Vacation Rentals with Hot Tub in Wailea

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703 vacation rentals

(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

$286

Responds fast!
avg. 3 hours 8 minutes

Price per night from

$286

(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

$1,342

Responds fast!
avg. 1 hour 43 minutes

Price per night from

$1,342

(3) Excellent 

47

Grand Champions #151 is a1 Bd 2 Ba fronting the Wailea Golf Course. Sleeps 4.

Maui / Wailea

Wailea apartment

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Exceeded Expectations” I love this property. We had looked at alot of places and time was running out. When this property popped up, I never thought it looked liked the way it did in person. It looked better in person. We are definitely returning. Mah
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Price per night from

$160

Responds fast!
avg. 5 minutes

Price per night from

$160

(14) Very Good 

30

Grand Champions #51 is a 2Bd 2Ba is a large condo that sleeps 6. Great Rates!

Maui / Wailea

Wailea apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Exceeded expectations by a mile!” From the moment we arrived we were amazed at the way the condos we rented (we had #48 as well) were decorated, furnished and stocked with anything we could possibly have wanted for our holiday. Even items for the beac
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Price per night from

$211

Responds fast!
avg. 5 minutes

Price per night from

$211

(15) Very Good 

49

Palms at Wailea Unit #2305 1Bd/2Ba Quiet, Very Private! Near Beach, Sleeps 2

Maui / Wailea

Wailea apartment

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Swimming pool
  • Child Friendly
“Great for Couples” For those of us who hate living in hotels, or paying for services we don't use, this 1 bedroom/2 bathroom condo is perfect. It feels and looks even larger than the photos and is equipped with a full kitchen, that is very well stocke
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Price per night from

$190

Responds fast!
avg. 5 minutes

Price per night from

$190

(6) Excellent 

21

Wailea Orchid Villa - Panoramic Views! 3 Bd/3 Ba

Maui / Wailea

Wailea villa

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 mi
  • Swimming pool
“Wonderful stay in the Penthouse Villa...” Service: 5 Stars - The owner was very prompt in replying to email with questions, concerns. Concierge and front desk staff were courteous and very helpful. The bellman/staff even brought all of our luggage
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Price per night from

$1,052

Responds fast!
avg. 2 hours 39 minutes

Price per night from

$1,052

(19) Excellent 

32

Palms at Wailea #1105 Lovely Ocean View, 2Bd 2Bath, Great Rates! Sleeps 4

Maui / Wailea

Wailea apartment

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child Friendly
“Great Getaway!!” I loved unit 1105 at The Palms. It was totally updated and very clean. The beach chairs and boogie boards were nice to have. Loved the quiet nature of the Palms and the proximity to all of the beautiful beaches!!
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Price per night from

$300

Responds fast!
avg. 5 minutes

Price per night from

$300

(1) Very Good 

38

Palms at Wailea #1102 Probably the best ocean view at the Palms at Wailea!

Maui / Wailea

Wailea apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
“Great place to stay for the price” We loved the location and views from our units. The pool was warm and quite nice despite having many restrictions. The units were clean and nice looking however many of the amenities promised (ie. beach equipment) we
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Price per night from

$296

Responds fast!
avg. 5 minutes

Price per night from

$296

(31) Very Good 

34

Grand Champions #48 is a 2bd 2ba Ocean View condo that Sleeps 6 Great Rates!

Maui / Wailea

Wailea apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Best experience ever in USA. Loved every minute of our stay.” #51 @ #48 condos were by far even better than the reviews and pictures described. My family from Canada and myself were truly impressed by the attention to detail and how well the units wer
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Price per night from

$221

Responds fast!
avg. 5 minutes

Price per night from

$221

26

Palms at Wailea #205, 2Bd/2Ba, Luxurious, Spacious, Fantastic Location!

