Holiday rentals with a kayak in Napili-Honokowai

5 out of 5 average rating, 6 reviews

A spacious king bed is framed by light blue walls, with decorative accents above the headboard. Large glass doors open to a private lanai offering views of palm trees and the beach. Two bedside lamps provide soft lighting, enhancing the serene atmosphere.

Apartment in Wailea

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 spacesLocationBeach

A patio area features a light-colored chair and a round table, overlooking a grassy lawn that leads to the ocean. A tree with twisted branches is visible in the background, along with several upright, leafy plants. The inviting blue water of a pool can be seen beneath the sunlit sky.

4.9 out of 5 average rating, 21 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.

Outdoor spacesLocationCondition

Top Guest favourite

Apartment in Kaanapali

5 out of 5 average rating, 20 reviews

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

Outdoor spacesLocationView

A round glass-topped dining table is set on a private lanai, accompanied by comfortable wicker chairs. A bottle of wine and glasses are artfully arranged on a wooden tray, with sweeping ocean views extending towards distant islands under a bright sky.

4.95 out of 5 average rating, 135 reviews

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.

LocationOutdoor spacesBeach

4.89 out of 5 average rating, 183 reviews

Check In, Chill Out - Annie’s Surf Shack Awaits!

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.

ValueLocationAmenities

A spacious single-story home is surrounded by lush palm trees and vibrant tropical plants. The well-maintained lawn features a mix of greenery, with the house's exterior displaying a neutral tone under a bright blue sky.

4.86 out of 5 average rating, 169 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.

Outdoor spacesValueTV

An outdoor dining area is displayed on a balcony, showcasing a table set for four. The picturesque beach and calm ocean waters extend in the background under a partly cloudy sky, enhancing the inviting atmosphere for al fresco dining.

4.95 out of 5 average rating, 110 reviews

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.

Outdoor spacesLocationCleanliness

4.94 out of 5 average rating, 16 reviews

Condo in 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.

LocationOutdoor spacesHospitality

A spacious lanai offers stunning ocean views, framed by lush greenery and the nearby resort. A dining table with plates is set up, inviting relaxation and enjoyment of the scenery. The clear blue sky and calm ocean enhance the tranquil atmosphere.

5 out of 5 average rating, 17 reviews

Hokulani 712 at Honua Kai ~Ocean View XL-1 Bedroom

Welcome to your dream Maui vacation rental condo! Hokulani 712 at Honua Kai Resort offers the perfect retreat for those seeking a relaxing and luxurious getaway. This oversized one-bedroom condo sleeps 2 adults and boasts gorgeous ocean views from the large lanai! Located on the top floor (7th floor) of the south side of the Hokulani tower, this unit features a large 235 sq ft lanai with spectacular views of the ocean and the island of Lana'i in the background.

LocationOutdoor spacesCheckout

4.95 out of 5 average rating, 153 reviews

Condo in Kihei

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 spacesValueIndoor spaces

A sweeping view of the coastline showcases gently curved sandy beach bordered by lush palms. The turquoise water sparkles under a bright blue sky, while distant mountains are visible along the horizon, creating a serene oceanfront scene.

4.95 out of 5 average rating, 131 reviews

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.

LocationOutdoor spacesDecor

Top Guest favourite

Condo in Kihei

4.96 out of 5 average rating, 227 reviews

King Bed + Pools | Steps to Kamaole Beach

Wake up to ocean breezes and unwind with Maui sunsets from your private lanai. This beautifully remodeled top-floor condo sits directly across from Kamaole Beach Park II and offers peekaboo ocean views, resort pools and hot tubs, a king bed, beach gear, and easy walking access to South Kihei's best restaurants, shops, and island adventures. Perfect for couples and small families seeking the ideal Maui getaway.

ValueLocationHot tub

Popular amenities for Napili-Honokowai kayak rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with a Kayak

A serene outdoor area includes smooth stone dipping pools and a Jacuzzi with sunset views. Tropical plants are situated in decorative pots, complementing the landscape. The setting is enhanced by tiki torches, and a lush lawn extends towards the horizon under a soft evening sky.

5 out of 5 average rating, 4 reviews

Aloha Aku CoCoPalm Suite – Experience Tropical Bli

LocationHot tubBreakfast

A spacious sleeping area features a canopy bed adorned with soft bedding, complemented by a tasteful patterned cover. A television is positioned on a low console cabinet opposite the bed, while a closet with hangers is visible in the background. The room is painted in a light blue hue.

