.
Just southwest of Siena, discover a charming side of Tuscany with a stay at a vacation rental surrounded by picturesque vineyards and rolling hills. An easy drive to the historic city, this villa offers the perfect base to explore Siena’s rich culture as well as the region’s ancient towns and world-class wine country. Enjoy the tranquility of the countryside, relax by the pool and savor the best of Tuscan food and wine in this enchanting spot.
In a picture-perfect location surrounded by vineyards, this enchanting villa is just outside Siena in an area that abounds with history, culture and, of course, fabulous food and wine!