Search over 150,000 vacation rentals properties now! Click here to see more Vacation Homes
Search for vacation rental homes in Wailea
Beautiful Beaches are Only the Beginning in Wailea
With an unbeatable location on Maui’s sunny southern shore, Wailea invites you to leave all your worries behind on a getaway filled with white sand beaches, countless water sports, and scenic beauty that is beyond compare.
Once you step foot onto the land that is Wailea, it is easy to see how this place can truly be called paradise. One magnificent beach after another beckons with opportunities for swimming, snorkeling, scuba diving and even kayaking; all you need to do is heed the call and let every last ounce of stress fall by the wayside.
So where should you begin? Any of the beautiful beaches are certainly a treat, but Wailea Beach is the best place to get your feet wet with its spectacular swimming conditions, breathtaking views of Kahoolawe and Lanai, and gentle boogie boarding possibilities. And see that little crescent out in the distance? That is Molokini Crater, where you will be snorkeling or scuba diving in crystal clear water surrounded by schools of colorful fish.
However, if your Wailea vacation rental lies along a different stretch of sand, you can’t be too disappointed because the other options can certainly hold their own. The long golden sands of Mokapu Beach and Ulua Beach can satisfy your need for adventure with amazing snorkeling and swimming in calm water and spectacular bodysurfing when the waves kick up, while Polo Beach is a great place to simply relax, swim or snorkel to your heart’s content.
Although the beaches are certainly the centerpiece of Wailea, this area is more than just a one attraction wonder. If you are looking for other ways to fill up your stay in paradise, the three courses at the Wailea Golf Club, the renowned tennis of the Wailea Tennis Club, the one-of-a-kind treasures at The Shops at Wailea, and the natural beauty of La Perouse Bay are all waiting to make your Maui vacation everything you always imagined and more.
-
Wailea Grand Beach Villa
Wailea Beach Villa for 8- Rated Perfect on TripAdvisor — Property 230622
- Villa
- 4 bedrooms , sleeps 10
- 3 bathrooms
- beach, resort
- pool
Wailea Beach Villa Luxury 4BR $750/niteS P E C I A L O F F E R- Rates (shown in USD)
- $7665 - $10500 per property per week
-
Luxury Maui Ocean View, Grand Wailea Resort Amenities — Property 246371
- Townhome
- 3 bedrooms , sleeps 10
- 3 bathrooms
- 1 half bathroom
- near the ocean, resort
- pool
- Rates (shown in USD)
- $5250 - $17465 per property per week
-
Wailea Sunset Estate — Property 95990
- House
- 3 bedrooms , sleeps 10
- 4 bathrooms
- 1 half bathroom
- accept credit card
- activities guide
- Rates (shown in USD)
- $11550 - $17850 per house per week
-
Wailea Grand Beach Villa Elite
$750/Night Fall Stunning 4 BR Wailea Beach Villa — Property 164181
- Villa
- 4 bedrooms , sleeps 10
- 3 bathrooms
- beach, waterfront
- pool
- Rates (shown in USD)
- $6965 - $10500 per property per week
-
Modern Hawaiiana Masterpiece
Architect's Own Estate in South Maui — Property 159525
- House
- 4 bedrooms , sleeps 10
- 3 bathrooms
- 1 half bathroom
- near the ocean, resort
- pool
- Rates (shown in USD)
- $8750 - $12600 per property per week
-
Ocean Front Home, Private Luxury in Kihei-Wailea, Hawaii — Property 245114
- House
- 3 bedrooms , sleeps 12
- 3 bathrooms
- beach, waterfront
- garden
- Rates (shown in USD)
-
Ho'Olei Ocean View With Grand Wailea Resort & Spa Privileges — Property 248321
- Townhome
- 3 bedrooms , sleeps 9
- 3 bathrooms
- 1 half bathroom
- near the ocean, resort
- pool
- Rates (shown in USD)
- $3750 per property per week
-
Heavenly Sunsets: Exclusive Private Villa — Property 96712
- Villa
- 5 bedrooms , sleeps 10
- 4 bathrooms
- coffee maker
- children welcome
- Rates (shown in USD)
- $10500 - $11900 per villa per week
-
Magical Wailea Home in Private Gated Community — Property 194773
- House
- 5 bedrooms , sleeps 10
- 3 bathrooms
- 1 half bathroom
- beach, near the ocean
- jacuzzi
- Rates (shown in USD)
-
Wailea Dreams Estate — Property 7008764
- House
- 4 bedrooms , sleeps 10
- 6 bathrooms
- adventure
- air-conditioning
- Rates (shown in USD)
- $12950 - $28000 per house per week
Refine Your Search
- You refined by:
- Wailea remove
- sleeps_9_or_more remove
- fishing remove
- (remove all)
Bedrooms
- 3 bedrooms (4)
- 4+ bedrooms (6)
Baths
- 3 bathrooms (7)
- 4+ bathrooms (3)
Lodging Type
- house rentals (5)
- townhome rentals (2)
- villa rentals (3)
Amenities
- satellite or cable tv (9)
- pool (9)
- internet access (8)
- washing machine (9)
