Waterfront vacation rentals in Wailea, Wailea-Makena

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Top-rated waterfront rentals in Wailea, Wailea-Makena

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Guest favorite

Condo in Kihei

4.95 out of 5 average rating, 129 reviews

Modern Condo. 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.

Oct 13 – 20

$270 per night

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

Mar 1 – 8

$260 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 :)

Sep 17 – 24

$275 per night

Guest favorite

Condo in Kihei

5.0 out of 5 average rating, 136 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.

Oct 29 – Nov 5

$345 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.

Sep 7 – 12

$198 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.

Dec 13 – 20

$513 per night

Guest favorite

Condo in Kihei

4.99 out of 5 average rating, 143 reviews

Mana Kai 608: Oceanfront Remod- Modern Surf Vibe!

Mana Kai 608 is a remodeled oceanfront 2b/2b 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 vibe 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

$695 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.

Sep 10 – 17

$440 per night

Guest favorite

Condo in Kihei

4.96 out of 5 average rating, 165 reviews

A-Z new, Ocean View, 3 mins walk to beach, 3D tour

You've found it! This beautifully renovated 750 sqft 2bd/2ba is your home away from home! This 3rd floor ocean view unit is in the most perfect location - short walking distance to world famous beaches like Charley Young, Cove Park (great for surfing), and Kamaole beaches, grocery stores, amazing restaurants, shopping & night life! Shopping at the Wailea Mall and world class golfing only 2 miles away. The complex also features a swimming pool, hot tub and BBQ grills.

Sep 27 – Oct 4

$393 per night

Guest favorite

Condo in Kihei

4.95 out of 5 average rating, 141 reviews

Minimalist + Newly Renovated Beach Paradise

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

$292 per night

Guest favorite

Condo in Wailuku

4.94 out of 5 average rating, 163 reviews

Rare Beachfront Ground floor Oceanview from Lanai!

Enjoy a Romantic yet affordable Direct BeachFront, Ground floor condo with a partial ocean view from the Lanai. NOT ACROSS THE STREET FROM THE OCEAN! Located on gorgeous Sugar Beach, Maalaea- the LONGEST WALKING BEACH on the entire island. Humpback Whales (Nov-April) and turtles are often seen in the waters. On a a quiet, non-through road, this is like your own little neighborhood paradise! GE-210-827-7760-01 TA-210-827-7760-01 General Excise/Transient Tax

Sep 19 – 26

$189 per night

Guest favorite

Condo in Kihei

4.93 out of 5 average rating, 218 reviews

Hale Kai O Kihei 307 | Direct Beachfront

Hawaii Life Vacations presents a new addition to "The Hotel Collection". This fully remodeled top-floor suite boasts sweeping ocean views. Enjoy watching the waves lapping the golden sandy beach from your balcony. Light, bright, and well appointed, 307 @ HKOK offers A/C in the living room, fully equipped kitchen w/amenities, and on-site pool and lounge area for your enjoyment. GE/TA# - W-13763254-01

Mar 1 – 8

$383 per night