Tennis & Pickleball, Longboat Key | Danielle Gladding & Co.

People choose a house on Longboat Key for the light and the water. What keeps them here, more often than not, is the standing Tuesday morning game.

Danielle Gladding lives in Queens Harbour inside Bay Isles and walks the neighborhood most mornings, which is how you learn which courts are busy and when. She does not play herself. She has been a licensed Florida Realtor since 1981 and a broker since 1987, and runs Danielle Gladding & Co. Realty with her daughter Alison Kanter.

Buyers arrive with a list — water view, garage, single level, hurricane shutters — and almost nobody puts “people to spend time with” on it, because it does not feel like something a house can provide. Then they move, and it turns out to be the thing that decides whether the second year here is better than the first.

This post is about racquet sports on Longboat Key, and specifically about The Tennis Gardens at the Resort at Longboat Key Club. Danielle is a member. What follows is what we tell buyers who mention tennis or pickleball in the first conversation — and what we tell the ones who do not, but probably should.

Start With the Surface

The courts at The Tennis Gardens are Har-Tru clay. Twenty of them, with four more tennis courts maintained on the resort side at Islandside.

If you have only ever played on hard court, the difference is not subtle and it is not cosmetic. Clay slows the ball and lets you slide into it. Points get longer. Placement and patience start beating raw power, which is why a well-constructed seventy-year-old regularly dismantles an athletic fifty-year-old on this surface and enjoys it enormously.

And it gives underfoot. Hard court returns every step to your knees, your hips, and your lower back. Clay absorbs a meaningful share of it. Across a decade of playing three mornings a week, that is the difference between still playing and having stopped.

We raise this early with buyers relocating from northern clubs, because it genuinely bears on where you buy. If your knees have started filing complaints, the surface at your future club is not a footnote.

Pickleball Has Eaten the Island, and That Is Fine

Communities like this one across the country have watched pickleball arrive and take over conversations that used to be about golf. Longboat Key is no exception, and the Club has leaned in rather than resisted.

At this time there are pickleball courts at the Tennis Gardens and a second set, the Marina Harbourside Pickleball Courts, down the same road at the marina. Hours differ between the two. Pickleball carries its own per-person fee rather than being bundled into general access, and the fee includes a paddle — you do not need to arrive equipped, which lowers the barrier for the curious considerably.

Open play runs daily, and players are rated before joining a session. That last piece is better administration than it sounds. Nothing kills a new player’s enthusiasm faster than being put on a court with three people well beyond their level, and nothing irritates strong players faster than the reverse.

For buyers whose tennis is winding down, or who never played anything and want in on something social, this is the door.

What Actually Gets Organized

Courts near your house are not the same thing as a program, and the program is what you are buying.

At this time the Tennis Gardens runs private lessons daily and group lessons and clinics every single day. The clinic slate has real variety: an early-morning session built for people who want to be off court before the Florida heat asserts itself, a daily technique clinic open to every level, a ninety-minute format split between drills and situational point play, and a fast live ball format for stronger players that is frankly a cardio workout with a racquet involved. Adult clinics run fourteen and up. There are junior summer clinics too, split by age with small groups — useful when younger guests are visiting in July.

Racquets, paddles, and a ball machine rent on site. There is a pro shop with stringing.

Two practical things nobody tells you until you are standing there. At this time courts are reserved twenty-four hours ahead in ninety-minute blocks, so spontaneity has a one-day lag. And running shoes are not permitted on court — clay requires proper court shoes, and people discover this the embarrassing way, once.

“I have watched more friendships start on those courts than at any dinner party on this island. That is not a marketing line. It is just what happens.”

— Danielle Gladding, Broker, Bay Isles resident and Club member

The Amenity That Matters Most Is a Desk

Here is the one we lead with, and it is not the courts.

At this time the Club runs a match-arranging service. You tell them your level, whether you want singles or doubles, and which days work for you. They find you people to play with. That is it. That is the service.

Now think about what relocating actually costs you. You leave a town where you knew the doctor, the neighbors, and the four people you played with every Tuesday for fifteen years. You arrive somewhere genuinely beautiful where you know no one, and the beauty turns out to be no help at all with that particular problem. The most common thing our relocating clients underestimate is not the taxes or the insurance or the hurricane season. It is how long rebuilding a circle takes, and how completely that timeline determines whether the move feels like a good decision by the second season.

A desk that puts a racquet in your hand and three strangers across the net, twice a week, compresses that timeline more than nearly anything else money can buy here. We have watched it work over and over. It is the first thing we point out to buyers moving here without existing ties, and it is why we sometimes build a morning clinic into a first visit rather than showing a fifth house.

How It Fits a Purchase

The Tennis Gardens belongs to the Club, not to Bay Isles or to any neighborhood. Nothing about buying a house on Longboat Key gives you racquet privileges automatically. Deeded Bay Isles Beach Club access on the Gulf does come with every Bay Isles home; tennis does not.

