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Wailea Sunset Bungalow - Private Oceanfront Cottage near Wailea

Bedrooms 2
Space 1,000 sq ft
Property type bungalow
Minimum Stay 5 - 12 nights


About the property

2 Bedrooms, 1 Bathrooms, Sleeps up to 4

State of Hawaii Transient Accommodations Tax License #TA-199-682-2528-01

County of Maui Short-Term Rental License #Hotel-Zoned

Wailea Sunset Bungalow is located on Maui island voted #1 best island in the WORLD by TripAdvisor's 2016 Travelers' Choice Awards! Maui island was also voted #1 best island in the U.S by Conde Nast Traveler's Readers' Choice Awards published on October 18 2016.

Visit The NEW Wailea Sunset Bungalow! Extensively renovated updated and re-decorated from top to bottom inside and out!

Please read the effusive guest comments to learn why the Bungalow has always been one of the most popular legal vacation homes in the Wailea-Makena area for nearly 20 years.

We now provide a 3 piece Italian ivory vanilla color leather sofa set with 2 full size sofas 1 love seat 1 arm chair with matching ottoman wood coffee table and a unique over-dyed wool rug in beautiful shades of deep blue eggplant turquoise and teal The expansive area rug anchors the living room and provides a sense of classy coziness in the extensively improved oceanfront vintage cottage.

The adorable oceanfront 2 bedroom Wailea Sunset Bungalow has just been renovated and redecorated with more than $200,000.00 of upgrades Reserve now and enjoy the priceless ambiance of this unique oceanfront cottage set on a sprawling one acre property Your visit will be enhanced with an array of all-new modern comforts Below is just a few of the improvements completed for the Wailea Sunset Bungalow

- All new kitchen with new Pentel quartz counters solid wood cabinets stainless sink and faucet double oven with ceramic range top and vent hood refrigerator with filtered water dispenser and ice maker dishwasher ceiling fan armoire for extra storage and bamboo flooring We also stocked new kitchen goods dishware and cooking supplies

- Multiple split-zone central air conditioning units Every room including the bathroom has AC outlets There are 2 zones available with individual remote controls for separate settings

- New roof with insulation for more effective cooling

- Strand bamboo hardwood floors throughout New vinyl tile flooring in the bathroom

- New tub toilet and fixtures in the bathroom

- New paint throughout all interior rooms

- All new double hung solar glazed thermal windows on all four sides of the house

- New woven wood blinds in the kitchen and great room

- New furniture and decor in the king bed master bedroom including dupioni silk black-out drapes

- New wall decor and silk dupioni black-out drapes in the second bedroom This room offers a choice of 2 twins or 1 king bed

- New exterior vinyl siding and paint including over the deck

- New living room furniture (multi-piece Italian vanilla ivory color leather sofa set) side arm chair with ottoman in corner custom wall art by Hana artist Sarai Strickland solid wood dining chairs to match the 6 person indoor dining table a wool area rug new glass lamps and retro vintage ceramic lamp

- New HD 55 inch TV in the living room Televisions with HD cable subscription and complimentary Netflix access

- Live green plants

- Additional new patio furniture including arm chairs with ottomans rockers dining space for up to 6 guests folding oversized shade umbrellas

- Additional garden furniture

- Improved outdoor landscaping new solar lights new tiki torches and hammock

- Re-built carport structure

- Upgraded electrical system and plumbing

The Wailea Sunset Bungalow is one of the very few legal hotel-zoned vacation rental homes on Maui Tiki torches add romance to an already amazing setting Nothing but your hammock hot tub and a sprawling manicured grass lawn come between your cottage and the beautiful blue Pacific ocean.

The Wailea Sunset Bungalow may be rented separately or in combination with the adjacent Wailea Sunset Estate When rented together both properties total 6 bedrooms and 6.5 baths for up to 14 guests.

We encourage all prospective guests to please read the extensive guest comments by clicking on the Testimonials link The effusive and satisfied comments from past customers tell it all but here are just a few more:

"Thank you for opening this home to guests We greatly enjoyed our stay here We were very appreciate of our proximity to the ocean We just enjoyed listening to the waves and birds Seeing turtles out front was delightful We were very fortunate to have the best sunset our last evening here which just made it that much more special To more sunsets and to all those who stay here... Cheers!" V Family

"This is the third year in a row that my sister-in-law and I have stayed in your quintessential tropical paradise Each year we appreciate the ability/opportunity to be your guests more Thank you for providing/sharing this luxurious yet simple island paradise My husband and I are frequent visitors to Maui and we can't imagine staying anywhere else as this is "Hawaii" We cannot wait to come back Mahalo Mahalo Mahalo T Family

"Wow! Turtles Whales a beautiful bungalow and PARADISE I`m dizzy Who could ask for anything else? I mean an outdoor shower Jacuzzi a beautiful view and a huge play area Now that is what I call paradise We enjoyed this beautiful house for 8 days and never got tired of it After we finished one thing we were off to the next! We'll be back!"

