Owner Direct Rentals with Pool in Kihei

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  2. Vacation Rentals with Pool
  3.  USA

  4.  Hawaii

  5.  Kihei

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3294 Kihei Rentals with Pool From $248

Looking for an exciting rental with a pool in Kihei? Discover a curated collection of vacation homes featuring indoor or outdoor swimming pools. Owner Direct makes it simple to cross-reference verified properties for your pool-side relaxation.

103 Kihei Holiday
103 Kihei Holiday
Apartment
Kihei, HI, USA
0.7k from Kihei center

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

1 Bedroom7 Guests
9.3

Superb

3 reviews

$469
Average price / night
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PRIVATE HOME on a lush half acre, Kihei Oasis boasts a 40k gallon heated pool!
PRIVATE HOME on a lush half acre, Kihei Oasis boasts a 40k gallon heated pool!
House
Kihei, HI, 96753, United States
0.4k from Kihei center

AC, Barbecue, Crib, Dryer, Fireplace, Free Parking, Hot Tub, Internet, Kitchen

3 Bedrooms6 Guests
10.0

Exceptional

191 reviews

$995
Average price / night
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110 Kihei Holiday
110 Kihei Holiday
Apartment
Kihei, HI, USA
0.7k from Kihei center

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

1 Bedroom7 Guests
1.0

Review score

1 reviews

$469
Average price / night
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2BD/2BA! Charming Retreat: Ground Floor w/King, AC, Garden/Lanai
2BD/2BA! Charming Retreat: Ground Floor w/King, AC, Garden/Lanai
Condo
Kihei, HI, 96753, United States
0.5k from Kihei center

AC, Barbecue, Crib, Dryer, Free Parking, Internet, Kitchen, Laundry, Microwave

2 Bedrooms6 Guests
New to Booking
$391
Average price / night
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214 Kihei Holiday
214 Kihei Holiday
Apartment
Kihei, HI, USA
0.7k from Kihei center

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

1 Bedroom7 Guests
9.3

Superb

3 reviews

$491
Average price / night
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☼ Stylish & Bright 2bd Oceanfront Condo|5★ Views
☼ Stylish & Bright 2bd Oceanfront Condo|5★ Views
Condo
Kihei, HI, 96753, United States
0.5k from Kihei center

AC, Balcony, Barbecue, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Laundry

2 Bedrooms4 Guests
10.0

Exceptional

11 reviews

$409
Average price / night
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Kihei Holiday 311
Kihei Holiday 311
Apartment
Kihei, HI, USA
0.7k from Kihei center

Apartments, Cheap, Accommodations, Pools, Lodgings, Places to stay

2 Bedrooms7 Guests
8.3

Very Good

9 reviews

$434
Average price / night
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Private Luxury Villa in Kihei. Just moments walk to the beach. 10/10 reviews!
Private Luxury Villa in Kihei. Just moments walk to the beach. 10/10 reviews!
House
Kihei, HI, 96753, United States
0.5k from Kihei center

AC, Balcony, Barbecue, Crib, Dryer, Extra Bed, Free Parking, Hot Tub, Internet

6 Bedrooms18 Guests
10.0

Exceptional

46 reviews

$3469
Average price / night
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107 Kihei Holiday
107 Kihei Holiday
Apartment
Kihei, HI, USA
0.7k from Kihei center

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

2 Bedrooms4 Guests
New to Booking
$249
Average price / night
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Secluded home with spectacular ocean and sunset views
Secluded home with spectacular ocean and sunset views
House
Kihei, HI, 96753, United States
0.5k from Kihei center

AC, Balcony, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave

4 Bedrooms10 Guests
10.0

Exceptional

23 reviews

$1566
Average price / night
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Your Maui Adventure Awaits - Sugar Beach
Your Maui Adventure Awaits - Sugar Beach
Apartment
Kihei, HI, USA
0.7k from Kihei center

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

2 Bedrooms5 Guests
New to Booking
$336
Average price / night
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Kihei Holiday Stunning Ocean View #309 2bd/1ba condo, 1 min walk to the ocean.
Kihei Holiday Stunning Ocean View #309 2bd/1ba condo, 1 min walk to the ocean.
Condo
Kihei, HI, 96753, United States
0.6k from Kihei center

AC, Dryer, Internet, Laundry, No Smoking, Pool, Washer

2 Bedrooms4 Guests
10.0

Exceptional

2 reviews

$371
Average price / night
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Kihei Holiday 116
Kihei Holiday 116
Apartment
Kihei, HI, USA
0.7k from Kihei center

Apartments, Accommodations, Pools, Lodgings, Vacation rentals, Places to stay, Self-catering, Beach rentals

