Vacation rentals with a pool in São Simão

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Top-rated rentals with a pool in São Simão

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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, 270 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.

Guest favorite

The exterior view showcases a charming white house with a sloping roof, surrounded by well-maintained greenery. A shaded patio area with outdoor furniture is visible, alongside a small garden. Sunlight filters gently, creating a welcoming atmosphere for relaxation.

Home in Palmela

4.93 out of 5 average rating, 107 reviews

Village of Light - Summer Edition (5/1 - 9/30)

Aldeia De Luz - a warm and friendly welcome awaits you in our unique home. Each bedroom has its own character and the outside space is a delight. Our pool is available to you along with a beautiful patio and bbq area. Aldeia De Luz is a short walk from typical Portuguese restaurants and a short drive from supermarkets. Public transport is infrequent, a car is preferable. Palmela Castle is close-by, as is the Arrábida Natural Park. Beaches, Setúbal, Lisbon and the airport are within easy reach.

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, 144 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.

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, 162 reviews

Ocean View + Peaceful Nature +15 min Walk To Beach

Enjoy a T1 beachfront apartment with scenic Ocean & Mountain views from the comfort of the sofa. Set beside 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 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.

Apartment in Carvalhal

4.9 out of 5 average rating, 847 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 Hotel The Editory by the Sea 5*

Top guest favorite

An outdoor patio area features a private pool surrounded by a stone terrace. A spacious dining table with six chairs is positioned adjacent to a barbecue area. Comfortable seating is provided by two lounge chairs and a shaded corner sofa.

Villa in Quinta do Conde

4.98 out of 5 average rating, 107 reviews

Villa with pool and Jacuzzi, 30 km from Lisbon

Welcome to Quinta do Conde, located 30km from Lisbon, 18km from Sesimbra Beach and Portinho da Arrábida! Located minutes from the Motorway for access to Lisbon, Comboios Coina Station, Shopping, Green Spaces and easy access to the Quinta do Perú Golf Course. A 2 minute drive away is the Lidl Supermarket, among others and Pharmacy. A 25-minute drive, there is Setubal, with access to Tróia by ferry, and beaches such as Caparica, Lagoa de Albufeira, Sesimbra and the Cabo Espichel Lighthouse!

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

4.98 out of 5 average rating, 133 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

A private garden is featured with a heated swimming pool, surrounded by lush greenery and blooming flowers. Outdoor seating areas with lounge chairs and a small table are positioned near the pool, providing a serene space for relaxation and enjoying the warm Lisbon sun.

Apartment in Graça

4.99 out of 5 average rating, 167 reviews

LUXURIOUS, PRIVATE GARDEN & HEATED SWIMMING POOL

Luxurious and spacious apartment with two bedrooms (each with a private bathroom) and an amazing garden with a private heated and salted water swimming pool, belonging exclusively to the apartment. Located in a historic and charming building, totally refurbished in 2018. With a great location, between the viewpoint of Portas do Sol (Alfama) and Graça viewpoint, 2 minutes walk from the famous tram 28 and 5 minutes walk from the Castle. Great to discover the historic center.

Guest favorite

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, 609 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.

Superhost

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 Tróia

4.9 out of 5 average rating, 229 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.

Superhost

A cozy living area showcases a gray sofa with yellow accents alongside a wooden dining table, surrounded by white chairs. Natural light filters through sheer curtains, highlighting a patterned area rug on the tiled floor. Decorative light fixtures add a modern touch to the space.

Guesthouse in Azeitão

4.9 out of 5 average rating, 157 reviews

VACATION HOUSE WITH THE POOL 2

This is a rural house if you want to be out of town, 15 km from Setúbal and Sesimbra, 20 km to Lisbon. It is inserted in the particular property. We have two separate apartments in this 1 hectare property and my family lives in the other house as well. We do not accept check in after 21:00 hours. If there is no possibility to check in earlier, please ask if it is possible before making a reservation.

Top guest favorite

A lush green landscape unfolds under a clear blue sky, dotted with historic buildings, including a prominent structure atop a hill. Verdant trees create a beautiful backdrop, enhancing the picturesque aura of the surroundings.

Home in Sintra

4.98 out of 5 average rating, 111 reviews

Heart of Sintra - Amazing Views, Pool & Garden

Heart of Sintra is an extraordinary house within an estate located a couple of minutes walking distance from the center of Sintra. The house has every amenity you could possibly need, and the gardens are a wonderful place to wander and feel inspired by Nature. On sunny days you can relax by the pool and enjoy the amazing views over Sintra's landmarks.