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
  • Escape & Treat Yourself..Quiet Clean Bright..5 star reviews, Sleeps 4

    Aloha, this unique Premier Partner property is exclusively available for rental for periods of thirty (30) days or more. Questions, please contact us for the dates you are interested in and we will respond wiki-wiki (fast !).

    This is ...
    Registration Number: 420480020000, TA-120-590-3360-01, GE-120-590-3360-01

    • 1 bedroom
    • 2 bathroom
    • Sleeps 4
    Hawaii> Kailua
    136  reviews
    from $203 
      View Property   Book Now
  • Charming Lanikai Cottage. Contact Owner for Availability and Custom Dates!

    Calendar may not reflect accurate availability. Please contact owner with custom requests.

    Enjoy this lovely and elegant cottage, one short block from world famous Lanikai beach! This beautiful cottage boasts stunning acacia hardwood ...
    Registration Number: TA-123-607-8592-01, GE-123-607-8592-01

    • 1 bedroom
    • 1 bathroom
    • Sleeps 2
    Hawaii> Kailua
    96  reviews
    from $295 
      View Property   Book Now
  • Lanikai Beach Front-Lic #90/TVU-0042 - Views, Beach, Legal Short-term Rental

    Welcome to Walker's Lanikai Beach House. John Walker, was a Scotsman who made his way to Hawaii as a young man in the 1870's to become a contractor of choice to Queen Liliuokalani, and erect such notable buildings as the Bishop Museum and ...
    Registration Number: 430080930000, TA-043-470-0288-01, GE-043-470-0288-01

    • 5 bedroom
    • 4 bathroom
    • Sleeps 14
    Hawaii> Kailua
    111  reviews
    from $2,400 
      View Property   Book Now
  • Kailua Beachfront SHORT-TERM LICENSED RENTAL - Amazing Views, Spacious Home

    Place in Paradise - Kailua offers casual oceanfront accommodations on one of the most beautiful beaches in Hawaii. Kailua Beach has been voted "Best Beach in the United States" by a variety of publications. Five bedrooms and five and half ...
    Registration Number: GE-060-877-8240-01, 430210250000, TA-060-877-8240-01

    • 5 bedroom
    • 6 bathroom
    • Sleeps 14
    Hawaii> Kailua
    190  reviews
    from $2,500 
      View Property   Book Now
  • Steps to Kailua Beach-Heated Pool-Air Conditoned-7 Night Minimum Stay

    This beautiful four bedroom (two luxury master suites, one guest suite and guest bedroom, all air conditioned), four bath Hawaiian style home is just a short walk to pristine Kailua Beach.

    This spacious, estate quality home offers serene ...
    Registration Number: TA-065-681-2032-01

    • 4 bedroom
    • 4 bathroom
    • Sleeps 8
    Hawaii> Kailua
    98  reviews
    from $850 
      View Property   Book Now
  • Steps to Kailua Beach, Immaculate & Private 1 BR. Great Reviews and Value!

    30 day minimum rental due to local laws. We are truly beachside with just two houses between the suite and the private beach gate. Namala Place is a wide street with sidewalks and plenty of parking. We are situated halfway between Kalaheo ...
    Registration Number: 430200660000, GE-078-209-6384-01, TA-078-209-6384-01

    • 1 bedroom
    • 1 bathroom
    • Sleeps 3
    Hawaii> Kailua
    36  reviews
    from $140 
      View Property   Book Now
  • Beachside Kailua AC 3min walk to beach! ASK OWNER for available 2024 dates!

