Wailea Vacation Rental Getaways


Refine Your Search
Check-In 
calendar

Check-Out
calendar
  • Property Options
  • Amenities
  • Location Type
  • Bed
  • Bath
  • Sleeps
Max Price Per Week $
  • Special Offers
  • Online Booking
  • Home/Villa
  • Cottage/Cabin
  • Condo/Townhome
  • Bed & Breakfast
  • Apt/Room/Suite
  • Air Conditioning
  • Washer/Dryer
  • Full Kitchen
  • Satellite/Cable TV
  • Handicap Access
  • High Speed Internet
  • Elevator
  • Maid Service
  • Garage Parking
  • Pets Allowed
  • Private Pool
  • Pool Access
  • Hot Tub
  • Fireplace
  • Smoking allowed
  • Beach Access
  • Beach Front
  • Golf on site
  • Golf nearby
  • Ocean Front
  • Ocean View
  • Lake Front
  • Lake View
  • Ski in/out
  • Walk to Slopes
  • Skiing nearby
 
Sort by: Type BR/BA/Sleeps Price

Palms at Wailea #1105 Oceanview Completely Remodeled 2Bd ...

Wailea
Palms at Wailea #1105 Oceanview Completely Remodeled 2Bd 2Bath Great Rates! The fabulous Keawakapu ...
Condo 2 / 2 / 4

*
Online booking available

$299 - $641
Per Night

$1925 - $4490
Per Week

Grand Champions #36

Wailea
This is a great property with a real tropical "Tommy Bahama" feel...Upscale furnishings and attentio...
Condo 2 / 2 / 6

*
Online booking available

$195 - $255
Per Night

$1365 - $1785
Per Week

Summer Special! Wailea Ekahi 46F- Spacious 2 BR 2 Bath Co...

Wailea
Summer Special! Wailea Ekahi 46F- Spacious 2 BR 2 Bath Condo in Wailea! Wailea Ekahi - Nicely appoi...
Condo 2 / 2 / 6

*
Online booking available

$252 - $380
Per Night

$1575 - $2660
Per Week

Palms at Wailea #1508 Panroamic Ocean Views 2/2 Sleeps 6 ...

Wailea
Palms at Wailea #1508 Panroamic Ocean Views 2/2 Sleeps 6 Great Rates The fabulous Keawakapu Beach i...
Condo 2 / 2 / 6

*
Online booking available

$329 - $684
Per Night

$2303 - $4790
Per Week

Grand Champions 35 - 3rd Floor Ocean View

Wailea
Grand Champions 35 is an inviting third floor, two bedroom, two bath, Ocean View condo. The living ...
Condo 2 / 2 / 5

*
Online booking available

$210 - $591
Per Night

$1470 - $4137
Per Week

Grand Champions #090

Wailea
Beautifully Remodeled and furnished two bedroom Condo overlooking the Golf Course. The kitchen ad ba...
Condo 2 / 2 / 6

*
Online booking available

$425 - $530
Per Night

$2975 - $3710
Per Week

Wailea Ekolu #1207 2B/2B Fully Remodeled Ground Floor Con...

Wailea
Wailea Ekolu #1207 2B/2B Fully Remodeled Ground Floor Condo w/ Ocean View Welcome to Wailea Ekolu V...
Condo 2 / 2 / 6

*
Online booking available

$185 - $570
Per Night

$1295 - $3990
Per Week

Wailea Ekahi 17D - 2nd Floor Panoramic Ocean Views

Wailea
Come enjoy condominium living at its finest at Wailea Ekahi #17D. Located in the heart of Wailea, Ma...
Condo 1 / 2 / 4

*
Online booking available

$282 - $770
Per Night

$1973 - $5389
Per Week

Wailea Ekolu 1610 - Ocean View Renovated 2 Bedroom

Wailea
This spectacular two bedroom town home has been renovated throughout. The upstairs living area has a...
Condo 2 / 2.5 / 5

*
Online booking available

$273 - $739
Per Night

$1909 - $5171
Per Week

Grand Champions #45 is a 2bd 2ba Ocean view condo that Sl...

Wailea
Grand Champions #45 is a 2bd 2ba Ocean view condo that Sleeps 6 Great Rates! The nearby Ulua and Mo...
Condo 2 / 2 / 6

*
Online booking available

$199 - $427
Per Night

$1393 - $2990
Per Week

Wailea Ekolu #407 Completely Remodeled with Panoramic Oce...

