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Vacation rentals in São Simão

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Top-rated vacation rentals in São Simão

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

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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

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, 209 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.

Top guest favorite
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, 84 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 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.

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.

Guest favorite
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
4.88 out of 5 average rating, 26 reviews

Charming Loft in Azeitão

Charming Loft in the typical village of Vila Nogueira de Azeitão Comfortable and fully renovated 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 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.

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

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 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.

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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