    This airy, spacious four bedroom Kailua beachside vacation rental home with AC provides the essence of tropical Hawaiian living. Recently remodeled kitchen and bath(s) finish off this stunning home. Whether you prefer lounging in the sun ...
    Registration Number: 430190530000, GE-126-659-1744-01, TA-126-659-1744-01

    • 4 bedroom
    • 3 bathroom
    • Sleeps 8
    Hawaii> Kailua
    86  reviews
    from $775 
      View Property   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 ...
    Registration Number: 430050050000, TA-209-884-5696-01, GE-209-884-5696-01

    • 3 bedroom
    • 4 bathroom
    • Sleeps 8
    Hawaii> Kailua
    11  reviews
    from $525 
      View Property   Book Now
  • Walk to beach, 3 bd, 2 bth private house, heated pool, yard, AC, WIFI, parking

    Due to local laws we have a rental contract of 30 days.

    This beautiful, spacious Kailua home has 3 bedrooms and 2 bathrooms. The house can sleep up to 6. Two bedrooms have a King bed and one bedroom has two twin beds. There is also ...
    Registration Number: TA-143-873-0240-01, 430750280000, GE-143-873-0240-01

    • 3 bedroom
    • 2 bathroom
    • Sleeps 6
    Hawaii> Kailua
    127  reviews
    from $320 
      View Property   Book Now
  • 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...
    Registration Number: GE-189-305-8560-01, TA-189-305-8560-01

    • 4 bedroom
    • 4 bathroom
    • Sleeps 8
    Hawaii> Kailua
    6  reviews
    from $865 
      View Property   Book Now
  • Awesome Beachside Cottage Located Just Steps Away from Kailua Beach

    Tropical setting just steps away from beautiful Kailua Beach. Located on a quiet cul-de-sac beachside of Kalaheo Ave. This quiet and private accommodation is ideal for 2 couples or a small family. Aprox 900sq ft of indoor living area, complete ...
    Registration Number: TA-036-719-8208-01, GE-036-719-8208-01

    • 2 bedroom
    • 2 bathroom
    • Sleeps 4
    Hawaii> kailua
    117  reviews
    from $295 
      View Property   Book Now
  • Private Beachfront Rental

    2 Night Minimum Stay
    10 night Maximum Stay

    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. ...
    Registration Number: GE-168-049-0496-01, 430180480000, TA-168-049-0496-01

    • 1 bedroom
    • 1 bathroom
    • Sleeps 2
    Hawaii> Kailua
    196  reviews
    from $320 
      View Property   Book Now
  • Private, beachfront apartment in Lanikai with stunning ocean views!

    *Our calendar may not reflect our current availability. Please feel free to reach out with any questions regarding quotes for our monthly rates, fees and availability at lanikaisunrise808@gmail.com

    Perfectly situated and private with ...
    Registration Number: 430050510000, GE-183-951-1552-01, TA-183-951-1552-01

    • 2 bedroom
    • 1 bathroom
    • Sleeps 4
    Hawaii> Kailua
    48  reviews
    from $350 
      View Property   Book Now
  • Secluded Beach Bungalow with Private Garden

    Aloha! We renovated this old-style Hawaiian home so that it will have the charm of old Hawaii with modern conveniences.

    This garden oasis (we've planted over 3,000 trees and plants) is in the most awesome location - situated right at the ...
    Registration Number: GE-077-835-2640-01, TA-077-835-2640-01, 430110790000

    • 1 bedroom
    • 1 bathroom
    • Sleeps 2
    Hawaii> Kailua
    29  reviews
    from $218 
      View Property   Book Now
  • 10min stroll to Kailua Beach -Split Aircon/wireless/kitchen/solar

    QUIET LOCATION: Secluded on the side of our Kailua home you’ll find Holiday Palms. This private cottage is a remodeled, 600 sq ft, one-bedroom unit, steps from beautiful Kailua Beach. Tucked away amid tropical palm trees, with your own shady ...
    Registration Number: GE-091-387-9040-01, TA-091-387-9040-01

    • 1 bedroom
    • 1 bathroom
    • Sleeps 5
    Hawaii> Kailua
    112  reviews
    from $98 
      View Property   Book Now
  • Licensed Lanikai Garden Studio since 1985 - 100 Yards to Lanikai Beach! w/AC!

