A sun-soaked holiday in the Netherlands? Trust us, once you’ve
enjoyed a barefoot escape along the sandy shores that run from the
Belgian border to the Wadden Sea Islands, you’ll have your friends
convinced to switch the Algarve for Ameland every year. This
clapboard property in Buren is just 500m from the
expansive beaches edging the West Frisian isle. A group of eight
will have the run of four sharp, contemporary bedrooms, a breezy,
open-plan living space and an outdoor terrace. Worried about grey
days? The basement cinema room will keep you busy if the weather
refuses to play ball. The cosy gas fireplace helps with keeping
warm post-swims in the – admittedly – chilly sea, but we’d play it
safe and stick to beach strolls exploring the picturesque island,
taking in the handsome lighthouse, taste-testing the loca Nobeltje
liqueur and scampering across the sand dunes for fresh seafood at
Stranders.

What it costs: From £63pp per night

Balancing Arcadian charm with design-focused sophistication,
this idyllic hilltop
stay has been meticulously converted into a stylish 12-person
spa escape in Italy’s storied Le Marche region. Connected by stone
pathways crisscrossing a verdant pasture dotted with oak trees, the
three shuttered buildings – including a separate spa house – have
been carefully revamped with soft, neutral tones throughout. Flit
through the light-flooded bedrooms to lounge on comfy sofas or head
outdoors into the fragrant gardens. Days are best spent dipping
into the pool; nights, in the unique wellness space for group
sauna, hammam and jacuzzi sessions. If you’re a restless group,
requiring further entertainment, the owners will be happy to
organise cooking classes, winery tours and olive oil tastings in
the surrounding countryside.

What it costs: From £84pp per night

An ochre-painted, 18th-century farmhouse transformed into a
rural retreat for eight in the almond and carob tree-dotted
countryside of Mallorca? It’s a yes from us (and our friends).
Lovingly redeveloped by award-winning local architect Antonio
Obrador, the interiors of this Búger property showcase the best of Mallorcan
craftsmanship: expect terracotta floors, reed ceilings, Mallorcan
ceramics and a natural colour palette. Outside, the wraparound 15
acres of terraces, gardens and orchards are fragrant with
Mediterranean planting, and house a 16m aquamarine pool for serious
water games, all backdropped by the undulating silhouettes of the
Serra de Tramuntana mountains.

What it costs: From £140pp per night

Tucked between the rolling hills of Alentejo’s agricultural
landscape, near the small village of Sabugueiro, this rustic stay is an ode to the slow-paced lifestyle of
Portugal’s bucolic interior. Standing between ancient
olives and thickly leafed cork oaks, the collection of four stone
bungalows sleeps 10 in elegant, whitewashed bedrooms, all with
polished concrete floors, minimalist furnishing and accents of
natural wood. There’s also a glorious swimming pool, a large living
room, impressive dining space and a fully equipped kitchen. This is
a stay for the gourmands in your circle: farmhouse breakfasts are
included in the price, and you can organise for a local chef to
prepare a feast of Portuguese favourites for an evening banquet on
the terrace.

What it costs: From £42pp per night

Sometimes, the best way to snag an affordable escape is to head
out early in the season. Case in point? This atmospheric eight-sleeper finca perched in the foothills of
the Serra de Tramuntana mountains. Plan to arrive before the summer
season kicks off and you and your gang will have free run of the
organic smallholding for much less than the high-season price. Four
bedrooms reflect the pastoral colours of the Mallorcan farmland
outside – all soft, earthy tones with characterful farmhouse
features – while the elegant living spaces showcase the original
stone-flagged floors and beamed ceilings. Outside, guests are
encouraged to take their pick from the fruit trees, before diving
into the inviting saltwater pool.

What it costs: From £140pp per night

Casa Nova is a property to fall in love with. Framed by rolling
hills, olive groves and the neat ridges of local vineyards, this
Tuscan bolthole combines traditional
architecture with impeccable country-chic interiors. You and your
besties will have the run of seven beautifully furnished bedrooms
and cosy, calming living spaces that showcase regional antiques
alongside chateau-inspired soft furnishings, high ceilings and
idyllic rural vistas glimpsed through the windows. The villa is
surrounded by Chianti’s hazy hills, and sits less than an hour from
Florence, making it the perfect crash pad for a
low-key week away spent exploring the region’s famous wineries and
soaking up the city’s Renaissance culture. Truly la dolce vita.

What it costs: From £100pp per night

Forget what you think you know about Málaga – this walled
hilltop property offers total seclusion in the
Spanish hills outside of town. The traditional Andalusian
architecture conceals quirky interiors and uninterrupted views of
the tree-blanketed mountains around the property. Four bedrooms
(sleeping eight) have been sympathetically refurbished, with
hand-stitched tapestries above the beds and hand-crafted furniture
from local artisans dotted throughout. You’ll spend days lounging
on terraces and in shady corners hidden throughout the gardens and
quirky interiors, exploring the property’s private vineyard and
dipping into the pool, from where you can admire far-reaching views
of the glittering Mediterranean, 24km away.

What it costs: £107pp per night