Vacation Rentals with Pool in Olomana Three Peaks Trail, HI: Compare 10+ Sites & Save

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  2. Vacation Rentals with Pool
  3.  USA

  4.  Hawaii

  5.  Kailua
  6.  Olomana Three Peaks Trail

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83 Best Vacation Rentals with Pool in Olomana Three Peaks Trail (Starting from $173)

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
3.0k from Olomana Three Peaks Trail center

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

1 Bedroom4 Guests
New to Booking
$173
Average price / night
Check Availability
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
2.9k from Olomana Three Peaks Trail 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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Charming Hale Mokolea in Lanikai 2BR 2BA Full Kitchen
Charming Hale Mokolea in Lanikai 2BR 2BA Full Kitchen
Apartment
Kailua, HI, USA
3.0k from Olomana Three Peaks Trail 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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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
3.3k from Olomana Three Peaks Trail 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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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
3.4k from Olomana Three Peaks Trail center

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

2 Bedrooms4 Guests
New to Booking
$219
Average price / night
Check Availability
Quiet, Private,  Beachy 2-bedroom,  Walk to Kailua Beach, A/C
Quiet, Private, Beachy 2-bedroom, Walk to Kailua Beach, A/C
House
Kailua, HI, 96734, United States
3.4k from Olomana Three Peaks Trail center

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

2 Bedrooms4 Guests
10.0

Exceptional

29 reviews

$273
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
4.1k from Olomana Three Peaks Trail 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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Spacious & Breezy 3 Bedroom Home with Ko'Olau Views and a Pool
Spacious & Breezy 3 Bedroom Home with Ko'Olau Views and a Pool
Apartment
Kailua, HI, 96734, United States
3.4k from Olomana Three Peaks Trail center

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

3 Bedrooms7 Guests
New to Booking
$371
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
4.1k from Olomana Three Peaks Trail 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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Peaceful Hawaii Paradise three minutes from Beautiful Beach in a quaint Town
Peaceful Hawaii Paradise three minutes from Beautiful Beach in a quaint Town
Apartment
Kailua, HI, 96734, United States
3.5k from Olomana Three Peaks Trail center

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

1 Bedroom2 Guests
9.8

Exceptional

20 reviews

$339
Average price / night
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Kailua Beachside home
Kailua Beachside home
House
Kailua, HI, USA
4.2k from Olomana Three Peaks Trail 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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'Star of Hawaii'  Beachside, Pool, Steps to Beach - Great for Families
'Star of Hawaii' Beachside, Pool, Steps to Beach - Great for Families
House
Kailua, HI, 96734, United States
3.7k from Olomana Three Peaks Trail center

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

4 Bedrooms10 Guests
9.4

Superb

98 reviews

$669
Average price / night
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Upscale Kailua Getaway Steps to Swim Beach!
Upscale Kailua Getaway Steps to Swim Beach!
House
Kailua, HI, USA
5.2k from Olomana Three Peaks Trail 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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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
3.8k from Olomana Three Peaks Trail 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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Lanikai Ohana Hale
Lanikai Ohana Hale
House
Kailua, HI, USA
5.4k from Olomana Three Peaks Trail 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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Pool & Beachside—NEW Kailua Luxury Beach House - Direct beach access! 30+ Nights
Pool & Beachside—NEW Kailua Luxury Beach House - Direct beach access! 30+ Nights
House
Kailua, HI, 96734, United States
3.9k from Olomana Three Peaks Trail center

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

2 Bedrooms4 Guests
10.0

Exceptional

2 reviews

$347
Average price / night
Check Availability
Cozy 2-bedroom apartment in charming Kailua with AC steps from the beach.
Cozy 2-bedroom apartment in charming Kailua with AC steps from the beach.
Apartment
Kailua, HI, 96734, United States
4.0k from Olomana Three Peaks Trail center

