
Waterfront holiday rentals in Wailea
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Top-rated waterfront rentals in Wailea
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Stunning Ocean Views -November Specials $157
*PLEASE NOTE A 14.8% HAWAII STATE TA/GE TAX WILL BE ADDED AND COLLECTED BY THE END OF YOUR STAY** COMPLETELY REMODELED THIS SUMMER IN A COMFORTABLE MODERN-TROPICAL STYLE. THE HIGHEST THREAD- COUNT LINENS AND TEAK THROUGHOUT THIS HIGH STYLED CONDO. HUGE VIEWS FROM THE MODERN KITCHEN, LIVING ROOM AND LANAI All SET IN THE HEART OF KIHEI. FABULOUS LOADS OF BEACH GEAR SURFING LESSONS DOWNSTAIRS BIKE RENTALS DOWNSTAIRS PARKS AND BEACHES ACROSS THE STREET 2 BLOCKS FROM SOME OF KIHEI'S FINEST RESTAURANT

Mana Kai 608: Oceanfront Remod! Modern Surf Vibe
Mana Kai 608 is a remodeled oceanfront condo DIRECTLY on Keawakapu beach! Mana Kai is a hotel zoned resort in the ideal location, right on the border of Wailea and Kihei! Our condo is designed 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, stay with us! We have the best Property Mgr. in Maui, Tracy O'Reilly to take amazing care of you!

Oceanfront Mana Kai Penthouse..Heaven meets Earth!
Aloha and E Komo Mai! (Welcome) Where Heaven meets Earth! Immerse yourself in the best location and bi-coastal oceanfront views to spend your luxury vacation experience in South Maui. This Mana Kai penthouse is on the 8th floor (806) and includes two-bedroom suites on the world-famous Keawakapu Beach. Located on the longest sandy beach in Wailea (2.75 miles), you will enjoy excellent snorkeling, body surfing, whale watching, scuba diving, paddle boarding, and kayaking literally at your doorstep

Spacious S. Kihei Suite New A/C across from Kam 3
This spacious suite is perfect a relaxing stay for two. Brand new split system A/C in bedroom & living room to keep you cool. Peak-a-boo ocean views from the suite with glimpses of Kahoolawe. Located in S. Kihei across from one of the BEST beaches on Maui, Kamaole Beach III and steps from the Kihei Boat Ramp. Walk to shops and restaurants in South Kihei. Keawakapu Beach and Wailea is just minutes away. Choose from 2 pools or play a round of tennis or pickle ball. Large lawns and BBQ areas.

Beachfront Oceanview Wailea Ekahi 16B Studio W/AC
Wailea Ekahi is a luxurious resort fronting onto beautiful Keawakapu Beach with acres of tropical grounds and 4 pools. Unit 16B is a mid property, renovated ground floor ocean view studio unit (500 sq feet) with a King sized bed, walk in shower and full kitchen. Enjoy your morning coffee and meals from the peaceful, shaded lanai which opens onto the lush greenspace and gardens while enjoying ocean views. A short walk to the beach, pools, luxury shopping, highend dining and golf courses.

Wailea Getaway - 2BD - steps to great pool & beach
Aloha, if you are looking for the perfect place to call home in Maui, you just found it! Our Wailea Ekahi Villa is a spacious and private home away from home that makes you feel far from it all yet is still close to everything! Situated above what is widely considered one of the most beautiful beaches in all of Maui Wailea Ekahi is like your own private oasis w/ 35 acres of open grassy spaces, private walk paths and the most AMAZING oceanfront pool to relax in and melt all your worries away!

Full Ocean- Full Sunsets- Beaches at Royal Mauiian
Hawaii License: T-174-283-2640 Full ocean & beach front - all year sunsets. Royal Mauiian - Highly sought location in S. Kihei. Nicely done 1 BR - 1 BTH Nicely furnished, very streamlined open feel. Walk to restaurants, steps to Kam 1 beach, close to shops & activities. Rent a paddleboard, buy Hawaiian memorabilia, or shop at Harvest Moons - close by. Split Air in Bedroom & Living Area. Fully equipped kitchen. In Unit Laundry GET & TAT tax total of 17.75% included in final price.

