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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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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
4.9 out of 5 average rating, 48 reviews

Charming Loft in Azeitão

Charming Loft in the typical village of Vila Nogueira de Azeitão Comfortable and fully rehabilitated Close to all shops and services and 100 meters from the bus stops to the beaches of Sesimbra and Figueirinha. Extremely cozy and refined place with unique decor. 5-minute walk to: Serra da Arrábida Natural Park; Adega; Intermarche; Restaurants; Bars. By car: 45 minutes from Lisbon; 20 minutes from Setúbal; and 20 minutes from Sesimbra. SAE - Sonho Azeitão Envolvente (Azeitão Surrounding Dream)

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, 104 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.

Top Guest favourite
A French antique bathtub filled with bubbles is positioned in the foreground, with a leafy plant adding a touch of greenery. In the background, a cozy seating area is visible, featuring a comfortable sofa and a small coffee table. Natural light filters through sheer curtains.
Place to stay in Colares
5.0 out of 5 average rating, 55 reviews

Sanctuary in the Sintra Forest

This intimate yet spacious studio guest house sits in a tiny, old-world mountain village where sun and mist stream through the pines, owls call in the night, and a centuries-old water mine flows quietly beneath. Surrounded by ancient forest paths and just 10 mins by car from golden beaches, wild swimming, romantic ruins, and beloved restaurants. Ideal for couples or small families seeking beauty, serenity, and something magical. A retreat into nature, quiet luxury and beauty.

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
4.97 out of 5 average rating, 278 reviews

Moinho do Marco: the romantic windmill hideaway

Let yourself be carried away by the charm 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 Arrábida Natural Park, let yourself be conquered by the tranquillity of nature from the terrace, which offers the best view over the beautiful Setúbal Bay. Enjoy this unusual, romantic and sustainable accommodation at any time of the year.

Guest favourite
A charming white structure features large arched windows, bringing natural light into the space. Two inviting chairs are positioned on the wooden deck outside, surrounded by lush greenery and rustic stone paths. The sloping roof is accented by traditional tiles, enhancing the home’s character.
Home in Setúbal
4.95 out of 5 average rating, 21 reviews

Arrábida Getaway • Jacuzzi & Mountain Views

Once a charming tea house, this cozy studio is a peaceful retreat on a private family farm in the heart of Arrábida Natural Park — with total privacy, yet just minutes from Setúbal’s historic centre and stunning beaches like Portinho da Arrábida and Galápagos. Outside, hike or bike limestone trails with Atlantic views, kayak and snorkel in crystal-clear waters, sip Moscatel at local wine quintas, or browse the iconic Mercado do Livramento for fresh fish and regional produce.

Top Guest favourite
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
5.0 out of 5 average rating, 243 reviews

THE miniPENTHOUSE terrace & SPA

Apartment rebuilt by architect, excellent privacy, solar exposure, with wifi, and beach at 150m. 1 suite with SPA and Turkish bath with aromatherapy. 1 suite with terrace with sea view, cinema projection screen. Room with sea view, river, and terrace, where you can enjoy a seating area and a barbecue with a wrought iron grill. Close to restaurants, coffee and supermarket, and train station. Air conditioning and heated floor in all areas, 4K TV and independent box by suite.

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
4.95 out of 5 average rating, 22 reviews

Lisbon/Beaches: House with terrace

Azeitão/Arrábida: Your Perfect Getaway! Discover our charming typical little house in Vila Fresca de Azeitão The house has two double bedrooms and a terrace with a view, ideal for outdoor dining. It is fully equipped with a full kitchen (fridge, microwave, dishwasher and coffee machine), washing machine, TV and internet. Can’t beat the location: 27 km from Lisbon 12 km from Setúbal/Sesimbra Just 15 minutes from the paradisiacal beaches of Costa da Arrábida.

Guest favourite
Home in São Lourenço
4.97 out of 5 average rating, 29 reviews

Serra da ursa

Exclusive retreat among 6 hectares of vineyards, ideal for relaxing and reconnecting with nature. Unique villa with a year-round heated pool, panoramic views, and breathtaking sunsets. Just minutes from the stunning beaches of Arrábida and in the heart of the route of the best wines of Setúbal. A magical place, where every detail invites tranquility. Experience unforgettable moments in a movie-like setting.

Guest favourite
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, 244 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 favourite
Bungalow in São Lourenço
5.0 out of 5 average rating, 8 reviews

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.

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
4.98 out of 5 average rating, 147 reviews

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.

Guest favourite
An elegant dining area is highlighted by a glossy black table surrounded by stylish chairs. Natural decor elements include tall, slender plants and textured wall designs. Subtle lighting enhances the warm ambiance, while a large television and decorative items offer a modern touch to the space.
Home in São Lourenço
4.83 out of 5 average rating, 72 reviews

The Sweet Dreams Holiday House

The Sweet Dreams Holiday House is the place where you will feel like home. It as all the amenities to make you feel comfortable, welcome and relaxed. It is located in a familiar and very quiet neighborhood. It is very likely that you will be awake by the sweet singing of the birds.

Popular amenities for São Simão holiday rentals