
Villa vacation rentals in São Simão
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Top-rated villa rentals in São Simão
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Popular amenities for São Simão villa rentals
Private villa rentals

Village and Sea - Country House
Luis & Beatriz are amazing hosts. The home was beautiful and so quiet and peaceful. The grounds were AMAZING and peaceful. We truly enjoyed our time there and will look forward to returning in the future. We highly recommend this property for those visiting the Terrugem/Sintra area. The Oak Cafe was wonderful for brunch and you must have dinner at least 1 night at Azenhas do Mar, for the food and views as well as Mercado Saloio located in Sintra for the nightly music and delicious food and good service. The spa in Cascais is amazing as well. All recommendations of Luis & Beatriz Other places we found were the Marina and shops in Cascais as well as a wonderful little eatery for brunch/ lunch called Mugs Brunch and Cafe in Pedregal. Amazing views and delicious food. Thanks Luis & Beatriz for making our first trip to Portugal amazing. Looking forward to returning.

Villa with pine forest and beach within 5 minutes, in Aroeira
We felt right at home in this lovely rental. It was so nice, bright, very clean and had everything you could possibly need. Kids (4&6) loved the yard and played everyday for hours while we relaxed in the outdoor kitchen. The beach was a short drive with lots of easy parking in May. Great place to stay for day trips to Lisbon and Sintra. Antonio was a great host and easy to reach. They left us lovely fruits and pumpkin jam and delicious cake.

4 Suites Villa, Pool Garden Sauna Tennis Cowork
The house is really lovely and with a lot of character. It is great for a bigger group to share and the pool area in particular is fantastic. Rooms are all reasonably comfortable and with their own bathrooms. There are minor things that could easily be fixed to make the space feel more luxurious as the price is quite high - couple of broken/wobbly furniture items, some more kitchen utensils / glasses as usually it would be a big group staying, some general comfort supplies, quality of toiletries etc. But these are small things - overall its a very nice space with lots of privacy and a nice location.

Villa with pool
We really enjoyed our stay with Philippe. We can highly recommend this place. Philippe was very helpful, always reponsive and the house was great!

Ericeira - São Julião - Surfing Haven
The perfect stay just outside of Ericeira with the most incredible view of the ocean. You can walk down to São Juliao beach or enjoy the view from different view points on the cliff. The house has the perfect layout for a small group as well. We didn’t want to leave and I can’t wait to come back!

Charming Villa Jarros Private pool & Golf
We had a wonderful time at Jorge’s beautiful villa and would love to stay there again sometime in the future. Jorge was a perfect host and responded to any queries very promptly. We would definitely recommend a stay here to anybody.

Precious House in Comporta
Sofia was a very responsive host and provided support throughout. The house is beautiful, very well located (you need a car to move around in this region) between Carvalhal and Comporta villages giving you access to beaches and village amenities very easily. Very good restaurants and shops a short car drive. We, family of 4, 2 adults and two kids really enjoyed the place. It's got everything you need. There's a Playstation, lots of dvds (children included) and of course you can log-in to your netflix/etc. The internet was very good and reliable. The pool was a bit cold even with the heating, but I guess it has also to do with the weather during our stay. Yes, the pool is shallow, but all the family can have fun. For the kids, it's safer and they loved it, stayed inside the pool and playing around it most of the time. Very good stay, we plan to return. Thank you Sofia.

ROCA ART HOUSE
This place was a great home base for us to explore the coast. It was a beautiful and comfortable space to come home to and offered good access to stunning coastal walks. Jose was very accommodating and offered us early check-in to suit our travel schedule which was very helpful.
Luxury villa rentals

Comporta pool heated private CasaChicoCrispim
Absolutely perfect location, walkable everywhere yet private and quiet. Lovely interiors and exterior, the heated pool was very nice since the weather was cool. Extremely organized, functional and user friendly home

Luxury Villa with a pool in the city
It was perfect! The only problem is that we already want to go back! Thank you ☺️

Spacious Poolside Beach House, By TimeCooler
We loved spending the days there, it was relaxing as we expected, the pool served us perfectly, the house has incredible natural lighting and the kitchen is fantastic and clean. All that was missing was a barbecue grill, haha. Otherwise impeccable, I would definitely come back.

Villa in Comporta Village with heated pool
We had a fantastic stay- a great house in a great location. Paula, the housekeeper, was super nice and helpful and the house had everything we wanted for our holiday (the outdoor kitchen area was particularly lovely). Easy access to some fantastic local restaurants and bars in town and a nice walk to the beach along the boardwalk. Comporta is great and would love to return again.

