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I have booked places to stay in Portugal about eight different ways over the years. A tiny apartment up a staircase in Alfama. A hotel room in Lagos with a balcony I never once sat on. A rented house outside Óbidos that was lovely and a forty minute drive from anything resembling dinner. None of those were bad decisions at the time. Almost all of them would be bad decisions now.
Working out where to stay in Portugal with kids turns out to be a different problem than working out where to stay in Portugal. The views stop mattering. The stairs start mattering enormously. We are taking Lochlan in the spring, his first trip abroad, and I have spent more hours than I want to admit rethinking places I thought I had figured out. Here is where I have landed.
The short version
Cascais for your main base. Baixa if you want to sleep in Lisbon itself. Lagos in the Algarve. An apartment with a kitchen over a hotel room almost every single time.
That is the whole answer. Flat ground, a train station you can walk to, and somewhere to boil water at six in the morning will do more for your trip than any pool or sea view. Everything below is why, town by town, plus the places I would not book.

What I actually look for now
Before Lochlan I booked for atmosphere, and I would happily trade convenience for character. Now I have a list, and it runs in this order.
Is it flat? Not “is it walkable.” Flat. Lisbon is built on seven hills, as I covered in my Lisbon travel guide, which is wonderful at thirty and a logistical puzzle with a stroller.
How many stairs before I reach the bed? Portuguese buildings are old and lifts are not a given. Three flights with a sleeping toddler, a suitcase and a stroller is a job, and you do it twice a day.
Is there a kitchen? I have an autoimmune disease, and eating the way I do at home is part of how I stay upright on a trip. Making Lochlan breakfast without getting everyone dressed first is the other half of it.
How far is dinner, on foot, pushing a stroller, at the end of a day when everyone is done? And is it quiet by eight? That last one knocked out more of my old favorites than anything else.
The view comes after all of that. It used to come first.
Lisbon: Baixa, and why I stopped booking Alfama
I love Alfama. I have stayed there twice and I would stay there again in a heartbeat on a trip without a small child. The lanes are narrow, the buildings lean, and you can get properly lost in four minutes.
It is also a terrible place to put a toddler to bed. Steep in every direction, the calçada portuguesa underfoot polished glassy by two centuries of feet, and the restaurant terraces still going at one in the morning under your window. Add a stroller with small wheels and you carry it more than you push it.
So for this trip I am booking Baixa. Baixa and Chiado are the flat part of Lisbon, laid out on a grid after the 1755 earthquake, which means right angles, gentle gradients and no surprise staircases. You are on the metro, you can walk to the river, and you reach a startling amount of the city without climbing anything. When you do want to go up, the Santa Justa lift and the funiculars do it for you. My list of things to do in Lisbon still mostly works from down here, and the restaurants I go back to are nearly all reachable on the flat or one metro stop away.
Belém is the other option I would take seriously. Further out, much calmer, wide pavements and lawns and the water right there. You trade convenience for peace, and with a toddler that trade looks better than it used to. I would skip Bairro Alto and Príncipe Real for sleeping. Both are good places to spend an evening. Neither is somewhere a child goes to sleep at seven.

Cascais: the base I would book first
If someone gave me one booking to make for a family trip to Portugal, it would be here, and it would not be a close call.
Cascais is thirty minutes from Lisbon on a train that runs along the water the whole way and costs a couple of euros. So you sleep somewhere small and flat and quiet and still have Lisbon as a day trip, which is backwards from how most people plan it and much better. The town itself is almost entirely walkable, as I said in my Cascais travel guide, and the historic center puts you near the beaches and the restaurants without needing a car at all.
The beaches are the real argument. Praia da Rainha, Praia da Ribeira and Praia da Duquesa are small sheltered coves right in town, not vast windy stretches you have to drive to. Small and sheltered is what you want when the person you are with is two and has opinions about waves.
There is also the Mercado da Vila, open since 1952, which is the reason an apartment here makes sense. You buy fruit and bread and fish in the morning and cook it that evening. Eating out in Cascais is good and reasonable, and I still want a few nights where nobody has to sit still in public. My things to do in Cascais list holds up with a small child, minus the Guincho surf. Guincho is about four miles out of town with real Atlantic wind and real current. Lovely for a lesson. Not where I would base a family without a car.

