Discover the best holiday rentals: self-catering villas, charming holiday homes and unique apartments Pico

The beauty of staying in a holiday home lies in the rhythm you set for yourself. Whether it's a minimalist beach house, a secluded stone cottage or a design-led villa with sweeping views, these spaces offer the freedom to live like a local, but with more style, privacy and intention, be it for couples, families or groups of friends. At Secretplaces, we seek out holiday homes and villas that stand out for their architecture, ambience and setting — places where the materials matter, the light is right, and the atmosphere invites calm. From refined apartments in historic cities to countryside retreats framed by olive groves, our handpicked selection goes beyond the functional. These are spaces with soul. Whether you're preparing a slow breakfast in a sunlit kitchen, enjoying the quiet of a mountain chalet, or watching the sea change colour from a villa with a pool, the essence is always the same: considered design, a sense of place, and the luxury of simplicity Each place in our collection has been handpicked for its style, soul, and sense of place.


Boutique holiday homes, villas, and self-catering apartments — curated with care:

  • Cottages
    The Adegas do Pico are a group of thirteen traditional stone country houses located in Praínha, on the north coast of the island of Pico, where guests can enjoy the hospitality and traditional feel of Azorean life. Twelve wineries full of joy, good times, affection and eternal memories.
    • Seaside (ocean front)
    • |
    • 12 properties
    • |
    • from 75 EUR info
  • Holiday home villa
    This stunning, newly constructed luxurious villa by the sea boasts 4 en-suite bedrooms, a private outdoor heated infinity pool, Jacuzzi and an idyllic and tranquil location in the historic village of Criação Velha. Set in the natural beauty of the Azores the villa offers a romantic retreat, a family getaway, or a relaxing and meditative getaway that helps you unwind and forget the stresses of modern life.
    • Seaside (ocean front)
    • |
    • 8 people
    • |
    • from 400 EUR info
  • Cottage
    Casa do Chorão is an old stone country house by the sea in S. Miguel Arcanjo, with a large living room with panoramic windows (views of the sea and the island of S. Jorge), one double bedroom, bathroom with shower and outdoor living space. This local accommodation is available from April to October.
    • Countryside
    • |
    • 4 people
    • |
    • from 100 EUR info
  • Holiday home villa
    Monte Branco is a holiday home offering excellent views of the Sea and Mountain and the Azores Green with the island of São Jorge as a backdrop. From the porches you see Pico Mountain on one side and the ocean on the other. The interior offers a cozy atmosphere with wooden elements.
    • Seaside (ocean front)
    • |
    • 4 people
    • |
    • from 115 EUR info
  • Cottage
    Sea U Pico is a charming farmhouse located in São Roque do Pico, Azores, Portugal. This accommodation offers amazing ocean views and a serene atmosphere, perfect for nature lovers and those seeking a peaceful escape. The property combines rustic charm with modern amenities, providing a comfortable and relaxing environment.
    • Seaside (ocean front)
    • |
    • 6 people
    • |
    • from 181 EUR info
  • Holiday home villa
    The building of Art of Escape offers contemporary architecture with views of the sea. Located on the south coast of the Island, in the guardian shade of the mountain. This charming modern country home has 3 suites (2 pairs and 1 twin), large living rooms, terraces, barbecue and garden of orange trees and incense.
    • Countryside
    • |
    • 6 people
    • |
    • from 500 EUR info
  • Holiday Apartments
    Located on Pico Island in the Azores, this 4-star country hotel is part of the Ramal do Calhau Wine Tourism Project in the town of Madalena. With spacious apartments, a welcoming reception and breath-taking views, Vinhas do Calhau will be your home away from home in the Azores and is sure to bring the essence of Pico to its visitors: a starting point for exploring and discovering the island.
    • Seaside (ocean front)
    • |
    • 6 properties
    • |
    • from 110 EUR info
Our short listed lodgings
Below you will find some more lovely accommodations we have recently discovered and that we will publish soon. You can book them through booking.com in the meantime.
  • Holiday homes villas
    The cottages in Pontas Negras are a peaceful retreat surrounded by natural beauty and traditional Azorean architecture. The interiors of these small villas feature parquet floors, fireplaces and balconies with stunning mountain views that merge with the sea. Enjoy a delicious breakfast, relax by the pool with sun loungers and explore the natural wonders of the beautiful island of Pico.
    • Seaside (ocean front)
    • |
    • 8 rooms
    • |
    • from 220 EUR info

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