
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

Aldeia e Mar - Casa de Campo
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.

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!

Luxury Villa with a pool in the city
C’était parfait! Le seul problème est qu’on veut déjà y retourner! Merci ☺️

Very Quiet Studio.
Maria and Filipa were so lovely! Both incredibly friendly and kind. The villa is clean, peaceful and relaxing - and Salsa the dog was a lovely bonus! Would highly recommend to anyone looking for a peaceful getaway.

Casa junto à Praia do Meco. Apenas 29 km de Lisboa
Carmen ist eine wundervolle Gastgeberin und extrem zuvorkommend! Sie kümmert sich unglaublich gut um ihre Gäste und besonders für Familien mit kleinen Kindern bereit sie alles perfekt vor! Das Haus ist ein Paradies für Familien, die Wohnung ist ebenerdig und der Garten und die Terrasse ist wunderschön! Schade, das wir den Aufenthalt vorzeitig abbrechen mussten, aber auch da war Carmen sehr entgegenkommend und hat uns unterstützt. Ich kann diese Unterkunft nur empfehlen!!!

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.

Cabo Oeste
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

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 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.

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
Très belle maison , agréable à vivre , bien équipée sauf qu’il manquait des torchons de cuisine et des serviettes pour les transats de la piscine . C’est calme et reposant . La décoration est magnifique ! Nous reviendrons !
Villa rentals with a pool

House of Happiness, a relaxing paradise!
Luis is a wonderful and very contactable host. A few days before our arrival, he asked if we needed to know anything or if we needed anything. He greeted us personally, showed us around the house and explained everything important. He gave us suggestions for restaurants and stores. He himself suggested that we could check out a few hours later than the regulations. Luis' house is very cozy, we felt as at home. The house has everything you need, enough dishes, cleaning products, coffee, tea, oil, spices, fresh herbs in the garden. There is silence all around. We received a bottle of delicious wine and cookies to welcome us. The rooms are spacious, nicely decorated, there is plenty of space to store things. And this wonderful garden, with beautiful vegetation, clean, nicely decorated, with a pool with warm water. With great pleasure I will return there.

Casinha da Lagoa Sesimbra
la maison est très agréable, paisible et confortable. bien équipée.

Superbe villa contemporaine avec piscine
Vierailumme Brunon luona sujui erinomaisesti ja paikka oli ihana. Mukava naapurusto.

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
Dejligt ophold i en stor lækker villa med mange gode ude områder. God ide at leje en bil, hvis man gerne vil andet end at være i villaen. Rigtig sød og informerende vært.

Janota Week Pool
Sérgio para além de bastante compreensivo no check um e check out , foi sempre extremamente disponível . Indicou nos restaurantes , cafés próximos e atividades para se fazer! A casa estava top, super limpa e bem equipada com bastante privacidade e perto de tudo! Gostamos muito e iremos voltar certamente.

Casa Nina - Villa avec piscine chauffée
Très bonne expérience, la maison est très bien placée, environnement calme. Hotel facilement joignable. Je recommande.

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