Sintra and Óbidos: go there, do not sleep there
I have stayed near both and I would not do it again with Lochlan.
Sintra is a hill with palaces on it. That is the appeal and that is the problem. The climb to Pena is steep, the climb to the Moorish Castle is steeper, and the town tips uphill the moment you leave the station. Óbidos is a walled village on a rise, with cobbles that are lovely right up until you are pushing forty pounds of child over them.
Both are worth a day. Both are an hour or less from a flatter base. Go out, climb the thing with the child on your back, come home to somewhere level. My Sintra and Óbidos travel guide covers getting there, and the things to do in Sintra and Óbidos list is worth reading before you decide how much you will honestly manage. You will not manage both in one day. I have tried it childless and it was a lot.
If you do want a meal out there, these are the places I go.

Lagos: my pick in the Algarve
The Algarve is where most families end up and I understand why. Lagos is the town I would choose. The old town is small and flat and you get everywhere on foot, which matters more than almost anything. The famous coves, Praia do Camilo and Praia de Dona Ana, have high cliffs, clear water and a staircase down. Meia Praia is the one I would book near with a toddler: long, flat, easy to walk onto, no steps.
Rates drop noticeably in May, June, September and October, which lines up with the months I would want to go anyway. August in the Algarve is hot, full and expensive, and no version of that is relaxing with a two year old.
My Lagos travel guide has the layout, the things to do in Lagos list is mostly toddler-compatible if you skip the grotto boat tours, and these are the restaurants I go back to. Several have outdoor tables, the single most useful restaurant feature a parent can ask for.

Albufeira: when a resort is actually the right answer
I am not sniffy about resorts. There are trips where a pool, a kids’ club and a buffet are exactly right, and if what you need is four days of nobody cooking and nobody planning, Albufeira does that better than Lagos does.
The thing to get right is which part. The Strip is loud and late and built for a different holiday entirely. The Old Town is the calmer option and the one I point families toward, and there are apartments and villas around the Marina too. Larger resorts sit out past the busy middle of town, which is where you want to be if a pool is the main event. My Albufeira travel guide breaks the areas down, this is what there is to do, and the food is better than its reputation once you walk away from the strip.
Would I pick it over Lagos? No. But if you have an older child who wants a water slide, Albufeira is the answer and Lagos is not.
If you would rather have all of this in one place instead of eleven open tabs, it is also in my Portugal for Families guide. It is a 13-page PDF covering Lisbon, Sintra and Óbidos, Cascais, Ericeira, Lagos, Albufeira and Madeira, with the full 10-day itinerary and a “with kids” section in every chapter.
Ericeira: only if someone is surfing
Ericeira is a surf town, properly so, and a good one. It is also not a place I would base a family that is not there to surf. The beaches sit below cliffs, which means steps, and the good swimming is not the gentle paddling a toddler wants. If Danny wanted a week in the water I would happily go, and plan around one of us being at the beach and one of us in town. My Ericeira travel guide and things to do in Ericeira will tell you whether it is your kind of place. It is forty minutes from Sintra, so it works as a stop rather than a base.
Madeira: Funchal, and the hill you cannot see on a map
Madeira is my favorite place in Portugal and the hardest one to recommend for a first trip with a small child.
Most accommodation sits in Funchal or the hotel zone just west of it, which is where I would stay, and from there most people rent a car and drive out to everything else. That is the right way to do Madeira and it is also the catch. The island is vertical. Roads climb and switchback and tunnel, and the distance between two towns on a map tells you almost nothing about how long it takes or how it feels in the back seat.
Funchal is steeper than it looks in photos. The hotel zone is flatter and duller and that is a fair trade with a toddler. There are quieter bases around the island, Machico and Santa Cruz and Câmara de Lobos among them, which my Madeira travel guide covers, and the food is reason enough to come. Most of what there is to do involves a drive and some of it involves a cliff.
I will take Lochlan there. I am not taking him there first.

