
Vacation rentals in Wailea
Find and book unique accommodations on Airbnb
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 an 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

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

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.

MAUI BLISS! RARE Wailea 3-bedroom...sleeps 10!
This is the one you've been waiting for! Perfect for families, couples, or anyone who loves to spread out, this 1700 sq ft Grand Champions 3 bedroom has been painstakingly remodeled with luxury finishes throughout. Two kings, two pull-out queens, plus...bunk beds! Nestled in the most peaceful corner of the resort, boasting stunning ocean views from the lanai, and minutes away from Wailea beaches, restaurants, and shopping, this is truly what Maui vacation dreams are made of!

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

*Fully Remodeled* Modern Island Style*
I am looking forward to hosting you at the Palms at Wailea 606 and making your vacation fun and enjoyable. The Palms is an upscale community that offers you great shopping, dining, golfing, world-class resorts, and beaches all within a few minutes. I offer you a clean, comfortable and memorable stay on the island. I want to make your Maui dreams come true! Mahalo and looking forward to seeing you! -Aini

Ocean Front Vibes Maui
Wake up to panoramic ocean views and end your day with sunsets from your private lanai in this top-floor corner condo at Haleakala Shores. Just steps to Kamaole Beach Park III with easy elevator access. Beautifully remodeled in 2020, fully stocked, and walkable to dining, shops & snorkeling. Light road noise possible. See more videos & details on social at oceanfrontvibesmaui Maui's airport code is OGG

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 beach vacation rentals

Stunning Ocean Views

Newly Remodeled 1bed/1bath, Kihei/Wailea

Chic Maui Condo Steps From Beach & Ocean

Stunning Ocean Views - Jan Special $265

Cozy Beach Condo Ocean & Mountain View’s

Romantic Beach Retreat, New King Bed & A+ Wi-fi

Top Floor Ocean Views | Beach & Restaurant Access

Beauty & the Beach: Remodel+Ocean Vws! A+ Location
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 !

Oceanview Home with Private pool and hot tub

Maalaea Kai 307 - Maui Prime Oceanfront

Aloha Aku Honu2 Suite – Relax by the Sea in Tranqu
Beach home rentals in Wailea, Wailea-Makena

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

Oceanfront Koa Lagoon Condo w/ Sunset Views

Remodeled One BD Ocean, AC,wifi, pool D202

Oceanfront 2BR w/AC - Walk out to Beach!

A201a-The closest Maui Banyan studio to the beach

Beautiful One bd Ocean AC,wifi,pool A102

Exclusive Beachfront Cottage, Ocean Views, WiFi/AC

Stunning Ocean Two Bd Corner Condo,AC,Pool D301
When is the best time to visit Wailea?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$72,849 GYD | G$73,477 GYD | G$74,105 GYD | G$64,894 GYD | G$58,405 GYD | G$60,289 GYD | G$57,568 GYD | G$55,474 GYD | G$53,172 GYD | G$54,218 GYD | G$58,405 GYD | G$67,825 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$8,373 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
- Rentals with a sauna Wailea
- Rentals with beach access Wailea
- Rentals with outdoor seating Wailea
- Rentals with an EV charger Wailea
- Waterfront rentals Wailea
- Family-friendly rentals Wailea
- Beach condo rentals Wailea
- Villa rentals Wailea
- Fitness-friendly rentals Wailea
- Apartment rentals Wailea
- Condo rentals Wailea
- Rentals with pools Wailea
- Rentals with a patio Wailea
- Townhouse rentals Wailea
- House rentals Wailea
- Hotel rooms Wailea
- Rentals with a washer and dryer Wailea
- Serviced apartment rentals Wailea
- Rentals with a kayak Wailea
- Beachfront rentals Wailea
- Rentals with a hot tub Wailea
- Pet-friendly rentals Wailea
- Maui
- Kaanapali Beach
- Kahului Beach
- Lahaina Beach
- Honolua Bay
- Sandy Beach
- Pahoa Beach
- Spreckelsville Beach
- Kapalua Bay Beach
- Olowalu Beach
- Manele Golf Course
- Maui Ocean Center
- Wailea Beach
- Hāmoa Beach
- Palauea Beach
- Puu Olai Beach
- Changs Beach
- Kaipukaihina
- Polo Beach
- Maui Golf & Sports Park
- Old Lahaina Luau
- Ka'anapali Golf Courses
- Kapua
- Wailau Valley




