From beachside bungalows in Bali to converted Tuscan olive presses, we’ve rounded up some of the best family villas and cottages for big brood breaks. Whether you’re an eleventh hour summer planner or an early half-term schemer, have a look and start daydreaming about private pools, cosy cottages, and al fresco dining for your next luxury family holiday.
VILLA SAN PIETRO | TUSCANY, ITALY
Style Wood-beamed and whitewashed
Setting The sprawling Monteverdi estate
Best for… school holidays and breaks with your teens; Villa San Pietro has two bedrooms with king-size beds (one upstairs and one down), giving you all plenty of space to do your own thing. Oenophiles will love the private wine cellar.
Star attractions Borrow bikes and cycling gear, arrange a private cookery class with Monteverdi’s head chef Paolo and explore Tuscany’s best bits, which are within easy reach.
Packing tips Don’t forget your swimsuits: the villa’s lavender-surrounded infinity pool overlooks the verdant Val d’Orcia. Bring your hiking shoes and sketchpads for the trails around Monteverdi (chat with the resident artist for inspiration).
HAMILTON ISLAND YACHT CLUB VILLAS | GREAT BARRIER REEF, AUSTRALIA
Style Bright by the sea
Setting Island for aspiring Attenboroughs
Best for… multi-family holidays; the beds in these four-bedroom villas can be set up to suit your group. Spacious living areas, large kitchens and sea-facing furnished balconies give big broods more than enough room.
Star attractions Adventures await (think kayaking, windsurfing, snorkelling and deep water turtle-spotting), but the white-sand beach, trio of pools, and Spa Wurmurdaylin will beckon to relaxation seekers.
Packing tips Bring Mr Smith’s lucky apron for manning the barbie (ask your personal concierge where to find fresh fish and other grilling goodies), a floppy hat for Mrs Smith’s sunning, and little Smith water-wings for swimming in the seaside lagoon-style pool.
AMIRANDES ROYAL RESIDENCE | CRETE, GREECE
Style Beachfront Aegean classic
Setting Seaside seclusion within a resort
Best for… families of five with kids of all ages, or holidays with GrandSmiths; the Royal Residence is split into two distinct areas, each with a master bedroom, and two cots are provided for little Smiths.
Star attractions There’s an Ayurvedic spa and pool-hopping options, but the lure of the blue and white seaside will likely keep everyone occupied. For a dinner à deux, head to Lago di Candia, the most romantic of the resort’s restaurants.
Packing tips Bring the swimsuits; Amirandes has three pools to choose from, including a stunning infinity pool and a behemoth of an Olympic pool, in addition to your two private villa pools. Swimming lessons can be arranged for aspiring little Mer-people.
VILLA ALBA | TUSCANY, ITALY
Style Stacked stone former farmhouse
Setting Castiglion del Bosco hilltop
Best for… a family of four to five, Villa Alba has one king room and one twin room, which can fit an additional bed. A separate guest house can accommodate two guests (perfect for traveling with GrandSmiths).
Star attractions Chef-led Tuscan cooking classes are held in the Borgo and the estate regularly hosts wine-making and wine-tasting seminars. To sample home-grown produce not derived from grapes, visit a local apiary, olive mill or farm.
Packing tips Bring your swimsuits; Villa Alba’s lavender-filled garden has a private heated pool. Pack outdoorsy gear too; the estate is in a sprawling Unesco-protected park, crisscrossed with hiking and cycling trails (borrow the bikes).
DAR JESELI | ESSAOUIRA, MOROCCO
Style Beachfront Berber-style retreat
Setting Sand-side Rebali Riads
Best for… families with older children; With two bedrooms, a sitting room, open plan kitchen, and private pool, Dar Jeseli can comfortably fit a family of four or five.
Star attractions Lounging in your private pool, rejuvenating in the hotel’s hammam, and taking a break from the sun to indulge in afternoon mint tea and Moroccan pastries. After sunset, take the provided star map and head to the roof terrace for family stargazing.
Packing tips Rest and relaxation are encouraged, so pack your holiday reads with your flowing tunics and camel-riding best. Bring the swimsuits; the hotel has two communal pools and the beach is steps from the front door.
