Section I · The Ranked Twelve
From best to twelfth.
Sorted by what each pocket actually does well at its price point, on the peak summer week.
No. I
Restored masseria estate, olive groves north of Ostuni, seven-bedroom.
Bedrooms: 7. Sleeps: 14. Pocket: the olive groves north and west of the white town. Setting: restored farm estate on acreage, large pool, outdoor kitchen, short drive to town and sea. Peak weekly rate: €42,000 to €70,000 / wk peak summer, listed through The Thinking Traveller and Le Collectionist. Included: daily housekeeping, concierge, large pool, air-conditioning, gardens, welcome provisioning. Not included: a beach at the door, a walk to the town, true seclusion from neighbouring estates in August.
Why it ranks here: the trophy pocket of Ostuni. The restored masseria in the olive groves is what the destination does better than anywhere in the region: a private farm estate with the dry-stone walls, the old trulli, a serious pool, and the space for a group of 14 to spread out, with both the white town and the coast a short drive away. For the full Puglia estate experience, nothing else here matches it.
What we would change: the masserie sit in working countryside, so a car is essential for every dinner and every beach, and the nearest grocery is a drive. The land and the pool are the draw; the car dependence is the trade.
Get the free villa buyer’s guide
No. II
White-town-edge villa with sea-view terrace, six-bedroom.
Bedrooms: 6. Sleeps: 12. Pocket: the slopes just outside the centro storico. Setting: contemporary or restored villa with pool and a terrace looking over the white town to the sea. Peak weekly rate: €30,000 to €56,000 / wk peak summer, listed through The Thinking Traveller and Exceptional Villas. Included: housekeeping, concierge, pool, air-conditioning, the town view. Not included: the acreage of a masseria, a beach on foot, full seclusion.
Why it ranks here: the best-of-both pick. A villa on the edge of the white town gives a group of 12 the walk into the centro storico for dinner and the famous view of the lime-washed houses, with a pool and the sea on the horizon. Right for a group that wants the town close without the full countryside drive.
What we would change: the town-edge plots are smaller than the masserie, so the privacy and the land are less. The view and the walkability are the draw; the tighter plot is the trade.
Get the free villa buyer’s guide
No. III
Rosa Marina gated coastal villa, six-bedroom.
Bedrooms: 6. Sleeps: 12. Pocket: Rosa Marina, the gated pine-and-coast community below Ostuni. Setting: villa among the pines, pool, short walk or drive to the rocky coves. Peak weekly rate: €26,000 to €48,000 / wk peak summer, listed through SopranoVillas and The Thinking Traveller. Included: housekeeping, concierge, pool, air-conditioning, gated security. Not included: the white-town view, the masseria acreage, a sandy beach at the door.
Why it ranks here: the coast-and-gate pick. Rosa Marina is the established gated community on the coast below Ostuni, with controlled access, pine shade, and the limestone coves within reach, so a villa here keeps the sea close for a group of 12 that prizes beach days over countryside. The gated calm is the draw.
What we would change: Rosa Marina fills up in August and the coves are rock-and-platform rather than long sand, so confirm the swimming suits the group. The gate and the coast are the draw; the summer crowd is the trade.
Get the free villa buyer’s guide
No. IV
Valle d’Itria trullo-and-masseria villa toward Cisternino, six-bedroom.
Bedrooms: 6. Sleeps: 12. Pocket: the Valle d’Itria, inland toward Cisternino and Locorotondo. Setting: restored complex of trulli and masseria buildings, pool, olive groves. Peak weekly rate: €24,000 to €46,000 / wk peak summer, listed through The Thinking Traveller and Le Collectionist. Included: housekeeping, concierge, pool, air-conditioning, the trulli architecture. Not included: a quick run to the coast, the white-town setting, a single-building layout.
Why it ranks here: the architecture pick. The Valle d’Itria is the heart of trulli country, and a restored complex here gives a group of 12 the conical-roofed buildings, the inland villages of Cisternino and Locorotondo, and a deeply rural calm. Right for a group that wants the Puglia of the postcards over the beach.