Maui / Wailea

Wailea apartment

2 6 min stay varies

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

Price per night from

$290

Responds fast!
avg. 5 minutes

Price per night from

$290

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

$696

Responds fast!
avg. 3 hours 48 minutes

Price per night from

$696

(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

(20) Very Good 

27

Palms at Wailea #1902 Garden View 2Bd/2Ba, Fully Air Conditioned, Sleeps 6

Maui / Wailea

Wailea apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning
“A breath of fresh air” I have stayed at many different rentals never knowing if the pictures show what the condo really looks like. This rental was exactly what was shown and more! We were impressed with the updated features and location. The balcony
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Price per night from

$236

Responds fast!
avg. 5 minutes

Price per night from

$236

(7) Excellent 

40

10th Night FREE all 2019

Maui / Wailea

Wailea condo

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$224

Price per night from

$224

(2) Excellent 

50

Castaway Cove C201 at Wailea Beach Villas

Maui / Wailea

Wailea house

3 6 5 nights min

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

Price per night from

$1,197

Price per night from

$1,197

(13) Excellent 

0

Wailea Sunset Bungalow

Maui / Wailea

Wailea house

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning
“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 fam
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Price per night from

$996

Price per night from

$996

16

WAILEA ELUA, #0702

Maui / Wailea

Wailea apartment

2 6 5 nights min

  • 2 bedrooms
  • sleeps 6
  • 5 nights min
  • Ask about children
  • Ask about pets

Price per night from

$410

Price per night from

$410

(17) Very Good 

39

Palms at Wailea 702 Upstairs Garden View 1Bd/2Ba, Great Rates! Sleeps 4

Maui / Wailea

Wailea apartment

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Great Stay in #702” The unit was very spacious, very clean(the carpet had just been steam cleaned before we arrived) and is in great location in Wailea which is in the quieter part of Kihei. The lanai was large and perfect to spend the evening sipping
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Price per night from

$170

Responds fast!
avg. 5 minutes

Price per night from

$170

40

HO'OLEI #93-2-BEAUTIFULLY APPOINTED VILLA-SLEEPS 8

Maui / Wailea

Wailea condo

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$764

Price per night from

$764

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

$1,771

Price per night from

$1,771

(1) Excellent 

41

STOP! LOOK NO FURTHER! Palms at Wailea #1503 2Bd Ocean View Best Location!

Maui / Wailea

Wailea apartment

2 4 min stay varies

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

Price per night from

$361

Responds fast!
avg. 5 minutes

Price per night from

$361

45

HO'OLEI #24-3-BEAUTIFULLY APPOINTED VILLA-SLEEPS 10

Maui / Wailea

Wailea condo

3 10 min stay varies

  • 3 bedrooms
  • sleeps 10
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$708

Price per night from

$708

(15) Very Good 

24

Palms at Wailea #1501 Ocean View Inner Court Ground Floor 1Bd 1Ba Sleeps 4

Maui / Wailea

Wailea apartment

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child Friendly
“Enjoyable Stay!” Our overall experience was good. The property was quite comfortable. We loved the beautiful landscaping BUT the view of the ocean could be enhanced with a bit of selective trimming of the shrubs surrounding the patio area. The propert
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Price per night from

$226

Responds fast!
avg. 5 minutes

Price per night from

$226

(19) Excellent 

25

PREMIUM UPSCALE GEM #1 UNIT-THE PALMS at WAILEA-GALLERY SETTING CONTEMPORARY GEM

Maui / Wailea

Wailea apartment

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Ask about children
  • Car not necessary
“Happy with our stay” We enjoyed our stay. The location was very close to the beach and a pool, and there were chairs and gear we could use which was great. The room itself was quite nice and comfortable, including an excellent entertainment system and
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Price per night from

$287

Responds fast!
avg. 2 hours 44 minutes

Price per night from

$287

(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
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Price per night from

$316

Price per night from

$316

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

$246

Price per night from

$246

(2) Very Good 

24

Hale Makena Maui

Maui / Wailea

Wailea villa

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Ask about children
  • Ask about pets
“Our Stay at Hale Makena Maui” The house is beautiful and very comfortable. It was perfect for our group. The proximity to great beaches, snorkeling, kayaking and whale watching was terrific. THe outdoor living area and pool were a big plus. We definit
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Price per night from

