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Houses Wailea

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86 houses

One-of-a-Kind Maui Getaway!

Wailea house

4 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 1 hour 47 minutes

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Price per night from

$1,650

Castaway Cove C201 at Wailea Beach Villas

Wailea house

3 bedrooms / 4 bathrooms / sleeps 6

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Price per night from

$1,395

Royal Ilima A201 Wailea Beach Villas

Wailea house

3 bedrooms / 4 bathrooms / sleeps 6

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Price per night from

$2,950

Wailea Sunset Estate

Wailea house

5 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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Price per night from

$4,150

Coral Gardens at Makena Bay

Wailea house

4 bedrooms / 4 bathrooms / sleeps 8

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$4,700

Sun Splash C301 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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$1,995

Bali Hai Pool Villa F102 at Wailea Beach Villas

Wailea house

3 bedrooms / 4 bathrooms / sleeps 6

“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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Price per night from

$1,595

Wailea Seashore Suite K507 at Wailea Beach Villas

Wailea house

3 bedrooms / 2 bathrooms / sleeps 6

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$1,195

Sandcastles Suite L509 Wailea Beach Villas

Wailea house

4 bedrooms / 3 bathrooms / sleeps 8

“Exceeded our expectations” This villa was the perfect accommodation for our family of 7 adults. The ocean view from the spacious and well equipped lanai was amazing. The beautiful furnishings, luxury finishing, and top of the line appliances, along with every amenity that it was equipped with, made this vacation such a pleasure. Truly special.

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$2,295

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

Wailea house

2 bedrooms / 2 bathrooms / sleeps 4

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$299

Beautiful Remodeled Ocean View Condo -Wailea Ekahi #22E

Wailea house

1 bedroom / 2 bathrooms / sleeps 4

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$369

Regal Mandalay M511 Wailea Beach Villas

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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$1,450

Oceanfront Location - Amazing Views - Kamaole Nalu #204

Wailea house

2 bedrooms / 2 bathrooms / sleeps 6

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$299

Beautiful Remodeled Beach Front 2 Bed. Unit-Royal Mauian #614

Wailea house

2 bedrooms / 2 bathrooms / sleeps 4

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$419

Lovely 1 Bdrm. Oceanfront Condo Wailea Elua #1601

Wailea house

1 bedroom / 2 bathrooms / sleeps 4

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$539

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

Wailea house

2 bedrooms / 2 bathrooms / sleeps 6

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$619

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$218

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Price per night from

$539

Luxury 2 Bedroom 2nd Floor Condo Wailea Elua #2204

Wailea house

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$709

Coco Palms Pool Villa D101 at Wailea Beach Villas

Wailea house

3 bedrooms / 4 bathrooms / sleeps 6

“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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$2,950

Spectacular Ground Floor Unit - Wailea Grand Champions #173

Wailea house

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$210

Spectacular Ocean View With Remodeled Interior -Mana Kai Maui Resort #812C

Wailea house

2 bedrooms / 2 bathrooms / sleeps 6

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$629

Beautiful Remodeled Beach Front 2 Bed. Unit-Royal Mauian #512

Wailea house

2 bedrooms / 2 bathrooms / sleeps 4

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$439

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$339

Stunning Ground Floor -2 Bedroom 2 Bath Condo- Royal Mauian #104

Wailea house

2 bedrooms / 2 bathrooms / sleeps 4

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$409

Beautiful 1 Bdrm Ocean Front Condo-Wailea Elua #1602

Wailea house

1 bedroom / 2 bathrooms / sleeps 4

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$539

Wailea Sunset Bungalow

Wailea house

2 bedrooms / 1 bathroom / sleeps 4

“Paradise at Wailea Sunset Bungalow” Our trip to Maui was fantastic, mostly due to the spectacular Wailea Sunset Bungalow. This home was stocked with absolutely everything a person or group could ever need for a week, even a month. We enjoyed the famous Maui sunsets each night from this oceanfront gem of a property. We enjoyed breakfast every morning outside on the private deck with hot tub, looking out onto the ocean from our own personal paradise. The booking was seamless, the people at Tropical Villa Vacations even called to alert us to possible weather and just to make sure everything was ok with the rental. We will definitely be back, the Wailea Sunset Bungalow made our trip perfect.

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$1,395

Luxury At Its Finest at Wailea Elua Village # 1508

Wailea house

2 bedrooms / 2 bathrooms / sleeps 6

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$569

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

Wailea house

2 bedrooms / 2 bathrooms / sleeps 6

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$569

Spacious Ground Floor 2 BDRM Condo - Wailea Elua #107

Wailea house

2 bedrooms / 2 bathrooms / sleeps 4

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$619

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$999

Great rentals within 20 miles that match your search

Launiupoko, Private Luxury Home "Kalapana"

Lahaina house

3 bedrooms / 4 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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$1,465

ELEGANT BEACH HOME POOL & VIEW PERFECT LOCATION

Kihei house

3 bedrooms / 4 bathrooms / sleeps 6

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$4,140

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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$5,503

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!

Responds fast! avg. 3 hours 56 minutes

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Price per night from

$284

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

Kihei house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 35 minutes

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Price per night from

$1,534

Charming 2bd-1ba Downstairs Unit

Paia house

2 bedrooms / 1 bathroom / sleeps 4

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$294

80 Series Land Cruiser Roof Top Tent RTT rental in Maui

Kihei house

1 bedroom / 2 bathrooms / sleeps 2

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Price per night from

$182

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