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Kailua Rentals with Pools

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367 apartments in Kailua with pools

Plantation Charm in Kailua

Kailua bungalow

4 bedrooms / 2 bathrooms / sleeps 7

Match: Swimming pool

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Price per night from

$461

Palione Papalani~Steps from Kailua Beach~large, remodeled with pool&spa

Kailua house

6 bedrooms / 5 bathrooms / sleeps 12

Match: Swimming pool

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Price per night from

$1,500

Hale Mokulua ~ with private pool & spa~steps to Lanikai Beach~3 living spaces

Kailua house

5 bedrooms / 5 bathrooms / sleeps 14

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Price per night from

$2,571

Mokulua Aina~Lanikai tropical retreat with pool ~ steps to Lanikai Beach

Kailua house

3 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$1,786

Kailua Shores Estate 8 Bedroom

Kailua house

8 bedrooms / 9 bathrooms / sleeps 16

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Price per night from

$5,109

Bright Kailua House w/Pool & Patio by Beaches

Kailua house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 11 minutes

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Price per night from

$196

Unforgettable Beachfront Oasis

Kailua villa

6 bedrooms / 5 bathrooms / sleeps 12

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Price per night from

$1,872

Kailua Beach Studio - Coral Room

Kailua studio

Studio / 1 bathroom / sleeps 4

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Price per night from

$89

Garden of Dreams - swimming pool on property

Kailua house

1 bedroom / 1 bathroom / sleeps 2

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Price per night from

$97

Tropical Garden Cottage

Kailua cottage

1 bedroom / 1 bathroom / sleeps 2

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Price per night from

$70

Tropical Garden Studio - Pool on property

Kailua house

1 bedroom / 1 bathroom / sleeps 2

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Price per night from

$61

Place in Paradise~Kailua Beach Front ~ Large private home sleeps up to 14.

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 and large groups who like a bit of space. The property manager is a legend and makes the best bread pudding on the planet. If you're after a vacation/holiday to remember, this is it! Highly, highy recommend. Cheers, Johno.

Match: Swimming pool

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Price per night from

$1,500

Absolutely Oceanfront - Legal - 60ft waterfall lap pool - $199

Kailua house

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 2 hours 52 minutes

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Price per night from

$233

Kailua Surf Paradise Hale, pool

Kailua house

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 1 hour 19 minutes

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Price per night from

$329

Absolutely Oceanfront - NOW $199 -Kailua Studio with 2 decks - Legal

Kailua house

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 2 hours 41 minutes

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Price per night from

$231

Great rentals within 20 miles that match your search

2 Bedroom/Full Kitchen/1.5 bath/sleeps 7/Pool/Hot tub/Sauna/Free Parking/

Honolulu condo

2 bedrooms / 2 bathrooms / sleeps 7

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Price per night from

$340

Ala Moana Condo - 1 Bdrm Ocean View - 24th Fl. !

Honolulu condo

1 bedroom / 1 bathroom / sleeps 4

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Price per night from

$244

Magnificent Ocean View Penthouse Condo in Waikiki

Honolulu apartment

1 bedroom / 1 bathroom / sleeps 5

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Price per night from

$220

Jenny's Cottage Waikiki Ocean view,Romantic,,Central AC, Close to beach. Parking

Honolulu apartment

1 bedroom / 1 bathroom / sleeps 3

“Lovely apartment, lovely location” This was an excellent rental in every respect. The location is wonderful, the property owner is very nice, and the flat itself is comfortable and welcoming. I would recommend it without reservation.

Responds fast! avg. 2 hours 28 minutes

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Price per night from

$170

Ocean, beach, mountain view Double queen beds Jenny's Pineapple Cottage

Honolulu apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 28 minutes

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Price per night from

$267

Jenny's Pineapple Cottage. Deluxe Ocean view ,central AC,parking bathtub

Honolulu apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 28 minutes

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Price per night from

$208

Jenny’s 's Golden Dream Cottage SEA VIEW , Central AC , Parking available

Honolulu apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 28 minutes

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Price per night from

$209

Christmas & New Years 2020 Book Soon!

