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Book Online or call HomeAway Booking Assistance 888-640-7927
Book Online or call HomeAway Booking Assistance 888-640-7927

Penthouse 309 Amazing 4 BR Wailea with Ocean Views

Bedrooms 4
Property type condo
Minimum Stay 1 - 12 nights


About the property

Condo, 4 Bedrooms, 3 Baths, (Sleeps 8)

Penthouse 309 features one of the most spacious floor plans with a bonus 4th bedroom. Expansive Ocean Views from the great room, private balcony and Master.

Wailea Pearl is indeed a jewel. It is fabulously furnished & decorated with original art & outstanding imported artifacts. This 2600sf penthouse exceeds expectations for personal privacy with its spacious layout. The den has been converted into an extra 4th bedroom.

The private elevator is not simply an entrance into the unit, you will be both surprised and amazed by the beautiful 'Welcome Home!' you experience with its majestic frontal view of Haleakala Crater.

A step inside the formal entry hall whispers a secret glimpse of decor to come. Homage to Hawaii and its history is honored with memorabilia and unique collections from the past. A Life size shadow box showcases a traditional grass, ornately beaded Hula skirt. Legend suggests this was worn in an authentic Polynesian fertility dance, and then brought back to the US by a pre-WWII sailor stationed at Pearl Harbor for his betrothed in 1938. Other rarities include a collection of 1950's Hula dolls, Big Island Hawaii Boy Scout badges, Hawaiian sugar bags, authentic Hawaiian maps from 1898 (including original territory of Hawaii), a 1937 Hawaii Island chain map (Pre-Pearl Harbor), original sheet music from the 1920's and several vintage ukuleles. The 1940's Duke Kahanamoku pineapple style ukulele is one of our favorites as well as the special decoupage art handcrafted by the owner from skills passed down from her mother.

Open Floor plan blends upscale furnishings in a fusion of both modern contemporary pieces of Asian & Pacific Rim styles with one-of-a-kind antiquities. Dining area has mixed media table with tall back chair seating for 6 and additional seating for 5 at the counter barstools. Fully equipped gourmet kitchen features a Sub Zero refrigerator and a full size wine refrigerator both with cool drawers and ice maker. Wailea Pearl features top of the line appliances for your every comfort.

Living area has lush, comfortable couch & loveseat, flat screen TV/HBO, DVDs, books, puzzles & fun games. Black lacquer seated armchair from the late 19th century made in Shanxi, China and Elmwood low back armchairs from the Qing Dynasty in the 17 & 18th centuries. Fine art includes the delicate collection of Hawaiian airbrush paintings by Tip Freeman from the 1930-40's and inspiring works of oil Seascapes by California Impressionist Bennett Bradbury. The Pua Mana Sunset from the outskirts of Lahaina.

Master bedroom with a lovely ocean view is both relaxing & dignified. Soft buttercup walls, French regency furnishings, Asian antiques and warm red accents. Impressive bed with fine stately headboard & footboard. Sunny afternoons may evoke a sense of peace & inspiration for your creativity with writing desk facing the outstanding view of the beach. Or perhaps you choose to enjoy the comfortable side lounge chair with a good novel.

French style hutch windows open the bedroom into the luxury private en-suite with deep soaking tub & separate glass shower provides special hooks in the shower and extra hand bar, dual vanity sinks, private enclosed water closet. Master has flat screen TV and a privacy door leading direct to the front lanai. Well-furnished lanai includes dining table & chairs for 4, 2 reclining lounge chairs, as well as the desired Viking grill. View of family pool is nice for families wanting to keep an eye on children, however with fully retractable lanai doors closed, there is no audible noise from pool.

Elegantly appointed 2nd & 3rd bedrooms provide Queens, bejeweled in comforting neutral colors embellishing a vintage Hawaiiana motif. 2nd bedroom has en-suite with dual granite top vanity, glass enclosed seated shower and private water closet.

3rd bedroom shares bath with 2nd & 4th bedroom. Both rooms have peaceful green garden views.

4th (bonus bedroom) on this spacious floor plan offers Twins, large dresser and a sliding door closet with abundant storage. Twins can easily be converted to a King. Adjoining bath has a single granite top vanity and glass enclosed tub/shower combination.

Nothing is left out for your comfort as amenities provided in all bedroom suites include high thread count bedding, luxurious thick cotton towels, bath robes, make up mirror, hair dryer, high-end bath products, bedside telephones, remote ceiling fans with lights and full black out curtain option.

