
Beachfront vacation rentals in Wailea
Find and book unique beachfront homes on Airbnb
Top-rated beachfront rentals in Wailea
Guests agree: these beachfront homes are highly rated for location, cleanliness, and more.

Stunning Ocean Views - Winter Specials
*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

Beauty & the Beach: Remodel+Ocean Vws! A+ Location
Welcome to Beauty & the Beach ~ Now Open Dec-March: Whales! Beauty & the Beach is hosted by Tracy O’Reilly, a licensed realtor with Airbnb since 2009, earning SUPERHOST status 40+ consecutive times with a proven track record of 1000s of 5-star reviews. OCEAN VIEW, Remodeled, A+ Location, Steps2Beach, Cold AC, directly next door to food truck oasis, Heated Pool w/BBQ Grills!! ~ If your dates aren't available or if you’re traveling with a group, contact Tracy on Airbnb as she manages 16 units

Ocean view and beach by Wailea
Infants and children welcome! Ocean views, beach across the street. Large lanai. Indoor and outdoor dining. Large bedroom, king bed, ensuite, east facing second lanai off bedroom. Guest bathroom living room. Double height single air mattress, pac n play, high chair. Comfortable and quiet split system A/C. Toys, beach wagon, umbrellas, beach chairs, boogie boards, beach towels provided. Close to shops and restaurants. Tennis courts and two pools in complex. Reserved parking by front door.

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

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.

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.

Stunning Ocean Views
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.

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 have maple cabinets and elegant granite counter tops. There is a comfortable king size bed, a well-stocked kitchen, central AC, with all new bamboo floors throughout, and a new washer / dryer. The Condo is owned and maintained by Maui residents.

Maui Kamaole Retreat Modern Remodel, Close 2 Beach
Aloha and welcome to your Maui escape! 🌺 This newly remodeled coastal-modern condo in Kihei is just a short walk to world-class beaches. Enjoy upgraded interiors with marble counters, walk-in showers, LED mirrors, SMART TVs, and A/C in every room. Step onto the lanai to take in lush garden views—perfect for morning coffee or sunset cocktails. The resort features two pools, hot tubs, tennis courts, and BBQ grills. Whether you're relaxing or exploring, your Maui getaway starts here!

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.

Oceanfront Getaway, Brand New, Steps To Beach
Enjoy the panoramic ocean view directly from the living room. This wonderful ground floor unit offers privacy and tranquility with expansive ocean views, where you can enjoy seasonal whale watching, paddle boarding, surfing, snorkeling as well as many other activities just outside your door. The unit is also adjacent to one of the longest beaches on Maui, Sugar Beach. And just down the road you will find great shopping, restaurants, nightlife and the Maui Ocean Center.
Popular amenities for Wailea beachfront rentals
Pet-friendly beachfront home rentals

Amazing Oceanfront Apartment

Beautiful Views~

Maui Beach House

Maui Westin Kaanapali Ocean Resort Studio

Entire Villa at Nanea Ocean Villas, Maui

A jewel on Oceanfront & Breath Taking Views.

Breathtaking Location-Sugar Beach #129

Walk to Front St., ALOHA CABANA, "PEOPLES CHOICE"
Beachfront home rentals with a pool

Oceanfront Bliss Pool & Stunning Views Hono Kai C3

Chic Maui Condo Steps From Beach & Ocean

Wailea Elua 1101 - Beachfront Section - Ocean View

Wailea Ekahi Gem! | 2 Beds | Steps to Beach & Pool

Gorgeous Condo in Wailea Ekahi Village!

Incomparable Maui Sunset condo, includes all taxes

Maui Retreat Ekahi 50F -All YOU Need!

Mana Kai Palms Beachfront Resort ~Keawakapu Beach
Private beachfront home rentals

Oceanfront Maui Ohana: Best Beach & Wow Sunsets

Direct Oceanfront w/Amazing Views, AC, upgraded!

Epic View! Lovely 2BR Beach Condo in Kihei/Wailea

Maui Oceanfront Condo, Amazing Views, on Sandy Bea

Charley's Hideaway (Oceanfront)

Beachfront Penthouse #25 at Sugar Beach Resort

Mana Kai Resort, Luxury 2bd/2bath Beachfront # 511

Premier Poolside Villa at Kihei Bay Vista (D202)
When is the best time to visit Wailea?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$81,372 GYD | G$83,673 GYD | G$81,791 GYD | G$75,097 GYD | G$63,801 GYD | G$70,076 GYD | G$65,265 GYD | G$67,566 GYD | G$65,683 GYD | G$62,755 GYD | G$69,867 GYD | G$79,280 GYD |
| 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 beachfront rentals in Wailea

Total vacation rentals
Explore 230 vacation rentals in Wailea

Nightly prices starting at
Wailea vacation rentals start at G$25,102 GYD per night before taxes and fees

Verified guest reviews
Over 7,760 verified reviews to help you choose

Family-friendly vacation rentals
140 properties offer extra space & kid-friendly amenities

Vacation rentals with a pool
230 properties feature pools

Rentals with dedicated workspaces
170 properties have a dedicated workspace

Wi-Fi availability
230 of Wailea vacation rentals include wi-fi 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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