"Just a beautiful spot Mai Tais on the lawn each evening Watching the turtles bob up and down with whales breaching behind them Ridiculous!! Sandy beach just down the path is worth spending a few afternoons relaxing You'd be hard pressed not to enjoy this place."

"We are back from Maui and missing it already I was just watching some video shot at the Bungalow The Wailea Sunset Bungalow was just a joy I have never stayed in a rental property that was so fully stocked with stuff It is luxurious there and very comfortable We had some nice dinners at the Bungalow Well we are super spoiled now and will have to come back for more Maui fun! Thanks again and we hope to book the Bungalow in the future Thanks for all you do to make your renters comfortable."

The Wailea Sunset Bungalow is a little piece of heaven on earth The Wailea Sunset Bungalow is a vintage cottage with charming nostalgic ambiance reminiscent of Hawai`i of yester-year Choose the Wailea Sunset Bungalow and experience seaside living as it was before the introduction of mega-mansions to our tropical island paradise.

This is not new construction We make every effort to provide comfortable furniture abundant electronics and useful amenities The 2 bedroom and 1 bath Bungalow has an outdoor hot tub spa air conditioning in all rooms iPod dock multiple HD televisions high speed wireless internet access four padded outdoor chaise lounge chairs hammock indoor and outdoor dining and best of all a simply priceless location nestled between 2 sandy swimming beaches.

Unlike at many nearby hotels there are no extra "Resort Fees" charged!

Guests of the Bungalow may enjoy their own private hot tub under the stars with panoramic views of the turquoise ocean and crimson sunsets From time to time when a south swell is generated in the South Pacific some smaller waves break along the shoreline A verdant manicured sprawling green grass lawn frames the properly perfectly.

The Bungalow has a gated entry a comfortable living room with plenty of seating and fabulous floor to ceiling sweeping ocean views indoor and outdoor dining additional outdoor hot & cold outdoor garden shower wi-fi netflix HD television programs washer and dryer and iron and board safe fully equipped kitchen a propane BBQ grill beach chairs and towels and many other amenities to provide you with life long memories of a terrific sea-side holiday.

One bathroom is conveniently placed between the 2 bedrooms There are 3 televisions one in each bedroom each with a DVD player and a separate CD player and iPod dock in the master bedroom HD television programs and Netflix are also available!

Stroll just one block to sandy swimming beaches (Polo Beach or Palauea White Rock Beach) or swim snorkel scuba dive boogie board surf or kayak directly from the shore in front of the Bungalow.

The Fairmont Kealani Resort Cafe Ciao Deli and Store Four Seasons Resort Wailea Blue Golf Club Mulligan's Irish Pub and other upscale restaurants and shops in the swanky new Shops at Wailea are just a few easy blocks away Hike over one block to pick up a pizza or fresh pastries from the Fairmont Kealani Deli and dine leisurely back home on your own private ocean front deck.

Guests of Private Paradise Villas receive special rates at the Wailea Golf Club The club offers players some of the most verdant and picturesque golf of any tropical destination world-wode at three exceptional oceanview courses the Blue Emerald and Gold.

As a Private Paradise Villas guest you also now have an opportunity to play golf at Maui's premiere private club The King Kamehameha Golf Club for a special limited time per player fee of $195 + tax in the mornings and $175 + tax in the afternoons a great discount from the regular price of $225 and $205 plus tax Limited tee times available ask your Personal Concierge for reservations! You are also invited to visit their Frank Lloyd Wright designed clubhouse that is adorned with exquisite Hawaiian art where lunch is served in the Wai Kahe Restaurant You may also want to experience the comforts of the private club with their talented massage therapists.

GUESTS of Private Paradise Villas rental management and reservation service receive access to many valuable services..


- Complimentary Late Check-Out (when available - confirmed during week of departure)

- An abundant array of pre-stocked supplies including bountiful numbers of towels extra linens paper products office supply

- Extensive supply of good-quality cooking and dining supplies

- Top-quality in-villa coffee and tea making facilities (some villas have espresso machines) herbs/spices whole fresh coffee beans

- In-Villa Safe and Copier/Scanner/Printer/Fax Local Calls Parking

- Bona-Fide...

