Houses Wailea

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OCEAN VIEW LUXURY, CASTAWAY COVE C201, WAILEA BEACH VILLAS!

Wailea house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

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$1,025

FUN IN THE SUN LUXURY AT SUN SPLASH C301 AT WAILEA BEACH VILLAS!

Wailea house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

“Very Impressive and I am hard to impress!!” Our stay at the Wailea Beach Villas was absolutely amazing! A typical vacation for us in the last few years has been atlantis Royal Towers Bahamas, Westins ,Fairmonts and Grand California resort at Disneyland. Sun Splash is elegantly appointed, comfortable and immaculate, with large spacious rooms. Better than the pictures on the website. Views from the lanai are breathtaking with wonderful sunsets. Staff and service was warm and professional. Literally steps away from shops and restaurants. Well stocked kitchen for formal or informal dining, except for food of coarse.

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$2,650

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$1,995

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$1,299

SOUTH MAUI'S SPECTACULAR OCEANFRONT WAILEA SUNSET ESTATE WELCOMES YOU!

Wailea house

  • 4 bedrooms
  • 6 bathrooms
  • sleeps 8

“Truly Spectacular” This house is nothing short of spectacular. We chose this home for a family get-together and it worked perfectly. The Master Suite gave my husband and me the privacy we wanted, while our children and grandchildren had their own privacy. Each bedroom has its own bath. Everything was provided and ready for us upon arrival. We had T-times for golf, paddle boards, sea kayaks, snorkeling gear, as well as high chairs and cribs. Nothing was overlooked. We even took the opportunity to have a private chef (highly recommend just for the experience) cook dinner four different evenings, as well as adding on some additional cleaning. The sunsets were beautiful, the whales were breeching and the turtles surfed up to the rocky beach every night. Because of a tropical storm, we were able to watch professional surfers from our chairs on the grass. The larger hotels are within walking distance, but other than using the Spa facility at the Four Seasons, we felt no reason to leave this beautiful property. The management of Tropical Villa Vacations were extremely professional and easy to work with. For a group I would highly recommend this home. Everyone in our family had such a relaxing get-away that we plan to make this a bi-annual vacation and can't wait for 2016. There is nothing better than spending quality time with family, and this is the house to spend it in...truly spectacular!

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$2,295

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$850

“The unit far exceeded out epectations!!” Th villa was as beautiful as presented on line. Very spacious and , well appointed. The kitchen featured high end appliances not normally seen in rental units. Beautiful decor. The owner has clearly put a lot of thought and resources into the comfort of his guests, right down to a fully stocked executive bar to every kitchen gadget you could possibly think of!!! The location was perfect. The unit was strategically located between the adults only and family pools... just s two minute walk to the beach. The concierge and rental agents were a pleasure to deal with and usually responded to any request within a hour. Great unit! Great experience!

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$1,195

Stunning Views- Renovated 2 Bedroom Condo- WAILEA ELUA, #2202

Wailea house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$549

Ocean Views -Remodeled Top Floor 2bd/2ba Condo - Kamaole Nalu #603

Wailea house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$349

REGAL MANDALAY M511 AT WAILEA BEACH VILLAS! TOP FLOOR OCEAN VIEWS!

Wailea house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Wonderful place to stay” This was our second time in renting from Tropical Villa Vacations. They are always helpful with anything that we have asked. They had boogie boards ready for the boys at our condo when we arrived and they also found a place for us to have Easter Brunch and made the reservations for us. The home was great for our family of 5. It had everything that we could have asked for and much more. My youngest's favortie part was that the balcony looked over the pool. He would stand out there every night and wait for the other people to leave and as soon as they did we headed down and had it all to ourselves. There was a great coffee stand just outside the properties gates. It was fun to walk on the pathway between all the other resorts to check out what they had but we still liked ours the best. More private and quiet. We loved having our own parking space in the garage with direct access to our elevator to our Villa. We didn't spend a whole lot of time on the beach there but it was clean and very nice to have someone come and set up a chair for you with towels. The waves were pretty mild for smaller children or less daring folks. Our boys preferred the bigger waves so we spent time at other beaches. I would recommend staying here to anyone. The facilities were well taken care of and staff were very friendly and helpful if you needed anything.

