
Vacation rentals in Wailea
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Top-rated vacation rentals in Wailea
Guests agree: these stays are highly rated for location, cleanliness, and more.

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!

Maui's Best - Wailea Ekahi 47A
Ekahi says it all. Don't come all the way to Maui to stay in a bargain space. Unit 47A is a one bedroom (with sleeper sofa), two-bath renovated on the ground floor. This means a larger lanai than upper units. It also means that when you step off that lanai, you step onto A LOT of grass. Our condo is a 5-minute (barefoot) walk to the most wonderful of all Maui beaches; a ten-minute walk to the shops at Wailea. Restaurants nearby. Convenient yet without the road noise.2067153903 Privacy and peace.

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

Wailea Ekolu Village 2/2 with stunning ocean view!
Halloween Special! 20% off all days October 28 - November 5! Beautiful, spacious, modern 2/2 condo located in the heart of the Wailea Resort area with gorgeous, far-reaching ocean and island views, and surrounded by brilliant, lush, flowery grounds. Super-close to dining, golf, shopping, and only a short stroll to award-winning Wailea and Ulua beaches! Please note that this condo is in the Wailea Resort area, and does not infringe upon nor remove housing from the local neighborhoods of Maui.

A.R.A Retreats: The Molokini
FULLY Renovated Summer 2023! Nicknamed “Molokini” this condo has stunning ocean view front and center of Molokini, you can witness multiple humpbacks jumping and playing during whale season from the comfort of your own private lanai. This condo is located in Wailea Ekolu in the well-known luxury resort community of Wailea. It offers a beautiful space for you to unwind after you spend all day taking in the sunshine around the island. Sit and enjoy your coffee whilst taking in our amazing views

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.

Romantic, Luxury Retreat w/Ocean View-Couples Only
Luxury 1 bedroom 2 bath condo which has been fully renovated. Our condo has lovely ocean views as well as views of the lush tropical gardens and the pool. It has a fully stocked gourmet kitchen with high end appliances, assorted spices, coffee and tea. Sunset views from the lanai are stunning. If our condo is not available during the days of your travel, please check availability at our other Wailea Palms condo at https://www.airbnb.com/rooms/1728525 Not suitable for children or infants.

Sweeping Panoramic Ocean Views - Private Ohana
Live like a local at the Ocean Blue Ohana - the private first floor of this amazing Hawaiian pole home on a half acre property in South Maui. As you enter the space, you will be drawn to the sweeping panoramic ocean views. You are sky-high, perched 500 feet above sea level, looking at the most glorious views of the neighboring islands, mountains, coastline, and Maui's amazing skyline. To top it off, you are 5 minutes from the Wailea Resorts and beautiful golden sand, crystal clear beaches.

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.

Luxury Condo w/wide Ocean View (Palms at Wailea)!
There is no better location than Wailea to experience your Maui vacation! This quiet and spacious condo has every amenity you could want to make your Maui vacation truly unforgettable. This condo is only a short walk to one of the best beaches (Keawakapu) on Maui and is also in close proximity to the Shops at Wailea. We spared no expenses in stocking this condo with everything you need to make your Maui experience memorable and luxurious.

Stunning ocean view, heated pool at home by Wailea
Ocean, sunset views, unique home reminiscent of a Victorian villa with heated private pool for guests in the villa, tropical gardens. Home renovated and maintained by designer. Cal King in main, second has twin beds. Pac n play and high chair are available. Open plan living with dining and relaxing on the lanai. Keawakapu beach, Wailea shops and restaurants 5 minutes drive. Your private view retreat. #BBMK 2016/0003

Wailea Gem-Remodeled Ocean View
Beautiful, fully remodeled Wailea Jewel! Peaceful and private location with expansive ocean views. Our newly renovated, one bedroom, 2 bathroom condo has everything you need to enjoy your Maui getaway. Located a short drive from the airport and just minutes away from some of the best beaches and dining in Hawaii. You will truly feel like you're in paradise during your stay.
Popular amenities for Wailea, Wailea-Makena vacation rentals
Stay near Wailea's top sights
Wailea, Wailea-Makena home rentals

Cajudoy's Hale - STKM 2O13-OO18/TA-081-709-8752-01

Mana Hale Vacation Rental

South Maui Guesthouse

12 Minute Walk Kamaole Beach II-Quiet Private Easy

Beautiful Beachfront Townhouse !

Maalaea Kai 307 - Maui Prime Oceanfront

Aloha Aku Honu2 Suite – Relax by the Sea in Tranqu

Modern Family Kihei Home by the Beach
Wailea, Wailea-Makena beach vacation rentals

Stunning Ocean Views

Oceanfront Getaway, Brand New, Steps To Beach

Spectacular Beachside 2BR+2BA at Maui Kamaole

Stunning Ocean Views -November Specials $169

Maui Kamaole Retreat Modern Remodel, Close 2 Beach

Sugar Beach Resort Beach / Ocean Front Unit 426

Cozy Beach Condo Ocean & Mountain View’s

Romantic Beach Retreat, New King Bed & A+ Wi-fi
Beach home rentals in Wailea, Wailea-Makena

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

Remodeled One BD Ocean, AC,wifi, pool D202

Best Studio Ocean Views at Honua Kai -Hokulani 719

Westin Ka'anapali Ocean Resort Villas North- 2bd

Walk to Front St., ALOHA CABANA, "PEOPLES CHOICE"

Oceanview Penthouse and Beach Bliss!

Beautiful One bd Ocean AC,wifi,pool A102

Exclusive Beachfront Cottage, Ocean Views, WiFi/AC
When is the best time to visit Wailea?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$72,787 GYD | G$73,414 GYD | G$74,042 GYD | G$64,839 GYD | G$58,355 GYD | G$60,237 GYD | G$57,518 GYD | G$55,427 GYD | G$53,126 GYD | G$54,172 GYD | G$58,355 GYD | G$67,767 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 vacation rentals in Wailea

Total vacation rentals
Explore 1,690 vacation rentals in Wailea

Nightly prices starting at
Wailea vacation rentals start at G$8,366 GYD per night before taxes and fees

Verified guest reviews
Over 51,140 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Vacation rentals with a pool
1,580 properties feature pools

Rentals with dedicated workspaces
910 properties have a dedicated workspace

Wi-Fi availability
1,680 of Wailea vacation rentals include wi-fi access

Popular amenities for guests
Guests love Self check-in, Beachfront, and Gym across Wailea rentals

4.8 Average rating
Wailea stays are highly rated by guests—averaging 4.8 out of 5!
Destinations to explore
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- Maui
- Kaanapali Beach
- Kahului Beach
- Lahaina Beach
- Laie
- Honolua Bay
- Sandy Beach
- Kapalua Bay Beach
- Spreckelsville Beach
- Olowalu Beach
- Pahoa Beach
- Manele Golf Course
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- Maui Ocean Center
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- Kaipukaihina
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- Palauea Beach
- Changs Beach
- Wailau Valley
- Polo Beach
- Maui Golf & Sports Park
- Old Lahaina Luau
- Wailea Golf Club




