Vacation Rentals with Private Pool in Wailea Shopping Village Shopping Center, HI: Compare 10+ Sites & Save

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  2. Vacation Rentals with Private Pool
  3.  USA

  4.  Hawaii

  5.  Kihei
  6.  Wailea Shopping Village Shopping Center

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230 Best Vacation Rentals with Private Pool in Wailea Shopping Village Shopping Center (Starting from $354)

KBM Resorts FREE CAR Wailea Elua Village Ocean view Spacious 2-Bedroom Condo WEV-2103
KBM Resorts FREE CAR Wailea Elua Village Ocean view Spacious 2-Bedroom Condo WEV-2103
Apartment
Wailea, HI, USA
0.1k from Wailea Shopping Village Shopping Center center

Apartments, Cheap, Accommodations, Pools, Parking, Pet-friendly, Lodgings, Vacation rentals, Beach

1 Bedroom6 Guests
10.0

Exceptional

1 reviews

$901
Average price / night
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Wailea Elua 1308 - Direct Beachfront Luxury Condo in the Heart of Wailea, Maui
Wailea Elua 1308 - Direct Beachfront Luxury Condo in the Heart of Wailea, Maui
Condo
Kihei, HI, 96753, United States
0.1k from Wailea Shopping Village Shopping Center center

AC, Dryer, Fitness Equipment, Free Parking, Internet, Kitchen, Laundry, Microwave, No Smoking

2 Bedrooms5 Guests
10.0

Exceptional

61 reviews

$1632
Average price / night
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KBM Resorts FREE CAR Wailea Elua WEV-2009 Maui Beach Condo with Luxury Amenities
KBM Resorts FREE CAR Wailea Elua WEV-2009 Maui Beach Condo with Luxury Amenities
Apartment
HI, USA
0.2k from Wailea Shopping Village Shopping Center center

Apartments, Luxury, Accommodations, Pools, Parking, Pet-friendly, Lodgings, Beach, Hot tubs

1 Bedroom6 Guests
New to Booking
$795
Average price / night
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I.P.M PRESENTS: VILLA F101 - PRIVATE POOL + YARD! FLEXIBLE CANCELATION POLICY
I.P.M PRESENTS: VILLA F101 - PRIVATE POOL + YARD! FLEXIBLE CANCELATION POLICY
Villa
Kihei, HI, 96753, United States
0.4k from Wailea Shopping Village Shopping Center center

AC, Arcade, Barbecue, Dryer, Fitness Equipment, Free Parking, Hot Tub, Internet, Kitchen

3 Bedrooms8 Guests
9.8

Exceptional

26 reviews

$2096
Average price / night
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NEW KBM Resorts Ocean Views FREE CAR Wailea Ekahi 1-Bedroom Condo with Luxury Amenities WKV-45C
NEW KBM Resorts Ocean Views FREE CAR Wailea Ekahi 1-Bedroom Condo with Luxury Amenities WKV-45C
Apartment
Wailea, HI, USA
0.2k from Wailea Shopping Village Shopping Center center

Apartments, Luxury, Accommodations, Pools, Parking, Lodgings, Beach, Places to stay, Family

1 Bedroom2 Guests
New to Booking
$807
Average price / night
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I.P.M PRESENTS: Penthouse K108 - GREAT RATES! FLEXIBLE CANCELATION POLICY
I.P.M PRESENTS: Penthouse K108 - GREAT RATES! FLEXIBLE CANCELATION POLICY
Villa
Kihei, HI, 96753, United States
0.4k from Wailea Shopping Village Shopping Center center

AC, Arcade, Balcony, Barbecue, Dryer, Extra Bed, Fitness Equipment, Hot Tub, Internet

2 Bedrooms6 Guests
8.8

Fabulous

26 reviews

$1394
Average price / night
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KBM Resorts FREE CAR Wailea Beach Villa Spacious 3-Bedroom Condo with Sweeping Ocean view WBV-PH412
KBM Resorts FREE CAR Wailea Beach Villa Spacious 3-Bedroom Condo with Sweeping Ocean view WBV-PH412
Apartment
Wailea, HI, USA
0.4k from Wailea Shopping Village Shopping Center center