    Indulge in the tranquility of Lanikai Beach, just a stone's throw away, and let the allure of this coastal paradise wash over you. With the studio's inviting comforts and the endless ocean possibilities at your disposal, your stay promises to be...
    Registration Number: GE-095-917-0560-01, TA-095-917-0560-01, 143005018000

    • 0 bedroom
    • 1 bathroom
    • Sleeps 2
    Hawaii> Kailua
    47  reviews
    from $350 
      View Property   Book Now
  • Beachside 🏖 Family, vacation home with pool 🌺 NO CLEANING FEE!

    This Kailua, beachside, pool home was completely remodeled in 2019 with all new kitchen, bathrooms, pool house, pool surround, landscaping, TV's, furnishings, etc. And NO CLEANING FEE on 30 day bookings!

    Each room has an individually ...
    Registration Number: GE-174-185-2672-01, TA-174-185-2672-01, 430190450000

    • 5 bedroom
    • 4 bathroom
    • Sleeps 10
    Hawaii> Kailua
    7  reviews
    from $909 
      View Property   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-027-765-7600-01

    • 4 bedroom
    • 3 bathroom
    • Sleeps 8
    Hawaii> Kailua
    49  reviews
    from $1,500 
      View Property   Book Now
  • Amazing 🌺 Kailua Beach House 🌺 Pool! Game Room! 1 House from Beach

    ALOHA! The Kailua Bliss Beach House is a casual and relaxed beach house in the quiet Beachside neighborhood in Kailua, located on a private street, 1 house from the white sands of Kailua beach (Private beach gate is located adjacent to our ...
    Registration Number: TA-068-883-0976-01, GE-068-883-0976-01, 143018061000

    • 4 bedroom
    • 4 bathroom
    • Sleeps 10
    Hawaii> Kailua
    27  reviews
    from $825 
      View Property   Book Now
  • Kolea Landing Modern Beach House w/ Double Suite and Third Bedroom Option

    Aloha and Welcome to Kolea Landing
    A short walk (less than 400 steps to be exact) and you will be relaxing at Lanikai Beach! Our 2,200 sf guest house is the perfect blend of island and modern living. Our guest house has a master bedroom ...
    Registration Number: 430070230000, GE-082-679-2448-01, TA-082-679-2448-01

    • 3 bedroom
    • 2 bathroom
    • Sleeps 6
    Hawaii> Kailua
    74  reviews
    from $542 
      View Property   Book Now
  • Lanikai Hale - 2 cottages to rent together or separately - sleeps up to 12

    Welcome to Lanikai Hale ~ Two Hawaiian style cottages (which can be rented together or separately) 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 ...
    Registration Number: TA-107-927-8080-01, GE-107-927-8080-01

    • 5 bedroom
    • 3 bathroom
    • Sleeps 12
    Hawaii> Kailua
    26  reviews
    from $995 
      View Property   Book Now
  • Steps to quiet part of Kailua beach, renovated, entire home, A/C, perfection

    We have many, many 5 star reviews from another popular website which we were only using until recently. I can share those with you. We have decided to start using VRBO more often so please disregard the lack of reviews and booking acceptance....
    Registration Number: 430250610000, TA-179-364-9152-01, GE-179-364-9152-01

    • 3 bedroom
    • 1 bathroom
    • Sleeps 8
    Hawaii> Kailua
    1  reviews
    from $400 
      View Property   Book Now
  • Large, beautiful, updated home w/pool, AC, mins from beach in Kailua!