$2,803

Responds fast!
avg. 1 hour 28 minutes

Price per night from

$2,803

(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

(6) Very Good 

30

Palms at Wailea #604 2Bd/2Ba, Fully Air Conditioned, Great Rates! Sleeps 6

Maui / Wailea

Wailea apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning
“As seen on the website” Unit 604 definitely met and surpassed our expectations. The booking process, checking in, and checking out were a breeze. We were a large group, with 3 units rented (from different companies) and ours was definitely the best de
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Price per night from

$190

Responds fast!
avg. 5 minutes

Price per night from

$190

(18) Very Good 

33

Palms at Wailea #2303 Ground Floor 2Bd/2Ba Near Beach, Great Rates! Sleeps 6

Maui / Wailea

Wailea apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Family Trip” Enjoyed every minute of it!
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Price per night from

$251

Responds fast!
avg. 5 minutes

Price per night from

$251

(1) Very Good 

45

Grand Champions #143 is a 3Bd/2Ba 1st floor golf course view condo, sleeps 8

Maui / Wailea

Wailea apartment

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$326

Responds fast!
avg. 5 minutes

Price per night from

$326

(8) Excellent 

50

Aqua Lani J305 Wailea Beach Villas

Maui / Wailea

Wailea villa

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Beautiful condo in Wailea!” A wonderful condo with 3 bedrooms & 3 bathrooms for six adults that was decorated with a modern touch & clean facilities. The beach is walking distance & the private pool very relaxing (separate kids pool area); didn't take
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Price per night from

$1,097

Price per night from

$1,097

27

South Kihei Home Rental

Maui / Wailea

Wailea house

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Nearest beach 0.3 mi
  • Child Friendly
  • Air conditioning

Price per night from

$975

Price per night from

$975

(10) Excellent 

14

Family Beach Headquarters: Maui Banyan 2 BR Condo at Beach, Sleeps 4-8

Maui / Wailea

Wailea apartment

2 8 5 nights min

  • 2 bedrooms
  • sleeps 8
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.1 mi
  • Swimming pool
“A wonderful family week in Kihei” Well-furnished 2 BR condo across the main road from a very nice beach in Kihei. Condo complex also had a nice heated pool. This was our first time as a family on Maui; we'll be back for sure, and likely to this locati
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Price per night from

$189

Responds fast!
avg. 1 hour 2 minutes

Price per night from

$189

(6) Excellent 

25

Wailea Ocean View, 2Bed, 2Bath Beautiful Update

Maui / Wailea

Wailea apartment

2 6 5 nights min

  • 2 bedrooms
  • sleeps 6
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool

Price per night from

$402

Responds fast!
avg. 1 hour 28 minutes

Price per night from

$402

(11) Excellent 

58

Prime Beachfront, Polo Beach Wailea/Makena #204 - Accommodates 1-6, Free Wifi

Maui / Wailea

Wailea apartment

2 6 5 nights min

  • 2 bedrooms
  • sleeps 6
  • 5 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“One of the finest vacation stays in Hawaii!” We have been travelling to Wailea since the early 1980's and always stayed just north of the Polo Club in other condos. The Polo Club locale, just off the beach, beautifully furnished, well maintained and
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Price per night from

$596

Responds fast!
avg. 12 minutes

Price per night from

$596

(8) Average 

29

Palms at Wailea #603 2Bd/2Ba Fully Air Conditioned, Great Rates! Sleeps 6

Maui / Wailea

Wailea apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Love Maui and the Palms” The Palms is our favourite place to stay in Maui. Room 603 was in very good shape but we had an incident the second to last day with water from the room above but the property management and rental management groups got on it
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Price per night from

$200

Responds fast!
avg. 5 minutes

Price per night from

$200

(11) Excellent 

25

Beautiful Modern Wailea! From $150

Maui / Wailea

Wailea apartment

1 4 7 nights min

  • 1 bedroom
  • sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“Wonderful condo, perfect location, great hosts!” This condo is just gorgeous! It's very spacious and beautifully decorated, with all the amenities that you could possibly want. My husband loves to cook, and he appreciated the well appointed kitchen w
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Price per night from

$172

Responds fast!
avg. 3 hours 34 minutes

Price per night from

$172