Twenty-four million Americans played pickleball in 2025 — up nearly 172% in three years, and close to sixfold over five, according to the Sports & Fitness Industry Association. A good share of them belong to a club, a league or a standing group that plays together three mornings a week, and sooner or later somebody in that group says: we should all go somewhere warm and play.
That is where it gets complicated, because a pickleball group is not a normal booking. You need enough courts for everyone to play at once rather than rotate for an hour, you need somewhere the non-players are happy for a week, and you need a room block that works for a group where not everyone arrives as a couple. Most “best pickleball resorts” lists solve none of that.
Why an all-inclusive works well for this
For a group, the all-inclusive format solves the two things that usually go wrong. Nobody has to settle a bill. No splitting dinner fourteen ways, no arguments about who ordered the second round, no one quietly opting out of a restaurant because it is expensive. And everything is in one place — courts, meals, bar, beach and rooms — so a group of eighteen can be together without organising transport every evening.
It also makes the trip easy to sell to your group. One number per person, flights aside, and everyone knows what they are committing to.
The constraint nobody mentions: who can share a room
This is the first question to settle, and it eliminates entire brands before you look at a single court.
Sandals is couples-only. Every room is sold to two adults travelling as a couple. That is a serious problem for a typical pickleball club, which will include single players, widowed players, friends who want a twin room, and same-sex pairs who are not a couple. Sandals has by a distance the best pickleball infrastructure in the Caribbean — and if a third of your group cannot book a room there, it is the wrong resort.
Beaches — the family sibling of Sandals — takes any room configuration and any age, which makes it the natural fallback if your group has children or non-couple pairings. Casa de Campo, Club Med and the Hyatt Inclusive Collection properties all take singles and mixed configurations too.
Ask your group how they will pair up before you shortlist resorts. It is a five-minute question that saves an embarrassing reversal later.
The resorts worth shortlisting
We have deliberately kept this short. Court counts are the most unreliable figure in this corner of travel — brands, aggregators and press releases routinely contradict each other — so every number below comes from the resort or brand’s own current information, and where we could not verify a count we say so rather than inventing one.
Sandals South Coast, Jamaica — the biggest pickleball facility here
Sandals lists twelve dedicated courts at South Coast, and states the resort can accommodate up to 48 players at once. For a club of twenty that means genuine simultaneous play rather than a queue. Whitehouse is quiet, the beach is long, and the resort is a good distance from the Montego Bay crowds. Couples-only.
Sandals Regency La Toc, Saint Lucia — ten courts and better scenery
Ten dedicated courts, on one of the more dramatic resort settings in the Caribbean. Saint Lucia takes longer to reach from the Midwest than Jamaica, usually with a connection, which is worth weighing for a group where several people will grumble about a long travel day. Couples-only.
Sandals Royal Curaçao — eight courts, and somewhere different
Eight dedicated courts, on an island outside the hurricane belt with a genuinely different feel from Jamaica. The newest of the three big Sandals pickleball properties. Couples-only.
Casa de Campo, Dominican Republic — the strongest organised programme
The Racquet Center currently lists eight pickleball courts alongside eleven Har-Tru tennis courts and four padel courts, with lighting for evening play. More importantly it runs a real programme rather than just holding courts: group clinics from a minimum of three people at $35 per person per hour, private lessons, hitting partners, social mixers that match players by level, and custom tournaments arranged from a minimum of eight players. If your group wants structured play and a coach, this is the strongest option on the list.
One important caveat: Casa de Campo is not natively all-inclusive. It sells room-only rates with an optional Casa Inclusive package, and the Racquet Center clinics and lessons are priced separately regardless. It is frequently mis-described as an all-inclusive online. Budget it differently from the others.
Beaches Turks & Caicos — for groups with families
Beaches includes pickleball in its resort inclusions and runs the same programme structure as Sandals. We are deliberately not quoting a court count: the brand publishes a fleet-wide figure across both Beaches resorts rather than a per-property number, and third-party sources disagree with each other. Confirm the count for your dates before committing a group. What Beaches offers that Sandals cannot is any room configuration and any age — which for a club trip with children along is decisive.
Pineapple Beach Club Antigua — a smaller adults-only option
Caribbean Journal reports six pickleball courts at this adults-only Elite Island Resorts property on Long Bay, describing play as guest-organised rather than programmed. We could not verify the count on the resort’s own site, so treat it as a lead to confirm rather than a fact — but for a smaller adults-only group that wants something less corporate than the big brands, it is worth a call.
