Artistic Retreat
8 guests
4 bedrooms
Castiglione d'Orcia, Siena
Old collides with new at this secluded villa in the middle of the south Tuscan hills. Days can be spent hopping between the vineyards of the Val d’Orcia or day-tipping to the UNESCO village of Castiglione d'Orcia, a short drive away.
Lighthouse Island
4 guests
2 bedrooms
Grosseto, Tuscany
This unique home offers an unparalleled escape to a private island in Tuscany, where the sea sparkles and time slows. Once a lighthouse, it's been beautifully restored, blending historic character with effortless luxury.
Architectural Narrative
4 guests
2 bedrooms
Montalcino, Siena
Bookended by the olive groves, cypress trees and rolling green hills of Southern Tuscany is this 1960s-style architectural feat designed and curated by a sculptor and architect duo. Perfect for two couples or a small group of friends looking to explore the region, this cleverly converted warehouse is airy and open-plan with large crittall-style windows looking out over the vineyard and rambling countryside beyond.
Honey & Fig
2 guests
1 bedrooms
Montalcino, Siena
Nestled in the heart of Montalcino, just steps from the main square and cathedral, this renovated townhouse offers an idyllic location with breathtaking views to boot. Inside, it delivers authentic charm and contemporary comforts – think high ceilings and striking timber beams alongside stylish artwork and state of the art amenities.
Explore the 2834 most perfect homes in our collection
Explore our selection of the finest luxury Holiday Rentals for your next getaway in Montalcino, Siena, Tuscany, Italy. The homes in Plum Guide's collection come fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Each home is professionally vetted and carefully handpicked, with both measurable and soft 'feel' elements thoroughly tested to ensure the highest quality. Book today and enjoy a short or extended stay in one of the best homes that Montalcino, Siena, Tuscany, Italy has to offer. Our friendly experts are also on hand 24/7, should you need any help finding the perfect Holiday Rentals for your trip.