Private Paradise Villas Real Estate Broker License #17787

Irene Ann Aroner, Realtor, Principal Broker License #18795

State of Hawaii Travel Agency License TA #3570

Private Paradise Villas Activity Desk License #193

More Details

Property Manager
Speaks english
Response time
Within a day
Response rate
Calendar last updated:
21 June, 2018

What makes this bungalow unique

We are the original villa rental agency that pairs extraordinary vacation residences with complimentary "Personal Concierge Service". We are proud to be named the "Villa Rental Specialist for Hawaii" by Conde Nast Traveler Magazine in the 2012 to 2007 issues. We are the direct rental source for an extraordinary collection of select and ultra-luxurious villas on the island of Maui, Hawaii. The vacation residences featured in the Private Paradise Villas boutique collection serve as "Your Own Private Paradise" where you can relax and refresh in true luxury and true togetherness with every comfort and convenience provided. Select one of our exclusively managed and sumptuously prepared resort villas or homes, and experience an effortless vacation where you can "Delight In Every Moment". Private Paradise Villas is the exclusive rental agent and property manager for a custom curated collection of homes and villas throughout Maui, Hawaii.

Private Paradise Villas (previously named Tropical Villa Vacations), a dedicated in-house property management agency, is the direct rental source for an exceptional and extraordinary collection of select and sumptuous ultra-luxurious beach front vacation estates, elegant villas, secluded retreats, and romantic hideaways on the island of Maui, Hawaii. Private Paradise Villas is the exclusive rental agent and property manager for a custom curated collection of homes and villas throughout Maui. Add value and pleasure to your precious holiday with an abundance of personal pampering enhancements. After you've booked your property, your Personal Concierge is available for all of your family's Travel Needs, Private In-Villa Chef Service, Private Yoga, Massage, and other Wellness and Fitness Fun, Art, Cultural and Sightseeing Explorations, Private Boat/Sailing/Scuba or Snorkel Charters, Helicopter or Hiking Charters, Golf and Dining Reservations, Personalized itinerary.

Guestbook comments from the manager

Aloha Yvonne, (Tropical Villa Vacations Concierge) So sorry I missed you when you dropped by this afternoon. When we returned from our walk, my mom and dad said “we had the most delightful visit from Yvonne!”. They were so touched and charmed by your concern, as are Max and I. Thank you! My mom’s unfortunate accident/injury has not in any way diminished our devotion to this property (both bungalow and estate). We can only hope that we are able return again and again and again. Please convey our gratitude to the property owners, along with the hope that they continue to offer this amazing property on a rental basis. It is truly both singular and spectacular, and we love it. We will never again be able to enjoy Maui from a hotel room, no matter how grand. We are forever spoiled by the cherished time we’ve been able to spend here. Aloha nui,
Feb 2016
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Accommodation and facilities for this holiday bungalow rental in Wailea, Hawaii

Property Type:
  • bungalow
  • Catering available
  • Housekeeper Optional
Floor Area:
  • 1000 sq ft
House Rules:
  • Check-in: 3:00 PM
  • /
  • Check-out: 11:00 AM
  • Max. occupancy: 4
  • Min. age of primary renter: 21
  • Children welcome
  • Parties/events not allowed
  • Pets not allowed
  • Non smoking only
Location Type:
  • Beach View
  • Beachfront
  • Mountain View
  • Near The Ocean
  • Ocean View
  • Oceanfront
  • Water View
  • Waterfront
  • Budget
  • Family
  • Romantic
  • Spa
  • Sports & Activities
  • Tourist Attractions
  • Air Conditioning
  • Clothes Dryer
  • Hair Dryer
  • Internet
  • Iron & Board
  • Linens Provided
  • Living Room
  • Parking
  • Telephone
  • Towels Provided
  • Washing Machine
  • Coffee Maker
  • Dishes & Utensils
  • Dishwasher
  • Kitchen
  • Microwave
  • Pantry Items
  • Refrigerator
  • Stove
  • Toaster
  • Dining Area
  • Dining Room
  • seating for 6 people
  • 1 Bathroom
  • Bathroom 1 - toilet , bath with shower , Shared Hall Shower/Tub Bath
  • 2 Bedrooms, Sleeps 4
  • Bedroom 1 - 1 extra lg. double bed , King Bed
    Bedroom 2 - 1 extra lg. double bed , 2 single bed , 1 King Bed or 2 Twin Beds
  • Books
  • DVD Player
  • Games
  • Satellite / Cable
  • Stereo
  • Television
  • Balcony
  • Deck / Patio
  • Lawn / Garden
  • Outdoor Grill
Pool / Spa:
  • Heated Pool
  • Hot Tub
Onsite Services:
  • Car Available
  • Concierge
  • Massage
  • Private Chef
  • Staff
  • bay
  • botanical garden
  • churches
  • festivals
  • forests
  • library
  • marina
  • museums
  • naturist beach
  • rain forests
  • recreation centre
  • reefs
  • restaurants
  • ruins
  • volcano
  • waterfalls
  • winery tours
Leisure Activities:
  • beachcombing
  • bird watching
  • eco tourism
  • horse riding
  • horseshoes
  • luaus
  • photography
  • scenic drives
  • sight seeing
  • walking
  • whale watching
Local Services & Businesses:
  • ATM/bank
  • Babysitter
  • fitness centre
  • groceries
  • hospital
  • laundrette - serviced
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • basketball court
  • cycling
  • deepsea fishing
  • fishing
  • golf
  • golf pass optional
  • hiking
  • mountain biking
  • paragliding
  • pier fishing
  • sailing
  • diving
  • snorkelling
  • bay fishing
  • surf fishing
  • surfing
  • swimming
  • tennis
  • wind-surfing


