
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.

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.

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.

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!! :-)

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.

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!

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.

Paradise at its Best KS5310
Beautiful condo overlooking pool, tropical gardens and ocean! You can’t find a better location! Across the street from one of the most popular beaches on the south side, where whales breach (in whale season) and sea turtles swim along with you. There is a hot tub, large pool, tennis court, on property. Restaurants, golf courses and shopping all surround this great location! Book your reservation! You won’t be disappointed! Sofa bed, makes a group of 3 possible.

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.

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.

Top 1% Home with King Bed + Steps to Beach & Shops
Fully remodeled top-floor condo in one of South Maui’s most popular complexes! Take in stunning sunsets and peekaboo ocean views from your private lanai. Walk to beautiful beaches, shops, and restaurants, then relax in the resort-style pools and hot tubs. Every detail has been thoughtfully designed for comfort and style. Whether you’re here to unwind, explore Maui, or enjoy a bit of both, Makana Condo is the perfect island getaway.

Makena Surf B-208 | Luxury Oceanfront Condo
Makena Surf B-208 is a luxurious oceanfront retreat offering panoramic Pacific views and direct beach access. This fully upgraded condo features a gourmet kitchen, elegant furnishings, and an expansive lanai perfect for sunsets. Enjoy resort amenities including two pools, Jacuzzis, tennis and pickleball courts, and lush gardens. Ideal for relaxation or adventure, it’s minutes from Wailea dining, golf, and world-class snorkeling.

Top Floor Oceanfront great snorkeling (MKM809)
Hawaii Tax ID: TA-190-792-2432-01 Step out onto your large private lanai and sunbathe on the lawn chairs or enjoy appetizers and drinks as you overlook your incredible ocean views. Watch whales breaching in the winter months right from your lanai. You will also have views of Haleakala and the swimming pool from this amazing piece of paradise.
Popular amenities for Wailea kayak rentals
Holiday House Rentals with a Kayak

Aloha Aku Bamboo2 Suite – A Serene Sea Retreat

Aloha Aku CoCoPalm Suite – Experience Tropical Bli

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
Other holiday rentals with a kayak

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

Hawaiian owned fully furnished TENT #1

Calming Vibes in Room 2

Oceanfront Dream 2Bed/2Bath-Mana Kai Maui Resort

Endless Ocean Views - 1bd/2 bath

Aloha Aku Honu2 Suite – Relax by the Sea in Tranqu

Maui Sunset Resort B102 - Aloha Tai, Ground floor,

Last Minute Deal! Oceanview! 2 Bed 2 Bath LOFT!
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 $209 AUD 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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- Kamaole Beach Park II
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