2 Bedrooms6 Guests
7.8

Good

15 reviews

$314
Average price / night
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Renovated Maui Escape/Partial Ocean View/Boutique Condo/Steps to Sugar Beach
Renovated Maui Escape/Partial Ocean View/Boutique Condo/Steps to Sugar Beach
Condo
Kihei, HI, 96753, United States
0.6k from Kihei center

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

1 Bedroom4 Guests
10.0

Exceptional

1 reviews

$353
Average price / night
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Ocean-View Kihei Condo with Pool Access!
Ocean-View Kihei Condo with Pool Access!
Apartment
Kihei, HI, USA
0.7k from Kihei center

Apartments, Accommodations, Parking, Spa, Lodgings, Vacation rentals, Beach, Hot tubs, Places to stay

2 Bedrooms4 Guests
9.7

Exceptional

16 reviews

$312
Average price / night
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Beautifully Remodeled 2 Bedroom/ 2 Bath- Stunning Views - Kihei Holiday #315
Beautifully Remodeled 2 Bedroom/ 2 Bath- Stunning Views - Kihei Holiday #315
Condo
Kihei, Maui, HI, 96753, United States
0.7k from Kihei center

AC, Balcony, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave

2 Bedrooms4 Guests
New to Booking
$370
Average price / night
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Specials - Sep-Dec, Tropical Oceanfront Estate, Pool, Gated, Privacy, Ocean view
Specials - Sep-Dec, Tropical Oceanfront Estate, Pool, Gated, Privacy, Ocean view
House
Kihei, HI, 96753, United States
0.7k from Kihei center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Internet, Kitchen, Laundry, Living Area

6 Bedrooms17 Guests
9.6

Exceptional

220 reviews

$2531
Average price / night
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Grand Opening Prices! Ocean Views! Steps 2 Beach! Entire condo in Kihei, Hawaii!
Grand Opening Prices! Ocean Views! Steps 2 Beach! Entire condo in Kihei, Hawaii!
Condo
Kihei, HI, 96753, United States
0.8k from Kihei center

AC, Barbecue, Crib, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen

1 Bedroom4 Guests
New to Booking
$575
Average price / night
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Ocean View 2-bedroom condo with pool and AC in wonderful Kihei
Ocean View 2-bedroom condo with pool and AC in wonderful Kihei
Condo
Kihei, HI, 96753, United States
0.8k from Kihei center

AC, Balcony, Crib, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Laundry

2 Bedrooms4 Guests
9.8

Exceptional

31 reviews

$470
Average price / night
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2BR Oceanview Family Favorite! Beach, Pool, Hot Tub, AC! Whale Season Views!
2BR Oceanview Family Favorite! Beach, Pool, Hot Tub, AC! Whale Season Views!
Condo
Kihei, HI, 96753, United States
0.8k from Kihei center

AC, Balcony, Barbecue, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Laundry

2 Bedrooms5 Guests
9.6

Exceptional

87 reviews

$397
Average price / night
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1 Bedroom Condo with Peek-a-Boo Ocean View
1 Bedroom Condo with Peek-a-Boo Ocean View
Condo
Kihei, HI, 96753, United States
0.8k from Kihei center

AC, Balcony, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen

1 Bedroom4 Guests
9.8

Exceptional

79 reviews

$248
Average price / night
Check Availability

Pro Tip:
OwnerDirectVacationRental 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 Pool in Kihei.

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From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.

Frequently Asked Questions

There are a lot of options in Kihei. If you plan on staying in the Kihei area, consider making a reservation for a few nights at one of these properties as these have been rated the top Vacation Rentals wint Pool in Kihei

You can explore 3294 verified vacation rentals with a pool in Kihei. These include a wide range of private homes, villas, and condos that offer on-site swimming facilities for a more relaxing stay.

Prices for vacation rentals with a pool in Kihei vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $248 per night, with private pool homes and peak travel periods often costing more.

Many rentals in Kihei offer private pools for exclusive use, while others provide access to shared or community pools. You can use filters to specifically find properties with private pools if that is your preference.

Yes, some vacation rentals with pools in Kihei welcome pets. Currently, 3 listings allow pets, although policies may vary by property. It’s a good idea to review any rules related to pets around pool areas before booking.

Properties with pools are often in high demand, especially during warmer months and holidays, so booking 90 to 120 days in advance is recommended for the best selection. During off-peak seasons, you may still find availability closer to your travel dates.

Vacation rentals with pools in Kihei often include additional outdoor features such as Pool, Wellness Facilities, and Internet. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in Kihei offer heated pools, which can be especially useful during cooler months. In certain cases, pool heating may be available for an additional fee, so it’s best to check the property details before booking.