5/5 -
(5 traveller reviews)

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Wailea Sunset Bungalow - Private Oceanfront Cottage near Wailea
average rating of 5.0 based on 113 reviews

Absolutely Amazing!

  • 5 of 5

The sunset estate and bungalow is a stunning set of properties and worked perfectly for our family vacation (10 adults, 7 children). As the name suggests, you are treated to beautiful sunsets each evening that can be enjoyed on a huge patio complete with a pool. Being on the oceanfront, we were even lucky enough to have a couple sea turtles visit the beach in front of the house. The property managers were extremely helpful leading up to the trip and during our stay (offered to plan activities, help with rentals, etc.). The property managers also recommended a private chef (they provided a list; we selected Chef John) who prepared a fantastic surf & turf dinner for our group. We would highly recommend this property!

  • Review Submitted: 24/07/2017
  • Date of Stay: July 2017
  • Source: VRBO, from HomeAway
Owner's Response: Mahalo nui loa to our wonderful guests who took the time to write such a fabulous review of our incredible Wailea Sunset Estate & Bungalow. We do offer to all of our guests, our excellent concierge services for all of your actiivty & reservation extra's. We look forward to welcoming you back to our beautiful estate property and encourage you to to share this beauty with your family and friends! Until then, a hui hou from the entire staff at Private Paradise Villas on Maui no ka oi!
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Upscale hotel living in a private home...

  • 5 of 5

What an amazing place to spend time in your own private paradise! The house is decorated beautifully and the pictures are almost accurate - it's actually cuter and cozier than it looks in the photos.

The first day we were very alarmed as large pods were being "thrown" at the house. I decided that the house was infested with invisible monkeys. After a bit of research, we learned the invisible monkeys were actually a monkeypod tree. You'll see large pods littering the deck - break one open and smell it. It's a woodsy smell of mesquite and anise.

We made a point to watch every sunset at the house. Even though there are houses on either side, it feels very private. The grounds are beautifully landscaped and there's fantastic snorkeling right in front of the house (assuming the water is clear).

We enjoyed the house so much that we stayed in far more than we planned.

If you're looking for a private, secluded ocean paradise, look no further. I would absolutely stay here again.

  • Review Submitted: 08/06/2017
  • Date of Stay: May 2017
  • Source: VRBO, from HomeAway
Owner's Response: What a wonderful review of our beautiful Wailea Sunset Bungalow, thank you!! We’re always thrilled when guests say our villa is better in person than our professional photos can show. We’re so happy that you enjoyed the home with it’s gorgeous sunset and ocean views. We look forward to welcoming you back as our guests and hope to see you again soon! With Lots of Aloha, The Team at Private Paradise Villas
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Woodside, CA

Wailea Sunset Bungalow

  • 5 of 5

My husband and I spent more than a week at WSB with our teenage daughter and her friend. While there is only one bath, there are three words to describe this place: location, location, location! Waterfront, in Wailea, but really a world away as it is so private. Perfectly equipped, attractively decorated, we only wish we could have stayed longer!

