Vacation Rentals with Pool in Kailua

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Filtering by: Swimming pool

775 vacation rentals

(18) Excellent 

12

Tropical Kailua Studio on the Water w/Private Pool

Oahu / Kailua

Kailua house

5 4 nights min

  • sleeps 5
  • 4 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

Price per night from

$149

Price per night from

$149

(1) Very Good 

24

Kailua Guesthouse with Pool and Views!

Oahu / Kailua

Kailua cottage

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Nearest beach 0.8 mi
  • Swimming pool
  • Child Friendly

Price per night from

$425

Responds fast!
avg. 1 hour 14 minutes

Price per night from

$425

(2) Excellent 

33

Tranquil Tropical Beach Retreat

Oahu / Kailua

Kailua house

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Private garden

Price per night from

$299

Responds fast!
avg. 3 hours 42 minutes

Price per night from

$299

(4) Excellent 

35

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

Oahu / Kailua

Kailua house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$599

Responds fast!
avg. 22 minutes

Price per night from

$599

(5) Very Good 

30

Plantation Charm in Kailua

Oahu / Kailua

Kailua bungalow

4 7 5 nights min

  • 4 bedrooms
  • sleeps 7
  • 5 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$425

Responds fast!
avg. 3 hours 37 minutes

Price per night from

$425

24

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

Oahu / Kailua

Kailua studio

Studio 2 2 nights min

  • Studio
  • sleeps 2
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$135

Responds fast!
avg. 1 hour 17 minutes

Price per night from

$135

(9) Excellent 

21

Garden of Dreams - swimming pool on property -

Oahu / Kailua

Kailua studio

Studio 2 min stay varies

  • Studio
  • sleeps 2
  • min stay varies
  • Swimming pool
  • Air conditioning

Price per night from

$84

Responds fast!
avg. 1 hour 14 minutes

Price per night from

$84

(5) Excellent 

23

KAILUA DREAMS-MAKAI: NEW, LUXURIOUS AND SPACIOUS

Oahu / Kailua

Kailua apartment

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.6 mi
  • Swimming pool

Price per night from

$245

Responds fast!
avg. 1 hour 22 minutes

Price per night from

$245

(2) Excellent 

17

Tropical Garden Studio - Free Wifi

Oahu / Kailua

Kailua house

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Swimming pool

Price per night from

$97

Responds fast!
avg. 1 hour 14 minutes

Price per night from

$97

16

Loft in Kailua

Oahu / Kailua

Kailua house

2 2 14 nights min

  • 2 bedrooms
  • sleeps 2
  • 14 nights min
  • Nearest beach 2 mi
  • Swimming pool
  • Air conditioning

Price per night from

$225

Responds fast!
avg. 1 hour 14 minutes

Price per night from

$225

(2) Excellent 

12

Charming 1 bedroom house

Oahu / Kailua

Kailua house

1 2 7 nights min

  • 1 bedroom
  • sleeps 2
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“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.
…see more

Price per night from

$145

Responds fast!
avg. 2 hours 17 minutes

Price per night from

$145

25

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

Oahu / Kailua

Kailua apartment

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$275

Responds fast!
avg. 1 hour 17 minutes

Price per night from

$275

34

Palione Papalani - Steps to Kailua Beach w/private pool and spa. Sleeps 12.

Oahu / Kailua

Kailua house

6 12 min stay varies

  • 6 bedrooms
  • sleeps 12
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$1,600

Price per night from

$1,600

20

Shangri La By The Sea

Oahu / Kailua

Kailua house

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$900

Price per night from

$900

(1) Very Good 

6

Hale Maluhia Lanikai

Oahu / Kailua

Kailua house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

Price per night from

$975

Price per night from

$975

31

Hale Mokulua - Lanikai Beach! Stunning 5 bd. with private pool and hot tub

Oahu / Kailua

Kailua house

5 14 min stay varies

  • 5 bedrooms
  • sleeps 14
  • min stay varies
  • Swimming pool
  • Child Friendly

Price per night from

$2,200

Price per night from

$2,200

14

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

Oahu / Kailua

Kailua house

9 20 5 nights min

  • 9 bedrooms
  • sleeps 20
  • 5 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$1,180

Responds fast!
avg. 1 hour 36 minutes

Price per night from

$1,180

20

Kailua Shores Estate

Oahu / Kailua

Kailua condo

8 18 min stay varies

  • 8 bedrooms
  • sleeps 18
  • min stay varies
  • Swimming pool
  • Child Friendly

Price per night from

$5,173

Price per night from

$5,173

20

Tropical Garden Cottage

Oahu / Kailua

Kailua cottage

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Swimming pool
  • Child Friendly

Price per night from

$103

Responds fast!
avg. 1 hour 14 minutes

Price per night from

$103

25

Mokulua Aina - Lanikai Hawaiian Retreat tropical landscaping & private pool!

