Holiday rentals with a kayak in Kaanapali

4.82 out of 5 average rating, 11 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.

4.97 out of 5 average rating, 113 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.

4.87 out of 5 average rating, 47 reviews

Home in Paia

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!

4.79 out of 5 average rating, 14 reviews

Apartment in Kaanapali

Hokulani 108 at Honua Kai ~ Upgraded Ground Floor

You'll love this ground floor, updated one bedroom condo with full access to all Honua Kai Resort amenities. A spacious syn-grass lawn gives the kids plenty of room to play while you relax and enjoy the fresh ocean air. A short stroll takes you to one of Maui's best beaches, swimming pools, Duke's restaurant, or the 24-hour gym. This resort has all the amenities you need for a dream Maui vacation: 7 pools, a waterslide, hot tubs, BBQs & more! Enjoy the good life & book with Maui Westside today

4.89 out of 5 average rating, 19 reviews

Makena Surf: Maui on the Beach

Welcome to Unit 303 in Building G at the Makena Surf Resort! NEW LISTING due to new ownership (Jan 24). The new owners have invested a great amount of money into replacing outdated linens and fixtures with high end items not reflected in photos. You will be staying on the third floor in a 2-bedroom, 2-bathroom condo with 1,038 SF of living space overlooking an incredible hidden snorkel & swim beach (Chang's). You simply cannot get closer, or have better access, to better beaches in Maui.

4.88 out of 5 average rating, 154 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.

4.95 out of 5 average rating, 100 reviews

Apartment in Lahaina

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.

4.95 out of 5 average rating, 118 reviews

Apartment in Lahaina

Majestic Ocean Front Views!

Our beautiful ocean front one bedroom condo with direct ocean views is the perfect place to relax and enjoy an amazing Hawaiian experience! NOTE: The total amount quoted on the airbnb app includes: the nightly rate, our local housekeepers fee, Hawaii tax, and the airbnb fee. We are literally just a few steps from our beautiful sandy beach, where you can snorkel, swim, or rent a standup board or kayak. Our lanai is perfect for whale watching and relaxing on our comfortable lounges.

4.83 out of 5 average rating, 24 reviews

Luxury Oceanfront Mana Kai Resort Condo

Plan your ideal Hawaiian escape and book a stay at this 2-bedroom, 2-bath vacation rental located in Mana Kai Maui Resort. Nestled on the shores of Keawakapu Beach, this ocean-front condo provides luxury furnishings, panoramic ocean and pool views throughout it’s interior space, and everything you’ll need for an unforgettable getaway. Spend your days lounging by the pool, snorkeling in the crystal blue waters, teeing off at local golf courses, or perusing The Shops at Wailea!

4.84 out of 5 average rating, 151 reviews

Place to stay in Wailuku

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.

4.96 out of 5 average rating, 194 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.

4.9 out of 5 average rating, 181 reviews

Apartment in Lahaina

Maui May Flash Sell, Stay for $189/Night!

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!

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Popular amenities for kayak rentals in Kaanapali

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House rentals with a kayak

JackieRating, 5 stars74 months ago

Aloha Aku Bamboo2 Suite – A Serene Sea Retreat

Such an amazing place! It’s in the middle of Kihei but feels like you’re on a private retreat. Located at the end of a beach so you essentially have it to yourself. The beach out front is a little rocky, so you may want water shoes. But there are so many great beaches in the area, it really doesn’t matter. Communication was great leading up to check-in and throughout the stay. The unit was clean and the pools/hot tub out front were a great perk! Thanks for a great stay!

5 out of 5 average rating, 3 reviews

Aloha Aku CoCoPalm Suite – Experience Tropical Bli

AshleyRating, 5 stars76 months ago

We had the most amazing time. All of the small touches were there, and we were constantly surprised by the high level of service and pride in the property. You cannot beat the view, and the hot tub is awesome! The unit was stocked with the nessesities, as well as delightful extras. The bed was incredibly comfortable, and the cherry on top was the ducks!! So charming. We cannot wait to come back!

5 out of 5 average rating, 17 reviews

Aloha Aku CoCoPalm2 Suite – Cozy Beachfront Escape

GregRating, 5 stars2 months ago

Great and comfortable stay. Loved the sunset views. Very walkable beach right out front, and it was great having all the accessories like beach chairs and other gear available to take to nearby snorkeling spots and coves. Gary and Sarah and the Aloha Aku team were communicative and quick to reply, and they'll really have pit a lot of energy into making the property inviting and relaxing. Note - the bathroom is within the bedroom area and not fully enclosed, so there's not much privacy in that regard. Not an issue, just something to be aware of if booking as a group.

5 out of 5 average rating, 3 reviews

Private room in Wailuku

Hawaiian owned Room 2 w/ shared Pool

RachelRating, 5 stars16 months ago

I highly recommend staying here. The hosts Delamarie, Kepeli and Kevin were very helpful and gracious and I really did feel at home. I was very inspired by their aloha❤️Wailuku is an amazing little town at the foot of the stunning Iao Valley. Thank you so much and I will definitely be back!!

4.91 out of 5 average rating, 85 reviews

Maui Sunset Resort A102 - Aloha Mai, Remodel, Grou

JackieRating, 5 stars2 weeks ago

Great stay! Walk from the lanai straight onto a beautiful lawn. Very peaceful and relaxing. It was just a short walk on the grass to the ocean. Grounds were very well maintained. The condo was very clean and nicely decorated.

5 out of 5 average rating, 6 reviews

Aloha Aku Hula2 Suite – Beachfront Bliss

NicoleRating, 5 stars13 months ago

Aloha Aku has been everything we wanted, and more. The photos and descriptions don't do it justice. We were originally booked for five days, but extended our trip twice, for a total of 10 days because everything here is just so perfect!

5 out of 5 average rating, 5 reviews

Aloha Aku Ohana2 Suite – Relaxing Garden Views Awa

TimRating, 5 stars26 months ago

When we arrived, we got confused trying to find the entrance, but if you read the instructions carefully, you should be fine! I had the most communication and clearer instructions here than anywhere else I've stayed with AirBnB-like places! The property is beautiful, the beach there is great for walks and sights, but not the best for swimming/snorkeling as it is usually murky. The hot tub and pools are really neat. The accommodations are exactly as described and really well done.