Wailea Vacation Rentals

Discover Wailea

The word that comes to mind when thinking of Wailea is “serenity.” Located in South Maui, our Wailea vacation rentals are conveniently near beautiful beaches, breathtaking scenery, delicious cuisine, and so much more. It's the perfect area of Maui for those looking to relax surrounded by the calming ocean breeze. Wailea features 1,500 acres of pristine beach. Five public beach access points form beautiful crescent shapes on the shoreline. We have many different vacation rentals in Wailea to choose from. Miles of gorgeous views, exciting adventures, and a lush landscape will greet you when you arrive for your Wailea vacation. Explore pristine beaches, play a round of golf, catch sight of dolphins and whales, find the perfect souvenir, and try delicious local flavors. The possibilities for exploration and fun are endless and our local office, Maui Rental Group, will share even more ideas with you! Reserve your stay today and start packing your sunscreen and sunglasses for a one-of-a-kind getaway.

Wailea

Where the Fun Starts - From the moment you arrive at Wailea Point 2902, you’ll be able to relax and enjoy your precious vacation days to the fullest.
Wailea Point 2902
2 BR | 3 Full Baths | Sleeps 6 | Ocean View
Wailea, HI From $973 per night Book now
Tranquility - Imagine relaxing out here while the sun is setting, having a drink with your friends, laughing and having a good time before you turn in. Book Grand Champions 144 today!
4.5
Grand Champions 144
3 BR | 2 Full Baths | Sleeps 6 | Golf View
Wailea, HI From $698 per night Book now
Relax in Shaded Comfort - The covered patio is a great spot to enjoy the outdoors when you’ve had enough sun.
Grand Champions 78
2 BR | 2 Full Baths | Sleeps 6 | Golf View
Wailea, HI From $269 per night Book now
Picture Perfect - The view from the balcony of Grand Champions 108 could befit any postcard! Come see it for yourself.
Grand Champions 108
1 BR | 2 Full Baths | Sleeps 2 | Ocean View
Wailea, HI From $295 per night Book now
Welcome to Wailea Ekahi 17B – From the four pools to the easy access to Keawakapu Beach, you’ll find everything you need for a perfect tropical getaway at your resort.
3.67
Wailea Ekahi 17B
1 BR | 2 Full Baths | Sleeps 4 | Partial View
Wailea, HI From $520 per night Book now
Spectacular View - No matter where in the condo you are, the view is amazing!
4.8
Wailea Ekahi 17E
1 BR | 2 Full Baths | Sleeps 2 | Partial View
Wailea, HI From $336 per night Book now
Secluded Dining on the Lanai – The lush tropical vegetation surround you as you enjoy your meal on the beautiful lanai. There’s a gas grill in case you want to grill fish or burgers.
3.17
Wailea Ekahi 52B
1 Full Bath | Sleeps 4 | Garden View
Wailea, HI From $196 per night Book now
You Have Arrived - Welcome to your own personal paradise and enjoy a vacation fit for royalty!
Wailea Ekahi 33D
1 BR | 2 Full Baths | Sleeps 4 | Partial View
Wailea, HI From $499 per night Book now
Where the Fun Starts - From the moment you arrive at Grand Champions 27, you’ll be able to relax and enjoy your precious vacation days to the fullest.
Grand Champions 27
2 BR | 2 Full Baths | Sleeps 6 | Garden View
Wailea, HI From $383 per night Book now
Ready. Set. Relax. - Your vacation starts the minute you step inside Grand Champion 40. Enjoy!
Grand Champions 40
2 BR | 2 Full Baths | Sleeps 6 | Garden View
Wailea, HI From $316 per night Book now