Condo vacation rentals in Wailea, Wailea-Makena

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Top-rated condo rentals in Wailea, Wailea-Makena

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Guest favourite

Condo in Kihei

4.91 out of 5 average rating, 136 reviews

160KReno-Stunning Palms in Wailea Condo-Beach/Golf

Brand New 160K Renovation+Redecoration for a Hawaiian Beach Vibe.Wailea is one of the most sought after resort addresses on Maui.Here you can relax in the luxury of the beautiful grounds+refreshing swimming pool+spa.World Class Golf+Shopping.Ground floor condo with private lanai that overlooks the grass.King Master Bed with a private bath,2 Uber deluxe pull out Queen bed couches.Short stroll to Keawakapu Beach from condo where you can snorkel/take long tropical beach walk.BOOKINGS UP TO 365 DAY

Apr. 7 – 14

$592 CAD per night

Guest favourite

Condo in Kihei

4.95 out of 5 average rating, 130 reviews

Renovated! Just 3 Min Walk to Toes in the Sand

Welcome to Pacific Pearl, nestled in South Coastal Kihei Maui. Positioned directly opposite the renowned Kamaole Beach Park II, this condominium offers easy access to restaurants and shops, and is just a short drive from Wailea. It's an ideal spot for spending quality time with family and friends. Dive into a plethora of activities including swimming, snorkeling, paddle boarding, sailing, fishing, golfing, scuba diving, and immersing yourself in the natural splendor of Maui's tropical landscape.

Sep. 2 – 9

$456 CAD per night

Guest favourite

Condo in Kihei

4.96 out of 5 average rating, 112 reviews

Spacious Unit in Aston Maui Hill w/ Netflix&more

Welcome to Aston Maui Hill Resort in the heart of Kihei right next to Wailea. We offer you the entire place with kitchen ,two bathrooms, one bedroom ,a living room with a queen bed. Again this is not a shared place anymore. You’ll have the entire place Its a real garden style resort close to beaches and restaurants. We started as a shared unit however we are renting it out the entire place now that we are retiring and traveling. We always value our guests recommendations to improved. Mahalo

Oct. 22 – 29

$458 CAD per night

Guest favourite

Condo in Wailea-Makena

4.95 out of 5 average rating, 172 reviews

A.R.A Retreats: The Waterfall

Nicknamed “The Waterfall” for its massive 105 inch by 65 inch peninsula with it large waterfall countertop, perfect for cooking and entertaining. This was the first time we had done this Waterfall feature in our unit. Located in Grand Champions Villas in Wailea. Guests can enjoy the spacious NEW condo that has everything you should need for your trip! Guests can enjoy the spacious and comfortable condo that has everything you should need for your trip--including smart TV's in each room :)

Sep. 13 – 20

$898 CAD per night

Guest favourite

Condo in Kihei

5.0 out of 5 average rating, 137 reviews

Sugar Beach Resort Beach / Ocean Front Unit 426

SPECTACULAR OCEAN AND SUNSET VIEWS, including outer islands from the living room and lanai. You'll enjoy drinks in the evening watching the incredible sunsets. The condo has been totally redecorated and upgraded. The kitchen and bathroom are newly remodeled with maple cabinets and elegant granite counter tops. There is a very comfortable king size bed, a well-stocked kitchen, central AC, bamboo floors throughout, and a washer / dryer. The Condo is owned and maintained by Maui residents.

Mar. 20 – 27

$815 CAD per night

Guest favourite

Condo in Kihei

4.94 out of 5 average rating, 198 reviews

Mana Kai Maui - Oceanfront Condo in Kihei

Located on the shores of beautiful Keawakapu Beach lies your next island paradise vacation. The Mana Kai Maui resort straddles the communities of Kihei and Wailea offering the beauty and privacy of Wailea beaches with the value of Kihei. This Maui beachfront condo offers stunning ocean views from a private lanai and is just steps to the beach, with access to a swimming pool, restaurant, general store and beach equipment rental. With 2 bedrooms and 2 baths, it sleeps four people comfortably.

Apr. 1 – 8

$843 CAD per night

Guest favourite

Condo in Kihei

4.99 out of 5 average rating, 133 reviews

Luxury condo • 180° Ocean Views • Steps to Beach

Enjoy panoramic ocean, mountain, beach & sunset views year round at Hale Meli (short for "Hale Mahina Meli" or “Honeymoon House” in Hawaiian), a top floor condo with exquisite designer interiors and high-end amenities. Ideally located in Kihei, the condo is right across the street from one of the best beaches on Maui and is walking distance to restaurants, shops and grocery stores. It is also your perfect home base for exploring the rest of Maui, being centrally located on the island.

Nov. 24 – Dec. 1

$1,588 CAD per night

Guest favourite

Condo in Kihei

4.99 out of 5 average rating, 131 reviews

Maui Dream Place at Maui Kamaole G-209, Ocean View

Maui Dream Place is our vacation home rental property in Maui, Hawaii. This two story condo has plenty of space for your family, plus hotel-style amenities which include access to two swimming pools, hot tubs and tennis courts. In our opinion, our condo has the best views of the sunset in Kihei. Our condo is located at Maui Kamaole, a luscious and vibrant Hawaiian vacation rental community set on a hilltop on the south end of Kihei located only 25 minutes away from Kahului Airport.

Oct. 20 – 27

$829 CAD per night

Guest favourite

Condo in Kihei

4.99 out of 5 average rating, 114 reviews

Romantic, Luxury Maui Getaway with Ocean View

This is a luxury 1 bedroom 2 bathroom condo which has been fully renovated. Our condo has lovely ocean views as well as views of the lush tropical gardens and the pool. It has a fully stocked gourmet kitchen with high end appliances, assorted spices, coffee and tea. Sunset views from the lanai are stunning. If our Wailea Palms condo is not available during the days of your travel, please check availability at our other Wailea Palms condo at https://www.airbnb.com/rooms/1728525

Apr. 1 – 8

$680 CAD per night

Guest favourite

Condo in Kihei

4.99 out of 5 average rating, 147 reviews

Mana Kai 608: Oceanfront Remod- Modern Surf Vibe!

Mana Kai 608 is a remodeled oceanfront condo DIRECTLY on Keawakapu beach! This location is ideal, on the border of Wailea and Kihei. We have designed our remodel with a modern surf feel in mind, we are excited to share it with you! If you enjoy Wailea's 5-star resorts but crave a kitchen, less fees, better views, or don't want to cross the street to get to the beach come stay with us! We have hired the best Property Manager in Maui, Tracy O'Reilly to take care of our guests.

Sep. 2 – 9

$1,326 CAD per night

Guest favourite

Condo in Kihei

4.95 out of 5 average rating, 144 reviews

Newly Renovated Beach Condo

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!

Sep. 8 – 15

$465 CAD per night

Guest favourite

Condo in Wailea

4.93 out of 5 average rating, 145 reviews

Stunning ocean view! 2/2 in the heart of Wailea

Beautiful, spacious, modern 2/2 condo located in the heart of the Wailea Resort area with gorgeous, far-reaching ocean and island views, and surrounded by brilliant, lush, flowery grounds. Super-close to dining, golf, shopping, and only a short stroll to award-winning Wailea and Ulua beaches! Please note that this condo is in the Wailea Resort area, and does not infringe upon nor remove housing from the local neighborhoods of Maui.

Oct. 9 – 16

$865 CAD per night