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$1,099

Lovely 1 Bdrm. Oceanfront Condo Wailea Elua #1601

Wailea house

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

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$569

Oceanfront Location - Amazing Views - Kamaole Nalu #204

Wailea house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$339

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$639

ULTRA LUXURY SOLARA LUXE POOL VILLA D101, NEWLY RENOVATED, SLEEPS 8!

Wailea house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

“Even more beautiful than the pictures.” We highly recommend Tropical Villa Vacations. Irene helped us find the perfect spot for our vaction. D101 is a beautiful addition to their inventory. The unit is spectacular. The Wailea Beach Villas property is a perfect spot for anyone looking for a luxurious condo in the heart of Wailea. Beautiful property, great ocean views and top notch service from a team that truly cares about your vacation experience!

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$1,795

Beautiful Ground Floor 2 Bed/2 bath - WAILEA ELUA, #1509

Wailea house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$599

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$499

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$329

Spectacular Ground Floor 2 Bedroom Condo Wailea Elua #305

Wailea house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$509

Beautiful 1 Bdrm Ocean Front Condo-Wailea Elua #1602

Wailea house

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

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$569

OCEANFRONT WAILEA SUNSET BUNGALOW, HOT TUB, LARGE YARD!

Wailea house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“Marvelous ocean front experience!” We stayed for 12 nights at the Wailea Sunset Bungalow. It was a tremendous way to celebrate our 35th wedding anniversary. The views were fabulous and the bungalow was everything we could have wanted and more. Due to dietary restrictions we needed to prepare our own meals, and the full kitchen allowed us to do so very comfortably. Being right on the water we saw breaching whales every single day we were there! We loved the separation from the usual crowds, yet we were close enough to resorts not to feel too isolated. Property manager and concierge were very responsive to our needs and helped to make everything perfect for our vacation. The bungalow was as advertised. There were no surprises. Everything was as we expected. We have stayed at many upscale hotels on several of the islands, but this by far was our best experience staying in Hawaii. Most importantly, we would stay here again in a heartbeat! We can't wait to come back.

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$895

Luxury At Its Finest at Wailea Elua Village # 1508

Wailea house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$729

Stunning Ground Floor 2 Bedroom Wailea Elua #307

Wailea house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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$499

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$449

Spacious Ground Floor 2 BDRM Condo - Wailea Elua #107

Wailea house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$779

Prime Oceanfront 1Bd/1Ba Condo WAILEA ELUA, #1302

Wailea house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$749

Great rentals within 20 miles that match your search

Launiupoko, Private Luxury Home "Kalapana"

Lahaina house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Beautiful Home” The setting and view is spectacular. All the rooms were very nice. We enjoyed the pool table upstairs, although be careful as there is a flaw in the slate and the cue ball can go flying! The Sonos music system is also great. The backyard is perfect. Lots of pool toys. We enjoyed the evenings watching the stars. We did have a few minor issues. We had 3 adult couples and it wasn't clear that two of the bedrooms had a shared bath. The other bath was across the hall. We had expected private baths for each bedroom. The showers are beautiful but water pressure is minimal. Lastly, it seems that pool and hot tub controls are managed by the owner down below. The pool light would turn off and if you wanted to swim late, we couldn't find a pool light switch. Lastly, we didn't have heat in the hot tub the first day/night and requested help from the owner. No response. The pool maintenance person fixed it for us the next day. Even with these minor issues, I would recommend the home again. It is beautiful and has stunning views. We enjoyed the fruit trees, too.

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$1,592

Eco-Friendly Condo Located in the Heart of Kihei

Kihei house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Well equipped and maintained, comfortable and easy access to beach, food and shopping.” This was my second stay at this lovely 1 BR condo in Kihei and I enjoyed it even more. The location is great, just across S Kihei Rd from the beach at the north end of Kamaole Beach #1. You can walk on the beach all the way to Ulua Beach if you want. The place is amazingly well equipped. All you need to cook and toys for the beach. This time, I even discovered two yoga mats in covers and two yoga blocks to go with them. Perfect for home yoga or taking them to the beach yoga classes that sometime happen. It is also possible to walk to good food and even the grocery store. The building has a great pool for afternoon cooling and laundry facilities are available on site. There is a bit of a view of the ocean from the lanai, but the general vista of palm trees and tropical vegetation in the neighboring buildings was quite nice. Never used the AC, screens and fans kept things comfortable. Finally the electronics were great, big screen and lots of music and video service choices.

