Kailua Vacation Rentals

Kailua is one of the most popular vacation rental destinations on Oahu, featuring a fantastic white-sand beach. Many of the vacation rental properties in Kailua are oceanfront, which makes Kailua the perfect destination for those looking for privacy or a romantic getaway. You can have your privacy here and in the same time enjoy easy access to shopping malls, restaurants and services. Kailua Beach is ideal for swimming, kayaking and windsurfing. Browse through this fine selection of Kailua vacation rentals below and find your perfect home away from home.

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  • Kailua Beach Hideaway

    Beachfront! The White Sand of Kailua Beach at Your Door! This 4 bedroom, 4 bath, en suite home is the Perfect Tropical Haven. Tucked away and ...
    Registration Number: TA-189-305-8560-01, GE-18

    • 4 bedroom
    • 4 bathroom
    • Sleeps 8
    HI> Kailua
    30 night min stay4  reviews
    $667 per night
      Book Now
  • Kakela Kai, Beachfront Kailua Home, Private, A/C

    This is a well maintained beachfront home set in a security-gated neighborhood. It is decorated with island style rattan furnishings, ceiling ...
    Registration Number: GE-083-865-6000-01, TA-08

    • 4 bedroom
    • 3 bathroom
    • Sleeps 10
    HI> Kailua
    7 night min stay4  reviews
    $1,000 per night
      Book Now
  • White Sands Escape by the Beach

    Aloha! Come and stay with us in the wonderful beach town of Kailua! Please be respectful and read the ENTIRE listing and house rules before ...
    Registration Number: TA-012-452-2496-01, GE-02

    • 1 bedroom
    • 1 bathroom
    • Sleeps 1
    HI> Kailua
    30 night min stay8  reviews
    $60 per night
      Book Now
  • Now with A/C AND the best access to sandy Lanikai Beach!

    HALE LANIKAI Lic# TA-176-161-3824-01 Non-Conforming Use Permit Number 90/TVU-0031and is compliant with Hawaii State Legislation (HB2078) for ...
    Registration Number: GE-176-161-3824-01, TA-17

    • 4 bedroom
    • 4 bathroom
    • Sleeps 8
    HI> Kailua
    1 night min stay9  reviews
    $1,100 per night
      Book Now
  • Unique Oceanfront Home in Gated Community

    Kona Onenalo is a ONE-OF-A-KIND property on the beautiful Kona Coast. There are 12 identical and individual homes in this quiet, gated ...
    Registration Number: GE-092-363-3664-01, TA-09

    • 3 bedroom
    • 3 bathroom
    • Sleeps 6
    HI> Kailua
    5 night min stay44  reviews
    $407 per night
      Book Now
  • Newly- Renovated Designer Studio - Minutes From Kailua Beach

    Our newly renovated studio is the perfect get-away located in the heart of Kailua. Light-filled and breezy this is the perfect space for one or ...
    Registration Number: TA-133-517-5168-01, GE-13

    • 0 bedroom
    • 1 bathroom
    • Sleeps 3
    HI> Kailua
    5 night min stay14  reviews
    $146 per night
      Book Now
  • Lanikai Breeze - Lanikai Kailua Beachside Home

    Just steps away from coveted Lanikai Beach, sits our newest luxury rental - Lanikai Breeze! Brand new construction, built in 2017, this home ...
    Registration Number: GE-056-922-3168-01, TA-05

    • 5 bedroom
    • 5 bathroom
    • Sleeps 10
    HI> Kailua
    7 night min stay4  reviews
    $1,500 per night
      Book Now
  • Newly Built in 2018 - 2 BR 2 BA + Den in Beautiful Kailua

    Built in June 2018, this 1240 sq ft, two-story home offers the perfect combination of island living with modern finishes. The home features two ...
    Registration Number: TA-039-977-8816-01, 43067

    • 2 bedroom
    • 2 bathroom
    • Sleeps 6
    HI> Kailua
    30 night min stay13  reviews
    $200 per night
      Book Now
  • Kehaulani - Lanikai~ Stunning Ocean Views~4 bd private residence

    Enjoy peace and tranquility from this beautifully remodeled home while soaking in the endless, unobstructed views of the Pacific Ocean and ...
    Registration Number: GE-178-839-9616-01, TA-17

    • 4 bedroom
    • 4 bathroom
    • Sleeps 10
    HI> Kailua
    7 night min stay6  reviews
    $1,800 per night
      Book Now
  • Hale Mokulua~5 bd w/private pool & spa~Steps to Lanikai Beach~3 living spaces

    With 3 separate living spaces, this remodeled and updated Lanikai home is ideal to accommodate up to 14 guests. The main house of Hale Mokulua - ...
    Registration Number: GE-005-853-7984-01, TA-00

    • 5 bedroom
    • 6 bathroom
    • Sleeps 14
    HI> Kailua
    7 night min stay4  reviews
    $2,500 per night
      Book Now
  • Kailua Beach House - Exclusive Kailua Beach Vacation Home

    Home Away From Home Nestled in an intimate gated community, Kailua Beach House offers privacy, security and all the comforts you'd look for in an...
    Registration Number: 430100190001, TA-186-740-

    • 4 bedroom
    • 4 bathroom
    • Sleeps 8
    HI> Kailua
    7 night min stay6  reviews
    $1,250 per night
      Book Now
  • *10% discount on stays now-6/14*Kailani Villa-1 block from the beach, ocean & Mokulua views

    Experience the ultimate Hawaiian getaway at Kailani Villa, a modern two-story masterpiece nestled into a lush mountainside in Lanikai. Set back ...
    Registration Number: TA-200-559-6160-01, GE-20

    • 4 bedroom
    • 4 bathroom
    • Sleeps 10
    HI> Kailua
    10 night min stay7  reviews
    $1,600 per night
      Book Now
  • Spectacular Ocean and Mokulua Island Views

    Lovely quiet private studio with gorgeous ocean views from either common deck or your private deck as well as through studio main door. NEW: AC ...
    Registration Number: TA-080-695-9616-01, GE-08

    • 1 bedroom
    • 1 bathroom
    • Sleeps 2
    HI> Kailua
    3 night min stay8  reviews
    $155 per night
      Book Now
  • Swaying Palms - Beachfront Luxury Kailua Estate

    Swaying Palms is a magnificent custom estate on the white sands of beautiful Kailua Beach. Just a twenty minute drive from Honolulu, Kailua is a...
    Registration Number: TA-192-192-7168-01, GE-19

    • 6 bedroom
    • 8 bathroom
    • Sleeps 12
    HI> Kailua
    30 night min stay1  reviews
    $3,067 per night
      Book Now
  • The Perfect Lanikai Retreat With Direct Access To Secluded White Sand Beach!

    Hale Kainalu is a sweet getaway at the end of Lanikai with exclusive secluded beach used by only 5 houses within a gated drive. This beautiful ...
    Registration Number: GE-180-925-6448-01, TA-18

    • 3 bedroom
    • 2 bathroom
    • Sleeps 6
    HI> Kailua
    7 night min stay66  reviews
    $2,150 per night
      Book Now
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