Three weeks in each villa — enough time to stop being a tourist and start being a temporary local. A pool in the olive groves of Puglia. A hilltop in the Valdarno with a winery next door.

Villa Saracena pool and olive grove, Ostuni
Part One  ·  Puglia
Villa Saracena
Ostuni, Apulia  ·  Hosted by Andrea
May 11 – June 1  ·  21 nights
A luxury villa nestled in a hectare of ancient olive grove, a few minutes from Ostuni's whitewashed centro storico and the Adriatic coast. Private pool, outdoor kitchen, and the kind of property that makes leaving feel like a mistake.
Guests
Up to 8
Bedrooms
4 bedrooms · 4 baths
Pool
Private · 10×4m
Rating
★ 5.0  (4 reviews)
🏊 Private pool 🌿 Olive grove 🍳 Full kitchen 🔥 BBQ / outdoor kitchen ❄️ A/C 📶 WiFi 🚗 Gated parking 🐾 Pets allowed
View on Airbnb
Tourist tax: €2/person/night, collected in cash at check-in. Host Andrea will verify all guest documents. Extra services available (cleaning, chef, linen change) — ask directly.
Villa near Arezzo, Pergine Valdarno, Tuscany
Part Two  ·  Tuscany
Villa Pergine Valdarno
Pergine Valdarno, Arezzo  ·  Valdarno di Sopra
June 1 – 22  ·  21 nights
A hilltop villa in a tiny medieval village in the Valdarno, between Florence and Arezzo. Vini Guerrini — a working winery — is literally next door at Via Querceto 24. The rest of Tuscany is within an hour's drive.
Guests
Up to 8
Location
Via Querceto 26
Nearby
Arezzo 15 km · Florence 50 km
Winery
Next door (Vini Guerrini)
🏊 Pool 🍷 Winery next door 🏔 Valdarno views 🍳 Full kitchen 📶 WiFi 🚗 Parking
View on Airbnb
Medieval hilltop village — small enough that after a few days you'll know the bar owner and the baker. Friday morning market in the village square is a weekly ritual.