Vacation Rentals with Private Pool in Island Sails, HI: Compare 10+ Sites & Save

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  2. Vacation Rentals with Private Pool
  3.  USA

  4.  Hawaii

  5.  Princeville
  6.  Island Sails

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107 Best Vacation Rentals with Private Pool in Island Sails (Starting from $232)

The Cliffs at Princeville by VRHost
The Cliffs at Princeville by VRHost
Resort
Princeville, HI, USA
0.3k from Island Sails center

Accommodations, Pools, Resorts, Parking, Spa, Lodgings, Jacuzzis, Places to stay, Family

28 Bedrooms47 Guests
New to Booking
$353
Average price / night
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Bright, modern home w/ocean views from the huge wraparound deck & private pool
Bright, modern home w/ocean views from the huge wraparound deck & private pool
House
Princeville, HI, 96722, United States
0.2k from Island Sails center

Balcony, Barbecue, Dryer, Extra Bed, Free Parking, Hot Tub, Internet, Kitchen, Laundry

3 Bedrooms8 Guests
9.6

Exceptional

26 reviews

$990
Average price / night
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Cool, Lo-Fi Styled Surf Shack - Ka Hale Nalu
Cool, Lo-Fi Styled Surf Shack - Ka Hale Nalu
House
Princeville, HI, 96722, United States
0.2k from Island Sails center

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

3 Bedrooms7 Guests
9.8

Exceptional

16 reviews

$1267
Average price / night
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NEW! Magical+Modern with Ocean views - 2-bedroom townhome with AC in Princeville
NEW! Magical+Modern with Ocean views - 2-bedroom townhome with AC in Princeville
House
Princeville, HI, 96722, United States
0.3k from Island Sails center

AC, Balcony, Barbecue, Dryer, Fitness Equipment, Free Parking, Internet, Laundry, Living Area

2 Bedrooms4 Guests
New to Booking
$535
Average price / night
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Cliffs at Princeville #3201, Beautiful Ocean-Bluff Resort, Private Lanai
Cliffs at Princeville #3201, Beautiful Ocean-Bluff Resort, Private Lanai
Condo
Princeville, HI, 96722, United States
0.3k from Island Sails center

Balcony, Barbecue, Dryer, Extra Bed, Fitness Equipment, Hot Tub, Internet, Kitchen, Laundry

1 Bedroom4 Guests
9.4

Superb

84 reviews

$344
Average price / night
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Cliffs at Princeville 1208 Beautiful 2 Studio Unit, Full Kitchen
Cliffs at Princeville 1208 Beautiful 2 Studio Unit, Full Kitchen
Condo
Princeville, HI, 96722, United States
0.3k from Island Sails center

Balcony, Barbecue, Dryer, Fitness Equipment, Hot Tub, Internet, Kitchen, Laundry, Microwave

2 Bedrooms4 Guests
9.2

Superb

74 reviews

$348
Average price / night
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Excellent North Shore Paradise  2BD/2BA / Pool / Gym / NEW A/C
Excellent North Shore Paradise 2BD/2BA / Pool / Gym / NEW A/C
Condo
Princeville, HI, 96722, United States
0.3k from Island Sails center

AC, Barbecue, Dryer, Extra Bed, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet

3 Bedrooms6 Guests
10.0

Exceptional

65 reviews

$451
Average price / night
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Our Kauai Island Gem - Check out our last minute Specials!
Our Kauai Island Gem - Check out our last minute Specials!
Condo
Princeville, HI, 96722, United States
0.3k from Island Sails center

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

1 Bedroom4 Guests
9.8

Exceptional

106 reviews

$311
Average price / night
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 Renovated, Air Conditioned 2nd Floor Princeville Condo\nHas Primary BdRm & Loft
Renovated, Air Conditioned 2nd Floor Princeville Condo\nHas Primary BdRm & Loft
Condo
Princeville, HI, 96722, United States
0.3k from Island Sails center

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

1 Bedroom2 Guests
10.0

Exceptional

141 reviews

$260
Average price / night
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Gorgeous home with private pool, hammock, large patio, lanai, & enclosed yard
Gorgeous home with private pool, hammock, large patio, lanai, & enclosed yard
House
Princeville, HI, 96722, United States
0.4k from Island Sails center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Kitchen, Laundry, Living Area

2 Bedrooms4 Guests
10.0

Exceptional

3 reviews

$686
Average price / night
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Modern Luxury Meets Tranquility
Modern Luxury Meets Tranquility
House
PRINCEVILLE, HI, 96722, United States
0.4k from Island Sails center

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

4 Bedrooms10 Guests
10.0

Exceptional

8 reviews

$1486
Average price / night
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The Cliffs at Princeville #7302, Pristine Ocean-Bluff Views, Private Lanai
The Cliffs at Princeville #7302, Pristine Ocean-Bluff Views, Private Lanai
Condo
Princeville, HI, 96722, United States
0.4k from Island Sails center

Balcony, Barbecue, Crib, Dryer, Fitness Equipment, Hot Tub, Internet, Kitchen, Laundry

2 Bedrooms6 Guests
9.6

Exceptional

124 reviews

$468
Average price / night
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Private home w/resort style salt water pool and A/C
Private home w/resort style salt water pool and A/C
House
Princeville, HI, 96722, United States
0.4k from Island Sails center

AC, Barbecue, Crib, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area

4 Bedrooms12 Guests
9.8

Exceptional

74 reviews

$1216
Average price / night
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 Fresh & Clean, Air Conditioned Second Floor Condo in Princeville
Fresh & Clean, Air Conditioned Second Floor Condo in Princeville
Condo
Princeville, HI, 96722, United States
0.4k from Island Sails center

