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

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  1. VBOR
  2. Vacation Rentals with Pool
  3.  USA

  4.  Hawaii

  5.  Kailua
  6.  Lanikai Pillboxes Trailhead

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83 Best Vacation Rentals with Pool in Lanikai Pillboxes Trailhead (Starting from $155)

Upscale Kailua Getaway Steps to Swim Beach!
Upscale Kailua Getaway Steps to Swim Beach!
House
Kailua, HI, USA
0.4k from Lanikai Pillboxes Trailhead center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

3 Bedrooms6 Guests
New to Booking
$936
Average price / night
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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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Lanikai Ohana Hale
Lanikai Ohana Hale
House
Kailua, HI, USA
0.9k from Lanikai Pillboxes Trailhead center

Accommodations, Parking, Villas, Vacation homes, Spa, Cottages, Lodgings, Vacation rentals, Places to stay

1 Bedroom4 Guests
New to Booking
$976
Average price / night
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LANIKAI SUITE - Spacious 1-BR 1-BA; located 3 houses from famous LANIKAI Beach
LANIKAI SUITE - Spacious 1-BR 1-BA; located 3 houses from famous LANIKAI Beach
Apartment
Kailua, HI, 96734, United States
0.2k from Lanikai Pillboxes Trailhead center

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

1 Bedroom2 Guests
New to Booking
$155
Average price / night
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Relax at Kapakai Cottage 2-Bedroom Comfort with Full Kitchen & WD
Relax at Kapakai Cottage 2-Bedroom Comfort with Full Kitchen & WD
Apartment
Kailua, HI, USA
1.8k from Lanikai Pillboxes Trailhead center

Apartments, Accommodations, Parking, Cottages, Lodgings, Vacation rentals, Places to stay

2 Bedrooms4 Guests
New to Booking
$219
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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Stylish 1BR Apartment with AC Full Kitchen & WD - Just Steps to the Beach
Stylish 1BR Apartment with AC Full Kitchen & WD - Just Steps to the Beach
Apartment
Kailua, HI, USA
2.6k from Lanikai Pillboxes Trailhead center

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

1 Bedroom4 Guests
New to Booking
$173
Average price / night
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Lanikai Luxury 5 Bedroom Beachfront Estate - limited time OFFER
Lanikai Luxury 5 Bedroom Beachfront Estate - limited time OFFER
House
Kailua, HI, 96734, United States
0.4k from Lanikai Pillboxes Trailhead center

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

5 Bedrooms12 Guests
New to Booking
$1432
Average price / night
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Charming Hale Mokolea in Lanikai 2BR 2BA Full Kitchen
Charming Hale Mokolea in Lanikai 2BR 2BA Full Kitchen
Apartment
Kailua, HI, USA
2.6k from Lanikai Pillboxes Trailhead center

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

2 Bedrooms4 Guests
New to Booking
$273
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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Gorgeous Renovated 1937 Plantation Style Beach House 50 Steps to the Center of the Beach home
Gorgeous Renovated 1937 Plantation Style Beach House 50 Steps to the Center of the Beach home
House
Kailua, HI, USA
2.7k from Lanikai Pillboxes Trailhead center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

5 Bedrooms10 Guests
New to Booking
$2342
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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Kailua Beachside home
Kailua Beachside home
House
Kailua, HI, USA
3.3k from Lanikai Pillboxes Trailhead center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

4 Bedrooms14 Guests
New to Booking
$1890
Average price / night
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Your Perfect Home Charming 2BR2BA Apartment with Full Kitchen WD & AC
Your Perfect Home Charming 2BR2BA Apartment with Full Kitchen WD & AC
Apartment
Kailua, HI, USA
3.4k from Lanikai Pillboxes Trailhead center

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

2 Bedrooms6 Guests
New to Booking
$261
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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Less than 1 min walk to Kailua Beach- NUC#1990/NUC-1760
Less than 1 min walk to Kailua Beach- NUC#1990/NUC-1760
Cottage
Kailua, HI, 96734, United States
0.8k from Lanikai Pillboxes Trailhead center

AC, Barbecue, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Laundry, Living Area

2 Bedrooms5 Guests
9.4

Superb

151 reviews

$522
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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Just steps from the sand—enjoy a pool, hot tub, bikes, beach gear & more!
Just steps from the sand—enjoy a pool, hot tub, bikes, beach gear & more!
House
Kailua, HI, 96734, United States
0.9k from Lanikai Pillboxes Trailhead center

AC, Barbecue, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Laundry, Living Area

2 Bedrooms5 Guests
9.6

Exceptional

218 reviews

$646
Average price / night
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Less than a one minute walk to Kailua Beach, Pool, Bikes, BBQ, A/C, and more
Less than a one minute walk to Kailua Beach, Pool, Bikes, BBQ, A/C, and more
Apartment
Kailua, HI, 96734, United States
0.9k from Lanikai Pillboxes Trailhead center

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

1 Bedroom3 Guests
9.6

Exceptional

149 reviews

$373
Average price / night
Check Availability

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 Pool in Lanikai Pillboxes Trailhead.

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

Lanikai Pillboxes Trailhead Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 83 verified vacation rentals with a pool in Lanikai Pillboxes Trailhead. 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 Lanikai Pillboxes Trailhead vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $155 per night, with private pool homes and peak travel periods often costing more.

Many rentals in Lanikai Pillboxes Trailhead 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 Lanikai Pillboxes Trailhead welcome pets. Currently, 2 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 Lanikai Pillboxes Trailhead often include additional outdoor features such as Pool, View, and Ocean View. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in Lanikai Pillboxes Trailhead 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.