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Vacation 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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Top 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 Alcabideche
4.86 out of 5 average rating, 302 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 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, 121 reviews

Pool/Jacuzzi/Park | 35' to the airport | 30 km to Lisbon

Welcome to Quinta do Conde, located 30 km from Lisbon, 18 km from Sesimbra Beach and Portinho da Arrábida! Located minutes from the Highway to access Lisbon, Coina Train 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 a Pharmacy. A 25-minute drive away, you have Setúbal, with access to Tróia by ferry boat, and beaches such as Caparica, Lagoa de Albufeira, Sesimbra and the Cabo Espichel Lighthouse!

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 Union of the parishes of Cascais and Estoril
4.98 out of 5 average rating, 187 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
The outdoor area features a well-maintained swimming pool surrounded by lush greenery and tropical plants. Sun loungers are positioned next to the pool, providing a serene spot for relaxation. A gravel pathway leads through the garden, enhancing the tranquil atmosphere.
Villa in Quinta do Anjo
4.98 out of 5 average rating, 101 reviews

Charming place, beach + countryside, full privacy

Lovely and magical place, fully equipped and recently renovated. Big property, 1.100 m², with fantastic green areas and a very special and unique ambience at the swimming pool area. 100% privacy and very quiet. 15 km away from some of the most beautiful beaches of Portugal and breathtaking sceneries where nature reigns. Great gastronomy, top quality local products like fish, wine, cheese + many others. Small football pitch, table football + ping-pong. Distances: Lisbon 30 m. Airport 35 m.

Top guest favorite
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 favorite
Home in Aroeira
5.0 out of 5 average rating, 10 reviews

Casa Redonda by Villas Aura-Retreat 4-Private Pool

Duplex bungalow with a private heated pool and south-facing garden, approximately 30 m², featuring a deck and outdoor space. The bungalow is fully equipped with a refrigerator, freezer, induction hob, and multifunction oven. It also includes air conditioning, an extractor fan, a Nespresso machine, a French press, an electric kettle, and a toaster for a comfortable and convenient stay. The surrounding gardens and the large heated swimming pool are shared.

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 Costa da Caparica
4.96 out of 5 average rating, 657 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 favorite
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 favorite
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 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 São Lourenço
4.98 out of 5 average rating, 146 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.

Top guest favorite
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, 586 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.

Superhost
A covered outdoor seating area features a woven chair adorned with colorful cushions. A small table sits nearby, while a tranquil dipping pool gleams under natural light. Lush greenery and potted plants surround the space, creating a serene atmosphere for relaxation.
Cottage in São Lourenço
4.66 out of 5 average rating, 70 reviews

Cosy Country House

This house is inserted in a private villa and the place is calm and secure. The house is fully equiped with all kitchen facilities for 2 or 3 people. You can enjoy the country side air, take a bike walk, go to beach, or just relax.

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