Kailua-Kona Vacation Rentals

Kailua-Kona is the Big Island's top vacation destination. Its sunny climate and pristine beaches make Kailua-Kona the perfect tropical destination for families and couples alike. You will find over 500 vacation rentals here, ranging from affordable studios and one-bedroom condos to spacious upscale apartments, houses and villas. There is so much to see and do in Kailua-Kona. The town is a perfect place for ocean and outdoor recreational activities. If you like watersport adventures, you can go surfing, diving, boating, snorkeling and swimming. If you enjoy shopping, you will find many shops, boutiques, art galleries and restaurants in Kailua-Kona, as well as numerous historical sites.

  • Partial Ocean View Kailua-Kona Condominium

    Condominium in the heart of Kailua-Kona only two blocks from the pier, where the Ironman starts, and we are just a short walk to the Ironman Village. Located just off of Henry Street on Kuakani Highway puts us right on the bike/run route of the ra...

    1 Bedrooms, 1 Bathrooms, Sleeps 4

    HI>Kailua-Kona

    60 USD - 80 USD

    nightly

    375 USD - 550 USD

    weekly

    1,600 USD - 1,900 USD

    monthly

  • Tranquil / Secluded Tropical Hideaway on 7-Acre Estate!!

    Stand-Alone Tranquil Hideaway on seven acres of Organic Kona Coffee, Macadamia Nuts and All Kinds of Tropical Fruit trees. Comfortable (1,0000 ft) elevation with perfect year-round climate! Temperature averages comfortable low 80s daytime to 70s a...

    1 Bedrooms, 1 Bathrooms, Sleeps 2

    HI>Captain Cook

    65 USD - 65 USD

    nightly

    455 USD - 455 USD

    weekly

    1,575 USD - 1,575 USD

    monthly

  • Location, Location. Centrally Located In Kailua-Kona Across From Ocean

    Spacious and comfortable one bedroom unit overlooking pool, ocean view and water fall below. Sleeps four comfortably. Kitchen has been upgraded and includes many of your essentials, home away from home. The unit is conveniently tucked away fro...

    1 Bedrooms, 2 Bathrooms, Sleeps 4

    HI>Kailua-Kona

    67 USD - 169 USD

    nightly

    595 USD - 1,183 USD

    weekly

    1,995 USD - 3,550 USD

    monthly

  • Beautiful Oceanfront Kona Alii Condo on the fifth floor in the heart of town

    Beautiful oceanfront unit in the heart of Kailua Kona on Alii Dr.. It is located on the fifth floor, just across the street from the breaking surf. The large lanai has an incredible 180 degree ocean view and is great for watching dolphins, whal...

    1 Bedrooms, 2 Bathrooms, Sleeps 2

    HI>Kailua-Kona

    73 USD - 189 USD

    nightly

    1,253 USD - 1,323 USD

    weekly

    2,200 USD - 4,470 USD

    monthly

  • Kona Shores - Great Escape to Paradise!

    This lovely second floor condo in Kona Shores is just a mile to all restaurants, cafes and shopping within Kailua Village. From the Ocean Front Pool and BBQ Area you will be able to enjoy our amazing Kona Sunsets, as well as the cruise ships, para...

    0 Bedrooms, 1 Bathrooms, Sleeps 4

    HI>Kailua-Kona

    75 USD - 120 USD

    nightly

    488 USD - 585 USD

    weekly

    1,875 USD - 2,250 USD

    monthly

  • JUMPING DOLPHIN w BREAKFASTn a view

    Very quiet setting, private garden deck , close but tucked away,discounts, peaceful hawaiian home with studios n hawaiian touch , very close to beaches, galleries, aloha live theater, many restaurants, downtown & chocolate/coffee farms Please rea...

    1 Bedrooms, 1 Bathrooms, Sleeps 4

    HI>kailua kona

    76 USD - 76 USD

    nightly

    490 USD - 490 USD

    weekly

  • Hawaiian Style Studio

    Centrally located in North Kona,our studio is 15 minutes from the airport, town, and beaches. Our island home is situated at a cool 1000 foot elevation, in an older neighborhood of large lots, big trees, and no street lights. The studio is on th...

