Vacation Rentals with Private Pool in Lanikai Pillboxes Trailhead, HI: Compare 10+ Sites & Save

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  2. Vacation Rentals with Private Pool
  3.  USA

  4.  Hawaii

  5.  Kailua
  6.  Lanikai Pillboxes Trailhead

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60 Best Vacation Rentals with Private Pool in Lanikai Pillboxes Trailhead (Starting from $461)

Lanikai Breeze: Beautiful Private Home w/Pool, Yard & AC - Walk to the Beach
Lanikai Breeze: Beautiful Private Home w/Pool, Yard & AC - Walk to the Beach
House
Kailua, HI, 96734, United States
0.2k from Lanikai Pillboxes Trailhead center

AC, Balcony, Dryer, Free Parking, Kitchen, Laundry, Microwave, No Smoking, Outdoor Space

5 Bedrooms10 Guests
10.0

Exceptional

6 reviews

$1133
Average price / night
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Hale Lani: Mountainside Ocean View Home | Private Pool & soaking tub with a view
Hale Lani: Mountainside Ocean View Home | Private Pool & soaking tub with a view
House
Kailua, HI, 96734, United States
0.3k from Lanikai Pillboxes Trailhead center

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

3 Bedrooms8 Guests
10.0

Exceptional

3 reviews

$4136
Average price / night
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Enjoy watching for Sea Turtles off your Ocean Front Deck!
Enjoy watching for Sea Turtles off your Ocean Front Deck!
House
Kailua, HI, 96734, United States
0.4k from Lanikai Pillboxes Trailhead center

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

4 Bedrooms10 Guests
10.0

Exceptional

2 reviews

$1460
Average price / night
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Naupaka Hale & Cottage
Naupaka Hale & Cottage
House
Lanikai, HI, 96734, United States
0.4k from Lanikai Pillboxes Trailhead center

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

3 Bedrooms6 Guests
10.0

Exceptional

13 reviews

$1276
Average price / night
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Upscale Kailua Getaway: Steps to Swim Beach!
Upscale Kailua Getaway: Steps to Swim Beach!
House
Kailua, HI, 96734-3109, United States
0.4k from Lanikai Pillboxes Trailhead center

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

3 Bedrooms6 Guests
10.0

Exceptional

3 reviews

$1593
Average price / night
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Spectacular Lanikai Ocean Front w/Pool - newly remodeled, sleeps up to 18!
Spectacular Lanikai Ocean Front w/Pool - newly remodeled, sleeps up to 18!
House
Kailua, HI, 96734, United States
0.5k from Lanikai Pillboxes Trailhead center

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

6 Bedrooms18 Guests
New to Booking
$1806
Average price / night
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Steps to beach, tropical garden and private pool
Steps to beach, tropical garden and private pool
House
Kailua, HI, 96734, United States
0.6k from Lanikai Pillboxes Trailhead center

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

3 Bedrooms6 Guests
9.2

Superb

20 reviews

$650
Average price / night
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Steps to Beach-Heated Pool-AC-Gated Community-Minimum Stay 7 Nights-CONTACT HOST
Steps to Beach-Heated Pool-AC-Gated Community-Minimum Stay 7 Nights-CONTACT HOST
House
Kailua, HI, 96734, United States
0.6k from Lanikai Pillboxes Trailhead center

AC, Barbecue, Dryer, Internet, Kitchen, Laundry, Microwave, No Smoking, Patio

4 Bedrooms8 Guests
10.0

Exceptional

115 reviews

$678
Average price / night
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Resort-like, Kailua Beach, Lanikai Beach, Private Pool, AC, Tropical Retreat
Resort-like, Kailua Beach, Lanikai Beach, Private Pool, AC, Tropical Retreat
House
Kailua, HI, 96734, United States
0.6k from Lanikai Pillboxes Trailhead center