Apartments, Accommodations, Pools, Parking, Lodgings, Beach, Hot tubs, Places to stay, Family

1 Bedroom6 Guests
New to Booking
$4413
Average price / night
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ULTRA LUXURY SOLARA LUXE POOL VILLA D101, NEWLY RENOVATED, SLEEPS 8!
ULTRA LUXURY SOLARA LUXE POOL VILLA D101, NEWLY RENOVATED, SLEEPS 8!
Villa
Wailea, HI, 96753, United States
0.4k from Wailea Shopping Village Shopping Center center

AC, Arcade, Balcony, Barbecue, Dryer, Fitness Equipment, Free Parking, Hot Tub, Kitchen

3 Bedrooms8 Guests
10.0

Exceptional

13 reviews

$3763
Average price / night
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KBM Resorts 2 FREE CARS Grand Champions Remodeled 5-Bedroom Multi-Unit Listing in the Heart of Wailea GCH-12034
KBM Resorts 2 FREE CARS Grand Champions Remodeled 5-Bedroom Multi-Unit Listing in the Heart of Wailea GCH-12034
Apartment
Wailea, HI, USA
0.7k from Wailea Shopping Village Shopping Center center

Apartments, Accommodations, Pools, Parking, Lodgings, Places to stay, Family

1 Bedroom12 Guests
New to Booking
$1522
Average price / night
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BEAUTIFUL BALI HAI POOL VILLA F102 PRIVATE PLUNGE POOL, LARGE YARD, SLEEPS 8!
BEAUTIFUL BALI HAI POOL VILLA F102 PRIVATE PLUNGE POOL, LARGE YARD, SLEEPS 8!
Villa
Wailea, HI, 96753, United States
0.4k from Wailea Shopping Village Shopping Center center

AC, Arcade, Balcony, Barbecue, Dryer, Fitness Equipment, Free Parking, Hot Tub, Kitchen

3 Bedrooms8 Guests
9.8

Exceptional

23 reviews

$3330
Average price / night
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NEW KBM Resorts FREE CAR Grand Champions Remodeled 1-Bedroom Villa in the Heart of Wailea GCH-181
NEW KBM Resorts FREE CAR Grand Champions Remodeled 1-Bedroom Villa in the Heart of Wailea GCH-181
Apartment
Wailea, HI, USA
0.7k from Wailea Shopping Village Shopping Center center

Apartments, Accommodations, Pools, Parking, Lodgings, Places to stay, Family

1 Bedroom4 Guests
New to Booking
$548
Average price / night
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UBER LUXE SERENITY HOUSE POOL VILLA D102, LARGE YARD, NEWLY RENOVATED, SLEEPS 8
UBER LUXE SERENITY HOUSE POOL VILLA D102, LARGE YARD, NEWLY RENOVATED, SLEEPS 8
Villa
Wailea, HI, 96753, United States
0.4k from Wailea Shopping Village Shopping Center center

AC, Arcade, Balcony, Barbecue, Dryer, Fitness Equipment, Free Parking, Hot Tub, Kitchen

3 Bedrooms8 Guests
9.6

Exceptional

11 reviews

$3763
Average price / night
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KBM Resorts FREE CAR Grand Champions Upgraded 3-Bedroom with Wraparound Large Lanai GCH-134
KBM Resorts FREE CAR Grand Champions Upgraded 3-Bedroom with Wraparound Large Lanai GCH-134
Apartment
Wailea, HI, USA
0.7k from Wailea Shopping Village Shopping Center center

Apartments, Cheap, Accommodations, Pools, Parking, Pet-friendly, Lodgings, Vacation rentals, Beach

9 Bedrooms74 Guests
10.0

Exceptional

2 reviews

$1490
Average price / night
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FABULOUS FLORAL GARDENS POOL VILLA G102! PRIVATE PLUNGE POOL, LARGE YARD, SLEEPS 8!
FABULOUS FLORAL GARDENS POOL VILLA G102! PRIVATE PLUNGE POOL, LARGE YARD, SLEEPS 8!
Villa
Wailea, HI, 96753, United States
0.4k from Wailea Shopping Village Shopping Center center