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$509

South Maui 4 bdrm close to beaches, restaurants

Kihei house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

“Exceptional home away from home!” Just as described, the kihei oasis is an excellent vacation rental. The layout of the home, furnitionings and it's convenient surroundings, I would definitely recommend staying here. The jacuzzi was a hit, but the real bonus was the little amenities that you don't really think of until you need it. I opened the kitchen cabinets and found foil, oil, shoyu sauce and lots of helpful seasonings. The bathroom cabinets also had additional body wash, shampoo, lotion and for kids too. Although we brought our own amenities, I'm glad you have them available especially for large families. Also a garage wall dedicated to fun in the sun activities, boardgames and so much more. Mahalo to the Morts ohana for providing such a lovely home away from home, We definitely enjoyed ourselves!

Responds fast! avg. 40 minutes

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$1,031

ELEGANT BEACH HOME POOL & VIEW PERFECT LOCATION

Kihei house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

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$4,403

LUXURY BEACH HOME POOL EXCELLENT LOCATION

Kihei house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“Wonderful stay in the perfect home. Great golf and beach locatio” My friends and I stayed in this high-end well-appointed home while we were on Maui. Our main purpose was to fit in as many games of golf as possible as our wives shopped and relaxed by the pools and enjoyed the beaches. This plan worked out perfectly since we were located right on golf course and a short walk from the beach. Everyone was more than happy with our accommodations and being able to rent a spacious home in the center of a luxury resort was ideal. This home was an exceptional value when you consider that most of the hotel rooms in the Wailea/Kihei area go for the same price for just one room. Everyone in our group felt as though this was our own home in Maui and we expect we will return again as soon as we can. We highly recommend this place and would like to thank the owners for extending us their every kindness. Sincerely, Don M

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$5,548

Amazing House w/ Pool, Cabana & More Kihei Wailea

Kihei house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

“Best family holiday we have had in ages” This is a really lovely place. The pool area and cabana are private and very user friendly. Beach in the morning and sheltered pool area in the afternoon, ideal with 3 teenagers. Bedrooms are spacious and everything works. We didn't bother with a/c just opened the house up and used the ceiling fans. Plenty of living space and room for people to do their own thing if they wanted to. Close to most things but far enough away from noise and crowds. It helps that Maui is absolutely brilliant. Andrew leaves you alone but is readily available to help with any minor issues. The kids said it was the best family holiday they have been on in ages. We agree.

Responds fast! avg. 3 hours 58 minutes

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$1,431

Sacred Garden Retreat—Unique Log House on Maui!

Makawao house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

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$1,117

Haiku, Maui Vacation Rental-Bamboo Valley Inn

Haiku house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“Family Vacation Paradise” We had our second family vacation stay in the Haleakala Suite and loved it! Tom and Vicki's attention to detail made our vacation so easy and enjoyable. We love the beautiful surroundings, furnishings, and serene atmosphere away from the bustling tourist areas. Yet it's still only a short drive to the beach and excellent restaurants like Mama's Fish House and Hali'imaile General Store. We also spent mornings and evenings in making our own breakfasts and grilling dinners on the patio. The kitchen had everything we needed to make nice home-cooked meals. We made good use of the beach supplies like the cooler, beach towels, and sand bucket. :) Our time at Bamboo Valley Inn was cherished time - especially our daughter getting to visit Tom and Vicki's horse each morning. We're sure this will be a fond memory for her, and we plan to visit again as often as we can. Don't miss out on this gem of a vacation home!

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$344

Kamaole Villa Maui County Conditional Permit 2003/0009

Kihei house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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$2,519

Milo Cottage

Paia house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 7

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$974

"WOW IT'S LIKE OUR OWN PRIVATE RESORT!"... recent guest.

Kihei house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 3 hours 30 minutes

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$1,821

Luxurious and Private Maui Home with Swimming Pool

Haiku house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Serenity in Maui” My husband and I spent eight days at this lovely property, and quite simply, was the best house rental, and the best vacation we have ever taken. There are not enough words to tell you how beautiful the home is with all the stunning landscaping, yummy fruit trees,and great, private saltwater pool. The home is immaculate, and luxurious. Extremely clean, and absolutely stunning. Very comfortably furniture and great beds. Claudia, the owner is charming, and will be there when you need her for anything. Please, do yourself a favor and stay in this home. It is paradise!

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$1,031

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Price per night from

$606

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