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

3 Bedrooms6 Guests
9.8

Exceptional

73 reviews

$592
Average price / night
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Hale Nani Lanikai: Beautiful Tropical Home Close to Beach w/Pool, Yard & AC
Hale Nani Lanikai: Beautiful Tropical Home Close to Beach w/Pool, Yard & AC
House
Kailua, HI, 96734, United States
0.7k from Lanikai Pillboxes Trailhead center

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

3 Bedrooms8 Guests
10.0

Exceptional

12 reviews

$591
Average price / night
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Kahela - Paradise for Rent
Kahela - Paradise for Rent
House
Kailua, HI, 96734, United States
0.8k from Lanikai Pillboxes Trailhead center

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

4 Bedrooms8 Guests
9.8

Exceptional

51 reviews

$665
Average price / night
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Orchid House - Pool and Endless Ocean views!
Orchid House - Pool and Endless Ocean views!
House
Kailua, HI, 96734, United States
0.8k from Lanikai Pillboxes Trailhead center

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

3 Bedrooms7 Guests
10.0

Exceptional

1 reviews

$1020
Average price / night
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3,200 sq ft House with Pool, 6 Bedrooms, walking distance to Kailua and Lanikai
3,200 sq ft House with Pool, 6 Bedrooms, walking distance to Kailua and Lanikai
House
Kailua, HI, 96734, United States
0.8k from Lanikai Pillboxes Trailhead center

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

6 Bedrooms15 Guests
10.0

Exceptional

4 reviews

$1206
Average price / night
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Steps from Kailua Beach, heated pool, gazebo, AC,  NO CLEANING FEE!
Steps from Kailua Beach, heated pool, gazebo, AC, NO CLEANING FEE!
House
Kailua, HI, 96734, United States
0.8k from Lanikai Pillboxes Trailhead center

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

4 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$1013
Average price / night
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Quaint Tropical Cottage w/Pool, Lanai & AC, Walk to Beach: Lanikai Ohana Hale
Quaint Tropical Cottage w/Pool, Lanai & AC, Walk to Beach: Lanikai Ohana Hale
House
Kailua, HI, 96734, United States
0.9k from Lanikai Pillboxes Trailhead center

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

1 Bedroom4 Guests
9.6

Exceptional

44 reviews

$751
Average price / night
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Luxury Lanikai Oceanfront Home!
Luxury Lanikai Oceanfront Home!
House
Kailua, HI, 96734, United States
1.0k from Lanikai Pillboxes Trailhead center

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

4 Bedrooms6 Guests
New to Booking
$2017
Average price / night
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Lanikai Cottage: Charming Tropical Oasis w/Private Pool & A/C, Walk to Beach
Lanikai Cottage: Charming Tropical Oasis w/Private Pool & A/C, Walk to Beach
House
Kailua, HI, 96734, United States
1.0k from Lanikai Pillboxes Trailhead center

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

3 Bedrooms6 Guests
10.0

Exceptional

17 reviews

$734
Average price / night
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Leaf House: Lux Retreat w/ Pool, Ocean Views & Outdoor Living Near Lanikai
Leaf House: Lux Retreat w/ Pool, Ocean Views & Outdoor Living Near Lanikai
House
Kailua, HI, 96734, United States
1.0k from Lanikai Pillboxes Trailhead center

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

5 Bedrooms10 Guests
New to Booking
$1263
Average price / night
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Hale Mokulua - Lanikai w/heated pool, spa, steps to Beach!
Hale Mokulua - Lanikai w/heated pool, spa, steps to Beach!
House
Kailua, HI, 96734, United States
1.1k from Lanikai Pillboxes Trailhead center

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

5 Bedrooms14 Guests
10.0

Exceptional

21 reviews

$1121
Average price / night
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Villa Hui Hou: Luxe O'ahu Villa Private Oasis! Gourmet Kitchen & Media Room
Villa Hui Hou: Luxe O'ahu Villa Private Oasis! Gourmet Kitchen & Media Room
House
Kailua, HI, 96734, United States
1.1k from Lanikai Pillboxes Trailhead center

