
Holiday rentals with a kayak in Wailea
Find and book unique kayak rentals on Airbnb
Top-rated Accommodation with a Kayak in Wailea
Guests agree: these holiday homes with a kayak are highly rated for location, cleanliness and more.

Aloha Aku CoCoPalm Suite – Experience Tropical Bli
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. But is still centrally placed in Kihei nearly all of the amenities you might desire. BBKM 2013/0002

Oceanfront Dream 2Bed/2Bath-Mana Kai Maui Resort
Incredible location on Keawakapu Beach, the condo views beach & outer islands & has serene villa-like aesthetic with efficient design combining function and comfort! Enjoy dining on the private lanai or in the well-equipped kitchen w/island! Fine finishes, towels, linens, tasteful furnishings and decor make this the perfect choice! King Bed suite is OPEN to living space. WiFi. Smart tv. FREE Parking, Lounges, BBQs, pool, deli+store, fitness gym office, activity desk, 4 beach chairs+bch towels.

Direct Oceanfront View at Mahana Studio, King Bed
Welcome to my hotel-zoned oceanfront, direct ocean view studio Enjoy stunning floor-to-ceiling ocean views and breathtaking sunsets over the neighboring islands. See and hear the ocean from your bed and private lanai Featuring a king Murphy bed with a true king size mattress, central AC, smart TV, fast Wi-Fi, fully equipped kitchen, in-unit laundry Free on-site parking, 1 space No resort fees, no other additional fees Oceanfront, direct ocean view on the 4th floor of the Mahana at Ka'anapali

Maui Beachfront Oceanfront Sands of Kahana withA/C
Mar 10 -Mar 14 OPEN! 🌺 Ocean and Beachfront views at Sands of Kahana with ❄️Air Conditioning! 🏖️ Escape to Maui, Hawaii! Ocean/Beachfront Resort with onsite dining at Captain Jacks. This 5-star spacious 2 bed 2 bath condo offers breathtaking views, stunning sunsets over Molokai & Lanai. Enjoy whale 🐋 and turtle 🐢 watching, surfing 🏄♂️, and strolls along the sandy beach. Unwind with warm tropical breezes and libations 🥂 on the lanai. Enjoy the amenities 2 pools, 2 gyms, and Pickleball.

Gorgeous 2BR Westin Nanea Villa in Ka’anapali
Enjoy nature at its best in this upscale Maui beachside setting built in 2016. Managed by elegant Westin Hotels, Nanea is the newest and most ecological (LEED certified) villa development on the Ka’anapali coast. There is abundant snorkeling and whale watching right outside your door. Many restaurants and grocery stores are a short walk away… and charming Lahaina is only 10 minutes down the road via free shuttle or your car. Come relax in paradise! Enjoy the glamour of this elegant resort.

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

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.

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.

Endless Ocean Views - 1bd/2 bath
Experience island living at its finest in this beautiful 1-bedroom, 2-bathroom condo located in the heart of Wailea/Kihei, Hawaii. This serene retreat offers breathtaking ocean views and a peaceful atmosphere, perfect for unwinding after a day of exploring. Just a short stroll from world-renowned beaches and minutes from top-rated shopping, dining, and entertainment, the location couldn’t be more ideal. This well-appointed space is designed for comfort and relaxation.

Tropical Retreat • King • Beach • Pool/Hot Tub
Newly remodeled Maui retreat with a plush king bed, designer finishes, and a fully updated kitchen with stainless steel appliances. Bright, open layout with AC and a queen sleeper for added space. Step onto your private lanai overlooking lush tropical gardens, or unwind at the resort’s heated saltwater pool and jacuzzi. Professionally cleaned and thoughtfully stocked - perfect for relaxing, easy island living just moments from the beach.

Amazing Summer Discounts and Fantastic Ocean Views
Welcome to our ocean front dream retreat in Maui, where your senses are filled with the sights and sounds of azure waves and gentle breezes whispering through the palm trees. As soon as you enter through the door of our tropical abode, you'll be greeted by a symphony of light and space, where every corner radiates a welcoming coziness, and beautiful views of the ocean, marine wildlife, and the neighboring islands.

Top 5% Condo | Steps to Kamaole Beach
Wake up to ocean breezes and end your day with colorful Maui sunsets from your private lanai. This beautifully remodeled top-floor condo sits directly across from Kamaole Beach Park II, one of South Kihei's most beloved beaches. Enjoy peekaboo ocean views, resort pools and hot tubs, a king bed, beach gear, free parking, and walkable access to restaurants, shops, snorkeling, and unforgettable island adventures.
Popular amenities for Wailea kayak rentals
Holiday House Rentals with a Kayak

Aloha Aku Bamboo2 Suite – A Serene Sea Retreat

Serene Blue Retreat•Queen Bed•Smart TV•MiniFridge

Aloha Aku CoCoPalm2 Suite – Cozy Beachfront Escape

Maui Sunset Resort A102 - Aloha Mai, Remodel, Grou

Aloha Aku Hula2 Suite – Beachfront Bliss

Aloha Aku Ohana2 Suite – Relaxing Garden Views Awa

Maui Sunset A102 - Aloha Mai 2, Beachfront Resort

Aloha Aku Honu2 Suite – Relax by the Sea in Tranqu
Other holiday rentals with a kayak

WBH D116 Aloha Wai – Garden Suite Steps from ocean

WBH D227 Aloha Lai – Breathtaking Ocean Views

The Whaler Resort 359 ~ Upgraded With Ocean Views

Kaanapali Shores 259~Ocean Views & Hear the Waves

Maui Eldorado B206 ~ Big Corner Unit & Large Lanai

Maui Sunset B102 - Aloha Tai 2, Beachfront Resort

Hokulani 612 at Honua Ka ~Upgraded with Ocean View

Luana 14D~ Villa with Garage, BBQ & Pool Access
Quick stats about holiday rentals with a kayak in Wailea

Total holiday rentals
Explore 20 holiday rentals in Wailea

Nightly prices starting at
Wailea holiday rentals start at $259 NZD per night before taxes and fees

Verified guest reviews
Over 220 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space and kid-friendly amenities

Holiday rentals with a pool
20 properties feature pools

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
20 of Wailea holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Wailea rentals

4.8 Average rating
Wailea stays are highly rated by guests—averaging 4.8 out of 5!
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- Maui
- Kamaole Beach Park II
- Kaanapali Beach
- Lahaina Beach
- Wailea Beach
- Honolua Bay
- Polo Beach
- Kapalua Bay Beach
- Old Lahaina Luau
- Whalers Village
- Ka'anapali Golf Courses
- Maui Vista Condominium
- Big Beach
- Black Rock Beach
- Black Sand Beach
- Maui Ocean Center
- Kihei Kai Nani
- Hāmoa Beach
- Maui Arts & Cultural Center
- Peahi
- KOA Resort
- Haleakala National Park
- PacWhale Eco-Adventures
- Kahana Beach
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