    Welcome to Holoholo Hale in the beautiful town of Kailua on the island of Oahu. Kailua is the home of two of the best beaches in the world, Kailua Beach Park and Lanikai Beach. The home is a short drive to all the island has to offer including ...
    Registration Number: 420560420000, GE-141-882-0096-01, TA-141-882-0096-01

    • 7 bedroom
    • 4 bathroom
    • Sleeps 14
    Hawaii> Kailua
    23  reviews
    from $1,023 
      View Property   Book Now
  • 3,200 sq ft House with Pool, 6 Bedrooms, walking distance to Kailua and Lanikai

    The Pool House in Kailua offers 3,200 sq ft with 6 bedrooms, 4 baths and one amazing pool. Located in a peaceful and lush neighborhood with views of the Ko’olau Mountain range, it is an easy walk to Kailua Beach, Lanikai Beach and Buzz's ...
    Registration Number: 420540580000, TA-036-329-7280-01, GE-036-329-7280-01

    • 6 bedroom
    • 4 bathroom
    • Sleeps 15
    Hawaii> Kailua
    3  reviews
    from $748 
      View Property   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 ...
    Registration Number: GE-168-049-0496-01, 430180480000, TA-168-049-0496-01

    • 1 bedroom
    • 1 bathroom
    • Sleeps 2
    Hawaii> Kailua
    88  reviews
    from $320 
      View Property   Book Now
  • Beautiful Beachside Bungalow

    LOCATION LOCATION LOCATION.....
    Enter Paradise
    Relax and Enjoy the Gentle Breezes of Kailua…
    The Original Kailua Beach Bungalow is elegantly renovated with a spacious open floor plan. Modern design mingles with Hawaiian tradition - ...
    Registration Number: TA-064-669-6960-02, GE-064-669-6960-02

    • 1 bedroom
    • 1 bathroom
    • Sleeps 2
    Hawaii> Kailua
    12  reviews
    from $585 
      View Property   Book Now
  • Coconut Grove Kailua Vacation Home

    This adorable pup-friendly, 3 bedroom, 1 bath vacation rental is ideally located, walking/biking distance to both the quaint shops and eateries of Kailua Town and renowned Kailua Beach! Fill your days with walks on the beach, surfing, SUP or ...
    Registration Number: TA-006-886-2976-01, 4306304400000, GE-006-886-2976-01

    • 3 bedroom
    • 1 bathroom
    • Sleeps 6
    Hawaii> Kailua
    1  reviews
    from $233 
      View Property   Book Now
  • Luxury Coconut Grove, Kailua Vacation Home

    Bright and airy home with ample large windows to let in the fresh ocean breeze. Brand new built in 2021! Spacious rooms with a beautiful kitchen to prepare your favorite island dishes. Downstairs 3 bedroom 1 bath lockout unit also available. ...
    Registration Number: 4306304400000, TA-006-886-2976-01, GE-006-886-2976-01

    • 4 bedroom
    • 2 bathroom
    • Sleeps 8
    Hawaii> Kailua
    1  reviews
    from $300 
      View Property   Book Now
  • Beautiful Kailua Hale Studio

    This spacious studio is a permitted short term rental unit conveniently located in Kailua. Walking distance to Kailua Beach, Kailua Town, shopping and restaurants.

    Free on-site parking
    Memory foam queen bed.
    Full kitchenette. ...
    Registration Number: GE-121-728-3584-01, TA-121-728-3584-01, 143071110000

    • 1 bedroom
    • 1 bathroom
    • Sleeps 2
    Hawaii> Kailua
    46  reviews
    from $314 
      View Property   Book Now
  • Steps from Kailua Beach, heated pool, spa, gazebo, AC, NO CLEANING FEE!

    This stylish, designer decorated, 4 bed, 4 Bath home is just across the street from Kailua Beach. We call her Coastal Soul. Lounge in the beach chic living room, cook in the gourmet, fully equipped kitchen, or swim in the heated lagoon pool. ...
    Registration Number: GE-018-450-1760-01, TA-018-450-1760-01, 430100190001

    • 4 bedroom
    • 4 bathroom
    • Sleeps 8
    Hawaii> Kailua
    1  reviews
    from $879 
      View Property   Book Now