AC, Balcony, Barbecue, Dryer, Fitness Equipment, Free Parking, Kitchen, Laundry, Microwave

5 Bedrooms12 Guests
10.0

Exceptional

1 reviews

$1110
Average price / night
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Hale Aloha: Luxe Waterfront Home, Island Vibe, Private Pool, Near Kailua Beach
Hale Aloha: Luxe Waterfront Home, Island Vibe, Private Pool, Near Kailua Beach
House
Kailua, HI, 96734, United States
1.2k from Lanikai Pillboxes Trailhead center

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

4 Bedrooms8 Guests
9.8

Exceptional

6 reviews

$1641
Average price / night
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Lavish Lanikai Hillside Estate: Oceanview w/Pool/Spa, AC & Mokulua Isle Views
Lavish Lanikai Hillside Estate: Oceanview w/Pool/Spa, AC & Mokulua Isle Views
House
Kailua, HI, 96734, United States
1.4k from Lanikai Pillboxes Trailhead center

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

5 Bedrooms10 Guests
New to Booking
$3655
Average price / night
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Lanikai 5 star LUXURY PRIVATE OCEANFRONT, steps into the sea, pool, spa!
Lanikai 5 star LUXURY PRIVATE OCEANFRONT, steps into the sea, pool, spa!
House
Kailua, HI, 96734, United States
1.4k from Lanikai Pillboxes Trailhead center

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

4 Bedrooms7 Guests
10.0

Exceptional

1 reviews

$3007
Average price / night
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BEACHSIDE LUXURY HOME, AC, HEATED POOL, INQUIRE WITH OWNER FOR DESIRED DATES
BEACHSIDE LUXURY HOME, AC, HEATED POOL, INQUIRE WITH OWNER FOR DESIRED DATES
House
Kailua, HI, 96734, United States
1.6k from Lanikai Pillboxes Trailhead center

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

3 Bedrooms7 Guests
10.0

Exceptional

62 reviews

$1339
Average price / night
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MINUTES TO KAILUA BEACH-FABULOUS POOL  great indoor/ outdoor living
MINUTES TO KAILUA BEACH-FABULOUS POOL great indoor/ outdoor living
House
Kailua, HI, 96734, United States
1.6k from Lanikai Pillboxes Trailhead center

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

2 Bedrooms4 Guests
9.6

Exceptional

8 reviews

$461
Average price / night
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Wow!   Home just steps from the Beach with Private Salt Water Pool
Wow! Home just steps from the Beach with Private Salt Water Pool
House
Kailua, HI, 96734, United States
1.8k from Lanikai Pillboxes Trailhead center

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

5 Bedrooms10 Guests
9.6

Exceptional

43 reviews

$1281
Average price / night
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Large, beautiful, updated home w/pool, AC,mins from beach in Kailua!
Large, beautiful, updated home w/pool, AC,mins from beach in Kailua!
House
Kailua, HI, 96734, United States
2.2k from Lanikai Pillboxes Trailhead center

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

7 Bedrooms14 Guests
10.0

Exceptional

25 reviews

$981
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 Lanikai Pillboxes Trailhead.

Where to stay in Lanikai Pillboxes Trailhead? Best neighborhoods & areas

Lanikai Pillboxes Trailhead Vacation Rentals with Private Pool on the Map

Frequently Asked Questions

You can explore 60 verified vacation rentals with a private pool in Lanikai Pillboxes Trailhead. These include standalone villas and private homes where the pool is reserved exclusively for your group.

Prices for rentals with a private pool in Lanikai Pillboxes Trailhead vary depending on the property size, location, and travel season. Rates typically start from around $461 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 Lanikai Pillboxes Trailhead also welcome pets. Currently, 2 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 Lanikai Pillboxes Trailhead often include additional features such as Wellness Facilities, Kitchen, and Laundry. These amenities enhance comfort and create a more relaxing, self-contained stay.

Some family-friendly vacation rentals in Lanikai Pillboxes Trailhead 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.