Oahu / Kailua

Kailua house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$1,000

Price per night from

$1,000

16

Kailua Shores Estate

Oahu / Kailua

Kailua house

8 16 min stay varies

  • 8 bedrooms
  • sleeps 16
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$4,480

Price per night from

$4,480

19

Home Sweet Home with private pool-Minutes to Beach

Oahu / Kailua

Kailua house

2 4 14 nights min

  • 2 bedrooms
  • sleeps 4
  • 14 nights min
  • Nearest beach 2 mi
  • Swimming pool
  • Child Friendly

Price per night from

$550

Responds fast!
avg. 1 hour 14 minutes

Price per night from

$550

28

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

Oahu / Kailua

Kailua house

6 14 7 nights min

  • 6 bedrooms
  • sleeps 14
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$1,200

Price per night from

$1,200

15

Kalama Beach House

Oahu / Kailua

Kailua house

4 10 7 nights min

  • 4 bedrooms
  • sleeps 10
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$599

Price per night from

$599

(12) Excellent 

29

Place in Paradise - Kailua Beach - Special Fall Rates Available.

Oahu / Kailua

Kailua house

5 14 7 nights min

  • 5 bedrooms
  • sleeps 14
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“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
…see more

Price per night from

$1,600

Price per night from

$1,600

24

Kailua Beachfront Villa – Private Pool – Right on White Sandy Beach

Oahu / Kailua

Kailua villa

5 11 min stay varies

  • 5 bedrooms
  • sleeps 11
  • min stay varies
  • Nearest beach 0 mi
  • Swimming pool
  • Child Friendly

Price per night from

$1,995

Responds fast!
avg. 1 hour 14 minutes

Price per night from

$1,995

39

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

Oahu / Kailua

Kailua villa

7 14 7 nights min

  • 7 bedrooms
  • sleeps 14
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$6,000

Price per night from

$6,000

(1) Excellent 

24

Fabulous Luxury 5 Bedroom Kailua Beachfront-Private Pool and Spa

Oahu / Kailua

Kailua house

5 12 min stay varies

  • 5 bedrooms
  • sleeps 12
  • min stay varies
  • Nearest beach 0 mi
  • Swimming pool
  • Child Friendly

Price per night from

$2,055

Responds fast!
avg. 1 hour 14 minutes

Price per night from

$2,055

(4) Very Good 

26

Absolutely Oceanfront Kailua Vacation Rental- $199

Oahu / Kailua

Kailua house

1 3 3 nights min

  • 1 bedroom
  • sleeps 3
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$299

Price per night from

$299

32

Ohana Beachfront Villa - luxury home w/ pool - ID

Oahu / Kailua

Kailua house

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$4,704

Responds fast!
avg. 2 hours 11 minutes

Price per night from

$4,704

59

Stunning Kailua Oceanfront Getaway

Oahu / Kailua

Kailua house

3 6 6 nights min

  • 3 bedrooms
  • sleeps 6
  • 6 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$775

Price per night from

$775

16

Kailua Surf Paradise Hale, pool

Oahu / Kailua

Kailua house

4 10 7 nights min

  • 4 bedrooms
  • sleeps 10
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$550

Responds fast!
avg. 1 hour 46 minutes

Price per night from

$550

(1) Very Good 

21

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

Oahu / Kailua

Kailua house

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Nearest beach 0.01 mi
  • Swimming pool
  • Child Friendly

Price per night from

$1,066

Responds fast!
avg. 2 hours 11 minutes

Price per night from

$1,066

12

Kailua Ocean View Studio 2 decks-Upgraded-60 foot pool w waterfalls-Wow! $199

Oahu / Kailua

Kailua house

1 3 3 nights min

  • 1 bedroom
  • sleeps 3
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$299

Price per night from

$299

(8) Very Good 

40

Unforgettable Beachfront Oasis

Oahu / Kailua

Kailua house

6 12 7 nights min

  • 6 bedrooms
  • sleeps 12
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Ask about children

Price per night from

$1,500

Price per night from

$1,500

(1) Very Good 

29

Oasis Villa - outdoor kitchen, pool and jacuzzi - ID

Oahu / Kailua

Kailua house

6 18 min stay varies

  • 6 bedrooms
  • sleeps 18
  • min stay varies
  • Swimming pool
  • Child Friendly

Price per night from

$1,305

Responds fast!
avg. 2 hours 57 minutes

Price per night from

$1,305

Great rentals within 20 miles that match your search

Distance approx 6.94 km from Kailua

(12) Very Good 

14

Hale Ikena

Oahu / Kaneohe

Kaneohe apartment

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Ask about children
“The perfect honeymoon” My husband and I were married in September and this was our first stop in Hawaii for our 2 week honeymoon. To say the least we were extremely excited, happy, wonderfully delighted with this rental. The Parsons were very friendly
…see more

Price per night from

$219

Price per night from

$219

Distance approx 9.77 km from Kailua

(1) Excellent 

4

Best Value in Waikiki -

Oahu / Honolulu

Honolulu apartment

1 4 7 nights min

  • 1 bedroom
  • sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.64 mi
  • Swimming pool

Price per night from

$90

Price per night from

$90