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House holiday rentals in São Simão

Find and book unique houses on Airbnb

Top-rated house rentals in São Simão

Guests agree: these houses are highly rated for location, cleanliness and more.

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Top guest favourite
A spacious garden area is visible, featuring a serene infinity pool bordered by sun loungers and palm trees. Lush greenery surrounds the pool, while ocean views extend in the background under a clear sky.
Home in Alcabideche
4.86 out of 5 average rating, 297 reviews

Charme & Design em Casa com Piscina e Vista Magnífica de Mar e Montanha

Observe os “melros” pela manhã, o pôr do sol, desfrute da calma e tranquilidade. Aproveite a vista única de mar e montanha do lounge privado, a piscina infinita, a “Serra de Sintra”-a montanha mágica, os seus bosques encantados, conventos e palácios. Possibilidade de incluir uma mesa de trabalho. Existe também a possibilidade de aceitar celebrações de casamentos, caso seja de pequenos grupos, mediante pagamento suplementar. Para mais informações contatar diretamente com o anfitrião. Uma Villa de montanha construída à mais de 100 anos , implantada sobre uma imponente rocha com uma envolvente única e uma vista de cortar a respiração sobre o mar a cidade , Cascais e a montanha onde está inserida . A casa foi remodelada recentemente e ampliada com uma construção moderna e de design desfrutando da vista e da envolvente . Vê-se desde o topo da Serra de Sintra, ao Guincho ao Cabo Espichel. A dois passos dos percursos pedestres da Serra de Sintra e dos seus monumentos e junto de bons restaurantes , de cafés com bom ambiente , a pequena aldeia tem supermercado e farmácia para sua tranquilidade. Os hóspedes têm à sua disposição uma casa com 2 quartos, sala e cozinha, totalmente privativa e acesso a um grande jardim com uma piscina infinita onde podem desfrutar da maravilhosa vista. Moro na propriedade e estou disponível para partilhar histórias e informações sobre a região. Adoro ciclismo e conheço a Serra como a palma da minha mão. Posso partilhar os segredos da serra e aconselhar os melhores restaurantes da região. Malveira da Serra, aldeia pitoresca junto a Cascais e Lisboa (20 min), com percursos pedestres na Serra de Sintra e seus monumentos. A Praia do Guincho e as suas dunas selvagens com a sua beleza única, são um paraíso para o Surf/Kite-surf/Windsurf. Aconselho o uso de carro próprio.

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Home in União das freguesias de Azeitão (São Lourenço e São Simão)
4.83 out of 5 average rating, 18 reviews

Villa Vintage: Vineyards & Historic Center Azeitão

Discover this charming villa, a haven of soul and character in the heart of Azeitão. Surrounded by winemaking tradition and the serenity of the Arrábida Mountains, it invites you to slow down and savor each moment. Just 5 min. from the iconic Bacalhôa and José Maria Fonseca wineries and 18 min. from the stunning beaches of Galapinhos and Portinho, it’s ideal for sharing meals, peaceful swims, and genuine moments. Spacious, full of light, and perfect for those who value comfort with personality.

Top guest favourite
An aerial view captures a heated plunge pool nestled in a wooden deck area, surrounded by lush greenery. Comfortable sun loungers and wicker chairs invite relaxation, while vibrant pink flowers enhance the serene atmosphere of the private space.
Home in União das freguesias de Cascais e Estoril
4.98 out of 5 average rating, 179 reviews

Amazing Pool Pavilion with Private Heated Pool

The Pool Pavilion is a cosy and relaxed two suites and kitchen space that overlooks a lush garden and is the ideal choice for a joyful and relaxing getaway. Appointed to a high standard with simple yet sophisticated materials, such as micro cement flooring , stucco walls and linen curtains, and decorated in soothing natural colours, it blends harmoniously with its surroundings. Large patio doors lead out onto a spacious, private garden with wood decking, a heated pool, sun loungers and table.

Top guest favourite
A spacious terrace reveals panoramic views of the Atlantic Ocean and the Tróia peninsula. A wooden table is centered beneath a bamboo awning, with potted plants adding a touch of greenery. Seaside vistas create a serene atmosphere for relaxation.
Home in Setúbal
4.99 out of 5 average rating, 97 reviews

Panoramic views of ocean, city & São Filipe castle

Arriving at Olival de São Filipe means first stopping to take in the view. The high location of the seven-hectare estate provides rich vistas. “Even more beautiful than in the pictures”, is a frequently heard response. The panorama is varied and changes constantly under the influence of the sun, clouds and water. You look out over the Atlantic Ocean, the Tróia peninsula - with a sandy beach as far as the eye can see - the Fort of São Filipe, the mouth of the Sado river and the city of Setúbal.

Top guest favourite
A bright living space features large open doors, providing a panoramic view of the ocean and surrounding mountains. Natural light fills the room, which contains two rattan chairs positioned on a polished wooden floor, with lush greenery visible in the background.
Home in União das freguesias de Azeitão (São Lourenço e São Simão)
5 out of 5 average rating, 44 reviews

Cabana Do Portinho da Arrábida

Mountain Chalet, crafted entirely from wood, presents a blend of mountain and seaside serenity with walking distance from the beach! Accessible by foot (181 steps) or via a vehicle operated by staff for check in and out, the house guarantees absolute privacy. Each bedroom offers panoramic ocean vistas, ensuring every awakening is as breathtaking as the view. With relaxation at its core, the chalet offers an escape, where the hustle of cars are replaced by the smoothing presence of nature.