    0 Bedrooms, 1 Bathrooms, Sleeps 2

    HI>Kailua Kona

    79 USD - 79 USD

    nightly

    500 USD - 500 USD

    weekly

  • Ocean View Condo on Alii Drive

    Right in the heart of Kailua-Kona on Alii Lani Drive. Across the street from the Royal Kona Resort this condo provides the ideal location for your Kona vacation. The soothing waters of the swimming pool will cool you after a day in Hawaii's sun. W...

    1 Bedrooms, 1 Bathrooms, Sleeps 4

    HI>Kailua-Kona

    79 USD - 79 USD

    nightly

    525 USD - 525 USD

    weekly

    2,000 USD - 2,000 USD

    monthly

  • Fantastic Studio in Upscale Farming Community

    Enjoy this private guest suite in a luxury home on a 5 acre coffee plantation located far from the main road. A great place to relax after a day at the beach or trip to the many sites of the Big Island. Enjoy the agricultural Tourism on Hawaii ...

    0 Bedrooms, 1 Bathrooms, Sleeps 2

    HI>Holualoa

    79 USD - 79 USD

    nightly

    474 USD - 474 USD

    weekly

    1,659 USD - 1,659 USD

    monthly

  • AFFORDABLE LUXURY! OCEAN VIEW IN TOWN 1 BEDROOM CONDO

    Kailua Village 307, located in historic Kona town (Kailua Kona, HI), offers great opportunity for those who love to be right in the middle of everything! Walk to shops, restaurants, watch the parades or other seasonal festivities, and relax on y...

    1 Bedrooms, 1 Bathrooms, Sleeps 4

    HI>Kailua-Kona

    79 USD - 121 USD

    nightly

    550 USD - 850 USD

    weekly

    2,322 USD - 3,190 USD

    monthly

  • $80 FLASH SPRING DEAL!! Ocean Front Views. Heart of Kona. Walk Everywhere!

    FLASH SPRING DEAL! May 13, 2017 - Jun 30, 2017 Beautiful Downtown Kona...Oceanfront! Read my reviews!!! FREE IN ROOM PRIVATE WiFi . IRONMAN? WATCH FROM THE CONDO LANAI. WALK TO START IN MINUTES! ( I have several IRONMAN UNITS) Budget? OCEAN...

    0 Bedrooms, 1 Bathrooms, Sleeps 2

    HI>Kailua-Kona

    80 USD - 250 USD

    nightly

    800 USD - 800 USD

    weekly

    2,400 USD - 2,400 USD

    monthly

  • Beautiful Condo in Kona, Big Island of Hawaii

    Our 2/2 is newly remodeled. The condo has all new furnishings, comfortable beds, granite counter tops, new appliances, flat screen T.V.'s, and designer touches everywhere. Desirable quiet second floor location. The unit is situated far from all of...

    2 Bedrooms, 2 Bathrooms, Sleeps 4

    HI>Kailua-Kona

    83 USD - 214 USD

    nightly

    2,500 USD - 3,500 USD

    monthly

  • 1 Bedroom Ohana with beautiful ocean views

    Fully furnished 1 bedroom seperate Ohana. Private, quiet, new construction. Close to beaches and town. Beautiful ocean views. Full kitchen, living room, and full bathroom. Double bed sleeps 1 or 2 people. Covered lanai and BBQ. Washer and drier. ...

    1 Bedrooms, 1 Bathrooms, Sleeps 2

    HI>Kailua-Kona

    85 USD - 120 USD

    nightly

    575 USD - 775 USD

    weekly

    1,600 USD - 1,600 USD

    monthly

  • SPECIAL PRICE MAY & JUNE: Lovely One Bedroom With Two Full Baths!

    LESS THAN 25 DAYS CLEANING IS ONLY $150.00 Hawaii, here you come! What else could you ask for, but this centrally located place to enjoy paradise? A super cute & recently remodeled one bedroom condo at the beautiful Kona Pacific condo complex h...

