Where Luxury Travelers Are Spending the Holidays in 2026, According to Rental Escapes

Luxury Villa Rental Company Shares Destinations and Villas with Availability Ahead of High Season

MONTREAL – July 27, 2026 – Rental Escapes, a full-service luxury villa company specializing in providing private villa experiences worldwide, today revealed the destinations seeing the highest demand for the 2026 holiday season. As families and groups increasingly swap crowded resorts for private, personalized celebrations, warm-weather destinations across Costa Rica and the Caribbean have emerged as the top choice for travelers looking to celebrate together.

“The holidays have always been about bringing people together, and we’re seeing more families and groups look for ways to create those meaningful moments in destinations where everyone can stay together,” said Brian Schwimmer, chief executive officer and co-founder of Rental Escapes. “This year’s top destinations offer the perfect combination of warm weather, memorable experiences, and spacious villas where everyone can stay under one roof. Our award-winning Guest Experience team of concierge specialists is curating some of the season’s most memorable villa stays, crafting personalized itineraries and arranging everything from private chefs for holiday feasts to once-in-a-lifetime local experiences before guests even arrive. Villa travel allows families to focus on what matters most: spending quality time together.”

Based on holiday booking trends, these are the destinations luxury travelers are choosing for festive escapes this year, along with standout villas that still have availability:

1. Costa Rica – Costa Rica continues to be one of the fastest-growing destinations for holiday travel, appealing to families seeking a mix of adventure and relaxation. Visitors can spend their days surfing, ziplining through rainforests, spotting wildlife or unwinding on the beach before gathering for chef-prepared dinners in a private villa. Standout properties include Villa Motmot in Tamarindo and Casa Hamacas in Hacienda Pinilla, both designed for multigenerational groups. Located in the heart of Tamarindo, Villa Motmot comfortably accommodates up to 12 guests with easy access to sailing, horseback riding and hiking, while Casa Hamacas in Hacienda Pinilla welcomes up to 14 guests with a private pool, outdoor living spaces and nearby beach, golf and tennis amenities. To view all of Rental Escapes’ luxurious villa rentals with holiday availability in Costa Rica, click here.

2. Dominican Republic – The Dominican Republic remains a perennial favorite thanks to world-class golf, beaches, marinas and family-friendly activities. In Casa de Campo, guests can enjoy championship golf, sailing, horseback riding and beach clubs before retreating to villas like Ocean Bliss. 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. To view all of Rental Escapes’ luxurious villa rentals with holiday availability in the Dominican Republic, click here.

3. Jamaica – Jamaica offers a slower-paced holiday escape, where families can spend their days snorkeling, kayaking, enjoying authentic cuisine and soaking in the island’s laid-back culture. Hidden Bay by the Sea (Runaway Bay) is perfect for families of 12 or less. This unique property 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. To view all of Rental Escapes’ luxurious villa rentals with holiday availability in Jamaica, click here.

4. Turks & Caicos – Turks & Caicos continues to be a favorite for luxury holiday escapes thanks to its powder-soft beaches, crystal-clear turquoise waters and laid-back atmosphere. Whether guests spend their days snorkeling, paddleboarding, boating or simply unwinding by the sea, the destination offers the perfect setting for families to reconnect over the holidays. Cabuya, tucked away in one of Leeward’s most exclusive communities, welcomes up to 12 guests with an infinity-edge pool, private dock and expansive indoor-outdoor living space. The villa provides direct access to kayaking and paddleboarding while offering plenty of room for families to gather throughout the holiday season. To view all of Rental Escapes’ luxurious villa rentals with holiday availability in Turks & Caicos, click here.

5. The Bahamas – The Bahamas offers two distinct holiday experiences: the pink-sand charm of Harbour Island and the cosmopolitan energy of Nassau. Situated in the Narrows section of Harbour Island, The Beacon Hill Estate accommodates 12 guests and consists of five main buildings. A 120-foot boat dock serves as a direct launch point for deep-sea fishing, bone fishing, and boat excursions. Groups can gather at the pool house with a full bar and kitchen or view the bay from the elevated Pink Gazebo. The estate includes a full-service staff with a villa manager, housekeepers, and a gardener, with options to add a private chef and butler. Meanwhile, located in the gated Old Fort Bay community in Nassau, Villa Oceane, a seven-bedroom beachfront villa, accommodates up to 14 guests. The property provides direct access to the beach alongside an outdoor pool, a jacuzzi, and a detached, fully equipped gym. The open-concept interior includes a professional kitchen and seven king bedrooms with private terraces. A six-member staff is included with the villa, featuring a private chef, sous-chef, bartender, and three housekeepers to manage all meals and daily services. The villa is located seven minutes from the Nassau international airport. To view all of Rental Escapes’ luxurious villa rentals with holiday availability in the Bahamas, click here.

6. St. Martin – St. Martin combines French-Caribbean cuisine, beautiful beaches and island hopping, making it ideal for travelers who want both relaxation and vibrant dining. C’est La Vie, situated directly on Plum Bay, is a contemporary six-bedroom villa welcoming up to 12 guests. 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. To view all of Rental Escapes’ luxurious villa rentals with holiday availability in St. Martin, click here.

As Costa Rica and the Caribbean lead the surge in warm-weather holiday travel, and multigenerational groups grow to an average of 14 guests, Rental Escapes provides the ultimate solution for families seeking to gather under one roof. With a curated global portfolio providing spacious, luxury villas and a dedicated Concierge team to handle every detail no matter the hour, celebrating the holidays has never been a more effortless, personalized experience.

To view more standout villas in the Rental Escapes portfolio and to book your 2026 holiday getaway, click here.  

For more information on Rental Escapes, visit RentalEscapes.com. Stay up-to-date on the latest news by following Rental Escapes on Facebook Facebook.com/RentalEscapes, Instagram @RentalEscapes, Twitter @RentalEscapes and LinkedIn.

MEDIA NOTE: Hi-res images can be found HERE.

About Rental Escapes

Rental Escapes is a full-service luxury villa company that prides itself in providing top-notch personalized service and unforgettable villa experiences. The company offers a hand-picked selection of more than 5,000 carefully vetted and curated luxury villa rentals in 155+ destinations across the Caribbean, Mexico, Europe, the United States and beyond. Its team of highly trained villa specialists assist guests and travel advisors in planning and booking the ideal villa stay. In addition, every reservation is provided with a concierge service to take care of arranging everything from private chefs to boat charters.

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