Vacation Rentals & Apartments in Kailua

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1,515 apartments

(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

$148

Price per night from

$148

(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

(18) Very Good 

13

Cozy Cottage 5 Minute Walk to Kailua Beach

Oahu / Kailua

Kailua house

1 4 3 nights min

  • 1 bedroom
  • sleeps 4
  • 3 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$124

Price per night from

$124

(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

$297

Responds fast!
avg. 3 hours 42 minutes

Price per night from

$297

(1) Excellent 

18

Affordable Place on the Best Beach in Hawaii

Oahu / Kailua

Kailua house

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Nearest beach 0 mi
  • Child Friendly

Price per night from

$138

Responds fast!
avg. 3 hours 42 minutes

Price per night from

$138

(8) Excellent 

32

Nancy's Kailua Cottage Makai

Oahu / Kailua

Kailua cottage

1 2 30 nights min

  • 1 bedroom
  • sleeps 2
  • 30 nights min
  • Beach / lakeside relaxation
  • Nearest beach 2 mi
  • Child Friendly

Price per night from

$80

Price per night from

$80

(1) Excellent 

16

ON BEAUTIFUL KAILUA BEACH

Oahu / Kailua

Kailua house

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$185

Responds fast!
avg. 2 hours 51 minutes

Price per night from

$185

(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) Excellent 

75

42 feet from Kailua Beach. Available for Thanksgiving and until mid-December

Oahu / Kailua

Kailua house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Beach / lakeside relaxation
  • Child Friendly
“Best Beach Front Home Yet” We've stayed at several beach front homes in Hawaii and California and this one was our favorite. The layout is perfect for families, the view was awesome, and Kailua Beach is one of our favorite beaches. We also loved the
…see more

Price per night from

$1,000

Responds fast!
avg. 1 hour 4 minutes

Price per night from

$1,000

(1) Very Good 

12

Holiday Palms - Private -5 min from Kailua beach

Oahu / Kailua

Kailua cottage

1 5 1 night min

  • 1 bedroom
  • sleeps 5
  • 1 night min
  • Beach / lakeside relaxation
  • Child Friendly
  • Car not necessary

Price per night from

$129

Responds fast!
avg. 2 hours 41 minutes

Price per night from

$129

(7) Excellent 

Certificate of Excellence

14

Perfect Oasis, Steps to the Beach! 100% Solar!

Oahu / Kailua

Kailua cottage

1 2 4 nights min

  • 1 bedroom
  • sleeps 2
  • 4 nights min
“Great cottage in best part of Kailua” We live in Kauai and periodically come to Oahu to visit friends or to for medical appointments. For a recent 4-night trip, we decided to stay in a vacation rental rather than a hotel; we chose Kailua because the b
…see more

Certificate of Excellence

Price per night from

$179

Responds fast!
avg. 2 hours 55 minutes

Price per night from

$179

(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

(38) Very Good 

15

Hale Ohana steps to Kailua Beach

Oahu / Kailua

Kailua house

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.6 mi
  • Car not necessary
“Amazing holiday place to stay!!!” We have rented Tina's apartment twice now from sydney australia and plan on returning yearly. The location is right across the road from the most beautiful beach in Hawaii. Tina is an amazing host making sure the r
…see more

Price per night from

$140

Responds fast!
avg. 3 hours 43 minutes

Price per night from

$140

(2) Excellent 

13

Lanikai Cottage

Oahu / Kailua

Kailua house

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 mi
  • Child Friendly

Price per night from

$348

Price per night from

$348

(2) Excellent 

15

Best Location in Kailua! D&D's Cottage

Oahu / Kailua

Kailua cottage

1 2 min stay varies

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

Price per night from

$108

Responds fast!
avg. 1 hour 14 minutes

Price per night from

$108

(3) Very Good 

7

Sheffield Studio Walk to Kailua Beach or Town

Oahu / Kailua

Kailua b and b

2 min stay varies

  • sleeps 2
  • min stay varies
  • Nearest beach 0.16 mi
  • Ask about children
  • Air conditioning

Price per night from

$134

Price per night from

$134

(5) Excellent 

24

KAILUA DREAMS-PALI, the perfect mix of Beach/Town

Oahu / Kailua

Kailua apartment

1 3 7 nights min

  • 1 bedroom
  • sleeps 3
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.32 mi
  • Air conditioning

Price per night from

$219

Responds fast!
avg. 1 hour 22 minutes

Price per night from

$219

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

$134

Responds fast!
avg. 10 minutes

Price per night from

$134

(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

23

Lovely 2 Bedrooms Homeaway in Kailua Beach Town

Oahu / Kailua

Kailua house

2 6 1 night min

  • 2 bedrooms
  • sleeps 6
  • 1 night min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$178

Responds fast!
avg. 3 hours 14 minutes

Price per night from

$178

(13) Excellent 

Certificate of Excellence

16

Open Air Loft, Steps from beach

Oahu / Kailua

Kailua apartment

1 2 5 nights min

  • 1 bedroom
  • sleeps 2
  • 5 nights min
  • Child Friendly
  • Air conditioning

Certificate of Excellence

Price per night from

$190

Responds fast!
avg. 3 hours 54 minutes

Price per night from

$190

(22) Very Good 

22

4 Bedroom/ 2 Bath Unit -5 Min Walk to Kailua Beach

Oahu / Kailua

Kailua house

4 8 5 nights min

  • 4 bedrooms
  • sleeps 8
  • 5 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning
“Go when want be a householder of HAWAII!!” Parents & kids were enjoyed to stay and we felt we lives in Hawaii. Everything was perfect but one thing we didn't like is blunt knife!!!! Anyway, thanks for Brandyn and her collegues for supporting us to sta
…see more

