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Penthouse 309 Amazing 4 BR Wailea with Ocean Views

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Ocean & island views from your relaxing lanai


Last updated: 04/25/2017
Check availability
23 Available
21 Unavailable
22 Today
23 Selected dates
  • Minimum stay:1-10 nights
  • Sleeps:8
  • Bedrooms:4
  • Bathrooms:3
  • Property type:Condo
  • Internet:Yes
  • Pets considered:No
  • Wheel chair accessible:Yes

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.

Keywords: Luxury Condo Vacation Rental, Maui, Hawaii, Villas, Wailea Beach Villas, Villas Rentals, Villa Rental Maui, vacation home, pool, air conditioning, waterfront, oceanfront, luxury, swimming beach, shopping, dining, golfing, surfing, snorkeling, room service, private villa, infinity pool, Wailea beach villas, Wailea beach, Wailea condo rental, Wailea villa rental, holiday house Hawaii, holiday house Maui, Destination Resorts, Hawaii hideaways, tropical villa vacations, Penthouse Maui, Penthouse Hawaii, luxurious destinations, villas for rent Maui Hawaii, private villa in Maui, tropical beach vacations, tropical vacation villas Maui, luxury retreats, luxury vacation, Maui beach home, water bungalows, Maui beach villas, Maui luxury condo rental, Destination Resorts Hawaii, Villa, Penthouse Conde Nast Traveler Readers Choice Awards, #1 Specialty Lodging, Penthouse 309, Tax ID 46640346-01
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Member since: 2007

Speaks: english
Calendar last updated: 04/25/2017

Property Type

  • Condo

House Rules

  • Max. occupancy 8
  • Children Welcome
  • Non Smoking Only:

    No smoking in this unit....moreless

  • Pets Not Allowed

Accommodation Type

  • Vacation Rental


  • Limited Accessibility
  • Wheelchair Accessible

Bedrooms: 4 Bedrooms, Sleeps 8, Beds for 8

  • Bedroom 1


  • Bedroom 2


  • Bedroom 3


  • Bedroom 4


  • 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....moreless

Bathrooms: 3 Bathrooms

Other Amenities

  • Gated condominium community. Family oriented, but more private than hotel. On property security 24 hrs....moreless


  • Pool Table
  • Satellite / Cable:

    (4) Flat screen TVs with DVD/VCR in bedrooms and living room. Wall-mounted adjustable screen in LR....moreless

  • Stereo
  • VCR


  • Cinemas
  • Health/Beauty Spa
  • Live Theater
  • Museums
  • Restaurants

Local Services & Businesses

  • Fitness Center

Leisure Activities

  • Antiquing
  • Boating
  • Horseback Riding
  • Miniature Golf
  • Shelling
  • Shopping
  • Sight Seeing
  • Wildlife Viewing

Location Type

  • Ocean View:

    Superb view of islands and ocean....moreless

Sports & Adventure Activities

  • Cycling
  • Fishing
  • Golf
  • Hiking
  • Jet Skiing
  • Kayaking
  • Mountain Biking
  • Parasailing
  • Rafting
  • Sailing
  • Snorkeling/Diving
  • Surfing
  • Swimming
  • Tennis
  • Wind-Surfing


  • Air Conditioning:

    Keep cool with central air conditioning and individual room controls, or the open your screened windows to enjoy the tropical Hawaiian breeze and run the remote controlled fans provided in each room. ...moreless

  • Broadband Access:

    Available at no extra charge....moreless

  • Clothes Dryer
  • Covered Parking:

    Additional parking in garage or open area parking available for no charge....moreless

  • Elevator
  • Garage:

    Assigned parking for easy access to your semi-private penthouse elevator. ...moreless

  • Linens Provided:

    Duvets and Egyptian cotton sheets, fluffy towels and complimentary robes...moreless

  • Parking Off Street
  • Telephone:

    (4) Telephones in living area and bedrooms...moreless

  • Washing Machine:

    Experience the convenience of separate laundry room with door just off the unit entrance hall. Laundry room includes full size washer and dryer, storage area with utility sink, laundry hamper and basket, washing soap and dryer sheets along with iron and ironing board. ...moreless

  • Wireless Internet:

    Situated conveniently to desk area. Available at no extra charge....moreless


  • Catering Available:

    Room service from Longhi's restaurant available 9am to 9pm, private chef available for dining or catering events on request. Pantry and refrigerator stocking available prior to arrival through the WBV concierge services. Great feature, makes for an easy vacation transition....moreless

  • Cooking Utensils:

    Top line appliances, gourmet coffee maker, toaster, blender and everything you need to enjoy your vacation....moreless

  • Dishwasher
  • Ice Maker
  • Kitchen:

    Fully stocked with appliance amenities makes this full size kitchen with custom cabinets, granite countertops and marble floors a joy to cook home away from home. 2 Sub Zero refrigerators, Gaggenau Ceran glass surface cooking range, Thermador stainless steel convection oven with microwave and a full assortment quality serving and dining dishes, bar ware and flatware. Also includes all the grilling equipment you might need for the gas-flame outdoor Viking grill on your private lanai....moreless

  • Microwave
  • Refrigerator:



  • Lanai / Gazebo:

    Overlooks family pool, furnished with dining area and lounge chairs, view of ocean and islands. ...moreless

  • Outdoor Grill

Pool / Spa

  • Communal Pool:

    (2) The 2 heated pools on property provide fresh towels, sunscreen, and cold drinking water. The family pool also provides water toys for children....moreless

  • Shared Hot Tub:

    (2) WBV has 2 heated whirlpool spa hot tubs on property. One beside the family pool and one at the ocean front pool....moreless



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Rental basis: Per property
Dates Nightly Weekend Night Weekly Monthly * Event
Nightly Rate
Apr 17 - May 31, 2017
3 night min stay
Nightly Rate
Jun 1 - Aug 31, 2017
3 night min stay
Nightly Rate
Sep 1 - Oct 31, 2017
3 night min stay
Nightly Rate
Nov 1 - Nov 20, 2017
3 night min stay
Nightly Rate
Nov 21 - Nov 29, 2017
3 night min stay
Nightly Rate
Nov 30 - Dec 19, 2017
3 night min stay
Winter Holiday
Dec 20 - Jan 3, 2018
10 night min stay
Nightly Rate
Jan 4 - Apr 1, 2018
3 night min stay
Nightly Rate
Apr 2 - Dec 19, 2018
3 night min stay

Additional information about rental rates


  • Tax Rate 16.02%

Manager's cancellation policy:

Policy available by contacting manager when booking

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Last updated: 04/25/2017
Check availability
23 Available
21 Unavailable
22 Today
23 Selected dates


18 Miles
Nearest Airport
OGG Kahului Maui

Car: Necessary

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


Manager info

Contact us

Speaks: english
Calendar last updated: 04/25/2017

Send email

Links to more information:

Guestbook comments from the property manager

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  • Ocean & island views from your relaxing lanai

    Ocean & island views from your relaxing lanai

  • Expansive living space with island furnishings/carvings throughout

    Expansive living space with island furnishings/carvings throughout

  • European style gourmet kitchen with bar seating & granite countertops

    European style gourmet kitchen with bar seating & granite countertops

  • Beautiful private master bedroom

    Beautiful private master bedroom

  • Lovely second bedroom with antique furnishings

    Lovely second bedroom with antique furnishings

  • Pineapple twin beds in 3rd bedroom

    Pineapple twin beds in 3rd bedroom

  • Bonus 4th bedroom

    Bonus 4th bedroom

  • Tastefully appointed large great room

    Tastefully appointed large great room

  • Ocean and property perspective from your lanai

    Ocean and property perspective from your lanai

  • Elegant dining or bar seating at the gourmet kitchen counter

    Elegant dining or bar seating at the gourmet kitchen counter

  • Master Bedroom has lovely ocean view

    Master Bedroom has lovely ocean view

  • Double Vanity bathrooms

    Double Vanity bathrooms

  • 2nd bedroom

    2nd bedroom

  • Twin beds can be pushed together as a king

    Twin beds can be pushed together as a king

  • High back seat dining for 6

    High back seat dining for 6

  • High end art throughout entire unit

    High end art throughout entire unit

VRBO #174185

This listing was first published here in 2008.

Date last modified - Thursday, April 27, 2017

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