Newly Renovated Beach Villa
I booked the villa for my sister’s hen do and we absolutely loved it! The villa was beautiful and perfect for 10 of us. The location was great because we were close to the beach, and it was easy to order a taxi to the city centre! The host was lovely and checked in with if we needed anything whilst we were there. Would definitely recommend, we had the best time!

Stunning Villa: Pool, Golf & Beach near Cascais
The place is beautiful! the best place that we stayed in Portugal! Sandrine is very helpful! Grocery very close.

Campo de Arroz - Whole Property
Simply perfect. The house is stunning, with everything we could have needed. The pool and gardens were beautifully maintained. The host, Ines, looked after us so well throughout. 5* experience.

Comporta - Beautiful House near Carvalhal Beach
We had such a lovely stay in Comporta! We were visiting friends and truly enjoyed this classic Comporta home. The house was stunning, beautifully decorated with stylish, upscale touches like oversized towels, kitchen essentials, and cozy spaces that felt both elevated and comfortable. It’s perfectly on-brand for the dreamy beach town that Comporta is. The heated pool was a major plus and super easy to use! The location was ideal, just a 5-minute walk to great local restaurants and about 15-20 minutes to the beach. So much to see, do, and soak in… we already can’t wait to return to this little slice of paradise. A note for future guests: doors in Portugal lock automatically—don’t forget your keys! We learned the hard way, but the hosts went above and beyond to help us get back in. Unfortunately, we had a last-minute change of plans and had to leave a day early, though we easily could have stayed forever. Highly recommend this beautiful home and incredible hosts!
Villa rentals with a pool

Exclusive Noble Villa: Six Suites, Estate Pool
The home was beautiful, spacious, and clean for our group of 7. There was a pool table and foosball table in the basement, which was fun. The outdoor pool and beach chair setup was very relaxing. The area has beaches and restaurants that are only a short drive or electric scooter ride away. The golf course is walking distance away. All in, we were very pleased with our decision to stay at this home in Estoril and the hosts were very helpful and quick to respond.

Spacious 'Villa Terracotta', beach nearby, pool
Tristan was extremely attentive and ensured we had everything we needed, even requesting the cleaner to drop some additional essentials off to us. Couldn’t ask for a better host. The villa itself was beautiful and highly recommend to anyone visiting! Thanks again, Tristan !

Lagoa Sesimbra House
the house is very nice, peaceful and comfortable. well equipped.

Cabo Oeste
Had the most amazing time with my family at this villa! From the get go Anaelle was super helpful and responsive to any queries, met us at the villa early check in with ease! Was on hand should we have any questions. We all loved the villa and were amazed how beautiful it was! Looks amazing in the images but more so in person! Highly recommend staying here! It has everything you need! Super peaceful and private, short walk to the closest food shop. 40 min walk / 10 min drive to the closest beach (which was gorgeous!) would love to come back again in the future :)

Comporta Beach Villa
Nuno was an extremely helpful and welcoming host, and his home was a great base for us for the week. Some lovely shops and restaurants within walking distance, and an easy drive to the local beaches

4 chambres, piscine Casa Oleias by SesimbraSunSea
Lovely stay in a big nice villa with many good outdoor areas. It's a good idea to rent a car if you want anything other than being in the villa. Very sweet and informative host.

Janota Week Pool
Sérgio, in addition to being very understanding at check-in and check-out, was always extremely available. He recommended nearby restaurants, cafes and activities to do! The house was great, super clean and well-equipped with plenty of privacy and close to everything! We liked it a lot and we'll definitely be back.

Casa Nina – Villa with heated pool
Very good experience, the house is in a very good location, quiet environment. Hotel easily reachable. I recommend it.
Quick stats about villa rentals in São Simão
Total rentals
20 properties
Nightly prices starting at
R355 ZAR before taxes and fees
Total number of reviews
560 reviews
Family-friendly rentals
20 properties are a good fit for families
Rentals with a pool
20 properties have a pool
Rentals with dedicated workspaces
10 properties have a dedicated workspace
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- Lisbon Cathedral
- Arrábida Natural Park
- Príncipe Real
- Parque Florestal de Monsanto
- Carcavelos Beach
- Praia do Guincho
- Altice Arena
- Praia da Adraga
- Praia da Comporta
- Praia de Carcavelos
- Tamariz Beach
- Badoca Safari Park
- Sintra-Cascais Natural Park
- Lisbon Zoo
- Belém Tower
- Galapinhos beach
- Cabo da Roca
- Albarquel Beach
- Praia das Maçãs
- Lisbon Oceanarium
- Penha Longa Golf Resort
- Foz do Lizandro
- Ouro Beach
- LX Factory