  • Review Submitted: 07/04/2016
  • Date of Stay: March 2016
  • Source: VRBO, from HomeAway
Owner's Response: Aloha M Family! Thank you so very much for your time to post a review for us regarding the Wailea Sunset Bungalow. We are happy to hear that you had an outstanding vacation! This villa is exclusively managed and rented by Tropical Villa Vacations, a boutique locally owned and operated vacation rental management agency based on Maui. Your comments are very helpful to our staff, our business, the villa owner, and to potential future visitors who may be considering a holiday at the Bungalow. We appreciate your positive remarks and we look forward to welcoming you back again as a guest of Tropical Villa Vacations. With Lots of Aloha, The Tropical Villa Vacations Team
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  • 5 of 5

My wife and I stayed in the Bungalow for 5 days, and the place is amazing. The pictures are spot on. It is really very private, and the back yard is very large. The cottage is quaint, and in great condition. It is also well provisioned with everything needed, except groceries. It only has one bath, so I would not recommend it to a larger group, 4 people is probably max. The place is very appropriately named as the sunsets were fantastic. We took the lawn chairs right down to the water’s edge every night, and there was a small turtle swimming around the rocks every morning for coffee. When we were there, the two homes on either side were unoccupied, so it was absolutely quiet and practically private other than a few beach combers, or a passing kayak.

  • Review Submitted: 20/05/2015
  • Date of Stay: May 2015
  • Source: VRBO, from HomeAway
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Eden Prairie, MN


  • 5 of 5

My husband and I just spent 6 nights at the cottage and it was magical. The pictures are very accurate, the lawn is huge and the view is spectacular. We felt like we were all alone. At night we'd leave the windows open and the breeze came through the house beautifully- all you could hear was birds and waves. No traffic, garbage trucks, or people. The little cottage is so well equipped, they've thought of everything!!! As an example, there are 3 coffee makers so you have one that suits you! Its really amazing how well this place has been maintained. It is really worth the money. The beach in front of the cottage is rough with lava rocks everywhere and it is difficult to entry the water- but not impossible. About 50 yards to the right is beautiful Polo Beach. You can walk on the rocks or on the road- it's about a 2-3 min walk. On Polo beach you can swim and even rent chairs, kayaks, surf boards, etc. on the beach from the Kea Lani. You can also enter the Wailea Beach Walk at this point- which is a great morning stroll. We walked to the Kea Lani one night (3 mins tops) to pick up a pizza and bring it back to the beach house.....If you have a big group the adjacent house is also for rent from TVV and is BEAUTIFUL, new, and has a pool.

  • Review Submitted: 06/03/2011
  • Date of Stay: February 2011
  • Source: VRBO, from HomeAway
Owner's Response: Aloha Lola, Thank you for your review. We are so please you and your husband had such a special time at the Wailea Sunset Bungalow. It is a magical place in a perfect location. We look forward to welcoming you both back. Tropical Villa Vacations
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Nearest Airport
17.9 Miles
Kahului Airport (OGG)
Car: recommended

The Wailea Sunset Bungalow is a vintage oceanfront cottage at the edge of Wailea Resort with charming nostalgic ambiance reminiscent of Hawai`i of yester-year. Choose the Wailea Sunset Bungalow and experience seashore living as it was before the introduction of mega-mansions to our tropical island paradise. All new interior - just renovated and redecorated in winter 2016.


Rates & Availability

Contact Manager


  • Rates are subject to 4.166% GET & 10.25% TAT Hawaii Taxes. A reservation service fee of $125 is payable directly to Tropical Villa Vacations. These rates are valid as of the current date. Rates are subject to change until reserved with a signed Rental Application & Agreement and payment of the initial amount due.

    Infants and toddlers under two (2) years of age are not included in the total guest count. Toddlers and children age two (2) and above are included in the total guest count.

    Occupancy is granted for the maximum number of guests noted above. Excess occupancy is not allowed and may also be regulated by resort and/or local County of Maui ordinance.

    Just a few of the inclusive complimentary benefits provided are Personal Concierge Service, parking for the number of vehicles stated in the property highlights on-line, high speed internet, local phone calls, tropical bath treats, and personalized arrival greeting and orientation.

    Security deposit plus credit card guarantee is requested for this property, plus a separate incidentals deposit for guest requested special services. The security deposit may be reduced for repeat guests on subsequent visits.

    Out-cleaning is pre-collected with the final payment. The owner reserves the right to charge for out-cleaning in excess of the pre-collected amount, should the house be left in exceedingly messy condition. Respectful and average guest use is very much appreciated!

Manager's Cancellation Policy

  • No refunds for cancellations made after payment is made