AC, Arcade, Balcony, Barbecue, Dryer, Fitness Equipment, Free Parking, Hot Tub, Kitchen

3 Bedrooms8 Guests
10.0

Exceptional

14 reviews

$3113
Average price / night
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Wailea Luxury Resort Vista
Wailea Luxury Resort Vista
Apartment
Wailea, HI, USA
1.0k from Wailea Shopping Village Shopping Center center

Apartments, Luxury, Accommodations, Pools, Parking, Lodgings, Places to stay

1 Bedroom4 Guests
New to Booking
$767
Average price / night
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I.P.M PRESENTS: PH-I203 - OCEAN VIEWS AND NEW DECOR. FLEXIBLE CANCELATION POLICY
I.P.M PRESENTS: PH-I203 - OCEAN VIEWS AND NEW DECOR. FLEXIBLE CANCELATION POLICY
Villa
Kihei, HI, 96753, United States
0.4k from Wailea Shopping Village Shopping Center center

AC, Arcade, Balcony, Barbecue, Dryer, Elevator, Fitness Equipment, Free Parking, Hot Tub

3 Bedrooms6 Guests
10.0

Exceptional

13 reviews

$1656
Average price / night
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KBM Resorts FREE CAR Polo Beach POL-109 Ground Floor Steps to the Sand Sunset Views
KBM Resorts FREE CAR Polo Beach POL-109 Ground Floor Steps to the Sand Sunset Views
Apartment
Wailea, HI, USA
1.7k from Wailea Shopping Village Shopping Center center

Apartments, Accommodations, Pools, Parking, Pet-friendly, Lodgings, Vacation rentals, Beach, Places to stay

1 Bedroom6 Guests
New to Booking
$6190
Average price / night
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Luxury  Cottage w/ Private Pool. Under The Warm Maui Sun Pmt #BBKM\\2016\\0004
Luxury Cottage w/ Private Pool. Under The Warm Maui Sun Pmt #BBKM\\2016\\0004
Cottage
Kihei, HI, 96753, United States
0.5k from Wailea Shopping Village Shopping Center center

AC, Barbecue, Dryer, Fitness Equipment, Free Parking, Hot Tub, Internet, Kitchen, Laundry

1 Bedroom2 Guests
10.0

Exceptional

188 reviews

$607
Average price / night
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257 Hale Kamaole
257 Hale Kamaole
Apartment
Wailea, HI, USA
2.3k from Wailea Shopping Village Shopping Center center

Apartments, Cheap, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Places to stay, Beach rentals

1 Bedroom9 Guests
10.0

Exceptional

1 reviews

$789
Average price / night
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Private Ocean Front at Wailea Beach Villas B102
Private Ocean Front at Wailea Beach Villas B102
Villa
Wailea, HI, 96753, United States
0.5k from Wailea Shopping Village Shopping Center center

AC, Balcony, Barbecue, Dryer, Fitness Equipment, Free Parking, Hot Tub, Internet, Kitchen

3 Bedrooms8 Guests
10.0

Exceptional

30 reviews

$3635
Average price / night
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I.P.M PRESENTS: VILLA E102 - PRIVATE POOL + YARD. FLEXIBLE CANCELATION POLICY
I.P.M PRESENTS: VILLA E102 - PRIVATE POOL + YARD. FLEXIBLE CANCELATION POLICY
Villa
Kihei, HI, 96753, United States
0.5k from Wailea Shopping Village Shopping Center center

AC, Arcade, Barbecue, Dryer, Fitness Equipment, Free Parking, Hot Tub, Internet, Kids Pool

3 Bedrooms8 Guests
9.0

Fabulous

12 reviews

$1893
Average price / night
Check Availability
I.P.M PRESENTS: VILLA E101 - PRIVATE POOL + YARD. FLEXIBLE CANCELATION POLICY
I.P.M PRESENTS: VILLA E101 - PRIVATE POOL + YARD. FLEXIBLE CANCELATION POLICY
Villa
Kihei, HI, 96753, United States
0.5k from Wailea Shopping Village Shopping Center center