AC, Balcony, Barbecue, Free Parking, Hot Tub, Internet, Kitchen, Microwave, No Smoking

1 Bedroom2 Guests
9.8

Exceptional

270 reviews

$232
Average price / night
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Modern Island Studio in a spectacular location on Kauai’s lovely North Shore
Modern Island Studio in a spectacular location on Kauai’s lovely North Shore
Condo
Princeville, HI, 96722, United States
0.4k from Island Sails center

AC, Balcony, Barbecue, Free Parking, Hot Tub, Internet, Kitchen, Living Area, Microwave

1 Bedroom3 Guests
9.8

Exceptional

264 reviews

$322
Average price / night
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Huge Home w/ Private Pool, Jacuzzi, & Water Slide! Sleeps 18!
Huge Home w/ Private Pool, Jacuzzi, & Water Slide! Sleeps 18!
House
Princeville, HI, 96722, United States
0.4k from Island Sails center

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

5 Bedrooms18 Guests
10.0

Exceptional

62 reviews

$1680
Average price / night
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Pau Hana Hale - Private Mini-Resort with Pool
Pau Hana Hale - Private Mini-Resort with Pool
House
Princeville, HI, 96722, United States
0.5k from Island Sails center

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

5 Bedrooms8 Guests
10.0

Exceptional

15 reviews

$1523
Average price / night
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Hale Hou Nanea: 4  BR, 3.5  BA House in Princeville, Sleeps 10
Hale Hou Nanea: 4 BR, 3.5 BA House in Princeville, Sleeps 10
House
Princeville, HI, 96722, United States
0.5k from Island Sails center

AC, Dryer, Free Parking, Internet, Kitchen, Living Area, Microwave, No Smoking, Pool

4 Bedrooms10 Guests
New to Booking
$1590
Average price / night
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Oceanfront Alii Kai I Condominium #7202 Princeville Kauai
Oceanfront Alii Kai I Condominium #7202 Princeville Kauai
Condo
Princeville, HI, 96722, United States
0.5k from Island Sails center

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

2 Bedrooms4 Guests
8.4

Very Good

122 reviews

$376
Average price / night
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Privacy in Princeville with Pool, Ocean & Mountain
Privacy in Princeville with Pool, Ocean & Mountain
House
Princeville, HI, 96722, United States
0.5k from Island Sails center

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

3 Bedrooms6 Guests
10.0

Exceptional

27 reviews

$896
Average price / night
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Ocean Pool Hale 3br 2ba Cozy Princeville Home with Private Pool, Hot tub and Ocean Views, Beach Gear
Ocean Pool Hale 3br 2ba Cozy Princeville Home with Private Pool, Hot tub and Ocean Views, Beach Gear
House
Princeville, HI, 96722, United States
0.6k from Island Sails center

Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking

3 Bedrooms6 Guests
9.6

Exceptional

53 reviews

$890
Average price / night
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Mahalo Hale -  Private Luxury Resort Property
Mahalo Hale - Private Luxury Resort Property
House
Princeville, HI, 96722, United States
0.6k from Island Sails center

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

4 Bedrooms10 Guests
10.0

Exceptional

8 reviews

$2901
Average price / night
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Paradise retreat! Plunge Pool, Hot Tub,  AC & Water Gears!
Paradise retreat! Plunge Pool, Hot Tub, AC & Water Gears!
House
Princeville, HI, 96722, United States
0.6k from Island Sails center

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

3 Bedrooms11 Guests
9.6

Exceptional

116 reviews

$770
Average price / night
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Hale Moena, Lovely 4 Bedroom Home & Private Pool..on Kauai's Lush North Shore
Hale Moena, Lovely 4 Bedroom Home & Private Pool..on Kauai's Lush North Shore
House
Princeville, HI, 96722, United States
0.6k from Island Sails center

Arcade, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave

4 Bedrooms10 Guests
9.2

Superb

63 reviews

$1099
Average price / night
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Sweeping \"WOW\" Ocean Views from Every Room and Balcony - Penthouse Location
Sweeping \"WOW\" Ocean Views from Every Room and Balcony - Penthouse Location
Condo
Princeville, HI, 96722, United States
0.6k from Island Sails center

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

2 Bedrooms4 Guests
9.8

Exceptional

195 reviews

$629
Average price / night
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Alii Kai I, Mountain View Condo on Spectacular Ocean Cliff
Alii Kai I, Mountain View Condo on Spectacular Ocean Cliff
Condo
Princeville, HI, 96722, United States
0.6k from Island Sails center

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

2 Bedrooms4 Guests
9.8

Exceptional

255 reviews

$276
Average price / night
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Luxury Home With Spectacular 180 Degree White Water Views & Infinity Edge Pool
Luxury Home With Spectacular 180 Degree White Water Views & Infinity Edge Pool
House
Princeville, HI, 96722, United States
0.6k from Island Sails center

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

3 Bedrooms6 Guests
10.0

Exceptional

172 reviews

$2552
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 Island Sails.

Where to stay in Island Sails? Best neighborhoods & areas

Island Sails Vacation Rentals with Private Pool on the Map

Frequently Asked Questions

You can explore 107 verified vacation rentals with a private pool in Island Sails. These include standalone villas and private homes where the pool is reserved exclusively for your group.

Prices for rentals with a private pool in Island Sails vary depending on the property size, location, and travel season. Rates typically start from around $232 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 Island Sails also welcome pets. Currently, 4 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 Island Sails often include additional features such as Pool, Private Pool, and Wellness Facilities. These amenities enhance comfort and create a more relaxing, self-contained stay.

Some family-friendly vacation rentals in Island Sails 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.