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

2 Bedrooms3 Guests
New to Booking
$282
Average price / night
Check Availability
Gigi's Retreat-Kailua Beach Front + Pool - Lic.1990/NUC-1783
Gigi's Retreat-Kailua Beach Front + Pool - Lic.1990/NUC-1783
House
Kailua, HI, 96734, United States
4.0k from Olomana Three Peaks Trail center

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

3 Bedrooms10 Guests
10.0

Exceptional

34 reviews

$3308
Average price / night
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Kailua Home Pool & Spa with amazing views
Kailua Home Pool & Spa with amazing views
House
Kailua, HI, 96734, United States
4.1k from Olomana Three Peaks Trail center

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

3 Bedrooms7 Guests
9.8

Exceptional

29 reviews

$339
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
4.1k from Olomana Three Peaks Trail 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
Check Availability
Gorgeous Renovated 1937 Plantation Style Beach House 50 Steps to the Center of the Beach by RedAwning
Gorgeous Renovated 1937 Plantation Style Beach House 50 Steps to the Center of the Beach by RedAwning
House
Kailua, HI, 96734, United States
4.1k from Olomana Three Peaks Trail center

AC, Barbecue, Dryer, Free Parking, Hot Tub, Internet, Laundry, Microwave, No Smoking

5 Bedrooms10 Guests
10.0

Exceptional

4 reviews

$1142
Average price / night
Check Availability
Kailua Beach Villa: Stunning Beachfront Estate Private Pool/Spa, Ocean View & AC
Kailua Beach Villa: Stunning Beachfront Estate Private Pool/Spa, Ocean View & AC
Villa
Kailua, HI, 96734, United States
4.1k from Olomana Three Peaks Trail center

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

5 Bedrooms12 Guests
New to Booking
$2363
Average price / night
Check Availability
Pilipu Palms 2
Pilipu Palms 2
House
Kailua, HI, 96734, United States
4.1k from Olomana Three Peaks Trail center

AC, Free Parking, Internet, Kitchen, No Smoking, Pool

3 Bedrooms5 Guests
New to Booking
$385
Average price / night
Check Availability
Kailua Sands | Oceanfront Pool Retreat with Gym | Sleeps 7
Kailua Sands | Oceanfront Pool Retreat with Gym | Sleeps 7
House
Kailua, HI, 96734, United States
4.2k from Olomana Three Peaks Trail center

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

3 Bedrooms7 Guests
New to Booking
$2750
Average price / night
Check Availability
Kailua Luxury Estate: Licensed Rental #1990/NUC-1787
Kailua Luxury Estate: Licensed Rental #1990/NUC-1787
House
Kailua, HI, 96734, United States
4.2k from Olomana Three Peaks Trail center

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

6 Bedrooms16 Guests
9.8

Exceptional

76 reviews

$4216
Average price / night
Check Availability
Zen Home with AC, Pool, Near Kailua Beach
Zen Home with AC, Pool, Near Kailua Beach
House
Kailua, HI, 96734, United States
4.2k from Olomana Three Peaks Trail center

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

4 Bedrooms12 Guests
9.8

Exceptional

77 reviews

$1067
Average price / night
Check Availability
Beachside Kailua AC 3min to beach - DATES AVAIL! Min Stay 7 Nights-CONTACT HOST
Beachside Kailua AC 3min to beach - DATES AVAIL! Min Stay 7 Nights-CONTACT HOST
House
Kailua, HI, 96734, United States
4.2k from Olomana Three Peaks Trail center

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

4 Bedrooms8 Guests
10.0

Exceptional

98 reviews

$777
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 Olomana Three Peaks Trail.

Where to stay in Olomana Three Peaks Trail? Best neighborhoods & areas

Olomana Three Peaks Trail Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 83 verified vacation rentals with a pool in Olomana Three Peaks Trail. 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 Olomana Three Peaks Trail vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $173 per night, with private pool homes and peak travel periods often costing more.

Many rentals in Olomana Three Peaks Trail 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 Olomana Three Peaks Trail 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 Olomana Three Peaks Trail 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 Olomana Three Peaks Trail 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.