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.

List
Map
  • Kailua Beach Hideaway TA-189-305-8560-01

    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 private, this home embodies the true island lifestyle. Walk or jog the long stretch of beach or ...
    Registration Number: TA-189-305-8560-01, GE-18

    • 4 bedroom
    • 4 bathroom
    • Sleeps 8
    HI> Kailua
    30 night min stay3  reviews
    from $667 per night
      Book Now
  • Chateau Relaxo - 2 Bed Kailua Home with Mountain/Lake Views

    Quaint Kailua…Entire 2 bedroom guesthouse on 2nd story (no home below) with gorgeous mountain and lake views. Minutes to everything Kailua has to offer. Near 4 of the country’s best beaches, 5 stunning golf courses, hiking, water sports, ...
    Registration Number: TA-129-625-2928-01, 42083

    • 2 bedroom
    • 1 bathroom
    • Sleeps 4
    HI> Kailua
    5 night min stay1  reviews
    from $528 per night
      Book Now
  • Kailua guest suite ($4200 Monthly stay)

    Beautiful attached guest suite. This Private guest suite has a full kitchen, washer/dryer, stainless steel appliances and a walk in glass shower. It has its own separate private entrance. There is also plenty of street parking. The suite is a ...
    Registration Number: TA-195-394-1594-02, GE-19

    • 1 bedroom
    • 1 bathroom
    • Sleeps 3
    HI> Kailua
    5 night min stay5  reviews
    from $185 per night
      Book Now
  • Beachfront Hawaiian private villa premium location on USNo1 Beach

    "Kai Lua" means Cave in the ocean in Hawaiian language, Polynesian hide their most valuable treasure into the cave under the water, the only way to find it is to diving down into the crystal water and know exactly where you hide these gems, this...
    Registration Number: TA-187-952-4532-01, 14301

    • 3 bedroom
    • 2 bathroom
    • Sleeps 25
    HI> Kailua
    1 night min stay1  reviews
    from $1,698 per night
      Book Now
  • Near Beach, Restaurants, Free WiFi, A/C, TV, Cont'l Breakfast & Onsite Parking

    (30) FIVE STAR GOOGLE REVIEWS AND DAILY CONTINENTAL BREAKFAST PROVIDED. Our home has 2 fully licensed, SEPARATE B & B suites, each is 1 bedroom and 1 bath (walk in shower) & accommodates up to 2 people. Both have their own private entrance, ...
    Registration Number: TA-059-777-1264-01, GE-05

    • 0 bedroom
    • 1 bathroom
    • Sleeps 2
    HI> Kailua
    5 night min stay6  reviews
    from $205 per night
      Book Now
  • Steps to Kailua Beach (30 day rental)

    This cute little beach house is just seconds away from famous Kailua beach! Take a plunge into the ocean, or a short walk through the beach park and trail along right on into Lanikai. This beach house is all about Location! You can see the beach...
    Registration Number: TA-094-358-3232-01, GE-09

    • 3 bedroom
    • 1 bathroom
    • Sleeps 6
    HI> Kailua
    4 night min stay7  reviews
    from $435 per night
      Book Now
  • "The Nene Nest"-A Kailua Lakefront Gem with Mountain/Lake Views

    Extra large studio apartment sits right on Enchanted Lake and offers gorgeous views with wetland habitats. Relax to the max! Minutes to everything Kailua has to offer. Near 4 of the country's best beaches, 5 stunning golf courses, hiking, ...
    Registration Number: TA-129-625-2928-01, 42083

    • 1 bedroom
    • 1 bathroom
    • Sleeps 2
    HI> Kailua
    5 night min stay5  reviews
    from $395 per night
      Book Now
  • Tropical Pool Cottage close to Kailua Beach

    Light and airy one room cottage with queen sized bed, bath, kitchenette, out door sitting area by the pool. The sun provides for 70 % electricity used in this eco friendly Cottage. The lanai overlooks the tropical garden and the salt water ...
    Registration Number: TA-136-919-6544-01

