Holiday rentals with a kayak near Kaanapali Beach

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, 132 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.

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.

Guest favourite

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.

4.9 out of 5 average rating, 21 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 favourite

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.

Superhost

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

4.85 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.

Guest favourite

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.

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.

4.96 out of 5 average rating, 207 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!

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.

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

4.84 out of 5 average rating, 160 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.

Superhost

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.

Condo in Kaanapali

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.