
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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Stunning Countryside Chalet
Quinta da Arrabida – Stunning countryside retreat near magnificient beaches with small pool Quinta da Arrábida – Indoor surface area: 200m2 Quinta da Arrabida: Villa for 8 to 10 people 4 Bedrooms, 4 bathrooms Spectacular living areas, open plan design rooms 8,9ha of private grounds, large terraces, and a small pool for children Surface area: 200m2 – 8,9 hectare private estate Quinta da Arrabida is located near the village of Casais da Serra, the nearest village to the spectacular Portinho da Arrabida beach (7km), set deep within the Serra da Arrabida Nature Park, halfway between the towns of Sesimbra and Azeitão, boasting magnificent and unique views throughout. Daylight pours from every angle into this beautiful designer villa, built on a single floor. The large living room and most bedrooms are fitted with extra large all glass wide doors, so every guest enjoys the unique mountain and green views on every occasion. The open plan living room is exquisitely decorated: centered around a lovely encased fireplace, each piece of furniture has been carefully picked to create a very exclusive country-chic environment, with the unique backdrop of the Arrabida Mountain Range always in mind. The living room opens onto a large terrace fitted with an outdoor dining table next to a barbecue unit, two hammocks and a mattress, entertainment provided by satellite TV, hifi stereo system and wireless internet. All four bedrooms and the four bathrooms were designed and decorated with the same basic principle in mind: to make the most from the surrounding nature, and the pictures speak for themselves. The master suite has a lovely walk-in shower and a dressing area; and opens onto the gardens via the same large all glass doors from two different angles. The second bedroom has two single beds and the third four bunk beds. These two bedrooms share a bathroom. The fourth bedroom has two single beds and en-suite bathroom. A small swimming pool can be fitted within the gardens, providing refreshment for the elder and endless hours of fun for the younger ones. The private grounds of the Quinta are the ideal place to enjoy nature, bird watching and long walks in unspoiled surroundings, beneath historic vineyards, all in close proximity to spectacular beaches. SETTING : Large private grounds in Arrabida National Park – 40 km South of Lisbon Location : Quinta da Arrabida is set in a 8,9 hectare private property, located deep in the Serra da Arrabida Nature Park, 7 Km away from magnificent beaches. 5 Km away is Vila Nogueira de Azeitao – a small historic town surrounded by the national park – well known for its vineyards, local culture, and wine cellars open to the public. Arrabida beach is considered one of the most beautiful beaches in Portugal and Europe, and boasts a natural bay with calm waters, ideal for swimming and snorkeling. The Serra da Arrabida Nature Park was established to protect the beautiful landscape and rich variety of wild life, including eagles, wildcats and badgers. The surrounding mountains are the perfect place to go for a walk, and excursions can be organised with the local nature tour companies. Getting there and around : Two hours flight from most European cities and seven from New York, the villa is reached by car from Lisbon Airport in 45 minutes. A car is essential for this holiday as there is no public transport to the villa. ACTIVITIES AND ATRACTIONS : Gastronomy and Wine tasting : The region of Azeitão is famed for its gastronomy, and even the local supermarket, Intermarché, has a mix of gourmet and standard products. The local gastronomic festival is held from June to September. Fresh grilled fish is an inexpensive delight. Five formal wine routes have been devised in the Setubal peninsula by the ‘Rota de Vinhos’ association, combining wine tasting with sightseeing, arts and nature. The villa is ideally situated to take best advantage of these delights of the area. Local delights include cheeses, pastries, and obviously a very thorough wine culture. Beaches : The villa is located near many sandy beaches, all with different characteristics. Portinho da Arrabida (7km away) is among the most beautiful beaches in Europe. Praia das Bicas (a popular surf spot), Praia da Foz and Praia do Meco are all within a short drive, as well as the unique Troia Peninsula across the Sado Estuary. Golf Information : Quinta do Peru and Aroeira Clube de Campo are both a short drive (10km) from the villa. Tróia Golf (a short drive and a ferry ride) is a difficult course but one of the most beautiful in Portugal. Other options are available nearby such as Ribagolfe, Montado or Aldeia dos Capuchos.

