Holiday houses in São Simão

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Top-rated holiday rentals in São Simão

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

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Superhost

Home in São Lourenço

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.

FamilyLocationOutdoor spaces

4.8 out of 5 average rating, 25 reviews

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

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.

ValueLocationSleep quality

4.99 out of 5 average rating, 104 reviews

Guest favourite

The outdoor area features a well-maintained swimming pool surrounded by lush greenery and tropical plants. Sun loungers are positioned next to the pool, providing a serene spot for relaxation. A gravel pathway leads through the garden, enhancing the tranquil atmosphere.

Villa in Quinta do Anjo

Charming place, beach + countryside, full privacy

Lovely and magical place, fully equipped and recently renovated. Big property, 1.100 m², with fantastic green areas and a very special and unique ambience at the swimming pool area. 100% privacy and very quiet. 15 km away from some of the most beautiful beaches of Portugal and breathtaking sceneries where nature reigns. Great gastronomy, top quality local products like fish, wine, cheese + many others. Small football pitch, table football + ping-pong. Distances: Lisbon 30 m. Airport 35 m.

ValueLocationOutdoor spaces

4.98 out of 5 average rating, 102 reviews

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 São Lourenço

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.

FamilyLocationNearby

5.0 out of 5 average rating, 49 reviews

Guest favourite

Home in São Lourenço

Casa da Arrábida | praias, natureza e tradição

Desfrute de uma estadia inesquecível no coração de Azeitão, entre as praias deslumbrantes da Arrábida, a beleza da serra e a autenticidade da gastronomia local. Ideal para famílias e grupos até 6 pessoas, a casa oferece todo o conforto necessário para relaxar e explorar uma das regiões mais bonitas de Portugal. A poucos minutos das melhores praias, adegas, trilhos e de Sesimbra, é o local perfeito para criar memórias especiais com quem mais gosta. Reserve já e descubra o melhor da Arrábida

ValueLocationAmenities

4.9 out of 5 average rating, 29 reviews

Top Guest favourite

A private heated pool is surrounded by a tiled patio, with potted plants and vibrant walls enhancing the space. Sun loungers and an umbrella provide relaxation options, while a spacious yard features greenery and nearby structures. Clear blue skies add to the inviting atmosphere of the outdoor area.

Tiny home in São Lourenço

Cafofos da Zeta, Cozy Pool House

Ligue-se à natureza nesta escapadela inesquecível. Perto da serra perto do mar. Vai adorar este espaço único com uma bela piscina (aquecida de Maio a Outubro ) privada e exclusiva. No telheiro pode fazer as suas refeições ou simplesmente relaxar numa rede brasileira a ler um bom livro ao som dos passarinhos. Temos um BBQ a gás para os seus grelhados com os utensílios necessários. Existe um recanto muito acolhedor com um fire pit (braseira) para momentos únicos e especiais de lazer.

FamilyLocationCondition

4.98 out of 5 average rating, 83 reviews

Guest favourite

A vibrant display of bougainvillea frames a window with white sheer curtains, set against a white wall. The window features green trim and a decorative wrought iron element. A bright yellow overhang highlights the architectural details.

Home in São Lourenço

Lisboa/Praias: Casa c/ terraço

Azeitão/Arrábida: Sua Escapada Perfeita! Descubra nossa charmosa casinha típica em Vila Fresca de Azeitão A casa possui dois quartos de casal e um terraço com vista, ideal para refeições ao ar livre. Está totalmente equipada com cozinha completa (frigorífico, micro-ondas, máquina de lavar louça e café), máquina de lavar roupa, TV e internet. A localização é imbatível: 27 km de Lisboa 12 km de Setúbal/Sesimbra A apenas 15 minutos das praias paradisíacas da Costa da Arrábida.

LocationQuietLong stay

4.95 out of 5 average rating, 22 reviews

Guest favourite

Home in São Lourenço

Casas de Azeitão - Piscina Privada, By Home Match

Viva uma escapadinha de sonho em Azeitão! Este alojamento exclusivo oferece o equilíbrio perfeito entre conforto e charme local. Refresque-se na piscina privativa, aproveite a praticidade das máquinas de lavar loiça e roupa, e estacione com total comodidade. A apenas 5 minutos do centro de Azeitão, 30 km de Lisboa e perto das praias mais deslumbrantes de Portugal. Um refúgio entre o mar, a serra e os sabores da região — ideal para momentos inesquecíveis!

LocationFamilyPool

4.96 out of 5 average rating, 27 reviews

Guest favourite

Home in São Lourenço

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 .

FamilyLocationPets

4.97 out of 5 average rating, 31 reviews

Guest favourite

Bungalow in São Lourenço

Casa Alzaitun, Azeitão with Heated Pool

Escape to this stunning 4-bedroom vacation home, perfect for families or groups looking for comfort and relaxation. Featuring an open-concept kitchen with modern appliances and a spacious living area, this home is designed for entertaining and unwinding.<br><br>Step outside to a private heated pool, ideal for year-round enjoyment, and a beautifully landscaped yard with space to relax or play.

FamilyLocationNearby

5.0 out of 5 average rating, 9 reviews

Guest favourite

An outdoor area is showcased, featuring a small pool and a lush olive tree. Two colorful hammocks are draped between the tree and the house, which has large sliding doors leading to the kitchen. A dining table and chairs are visible, creating a casual atmosphere.

Home in São Lourenço

Designed Retreat with Private Pool near Lisbon

Escape to a serene, family-friendly retreat with a private pool! This beautifully renovated home features seamless indoor-outdoor living with a sunny patio, BBQ, and a unique mezzanine lounge net. Located in a peaceful village just a 15-minute drive from stunning beaches and the Serra da Arrábida nature reserve. Perfect for families seeking comfort and relaxation.

LocationValueOutdoor spaces

4.98 out of 5 average rating, 147 reviews

Superhost

A covered outdoor seating area features a woven chair adorned with colorful cushions. A small table sits nearby, while a tranquil dipping pool gleams under natural light. Lush greenery and potted plants surround the space, creating a serene atmosphere for relaxation.

Cottage in São Lourenço

Cosy Country House

This house is inserted in a private villa and the place is calm and secure. The house is fully equiped with all kitchen facilities for 2 or 3 people. You can enjoy the country side air, take a bike walk, go to beach, or just relax.

FamilyLocationHiking

4.67 out of 5 average rating, 73 reviews