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Holiday houses in São Simão

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Top-rated holiday rentals in São Simão

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Guest favourite
An inviting outdoor terrace extends from the living area, featuring a mix of wooden chairs and a dining table. A modern stone fireplace is visible, softly illuminated by warm lighting beneath a high, wooden-beamed ceiling. Lush green grass surrounds this cozy outdoor space.
Chalet in Azeitão
4.95 out of 5 average rating, 114 reviews

Stunning Countryside Chalet

Quinta da Arrabida – Stunning countryside retreat near magnificient beaches with small pool Quinta da Arrábida – Indoor surface area: 200m2 Quinta da Arrabida: Villa for 8 to 10 people 4 Bedrooms, 4 bathrooms Spectacular living areas, open plan design rooms 8,9ha of private grounds, large terraces, and a small pool for children Surface area: 200m2 – 8,9 hectare private estate Quinta da Arrabida is located near the village of Casais da Serra, the nearest village to the spectacular Portinho da Arrabida beach (7km), set deep within the Serra da Arrabida Nature Park, halfway between the towns of Sesimbra and Azeitão, boasting magnificent and unique views throughout. Daylight pours from every angle into this beautiful designer villa, built on a single floor. The large living room and most bedrooms are fitted with extra large all glass wide doors, so every guest enjoys the unique mountain and green views on every occasion. The open plan living room is exquisitely decorated: centered around a lovely encased fireplace, each piece of furniture has been carefully picked to create a very exclusive country-chic environment, with the unique backdrop of the Arrabida Mountain Range always in mind. The living room opens onto a large terrace fitted with an outdoor dining table next to a barbecue unit, two hammocks and a mattress, entertainment provided by satellite TV, hifi stereo system and wireless internet. All four bedrooms and the four bathrooms were designed and decorated with the same basic principle in mind: to make the most from the surrounding nature, and the pictures speak for themselves. The master suite has a lovely walk-in shower and a dressing area; and opens onto the gardens via the same large all glass doors from two different angles. The second bedroom has two single beds and the third four bunk beds. These two bedrooms share a bathroom. The fourth bedroom has two single beds and en-suite bathroom. A small swimming pool can be fitted within the gardens, providing refreshment for the elder and endless hours of fun for the younger ones. The private grounds of the Quinta are the ideal place to enjoy nature, bird watching and long walks in unspoiled surroundings, beneath historic vineyards, all in close proximity to spectacular beaches. SETTING : Large private grounds in Arrabida National Park – 40 km South of Lisbon Location : Quinta da Arrabida is set in a 8,9 hectare private property, located deep in the Serra da Arrabida Nature Park, 7 Km away from magnificent beaches. 5 Km away is Vila Nogueira de Azeitao – a small historic town surrounded by the national park – well known for its vineyards, local culture, and wine cellars open to the public. Arrabida beach is considered one of the most beautiful beaches in Portugal and Europe, and boasts a natural bay with calm waters, ideal for swimming and snorkeling. The Serra da Arrabida Nature Park was established to protect the beautiful landscape and rich variety of wild life, including eagles, wildcats and badgers. The surrounding mountains are the perfect place to go for a walk, and excursions can be organised with the local nature tour companies. Getting there and around : Two hours flight from most European cities and seven from New York, the villa is reached by car from Lisbon Airport in 45 minutes. A car is essential for this holiday as there is no public transport to the villa. ACTIVITIES AND ATRACTIONS : Gastronomy and Wine tasting : The region of Azeitão is famed for its gastronomy, and even the local supermarket, Intermarché, has a mix of gourmet and standard products. The local gastronomic festival is held from June to September. Fresh grilled fish is an inexpensive delight. Five formal wine routes have been devised in the Setubal peninsula by the ‘Rota de Vinhos’ association, combining wine tasting with sightseeing, arts and nature. The villa is ideally situated to take best advantage of these delights of the area. Local delights include cheeses, pastries, and obviously a very thorough wine culture. Beaches : The villa is located near many sandy beaches, all with different characteristics. Portinho da Arrabida (7km away) is among the most beautiful beaches in Europe. Praia das Bicas (a popular surf spot), Praia da Foz and Praia do Meco are all within a short drive, as well as the unique Troia Peninsula across the Sado Estuary. Golf Information : Quinta do Peru and Aroeira Clube de Campo are both a short drive (10km) from the villa. Tróia Golf (a short drive and a ferry ride) is a difficult course but one of the most beautiful in Portugal. Other options are available nearby such as Ribagolfe, Montado or Aldeia dos Capuchos.