Modern & Polished Oceanfront Vistas
Bright, modern, and spacious. Complete remodel in December 2021! Thoughtfully designed to elevate your experience with us. This one-bedroom, one-bathroom condo features luxurious touches throughout paired with beautiful ocean views. Located in the sunny and vibrant beach town of Kihei, all of Maui is within reach. Beach chairs, umbrellas, luxury beach towels and a cooler are all provided to enjoy a day at the beach! We strive to achieve a warm, welcoming, and thoughtful retreat here on Maui.

Renovated Condo | 3 Min Walk to Toes in the Sand!
Welcome to Pacific Pearl — your serene Maui escape just steps from golden-sand Kamaole Beach Park II. Set in the lush, resort-style Maui Banyan complex, this fully remodeled ground-floor condo offers peaceful garden views, a walkable location near dining and shops, and all the comforts of home. Spend your mornings snorkeling, your afternoons lounging by the pool, and your evenings with sunset walks on the shore. Perfect for couples, families, or friends seeking the effortless Maui getaway.

Stunning Ocean Views · Steps to Beach · Comfort
Welcome to our slice of paradise in Maui and enjoy breathtaking 180° ocean views . Located just steps from the sandy Kamaole 1 Beach and a short stroll from vibrant restaurants and bars, our chic coastal-modern condo is the perfect spot for a beach getaway. Condo features all the amenities you need for a comfortable stay, including A/C in all rooms, a luxurious king bed, high-speed internet, fully equipped kitchen and a private lanai to watch sunsets. Your Maui adventure starts here

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.

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.
Popular amenities for waterfront rentals in Wailea
Waterfront apartment rentals

Stunning Luxury Oceanview Condo

Beautiful Studio Oasis Maui Banyan

Oceanfront Ground Floor w/Stunning Sunset Views

100 steps from the beach! Tranquil Seaside Oasis

Sugar Beach Resort #532 - Maui HI

Next to Beach, Foods & Shops - Updated w/ View!

Charley's Hideaway (Oceanfront)

Oceanfront penthouse with amazing views at Kauhale
Waterfront house rentals

Island-Inspired 2BD Oceanfront ~ Quam Properties

Hale Hookipa Kai House, County Licensed

Gorgeous Views! - Kihei Surfside #109

Beautiful Beachfront Townhouse !

Oceanfront Napili Shores ~AC

Centrally located and steps to the beach!

Maalaea Kai 307 - Maui Prime Oceanfront

Westin Ka'anapali Ocean Resort Villas North- 2bd
Waterfront apartment rentals

Fully remodeled, Ocean View, 3 mins walk to beach

*25% Off-Steps to Beach-AC in Every Room-Remodeled

Turtle Cove Oceanfront Views Island Sands Resort

Makani A Kai B4 beachfront Maui, pool, a/c, w/d

Gorgeous Condo in Wailea Ekahi Village!

Incomparable Maui Sunset condo, includes all taxes

Stunning Ocean View Penthouse - Steps to Beach

Top Floor Ocean Views | Beach & Restaurant Access
When is the best time to visit Wailea?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £297 | £304 | £296 | £269 | £226 | £253 | £228 | £216 | £218 | £209 | £245 | £282 |
| Avg. temp | 16°C | 16°C | 16°C | 17°C | 18°C | 18°C | 19°C | 20°C | 19°C | 19°C | 18°C | 17°C |
Quick stats about waterfront rentals in Wailea

Total holiday rentals
Explore 290 holiday rentals in Wailea

Nightly prices starting at
Wailea holiday rentals start at £68 per night before taxes and fees

Verified guest reviews
Over 6,020 verified reviews to help you choose

Family-friendly holiday rentals
190 properties offer extra space & child-friendly amenities

Holiday rentals with a pool
280 properties feature pools

Rentals with dedicated workspaces
200 properties have a dedicated workspace

Wifi availability
290 of Wailea holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Wailea rentals

4.8 Average rating
Wailea stays are highly rated by guests – averaging 4.8 out of 5!
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- Maui
- Kaanapali Beach
- Kahului Beach
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- Laie
- Honolua Bay
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- Spreckelsville Beach
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- Olowalu Beach
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