Holiday rentals with a kayak in Kaanapali

5 out of 5 average rating, 39 reviews

A private lanai is seen with outdoor seating for two and a small table, offering stunning ocean views. Lush greenery is visible in the foreground, complemented by the vibrant blue water and distant islands under a partly cloudy sky.

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, 132 reviews

The bedroom features a plank headboard with a spacious bed dressed in soothing seafoam colors. Soft accent pillows adorn the bed, including one that reads 'aloha', while a bedside lamp provides gentle illumination.

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.

A panoramic view of the ocean is presented, showcasing calm turquoise waters meeting a sandy beach. Lush palm trees line the shore, while distant mountains create a striking backdrop under a partly cloudy sky, enhancing the serene coastal landscape.

4.98 out of 5 average rating, 124 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

The resort's pool area is surrounded by lush landscaping and palm trees, featuring a large, winding pool with a rock formation and a waterfall. Numerous lounge chairs are arranged around the pool, inviting relaxation under the clear blue sky.

4.98 out of 5 average rating, 51 reviews

1 Bedroom Scenic view-Hawaii's Ka'anapali Beach Cl

Comfort meets convenience at Ka‘anapali Beach Club, located on Maui’s western shore just minutes from downtown Lahaina. Relax in the pool, set among lush landscape and calming waterfalls, or sip your morning coffee at the on-site open-air café. With an on-site restaurant and convenience store, you’ll have everything you need to make the most of your Maui vacation. Enjoy either ocean or mountain views from your private balcony, and reconnect with your loved ones in the spacious accommodations.

A small table and two chairs are positioned on a balcony overlooking the ocean. The clear blue water stretches to the horizon, with shadows of clouds reflecting on the surface. Lush greenery and palm trees frame the scene.

4.9 out of 5 average rating, 181 reviews

Massive November Flash Sale, Book Now!

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.

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.

4.85 out of 5 average rating, 163 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.

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.

4.96 out of 5 average rating, 126 reviews

Maui Beachfront Oceanfront Sands of Kahana withA/C

🌺 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.

4.96 out of 5 average rating, 207 reviews

A dining table set for four is positioned on the private lanai, surrounded by lush greenery. A bottle of wine sits center stage, accompanied by a plate of fresh fruit and pastries. Bright blue skies provide a serene backdrop.

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!

4.84 out of 5 average rating, 160 reviews

An inviting entrance is framed by lush greenery, featuring a stone pathway that leads to a swimming pool area. Strong wood beams support a structure adorned with lamps, while vibrant palms and decorative rocks enhance the natural ambiance.

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.

An outdoor lanai is furnished with a long dining table and several black chairs, offering ample seating. A comfortable seating area is visible, enhancing the space's relaxation potential. Lush greenery surrounds the area, with a glimpse of the pool and palm trees in the background.

4.93 out of 5 average rating, 15 reviews

Luana 3C:Private Villa w/ BBQ & Lanai at Honua Kai

Experience the ultimate island living at Luana Garden Villa 3C, located in Enclave One at the Honua Kai Resort & Spa. This elegant 2,047 sq ft villa is situated on the upper floor of building 3, and comes with a massive 521 sq ft lanai with a private outdoor kitchen overlooking the Enclave One secluded pool area. Featuring a private garage, plus additional parking for a second vehicle & a free EV charger in the garage.

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, 123 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.

A spacious bedroom features a large bed dressed in a light blue quilt, complemented by decorative pillows. Two bedside lamps illuminate the room, while sliding glass doors provide views of the surrounding lush greenery and mountains. A decorative tray with cups and flowers rests on the bed.

4.88 out of 5 average rating, 138 reviews

Beautiful Views~

Hale Aloha is located in The Maui Kaanapali Villas located on the 5th floor unit 507. Hale Aloha boost beautiful Ocean/Molokai views blended with the West Maui Mountains. Our beach is a true "Hidden Gem" for swimming, snorkeling or relaxing on a sandy beach. Enjoy 2 swimming pools , on site restaurant and close to local shopping and activities. We welcome You!

Popular amenities for Kaanapali kayak rentals

Kitchen

Wi-Fi

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, 3 reviews

Aloha Aku CoCoPalm Suite – Experience Tropical Bli

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

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, 90 reviews

Maui Sunset Resort A102 - Aloha Mai, Remodel, Grou

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

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

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.

4.85 out of 5 average rating, 13 reviews

Maui Sunset A102 - Aloha Mai 2, Beachfront Resort

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.

4.88 out of 5 average rating, 16 reviews

Aloha Aku Honu2 Suite – Relax by the Sea in Tranqu

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, 27 reviews

Aloha Aku Honu Suite – Experience the Spirit of Al

Other holiday rentals with a kayak

4.95 out of 5 average rating, 169 reviews

The living area features a comfortable couch and a dining table with bench seating. Natural light filters through the sliding glass doors, showcasing views of a garden outside. A ceiling fan and decorative elements, including a mirror and potted plant, add to the cozy ambiance.

Condo in Kihei

Renovated 2BD/2BA | 3 Min Walk to Beach | A/C

The resort is featured at twilight, showcasing the illuminated swimming pool in the foreground. Decorative lighting casts a soft glow on the water, surrounded by lush landscaping. The multi-story building in the background highlights numerous balconies and modern architecture.

4.89 out of 5 average rating, 9 reviews

Konea 314~Luxuriously Upgraded Furniture & Floors

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, 5 reviews

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

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, 19 reviews

The Whaler Resort 359 ~ Upgraded With Ocean Views

4.91 out of 5 average rating, 126 reviews

A well-maintained swimming pool is surrounded by lush tropical landscaping, featuring palm trees and colorful plants. A water slide is visible beside the pool, and a stone pathway leads to a gated entrance, enhancing privacy and access.

Campsite in Wailuku

Stall #1 Safe place to sleep in your vehicle

A spacious private lanai is showcased with modern outdoor furniture, including a glass-topped table and several chairs. The stunning ocean view can be seen in the background alongside the resort's greenery, providing a serene backdrop for relaxation.

5 out of 5 average rating, 26 reviews

Hokulani 612 at Honua Ka ~Upgraded with Ocean View

4.88 out of 5 average rating, 92 reviews

A swimming pool is framed by a stone patio and surrounded by lush greenery. A waterslide is positioned beside the pool, and decorative lighting is installed along the perimeter. A gated entrance adds to the privacy of the area.

Place to stay in Wailuku

Stall #3 Safe place to sleep in your vehicle

A spacious lanai features a round dining table set with decorative placemats, coffee mugs, and a bag of coffee. Lush tropical plants and palm trees can be seen in the background, with partial ocean views visible beyond the resort landscape under a clear blue sky.