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 Cascais
4.86 out of 5 average rating, 272 reviews

Charm & Design in a House with a Pool and Magnificent View of the Sea and Mountains

Observe the “blackbirds” in the morning, the sunset, enjoy the calm and tranquility. Enjoy the unique view of the sea and mountain from the private lounge, the infinity pool, the “Serra de Sintra”-the magical mountain, its enchanted woods, convents and palaces. Possibility to include a work desk. There is also the possibility of accepting wedding celebrations, if you are small groups, for an additional fee. For more information contact the host directly. A mountain villa built more than 100 years ago , implanted on an imposing rock with a unique surroundings and a breathtaking view over the sea the city , Cascais and the mountain where it is inserted . The house was recently refurbished and enlarged with a modern and design construction enjoying the view and surroundings . You can see it from the top of the Serra de Sintra, to Guincho to Cabo Espichel. A stone's throw from the pedestrian paths of the Serra de Sintra and its monuments and next to good restaurants , cafes with good atmosphere , the small village has a supermarket and pharmacy for your tranquility. Guests have at their disposal a house with 2 bedrooms, living room and kitchen, totally private and access to a large garden with an infinite pool where they can enjoy the wonderful view. I live on the property and am available to share stories and information about the region. I love cycling and know the Serra like the back of my hand. I can share the secrets of the mountains and advise the best restaurants in the region. Malveira da Serra, picturesque village next to Cascais and Lisbon (20 min), with hiking trails in Serra de Sintra and its monuments. Guincho Beach and its wild dunes with their unique beauty are a paradise for surfing/kite-surfing/windsurfing. I advise you to use your own car.

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, 79 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.

Guest favourite
A welcoming dining area is visible, furnished with a round wooden table set for four. Soft lighting from hanging fixtures complements the natural light streaming through nearby windows. A comfortable seating area with a neutral sofa is positioned against a textured wall, adding warmth to the space.
Apartment in São Lourenço
4.91 out of 5 average rating, 23 reviews

Loft de Charme in Azeitão

Loft de Charme in the typical village of Vila Nogueira de Azeitão Comfortable and fully rehabilitated Near all the trade and services and 100 meters from bus stops to the beaches of Sesimbra and Figueirinha. Extremely welcoming and refined place with unparalleled decoration. 5 minutes' walk to: Parque Natural da Serra da Arrábida; Adega; Intermarche; Restaurants; Bares. By car: 45 minutes from Lisbon; 20 minutes from Setúbal; and 20 minutes from Sesimbra. SAE - Sonho Azeitão Envolvente

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 Azeitão
5 out of 5 average rating, 35 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
An outdoor patio area features a private pool surrounded by a stone terrace. A spacious dining table with six chairs is positioned adjacent to a barbecue area. Comfortable seating is provided by two lounge chairs and a shaded corner sofa.
Villa in Quinta do Conde
4.98 out of 5 average rating, 110 reviews

Villa with pool and Jacuzzi, 30 km from Lisbon

Welcome to Quinta do Conde, located 30km from Lisbon, 18km from Sesimbra Beach and Portinho da Arrábida! Located minutes from the Motorway for access to Lisbon, Comboios Coina Station, Shopping, Green Spaces and easy access to the Quinta do Perú Golf Course. A 2 minute drive away is the Lidl Supermarket, among others and Pharmacy. A 25-minute drive, there is Setubal, with access to Tróia by ferry, and beaches such as Caparica, Lagoa de Albufeira, Sesimbra and the Cabo Espichel Lighthouse!