What we would change: the inland position puts the coast 25 to 35 minutes away, so this is a countryside week, not a beach week. The architecture and the calm are the draw; the distance to the sea is the trade.
Get the free villa buyer’s guide
No. V
Costa Merlata and Pilone coast villa, five-bedroom.
Bedrooms: 5. Sleeps: 10. Pocket: the Costa Merlata and Pilone stretch of the Adriatic coast. Setting: villa near the limestone coves, pool, short walk to the sea. Peak weekly rate: €22,000 to €42,000 / wk peak summer, listed through SopranoVillas and Exceptional Villas. Included: housekeeping, concierge, pool, air-conditioning, coast access. Not included: gated seclusion, the masseria land, the white-town view.
Why it ranks here: the closest-to-the-sea pick. The Costa Merlata and Pilone coves are some of the prettiest swimming on this stretch, and a villa here puts a group of 10 within a short walk of the water with the town a quick drive up the hill. Right for a group that wants the beach above all.
What we would change: the coast road is busy in high summer and the swimming is off rock and platform, so confirm the access. The proximity to the sea is the draw; the summer traffic is the trade.
Get the free villa buyer’s guide
No. VI
Carovigno countryside villa near Torre Guaceto, five-bedroom.
Bedrooms: 5. Sleeps: 10. Pocket: the countryside around Carovigno, near the Torre Guaceto marine reserve. Setting: villa in the olive groves, pool, a drive to the protected reserve beaches. Peak weekly rate: €20,000 to €38,000 / wk peak summer, listed through The Thinking Traveller and SopranoVillas. Included: housekeeping, concierge, pool, air-conditioning, gardens. Not included: beach frontage, the white-town setting, a walk to a restaurant.
Why it ranks here: the nature-reserve pick. Carovigno sits beside the Torre Guaceto marine reserve, where the protected dunes and clear water are the best natural beaches in the area, so a villa here gives a group of 10 the countryside calm and a short drive to a rare unspoilt coast. Right for a group that wants the reserve.
What we would change: the reserve beaches are protected, so access is regulated and parking is limited in peak August. The unspoilt coast is the draw; the access rules are the thing to plan for.
Get the free villa buyer’s guide
No. VII
Contrada infinity-pool villa in the olive groves, five-bedroom.
Bedrooms: 5. Sleeps: 10. Pocket: a contrada in the olive-grove countryside around Ostuni. Setting: contemporary villa with an infinity pool over the groves toward the sea. Peak weekly rate: €20,000 to €36,000 / wk peak summer, listed through Exceptional Villas and SopranoVillas. Included: housekeeping, concierge, infinity pool, air-conditioning, gardens. Not included: the historic masseria character, a beach on foot, a walk to town.
Why it ranks here: the modern-design pick. For a group of 10 that wants a clean contemporary villa with a serious infinity pool rather than an old farm estate, the contrada new-builds in the olive groves deliver the view and the pool at a rate below the trophy masserie. Right for a design-led group.
What we would change: a new villa lacks the history and the dry-stone character of a restored masseria, which is much of Puglia’s appeal. The pool and the design are the draw; the missing patina is the trade.
Get the free villa buyer’s guide
No. VIII
Ceglie Messapica countryside masseria, five-bedroom.
Bedrooms: 5. Sleeps: 10. Pocket: the countryside around Ceglie Messapica, inland from Ostuni. Setting: smaller restored masseria, pool, olive groves, near the food town of Ceglie. Peak weekly rate: €18,000 to €34,000 / wk peak summer, listed through The Thinking Traveller and Le Collectionist. Included: housekeeping, concierge, pool, air-conditioning, gardens. Not included: a quick coast run, the white-town view, a large estate footprint.
Why it ranks here: the gastronomy pick. Ceglie Messapica is one of Puglia’s recognised food towns, and a masseria here gives a group of 10 the countryside calm with serious restaurants close at hand. Right for a group that puts the table first.
