Vacation Rentals & Condos in Wailea

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111 condos

Wailea Ekahi Ocean View 50A

Wailea condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

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$396

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$253

Gorgeous Remodeled Ocean Front Condo - Makena Surf Resort G-206

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$999

Maui Rendezvous Wailea Ekahi 33A Luxury Resort, Beach-3 min walk, Remodeled

Wailea apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 5

“Relaxing and Beautiful Getaway” My husband and I stayed at 33a in Ekahi for a week long vacation. The condo and surroundings exceeded all of our expectations. It is very tastefully decorated, extremely clean with all the amenities needed for a relaxing getaway. The grounds, pool area and beach are wonderful. The lanai is a serene retreat. We ate all of our breakfasts and lunches out there and then dined on fantastic food for dinner from the many choices of restaurants. The keyless entry and parking were very convenient. We will return next summer with our children.

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$431

Upgraded Unit w/ Beautiful Ocean Views Makena Surf Resort # C-103

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Wonderful week in paradise!” The staff at ali'i Resorts is fantastic and helped us to plan fun adventures for our family throughout our stay. The housekeeping staff was attentitive and worked hard each day to help make our stay great. The property and condo were both very well maintained and beautiful- with spectacular views throughout. One of our favorite features was the patio and the amazing view that we enjoyed while dining outdoors. The beach access was convenient, just a short walk down a paved path to the beach that offered kid friendly boogie boarding waves and rock outcropings for snorkeling. We have stayed in a few of the luxury hotels in Wailea and prefer the relaxed environment of Makena Surf.

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$530

SPECIAL SPRING RATE FOR AN "ALOHA" OCEAN VIEW AT MAUI KAMAOLE G-212

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$316

Upgraded Unit w/ Beautiful Ocean Views -MAKENA SURF RESORT, #F-107

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$1,202

Luxurious Oceanfront Corner Unit SURF RESORT, #F-212

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Amazing and Beautiful” Loved staying at this condo. Great accommodations, great services and support staff. The only odd thing was the power kept going out in the master bedroom/bathroom. Other than that, it was a 10!

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$871

Fantastic Location - Beautiful Condo -Makena Surf Resorts # G-204

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“Maui memories” We were excited to be coming back back to Makena Surf after staying there two years ago and being so impressed with the unit and the beautiful surroundings back then. We were somewhat fearful that we could even come close to matching that same experience this time around, but this unit exceeded our expectations. We will be back in the near future.

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$701

Beautiful Beach Front Luxury Corner Unit MAKENA SURF RESORT, #E-206

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Fantastic Stay at Makena Surf” We would definitely return to this property, if not exact condo, at Maken Surf. Great location and ideal building on the big beach.Make sure you see the development plan so you pick the right building - it's worth being beachfront. And when the west coast was in the clouds, we were always sunny. Lovely beach, quiet with just the right amount of action close by. Easy drive to area shops and restaurants. Condo was ideal and services were terrific. If you are looking for beach and pool bar, resort services - this is not your place. There is a beach and pool but no blended drinks being served. But you'll spend three times the money for a hotel room versus having the luxury of spreading out at "home" with your family for meals, movie night and morning breakfast on the lanai. A much nicer way to go and then eat dinner in all the great restaurants. Who wants to shower and dress for breakfast anyway? I'd rather eat on the lanai and relax. The condo has everything you would want for a lovely stay from good bedding, spacious bathrooms,beach chairs, daily maid service, to streaming Netflix and fully stocked kitchen. Rent a car and you are all set.You won't want to leave and you feel more like you live there rather than just being another tourist. Oh and having a washer dryer in the unit was super convenient. Overall... a lovely spot.

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$801

Beautiful Beach Front 2 BDRM Condo - Makena Surf Resort # B-304

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Exquisite view, lovely appointments, needs new bed!” The good news: we only left this beautiful condo to jump into the water (in the ocean or the lovely pool), to go to yoga or for jogs, to get supplies or go out to eat! The view is stunning, the lanai couldn't be any closer to the water, has comfortable patio furniture and you have all the comforts of home. The kitchen and bathrooms are luxuriously appointed. After a slight confusion when we landed at the Kahului airport, we were even able to check in early on our arrival day. The only bad news, and the reason we couldn't give it five stars is the mattress in the master bedroom needs replacing. There are two huge, deep divots in the too-soft, too worn mattress. I hope that will be replaced soon, because when we come back to Makena Surf, we will definitely stay here. We've stayed in two other condos on the property, and this was the best!