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 Setúbal
4.99 out of 5 average rating, 134 reviews

Outdoor, modern, beach and tranquility

WINTER MONTHS The house has central heating. A very efficient floor heating system keeps the house warm. You will not be cold, we guarantee it! Modern small house with outdoors, small pool and a 15 minute ride to the beaches. Recently renovated, a sliding door from the kitchen to the outdoor to take full advantage of the country's beautiful weather. Located near walking and bike paths of the Serra da Arrabida. Out of the ordinary. No airbnb services are allowed in our house at any time.

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 Setúbal
4.99 out of 5 average rating, 76 reviews

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.

Top Guest favourite
The exterior of a historic windmill is showcased, featuring a circular white structure with a blue base. Lush greenery surrounds the base, with palm trees and shrubs visible. A clear blue sky offers a background to the picturesque setting, while the ocean can be seen in the distance.
Windmill in Setúbal
4.98 out of 5 average rating, 257 reviews

Moinho do Marco: the romantic windmill hideaway

Let yourself be carried away by the romanticism of the Moinho do Marco! Built in 1855, it is one of the few that still retains its original wooden gears. Enjoy the magic of sleeping comfortably in a mill full of history and charm. Located in the Serra da Arrábida, let yourself be conquered by the tranquillity of nature from the terrace, which offers the best view over the beautiful Bay of Setúbal. Enjoy this unusual, romantic and sustainable accommodation at any time of the year.

Top Guest favourite
A bright and airy living space features a comfortable gray sofa adorned with decorative cushions. A television is positioned on a white media console, while a small table holds a potted plant. Framed art pieces line the light-colored walls, and natural light filters through large windows.
Apartment in Setúbal
4.99 out of 5 average rating, 215 reviews

Nice flat in Setubal - Homevolution

Renovated and fully equipped 1-bedroom apartment in a quiet residential area of Setúbal. We have AC in the living room/kitchen (unique space) and in the bedroom. The windows (double glazed) are new, allowing for heat/cold and noise insulation. The kitchen is new: refurbished in December 2023. Close to Supermarket, McDonalds, pastry shops and restaurants. It's easy, safe and free to park on the street. Fast Vodafone internet, ideal for home office.

Guest favourite
An open studio space features a spacious bed flanked by wooden side tables with lamps. A large window offers views of a small garden area with outdoor seating, in natural light that emphasizes the minimalist design.
Home in Palmela
4.91 out of 5 average rating, 244 reviews

Zé House

The house stands out for its modern architecture, integrated in the historic center of Palmela. Zé House was the name given by the architects. A simple house whose architecture sought to assert itself in a secular context due to its contemporary character, establishing not only a geometric relationship with the surroundings but also a chromatic relationship. The result was a surprising and welcoming space.

Guest favourite
Home in São Lourenço
4.95 out of 5 average rating, 20 reviews

Serra da ursa

Exclusive refuge between 6 hectares of vineyards, ideal for relaxing and reconnecting with nature. Unique villa with year-round heated pool, panoramic view and breathtaking sunset. Just minutes from the stunning beaches of Arrábida and in the heart of Setúbal's best wines route. A magical place where every detail invites tranquility. Live unforgettable moments in a setting that looks like a movie .

Popular amenities for São Simão holiday rentals

When is the best time to visit São Simão?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$164 NZD$192 NZD$187 NZD$245 NZD$381 NZD$344 NZD$395 NZD$439 NZD$299 NZD$273 NZD$210 NZD$225 NZD
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Quick stats about holiday rentals in São Simão

  • Total holiday rentals

    Explore 150 holiday rentals in São Simão

  • Nightly prices starting at

    São Simão holiday rentals start at $35 NZD per night before taxes and fees

  • Verified guest reviews

    Over 3,000 verified reviews to help you choose

  • Family-friendly holiday rentals

    100 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 40 rentals that welcome pets

  • Holiday rentals with a pool

    90 properties feature pools

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

  • Wi-Fi availability

    150 of São Simão holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across São Simão rentals

  • 4.8 Average rating

    São Simão stays are highly rated by guests—averaging 4.8 out of 5!

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