Best Luxury Pickleball Resorts of 2026: Caribbean, Florida, and Beyond
At Healthy Travel, we believe the best trips leave us healthier than when we arrived—not simply rested, but more active, more connected, and more inspired. That's why we're drawn to experiences that enrich both the journey and the traveler. Pickleball's rise at luxury resorts is one of the best examples we've seen.
Pickleball has quickly become one of luxury travel's fastest-growing amenities. From the Caribbean to the South Carolina Lowcountry, these six exceptional resorts are redefining the sport through world-class courts, thoughtful programming, and unforgettable settings.
When I started playing pickleball, I never expected it to lead to some of my closest friendships. By your first pickleball game, you're on a first-name basis. By your sixth, you're rearranging your weekend plans around the people you've just met.
So when I say pickleball has gone from a backyard curiosity to a five-star amenity, I'm not just tracking a trend—I'm reporting from inside it. From a Rockefeller-founded hideaway in the British Virgin Islands to a century-old racquet institution in South Florida, some of the world's most storied resorts have spent the past few years quietly building courts, hiring dedicated pros, and treating pickleball less like a passing fad and more like the next great social amenity.
Perhaps it's no surprise that pickleball's greatest strengths—its accessibility, inclusiveness, and social nature—are exactly what luxury hospitality has been about all along.
Photo credit: Aurora Anguilla
For the Dedicated Player
Aurora Anguilla Resort & Golf Club | Anguilla, British West Indies
If one resort demonstrates just how seriously luxury hospitality is embracing pickleball, it's Aurora Anguilla.
The 300-acre resort—formerly CuisinArt Resort, reimagined under Best Buy founder Richard M. Schulze and now managed by Salamander Hotels & Resorts—features 11 championship pickleball courts alongside five hard tennis courts, all fully lit and oriented north-south for optimal play. It's one of the Caribbean's largest dedicated pickleball facilities.
The programming reflects that commitment. Certified professionals lead clinics for every skill level, junior instruction, family programs, and immersive multi-day pickleball experiences. Evening play under the lights extends matches well after sunset.
Its philosophy is different from that of many luxury resorts: less about intimacy and more about creating a true pickleball destination. Whether you're picking up a paddle for the first time or looking to sharpen your competitive game, Aurora has invested in the kind of thoughtful infrastructure that encourages guests to play every day of their stay. The result is one of the Caribbean's most comprehensive pickleball programs—and a resort that's clearly betting on the sport's future.
Photo credit: Montage Palmetto Bluff
For a True Sense of Community
Montage Palmetto Bluff | Bluffton, South Carolina
Not every luxury pickleball experience is defined by the number of courts. At Montage Palmetto Bluff, it's the atmosphere that sets it apart.
The Wilson Lawn & Racquet Club is owned and operated by the Palmetto Bluff community rather than the resort itself. While Montage guests enjoy full access, the club isn't open to the public—a distinction that creates an experience rooted in the destination rather than designed solely for visitors.
Six dedicated pickleball courts sit alongside eight Har-Tru tennis courts, bocce and croquet lawns, shaded courtside pavilions, and a thoughtfully curated pro shop. Professional instruction, private lessons, and reservable courts allow guests to play at their own pace, whether they're joining friends for an afternoon match or refining their game with one-on-one coaching.
Staying at Montage means playing where the community plays—on courts built first for residents and thoughtfully shared with resort guests. It fits naturally within the easy rhythm of this 20,000-acre Lowcountry retreat, where active mornings often give way to leisurely afternoons on the river, bike trails, or porch swings overlooking the marsh.
Photo credit: The Boca Raton
For Racquet Sport Tradition
The Boca Raton | Boca Raton, Florida
Few domestic resorts can match The Boca Raton's history with racquet sports. Tennis has been woven into the property's identity for nearly a century, making its embrace of pickleball feel less like trend-chasing and more like the next natural evolution.
Today, the recently enhanced Racquet Club features 12 hard-surface pickleball courts alongside 14 Hydro-Grid tennis courts, all supported by a full-service racquet concierge. The playing surfaces are engineered to remain up to 20 percent cooler than conventional courts—a meaningful advantage under the South Florida sun.
Guests can choose from private instruction with certified pickleball professionals, clinics for every skill level, junior programming, and social play. Between matches, the Racquet Bar serves fresh juices, healthy fare, and signature cocktails, making it as much a social hub as a place to recharge between matches.
It helps that Boca Raton has emerged as one of the country's strongest pickleball communities, with several top-ranked professional players living nearby. The result is one of Florida's most sophisticated pickleball programs—and a resort where it's surprisingly easy to build an entire vacation around time on the courts.
Photo credit: Four Seasons Nevis
For Effortless Luxury
Four Seasons Resort Nevis | Nevis, West Indies
Some resorts add pickleball because guests expect it. Four Seasons Resort Nevis approached it differently—by folding it seamlessly into one of the Caribbean's most respected racquet sports programs.
Managed by Troon Peter Burwash International and recently recognized as the 2025 Resort Tennis Centre of the Year, the Sports Pavilion added four dedicated pickleball courts to its existing collection of hard, clay, and artificial grass tennis courts, with five courts available for evening play.
Programming is led by Director of Racquet Sports Tim Gottesman, a former NCAA Division I player, with daily clinics offered from November through May. This summer, the resort is making it even easier to get on court through a seasonal flat-rate program available through October 31, 2026, which includes unlimited golf, tennis, and pickleball throughout a guest's stay, along with complimentary golf clubs, racquets, and paddles.
It's a thoughtful approach that removes nearly every barrier to getting on the court, whether they're seasoned players or picking up a paddle for the very first time. Rather than treating pickleball as a novelty, Four Seasons Nevis has simply extended the same level of service, instruction, and attention to detail that has defined its racquet program for decades.
Photo credit: The Tryall Club
For Timeless Elegance
The Tryall Club | Montego Bay, Jamaica
There are resorts with pickleball courts, and then there is The Tryall Club.
This storied private club in Jamaica has long been known for its traditional all-white dress code, Wimbledon-style ball attendant service, and one of the Caribbean's most respected tennis programs. Rather than reinventing itself for pickleball, The Tryall Club has simply welcomed the sport into a culture that has celebrated racquet sports for decades.
Six pickleball courts complement the club's nine-court Tennis Club overlooking Montego Bay, featuring advanced pro-grade playing surfaces, complimentary guest access, weekly clinics, open play, tournaments, leagues, and instruction for every level of player.
It's a destination that embraces one of the world's fastest-growing sports without sacrificing the traditions that have made it an institution. At a time when many luxury resorts are still deciding what pickleball should look like, The Tryall Club proves the sport doesn't need reinvention to feel luxurious. Sometimes the greatest luxury isn't what's new—it's the confidence to honor tradition while embracing what's next.
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