Holiday rentals with a kayak 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.

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.

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.

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.

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.

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.

Papakea K303 ~Highly Upgraded w/ Ocean Views

Looking for a dreamy Maui vacation with stunning ocean views? Look no further than Papakea K303 - a highly upgraded 2 bedroom condo that has everything you need and more! Located in the K building, only one building back from the ocean, this third-floor unit offers breathtaking 180-degree views of the sea and the mountains. With easy access to parking and only a short walk to the heated pool and beach, Papakea K303 is the perfect home base for your Maui vacation.

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.

Maui Banyan Top-Floor Ocean View Sanctuary

This exquisitely remodeled top-floor sanctuary is located in the highly coveted Maui Banyan, offering the perfect blend of luxury and island charm. 🌴✨ Enjoy stunning sunsets and peekaboo ocean views from your private lanai, then stroll across the street to some of South Maui’s finest beaches. Makana Condo has been completely renovated from top to bottom, serving as your ultimate Hawaiian oasis for relaxation or adventure! 🌊☀️

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.

Last Minute Deal! Oceanview! 2 Bed 2 Bath LOFT!

Centrally located in the heart of South Kihei, this stunning fourth floor 818 square foot 'loft style' condo with spiral staircase boasts a gorgeous ocean view from the lanai and a very spacious floor plan! The resort like amenities are the one of the finest in all of Kihei!

Great Location-Wailea Grand Champion#142

Enjoy tranquil golf course views from this spacious condo, featuring a king bed in the master bedroom and a convenient sofa bed in the living room. With two full bathrooms and air conditioning throughout the living area and bedroom, comfort is guaranteed for your stay.