Price per night from

$325

Price per night from

$325

(3) Excellent 

25

Kailua, Cozy, Spacious Duplex Home

Oahu / Kailua

Kailua house

1 3 min stay varies

  • 1 bedroom
  • sleeps 3
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$150

Responds fast!
avg. 3 hours 27 minutes

Price per night from

$150

(1) Excellent 

12

Ginger studio, private entry/bathroom, near beach

Oahu / Kailua

Kailua studio

Studio 2 3 nights min

  • Studio
  • sleeps 2
  • 3 nights min
  • Nearest beach 0.3 mi
  • Suitable for children age 5+
  • Air conditioning

Price per night from

$90

Price per night from

$90

(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

6

Nice cozy studio3, Enchanted Lake Kailua

Oahu / Kailua

Kailua studio

Studio 2 2 nights min

  • Studio
  • sleeps 2
  • 2 nights min
  • Nearest beach 1 mi
  • Child Friendly
  • Air conditioning

Price per night from

$70

Price per night from

$70

(2) Very Good 

25

Kailua by the Sea Studio

Oahu / Kailua

Kailua room

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.18 mi
  • Ask about children

Price per night from

$171

Price per night from

$171

15

Martins Hale

Oahu / Kailua

Kailua cottage

1 3 min stay varies

  • 1 bedroom
  • sleeps 3
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$195

Price per night from

$195

10

Kailua Beach Wagon

Oahu / Kailua

Kailua camper van

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Child Friendly

Price per night from

$115

Price per night from

$115

21

Kaapuni Kainani

Oahu / Kailua

Kailua house

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 mi
  • Child Friendly

Price per night from

$600

Price per night from

$600

(3) Excellent 

21

Hale Luana

Oahu / Kailua

Kailua cottage

1 2 5 nights min

  • 1 bedroom
  • sleeps 2
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 1 mi
  • Air conditioning

Price per night from

$199

Price per night from

$199

(1) Excellent 

10

The quaint Kailua-Kalama "Cottage"

Oahu / Kailua

Kailua cottage

2 1 night min

  • sleeps 2
  • 1 night min
  • Car not necessary
  • Ask about pets
  • Private garden

Price per night from

$105

Price per night from

$105

(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

(6) Excellent 

15

Nancy's Kailua Cottage Mauka

Oahu / Kailua

Kailua cottage

4 30 nights min

  • sleeps 4
  • 30 nights min
  • Beach / lakeside relaxation
  • Nearest beach 2 mi
  • Child Friendly
“Nancy's is the perfect place to get away from the hustle of Honolulu!” My wife and I recently stayed at Nancy's while on Oahu. It's a short hop across the island in Kailua, about a 20-30 minute drive from Honolulu. The cottage has everything you need,
…see more

Price per night from

$80

Price per night from

$80

(4) Excellent 

13

Beachfront Kailua, Oahu

Oahu / Kailua

Kailua house

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Child Friendly
  • Ask about pets

Price per night from

$447

Price per night from

$447

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

$1,300

Price per night from

$1,300

25

Kehaulani

Oahu / Kailua

Kailua villa

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Ask about children
  • Ask about pets

Price per night from

$960

Responds fast!
avg. 1 hour 27 minutes

Price per night from

$960

24

Kailua House w/Lanai & Grill-1 Mi. from the Beach

Oahu / Kailua

Kailua house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Child Friendly

Price per night from

$340

Responds fast!
avg. 10 minutes

Price per night from

$340

About Kailua

Just a quick drive from the capital of Honolulu and Waikiki Beach, the small coastal town of Kailua is one of Hawaii's most picturesque and accessible beach communities. Overlooking the expansive, sapphire blue Kailua Bay, the town is bordered by a gorgeous white sand beach, often ranked among the best in Hawaii. Bring your book, a beach towel, and a pair of flip flops; you don't need much more to enjoy life in Kailua.

With continuous trade winds rolling off the coast, the climate is always comfortable in sunny Kailua, Hawaii. Thanks to the steady breeze, it is also a great spot for windsurfing and other beach activities, like horseback riding, swimming, kayaking, and snorkeling. If you want to explore the tropical scenery around Kailua, there are also tons of hiking trails in the surrounding Koolau Ridge and the Ka Iwi Ridge.

Here are a few additional suggestions of things to do in Kailua:

  • Kailua Beach Park: An uninterrupted two-mile stretch of white sand and blue sea, Kailua Beach has been repeatedly named one of Hawaii's best beaches.
  • Lanikai: Just outside Kailua, the small community of Lanikai is home to another incredibly beautiful stretch of sand.
  • Honolulu and Waikiki: If you visit Kailua, don't overlook its famous neighbor, the fun capital city of Honolulu.
  • Ka'iwa Ridge Trail: Spend a few hours ascending the Ka'iwa Ridge for fabulous views of Kailua Bay below.
  • Kawainui Marsh: Just outside Kailua, Hawaii's largest wetland and freshwater lagoon is a wonderful place to observe unusual birds and vegetation.
  • Ulupo Heiau State Historic Site: This historic Hawaiian temple was built in the 18th century and is believed to be the former home of several Oahu chiefs.

If you are coming to stay on this piece of paradise, look for a comfortable vacation rental for the family or a luxury villa with ocean views for a romantic getaway. You can also find a condo or apartment for rent, often within walking distance of the waves.