caribbean tennis resorts

TRO Properties Shine in 5 of Tripadvisor’s Top 10 Best of the Best Caribbean Destinations

Tripadvisor recently unveiled its Travelers’ Choice Awards list of the top 10 Caribbean hotspots, recognizing the region’s best of the best destinations. Among these standout spots, five are home to Tennis Resorts Online (TRO) properties, offering travelers the perfect blend of world-class tennis and stunning oceanside settings. Whether you’re seeking a relaxing getaway or an active vacation, these TRO-affiliated destinations provide an unforgettable experience.

While exact resorts were not part of Tripadvisor’s nominating process, we researched which TRO listings were in each country to provide you with a breakdown of properties you may be interested in enjoying if a Caribbean retreat is on your 2025 must-do list. From stunning white sand beaches to all-inclusive luxury to racquet sports programming that almost outshines the coastal views, these 13 resorts offer guests an unrivaled experience in the sun.

Here is the full list of the top Caribbean destinations as highlighted by Tripadvisor:

  1. Aruba
  2. Cuba
  3. Dominican Republic
  4. Puerto Rico
  5. Jamaica
  6. St. Martin / St. Maarten
  7. St. Lucia
  8. Curaçao
  9. Barbados
  10. Basse-Terre Island

Explore five of these 10 locations within our list below, and find the resort that just might be your perfect match.

No. 3 of 10: Dominican Republic

The Dominican Republic enchants visitors with its blend of pristine white-sand beaches and charming “gingerbread” Victorian architecture. Boasting 900 miles of stunning Caribbean coastline, this island is a paradise for beach lovers. Must-visit spots include Puerto Plata, where a cable car ride up Mount Isabel de Torres offers breathtaking views, and Cabarete, known for its lively nightlife set to the rhythm of steel drum beats. The breezy palms and shimmering waters of Punta Cana complete the picture of a tropical haven.

Casa de Campo Resort & VillasLa Romana, La Romana, Dominican Republic

Nestled on 7,000 subtropical acres, Casa de Campo stands out as one of the Caribbean’s most iconic resorts, combining luxurious amenities with unparalleled accessibility and charm.

Key Features

  • Golf: Three Pete Dye-designed courses, including the world-famous “Teeth of the Dog”
  • Tennis: 13 Har-Tru courts (10 lighted) at the stunning La Terraza Tennis Center
  • Recreation: A private beach, watersports, polo fields, equestrian center, and shooting club
  • Culture: Altos de Chavón, a 16th-century artisan village replica with galleries, restaurants, and a 5,000-seat amphitheater
  • Travel: Three international airports within an hour’s drive; the nearest is just 10 minutes away

Club Med Punta CanaLa Alta, Punta Cana, Dominican Republic

Located on 75 picturesque acres in Punta Cana, this Club Med enjoys a prime beachfront setting along nearly 2,000 feet of soft, golden sand, protected by an offshore reef. With consistently warm temperatures around 80°F, it’s the perfect destination for a Caribbean getaway.

Key Features

  • Tennis: 13 hard courts (6 lighted)
  • Pickleball: 8 courts available for play
  • Activities: Circus workshops, Mini Club for kids, and watersports
  • Accommodations: Upscale two-bedroom family suites (Tiara) with stunning oceanfront views
  • Travel: About 30 minutes from the Punta Cana International Airport (PUJ)

Tortuga Bay Hotel at Puntacana ResortHiguey, Punta Cana, Dominican Republic

Experience the pinnacle of Caribbean luxury at Tortuga Bay, a AAA Five Diamond Award-winning resort designed by the iconic Oscar de la Renta. Nestled in Punta Cana, this exclusive retreat combines timeless elegance with the natural beauty of the Caribbean. A dedicated personal Embajador ensures your every need is attended to, allowing you to fully relax and enjoy the tranquil surroundings.

Key Features

  • Tennis Courts: 12 courts, including 9 clay, 1 Har-Tru, 1 natural grass, and 1 hard Deco-Turf court
  • Additional Racquet Sports Facilities: 4 paddle courts and 2 pickleball courts
  • Amenities: Tennis pro shop, snack bar, and a state-of-the-art Technogym
  • ITF-Standard Courts: 4 courts built to International Tennis Federation standards, ideal for ATP players and Grand Slam preparation

No. 4 of 10: Puerto Rico

Puerto Rico is a perfect mix of vibrant nightlife and serene retreats. San Juan’s Spanish colonial architecture sets the stage for a day of shopping and exploring. Nature enthusiasts can hike through the expansive El Yunque rainforest to discover waterfalls, stone towers, and colorful wildlife. For beach lovers, Isla de Vieques is a must-see, especially Mosquito Bay, where bioluminescent microorganisms light up the waters with a mesmerizing blue-green glow under the moonlight.