Club Med also has pickleball at Punta Cana, Michès Playa Esmeralda, Cancún and the adults-only Turkoise in Turks & Caicos, with instruction and open play available. No Club Med page we could reach publishes court counts, and a widely repeated figure in the trade press could not be verified — so we are not printing one.
| Resort | Where | Courts | Room policy |
|---|---|---|---|
| Sandals South Coast | Whitehouse, Jamaica | 12 dedicated | Couples only |
| Sandals Regency La Toc | Castries, St Lucia | 10 dedicated | Couples only |
| Sandals Royal Curaçao | Curaçao | 8 dedicated | Couples only |
| Casa de Campo | La Romana, DR | 8, plus clinics and tournaments | Any configuration |
| Beaches Turks & Caicos | Providenciales | Confirm for your dates | Any configuration, all ages |
| Pineapple Beach Club | Long Bay, Antigua | Reported as 6 — confirm | Adults only |
Sandals also lists smaller court counts at Montego Bay, Ochi, Saint Vincent, Royal Bahamian, Dunn’s River and Grande Antigua, and hybrid — that is, shared or lined-over — courts at Royal Plantation, Negril, Halcyon Beach and Grenada. For a group, dedicated courts matter: a hybrid court is a tennis court with pickleball lines on it, and it will not be available whenever someone is playing tennis.
Courts are not the whole story
The distinction that matters for a club is organised play versus loose courts. A resort with eight courts and no programme gives you eight courts. A resort with a programme gives you round-robins, someone to run them, and a way for the weaker players in your group to have a good week rather than a discouraging one.
On current evidence the genuine programmes are: Casa de Campo (priced clinics, level-matched social mixers, tournaments on request from eight players), and Sandals and Beaches fleet-wide — complimentary introduction sessions, daily pick-up play, solo-player matching, weekly tournaments and paid private and group lessons, with lit courts for early morning and evening play. Sandals and Beaches were named USA Pickleball’s official all-inclusive resorts in April 2025 and have USA Pickleball-approved coaches on staff.
Everywhere else on this list, on what is currently published, you are getting courts rather than a programme. That is fine if your group organises its own play — most clubs do — but it is not the same purchase.
Reserving courts for your group
This is the question to ask in writing at contracting, because almost no resort publishes a court-booking policy. The one hard fact available: Sandals and Beaches offer group tournaments and reserved court times for parties of ten rooms or more. That is the clearest published commitment in the market and it is a good reason to hit the ten-room threshold if you are close to it.
For everywhere else, get it in the contract or in an email from the group department before you take deposits. Specifically: how many courts your group can hold, for which hours, on which days, and whether other guests can book into them. A club that turns up expecting eight courts at 8am and finds three is a club that will not travel with you again.
How a group booking actually works
Group terms differ by brand, and the two we can document give a fair sense of the shape.
Sandals takes groups from five rooms with a $1,000 group deposit, with the headline discount tier at ten rooms and up. Comp room credits run at one per ten paid rooms from January to August, and one per six paid rooms from September to December, capped at five credits. Three paid nights minimum. Groups are contracted only outside 45 days of arrival, deposits scale with size, and there are blackout dates around late December and Valentine’s.
Hyatt Inclusive Collection takes groups from ten rooms, with one comp room per fifteen paid, World of Hyatt signing-bonus points to the group leader on a sliding scale by size, up to 15% off group spa bookings, a VIP welcome amenity, one room upgrade per ten rooms to a maximum of four, and a deposit of $50 per room. No cancellation or attrition penalties until 96 days before arrival, which is unusually generous and worth knowing.
The generalisable version: ten rooms is the common threshold, a comped room falls somewhere between one-per-six and one-per-sixteen depending on brand and season, everything is contracted and deposit-driven, and the attrition cliff sits somewhere between 45 and 96 days out. Those dates are the ones that catch group organisers — the point at which unsold rooms become your problem rather than the resort’s. Our guide to all-inclusive group vacations covers the mechanics in more depth.
Skill levels, and keeping everyone happy
The commonest way a pickleball trip disappoints is not the courts. It is a 4.0 group and a 3.0 group trying to share a week. A few things that help:
- Split the mornings. Competitive play early, social play later, rather than mixing every session.
- Use a level-matched mixer if the resort runs one. Casa de Campo does this explicitly; Sandals and Beaches match solo players into games.
- Book a clinic on day one. It gives the weaker players a structured start and it gets the group playing together before the pecking order sets.