Apartment or hotel?
Apartment, nearly always, and the kitchen is only half the reason.
The other half is that a hotel room is one room. When the child goes to sleep at seven, you sit in the dark on your phone until you give up and sleep too. A separate bedroom gives you back three hours of your own evening, and across ten nights that is the difference between coming home rested and coming home needing a holiday.
The kitchen does matter though. With an autoimmune disease I do better when I can cook a few plain meals, and with a two year old I do better when breakfast does not require shoes. Rentals in Portugal usually come with a washing machine too, which sounds dull and is the most useful appliance on any trip with a toddler.
What I check before booking, every time: how many floors and whether there is a lift, whether the bedroom is separate or a nook with a curtain, whether there is a cot and what kind, and whether the street is residential or restaurant-lined. That last one is worth five minutes on a map. A quiet lane versus a terrace of tables is the difference between a child who sleeps and one who does not.
🛒 A few things I use for this
- A lightweight travel crib, because what a rental calls a cot is a genuine lottery
- A small portable sound machine, which is the single best answer to a restaurant terrace under the window
- A travel blackout blind for the long evenings, since it is still bright at nine in June
- A back carrier for every hill the stroller cannot do, which is most of Sintra
- A plug adapter or three, because there are never enough outlets near the bed
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The one thing I would skip
A countryside quinta or a villa with a pool, out in the hills, twenty five minutes from town.
These listings photograph best and I would have booked one in a heartbeat five years ago. Olive trees, a long table outside, total quiet. I stayed in one near Óbidos and it was one of the prettiest places I have ever slept.
With a toddler every single thing becomes a drive. Forgot milk, that is a drive. Nap ran long and now it is five o’clock and nobody has eaten, that is a drive, in the dark, on a road with no shoulder. You end up eating in and a bit stranded, and the pool gets maybe forty minutes a day once you account for the sun, the naps, and someone having to be in it the whole time.
Book the boring flat apartment two streets from a bakery. You will use the town every day and the pool less than you think.
Questions I get about where to stay in Portugal with kids
What is the best area in Portugal for a family holiday?
Cascais, for most families. It is flat and walkable, the beaches in town are small and sheltered, and the train puts Lisbon half an hour away without making you sleep in a city. The Algarve is right if the beach is the entire point, and Lagos is where I would go in it.
Is it better to stay in Lisbon or Cascais with kids?
Cascais, and day trip in. Lisbon is a hill city with late nights and hard cobbles, and you spend real energy fighting that with a stroller. If you do want to be in Lisbon, stay in Baixa or Belém, not Alfama. I go into the trade-off in my post on whether Portugal is good for families.
Should we book a hotel or an apartment?
An apartment, if you have the choice. A separate bedroom gets your evenings back, a kitchen means breakfast without a production, and a washing machine means you pack less. Hotels make sense when you want a pool and a kids’ club, which is mostly an Albufeira situation.
Do we need a car in Portugal with kids?
Not for Lisbon, Cascais or Lagos. The trains and your feet cover it, and parking in all three is an ordeal. You want a car for Madeira and the wider Algarve. Rental car seats run six to ten euros a day, so for a week or more, bringing your own is cheaper and you know what you are getting.
How many nights should we stay in each place?
Three minimum, four is better. Two nights somewhere means one real day, and packing a family is not free. Our 10-day Portugal itinerary with kids is three stops across ten nights for exactly this reason, and that still felt like the upper limit when I was sketching it out.
When is the cheapest time to book?
November through March is cheapest outright, though the Algarve is quiet and much of it is closed. May, early June, September and October are the sweet spot: rates come down from the August peak, the water is swimmable, and you are not pushing a stroller through a crowd. More on all of it across the Portugal posts.
I have not booked any of it yet. The tabs are open, Danny has started making noises about flight prices, and I keep changing my mind about whether four nights in Cascais is too many or not nearly enough.
If you are in the same spot, second-guessing every listing, I am right there with you. Tell me where you are thinking of staying. I would like to know.