At this time the Club offers two membership types — a social membership, and a full membership carrying golf, tennis, and the broader amenity range. Membership is optional and separate from any home purchase. Resort guests can play as well, and the Club’s published lesson rates distinguish member pricing from social and resort guest pricing, with members paying less.

Which means the arithmetic is worth doing before you fall in love with a house.

Alison’s due-diligence note

Price the membership before you price the house. It is a recurring cost sitting entirely outside your mortgage, your taxes, and your association dues, and buyers who model the first three with great care routinely leave the fourth as a rounding error. Ask what the initiation runs, what annual dues run, what is included versus billed per use, whether court time itself carries a fee, and what happens to the obligation if you sell in three years. Then set your house budget. Doing it in that order has changed which neighborhood more than one of our clients ended up in — for the better.

If Racquet Sports Are Part of Why You Are Looking

Say so in the first conversation. It changes which neighborhoods we show you, and it changes how we build the visit. There is a version of a first trip to Longboat Key that includes a morning clinic at the Tennis Gardens, and it will tell you more about whether you would be happy here than four additional listings ever could.

Danielle lives inside the Bay Isles gates and is a Club member, so an introduction is a phone call rather than a project. Alison runs the numbers on what membership costs against everything else you would be carrying, which is the part that keeps the decision sound rather than romantic.

If you are selling on Longboat Key, we will give you a private valuation and a candid read on your home’s position in today’s market. Twenty minutes, on the phone or in person, no pitch. A private conversation costs nothing.

— Danielle & Alison | Danielle Gladding & Co. Realty

Frequently Asked Questions

Where can you play clay court tennis near Sarasota?

The Tennis Gardens at the Resort at Longboat Key Club is the largest clay court facility on the Longboat Key and Sarasota island chain, with 20 Har-Tru courts at 3100 Harbourside Drive plus four additional tennis courts on the resort side at Islandside. Cedars Tennis Resort at the north end of Longboat Key also maintains Har-Tru courts, so the island supports clay court players unusually well for its size.

Are the Longboat Key Club tennis courts clay or hard court?

The Tennis Gardens courts are Har-Tru clay. Clay slows the ball, rewards footwork and point construction over raw power, and absorbs a meaningful share of the impact that hard courts return to knees, hips, and back, which is why players commonly keep playing on clay well into their seventies and eighties.

Does the Longboat Key Club have pickleball?

Yes, at this time the Club runs pickleball at two locations: courts at The Tennis Gardens and the Marina Harbourside Pickleball Courts at 2630 Harbourside Drive. Play carries a separate per-person fee that includes a paddle, open play runs daily, and players are rated before joining an open play session so that groups are matched by level.

Do you have to be a member to play tennis at the Longboat Key Club?

Resort guests can play and take lessons at The Tennis Gardens at this time, so membership is not the sole route in. The Club’s published lesson rates distinguish tennis and full members from social members and resort guests, with members paying the preferential rate, so how often you intend to play changes which arrangement makes financial sense.

How do you find people to play with after moving to Longboat Key?

The Club operates a match-arranging service at this time, in which you specify your level, your preference for singles or doubles, and your available days, and staff pair you with suitable players. For buyers relocating without existing local ties, this is among the fastest and most reliable routes into a social circle on the island.

What tennis clinics does The Tennis Gardens run?

At this time The Tennis Gardens runs group lessons and clinics every day, including an early-morning drilling clinic designed to finish before the heat, a daily technique clinic open to all levels, a ninety-minute format split between drills and situational point play, and a high-intensity live ball format for stronger players. Adult clinics are offered for ages fourteen and up, with separate junior clinics running in summer.

How far in advance do you book a court at The Tennis Gardens?

Courts are reserved twenty-four hours in advance in ninety-minute increments at this time. Proper court shoes are required and running shoes are not permitted on the clay, which is worth knowing before a first visit.

Does buying a home on Longboat Key include Club membership?

No, membership at the Resort at Longboat Key Club is optional and entirely separate from any home purchase on Longboat Key, including in Bay Isles. Deeded access to the Bay Isles Beach Club on the Gulf does come automatically with every Bay Isles home, but tennis, golf, and the marina run through the Club instead, which makes membership a recurring cost worth pricing before setting a house budget.

More on the Area

Longboat Key — the island end to end
Bay Isles — the gated community at the south end

Danielle Gladding is a social member of the Longboat Key Club and does not golf or play tennis. She lives in Queens Harbour inside Bay Isles. She has been a licensed Florida Realtor since 1981 and a broker since 1987, and runs Danielle Gladding & Co. Realty with her daughter and Sales Partner Alison Kanter, who was born and raised in Sarasota and has been licensed since May 2023. Danielle: (941) 539-8535 · Alison: (941) 306-9786