Top guest favourite
A warm living space features a large red sofa and a small wooden chair. The room is enhanced by a light-colored wooden floor and natural light flooding in through tall windows. A low coffee table is placed on a green area rug, with a small vase at its center.
Home in Sintra
4.98 out of 5 average rating, 342 reviews

Beautiful apartment w/ fabulous views!Free Parking

This beautiful apartment is part of the charming house Cerrado dos Pinheiros. Located in an exclusive area close to the historical center of Sintra with only a short walk from everything you need and easy access to Lisbon, beautiful beaches and peaceful countryside. The house was recently renovated offering modern facilities, whilst maintaining the original historical aspect. It's a perfect retreat for families, couples and friends who are looking for a private and peaceful place to stay.

Guest favourite
A charming beach house features a blue exterior with white shutters and a welcoming front deck. Unique seating options include two vibrant yellow bean bags and a woven chair, inviting relaxation. A canopy provides shade above a small outdoor table and chairs, enhancing the coastal atmosphere.
Home in Costa da Caparica
4.95 out of 5 average rating, 190 reviews

Traditional Beach House a few minutes from Lisbon

This house has been completely renovated and it´s located on the beach, facing the Atlantic Ocean. The beach has its own lifeguards who watch the beach during the summer. We are 10 min away from the center on foot through the beach or 2 min by train. In the center you find laundries, supermarkets, pharmacies, health centers, restaurants, etc. You can rent a bicycle or a car and take a tour. We are about 20 min from Lisbon and from the airport and about 15 min from the Hospital by car.

Guest favourite
A charming white structure features large arched windows, bringing natural light into the space. Two inviting chairs are positioned on the wooden deck outside, surrounded by lush greenery and rustic stone paths. The sloping roof is accented by traditional tiles, enhancing the home’s character.
Home in Setúbal
4.94 out of 5 average rating, 18 reviews

Arrábida Getaway • Jacuzzi & Mountain Views

Once a charming tea house, this cozy studio is a peaceful retreat on a private family farm in the heart of Arrábida Natural Park — with total privacy, yet just minutes from Setúbal’s historic centre and stunning beaches like Portinho da Arrábida and Galápagos. Outside, hike or bike limestone trails with Atlantic views, kayak and snorkel in crystal-clear waters, sip Moscatel at local wine quintas, or browse the iconic Mercado do Livramento for fresh fish and regional produce.

Top guest favourite
A private terrace is showcased with a small blue table and matching chairs, overlooking the ocean. Lush greenery surrounds the seating area, highlighting a well-kept outdoor space. The bright blue sea contrasts with the clear sky, creating a serene atmosphere.
Home in Colares
4.94 out of 5 average rating, 109 reviews

Cliffside Casita (1BR) · Breathtaking Ocean Views

OUTPOST - Ocean Casitas One of the four Ocean Casitas, at the very top of the whitewashed fishermen's village of Azenhas do Mar with a large private terrace right to the edge of the cliff. 

 Originally traditional fishermen’s homes, the casitas have been carefully rebuilt to combine their original charm with contemporary design, including open layouts, micro-cement floors and ceilings up to 5 meters high. A calm, stylish space designed for a relaxed coastal stay.

Top guest favourite
Home in União das freguesias de Azeitão (São Lourenço e São Simão)
4.96 out of 5 average rating, 24 reviews

Serra da ursa

Refúgio exclusivo entre 6 hectares de vinhas, ideal para relaxar e reconectar com a natureza. Moradia única com piscina aquecida todo o ano, vista panorâmica e pôr do sol de tirar o fôlego. A poucos minutos das praias deslumbrantes da Arrábida e no coração da rota dos melhores vinhos de Setúbal. Um lugar mágico, onde cada detalhe convida à tranquilidade. Viva momentos inesquecíveis num cenário que parece um filme .

Top guest favourite
Two wooden lounge chairs with light fabric seats are positioned on a stone patio, facing the ocean. A large, lush green tree is visible in the background, alongside the sparkling blue waters of the sea, creating a serene outdoor setting.
Home in União das freguesias de Azeitão (São Lourenço e São Simão)
5 out of 5 average rating, 26 reviews

Casa do Portinho

Welcome to our ocean view paradise! Our ocean view house offers a truly unforgettable getaway for those seeking tranquility, and natural beauty. With its prime location in the Arrábida National Park, overlooking the sparkling azure waters of the ocean, this property promises and idyllic retreat for your Airbnb stay. Closest beach (Praia de Alpertucho, 5/10min walk) Praia do Creiro, 15/20min walk

Top guest favourite
A coastal terrace is viewed from the stone-paved area, showcasing lush greenery, terracotta planters, and an expansive view of the ocean. A red sailboat can be seen gently moving across the water, while the sky above is clear and bright.
Home in Colares
4.96 out of 5 average rating, 154 reviews

Restored winery on the Atlantic.

Historic late 17th century winery newly restored into home. Situated on the Atlantic Ocean with views of the beautiful Coastal village of Azenhas do Mar, Cabo da Roca and Ericeira. Walking distance to Praia das maçãs and Azenhas do Mar beach. Breathtaking views from either window of the home. More information available upon request. A rare property in a unique location.

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