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Holiday rentals with a pool in São Simão

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in São Simão

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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Guest favourite
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, 290 reviews

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

Watch the “blackbirds” in the morning, the sunset, enjoy the calm and tranquility. Enjoy the unique sea and mountain view from the private lounge, the infinity pool, the “Serra de Sintra” - the magical mountain, its enchanted forests, convents and palaces. Possibility to include a work desk. There is also the possibility of accepting wedding celebrations, if it is for small groups, for an additional fee. For more information, contact the host directly. A mountain Villa built over 100 years ago, set on an imposing rock with a unique setting and a breathtaking view over the sea, the city, Cascais and the mountain where it is located. The house has been recently remodeled and expanded with a modern and design construction enjoying the view and the surroundings. You can see from the top of the Sintra Mountains, to Guincho to Cabo Espichel. A stone's throw from the hiking trails of the Sintra Mountains and its monuments, and next to good restaurants and cafés with a good atmosphere, the small village has a supermarket and pharmacy for your peace of mind. 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 area. I love cycling and I know the Serra like the back of my hand. I can share the secrets of the mountains and advise on the best restaurants in the region. Malveira da Serra, a picturesque village near Cascais and Lisbon (20 min), with hiking trails in the Sintra Mountains and its monuments. Guincho Beach and its wild dunes with their unique beauty are a paradise for Surf/Kite-surf/Windsurf. I advise using your own car.

Guest favourite
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.
Flat in Cascais
4.94 out of 5 average rating, 181 reviews

Amazing Ocean view + 1km to Beach +Free Vegetables

Relax in a Beachfront apartment surrounded by peaceful nature with stunning Ocean/Mountain views. Why you’ll love it: - Ocean/sunset view - Spacious Pool set among lush greenery - Large organic garden with fresh vegetables, herbs, and tea leaves - 12 minute walk to Guincho Beach (1km away) - Private patio with outdoor dining table - Located by a nature reserve with scenic walking trails - Just 2 minutes from top-rated restaurants and authentic, affordable local cuisine - Fast 200Mbps wifi

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 Setúbal
4.99 out of 5 average rating, 135 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 favourite
An aerial view captures the expansive layout of the Troia resort area, showcasing the Hotel Aqualuz Troia Lagoa 4*, adjacent buildings, and the nearby marina. The surrounding landscapes blend lush greenery with sandy shores, highlighting the serene coastal environment and the river leading towards Setúbal.
Serviced apartment in Carvalhal
4.9 out of 5 average rating, 890 reviews

Suite T1 Sea View Aqualuz Troia Mar & Rio 4****

Suite T1 Premium no 12º piso da Torre TroiaRio, parte do Aqualuz Suite Hotel Apartamentos 4*, com 83 m2 vistas deslumbrantes da península de Tróia, mesmos serviços do Hotel, serviço de limpeza, roupas de cama, toalhas, acesso ás piscinas, toalhas para piscinas, etc Nota: de 1.10.2025 até 1.05.2026, o Hotel Aqualuz Troia Mar & Rio 4* está encerrado Durante este período a sua reserva tem um upgrade gratuito para uma Suite T2 Premium Vista Mar nos últimos pisos do The Anchor Sea 4*.

Guest favourite
Villa in Setúbal
4.88 out of 5 average rating, 197 reviews

Romantic Retreat: Private Pool & Jacuzzi

Welcome to our modern and spacious villa in Setúbal! Relax in the private hot jacuzzi all year round (perfect for chilly winter days!) and in the private pool heated by solar panels (ideal in summer). Perfect for families or romantic getaways: • 5 min drive from the beaches and Arrábida Natural Park • 10 min walk from Setúbal city centre and Mercado do Livramento • Just 25 min from Lisbon! Come enjoy the peace and beauty of Setúbal in any season! 😊🌊"

Guest favourite
The view from the windmill offers a panoramic perspective of the coastline, dotted with greenery. The city skyline stretches in the distance, with the river gently flowing nearby. Various trees and shrubs create a natural border, framing the serene landscape.
Windmill in Caparica
4.96 out of 5 average rating, 627 reviews

Cozy 1850s Windmill with City and River Sunset Views

Discover the charm of staying in a 150-year-old windmill, fully renovated yet rich in original details. Ideal for romantic escapes, families or travelers seeking countryside peace just 10 min from Lisbon. Over 600 guests say we offer the best view of Lisbon — read the reviews! Enjoy sunsets over the Tagus, a pool to refresh in spring and summer, a treehouse, and a functional kitchen. Climb the historic stairs to reach the most stunning views.

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.
Apartment in Tróia
4.9 out of 5 average rating, 233 reviews

Troia Resort Beach Apartment

Em Portugal, na Costa Alentejana, a menos de uma hora de Lisboa, há um lugar perfeito para estar em família, onde poderá aproveitar toda a envolvência com a natureza e praticar inúmeras actividades ao ar livre. Faça passeios de barco ou observe os golfinhos, jogue golfe num dos melhores campos da Europa, visite o maior complexo de produção de salgas de peixe conhecido no mundo romano ou viva um pôr-do-sol numa praia deserta.

Top guest favourite
Home in São Lourenço
4.96 out of 5 average rating, 23 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.

Top guest favourite
A shaded patio features a long table set for outdoor dining, surrounded by green foliage and decorative hammocks. Cobblestone flooring leads to a scenic view of the valley, showcasing the natural landscape in the background.
Home in Terrugem
4.95 out of 5 average rating, 182 reviews

Former Wine Press Turned Country House with Pool

With great views of the surrounding valley, this fab, fully kitted-out four bedroom country home benefits from a well kept garden and a private salt pool. The house is close to some of Portugal's best attractions such as Lisbon (35 minutes) and Sintra (30 minutes), perfect for recharging your batteries.

Top guest favourite
The exterior of the cottage showcases a charming design with a terracotta roof and whitewashed walls. A vivid blue door leads into the home. Stone steps approach the entrance, surrounded by greenery and colorful flowers, creating a tranquil outdoor space with several inviting seating options.
Cottage in Sintra
4.99 out of 5 average rating, 572 reviews

Vintage chic romantic cosy cottage

"Bijou, cute, amazing, lovers' retreat, honeymoon hideaway" - these are just some of the words used by recent guests to describe our lovely stone cottage. Set in a private garden with access to a private pool, it's the perfect romantic setting.

Guest favourite
The outdoor area features a private swimming pool, surrounded by wooden decking and shaded by a fabric canopy. Lush greenery and a landscape of hills are visible in the background, creating a serene environment for relaxation. Sun loungers are positioned by the pool for comfort.
Home in Palmela
4.89 out of 5 average rating, 244 reviews

Holiday Villa with Infinity Pool

This unique charming rustic villa was made to provide well-being in all senses and at all seasons: cosy inside atmosphere, relaxing outside spots, either in the balcony or by the pool, a romantic and inspiring view of the mountain…!

Guest favourite
Two outdoor chairs are positioned on a wooden deck, facing a stunning view of the clear blue sea. A small table sits between the chairs, set for a meal with two plates and a glass. Lush greenery and a few trees enhance the serene coastal scenery.
Cottage in Portinho da Arrábida
4.96 out of 5 average rating, 189 reviews

Casa Sul Mar - Paradise over the sea

With an unmatched view over the ocean and surrounded by luxurious Mediterranean vegetation Casa Sul Mar is the best spot in the Lisbon/Setúbal coast to spend your holidays year round or simply get away for a relaxing week end.

Popular amenities for São Simão rentals with a pool

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