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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
A private horizon pool is visible in the foreground, surrounded by tropical plants and wooden decking. The ocean is seen in the background, with a clear blue sky and distant hills enhancing the serene outdoor experience.
Condo in Praia de Troia
4.89 out of 5 average rating, 251 reviews

Troia Resort Beach Apartment

In Portugal, on the Alentejo Coast, less than an hour from Lisbon, there is a perfect place to be with the family, where you can enjoy all the surroundings with nature and practice numerous outdoor activities. Take boat trips or watch dolphins, play golf on one of the best courses in Europe, visit the largest salted fish production complex known in the Roman world, or experience a sunset on a deserted beach. But there's much more in TROIA A marina, hotels, event and entertainment centers, restaurants, shops and a casino. In TROIA you will find Tourist Apartments, beach houses, lots to build villas or a villa ready to live in.

Superhost
Home in São Lourenço
4.81 out of 5 average rating, 21 reviews

Villa Vintage: Vineyards & Historic Center Azeitão

Discover this charming villa, a haven of soul and character in the heart of Azeitão. Surrounded by winemaking tradition and the serenity of the Arrábida Mountains, it invites you to slow down and savor each moment. Just 5 min. from the iconic Bacalhôa and José Maria Fonseca wineries and 18 min. from the stunning beaches of Galapinhos and Portinho, it’s ideal for sharing meals, peaceful swims, and genuine moments. Spacious, full of light, and perfect for those who value comfort with personality.

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, 100 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 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 São Lourenço
5.0 out of 5 average rating, 45 reviews

Portinho da Arrábida Cabin

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
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, 273 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, 20 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 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 São Lourenço
4.99 out of 5 average rating, 82 reviews

Cafofos da Zeta, Cozy Pool House

Reconnect with nature at this unforgettable escape. Close to the mountains, near the sea. You'll love this unique space with a beautiful private and exclusive swimming pool (heated from May to October). In the shed you can have your meals or simply relax in a Brazilian hammock reading a good book to the sound of birds. We have a gas BBQ for your grilling with the necessary utensils. There is a very cozy corner with a fire pit for unique and special moments of leisure.

Guest favourite
A private swimming pool reflects the clear blue sky, surrounded by a well-maintained garden. The spacious house, featuring a bright exterior, is visible in the background, with multiple windows allowing natural light to permeate the indoor spaces.
Home in São Lourenço
4.96 out of 5 average rating, 25 reviews

Casas de Azeitão - Private Pool, By Home Match

Enjoy a dream getaway in Azeitão! This exclusive accommodation offers the perfect balance between comfort and local charm. Cool off in the private pool, enjoy the convenience of the dishwasher and washing machine, and park with total convenience. Just 5 minutes from downtown Azeitão, 30 km from Lisbon and close to Portugal's most stunning beaches. A haven between the sea, the mountains, and the flavors of the region — ideal for unforgettable moments!

Guest favourite
Home in São Lourenço
4.96 out of 5 average rating, 28 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, 239 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, 142 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.

Popular amenities for São Simão holiday rentals