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67 vacation rentals

(5) Excellent 

28

One-of-a-Kind Maui Getaway!

Maui / Wailea

Wailea house

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool

Price per night from

$1,340

Responds fast!
avg. 1 hour 43 minutes

Price per night from

$1,340

(12) Excellent 

22

Updated Spacious 3 Bdrm. Wailea Ocean View Condo

Maui / Wailea

Wailea apartment

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“Great condo!” We absolutely loved the condo.  It was well appointed and spacious.  We hosted a gathering of about 20 people and the kitchen, dining, living spaces combined with the lanai comfortably held that many people. The location was perfect, ri
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Price per night from

$285

Responds fast!
avg. 3 hours 8 minutes

Price per night from

$285

(16) Excellent 

17

Wailea Ekahi Ocean View 50A

Maui / Wailea

Wailea condo

1 4 5 nights min

  • 1 bedroom
  • sleeps 4
  • 5 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$220

Price per night from

$220

33

New Listing! Breathtaking Ocean Views from 3rd Row Luxury Villa at Ho'olei

Maui / Wailea

Wailea villa

3 8 6 nights min

  • 3 bedrooms
  • sleeps 8
  • 6 nights min
  • Child Friendly

Price per night from

$695

Responds fast!
avg. 3 hours 48 minutes

Price per night from

$695

(8) Excellent 

31

The Perfect Location for a Relaxing Hawaiian Getaway - Grand Champions #103

Maui / Wailea

Wailea apartment

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“This is a beautiful condo, wonderfully maintained, in a great lo” We have stayed at many condos on Maui for years, and this is absolutely our favorite. We were lucky enough to be the first guests, and everything was even better than expected. The pho
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Price per night from

$169

Responds fast!
avg. 1 hour 28 minutes

Price per night from

$169

(3) Excellent 

14

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

Maui / Wailea

Wailea condo

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$261

Price per night from

$261

22

Ho'Olei Largest Floor Plan - Ocean and Pool Views

Maui / Wailea

Wailea house

3 7 3 nights min

  • 3 bedrooms
  • sleeps 7
  • 3 nights min
  • Beach / lakeside relaxation
  • Child Friendly

Price per night from

$1,547

Price per night from

$1,547

(14) Excellent 

24

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

Maui / Wailea

Wailea apartment

1 5 4 nights min

  • 1 bedroom
  • sleeps 5
  • 4 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“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 relaxin
…see more

Price per night from

$315

Price per night from

$315

(37) Excellent 

18

Wailea Ekahi 7G Luxury Ocean Front S Maui Condo

Maui / Wailea

Wailea apartment

1 3 7 nights min

  • 1 bedroom
  • sleeps 3
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
“Absolutely Perfect!” This condo is gorgeous, and set up with everything you could ask for during your stay. We were so pleased with the location, cleanliness, and the setup of the home for us. There was not a single thing that we came across that we
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Price per night from

$350

Responds fast!
avg. 2 hours 41 minutes

Price per night from

$350

(3) Excellent 

24

LUXURY FOR LESS! Best value in Hoolei Wailea!

Maui / Wailea

Wailea villa

3 8 5 nights min

  • 3 bedrooms
  • sleeps 8
  • 5 nights min
  • Child Friendly

Price per night from

$1,100

Price per night from

$1,100

(5) Very Good 

82

Outstanding Luxury Condo for Couples in Paradise - Ocean and Beacfront

Maui / Wailea

Wailea apartment

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.8 mi
  • Swimming pool

Price per night from

$250

Responds fast!
avg. 3 hours 54 minutes

Price per night from

$250

24

Romantic, Elegant, Sensual Retreat

Maui / Wailea

Wailea condo

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Beach / lakeside relaxation

Price per night from

$245

Price per night from

$245

33

Renovated Maui Banyan Complex; Walk to Kam II Beach; Modern Kitchen!

Maui / Wailea

Wailea condo

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly

Price per night from

$179

Price per night from

$179

(1) Excellent 

23

Sweeping Ocean Views; Private High End Condo!

Maui / Wailea

Wailea condo

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Air conditioning

Price per night from

$209

Price per night from

$209

21

The Palms at Wailea 901 - Luxury Privacy & Beaches

Maui / Wailea

Wailea condo

1 4 4 nights min

  • 1 bedroom
  • sleeps 4
  • 4 nights min
  • Beach / lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool

Price per night from

$190

Price per night from

$190

17

Exceptional Ocean View; Great Kihei Location; Walk To Beach & Restaurants!

Maui / Wailea

Wailea condo

1 3 4 nights min

  • 1 bedroom
  • sleeps 3
  • 4 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$145

Price per night from

$145

(13) Excellent 

24

Wailea Luxurious Beachfront 2br,2ba on Polo Beach

Maui / Wailea

Wailea apartment

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“Oceanfront Luxury on Polo Beach” This was our second stay at this meticulously detailed, ocean front luxury home. Every amenity has been considered and provided by the owners, to ensure their guests experience executive living while in Maui. The di
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Price per night from

$659

Price per night from

$659

(1) Excellent 

25

Beautiful Ocean View 2BR/2Bath

Maui / Wailea

Wailea condo

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 mi
  • Swimming pool

Price per night from

$441

Price per night from

$441

21

Kihei Akahi Resort - Unit C505

Maui / Wailea

Wailea condo

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$186

Responds fast!
avg. 2 hours 33 minutes

Price per night from

$186

28

Keawakapu Beachfront Living....right on the beach

Maui / Wailea

Wailea condo

2 6 1 night min

  • 2 bedrooms
  • sleeps 6
  • 1 night min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$450