Wyndham Grand Rio Mar Puerto Rico Golf & Beach ResortRío Grande, Río Grande, Puerto Rico

Set on 481 stunning acres along Puerto Rico’s north coast, just 19 miles from San Juan Airport, Wyndham Grand Rio Mar Puerto Rico Golf & Beach Resort offers breathtaking ocean and mountain views alongside a wealth of recreational amenities.

Key Features

  • Tennis Courts: 13 courts, including 11 clay and 2 hard courts
  • Golf: Two 18-hole courses designed by Greg Norman and Tom & George Fazio
  • Recreation: Watersports center, fitness center, bicycle rentals, and multiple pools, including a kiddie pool
  • Family-Friendly: Club Iguana programs for children ages 4–12
  • Additional Amenities: Mandara Spa, 12 restaurants and lounges, and a casino

El Conquistador Resort & Country ClubFajardo, Fajardo, Puerto Rico

Perched on a stunning oceanfront location in Fajardo, El Conquistador Resort offers breathtaking views of the ocean, tropical gardens, and neighboring islands. This premier Caribbean destination combines luxury, adventure, and relaxation for an unforgettable escape.

Key Features

  • Tennis Courts: 2 outdoor hard courts near the main lobby, available for casual play and lessons with professional staff
  • Recreation: Coqui Water Park, Palomino Island adventures, and a pristine golf course
  • Amenities: Multiple pools, fine dining, and a luxurious open-air lobby with panoramic ocean views

No. 5 of 10: Jamaica

In Jamaica, basking under the warm island sun is only the beginning of the adventure. Known as “the land of wood and water,” its lush forests offer prime hiking and bird-watching opportunities. History enthusiasts can explore heritage sites in Trelawny, while music lovers will revel in the vibrant reggae and dancehall scene in Kingston. Montego Bay is ideal for snorkeling and shopping, while the tranquil spas of Ocho Rios provide the perfect escape for relaxation and rejuvenation.

Couples Swept Away – NegrilMiramar, Negril, Jamaica

Set along Negril’s stunning seven-mile beach, Couples Swept Away is an all-inclusive resort that blends luxury with active pursuits, catering to couples and singles seeking a vibrant Caribbean getaway.

Key Features:

  • Tennis Courts: 9 lighted courts (5 clay, 4 hard)
  • Pickleball: 4 lighted courts for casual play and organized activities
  • All-Inclusive: Accommodations, meals, drinks, fitness classes, watersports, golf, and scuba diving included
  • Tennis Programming: Daily tennis clinics for all levels, round-robin tournaments (Monday–Friday), and private lessons with three experienced local teaching professionals

The Tryall ClubMontego Bay, St. James, Jamaica

Set on 2,200 picturesque acres of lush, rolling hills 10 miles west of Montego Bay, The Tryall Club combines historic charm with world-class tennis and luxurious accommodations. Centered around an 18th-century Georgian Great House, this premier destination offers sweeping views of Jamaica’s north coast and an unmatched sense of exclusivity.

Key Features

  • Tennis Courts: 9 courts (4 Agile Turf and 5 Nova Cushion hard courts) with professional-grade surfaces and scenic hilltop views
  • Pickleball: 4 courts, accommodating all ages and skill levels
  • Accommodations: 86 villas, ranging from 1 to 8 bedrooms, most with private pools and full staffing, including housekeeper, butler, and cook
  • Tennis Programming: Weekly clinics, private lessons, and social round-robin tournaments, and equipment rentals, racquet stringing, and regripping services

Round Hill Hotel & VillasMontego Bay, St. James, Jamaica

Tucked away on a secluded 100-acre peninsula, Round Hill Resort in Montego Bay offers timeless luxury and exclusivity. Just 25 minutes from Sangster International Airport, this iconic destination combines breathtaking beauty with impeccable service.

Key Features:

  • Tennis Courts: 5 courts, including 3 Har-Tru green clay courts and 2 lighted for night play
  • Tennis Programming: Private lessons and specialized clinics with experienced in-house pros, including Calvin, who has been with the resort for over 25 years; Equipment rental available for guests who don’t bring their own.

