Vacation rentals with a kayak near Kaanapali Beach

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Top-rated kayak rentals near Kaanapali Beach

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Guest favorite

Condo in Kihei

4.96 out of 5 average rating, 143 reviews

Renovated 2BD/2BA | 3 Min Walk to Beach | A/C

Come unwind in this newly remodeled 2BD/2BA condo across from the Charley Young/ Kamaole I beaches. Walking into this soothing space you will be greeted with a gorgeous garden view. Master bedroom has a queen size bed, TV, its own AC unit & en-suite bathroom. 2nd bedroom has large closet & its own AC. Spacious living room, with large screen TV & AC, is suited with a comfortable couch that also turns into a full-size sleeper sofa. Cozy kitchen is equipped with everything you need to cook & enjoy.

Superhost

Campsite in Wailuku

4.91 out of 5 average rating, 126 reviews

Stall #1 Safe place to sleep in your vehicle

We have incorporated our fitness business into our listings. Upon purchasing a personal training package, you will have a free Safe place to park and sleep in your own camper van or car. NO room included in this package! Along with the security of a fully fenced-in yard/ garden we offer Outside Hot Water Shower Outside potty Lounge furniture Wi-Fi in designated area Phone/ Lap Top only charging station AND the use of the swimming pool. Use of kayaks and beach items to 2 or more night stays.

Guest favorite

Home in Kihei

4.89 out of 5 average rating, 9 reviews

Aloha Aku Honu2 Suite – Relax by the Sea in Tranqu

Tranquil Beachfront Estate w/ 5 Luxurious Private Full Suites & Exotic Fruit Grove. Full amenities. Our luxury Beachfront estate has 4 beachfront one-bedroom suites and a garden view two-bedroom Ohana. Each suite has a private entrance, separate living room, full kitchen and is like having your own condo at the beach in Maui. This special place is hidden behind a private, double gated entrance, lined with 700 ft of lighted coconut palms that lure you into the feeling of leaving the world behind.

Condo in Kihei

4.81 out of 5 average rating, 36 reviews

Best Beaches! Remodeled End Unit for Luxury and Pr

Relax your days away at a safe, lifeguarded, sandy beach with gentle surf, waters teeming with tropical fish and turtles--where is this slice of paradise? Right across the street from your stylish and spacious 2-bedroom/2-bath condo! No need to load the family in the car: just grab the cooler, beach chairs, umbrella and beach towels (all provided in your unit) and walk to some of the best swimming and snorkeling on Maui! We hope you find our Aloha Kahakai elsewhere for a better ra te!! :-)

Top guest favorite

Condo in Lahaina

5 out of 5 average rating, 128 reviews

Panoramic Views right on a Sandy Swimmable Beach

Zoned "Hotel/Resort" so no need to worry about our zoning. 4th Floor Corner unit on a sandy swimmable beach with A/C. The secondary bedroom also has huge windows, en-suite bath and its own (2nd) lanai. Perfect location for watching the beautiful sunsets, see our resident sea turtles and an excellent place for spotting whales during the whale migration season. Beach towels, boogie boards, 4 beach chairs, cooler and much more... Kiddie pool, family pool, pickle ball courts, tennis courts.

Guest favorite

Home in Kihei

4.89 out of 5 average rating, 148 reviews

Cajudoy's Hale - STKM 2O13-OO18/TA-081-709-8752-01

WONDERFUL! Three bedroom hale (home) in the Central Kihei area of Maui. Wood floors, lots of space, kitchen fully stocked, BBQ and so much more. Great for kids, elderly, and young at heart. This house is your home away from home. We have all of the necessary items for a home. If we do not have something please let us know and we will try our best to accommodated. Walking distance to the beach, shopping, park, public transportation, etc... You will not find a better place in Kihei.

Guest favorite

Condo in Lahaina

4.95 out of 5 average rating, 109 reviews

Maui Beachfront Oceanfront Sands of Kahana withA/C

🌺 Ocean/ Beachfront views at Sands of Kahana w/ Air Conditioning! 🏖️ Hurry 7/24-8/20 now available! 🌴 Escape to NW Maui Ocean/Beachfront Resort with onsite dining. Enjoy spacious 2 bed 2 bath accommodations w/breathtaking views, stunning sunsets over Molokai & Lanai. Enjoy whale 🐋 and turtle 🐢 watching, surfing 🏄‍♂️, and strolls along the sandy beach. Unwind with tropical breezes and libations 🥂 at the onsite Captain Jack's Restaurant. Amenities 2 pools, 2 gyms, and Pickleball.

Superhost

Condo in Lahaina

5 out of 5 average rating, 4 reviews

Whaler 420: Upgraded 1 Bed/1 Bath With Ocean Views

• Stunning 1BR/1BA renovated condo with breathtaking ocean views • Renovated with upgraded kitchen and luxury shower • Cal King bed in the primary bedroom, Queen-size sleeper sofa in the living room • Full-size washer and dryer in the unit for longer stays or active families (rare find!) • Private lanai to enjoy morning coffee and watch whales in the winter • Access to Whaler Resort amenities including fitness center, beachside gas grills, pools, hot tub, and more

Top guest favorite

Condo in Kihei

4.96 out of 5 average rating, 188 reviews

Top 5% Home with King Bed + Steps to Beach & Shops

Top-floor condo just a 5-minute walk from South Maui’s best beaches, restaurants, and shops! Fully remodeled with modern island style, this bright unit features a private lanai with peekaboo ocean views, a king bed, fast Wi-Fi, Smart TV, and all the beach gear you need. With pools, hot tubs, and tennis courts on site, this is your dream Kihei escape—perfect for couples or small families.

Guest favorite

Condo in Lahaina

4.89 out of 5 average rating, 180 reviews

Your Maui Vacay — A/C and Amazing Ocean Views!

Welcome to Annie’s Surf Shack Maui—your oceanfront escape just 30 feet from the Pacific! Enjoy A/C, stunning sunsets, fast WiFi, free parking, and no resort fees. Relax on your lanai, walk to beaches, shops, and dining, or explore West Maui with ease. Super clean, fully legal, and packed with aloha. No check-ins on Thanksgiving, Christmas, or New Year’s Day—please plan ahead!

Guest favorite

Condo in Lahaina

4.95 out of 5 average rating, 114 reviews

Majestic Views from our little home under the sun

Our beautiful ocean front one bedroom condo with direct ocean views is the perfect place for whale watching and spotting the many turtless on our beach. We are literally just a few steps from our beautiful sandy beach, and our lanai is perfect for having meals or just relaxing on our comfortable lounges. We also have great snorkeling, no need to drive anywhere.