Price per night from

$450

(2) Excellent 

39

~BEAUTIFULLY APPOINTED, RENOVATED, 5-STAR WAILEA VILLA~

Maui / Wailea

Wailea villa

2 4 5 nights min

  • 2 bedrooms
  • sleeps 4
  • 5 nights min
  • Nearest beach 1 mi
  • Swimming pool
  • Child Friendly

Price per night from

$195

Price per night from

$195

(6) Very Good 

36

PRIMO OCEAN VIEW / SOUND JUST STEPS TO MALUAKA BEACH MAKENA HOUSE South Maui HI

Maui / Wailea

Wailea house

2 4 14 nights min

  • 2 bedrooms
  • sleeps 4
  • 14 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Car not necessary
“beautiful views in south Maui” We had a wonderful stay in South Maui. The house has a beautiful garden and we spent much of our time on the lanai enjoying the view and peace. The house is fully equipped with everything we needed, including beach gea
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Price per night from

$299

Price per night from

$299

18

Wailea Beach House--Golf, Tennis, Beach--Short walk, Shopping and Dinning

Maui / Wailea

Wailea apartment

2 6 3 nights min

  • 2 bedrooms
  • sleeps 6
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$225

Price per night from

$225

20

Ekahi Ocean Studio, 300 feet to Keawakapu Beach

Maui / Wailea

Wailea studio

Studio 2 3 nights min

  • Studio
  • sleeps 2
  • 3 nights min
  • Swimming pool
  • Air conditioning

Price per night from

$245

Price per night from

$245

24

Incredible Ocean Views & Beautifully Remoded - Close to Ulua Beach

Maui / Wailea

Wailea condo

1 2 5 nights min

  • 1 bedroom
  • sleeps 2
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool

Price per night from

$449

Price per night from

$449

21

Ocean View, Fully Remodeled luxury Condo 2 minute walk to the beach.

Maui / Wailea

Wailea condo

1 4 4 nights min

  • 1 bedroom
  • sleeps 4
  • 4 nights min
  • Child Friendly

Price per night from

$260

Price per night from

$260

22

Grand Champions 033

Maui / Wailea

Wailea apartment

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$496

Responds fast!
avg. 2 hours 46 minutes

Price per night from

$496

45

Kihei Akahi Resort - Unit B204

Maui / Wailea

Wailea condo

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$251

Responds fast!
avg. 2 hours 22 minutes

Price per night from

$251

37

Kihei Akahi Resort - Unit C405

Maui / Wailea

Wailea condo

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$186

Responds fast!
avg. 3 hours 13 minutes

Price per night from

$186

16

Intimate Tropical Retreat

Maui / Wailea

Wailea apartment

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Air conditioning

Price per night from

$401

Price per night from

$401

20

South Kihei Paradise & Great Location

Maui / Wailea

Wailea condo

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 0 mi
  • Swimming pool
  • Child Friendly

Price per night from

$159

Responds fast!
avg. 3 hours 5 minutes

Price per night from

$159

(101) Excellent 

42

Aloha Kai Suite at Wailea Beach Villas PH 205

Maui / Wailea

Wailea villa

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“Best Vacation” My family and I truly enjoyed loved our stay at Aloha Kai Suite and the Wailea Beach Villas. Beautifully decorated, clean, kitchen had everything you needed, and of course the view was amazing. We loved being so close the sandy beach, t
…see more

Price per night from

$995

Price per night from

$995

Great rentals within 20 miles that match your search

Distance approx 3.98 km from Wailea Show on Map

(2) Excellent 

12

Sunset Suite - steps to the ocean

Maui / Kihei

Kihei apartment

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.2 mi
  • Air conditioning

Price per night from

$129

Responds fast!
avg. 2 hours 6 minutes

Price per night from

$129

Distance approx 15.59 km from Wailea

(1) Excellent 

45

Spreckelsville Paia Vacation Home near Baby Beach

Maui / Spreckelsville

Spreckelsville house

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Nearest beach 0.5 mi
  • Child Friendly
  • Private garden

Price per night from

$500

Responds fast!
avg. 3 hours 8 minutes

Price per night from

$500

Distance approx 15.51 km from Wailea

40

5C Sugar Cove, beachfront Spreckelsville, Paia

Maui / Paia

Paia condo

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.5 mi
  • Swimming pool

Price per night from

$600

Responds fast!
avg. 3 hours 8 minutes

Price per night from

$600

Distance approx 5.96 km from Wailea Show on Map

35

Kihei Holiday Unit #120

Maui / Kihei

Kihei condo

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$225

Responds fast!
avg. 2 hours 46 minutes

Price per night from

$225

Distance approx 8.63 km from Wailea

26

Maalaea Kai 408

Maui / Maalaea

Maalaea condo

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$400

Responds fast!
avg. 2 hours 46 minutes

Price per night from

$400

Distance approx 0.1 km from Wailea Show on Map

(3) Very Good 

51

WAILEA EKOLU 702 / Panoramic Ocean Views from Living Room, Lanai & Master Bdrm!

Maui / Kihei

Kihei condo

2 6 4 nights min

  • 2 bedrooms
  • sleeps 6
  • 4 nights min
  • Nearest beach 1 mi
  • Swimming pool
  • Child Friendly

Price per night from

$375

Price per night from

$375