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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, 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 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, 274 reviews

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

Observe the “melros” in the morning, the sunset, enjoy the calm and tranquility. Enjoy the unique sea and mountain view of the private lounge, the infinity pool, the “Serra de Sintra”-a magical mountain, its enchanted woods, convents and palaces. Possibility to include a work desk. There is also the possibility of accepting wedding celebrations, if it is small groups, for additional payment. For more information contact the host directly. A mountain villa built more than 100 years ago , built on an imposing rock with a unique enveloping and breathtaking view over the sea to the city , Cascais and the mountain where it is located . The house has been recently renovated and enlarged with a modern and design building enjoying the view and surroundings . You can see from the top of the Serra de Sintra, to the Guincho to Cabo Espichel. Two steps from the footpaths of the Serra de Sintra and its monuments, and next to good restaurants , from cafes with good surroundings , the small village has a supermarket and pharmacy for its tranquility. Guests have at their disposal a house with 2 bedrooms, living room and kitchen, fully private and access to a large garden with an infinity 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 I know Serra like the back of my hand. I can share the secrets of the mountain and advise the best restaurants in the region. Malveira da Serra, a picturesque village near Cascais and Lisbon (20 min), with walking paths in the Serra de Sintra and its monuments. Guincho Beach and its wild dunes with its unique beauty, are a paradise for Surf/Kite-surf/Windsurf. I advise you to use your own car.

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, 204 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.

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, 214 reviews

Christmas Cottage outdoor tub, fireplace & nature

Tranquil and secluded cottage in the hills of Sintra. Absolute privacy & luxurious amnesties. The newly renovated Casa Bohemia has a spacious and light-filled living room, with a wood-beamed ceiling and fireplace. The adjoining bedroom, has a queen-sized bed and en-suite bathroom with a shower. A private courtyard leads to an antique stone-bath for romantic outdoor bathing. The kitchen is fully equipped with a Smeg fridge, nespresso and popcorn maker. Private garden, terrace, parking, gate, bbq.

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
4.93 out of 5 average rating, 166 reviews

Ocean View + Underfloor heating + Vegetable garden

Enjoy a T1 beachfront apartment with scenic Ocean & Mountain views from the comfort of the sofa. Immersed in Sintra National Park, the Apt is surrounded by pristine nature and Guincho beach is just a 15 min walk away. Also included: - Underfloor Heating - Vegetable/herb garden - Private Patio w/ sea views - Fast wifi (200+ mbps)
 - Free 24/7 Parking area
 - Perfectly located: In peaceful nature yet still restaurants/shops only 2km away


 - 25 min drive to Lisbon, 10 min drive to Cascais centre

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, 258 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
The view from a window reveals a dining area with a wooden table set for an outdoor meal. A floral centerpiece sits at the center, accompanied by plates and cups. The backdrop features rugged cliffs descending into the serene ocean, with soft waves lapping against the shore.
Home in Praia das Maçãs
4.98 out of 5 average rating, 215 reviews

A Place in the Sun - Cliffside house ~ Azenhas do Mar

Discover the charm of one of Portugal’s most picturesque coastal villages: Azenhas do Mar. Located in the municipality of Sintra, just 40 minutes from Lisbon, this house offers a truly unique experience – perched on the cliffs, with the ocean right at your feet. Um Lugar ao Sol is more than just a place to stay – it’s your peaceful retreat between sea and mountains. Perfect for couples, solo travelers, or anyone looking for natural beauty, calm, and a touch of magic.

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, 247 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.

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.

Top guest favorite
The exterior of a white house is shown against a clear blue sky, featuring a covered terrace with seating and a view of the sea. Potted plants decorate the entrance, and areas of sandy ground are visible, indicating a coastal setting. A barbecue grill is also nearby.
Home in Costa da Caparica
4.97 out of 5 average rating, 101 reviews

A Casa da Tia Rosa - Beach House

Tia Rosa's house is located in the Fishing Village of "Praia da Fonte da Telha", a family environment. It is 1 minute from the beach, has a privileged view over the sea. Ideal for relaxing, practicing water sports and taking walks on the extensive beach.

Guest favorite
A view of the serene house framed by lush greenery and large pine trees. The pool glistens in the foreground, complemented by a stone pathway leading to a spacious lawn, featuring a hammock and lounge chairs for relaxation.
Villa in Aldeia da Piedade
4.94 out of 5 average rating, 103 reviews

perfect for families, near lisbon and beaches

With a fantastic garden and view, in a natural park, near a small village, where you can find, markets, pharmacies, cafes, restaurants, cellars, etc The house embraces a spacious sunny green lawn and pool. Just a few minutes to Lisbon,beach or golf.

Popular amenities for São Simão vacation rentals

When is the best time to visit São Simão?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceR1,591 ZARR1,862 ZARR1,811 ZARR2,370 ZARR3,690 ZARR3,334 ZARR3,233 ZARR4,333 ZARR2,877 ZARR2,742 ZARR2,031 ZARR2,183 ZAR
Avg. temp9°C11°C14°C16°C20°C24°C27°C27°C23°C19°C13°C10°C

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 house rentals in São Simão have a kitchen?

    Absolutely! We offer over 60 house 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 free parking, over 30 homes with wifi, over 30 homes with a kitchen, 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 villa rentals in São Simão have free parking?

    Absolutely! We offer over 30 villa 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 house rentals in São Simão?

    Experience the best of São Simão with our house rentals, starting at about $40 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 R339 ZAR 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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