Your Hawaiian vacation deserves more than just beach lounging, it deserves unforgettable moments, fun on the water, and the kind of memories that define your trip. At Windward Watersports, we’re here to help you make the most of every day in paradise.
We’re a locally owned and operated rental shop just minutes from the world-renowned Kailua Beach, offering high-quality gear, personalized service, and the local knowledge to help you explore with confidence. With a 4.4-star rating from 90+ Google reviews, we’re proud of the trust we’ve built with visitors from around the world — one board, paddle, and smile at a time.
Whether you’re looking to surf, paddle, cruise, or kayak, our goal is simple: make it easy, fun, and hassle-free. We offer a full range of ocean and beach rentals including surfboards, stand-up paddleboards (SUP), single and tandem kayaks, and beach cruiser bikes, all chosen to suit local conditions and all experience levels.
Our location in the heart of Kailua makes it easy to get out on the water quickly — and if you’re staying nearby, we even offer delivery to your vacation rental or the beach. No need to haul gear or strap anything to your roof. We’ll meet you where the adventure begins.
Kailua is one of Oʻahu’s most stunning destinations, with calm, clear waters, offshore islets, and soft white sand. Whether you’re paddling to the Mokulua Islands, catching a wave at Castles, or just cruising the streets of Kailua Town on a bike, there’s no shortage of ways to experience the magic of the Windward side.
Our team knows the area inside and out — and we’re always happy to offer tips, weather updates, and suggestions to match your plans. First time on a paddleboard? Want to know the best kayak route for sea turtle sightings? Need a board for small waves? We’ve got you. We’ll set you up with the right gear and even give you a quick demo if needed before you head out.
We also keep things flexible. Book online in advance to lock in your rental, or drop by the shop if you’re feeling spontaneous. Our booking process is quick and easy, and our team is here every day to make sure you’re ready to roll — or paddle.
Prefer a slower pace? Our beach cruiser bikes are perfect for exploring Kailua at ground level. Ride along scenic coastlines, grab some shave ice, or explore local shops and cafés — all without worrying about parking or traffic. It’s the island lifestyle on two wheels.
At Windward Watersports, we believe in providing more than just gear — we offer freedom, flexibility, and the chance to truly enjoy your time on Oʻahu’s east side. Whether you’re a solo traveler, a couple, or a family with kids in tow, we’re here to help you dive into adventure your way.
Come see why so many visitors choose us as their go-to spot for rentals in Kailua. Affordable rates, a laid-back vibe, and friendly local service — it’s everything you need to make your day at the beach unforgettable.
There’s no better place to catch a wave than Kailua — where mellow, rolling surf meets turquoise water and warm island sun. Whether it’s your first time standing up or you’re ready to carve into the next set, we’ve got the perfect board for your style and skill level.
With soft-tops, performance boards, and everything in between, our surfboard rentals make it easy to get out and ride. Just steps from the beach — pick up a board and paddle out.
Stand-Up Paddleboarding (SUP) is one of the most relaxing and scenic ways to experience Kailua Bay. Cruise over vibrant coral reefs, drift alongside sea turtles, and take in the lush mountain views, all at your own pace.
Our top-quality paddleboards are stable, beginner-friendly, and ready for adventure. Whether you’re up for a solo paddle or want to explore with friends, SUP is a must-do activity for your Oʻahu stay.
Kailua is famous for its offshore islands and calm, inviting waters — and the best way to explore them is by kayak. Set out on your own island-hopping adventure, discovering hidden beaches, tide pools, and wildlife along the way.
We offer premium single and tandem kayaks, launch-ready and easy to use. Whether you’re planning a quick paddle or a full day of exploration, your Kailua kayak journey starts here.
There’s something magical about pedaling through a beach town with the wind in your hair and the scent of plumeria in the air. Our beach cruiser rentals are the perfect way to experience the local charm of Kailua at your own pace.
Take a slow ride along the ocean, stop for shave ice, or cruise to a hidden beach — no traffic, no rush, just island vibes. Great for couples, families, and anyone who wants to see Oʻahu from a different perspective.