Honolulu condo

1 bedroom / 1 bathroom / sleeps 4

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Price per night from

$159

2 Bedroom / 1 Bathroom Waikiki Vacation Rental - Sleeps 6!

Honolulu apartment

2 bedrooms / 1 bathroom / sleeps 6

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Price per night from

$209

Ocean and City view condo in the Banyan

Honolulu condo

1 bedroom / 1 bathroom / sleeps 5

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Price per night from

$164

Spacious Waterfront with Gorgeous Views & Private Pool

Kaneohe villa

4 bedrooms / 3 bathrooms / sleeps 12

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Price per night from

$680

Responds fast! avg. 2 hours 18 minutes

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Price per night from

$228

Waikiki 2 Bedroom Suite

Honolulu condo

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$466

Exclusive Boutique Central Waikiki 1BR/1BA Resort

Honolulu apartment

1 bedroom / 1 bathroom / sleeps 5

“Fun and cozy--great price for Waikiki!” I stayed at this property by myself as my husband had to go back to Singapore to work. My sister stayed a night with me and we had a great time here. Its small--I wouldn't probably put more than 2 adults in this unit. There's 2 twin beds and a sofa (can't remember if it turns into a bed or not). Would make a perfect girls getaway. The unit even has a dandy little vanity! The guy who oversees the property is very nice--he's separate from the owners. But he won't tolerate any funny business from the people downstairs at the bar, etc. This condo has a very quiet vibe, and its clear they don't want to be disturbed by partiers. Good security too. So I really appreciated that. Inna is a pleasure to deal with. We stayed in another of her properties in Waikiki and found both that one and this one to be well-cared for. Don't expect super glam--expect a bright and happy little place to stay. The unit has their own wifi so you don't have to sit in the hallway with everyone else who uses the building wifi. So that's a perk. Nice kitchenette. Great location. Don't worry too much about the people down at the bar. I don't recall ever being woken up or disturbed by them. This unit is a great value. I'd def stay here again.

Responds fast! avg. 2 hours 51 minutes

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Price per night from

$116

Astonishing Ocean Front at Ilikai with Diamond Head View

Honolulu apartment

1 bedroom / 1 bathroom / sleeps 4

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Price per night from

$336

2-Bedroom Waikiki Vacation Rental Unit - Sleeps 6!

Honolulu apartment

2 bedrooms / 1 bathroom / sleeps 6

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Price per night from

$210

Waikiki Home on Ala Wai Canal-Close to Beach, Shopping, Entertainment,Everything

Honolulu apartment

3 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 2 hours 34 minutes

Match: Swimming pool

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Price per night from

$175

One of a Kind Luxury Suite w/Amenities.Sleeps 1-5!

Honolulu apartment

1 bedroom / 1 bathroom / sleeps 5

“HOME AWAY FROM HOME!” HOME AWAY FROM HOME! This was my home away from home for 3 weeks in May! I was so happy staying here! If you're staying in Waikiki and need space like I do, single or a couple, or family with kids and don't like small hotel rooms, like me, and want a place to call home, look no further! This is the place I highly recommend. I loved using the pool and gym on that amazing roof space, WOW!!!! Having WIFI in the condo and reception was so helpful. Did not let me down or slow me down, all high speeds, just like home guys! The Location was perfect! Beach, all major hotels, shops, buses, bars, night clubs, sports bars, my new favourite scuba shop all on foot and flip flops. I weaved my way around Waikiki, got to know all the shortcuts to and from the beach. I can tell you this is the perfect spot to be in paradise. Off the main street, away from all the noise. I met a lot of people and they were so envious of me staying in a private condo, in this location, compared to their small space and when I told them what I was paying - need I say more? My host was marvellous with informing details prior to arriving. My perfect holiday!

Responds fast! avg. 2 hours 51 minutes

Match: Swimming pool

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Price per night from

$140

Ocean view condo in Waikiki w/ lanai, free parking & shared pool/tennis/gym!

Honolulu house

3 bedrooms / 2 bathrooms / sleeps 13

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Price per night from

$500

Waikiki Skytower 2101

Honolulu apartment

1 bedroom / 1 bathroom / sleeps 5

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Price per night from

$205

Waikiki specious apartment

Honolulu apartment

1 bedroom / 1 bathroom / sleeps 2

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Price per night from

$82

Awesome Studio,Great Location,Huge Saving!

Honolulu apartment

1 bedroom / 1 bathroom / sleeps 4

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Price per night from

$133

(Waikiki) Island Colony, Quality Studio w/ocean, city & mountain views!

Honolulu condo

1 bedroom / 1 bathroom / sleeps 2

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Price per night from

$116

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