- Consider a tournament on the last full day — Casa de Campo will arrange one from eight players, and Sandals and Beaches run weekly tournaments you can slot into.
- Bring your own paddles and balls. Resort equipment varies, and outdoor balls behave differently from what your group plays with at home.
The people who are not playing
Every pickleball group has them — the spouse who came for the beach, the partner who plays once and then reads for six days. They are also the people most likely to veto the trip, so choose the resort partly for them.
What matters: a beach worth spending a day on, a spa, at least one excursion worth doing, and enough dining variety that a week does not feel repetitive. This is where the big all-inclusives beat a dedicated racquet property — the non-players get a real holiday rather than a week beside a court. If you want the resort itself to be the draw for the non-playing half, our guide to adults-only all-inclusive resorts and the all-inclusive resort guide both cover the properties on their own merits.
Getting everyone there
The travel day is where groups fray. A few practical points:
- Do not let people book their own flights independently if you can avoid it. A group arriving across nine different flights is a group where somebody misses the transfer and somebody else waits two hours at the airport.
- Jamaica, Punta Cana and Turks & Caicos take the most direct service from the Midwest. Saint Lucia, Curaçao and Antigua almost always mean a connection — fine for a keen group, less fine for a mixed one.
- Arrange transfers as a group rather than individually. Ask the resort’s group department what they can coordinate; this is not usually published and is usually possible.
- Buy insurance. On a group booking with deposits and an attrition deadline, one person’s cancellation is everyone’s problem. Our travel insurance guide covers what actually matters.
- Set your own internal deadline two weeks before the resort’s attrition date. It gives you time to release rooms without penalty.
Let us organise it
Group bookings at all-inclusives are contracted, deposit-driven and full of dates that matter — and the person who volunteers to organise the club trip usually discovers that halfway through. That is the part we do: the room block, the contract, the concessions, the transfers, the attrition deadlines and the chasing.
Tell us roughly how many rooms, how many are couples and how many are not, when you want to go, and how competitive the group is, and we will come back with two or three resorts that genuinely fit — and we will tell you which ones cannot take your room configuration before you fall in love with them.
We compare available supplier offers, agency promotions and added amenities to help you find strong overall value. Planning fees are $0. Group concessions, court facilities and programmes vary by resort, date and availability, and should be confirmed at contracting.
Start with the Where2Next survey, or get in touch and tell us about your group.
Pickleball group vacation FAQs
How many rooms do I need to qualify as a group?
Usually ten, though Sandals contracts groups from five rooms. Ten is where the meaningful concessions start at most brands, and it is also the threshold at which Sandals and Beaches offer reserved court times and group tournaments.
Which Caribbean resort has the most pickleball courts?
Of the properties we can verify from the brand’s own current information, Sandals South Coast in Jamaica has the most, with twelve dedicated courts and capacity for up to 48 players at once. Sandals Regency La Toc has ten and Sandals Royal Curaçao eight. Casa de Campo lists eight alongside a full tennis and padel centre.
Can a mixed group of couples and singles book Sandals?
No. Sandals is couples-only and every room is sold to two adults travelling as a couple. If your group includes single players or friends sharing a twin, look at Beaches, Casa de Campo, Club Med or the Hyatt Inclusive Collection properties instead. This is the most common reason a pickleball group has to change resorts late.
Can we reserve courts just for our group?
Sandals and Beaches publish reserved court times and group tournaments for parties of ten rooms or more. Elsewhere it is negotiable but rarely published — get the specific hours and court numbers in writing before you take deposits from your members.
Is Casa de Campo all-inclusive?
Not by default. It sells room-only rates with an optional inclusive package, and racquet-centre clinics and lessons are charged separately either way. It is often described online as an all-inclusive; budget it as though it is not.
What about the players who are not very good yet?
Book a clinic early in the week and use a level-matched mixer if the resort runs one. Casa de Campo matches players by standard for its social sessions, and Sandals and Beaches run complimentary introduction sessions and match solo players into games. Splitting competitive and social play into different time slots does more for group harmony than anything else.
When should we book?
Six to twelve months out for a group of any size, and earlier for peak weeks. Group contracts are usually written outside 45 days of arrival at the latest, comp-room ratios are better in the autumn months at some brands, and the good resorts run out of contiguous rooms long before they run out of rooms.
What do the non-players do?
Everything the resort offers — beach, pools, spa, excursions, dining. Choosing a full-service all-inclusive rather than a dedicated racquet property is exactly how you keep the non-playing half of the group happy for a week.