
Vacation rentals with a kayak in Wailea
Find and book unique kayak rentals on Airbnb
Quick stats about vacation rentals with a kayak in Wailea

Total vacation rentals
Explore 40 vacation rentals in Wailea

Nightly prices starting at
Wailea vacation rentals start at $120 per night before taxes and fees

Verified guest reviews
Over 220 verified reviews to help you choose

Family-friendly vacation rentals
30 properties offer extra space & kid-friendly amenities

Vacation rentals with a pool
30 properties feature pools

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
40 of Wailea vacation 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!
Top-rated kayak rentals in Wailea
Guests agree: these kayak rentals 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
LocationViewSleep quality

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.
Outdoor spacesLocationHospitality

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!! :-)
LocationOutdoor spacesAir conditioning

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.
ValueLocationCondition

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!
LocationLaundryHospitality

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.
LocationOutdoor spacesFamily

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.
LocationOutdoor spacesWifi

Ocean View Paradise at Makena Surf #C-103
Makena Surf C-103 is a beautifully updated two-bedroom condo in the gated Makena Surf Resort. The unit features a king bed in the master suite, two full-size beds in the guestroom, central air conditioning, a fully equipped kitchen with wet bar, and high-speed internet. Guests enjoy resort amenities including pools with Jacuzzis, tennis and pickleball courts, fitness center, private lanais, and direct beach access for sunsets and seasonal whale watching.
LocationSleep qualityAccuracy

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.
Outdoor spacesValueAccess

Makena Surf: Maui on the Beach
Welcome to Unit 303 in Building G at the Makena Surf Resort! You will be staying on the third floor in a 2-bedroom, 2-bathroom condo with 1,038 SF of living space overlooking your own resort-private snorkel & swim beach (Chang's & Turtle Town). You simply cannot get closer, or have better access, to private amazing beaches in Maui without staying on a boat.
ValueOutdoor spacesPool

King Bed + Pools | Steps to Kamaole Beach
Wake up to ocean breezes and unwind with Maui sunsets from your private top-floor lanai. Just steps from Kamaole Beach Park II, this beautifully remodeled retreat features peekaboo ocean views, a plush king bed, resort-style pools and hot tubs, complimentary beach gear, and a prime South Kihei location within walking distance of beaches, dining, and shopping.
Outdoor spacesLocationKitchen

Last Minute Deal! Oceanview! 2 Bed 2 Bath LOFT!
Centrally located in the heart of South Kihei, this stunning fourth floor 818 square foot 'loft style' condo with spiral staircase boasts a gorgeous ocean view from the lanai and a very spacious floor plan! The resort like amenities are the one of the finest in all of Kihei!
Outdoor spacesValueBeach
Popular amenities for Wailea kayak rentals
House rentals with a kayak

Aloha Aku Bamboo2 Suite – A Serene Sea Retreat
LocationAmenitiesBeach

Aloha Aku CoCoPalm2 Suite – Cozy Beachfront Escape
LocationAmenitiesBeach

Maui Sunset Resort A102 - Aloha Mai, Remodel, Grou
ValueLocationAccess

Aloha Aku Hula2 Suite – Beachfront Bliss
Outdoor spacesLocationHot tub

Maui Sunset A102 - Aloha Mai 2, Beachfront Resort
Outdoor spacesLocationBathroom

Makena Surf B305 Beachfront Resort

Aloha Aku Honu2 Suite – Relax by the Sea in Tranqu
Outdoor spacesLocationGetting around

Aloha Aku Honu Suite – Experience the Spirit of Al
LocationOutdoor spacesView
Other vacation rentals with a kayak

WBH D116 Aloha Wai – Garden Suite Steps from ocean
Outdoor spacesValueAmenities

WBH D227 Aloha Lai – Breathtaking Ocean Views
LocationValueGrill

Ocean Views of Molokini - Makena Surf F304
LocationNearbyBeach

Maui Sunset B102 - Aloha Tai 2, Beachfront Resort
Outdoor spacesLocationAmenities

2 Bedrooms, Get Away in Paradise Kihei, Hawaii

Top Floor Oceanfront great snorkeling (MKM809)
LocationViewAir conditioning

WBH D227 Aloha Lai2 – Unwind by the Oceanfront
ValueLocationQuiet

Beachfront Condo – Hear the Waves Crash
Destinations to explore
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- Kamaole Beach Park II
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