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Kailua Rentals with Pools

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Kailua Rentals with Pools

673 vacation rentals

Tropical Kailua Studio on the Water w/Private Pool

Kailua house

/ 1 bathroom / sleeps 5

Price per night from

$171

1 / 12

Tranquil Tropical Beach Retreat

Kailua house

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 3 hours 0 minutes

Price per night from

$342

1 / 33

Kailua Guesthouse with Pool and Views!

Kailua cottage

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 1 hour 16 minutes

Price per night from

$487

1 / 24

Plantation Charm in Kailua

Kailua bungalow

4 bedrooms / 2 bathrooms / sleeps 7

“Accommodating!!” The owners were a lifesaver. We were stranded in Hawaii with our family of 6 celebrating our daughter's college graduation and the rental I booked online was a scam!!! We needed accommodations ASAP and the owners moved their schedules

Responds fast! avg. 3 hours 36 minutes

Price per night from

$486

1 / 30

Luxurious 4 BR Kailua Home, Air-Conditioning, Short walk to Beach, Pool!

Kailua house

4 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 25 minutes

Price per night from

$685

1 / 35

Garden of Dreams - swimming pool on property -

Kailua studio

Studio / 1 bathroom / sleeps 2

Responds fast! avg. 1 hour 40 minutes

Price per night from

$100

1 / 21

Tropical Garden Studio - Pool on property

Kailua house

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 1 hour 40 minutes

Price per night from

$111

1 / 17

KAILUA DREAMS-MAKAI: NEW, LUXURIOUS AND SPACIOUS

Kailua apartment

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 1 hour 1 minutes

Price per night from

$281

1 / 23

NEW! Cozy Kailua Studio w/Access to Pool & Patio!

Kailua studio

Studio / 1 bathroom / sleeps 2

Responds fast! avg. 41 minutes

Price per night from

$155

1 / 24

Responds fast! avg. 1 hour 49 minutes

Price per night from

$160

1 / 12

Charming 1 bedroom house

Kailua house

1 bedroom / 1 bathroom / sleeps 2

“Convenient” The house was convenient to everything we wanted to do and see while in Oahu. It was very comfortable, clean, and the owner was easily accessible. We would stay there again.

Responds fast! avg. 2 hours 18 minutes

Price per night from

$166

1 / 12

Loft in Kailua

Kailua house

2 bedrooms / 2 bathrooms / sleeps 2

Responds fast! avg. 1 hour 16 minutes

Price per night from

$258

1 / 16

Steps to Kailua Beach~ 6bdrm ~Palione Papalani~w/private lagoon pool and spa.

Kailua house

6 bedrooms / 5 bathrooms / sleeps 12

Price per night from

$1,500

1 / 35

Shangri La By The Sea

Kailua house

5 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$1,029

1 / 20

NEW! 2BR Kailua Apartment w/ Pool & Patio Access!

Kailua apartment

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 41 minutes

Price per night from

$315

1 / 25

Hale Mokulua~5 bd w/private pool & spa~Steps to Lanikai Beach~3 living spaces

Kailua house

5 bedrooms / 5 bathrooms / sleeps 14

Price per night from

$2,500

1 / 31

Hale Maluhia Lanikai

Kailua house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$1,115

1 / 18

Beautiful Large Contemporary Island Home with pool, walk to the beach

Kailua house

9 bedrooms / 6 bathrooms / sleeps 20

Responds fast! avg. 1 hour 58 minutes

Price per night from

$1,372

1 / 14

Tropical Garden Cottage

Kailua cottage

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 1 hour 40 minutes

Price per night from

$123

1 / 20

Mokulua Aina~3 bd~Lanikai Hawaiian Retreat w/Pool~Steps to White Sand Beach

Kailua house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$1,200

1 / 25

Kailua Shores Estate

Kailua house

8 bedrooms / 9 bathrooms / sleeps 16

Price per night from

$4,500

1 / 16

Hauoli Retreat

Kailua house

6 bedrooms / 3 bathrooms / sleeps 12

Price per night from

$744

1 / 21

Phelps Ohana Rental

Kailua house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$360

1 / 10

NEW! Bright Kailua House w/Pool & Patio by Beaches

Kailua house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 41 minutes

Price per night from

$189

1 / 24

Hale Ainoni

Kailua house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$515

1 / 31

Endless Summer

Kailua house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$567

1 / 32

Home Sweet Home with private pool-Minutes to Beach

Kailua house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 1 hour 16 minutes

Price per night from

$630

1 / 19

Just steps to the beach with private pool. *Monthly rental**

Kailua house

6 bedrooms / 6 bathrooms / sleeps 14

Price per night from

$1,200

1 / 28

Place in Paradise~Kailua~Beachfront~Best Beach~Large 5 bd home~Licensed

Kailua house

5 bedrooms / 5 bathrooms / sleeps 14

“INCREDIBLE!” Best vacation home in Kailua (possibly the world)! The house itself has everything you need and is spacious and luxurious. The location is second to none, with one of the best best beaches right on your doorstep. Great option for families

Price per night from

$1,200

1 / 29

Kalama Beach House

Kailua house

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 52 minutes

Price per night from

$801

1 / 15

Stunning Estate Owned by Paul Mitchell on Lanikai Beach on Oahu!

Kailua villa

7 bedrooms / 7 bathrooms / sleeps 14

Price per night from

$6,000

1 / 39

Fabulous Luxury 5 Bedroom Kailua Beachfront-Private Pool and Spa

Kailua house

5 bedrooms / 5 bathrooms / sleeps 12

Responds fast! avg. 1 hour 16 minutes

Price per night from

$2,353

1 / 24

Absolutely Oceanfront Kailua Vacation Rental- $220

Kailua house

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$342

1 / 26

Stunning Kailua Oceanfront Getaway

Kailua house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$915

1 / 59

Ohana Beachfront Villa - luxury home w/ pool - ID

Kailua house

5 bedrooms / 6 bathrooms / sleeps 10

Price per night from

$5,411

1 / 32

Kailua Surf Paradise Hale, pool

Kailua house

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 1 hour 44 minutes

Price per night from

$630

1 / 16

Shangri-La By The Sea - Tranquil, Gorgeous Stunning views with pool - ID

Kailua house

5 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$1,224

1 / 21

Price per night from

$252

1 / 12
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