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$801

Gorgeous Beach Front Condo MAKENA SURF RESORT, #E-202

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$721

Fully Remodeled Oceanfront Condo MAKENA SURF RESORT, #F-202

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$601

3 Bedroom Beach Front Paradise at Makena Surf - MAKENA SURF RESORT, #G-304

Wailea apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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$1,002

Fantastic Location - Beautiful Beach Front Condo -Makena Surf # B-207

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$949

Beautiful Golf & Ocean Views - WAILEA GRAND CHAMPION #148

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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$230

Lovely Ground Floor Unit MAKENA SURF RESORT, #C-102

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$641

Wailea Ekolu 2/2 - Elegant, Spacious, Modern, Ocean View!

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$446

Wailea Ekahi Village Relaxing Ocean and Mountain Views

Wailea condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

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$327

Renovated Studio Steps from the Beach & Pool - A/C

Wailea apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$228

Stunning Condo on the Golf Course - WAILEA GRAND CHAMPION #90

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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$300

Renovated 1BR at Maui Banyan - Pool, Hot Tub, A/C

Wailea apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$286

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$689

K B M Resorts: Wailea Elua Village WEV-2103, Spacious 2 Bedrooms with Ocean

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$567

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$689

Stunning Golf Course & Garden Views - WAILEA GRAND CHAMPION #142

Wailea condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

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$220

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$496

Great rentals within 20 miles that match your search

Upscale Furnishings, Gorgeous Lawns For Kids

Kihei condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

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$218

606 Hale Pau Hana Beachfront, Phenomenal Views

Kihei condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

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$517

“Perfect Stay in Paradise!” Tracy's condo was perfect for our 30th wedding anniversary stay! We would not stay anywhere else on Maui except in one of Tracy's amazing rentals! The condo has a great location (across from the beach) and close to restaurants and shops. It is brightly decorated with happy cheerful colors and special touches! It was like a ray of sunshine! Both my husband and I loved the fact that the condo was well supplied --- everything from shampoo to an ice cooler and more. Tracy has thought of everything you need for a terrific stay --- even electric candles! The bed was so comfortable and relaxing! Tracy's binder on the coffee table was full of tips for a great vacation as well as menus from area restaurants. We loved seeing the large sea turtles swimming in the lagoon section at the beach across the street. The property is extremely clean and well maintained and we enjoyed the pool and jacuzzi at the condo as well. We were sorry to leave and return home. We can't wait to return to stay again at one of Tracy's Tropical Treasures condos! We enjoyed it so much that I have recommended it to a recently engaged friend for her honeymoon. Thank you Tracy for providing such wonderful accommodations and making our 30th wedding anniversary so memorable! We will definitely be back!

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$332

SPECIAL! Closest to beach! King Bed

Kihei condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$281

"Kihei Akahi D-211: Ocean View, Opposite Kamaole Beach, Remodeled"

Kihei condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$259

Remodeled condo across from beautiful Kam 1 beach!

Kihei condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$345

KAMAOLE SANDS BLDG 4 - OCEAN CLOSE - LARGE LANAI

Kihei condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

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$201

Gorgeous*Peaceful*Condo*Steps to Beautiful Beach

Kihei condo

  • 1 bedroom
  • 3 bathrooms
  • sleeps 4

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$343

Terrific Ocean View Penthouse Suite!

Kihei condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$230

Exceptional,Ocean View,Beautiful New Kitchen& Bath

Kihei condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$343

Oceanview Fabulous 2 Bedroom Condo,Great Location

Kihei apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“A wonderful, relaxing place to stay in Maui” Just what we wanted! The place is very convenient, and has the amenities needed for a relaxing beach vacation, including beach chairs & mats, towels, boogie boards etc. Parking is a breeze, and it's close to the bus line as well. The well equipped kitchen inspired us to eat in most evenings. I would recommend to my friends as family.

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$275

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