If you are seeking serenity in your vacation experience, look no further. The Wailea Pearl is a well thought out & tasteful 4 bedroom 3 bath home. If you are planning a larger family/group event we can compliment your accommodations and pair L309 with a neighboring Villa or Penthouse: L310, L210, L209, L509.

Luxury Penthouse Includes:

*Complimentary gift basket with Made-in-Maui treats including fresh pineapple, papaya, bananas, Maui Cookies, Maui Potato Chips, chocolate macadamia nuts and flavored macadamia nuts

*Central AC/Ceiling Fans

*Dual Phone Lines/Voice Messaging Service

*Alarm Clocks/Wake-up Calls

*Flat Screen TVs/Cable/DVD

*High Speed Internet/WiFi

*Coffee Beans/Grinder/Maker

*Blender/Toaster Oven/Electric Tea Kettle/Rice Cooker

*Convection Oven/Range/Microwave

*Starter supply of laundry and dishwasher soaps, paper products and cleaning products

Private tent cabanas are available to rent at the Grand Wailea Resort pool area.

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More Details

Property Manager
Destination Residences Hawai'i
Member since: 2007
Speaks: english
Response time:
Within a day
Response rate:
Calendar last updated:
March 13, 2018

Guestbook comments from the manager

Family of four that stayed in Penthouse 309 for 8 nights near the end of March. The staff could not have been more accomodating and the Penthouse was exceptional. The unit had an ocean view and was well equipped. Any minor issue we had was quickly resolved by the management team. Tracy was very helpful and prompt in arranging dinning, transportation and other activities. We utilized the two pools and beach location daily and found the walk from the beach to our unit to be very pleasant given the well maintained grounds. The complex itself was a nice oasis from the activity along the beach walk and around the large hotels boardering the units. We really enjoyed the proximity to the Shops at Wailea. We would highly recommend this location and look forward to returning.
Mar 2012
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Wailea Condo Accommodation and Amenities

Property Type:
  • condo
House Rules:
  • Check-in: 4:00 PM
  • /
  • Check-out: 11:00 AM
  • Max. occupancy: 8
  • Children welcome
  • Parties/events not allowed
  • Pets not allowed
  • Non smoking only ...
Location Type:
  • Ocean View ...
  • Air Conditioning ...
  • Broadband Access ...
  • Clothes Dryer
  • Covered Parking ...
  • Elevator
  • Garage ...
  • Linens Provided ...
  • Parking Off Street
  • Telephone ...
  • Washing Machine ...
  • Wireless Internet ...
  • Catering Available ...
  • Cooking Utensils ...
  • Dishwasher
  • Ice Maker
  • Kitchen ...
  • Microwave
  • Refrigerator ...
  • 3 Bathrooms
  • Bathroom 1 -
    Bathroom 2 -
    Bathroom 3 -
  • 4 Bedrooms, Sleeps 8
  • King size beds (1), Queen size Beds (2), Twin or Single Beds (2) Versatile two twin beds can be joined together to make King size bedding. , Baby Cribs (1) Cribs are available upon request, for a small charge., Sleep Sofa or Futons (1) Living room couch converts into a sofa bed for additional sleeping accomodations.
  • CD Player
  • DVD Player ...
  • Pool Table
  • Satellite / Cable ...
  • Stereo
  • VCR
  • Lanai / Gazebo ...
  • Outdoor Grill
  • limited accessibility
  • wheelchair accessible
Pool / Spa:
  • Communal Pool ...
  • Shared Hot Tub ...
  • cinemas
  • health/beauty spa
  • live theater
  • museums
  • restaurants
Leisure Activities:
  • antiquing
  • boating
  • horseback riding
  • miniature golf
  • shelling
  • shopping
  • sight seeing
  • wildlife viewing
Local Services & Businesses:
  • fitness center
Sports & Adventure Activities:
  • cycling
  • fishing
  • golf
  • hiking
  • jet skiing
  • kayaking
  • mountain biking
  • parasailing
  • rafting
  • sailing
  • snorkeling/diving
  • surfing
  • swimming
  • tennis
  • wind-surfing
Gated condominium community. Family oriented, but more private than hotel. On property security 24 hrs.


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Nearest Airport
18 Miles
OGG Kahului Maui
Car: necessary

Helicopter tours, paragliding, skeet shooting, ATV tours, downhill bike from volcano, kite surfing, ultralights, hang gliding




Additional information about rental rates

Tax Rate 17.02%

Manager's Cancellation Policy

  • 50% refund if canceled at least 30 days before arrival date.
  • 100% refund if canceled at least 60 days before arrival date.
  • Service Fee fully refunded on cancellations that qualify for 100% refund.

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