What we would change: Ceglie is further inland, so the coast is a 30-minute drive and this is a countryside-and-food week. The dining and the calm are the draw; the distance to the sea is the trade.
Get the free villa buyer’s guide
No. IX
Lido Morelli beach-access villa, four-bedroom.
Bedrooms: 4. Sleeps: 8. Pocket: Lido Morelli and the sandy stretch of the Ostuni coast. Setting: villa near one of the area’s few sandy beaches, pool, short walk to the sand. Peak weekly rate: €16,000 to €30,000 / wk peak summer, listed through SopranoVillas and Exceptional Villas. Included: housekeeping, pool, air-conditioning, beach access. Not included: full staff, gated seclusion, the masseria land.
Why it ranks here: the sandy-beach value pick. The Ostuni coast is mostly rock, so the sandy stretches near Lido Morelli are prized, and a villa here gives a group of eight actual sand within a short walk at a rate below the estates. Right for a family that wants the beach over the countryside.
What we would change: the sandy lidi are popular and lined with beach clubs, so the immediate area is lively in August. The sand is the draw; the summer busyness is the trade.
Get the free villa buyer’s guide
No. X
San Vito dei Normanni village-edge villa, four-bedroom.
Bedrooms: 4. Sleeps: 8. Pocket: the edge of San Vito dei Normanni, the working town west of Ostuni. Setting: villa with pool near the village, olive groves around. Peak weekly rate: €15,000 to €28,000 / wk peak summer, listed through SopranoVillas. Included: housekeeping, pool, air-conditioning, gardens. Not included: the white-town setting, a beach on foot, full staff.
Why it ranks here: the walk-to-real-life pick. A villa on the edge of San Vito dei Normanni gives a group of eight a pool and the groves with a genuine working town and its shops and bakeries on foot, at a rate below the Ostuni-edge properties. Right for a group that wants the everyday Puglia close.
What we would change: San Vito lacks the postcard looks of the white town, so the immediate setting is workaday rather than scenic. The convenience and the rate are the draw; the plainer surroundings are the trade.
Get the free villa buyer’s guide
No. XI
Small restored masseria with chapel, four-bedroom.
Bedrooms: 4. Sleeps: 8. Pocket: the olive-grove countryside around Ostuni. Setting: smaller restored masseria with its own chapel, pool, walled garden. Peak weekly rate: €15,000 to €27,000 / wk peak summer, listed through The Thinking Traveller. Included: housekeeping, pool, air-conditioning, the chapel and garden. Not included: a large group footprint, a beach on foot, full staff.
Why it ranks here: the character-at-a-lower-rate pick. A smaller masseria with its own chapel gives a group of eight the historic Puglia character, the dry-stone walls, and the walled garden at a rate well below the large estates. Right for a smaller group that wants the masseria feel.
What we would change: at four bedrooms the footprint is tighter, so a larger group would feel the squeeze. The character is the draw; the size is the trade.
Get the free villa buyer’s guide
No. XII
Historic-centre palazzo, white town, four-bedroom.
Bedrooms: 4. Sleeps: 8. Pocket: within the white-town walls of the centro storico. Setting: restored palazzo or townhouse, roof terrace, no pool, walk-everywhere. Peak weekly rate: €14,000 to €26,000 / wk peak summer, the floor of this list, listed through SopranoVillas. Included: housekeeping, air-conditioning, roof terrace, the walkable town. Not included: a pool, a garden, parking at the door.
Why it ranks here: the walk-everywhere entry at the floor of the band. A restored palazzo inside the white town puts a group of eight in the lanes, steps from the restaurants and the views, at the lowest rate on this list. Right for a group that wants to live in the town rather than drive to it.
What we would change: at this price and setting there is no pool and no parking at the door, and the white town heats up in August. The walkability is the draw; the missing pool and the parking are the trade.
Get the free villa buyer’s guide