For our family of five, it’s often prohibitively expensive to book two suites or connecting rooms when vacationing—and feeding that many people in a luxury hotel’s restaurant can require a home equity line of credit. But we’ve found a solution: rentable villas and cottages. The price is usually less per room than a hotel, and many come with pools and a staff that includes cook, housekeeper, gardener and butler. There are myriad villas—from grand to intimate—just waiting for your arrival.
EASTERN SHORE OF MARYLAND From quaint two-bedroom cottages to large country estates on the water, Eastern Shore Vacation’s inventory of properties is enormous. Prospective renters will love the website’s “Mouse on House” feature to view the floor plan and photos of each room, exterior, pool and grounds, and properties can be sorted by location, number of bedrooms and pools, waterfront accessibility and pet policy. Try Sycamore Acres for a waterfront Wedding Crashers-type compound complete with pool and guesthouses or the waterfront, shabby-chic Harbor Hill cottage in the heart of Oxford within walking distance of the famous Scottish Highlands Creamery. Weekly rental rates range from about $1,100 in low season for a restored 1920s Waterman’s cottage to $7,000 in high season for a five-bedroom waterfront home with dock and pool; easternshorevacations.com
Round Hill MONTEGO BAY, JAMAICA Round Hill is arguably the most exclusive family-friendly resort in the Caribbean. And the best way to experience this famous haven is to rent a privately owned villa property with full access to all resort amenities. Round Hill’s Summerland villa, where we stayed (booked through Villas by Linda Smith; see below for more information), has four beautiful bedrooms, a private pool and two acres of green space; it’s a short walk or golf cart ride to the main hotel and resort. The staff is supremely attentive and the chef can whip up healthy and fresh meals to be served alfresco on the front and back verandas. $6,500 to $10,500 a week for four bedrooms and up to eight people—groceries and selected amenities additional; summerlandvilla.net
Hidden Pond KENNEBUNKPORT, MAINE A luxury boutique resort in Kennebunkport that consists of 14 individually designed two-bedroom cottages, Hidden Pond boasts—among other things—a tented spa, a fitness center and picture-perfect New England scenery. Grab a beach-cruiser bike or enjoy a glass of wine in the lodge over a game of chess. Hidden Pond has an outdoor lounge and bar overlooking the pool, and nightly bonfires for roasting s’mores. Guests enjoy a bakery basket delivered each morning to their cottage, afternoon tea and refreshments and unlimited use of many Hidden Pond amenities. Nightly rates range from $425 to $785, depending on season; hiddenpondmaine.com
Othe Villa Resources
LUXURY RETREATS is the world’s leading villa-rental specialist, offering more than 1,500 properties from about $300 to $51,000 per night in destinations worldwide. Visitluxuryretreats.com.
JUST FRANCE has been advising clients on luxury rental accommodations in Paris and the French countryside for 17 years. They will answer even your most detailed questions about the properties and the region and can hire cooks, drivers, housekeepers or other staff ahead of your stay. Visit justfrance.com or call 610-407-9633.
Linda Smith of Cabin John, Maryland, runs VILLAS BY LINDA SMITH. Her luxury Jamaican listings feature a full staff trained by her team, and her “family collection” of villas feature grassy lawns, swimming pools, playrooms and more. Visit jamaicavillas.com or call 301-229-4300.