VILLA SANT’ANNA | TUSCANY, ITALY
Style Stacked stone Tuscan classic
Setting Ridge above the Castiglion del Bosco vineyards
Best for… multi-family holidays; Villa Sant’Anna has six bedrooms and space for additional beds. The spacious communal areas and garden with private pool provide more than enough room for large groups.
Star attractions Spend the day in your private pool-with-a-view, then make pizzas in the villa’s 17th-century outdoor wood-fired oven. The estate’s winery hosts making and tasting seminars; after setting up the little Smiths in the villa’s home theatre, grownups can take newfound-favourite local wines to the pool house terrace and continue the evening.
Packing tips Bring swimsuits and summer picnic attire, but pack outdoorsy gear for nearby horseback riding and hiking trails of the surrounding Unesco-protected park.
ANANTARA PHUKET TWO BEDROOM POOL RESIDENCE | PHUKET, THAILAND
Style Refined rainforest retreat
Setting Above Mai Khao Beach
Best for… families of six with kids of all ages. The master bedroom has a king-size bed and kitted-out ensuite and the second twin bedroom is on the opposite side of the villa. The living area’s sliding glass doors open to the villa’s private pool, which has a wading section at one end.
Star attractions Learn Thai cooking techniques and test-drive them in your villa, walk down to the beach for surfing lessons with your teen or lounge by the hotel’s vast infinity edged pool.
Packing tips A good book to read while the kiddos splash about in the wading pool and lots of sun protection; the Thai sun is fierce.
KARMA KANDARA POOL VILLA | BALI, INDONESIA
Style Supersized Balinese treehouse
Setting Overlooking Indian Ocean
Best for… newly minted families of three. With a king-size bed, open plan living area, private pool and outdoor terrace, the One-Bedroom Pool Villa is a roomy retreat for that belated babymoon.
Star attractions Indulging in the view and luxurious treatments at Karma Spa, snorkelling in the clear blue ocean, and celebrating with dinner at one of the perimeter tables of restaurant Di Mare.
Packing tips Prioritise the swimsuits; you will most likely spend days rotating between your private villa pool, the main two-level infinity pool, and the beach. Bring a waterproof camera for kayaking and snorkeling adventures.
SA ROTA D’EN PALERM APARTMENT | MALLORCA, SPAIN
Style Family-run retreat
Setting Heart of the island
Best for… low-key family time for four; the apartment has two bedrooms, two bathrooms, and a terrace overlooking the Mallorcan countryside.
Star attractions Spend time in the pool or exploring the grounds, breakfast like champions on homemade jams and breads and gain a sense of traditional Mallorcan rural life by visiting the village of Sant Joan and Els Calderers, a working manor with stables, farm animals, bakery, and smithy stocked with historic tools.
Packing tips Take sturdy shoes for cycling through the countryside. Remember to bring your swimsuits; the hotel has a pool-with-a-view and several beaches are a short drive away.
PARADISE ISLAND VILLAS | CRETE, GREECE
Style Secluded villas
Setting Cretan paradise found
Best for… families with teens. The Executive Villa’s master suite has king-size bed and a balcony overlooking the sea; the junior bedroom has two twin beds. There’s a fireplace in the living room and the sea-view garden has a dining area and private pool surrounded by sunloungers and parasols.
Star attractions Spend days in and around the pool, and book into the spa for a relaxed tete-a-tete with your teen. Make a family meal together in your villa, or enjoy the Mediterranean cuisine at Ambrosia.
Packing tips Bring books and swimsuits for lounging in and around the pool. Pack your tennis shoes and whites to take advantage of the courts.
VILLA MARGARITA | MARBELLA, SPAIN
Style Whitewashed Andalusian serenity
Setting Seaside at Puente Romano Beach Resort
Best for… extended family gatherings or multi-family holidays, the three bedroom Villa Margarita has a large living area and kitchen for family chatting and snacking. Outside, there’s a seating area around your heated private pool.
Star attractions Walk to the beach, enjoy barbecues in your private garden and have dinner at beach-side restaurant Del Mar.
Packing tips Bring the family swim gear; the resort is steps from the beach and has three communal pools. Bring something outdoorsy to hit up the nearby equestrian centre and pack your tennis whites; the courts are right next to the villa.
Have we awoken your interest in luxurious self-catering stays? Check out our full collection of Family Villas and Cottages for more holiday inspiration.
Copy by Lauren Coffey.