Half Moon ResortMontego Bay, St. James, Jamaica

Located near Montego Bay on a lush 400-acre estate, Half Moon has transformed from a quaint cottage colony into a premier resort destination featuring an array of luxurious amenities and sports facilities. This includes a notable racquet sports complex directed by former touring pro and Caribbean Davis Cup player, Robert Hale.

Key Features

  • Courts: 17 courts within a comprehensive racquet sports complex (nine floodlit tennis courts and eight pickleball courts)
  • Additional Sports Facilities: Robert Trent Jones golf course, watersports center, croquet lawns, squash courts, and a fitness center, including yoga or aerobics classes
  • Tennis Programming: Private lessons, adult & youth clinics, and more for both tennis and pickleball)

Sandals South CoastWestmoreland Parish, Cornwall, Jamaica

Immerse yourself in the water-inspired luxury of Sandals South Coast, a sprawling all-inclusive resort set along a 2-mile pristine stretch on the south coast of Jamaica. This unique resort embraces its coastal setting with extraordinary water-themed architecture and amenities, from Overwater Villas to a one-of-a-kind Overwater Wedding Chapel.

Key Features

  • Tennis Courts: 4 courts offering various tennis programs, lessons, and clinics for all skill levels
  • Pickleball: 8 dedicated courts for guests to enjoy
  • Unique Accommodations: Beachfront swim-up suites and the revolutionary Rondoval Village with swim-up access
  • Water-Themed Innovations: Over-the-Water bar and Blue Mahoe Overwater Villas

No. 6 of 10: St Martin / St Maarten

This unique destination offers the experience of two distinct cultures—French and Dutch—within a compact 37-square-mile island. St. Martin/St. Maarten is a captivating blend of urban charm and natural beauty. From rain forest-like landscapes to pristine white beaches, the island’s physical diversity is matched by its rich cultural fusion. Visitors can also explore caves, encounter fascinating wildlife, and soak up the island’s vibrant atmosphere.

La Samanna, A Belmond HotelLes Terres Basses, Collectivity of Saint Martin, Saint Martin

Nestled on the pristine shores of Baie Longue, La Samanna offers a luxurious 5-star escape on the Caribbean island of Saint Martin. Known for its elegant accommodations and exceptional service, the resort promises an unforgettable beachfront experience.

Key Features

  • Tennis Courts: 3 omni courts, available day and night exclusively for hotel guests
  • Tennis Programming: Personalized lessons with a resident pro, bookable through the concierge
  • Accommodations: Spacious rooms with private balconies, satellite TV, free Wi-Fi, and plush oversized cotton towels
  • Dining: Gourmet meals at L’Oursin, poolside dining at Baie Longue Bar, and in-room terrace options paired with selections from the extensive wine cellar
  • Activities: Luxury spa services and sailing excursions to nearby islands

Coming 2027: Vie L’Ven Resort & ResidencesIndigo Bay Blvd, Saint Maarten

Set amidst a tropical paradise where lush wilderness meets the serene turquoise waters of Indigo Bay, Vie L’Ven Resort & Residences will offer a redefined luxury escape in St. Maarten. Slated to open for High-Season 2027/2028, this 280-room resort and residence will seamlessly blend elegance, privacy, and state-of-the-art amenities for an unparalleled island living experience.

Key Features

  • Planned Racquet Sports Facilities & Luxury Amenities:
    • Pickleball & Tennis Courts
    • 3 restaurants & 2 bars
    • Three outdoor pools, including adult-only options and a Beach Club
    • State-of-the-art fitness center
    • 24-hour concierge
    • 30,000 square foot thermal spa & a nature reserve
    • A private yacht dock & on-beach water sports
    • Childcare services

Keep an eye out for more releases and news related to this stunning property aimed at redefining luxury living in St. Maarten.

No. 9 of 10: Barbados

Barbados is an island of romance and adventure, with experiences tailored to every traveler. The calm waters on the west coast provide perfect swimming conditions, while the east coast attracts surfers with its competition-grade waves. Wherever you venture, expect turquoise waters, soft sandy beaches, and the chance to indulge in catamaran cruises. Culinary enthusiasts will also delight in the island’s delicious local fare.

Sandy LaneSt James, St James, Barbados

Nestled within an ancient mahogany grove on Barbados’ Platinum Coast, Sandy Lane is an iconic luxury resort offering unparalleled elegance and tranquility. Overlooking a pristine 1,000-foot crescent of coral sand beach and turquoise waters, the resort has been the choice of discerning travelers for more than six decades.

