
Waterfront vacation rentals in Wailea
Find and book unique waterfront rentals on Airbnb
Quick stats about waterfront rentals in Wailea

Total vacation rentals
Explore 340 vacation rentals in Wailea

Nightly prices starting at
Wailea vacation rentals start at G$25,120 GYD per night before taxes and fees

Verified guest reviews
Over 6,470 verified reviews to help you choose

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

Vacation rentals with a pool
330 properties feature pools

Rentals with dedicated workspaces
240 properties have a dedicated workspace

Wi-Fi availability
340 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!
Top-rated waterfront rentals in Wailea
Guests agree: these waterfront rentals are highly rated for location, cleanliness, and more.

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.

Coastal Dream Oceanfront Condo!
Take a moment to unwind and appreciate the stunning views from the patio, where you can spot whales from Nov-April and catch a glimpse of surfers riding the "Freight Train" during mid-summer. Venture out for a leisurely walk to Maalaea Harbor Shops and the Maui Ocean Center, or explore with a drive to Lahaina (West), Hana (East), or Wailea (South tip). Enjoy delightful amenities including Heated Pool, Oceanfront BBQ station, and Lounge area on the lawn. Designated parking right out front.

Mana Kai 608- Oceanfront Thanksgiving Now OPEN!
Mana Kai 608 is a remodeled oceanfront condo DIRECTLY ON Keawakapu beach! Mana Kai is a hotel zoned resort in the ideal location, 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 Manager in Maui, Tracy O'Reilly to take amazing care of you!

Oceanfront, Beautiful View, Newly Renovated!
Our Maui vacation home is a beach front condo on the FOURTH floor in Kauhale Makai on the beach side of South Kihei Rd, steps to the beach. Beautiful ocean views from both bedroom and living room and features hotel-style amenities; an adult pool, kiddie pool, large hot tub, putting green, shuffleboard and free parking. Recently remodeled, our condo has central air-conditioning and easy access to all parts of the island! All taxes are included in the price. Ta-163-430-2464-01 (TAT LICENSE)

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 18.5% 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

Ekahi Ocean Studio: Wailea Paradise by the 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.

180° Ocean views • Luxe condo • Steps to Beach
Enjoy panoramic ocean & sunset views year round from, Kihei Lani, a 5th floor luxury condo that artfully blends contemporary design, modern amenities and island style. Full, whisper quiet AC in all rooms! Ideally located in Kihei, the condo is right across the street from the best beaches on Maui and is walking distance to excellent restaurants, shops and grocery stores. It is also your perfect home base for exploring the rest of Maui, being centrally located on the island.

Upscale Oceanfront Penthouse Vistas
Full remodel and decorated ourfitted with all new furnishings. This elegant 2-bedroom, 2-bath condo features luxurious touches paired with oceanfront serenity. Located in sunny Kihei at Menehune Shores resort, all of Maui is within reach. Beach chairs, umbrellas, towels, and a cooler are all provided. We offer a fully stocked kitchen for those who want to cook. Experience the resort's many amenities such as beach access with snorkeling, a private pool, and grills.

Walk to 3 Beaches | Top-Floor Maui Studio
Experience the best of South Kihei from this beautifully remodeled top-floor studio at Maui Banyan. Walk to three beautiful beaches, local restaurants, cafés, and shops, then unwind on your private lanai with peekaboo ocean views and unforgettable Maui sunsets. Complete with a plush king bed, split AC, fast Wi-Fi, complimentary beach gear, free parking, and resort pools, hot tubs, tennis courts, and BBQ areas, it's the perfect retreat for a relaxing Maui getaway.
Popular amenities for Wailea waterfront rentals
Waterfront apartment rentals

Beautiful Studio Oasis Maui Banyan

Ocean Front With Ocean View! AC, King Bed, 2 Bath!

Family Oceanview | Beach, Pool, Hot Tub, AC

Steps to Charley Young Beach • Remodeled• Pool •AC

High-end, On Beach, View Balcony, with Pool & BBQ!

Walk to Charley Young Beach | Bright Kihei Oasis

Charley's Hideaway (Oceanfront)

Remodeled, 40% off, steps from the beach, private
Waterfront house rentals

Stunning One Bd Partial ocean, AC, wifi,Pool C209

Chic Villa 2 | Modern Vibes by the Ocean

Ocean Front Cottage, 30 steps to the beach!

Beautiful Beachfront Townhouse !

Centrally located and steps to the beach!

Maalaea Kai 307 - Maui Prime Oceanfront

Aloha Aku Hula Suite – Find Peace by the Shore

Exclusive Beachfront Cottage, Ocean Views, WiFi/AC
Waterfront condo rentals

Dolphin Penthouse at Milowai

Oceanfront Getaway, Brand New, Steps To Beach

Turtle Cove Oceanfront Views Island Sands Resort

Walk to the beach! Beautiful remodel! King bed!

Gorgeous Condo in Wailea Ekahi Village!

Cozy Beach Condo Ocean & Mountain View’s

Maui is Open - Come Support the Locals

Oceanfront Spectacular Condo, New Listing
When is the best time to visit Wailea?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$97,548 GYD | G$100,269 GYD | G$95,245 GYD | G$74,103 GYD | G$62,171 GYD | G$69,707 GYD | G$62,799 GYD | G$59,450 GYD | G$59,868 GYD | G$68,870 GYD | G$79,755 GYD | G$96,711 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 |
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- Maui
- Kaanapali Beach
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