Holiday rentals with a kayak in Kaanapali

5 out of 5 average rating, 37 reviews

Condo in Kihei

WBH D227 Aloha Lai2 – Unwind by the Oceanfront

This family-friendly remodeled beachfront, second floor 1-bedroom/1-bath air-conditioned Condo Suite comes with a comfortable king-size bed and living room couch that pulls out to a queen size sofa-sleeper allowing the unit to sleep up to 4 people. Just steps from the beach, the awe-inspiring multi-island views from the shore are unlike any other. You can enjoy this gorgeous view from your covered lanai. Gorgeous granite counter tops in the kitchen and bathroom along with new appliances and fixt

4.98 out of 5 average rating, 129 reviews

Condo in Kihei

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.

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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!

4.82 out of 5 average rating, 17 reviews

Condo 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

4.98 out of 5 average rating, 121 reviews

Penthouse on Sandy Swimmable Beach Incredible View

Zoned "Hotel/Resort" so no need to worry about our zoning. 9th floor Penthouse 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

4.9 out of 5 average rating, 181 reviews

Book Your Maui Whale Watching Maui Escape!

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.

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Home in Kihei

4.87 out of 5 average rating, 158 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.

4.96 out of 5 average rating, 203 reviews

Condo in Wailea

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!

5 out of 5 average rating, 39 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.

4.84 out of 5 average rating, 157 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.

4.95 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.

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