
Villa holiday 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.

Comporta pool heated private CasaChicoCrispim
Fantastic place! Location great and very well equipped. And just a short drive to the beach. Fully recommend.

Spacious 'Villa Terracotta', beach nearby, pool
We absolutely loved our stay here, it’s clear the host had put a lot of time and love into their house which is why it appealed to us. We were a group of 8 best friends who wanted a relaxing holiday, exploring the local beaches, restaurants, sights and enjoying the pool which is exactly what we got, and more! We particularly loved how spacious the house was and being able to make food together and catch up in the outside dining area and on the rooftop balcony. There was an extensive collection of pans/pots/serving bowls etc which was really useful for a big group. We were only a short taxi ride to the beach where we enjoyed spending time at the beach clubs, and it was also a relatively short taxi journey into Lisbon and Almada. We would definitely recommend!

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.

House next to Praia do Meco. Just 29 km from Lisbon
Carmen is a wonderful host and extremely accommodating! She takes incredibly good care of her guests and especially for families with small children she prepares everything perfectly! The house is a paradise for families, the apartment is on the ground floor and the garden and terrace are beautiful! Too bad we had to end the stay early, but Carmen was also very accommodating and supported us. I highly recommend this place!!!

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.

Villa Tojeira | Entire Villa, Pool & Padel Court
This is a superb property for a group/ large family holiday. The pictures hardly do it justice and with the pool, padel court, bbq and pizza oven there is so much to entertain everyone during the stay. Elisa provided some great recommendations for the area and met us at the property for check in to ensure we settled in very quickly. The local beach at Magoito was only 8 mins drive away and food at Duna Mar was great so well worth a visit.

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.
Luxury villa rentals

Estoril dream
I highly recommend the Estoril Dream house. It is beautiful, comfortable, well equipped, and in a lovely and quiet area. It worked out perfectly for our group of nine (five adults and four children) for an 8-day stay as a home base to explore the area (walks to Cascais, easy train ride to Lisbon, and drives to Sintra, Evora, Tomar, etc.) The children definitely enjoyed the pool. Cristovao was able to accommodate us with an early check-in and met us when we arrived to show us around the house, answer our questions and provide local recommendations. If we needed any other information before or during our stay, he was quick to respond.

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.

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

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.

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.

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 Possanco, Comporta beach villa
Very nice house , nice to live in, well equipped except that it was missing kitchen towels and towels for the pool chairs. It's quiet and relaxing . The decor is beautiful! We will be back!

Casa Monda - Comporta - Heated Swimming Pool
Highly recommend Bruno’s home. Even better than the photos - it makes a great home for a restful stay. Beautifully designed and provides everything you need. Lovely garden area with heated pool, hammock and sun loungers. Walking/cycling distance to the beach, cafe and restaurants. Hope to make a return visit soon.
Villa rentals with a pool

Lagoa Sesimbra House
The house is very nice, peaceful and comfortable. Well-equipped.

Country House Azeitão - Villa 3 Paths
We are a group of couples with babies and the house is great to make us feel at ease without worrying about the pool because it has a fence. The outdoor porch space, the table and the sofa are great for socializing and for those who have small babies, without having to stay indoors. Thank you!

Cape West
Fantastic villa, thoroughly enjoyed our stay, we were a group of 8 and teh space was welcome, lovely pool, excellent bedrooms & bathrooms, one for each couple, comms with agents was good & very helful, would recommend this property and glad we stayed in it

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
We enjoyed our stay in Sesimbra. The house is big and there is a pretty garden around the house. Patrick is a friendly host, who helped us very well with advice for supermarkets, local, good restaurants, markets and beautiful beaches. There is a nice view from the table on the veranda up to the hills and the swimming pool in front of it. A bit of a lack of shadow, as the umbrella can't be used with the wind all the time, but we managed to catch the shadow at the corners of the grass during the day. A wonderful vacation!

Janota Week Pool
Sérgio, in addition to being very understanding at check-in and check-out, was always extremely available. 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 very much and will certainly return.

Casa Nina - Villa with heated pool
Very good experience, the house is very well located, quiet environment. Hotel easily reachable. I recommend it.

Verdizela 2 Houses and HOT Pool
We had a fantastic stay at this beautiful house, which had everything we needed for our group of 12. The spacious garden and large outdoor seating area were perfect - plenty of room for everyone to relax and enjoy. Inside the main house, the kitchen was fully equipped and more than sufficient for all our cooking needs, so we didn’t need to use the smaller house’s kitchen at all. The highlight for us was the fabulous heated pool—it was really nice to be able to enjoy it at any time of day, and it was warm enough for our 18 month old baby. While the immediate area is quiet, with just a small mini-market and one nearby restaurant, we were aware of this when booking and had rental cars, which made getting around very easy. A car is definitely recommended. Our host, Alexandra, was exceptional—communication was seamless from start to finish, and check-in and check-out were incredibly smooth. We would absolutely recommend this home and hope to be able to visit again someday ☺️
Quick stats about villa rentals in São Simão
Total rentals
20 properties
Nightly prices starting at
$33 NZD 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 de Carcavelos
- Praia da Comporta
- Tamariz Beach
- Sintra-Cascais Natural Park
- Badoca Safari Park
- Lisbon Zoo
- Belém Tower
- Galapinhos beach
- Albarquel Beach
- Cabo da Roca
- Lisbon Oceanarium
- Praia das Maçãs
- Penha Longa Golf Resort
- Foz do Lizandro
- LX Factory
- Ouro Beach