As regular readers of the Trunki Files will know, I spend an awful lot of time – too much time – researching places to take my family on holiday. And when it comes to our annual summer break in the Med, I have a pretty exacting list of requirements. Typically, what I look for for is:

• accommodation with ‘character’, or at least some sense of place;
• a swimming pool (obviously) but also some sort of playground/trampoline/sandpit (young kids do tire of the pool)
• walking distance to a shop, restaurant and beach (getting in and out of cars is so tiresome);
• all kiddie paraphenalia, including toys, books and DVDs, provided – I don’t want to be carting potties and Lego about;
• a host on hand to show me the ropes and help out in an emergency;
• opportunities to interact with other parents (and for my kids to have children to play with);
• childcare onsite – if not a creche, then at least a babysitting service;
• and – more than anything – space and a bed for everyone. No kids-on-sofa-beds-and-evenings-outside-on-the-balcony please. This is supposed to be a holiday!

Unsurprisingly, very few places tick all the above boxes. The ones that do – or get very close – make it onto my annual ‘hotlist’. If I had enough time to take off work, and enough money to blow on holidays, I’d blatantly go to them all. Alas, I can only pick one (at best, two). So in the interests of sharing, and hopefully encouraging some ‘testing’ by other Files followers, here’s my 2014 hotlist for the Med.

Mousses, Lefkada

1. Mousses, Lefkada

Trunki Files readers will know how much I love Periyali, a small collection of villas with pools surrounding a creche in Zakynthos. UK specialist operator Simpson Travel has finally bowed to pressure from Periyali-philes to recreate the formula in another location, with the introduction of Mousses in Lefkas to their 2014 programme. If you can get over the complex’s rather odd name, you’ll find a great set-up for a relaxing (if extremely hot) summer break: individual, two-bedroom houses surrounding a lovely pool, with a taverna for easy meals and British-staffed kids club right on-site. Stunning beaches are a short 5 minute drive away, as is Lefkada town with its waterside restaurants for grown-up nights out (the creche has two evening sessions each week). As far as I can see, the downsides of coming here compared to Periyali are the lack of private pools (except in two villas, which work out quite a bit more expensive than Periyali); and the greater distance from the beach – more a drive than a walk with young kids. But if Periyali is booked up, or, like me, you’ve been before and fancy going somewhere new, then Mousses looks like a winner.

Prices from £821 per person per week based on 4 sharing in August, excluding creche fees. www.simpsontravel.com.

The Quintassential

2. The Quintassential, Algarve

Ok, Ok, the Algarve is not technically the Med, I know; but it’s very Med-Like so it counts. Near the market town of Loule and just 20 minutes drive from the airport at Faro, this little collection of 4 holiday apartments surrounded by beautiful gardens with glorious views towards the coast is a real find. The owners have made it as family-friendly as possible: the pool is fenced; there’s a kids play area with slide and swings for toddlers; plus there’s a games area for older children with trampoline. Adults aren’t forgotten either with a hot tub, free Wi-fi, spa treatment and a meal-service for when self-catering seems too much like hard work. There’s no organised childcare but baby-sitting can be arranged. The fact that the pool’s heated in the shoulder seasons (March/April and Oct/Nov) makes this a viable option for Easter and October half-term, plus you don’t have to commit to a week – a 3 or 4 night short-break is a possibility for the time-poor. The only drawback I can find is there’s only one 2 bedroom apartment – all the others are one. So if you have more than one child in tow, you’ll have to be quick.

Prices from £505 per week for a one-bedroom apartment in August. www.quintassential.com

Scott Dunn Explorers at Pine Cliffs

3. Pine Cliffs Residences, Algarve

Another option in the Algarve, this is the choice for those searching some real luxury. Pine Cliffs is an established resort based on a stunning beach, Praia Falesia. Bigger and more ‘international’ than the usual Trunki Files choices (it’s operated by the Starwood Group), it’s on my list because it’s home to one of UK tour operator Scott Dunn’s much-lauded Explorers Clubs. Offering more intimate childcare than hotel-run kids clubs, the British nannies take kids off for activities and outings to ‘Porto Pirata’, the onsite playpark with pirate ship, 6 days a week (although you are free to dip in and out as much as you or your kids want). In addition to the kids club, the set-up at Pine Cliffs particularly appeals to me because the residences – either two or three-bedroom – come with kitchens and living rooms. So you can fix breakfast or pasta for the kids without tedious waits in restaurants. Of course, should you wish to dine out a deux of an evening, there are plenty of options on site and babysitting on offer.

Prices from about £5,700 a week in August for a two-bedroom apartment, excluding flights. Scott Dunn Explorers is charged extra. www.scottdunn.com

Casa Xaymaca

4. Casas El Sequer and Xaymaca, Costa Blanca

The Costa Blanca is home to one of the Trunki Files’ favourite places, the Caserio del Mirador. But the Caserio’s popularity means it’s often booked out for key holiday periods. As an alternative, consider one of these casas, based not far away in the traditional village of Benimeli. Both are tastefully furnished and come with pools, gardens and even their own orchards. Owners Jennifer and Oswaldo have provided all the kids essentials – cots, high chairs, toys and so on – plus there are extras like bikes for hire and babysitting. El Sequel sleeps 4 in two bedrooms; Xaymaca 8 in four (so ideal for traveling with the grandparents). For me, the primary appeal of these is their location. Away from the hustle, bustle and concrete of the Costa itself, but providing easy access to the beach in 20 minutes, staying here will give you a real taste of Spain. Benimeli central square is a short walk away and is ideal for having an evening drink whilst the kids run around; there’s a municipal swimming pool for a change of scene and mixing with the locals; and for an extra-special experience, the wood-fired oven in the village bakery is available for guests to take their meals to be cooked. Now, you’ll never forget that paella.

From E265 per night for Casa Sequer in August. www.mediterraneorural.com

Agro Can Gall, Ibiza

5. Agro Can Gall, Ibiza

Ok, so this is where the cool kids go. Or the cool parents that is. It’s the sort of place I thought was off-limits to Mums and Dads. But no, it seems the owners, themselves parents to young children, have created a haven for families in the heart of the Ibizan countryside. A beautiful 200 year old Finca surrounded by olive and almond trees, the Agro Can Gall has a pool so sexy it should be on the cover of a glossy magazine. For kids, there’s a playground, a huge garden, games room and farm animals. For adults, there’s babysitting, an onsite restaurant with breakfast included. Most appealingly, family suites are on offer. Although you can fit up to 2 extra children in the double rooms, I prefer more space. Each of the two suites offers has a double and a twin bedroom, plus outside terrace for sitting and eating. The downside is no kitchen (although there is a fridge in the room for snacks and drinks).

From E410 per night for a family room in August. www.agrocangall.com

Coming next: the Trunki Files 2014 Hotlist Part 2: the UK