Vacation rentals with a kayak in Kaanapali

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Top-rated kayak rentals in Kaanapali

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Top guest favorite

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

5 out of 5 average rating, 36 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

Guest favorite

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

4.98 out of 5 average rating, 123 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.

Guest favorite

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.

Condo in Lahaina

4.9 out of 5 average rating, 181 reviews

Fall Flash Sale – $159/Night in Maui!

Welcome to Annie’s Surf Shack Maui, an oceanfront escape just 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, so you can book your stay with confidence. Annie’s Surf Shack remains fully licensed, compliant, and ready to share the aloha. Super clean, ideally located. No check-ins on major holidays.

Guest favorite

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.

Condo in Lahaina

4.98 out of 5 average rating, 120 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

Guest favorite

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 Kihei

4.9 out of 5 average rating, 20 reviews

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.

Guest favorite

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.

Home in Kihei

4.87 out of 5 average rating, 155 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.

Superhost

A lush garden area featuring palm trees and green landscaping can be seen in the foreground, contrasting with the building structures behind. The ocean is visible in the background, with a clear blue sky above, creating a serene atmosphere.

Condo in Kaanapali

4.81 out of 5 average rating, 16 reviews

Light & Bright with Views: Honua Kai Hokulani 414

Welcome to Hokulani 414, you're home away from home at the Honua Kai Resort! This 1 bedroom/1 bathroom condo is bright and airy, with partial ocean views. You are only a short stroll away from some of Maui's most beautiful beaches, swimming pools, Duke's, and 24-hour gym. A dream Maui vacation; 7 pools, a waterslide, hot tubs, barbecues, and more, you have everything you need to relax and unwind in style. Live the good life on your next vacation- by booking with Maui Westside today!

Top guest favorite

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 Kihei

4.96 out of 5 average rating, 201 reviews

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!

Top guest favorite

A spacious outdoor dining area features a glass-top table surrounded by comfortable chairs. The backdrop showcases vibrant palm trees and a sweeping view of the Pacific Ocean, creating a serene and inviting setting for enjoying meals or gatherings.

Condo in Lahaina

5 out of 5 average rating, 37 reviews

Papakea Penthouse K-401 2 Bed 2 Bath with A/C

We invite you to experience one of Papakea's finest top floor, end units K-401. (Fun Fact: Papakea means crest of the wave in Hawaiian) This 2 BD 2 BA penthouse unit underwent a complete renovation in 2022. The Papakea facility fee is $25 per day paid by the guest upon check in and a $50 incidental hold that would be released to their card when you check out. The tax is a 17.97% on your nightly room rate and is something the state of Hawaii requires us to collect.

Superhost

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

4.85 out of 5 average rating, 156 reviews

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.

Guest favorite

A cozy living area features a blue sofa, a glass dining table with blue chairs, and a wooden desk. Large sliding glass doors provide a view of the ocean and lead to the lanai. Tropical artwork complements the decor, creating a relaxed ambiance.

Condo in Lahaina

4.95 out of 5 average rating, 122 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.

Superhost

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.

Condo in Lahaina

4.88 out of 5 average rating, 136 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!