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Vacation rentals in São Simão

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Top-rated vacation rentals in São Simão

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Guest favorite
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, 115 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 favorite
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, 278 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.

Top guest favorite
A spacious living area features large windows offering expansive views of the sea and city. Soft natural light floods the room, highlighting a comfortable sofa and a contemporary television. A cozy armchair adds to the inviting atmosphere, while a wood-paneled accent wall provides texture.
Apartment in Paço de Arcos
5 out of 5 average rating, 208 reviews

THE miniPENTHOUSE terrace & SPA

Apartamento reconstruído por arquitecto, excelente privacidade, exposição solar, com wifi, e praia a 150m. 1 suite com SPA e banho turco com aromaterapia. 1 suíte com terraço com vista mar, tela de projeção de cinema. Sala com vista de mar, rio, e terraço, onde poderá disfrutar de uma zona de estar e de um barbecue com grelha em ferro forjado. Perto de restaurantes, cafés e supermercado, e estação de comboio. Ar condicionado e piso aquecido em todas as áreas, TV 4K e box independente por suíte.

Top guest favorite
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 Cascais
4.98 out of 5 average rating, 158 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.

Guest favorite
A spacious pool is surrounded by lush greenery, with a wooden deck enhancing its natural setting. The stunning sunset casts vibrant colors over the sky, creating a serene backdrop against the tranquil water.
Apartment in Cascais
4.94 out of 5 average rating, 172 reviews

Floor heating - Ocean View - 15 min walk to Beach

Escape to this bright and cozy T1 apartment with amazing ocean and mountain views, perfectly nestled in nature. Located by Sintra-Cascais Natural Park, the apartment offers peace, privacy, and easy access to Guincho Beach (15-minute walk). Also included: - Underfloor Heating in all rooms - Fast wifi (200+ mbps)
 - Perfectly located: In nature yet restaurants/supermarkets only 2km away - Large Pool and garden area - Free parking onsite
 - 25 min drive to Lisbon, 10 min drive to Cascais centre

Top guest favorite
A spacious living area features a large, soft sofa and colorful chairs, creating a comfortable seating arrangement. Floor-to-ceiling glass windows provide natural light and views of the garden. Decorative art pieces and plants add a touch of warmth to the modern design.
Loft in Alcabideche
4.97 out of 5 average rating, 129 reviews

Sunny Garden Studio with Ocean View

Fully equipped, sunny (south-west location) and quiet Garden Loft of about 40 sqm with unobstructed ocean view. Located at the foothills of the Sintra mountain range right at the border of the Sintra National Parque. Driving distance of about 5 minutes to Gunicho beach which is one of the most popular and spectacular beaches in the region. Walking distance to the centre of Malveria da Serra with Supermarket etc. and some restaurants. 10 minutes drive to the charming harbour town of Cascais.

Top guest favorite
The living area features large glass doors that open to a private terrace, allowing natural light to fill the space. A round dining table sits beside a wooden chair, while a lounging chair is positioned on the terrace, surrounded by planters with greenery.
Apartment in Lisbon
4.95 out of 5 average rating, 830 reviews

Lisbon rooftop with terrace and stunning views

A stylish 1-bedroom rooftop apartment with a private terrace and stunning views of the Sao Jorge Castle and Tagus river. Located in the heart of Lisbon, in Marques de Pombal close to the emblematic Eduardo VII park and Avenida da Liberdade. ⚠️PLEASE NOTE there is construction work next door and may be noisy during the day** The rooftop apartment is accessible via an outdoor spiral staircase. Due to the stairs, please note that this apartment is not suitable for people with reduced mobility.

Guest favorite
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 favorite
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, 259 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 favorite
A charming cottage exterior is surrounded by lush greenery, with a terracotta facade and arched doorways. A patio area is visible, featuring a small table and a parasol, providing a shaded spot to enjoy the serene environment.
Cottage in Sintra
4.98 out of 5 average rating, 218 reviews

Cozy Private Cottage with Fireplace & Outdoor Tub

Tranquil and secluded cottage in the hills of Sintra, set within a private historic estate once home to Sir Arthur Conan Doyle. Casa Bohemia offers absolute privacy, a light-filled living room with wood-beamed ceiling and fireplace, a queen bedroom with en-suite bathroom, and a private courtyard with an antique stone bath for romantic outdoor bathing. Garden, terrace, parking, and nature all around.

Guest favorite
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
4.9 out of 5 average rating, 248 reviews

Zé House

A casa destaca-se pela sua arquitetura moderna, integrada no centro histórico de Palmela. Zé House foi o nome atribuído pelos arquitetos. Uma casa simples cuja arquitetura procurou afirmar-se num contexto secular pelo seu carácter contemporâneo, estabelecendo não apenas uma relação geométrica com a envolvente mas também uma relação cromática. O resultado foi um espaço surpreendente e acolhedor.

Top guest favorite
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 Praia das Maçãs
4.96 out of 5 average rating, 146 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.

Popular amenities for São Simão vacation rentals

When is the best time to visit São Simão?

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Avg. priceﺩ.ﺇ345ﺩ.ﺇ404ﺩ.ﺇ393ﺩ.ﺇ514ﺩ.ﺇ801ﺩ.ﺇ723ﺩ.ﺇ701ﺩ.ﺇ940ﺩ.ﺇ624ﺩ.ﺇ595ﺩ.ﺇ441ﺩ.ﺇ474
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Frequently Asked Questions

  • Do house rentals in São Simão have wifi?

    Absolutely! We offer over 70 house rentals with wifi in São Simão. Enjoy a tailored experience with all the comforts you desire.

  • Do villa rentals in São Simão have air conditioning?

    Absolutely! We offer over 10 villa rentals with air conditioning in São Simão. Enjoy a tailored experience with all the comforts you desire.

  • Are there pet-friendly vacation rentals in São Simão?

    Four-legged friends are welcome in São Simão. Choose from more than 40 vacation rentals for guests traveling with pets.

  • Do apartment rentals in São Simão have a kitchen?

    Absolutely! We offer over 10 apartment rentals with a kitchen in São Simão. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for Villa Rentals in São Simão?

    Enhance your stay in our Villa Rentals with the most popular amenities: over 10 homes with air conditioning, over 30 homes with a kitchen, over 30 homes with wifi, over 30 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Are there family-friendly vacation rentals in São Simão?

    São Simão has more than 100 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do house rentals in São Simão have free parking?

    Absolutely! We offer over 50 house rentals with free parking in São Simão. Enjoy a tailored experience with all the comforts you desire.

  • Are there São Simão vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 90 vacation homes with pools in São Simão, available on Airbnb. Make a splash and soak up the sun in style!

  • How much does it cost to stay in villa rentals in São Simão?

    Experience the best of São Simão with our villa rentals, starting at about $20 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there vacation rentals with a dedicated workspace in São Simão?

    Yes! Work meets play with ease at over 60 vacation rentals in São Simão featuring dedicated workspaces. Stay connected and productive in your home away from home.

Quick stats about vacation rentals in São Simão

  • Total vacation rentals

    Explore 150 vacation rentals in São Simão

  • Nightly prices starting at

    São Simão vacation rentals start at ﺩ.ﺇ73 per night before taxes and fees

  • Verified guest reviews

    Over 3,000 verified reviews to help you choose

  • Family-friendly vacation rentals

    100 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 40 rentals that welcome pets

  • Vacation 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 vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, 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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