    • 1 bedroom
    • 1 bathroom
    • Sleeps 2
    Hi> Kailua
    1 night min stay1  reviews
    from $103 per night
      Book Now
  • 10% OFF - Pristine Cozy 1000 sqf 1 bdrm aprt With Sweeping Views of Kailua

    Hawaii GET # GE-197-713-5104-01 and TAT Tax ID# TA-197-713-5104-01 Aloha! We are in compliance with Honolulu City and County Ordinance 18-19 (Bill 89), we welcome 30 day renters. Stays less than 30 days are also welcome, if they are the only ...
    Registration Number: TA-197-713-5104-01, GE-19

    • 1 bedroom
    • 1 bathroom
    • Sleeps 4
    HI> Kailua
    29 night min stay55  reviews
    from $195 per night
      Book Now
  • Air conditioned Hi'ilani Hideaway with full kitchen - sleeps up to 4 adults

    Take advantage of our vacation rental in Kailua Oahu, and enjoy a family style atmosphere where you are provided with all of the comforts of home. Whether it be barbecuing under the covered lanai, or taking a walk to our award winning beaches, ...
    Registration Number: TA-065-136-8448-01

    • 2 bedroom
    • 1 bathroom
    • Sleeps 5
    Hi> Kailua
    1 night min stay1  reviews
    from $137 per night
      Book Now
  • Beautiful Tropical Home Close to Beach w/Pool, Yard & AC: Hale Nani Lanikai

    Nestled in the highly sought after wonderful Lanikai community, this beautiful executive home was newly built in 2014. This home is a perfect vantage point. It boasts 3 bedrooms en suite that are generous in size and more than ample in comfort....
    Registration Number: TA-209-884-5696-01, GE-20

    • 3 bedroom
    • 4 bathroom
    • Sleeps 8
    HI> Kailua
    10 night min stay8  reviews
    from $1,229 per night
      Book Now
  • PRIVATE BEACHFRONT RENTAL

    Minimum Stay: 2 night Max Night Stay: 8 nights Our Hawaiian Style Vacation Rental apartment is located on Kailua Beach, one of Hawaii's most beautiful of white sand beaches. Kailua Beach has been rated tops among USA's best beaches. The ...
    Registration Number: TA-168-049-0496-01, 43018

    • 1 bedroom
    • 1 bathroom
    • Sleeps 2
    HI> Kailua
    2 night min stay3  reviews
    from $300 per night
      Book Now
  • Island style Homebase * 2 bedroom & 1 bath - Central Air

    TAT: TA-181-128-3968-01 Amazing Mountain Views in a Lush and Peaceful Setting If you appreciate lush and green surroundings you have come to the right place in an exclusive Kailua neighborhood. Kapakai Cottage is a newly renovated modern ...
    Registration Number: TA-181-128-3968-01

    • 2 bedroom
    • 1 bathroom
    • Sleeps 4
    Hi> Kailua
    1 night min stay2  reviews
    from $171 per night
      Book Now
  • Perfect Kailua Vacation at Ka Hale Lai-House of Serenity- pool and spa

    Perfect Kailua Home on 18,000 square feet of land all your own!! Lots of room to spread out!! We have a gorgeous newly tiled Swimming Pool and spa! You are invited to rest and relax in “Ka Hale Lai” , Kailua’s House of Serenity, 5 ...
    Registration Number: TA-027-765-7600-01, GE-02

    • 4 bedroom
    • 3 bathroom
    • Sleeps 8
    HI> Kailua
    5 night min stay16  reviews
    from $1,214 per night
      Book Now
  • New Listing! ~ Lanikai Hale - 5 Bedrooms/3 Baths ~ Sleeps up to 12

    Welcome to Lanikai Hale ~ Two Hawaiian style cottages on a large fenced-in property in the heart of Lanikai, just 2 miles from Kailua Town on the Windward side of Oahu. There is plenty of parking and sleeping space for a group of 10 to 12 ...
    Registration Number: TA-107-927-8080-01, GE-10

    • 5 bedroom
    • 3 bathroom
    • Sleeps 12
    HI> Kailua
    10 night min stay2  reviews
    from $950 per night
      Book Now

Showing 1 of 5 pages.