Charm & Design in a House with a Pool and Magnificent View of the Sea and Mountains
Observe the “blackbirds” in the morning, the sunset, enjoy the calm and tranquility. Enjoy the unique view of the sea and mountain from the private lounge, the infinity pool, the “Serra de Sintra”-the magical mountain, its enchanted woods, convents and palaces. Possibility to include a work desk. There is also the possibility of accepting wedding celebrations, if you are small groups, for an additional fee. 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 was recently refurbished and enlarged with a modern and design construction enjoying the view and surroundings . You can see it from the top of the Serra de Sintra, to Guincho to Cabo Espichel. A stone's throw from the pedestrian paths of the Serra de Sintra and its monuments and next to good restaurants , cafes with good atmosphere , the small village has a supermarket and pharmacy for your tranquility. 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 Serra like the back of my hand. I can share the secrets of the mountains and advise the best restaurants in the region. Malveira da Serra, picturesque village next to Cascais and Lisbon (20 min), with hiking trails in 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 advise you to use your own car.

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.

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.

Ocean View + Underfloor heating + Vegetable garden
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

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*

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!

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.

Tranquility so close to Lisbon.
Secluded country house on a small farm near Lisbon. The villa has a modern and cozy decor, lots of light, two bedrooms, one of which is en-suite, two bathrooms and a fully equipped kitchen to allow you a peaceful stay. Please note: we are currently required to charge a tourist fee whose value depends on the duration of your stay. At the time of booking, an average amount of €6 per person can be, within the limit, 11€ is charged. The agreement will be made at check-in.

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.

Lapa garden II @ Pool / Balcony / Elevator / AC
Welcome to Lapa Garden! This stylish apartment is located in a noble neighbourhood of Lisbon, surrounded by parks, local cafes and cosy restaurants. Here you can easily experience the city as a “Lisboeta” (Lisboner) in a charming and calm atmosphere, while still having the Time Out Market, the marina docks, along with many other attractions at walking distance!

perfect for families, near lisbon and beaches
With a fantastic garden and view, in a natural park, near a small village, where you can find, markets, pharmacies, cafes, restaurants, cellars, etc The house embraces a spacious sunny green lawn and pool. Just a few minutes to Lisbon,beach or golf.
Popular amenities for São Simão rentals with a pool
House rentals with a pool

Quinta da Arrábida - Pinheiro House

Blue Sky Villa 2 by LovelyStay

Villa Pool & Resort

Harbour View House - Terrace & Swimming Pool

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Villa Bali Lisbon
Condo rentals with a pool

Super Modern - Pool, AC, secure parking - bus 5min

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Super cosy apartment, best location - Cascais

Penthouse Duplex Rooftop Jacuzzi 4 Room 6 bed 8ppl

3 room apt seaside, pool, garden

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Cascais Seaside: Relaxing home w/ large pool
Home rentals with a private pool

Mar de Prata by Interhome.

Estoril Luminous Villa Close to the Sea Heated Pool

Herdade de Montalvo, Villa 60 by Interhome

Family-Friendly Villa in Sintra Surrounded by Nature

Quinta da Luz, garden paradise with pool

Cozy 1850s Windmill with City and River Sunset Views

Relax on the sunny pool deck. Children friendly

House with Magnificent Sea View and Heated Pool
When is the best time to visit São Simão?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $317 CAD | $256 CAD | $264 CAD | $334 CAD | $411 CAD | $403 CAD | $499 CAD | $528 CAD | $379 CAD | $309 CAD | $356 CAD | $277 CAD |
| Avg. temp | 9 °C | 11 °C | 14 °C | 16 °C | 20 °C | 24 °C | 27 °C | 27 °C | 23 °C | 19 °C | 13 °C | 10 °C |
Quick stats about vacation rentals with a pool in São Simão

Total vacation rentals
Explore 90 vacation rentals in São Simão

Nightly prices starting at
São Simão vacation rentals start at $70 CAD per night before taxes and fees

Verified guest reviews
Over 1,740 verified reviews to help you choose

Family-friendly vacation rentals
70 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wifi availability
80 of São Simão vacation rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across São Simão rentals

4.8 Average rating
São Simão stays are highly rated by guests—averaging 4.8 out of 5!
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- Príncipe Real
- Figueirinha Beach
- Praia do Guincho
- Carcavelos Beach
- Belém Tower
- Praia da Adraga
- Altice Arena
- Badoca Safari Park
- Arrábida Natural Park
- Praia das Maçãs
- Galapinhos beach
- Lisbon Cathedral
- Lisbon Zoo
- Praia da Comporta
- Penha Longa Golf Resort
- Lisbon Oceanarium
- Praia Grande do Rodízio
- Tamariz Beach
- Foz do Lizandro
- Ouro Beach
- Praia de Ribeira d'Ilhas
- Eduardo VII Park
- Galápos Beach
- Arco da Rua Augusta