Wailea
Wailea Ekolu #407 Completely Remodeled with Panoramic Ocean Views. Sleeps 2 Wailea Ekolu Unit 407 i...
Condo 1 / 2 / 2

*
Online booking available

$225 - $427
Per Night

$1575 - $2990
Per Week

Palms at Wailea 1902 Garden View 2Bd 2Ba Sleeps 6

Wailea
Enjoy your stay in paradise at The Palms at Wailea, a gorgeous property with lush, tropical landscap...
Condo 2 / 2 / 6

*
Online booking available

$224 - $463
Per Night

$1568 - $3240
Per Week

Wailea Ekolu #201 Remodeled 2Bd/2Ba Oceanview Condo Sleeps 6

Wailea
Wailea Ekolu has several lovely pool areas as well as a large pavilion area for larger groups. There...
Condo 2 / 2 / 6

*
Online booking available

$184 - $564
Per Night

$1288 - $3950
Per Week

Wailea Ekahi 35B - 2 Level Condo Walk to Beach

Wailea
Wailea Ekahi Village 35B is where you want to be. It is the paradise you have been looking for. Walk...
Condo 2 / 2.5 / 4

*
Online booking available

$321 - $816
Per Night

$2244 - $5715
Per Week

Wailea Ekolu 1604 - 2nd Floor Two Bedroom Condo

Wailea
A Second Floor, Two bedroom Two bath condo with garden and peek-a-boo ocean views. Our guests are we...
Condo 2 / 2 / 4

*
Online booking available

$209 - $614
Per Night

$1463 - $4300
Per Week

Wailea Ekolu #105 Scenic Ocean View, Great Location, Slee...

Wailea
Wailea Ekolu #105 Scenic Ocean View, Great Location, Sleeps 4 Wailea Ekolu has several lovely pool ...
Condo 2 / 2 / 4

*
Online booking available

$203 - $607
Per Night

$1422 - $4250
Per Week

Palms at Wailea Unit #2305 Quiet and Very Private! Summer...

Wailea
Palms at Wailea Unit #2305 Quiet and Very Private! Summer Special $169 We are pleased that our prop...
Condo 1 / 2 / 2

*
Online booking available

$179 - $427
Per Night

$1253 - $2990
Per Week

Wailea Ekahi 17E - Ocean View Oversized Lanai

Wailea
This condominium home has been beautifully upgraded throughout and boasts a wonderful kitchen, dinin...
Condo 1 / 2 / 2

*
Online booking available

$282 - $770
Per Night

$1973 - $5389
Per Week

Wailea Elua 1904 - 2 Bedroom Remodeled on the Beach

Wailea
Newly remodeled, Two bedroom / Two bathroom, second floor condominium right on the Beach! It is perf...
Condo 2 / 2 / 4

*
Online booking available

$577 - $1633
Per Night

$4039 - $11431
Per Week

Ho'olei 81-2 - Luxury 3 Bedroom Townhouse with Spectacula...

Wailea
Enjoy more than 2500 feet of comfortable yet lavish, uniquely and professionally decorated living sp...
Condo 3 / 3.5 / 10

*
Online booking available

$898 - $2400
Per Night

$6284 - $16800
Per Week

Palms at Wailea 2303 Ground Floor 2bd 2ba Sleeps 6 Great ...

Wailea
Palms at Wailea 2303 Ground Floor 2bd 2ba Sleeps 6 Great Rates! We are pleased that our properties ...
Condo 2 / 2 / 6

*
Online booking available

$250 - $463
Per Night

$1750 - $3240
Per Week

Summer Special! Wailea Ekahi 48C ~ 1 BR 2 Bath Wailea Condo!

Wailea
Wailea Ekahi Village - 1 bedroom, 2 bath condo with a calming garden view located in the Upper Villa...
Condo 1 / 2 / 4

*
Online booking available

$203 - $280
Per Night

$1134 - $1960
Per Week

Grand Champions 165 - Access to Pools & Jacuzzi

Wailea
The inviting tropical decor in Grand Champions 165 greets you as you enter. Beautiful new tile flows...
Condo 2 / 2 / 4

*
Online booking available

$210 - $591
Per Night

$1470 - $4137
Per Week

Ho'olei 81-5 - Excellent Location Above Pool and Waterfall

Wailea
Unwind in this spectacular three bedroom deluxe accommodation. Beautiful decorations, many of which ...
Condo 3 / 3.5 / 8

*
Online booking available

$898 - $2255
Per Night

$6284 - $15785
Per Week

Wailea Ekolu #205 Ocean View, Ground Floor, Sleeps 6

Wailea
Wailea Ekolu has several lovely pool areas as well as a large pavilion area for larger groups. There...
Condo 2 / 2 / 6

*
Online booking available

$196 - $593
Per Night

$1369 - $4150
Per Week

 

More Getaway Locations and Properties