AC, Arcade, Barbecue, Dryer, Fitness Equipment, Free Parking, Internet, Kitchen, Laundry

3 Bedrooms8 Guests
10.0

Exceptional

21 reviews

$2150
Average price / night
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Ground-Floor Gem in Wailea Ekahi Village
Ground-Floor Gem in Wailea Ekahi Village
Condo
Kihei, HI, 96753, United States
0.6k from Wailea Shopping Village Shopping Center center

AC, Balcony, Barbecue, Crib, Dryer, Elevator, Free Parking, Heater, Hot Tub

1 Bedroom4 Guests
9.0

Fabulous

2 reviews

$516
Average price / night
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 16B; Ocean View, Quiet Beachfront King Studio in Luxurious Wailea Ekahi Resort
16B; Ocean View, Quiet Beachfront King Studio in Luxurious Wailea Ekahi Resort
Apartment
Kihei, HI, 96753, United States
0.6k from Wailea Shopping Village Shopping Center center

AC, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Microwave, No Smoking

1 Bedroom2 Guests
10.0

Exceptional

24 reviews

$354
Average price / night
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Wailea Beach Villas E-302 on Wailea Beach
Wailea Beach Villas E-302 on Wailea Beach
Condo
Kihei, HI, 96753, United States
0.6k from Wailea Shopping Village Shopping Center center

AC, Free Parking, Internet, No Smoking, Pool

3 Bedrooms8 Guests
9.6

Exceptional

16 reviews

$2933
Average price / night
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14D Panoramic ocean view, beautiful sunset every night. Best in Ekahi!
14D Panoramic ocean view, beautiful sunset every night. Best in Ekahi!
Condo
Wailea, HI, 96753, United States
0.7k from Wailea Shopping Village Shopping Center center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

1 Bedroom2 Guests
10.0

Exceptional

126 reviews

$753
Average price / night
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Grand Champions in Wailea – Spacious Villa Near Pool w/ Ocean & Sunset Views
Grand Champions in Wailea – Spacious Villa Near Pool w/ Ocean & Sunset Views
Condo
Wailea, HI, 96753, United States
0.7k from Wailea Shopping Village Shopping Center center

AC, Balcony, Barbecue, Crib, Dryer, Elevator, Free Parking, Hot Tub, Internet

3 Bedrooms6 Guests
9.8

Exceptional

91 reviews

$749
Average price / night
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Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals with Private Pool in Wailea Shopping Village Shopping Center.

Wailea Shopping Village Shopping Center Vacation Rentals with Private Pool on the Map

Frequently Asked Questions

You can explore 230 verified vacation rentals with a private pool in Wailea Shopping Village Shopping Center. These include standalone villas and private homes where the pool is reserved exclusively for your group.

Prices for rentals with a private pool in Wailea Shopping Village Shopping Center vary depending on the property size, location, and travel season. Rates typically start from around $354 per night, with higher prices for larger homes, prime locations, or peak travel periods.

Yes, properties listed with private pools are intended for the exclusive use of guests staying at that home. You can review listing photos and descriptions to better understand the layout and level of privacy offered.

Yes, some vacation rentals with private pools in Wailea Shopping Village Shopping Center also welcome pets. Currently, 5 listings allow pets, although policies may vary. It’s a good idea to review any rules related to pets and outdoor areas before booking.

Private pool properties are often in high demand, especially during holidays and warmer months, so booking 90 to 120 days in advance is recommended. During quieter periods, you may still find availability closer to your travel dates.

Vacation rentals with private pools in Wailea Shopping Village Shopping Center often include additional features such as Private Pool, Pool, and View. These amenities enhance comfort and create a more relaxing, self-contained stay.

Some family-friendly vacation rentals in Wailea Shopping Village Shopping Center include safety features such as pool fences, covers, or screened enclosures. It’s recommended to check the property details to confirm whether a specific rental meets your safety preferences.