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

Home in Kihei

4.86 out of 5 average rating, 14 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.

Guest favorite

Condo in Kihei

4.98 out of 5 average rating, 125 reviews

Tropical Kihei Resort | 3 Min Walk to Beach | A/C

NEW kitchen remodel, new floors & paint! Professionally CLEANED. Plush King size Sealy bed, all new kitchen and bathroom cabinets, stainless steel appliances, full size washer dryer, tile & LV floors throughout. Beautiful furniture, artwork throughout, granite countertops, high end linens, Queen sofa sleeper with 5" FOAM mattress. After the beach relax and enjoy sipping a beverage and lounging on your private lanai overlooking the tropical grounds. A/C units in BOTH the living area & bedroom.

Top guest favorite

Home in Paia

4.88 out of 5 average rating, 48 reviews

Beach house for wind-sports in Pa’ia-North Shore

Fast wi-fi, private beach. A charming, Hawaiian beach house, built in 1952. Private beach steps away. A great spot for kite surfing, windsurfing, wing foiling, SUP, or swimming! We are just between Kanaha Beach Park and Camp One/Sprecks. The house has 3 bedrooms with 2 bathrooms all on ground level. This property is organic, free of pesticides & chemicals, with many local fruit trees and a spacious lawn complimenting a private Hawaiian spot by the water. A dream for water sports enthusiasts!

Guest favorite

Condo in Lahaina

4.9 out of 5 average rating, 181 reviews

Fall Flash Sale – $159/Night in Maui!

Annie’s Surf Shack, an oceanfront escape 30 feet from the Pacific! A/C, stunning sunsets, fast Wi-Fi, free parking, and no resort fees. Relax on your lanai, walk to beaches, shops, and dining, or explore West Maui with ease. Short-term rentals are legal in Maui for the foreseeable future. Annie’s Surf Shack remains fully licensed, compliant, and ready to share the aloha. Super clean, ideally located. No check-ins on major holidays. To learn more about us, search for Annie’s Surf Shack Maui.

Guest favorite

Home in Kihei

4.87 out of 5 average rating, 157 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

4.94 out of 5 average rating, 104 reviews

Direct Beachfront A/C & on Sandy Swimmable Beach

Zoned "Hotel/Resort" so no need to worry about our zoning. 8th floor unit on a sandy swimmable beach with A/C. 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, 2 gyms. Washer/dryer inside the unit. Fully stocked kitchen. Pak n play & highchair.

Condo in Lahaina

4.96 out of 5 average rating, 123 reviews

Maui Beachfront Oceanfront Sands of Kahana withA/C

🌺 Ocean and Sandy Beachfront views at Sands of Kahana with ❄️Air Conditioning! 🏖️ 🌴 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.

Top guest favorite

Condo in Kihei

4.96 out of 5 average rating, 202 reviews

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

Exquisitely remodeled top floor condo in one of the most desirable condo complexes in South Maui. Enjoy sunsets and peekaboo ocean views from your private lanai, walk to some of the finest beaches, shops & restaurants and lounge in the multiple pools & hot tubs on property with this perfect Hawaiian oasis! Everything (and we mean everything) is fully remodeled. From a peaceful island getaway to your next Hawaiian adventure, Makana Condo is ready for your enjoyment!

Top guest favorite

Condo in Lahaina

5 out of 5 average rating, 38 reviews

Papakea Penthouse K-401 2 Bed 2 Bath with A/C

We invite you to experience one of Papakea's finest top floor, end units K-401. (Fun Fact: Papakea means crest of the wave in Hawaiian) This 2 BD 2 BA penthouse unit underwent a complete renovation in 2022. The Papakea facility fee is $25 per day paid by the guest upon check in and a $50 incidental hold that would be released to their card when you check out. The tax is a 17.97% on your nightly room rate and is something the state of Hawaii requires us to collect.

Guest favorite

Condo in Kaanapali

5 out of 5 average rating, 11 reviews

Hokulani 712 at Honua Kai ~Ocean View XL-1 Bedroom

Welcome to your dream Maui vacation rental condo! Hokulani 712 at Honua Kai Resort offers the perfect retreat for those seeking a relaxing and luxurious getaway. This oversized one-bedroom condo sleeps 2 adults and boasts gorgeous ocean views from the large lanai! Located on the top floor (7th floor) of the south side of the Hokulani tower, this unit features a large 235 sq ft lanai with spectacular views of the ocean and the island of Lana'i in the background.

Superhost

Place to stay in Wailuku

4.85 out of 5 average rating, 156 reviews

Stall #4 Safe place to sleep in your vehicle

Discover the perfect haven for budget travelers looking for a secure and comfortable place to rest! Our offering is ideal for those parking and sleeping in their cars or RV rentals, and it comes without the extra cost of a room. Enjoy the convenience of an outhouse and hot showers available during business hours, ensuring you feel refreshed and rejuvenated. Experience peace of mind with our fully fenced yard, designed for your privacy and security.

Guest favorite

Condo in Lahaina

4.95 out of 5 average rating, 122 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 to relax and enjoy an amazing Hawaiian experience! You'll be just steps away from our beautiful beach, where you can snorkel, swim, or rent a standup board or kayak. Our lanai is perfect for whale and turtle watching as well as relaxing and taking in the breathtaking beauty of Maui.