Affluent families and groups are opting for vacations in warm-weather destinations such as Costa Rica and the Caribbean for vacations that prioritize privacy and personalized experiences, said Rental Escapes, a luxury villa company.
“This year’s top destinations offer the perfect combination of warm weather, memorable experiences, and spacious villas where everyone can stay under one roof,” said Brian Schwimmer, chief executive officer and co-founder of Rental Escapes. “Villa travel allows families to focus on what matters most: spending quality time together.”
Here are some recommendations from Rental Escapes’ portfolio of luxury villas in Costa Rica and the Caribbean to consider planning your clients’ holiday and winter vacations.
Costa Rica
Casa Hamaca (Source: Rental Escapes: Inside 2026’s Top Luxury Holiday Destinations)
Villa Motmot in Tamarindo and Casa Hamacas in Hacienda Pinilla are designed with multigenerational groups in mind, featuring accommodations for 12 guests and 14 guests, respectively.
Villa Motmot provides guests with convenient access to sailing, horseback riding, and hiking experiences, and is equipped with a pool, outdoor living spaces, and nearby beach, golf, nd tennis amenities.
Casa Hamacas is equipped with a pool, plentiful outdoor living spaces, a nearby beach, and golf and golf and tennis amenities.
Dominican Republic
Ocean Bliss (Photo Credit: Rental Escapes)
In the luxury enclave of Casa de Campo, guests can take advantage of golf, sailing, horseback riding and beach clubs while accommodated at such villas as the oceanfront Ocean Bliss, which accommodates 14 guests in six en-suite bedrooms. This modern, oceanfront villa accommodates up to 14 guests across six en-suite bedrooms.
“The property features a spacious pool, a jacuzzi, an outdoor dining gazebo, and an indoor bar. Positioned between Minitas Beach and the marina, the villa offers guests easy access to premium local activities, including championship golf, tennis, sailing, horseback riding and scuba diving,” Rental Escapes said.
Jamaica
Hidden Bay
For groups of 12 or less, Hidden Bay is a “unique property that features both a main residence and private cottage connected by beautifully landscaped grounds. Guests can spend their days kayaking, snorkeling and relaxing by the pool before gathering each evening to celebrate the holidays overlooking the sea,” Rental Escapes said.
Turks & Caicos
Cabuya (Source: Rental Escapes)
Set in one of the Turks & Caicos’ exclusive areas, Cabuya accommodates 12 guests with generous indoor and outdoor space (including the living room) and an infinity-edge pool. “The villa provides direct access to kayaking and paddleboarding while offering plenty of room for families to gather throughout the holiday season,” Rental Escapes said.
The Bahamas
Beach Hilll (Source: Rental Escapes)
With accommodations for 12, The Beach Hill Estate in Harbor features five main buildings and is equipped with a 120-foot dock for deep-sea fishing, bone fishing and boat excursions.
The property includes a pool house with a full bar and kitchen with a full-service staff, a villa manager, housekeepers, and a gardener, with options to add a private chef and butler.
St. Martin
C'est la Vie (Photo Credit: Rental Escapes)
Set on Plumb Bay, St. Martin C’est La Vie accommodates 12 guests in six bedrooms. “Spacious outdoor living areas, a heated pool, an in-pool bar and an included private chef create an effortless setting for festive gatherings and memorable family meals,” Rental Escapes said.
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