Private room in Wailuku

4.57 out of 5 average rating, 7 reviews

Serene Blue Retreat•Queen Bed•Smart TV•MiniFridge

LocationSleep qualityHospitality

A serene view features two carved wooden tiki figures positioned amidst a lush green lawn, leading towards a sparkling blue ocean in the background. Delicate orange flowers are visible in the foreground, adding a touch of color to the tranquil landscape.

5 out of 5 average rating, 18 reviews

Aloha Aku CoCoPalm2 Suite – Cozy Beachfront Escape

LocationHot tubAccuracy

An open-concept kitchen and living area features a counter with seating for four, complemented by a wooden dining table for four. Sunlight floods through large sliding glass doors, illuminating stylish furnishings and a lush green lawn visible through the patio area.

4.91 out of 5 average rating, 93 reviews

Maui Sunset Resort A102 - Aloha Mai, Remodel, Grou

ValueLocationLaundry

The beachfront estate is presented from a distance, showcasing its two-level structure surrounded by lush greenery. Large glass doors reveal the inviting spaces within, while a spacious lawn leads to the sandy beach. Solar panels are visible on the roof, emphasizing sustainability.

5 out of 5 average rating, 7 reviews

Aloha Aku Hula2 Suite – Beachfront Bliss

LocationOutdoor spacesFamily

A spacious living area features a light green color palette and vaulted ceilings. Comfortable seating options include a sofa and two armchairs. The open kitchen, equipped with wooden cabinets and appliances, is visible in the background. Large windows provide views of the surrounding greenery.

5 out of 5 average rating, 5 reviews

Aloha Aku Ohana2 Suite – Relaxing Garden Views Awa

LocationAccuracyBeach

A spacious living area showcases elegant tile flooring and large sliding glass doors that invite natural light. A comfortable sofa is paired with a glass coffee table, while a flat-screen TV is mounted on the wall. A private outdoor space is visible through the doors.

4.79 out of 5 average rating, 14 reviews

Maui Sunset A102 - Aloha Mai 2, Beachfront Resort

Outdoor spacesLocationHospitality

A peaceful outdoor water feature is surrounded by lush palm plants in decorative pots. Water flows gently from stone elements into a serene pool, with a backdrop of green grass and distant mountains. The setting evokes a sense of tranquility and connection with nature.

4.93 out of 5 average rating, 28 reviews

Aloha Aku Honu Suite – Experience the Spirit of Al

LocationOutdoor spacesQuiet

Other holiday rentals with a kayak

4.63 out of 5 average rating, 8 reviews

Papakea K303 ~Highly Upgraded w/ Ocean Views

LocationWalkabilityParking

Condo in Wailea

4.7 out of 5 average rating, 50 reviews

2BR Oceanfront | Pool | Gym | High-Speed WiFi

Outdoor spacesValueCondition

A private lanai is displayed, featuring a round dining table and two chairs. Lush greenery and palm trees frame the view of the ocean, with sun loungers visible along the beach. The sky is partly cloudy, creating a serene atmosphere.

5 out of 5 average rating, 7 reviews

Whaler 420: Upgraded 1 Bed/1 Bath With Ocean Views

LocationBeachSleep quality

A private lanai is showcased, featuring a dining set with a table and four chairs, overlooking the lush greenery and ocean. Palm trees sway gently in the breeze, and the vibrant blue water stretches out to the horizon, offering scenic views of the island of Lana'i.

4.95 out of 5 average rating, 20 reviews

The Whaler Resort 359 ~ Upgraded With Ocean Views

LocationOutdoor spacesKitchen

The private lanai offers ocean views framed by palm trees, with comfortable outdoor seating. A round table is accompanied by two chairs, creating a serene spot to enjoy the scenery. The grassy area below leads to the beach access.

5 out of 5 average rating, 16 reviews

Kaanapali Shores 259~Ocean Views & Hear the Waves

LocationHospitalityIndoor spaces

Apartment in Wailea

4.69 out of 5 average rating, 13 reviews

Paradise at its Best KS5310

Outdoor spacesLocationAmenities

A spacious patio area features comfortable outdoor seating with bright cushions, offering a view of lush tropical greenery. Sliding glass doors provide seamless access to the inviting bedroom within, enhancing the indoor-outdoor living experience.

4.88 out of 5 average rating, 34 reviews

Maui Eldorado B206 ~ Big Corner Unit & Large Lanai

ValueLocationBeach