Holiday 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 favourite

Home in Cascais

4.86 out of 5 average rating, 269 reviews

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

Watch the “blacks” in the morning, the sunset, enjoy the calm and tranquility. Enjoy the unique view of sea and mountain from the private lounge, the infinity pool, the “Serra de Sintra”- the magical mountain, its enchanted woods, convents and palaces. Ability to include a desk. There is also the possibility of accepting wedding celebrations, if small groups, for an additional payment. For more information contact the host directly. A mountain villa built more than 100 years ago , implanted on an imposing rock with a unique surroundings and a breathtaking view over the sea the city , Cascais and the mountain where it is inserted . The house has been recently renovated and enlarged with a modern and design construction enjoying the view and the surroundings . You can see it from the top of the Sintra Mountains, to the Guincho to Cabo Espichel. A stone's throw from the hiking trails of the Sintra Mountains and its monuments and close to good restaurants , 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, totally private and access to a large garden with an infinite 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 know the mountains like the back of my hand. I can share the secrets of the mountains and advise on the best restaurants in the area. Malveira da Serra, a picturesque village next to Cascais and Lisbon (20 min), with hiking routes in the Serra de Sintra and its monuments. Guincho Beach and its wild dunes with their unique beauty are a paradise for surfing/kite-surfing/windsurfing. I recommend using your own car.

Guest favourite

Flat in Cascais

4.93 out of 5 average rating, 162 reviews

Ocean View + Peaceful Nature +15 min Walk To Beach

Enjoy your own T1 beachfront apartment with scenic sea & mountain views from the comfort of the sofa. The Apt is set right by Sintra National Park, surrounded by pristine nature and Guincho beach is just a 15 min walk away. Also included: - Floor heating - Vegetable/herb garden - Private Patio w/ views - Fast wifi (200+ mbps)  - 750m away from Guincho Beach  - Perfectly located: In peaceful nature yet still restaurants/shops only 2km away    - 25 min drive to Lisbon, 10 min drive Cascais centre

Guest favourite

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 favourite

Home in Cascais

4.98 out of 5 average rating, 142 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.

Superhost

Serviced apartment in Carvalhal

4.9 out of 5 average rating, 844 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 favourite

Villa in Quinta do Conde

4.98 out of 5 average rating, 106 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!

Top guest favourite

Flat 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.

Top guest favourite

Guest house in Aldeia do Meco

4.97 out of 5 average rating, 147 reviews

Luxury garden villa, pool, great views, near beach

This is a beautiful villa with many amenities and sleeps up to 6 guests. The property has lovely views, in a 3.5-hectares nature reserve of pine trees, orchards and gardens. The space is very romantic, quiet and gated. Have access to a large swimming pool that is well-maintained and heated (maximum 30º) with a removable roof. Playground for kids with swings, basketball, ping pong and football table areas. 7-min near Aldeia do Meco beaches and Cabo Espichel.

Guest favourite

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

Apartment in Tróia

4.89 out of 5 average rating, 228 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

Guest house 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 favourite

Home in Sintra

4.98 out of 5 average rating, 110 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.