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Wailea Vacation Rentals


VacationRentalDirect.com has found 22 Wailea Vacation Rentals that match your search criteria. Your results can be sorted by price, bedrooms, type of unit and whether the unit is pet friendly or not. All Wailea cottages, homes and vacation rentals are presented by their respective owners or managers.


Please click on the photos or links below to view the property details, then contact the owner directly (via the phone number or property inquiry button on each listing).


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Wailea, Hawaii

On the sand... Welcome to our vacation rentals in the Wailea / Makena area of South West Maui. The beach front Polo Beach Club units are located on the beach.

Wailea, Hawaii

On the sand... Welcome to our vacation rentals in the Wailea / Makena area of South West Maui. The beach front Polo Beach Club units are located on the beach.
Type: Bedrooms Bathrooms Pet Friendly Weekly Rate
Condo 2 2 No $2100 to $5000

Wailea, Hawaii

On the sand... Welcome to our vacation rentals in the Wailea / Makena area of South West Maui. The beach front Polo Beach Club units are located on the beach. 2-4 bedrooms.

Wailea, Hawaii

2 bedrm, 2 bath Ocean & Fairway Views Condo, located in Sunny South Maui. Many extras: Boogie Boards, 3 Flat Screen TV's, Beach Chairs, Fully equipped Granite Kitchen, all New Furnishings. Comfortable Tempur-Pedic Beds. ...
Type: Bedrooms Bathrooms Pet Friendly Weekly Rate
Condo 2 2 No $1750 to $2065

Wailea, Hawaii

Our luxurious two, bedroom, two bath Palms at Wailea condominium is located in the world-renowned vacation resort destination of Wailea (sunny South Maui) -- one of the more exclusive areas on the island.

Wailea, Hawaii

Enjoy Soothing vacation at Wailea beach with breathtaking views of Maui Island.

Wailea, Hawaii

Enjoy Spa Hot Tubs, Heated Oceanside Pools

Wailea, Hawaii

Enjoy Oceanviews, Gardenviews with a Large LAGOON shaped Swimming Pool

Wailea, Hawaii

Luxury Beachfront 4 Bedroom Villa for superb vacation with breath taking views.

Wailea, Hawaii

We invite you to stay at our panoramic oceanview 1 BR 2 BA condo in the exclusive, gated oceanfront Elua Village in sunny Wailea. Visit our website www.MauiCondoWailea.com for details, photos, and comments from our guest...
Type: Bedrooms Bathrooms Pet Friendly Weekly Rate
Condo 1 2 No $2450 to $2800

Wailea, Hawaii

This Villa is a newly built luxurious 4 bedroom(sleeps 8), 3,5 bathroom panoramic ocean view estate with the most stunning ocean view in all of South Maui. Villa Wailea is fully furnished with an emphasis on comfort and...
Type: Bedrooms Bathrooms Pet Friendly Weekly Rate
Villa 4 4 No $11200 to $15400

Wailea, Hawaii

Wailea Ekahi Lower Village - 1 bedroom, 2 bath Deluxe ocean view - close to the pool and beach!
Type: Bedrooms Bathrooms Pet Friendly Weekly Rate
1 2 No See Property Details

Wailea, Hawaii

Wailea Ekahi - Upper Village - 1 bedroom, 1 bath garden view condo.
Type: Bedrooms Bathrooms Pet Friendly Weekly Rate
1 1 No See Property Details

Wailea, Hawaii

Wailea Ekahi Upper Village - 1 bedroom, 1 bath garden view condo unit.
Type: Bedrooms Bathrooms Pet Friendly Weekly Rate
1 1 No See Property Details

Wailea, Hawaii

Wailea Ekahi Lower Village - Beautiful 1 bedroom, 2 bath deluxe garden view, close to the pool and beach!
Type: Bedrooms Bathrooms Pet Friendly Weekly Rate
1 2 No See Property Details

Wailea, Hawaii

Wailea Ekahi - 1 bedroom, 2 bath - Oceanview Deluxe in the Lower Village
Type: Bedrooms Bathrooms Pet Friendly Weekly Rate
1 2 No See Property Details

Wailea, Hawaii

Spectacular Wailea Ekahi - newly renovated 1 bedroom, 1 bath condo.
Type: Bedrooms Bathrooms Pet Friendly Weekly Rate
1 1 No See Property Details

Wailea, Hawaii

Wailea Ekahi - Upper Village - 1 bedroom, 2 bath garden view Condo.
Type: Bedrooms Bathrooms Pet Friendly Weekly Rate
1 2 No See Property Details

Wailea, Hawaii

Wailea Ekahi - 2 bedroom, 2 bath Condo - Gardenview in the Upper Village
Type: Bedrooms Bathrooms Pet Friendly Weekly Rate
2 2 No See Property Details

Wailea, Hawaii

Our Magical Makena Surf Condo is perfect for you ocean-front Maui vacation.
Type: Bedrooms Bathrooms Pet Friendly Weekly Rate
2 2 No See Property Details


Learn More About Wailea

Wailea has a lot to offer all visitors to the area. Below you will find writings from other Wailea vacation rental owners about the area they know best! It's a great way to learn first hand about the Wailea region and all that it has to offer!

If you are a registered vacation rental property owner on VacationRentalDirect.com and want to tell everyone about the Wailea area and additional exposure for your listing, please login here and click on 'Edit Your Listing!'

South Maui, Sunny Wailea

Posted by Barbara Marshall on Sunday, February 11, 2007


Maui is the second largest of the Hawaiian islands and is often acclaimed as the best island in the world. You'll often hear "Maui noka oi" or "Maui is the best"! South Maui basks in the glow of the golden sunshine virtually all year round and has been referred to as Hawaii's Gold Coast. The sunny resort area of Wailea wraps around some of the best beaches in Hawaii. In Wailea, there are more than a dozen beaches strung along the warm, dry coast and a full range of accommodations from exclusive condos to luxurious hotel resorts. Sculpted from 1,500 acres of kiawe brush and rugged lava, Wailea resort is the jewel of South Maui. It hugs the ocean and has 5 gorgeous crescents of sandy beaches. Travelers seeking the perfect tropical escape just might find it here in paradise.
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