Trulo Aromatic Green in Ostuni

How does crashing in a domed castle with jaw-dropping views of Ostuni’s surrounding countryside sound?

The entire place costs only $109 per night, a far better deal than you’ll find at the nice hotels in town — especially when split among friends.

La Salentina on the Salento Peninsula

La Salentina sits just outside of the city of Tricase within the natural beauty of the Salento Peninsula — the heel of the boot.

It has views of the nearby Adriatic Sea and a patio rivaling that of an upscale beach resort.

Historic Villa with Island Views of Lago Maggiore

Sleeping four at just $191 per night, your crew can even splurge on a nice bottle of wine to enhance the experience. Lago Maggiore is home to a series of rolling hills and small islands jutting out from the water, and you’ll sit right above the water in this villa, which retains old charm while certainly not shorting on modern comforts.

La Maison Bellevue in Rome

This flat is like that Neil Diamond song, “Up on the Roof,” only better because you’re in Rome.

From your rooftop perch, you’ll overlook the dramatic landscape of the city. It’s right in the heart of Rome and near the Spanish Steps.

La Casetta Di Nana in San Mantano, Naples

A cottage overlooking the water on the Amalfi Coast is about as dreamy as it gets. The view from the living room couch will nearly have you convinced that you’re on a boat crossing the adjacent Tyrrhenian Sea.

Terraced apartment in Naples

This loft, and its accompanying view of Naples, are worth a trip to Italy in and of themselves. It’s big enough that the cool breeze of the coast whistles through the apartment while offering the seclusion of a walled-off terrace.

Casa do Saraceno Siracusa in Catania

This place is basically a mansion right on the waterfront. It looks like something you’d see used for a swanky aperitivo party scene on a movie set, with characters dressed to the nines sipping fine wines from crystal glasses.

AltanaAlbaChiara in Venice

This snug two-bedroom flat is within walking distance of the heart of Venice, not far from the Grand Canal. Sip wine by moonlight as you look out over the city, taking in the canals and rooftops, the city’s energy buzzing below you.

Domus Claudia on the Amalfi Coast

You’re coming to the Amalfi Coast to stare in awe at the classic cliff-lined architecture as much as the coast itself, and there’s nary a better place to do it than on the balcony of this two-bed, four-person villa.

You’ll be within walking distance of the town center and the cathedral of Amalfi, but good luck pulling yourself away from the views.

Chiara’s House on the Amalfi Coast

You’ll have to walk 100 steps to reach Chiara’s House (or pay 1 euro for an elevator), but the sweeping vista is worth the effort. Every room looks out towards the deep blue sea.

Coloftseum in Rome

This loft offers everything you need for a stay in Rome. It’s located in the ancient neighborhood of Rione Monti, within walking distance of the Colosseum in a district loaded with excellent dining, drinking, and culture-seeking options.