Key Features

  • Tennis Facilities: 11 floodlit tennis and padel courts, with complimentary access for guests and lessons available from a professional coach
  • Prime Location: Set on the Platinum Coast, with a tranquil beach and breathtaking ocean views
  • Legacy of Luxury: Renowned for exclusive privacy, decadent relaxation, and world-class leisure

Best Time to Visit These Tennis Resorts in the Caribbean

Wondering when to plan your ultimate tennis getaway? The Caribbean’s tropical climate ensures year-round playability, but the best time to visit depends on your preferences. Peak season runs from December to April, when the weather is at its finest—warm, sunny days with little rain. This is also the busiest time, meaning courts and resorts will be lively, offering the best opportunities for social play and high-level instruction. Many resorts, such as Half Moon in Jamaica and Sandy Lane in Barbados, also host seasonal round-robin tournaments and special events during these months.

For those looking to enjoy these world-class resorts with fewer crowds and better rates, the off-season from May to November is a great option. While occasional rain showers are more common, the courts remain open, and resorts often offer discounted rates and more personalized tennis instruction. Some resorts feature cutting-edge facilities that will redefine tennis and pickleball experiences in the Caribbean, making them an exciting choice any time of year. Whether you’re chasing ideal playing conditions or looking for a quieter, budget-friendly stay, each of these award-winning destinations ensures an unforgettable tennis vacation.

How to Choose the Right Tennis Resort for You

Choosing the perfect tennis resort starts with understanding what you want from your vacation. If improving your game is a priority, look for resorts with top-tier coaching, clinics, and professional instruction, such as Half Moon in Jamaica or Oscar de la Renta Tennis Center in the Dominican Republic, where expert pros offer lessons for all skill levels. More advanced players may prefer destinations like The Tryall Club, which attracts serious enthusiasts and offers organized round-robins and tournaments.

Traveling with family? Resorts like Couples Swept Away in Jamaica and Rio Mar Beach Resort in Puerto Rico cater to all ages with junior programs, kids’ activities, and multi-sport options. If you’re seeking a luxurious adult-focused retreat, La Samanna in St. Martin or Sandy Lane in Barbados provide serene beachfront settings with spa services and private accommodations. For those who enjoy multi-sport experiences, Vie L’Ven in St. Maarten offers state-of-the-art tennis, pickleball, and fitness amenities in a modern, high-end environment.

Whether you’re looking for high-level training, a social tennis scene, or a relaxing getaway with occasional play, selecting a resort that aligns with your preferences ensures an unforgettable Caribbean tennis experience.

Plan Your Ultimate Tennis Getaway to the Caribbean

With their breathtaking locations, world-class tennis facilities, and exceptional service, these Caribbean resorts offer something for every tennis-loving traveler. Whether you’re a dedicated player looking for high-level coaching or a casual enthusiast wanting to mix sport with relaxation, these destinations provide the perfect balance of competition, recreation, and luxury.

Ready to plan your next tennis vacation? Tennis Resorts Online offers in-depth reviews, firsthand traveler experiences, and expert insights to help you find the ideal destination. Visit the site to explore more about these resorts, compare amenities, and read feedback from fellow tennis enthusiasts. Have a favorite Caribbean tennis resort or a personal experience to share? Leave a comment or review to help other travelers make the most of their next tennis getaway!




  JOIN >> TRO Travel Club
  SOCIALS >> LinkedInInstagramFacebook
  SUBSCRIBE >> Tennis Resorts Online Newsletter
  READ MORE >> Travel Inspiration
  READY TO TRAVEL >> Inquire Here

READ MORE
READY TO TRAVEL
Picture of Jordana Klein

Jordana Klein

Jordana has blended her passion for racquet sports with her on-court skills as Tennis Resorts Online's Travel Editor. After competing at the Division 1 collegiate level, Jordana's journey led her to hold marketing positions with organizations such as the USTA, IMG's Miami Open, and IMG Academy. She continues to share her love for the game across TRO's network and on tennis and pickleball courts in the Tampa Bay area.

Tennis News

Ocean breezes, rustling palmettos, vibrant flowers, and a racquet sports schedule that’s ideal ...
kiawah island golf resort

Suggested Destinations

United States

Please complete the form below to pre-register for the TRO Travel Club. Once the Travel Club launches, you will be contacted with the complete list of benefits and invite to join.

Tennis Resorts Online

Receive our latest news & travel offers straight to your inbox