Holiday rentals with a kayak in Kaanapali

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.

5 out of 5 average rating, 39 reviews

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

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.

4.98 out of 5 average rating, 137 reviews

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 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, 127 reviews

Maui Beachfront Oceanfront Sands of Kahana withA/C

Mar 4 - 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.

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, 54 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.

4.91 out of 5 average rating, 23 reviews

A private lanai extends from the condo, featuring outdoor seating with sleek, modern furniture. The ocean view is unobstructed, framed by swaying palm trees. The sandy beach, visible below, meets clear blue waters leading to distant islands under a bright sky.

Condo in Wailea

Makena Surf: Maui on the Beach

Welcome to Unit 303 in Building G at the Makena Surf Resort! NEW LISTING due to new ownership (Jan 24). The new owners have invested a great amount of money into replacing outdated linens and fixtures with high end items not reflected in photos. You will be staying on the third floor in a 2-bedroom, 2-bathroom condo with 1,038 SF of living space overlooking an incredible hidden snorkel & swim beach (Chang's). You simply cannot get closer, or have better access, to better beaches in Maui.

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

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.

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, 165 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.

4.96 out of 5 average rating, 210 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!

5 out of 5 average rating, 12 reviews

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.

Condo in Kaanapali

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.

A covered outdoor dining area features a glass-top table surrounded by six cushioned chairs, overlooking the ocean. Bright blue plates and a vase with an orchid are set on the table, with expansive sea and sky views visible through large sliding doors.

5 out of 5 average rating, 132 reviews

Panoramic Views right on a Sandy Swimmable Beach

Spacious 4th-floor corner condo on a sandy swimmable beach! Air conditioning in every room, 2 lanais (one off of each room), and stunning ocean views—ideal for turtle watching, whale watching (December - April) and sunsets. Family-ready with 4 chairs, beach gear, boogie boards, towels and cooler. Resort offers pools (including kiddie pool), pickleball, tennis, game room and more. Hotel Zoned and cancel for any reason insurance offered after signing contract.

4.84 out of 5 average rating, 161 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.

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.

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, 91 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 pristine swimming pool glimmers under the sun, surrounded by palm trees and lounge chairs. The spacious pool area is bordered by a well-maintained grassy lawn and faces a multi-story condominium complex in the background.

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, 17 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

A covered lanai offers a dining table with four patterned chairs, accompanied by a lounge chair. A decorative arrangement featuring a pineapple and tropical flowers is positioned on the table. Lush gardens and colorful flowers are visible in the background, with palm trees framing the scene.

4.98 out of 5 average rating, 48 reviews

WBH D116 Aloha Wai – Garden Suite Steps from ocean

5 out of 5 average rating, 4 reviews

Honua Kai Konea 513 | FREE CAR | KBM Resorts

4.89 out of 5 average rating, 19 reviews

A spacious lanai features a dining table surrounded by black woven chairs, providing an inviting space for meals outdoors. The view showcases landscaped gardens, palm trees, and the ocean beyond, with clear blue skies enhancing the scene.

Condo in Kaanapali

Hokulani 306 at Honua Kai ~ Upgraded & Ocean Views

5 out of 5 average rating, 4 reviews

Honua Kai Hokulani 318 | FREE CAR | KBM Resorts

5 out of 5 average rating, 3 reviews

Honua Kai Konea 108 | FREE CAR | KBM Resorts

A spacious living area is showcased with soft beige walls and tile flooring. Modern furnishings include a light-colored wooden coffee table adorned with a pink flower arrangement. A wall-mounted flat-screen TV and a dining space with a wooden table are visible, along with a full kitchen area in the background.

4.86 out of 5 average rating, 36 reviews

Maui Sunset B102 - Aloha Tai 2, Beachfront Resort

An outdoor dining area is set on a spacious lanai, featuring a table adorned with a vase of flowers, tableware, and glassware. Scenic mountain views are visible in the background, surrounded by lush greenery and a clear blue sky.

5 out of 5 average rating, 6 reviews

Honua Kai Hokulani 524 | FREE CAR KBM Resorts

A lush green golf course stretches into the distance, bordered by neatly trimmed hedges. Palm trees sway gently in the breeze, while the serene blue ocean is visible beyond the greenery beneath a clear blue sky.