Waterfront vacation rentals in Wailea-Makena

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Top-rated waterfront rentals in Wailea-Makena

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Guest favorite

Condo in Kihei

4.95 out of 5 average rating, 111 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

Sep 14 – 21

ﺩ.ﺇ924 per night

Guest favorite

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

ﺩ.ﺇ1,007 per night

Guest favorite

Condo in Kihei

4.98 out of 5 average rating, 127 reviews

The Pi Life: Ocean Views · 99 Steps from the Beach

Pi (π) is an irrational number. There's no fraction, formula or pattern that represents it. It’s stubborn. And you can say, it kinda likes to do its own thing. At The Pi Life, we want your experience to be the same. There doesn’t need to be a rhyme or reason for your trip or how your time is spent. The plan is for you to “do you,” and let us do everything we can to make it a special experience. ★ Panoramic ocean view ★ Walk to beach + restaurants ★ Resort amenities 100+ 4.99 Star Reviews :)

Oct 2 – 9

ﺩ.ﺇ1,311 per night

Guest favorite

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.

Dec 14 – 21

ﺩ.ﺇ1,794 per night

Guest favorite

Condo in Wailuku. Maui

4.88 out of 5 average rating, 233 reviews

Oceanfront Condo. Pool & Spa, 1 Br.

DIRECT OCEANFRONT. Oceanfront lawn, panoramic views, full kitchen, washer/dryer, granite counters, oceanfront lanai, all supplies, beach gear, quiet... with pool, jacuzzi/spa, BBQ, TempurPedic queen bed, desk, free wi-fi & parking. Nearby uninhabited 5 mile long beach walk & swim, Rooms have fans and windows /screens that allow cooling breezes along with one A/C unit Peaceful Maalaea neighborhood. Centrally located to explore Maui, 15 minutes to airport. Adults(2) only. No smoking.

Aug 21 – 28

ﺩ.ﺇ836 per night

Guest favorite

Condo in Kihei

4.99 out of 5 average rating, 130 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

ﺩ.ﺇ2,114 per night

Guest favorite

Apartment in Kihei

4.94 out of 5 average rating, 106 reviews

Wailea Couples Retreat, 300 FT To Keawakapu Beach

Ekahi Ocean Studio is perfectly located in the lower village of Wailea Ekahi (ground floor), a lush-landscaped paradise, just steps from the oceanfront pool and to world-renowned Keawakapu beach. This studio is perfect for couples seeking a peaceful, romantic retreat. You can spend your days lounging at the beach or oceanfront pool, running along the nearby beachfront pathway, exploring nearby Wailea restaurants and resorts or enjoying our cook's kitchen and your private Lanai.

Dec 6 – 13

ﺩ.ﺇ1,858 per night

Guest favorite

Condo in Kihei

4.99 out of 5 average rating, 146 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

ﺩ.ﺇ2,932 per night

Guest favorite

Condo in Kihei

4.96 out of 5 average rating, 164 reviews

Romantic and Modern Condo by the Beach!

Indulge in island luxury at our stunning condo in South Kihei. Recently remodeled to perfection, this oasis boasts a full kitchen, in-unit laundry, and a private outdoor lanai with breathtaking ocean views. Walk to fabulous shopping, dining, and pristine beaches just minutes from your front door. With 2 pools, 2 spas and lush tropical gardens, you'll enjoy one of the best condos in one of the best resorts in South Maui. BOOK NOW, endless summer awaits you!

Jul 11 – 18

ﺩ.ﺇ862 per night

Guest favorite

Condo in Kihei

4.95 out of 5 average rating, 142 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!

Jul 19 – 26

ﺩ.ﺇ1,269 per night

Guest favorite

Condo in Kihei

4.89 out of 5 average rating, 112 reviews

A little beachy, bohemian slice of paradise

Little Condo on Maui is a vacation rental curated by Little House on Maui. Little House on Maui creates functional art and was featured in the May/June 2021 issue of Modern Luxury Hawai’i for their work. Lauren, the hands behind Little House on Maui, purchased this condo with her husband Matt at the end of April (2021) and quickly they began giving the space a full renovation. This space is a project dear to their hearts and a continuous work of love.

May 10 – 17

ﺩ.ﺇ935 per night

Guest favorite

Condo in Kihei

4.93 out of 5 average rating, 207 reviews

Magnificent remodel with ocean View

South Maui, Kihei. Just a 5 minute walk across the street you will have your toes in the soft white sand at one of the nicest beaches in the world. Just put on your flip flops, S.P.F., grab a hat and chair, breathe in the ocean air, listen to the waves, and the songs of tropical birds, and enjoy breathtaking sunsets every night. Location is everything. You will love to stroll this walking town, for great food, bars, shopping and surf lessons.

Jan 21 – 28

ﺩ.ﺇ1,220 per night