    1 Bedrooms, 2 Bathrooms, Sleeps 4

    HI>Kailua-Kona

    85 USD - 300 USD

    nightly

    565 USD - 2,100 USD

    weekly

    2,250 USD - 3,000 USD

    monthly

  • FALL SPECIALS - One Cool Condo With Pool View

    Aloha Ohana, One Cool Kona Condo is super clean unit with really pretty designer touches. My unit features everything you need to make your stay a pleasant one. It is said a picture is worth a thousand words. so just take a look and you'll be hook...

    0 Bedrooms, 1 Bathrooms, Sleeps 3

    HI>Kailua-Kona

    85 USD - 259 USD

    nightly

    1,813 USD - 1,813 USD

    weekly

  • Big Island Condo available June 15-July 13 Only

    This lofty third-floor unit has vaulted ceilings and views of the ocean and the city. Fully furnished it sleeps 4 [king size bed, pull-out sofa sleeper]. Our unit has no shared walls, so it is quieter than most. Amenities include a full kitchen...

    1 Bedrooms, 1 Bathrooms, Sleeps 4

    HI>Kailua-Kona

    85 USD - 85 USD

    nightly

    550 USD - 550 USD

    weekly

  • Sunny Whale Studio w BREAKFAST a Deck & View

    Our best ocean view and sunnyest unit...Discounts, peaceful hawaiian home with studios n hawaiian touch , very close to beaches, galleries, aloha live theater, many restarants, downtown & chocalate/coffee farms Also can be made to 2b,3b,4b,5b an...

    2 Bedrooms, 1 Bathrooms, Sleeps 4

    HI>kailua kona

    86 USD - 86 USD

    nightly

    566 USD - 566 USD

    weekly

  • Charming Kona Studio's just a short walk to town

    Brand new house designed in an open air plantation/octagon style. In these Kona rentals, each room is decorated with Hawaiian plantation charm and includes a partial kitchen, eating area, cable television, wireless internet, queen bed and private ...

    0 Bedrooms, 1 Bathrooms, Sleeps 2

    HI>Kailua Kona

    89 USD - 89 USD

    nightly

    575 USD - 575 USD

    weekly

  • Very affordable summer dates available. Perfect base for your Hawaii adventure.

    Situated in the pristine landscaped grounds of the Keauhou Kona Surf and Racquet Club, the number 2 rated accomodation in the Kailua-Kona area, our Kailua-Kona, Hawaii vacation rental condo is an ideal place to holiday at with family or friends. O...

    2 Bedrooms, 2 Bathrooms, Sleeps 6

    HI>Kailua-Kona

    89 USD - 139 USD

    nightly

    833 USD - 973 USD

    weekly

  • Rainbow B&B - a peaceful tropical retreat

    Notice ! We have 5 guestrooms. Even if it shows as full here we may have open rooms. Please contact us for correct availability ! The Rainbow Plantation B&B is located on a large 3.5 Acre tropical property, south of Kailua-Kona near Captain Cook ...

    5 Bedrooms, 5 Bathrooms, Sleeps 22

    HI>Captain Cook

    89 USD - 129 USD

    nightly

    450 USD - 774 USD

    weekly

    1,300 USD - 2,199 USD

    monthly

  • Lovely 1b/1b, sleeps 4, wifi, pool, oceanfront complex

    Amazing 1 bedroom/1 bathroom unit. Enjoy the fragrant scent of tropical flowers, the beautiful sound of the ocean and view of the beautiful pool from the Lani. The unit comes completely furnished with everything you should need to enjoy your stay ...

    1 Bedrooms, 1 Bathrooms, Sleeps 4

    HI>Kailua-Kona

    90 USD - 140 USD

    nightly

    550 USD - 850 USD

    weekly

    2,025 USD - 2,800 USD

    monthly

  • Stunning Beach Front, Walking Distance To Town, Beautiful views and sunsets!

    Stunning coastal/beach front condo with blue waves crashing on lava shoreline. Pool, hot tub, barbecue, tennis court, workout area, ping-pong, full kitchen and laundry, newly remodeled, very clean and bright. One king bed and a pull out couch pl...

    1 Bedrooms, 1 Bathrooms, Sleeps 4

    HI>Kailua-Kona

    90 USD - 125 USD

    nightly

    630 USD - 630 USD

    weekly

  • Appealing one bedroom two bathroom oceanview condo, Keauhou Akahi #41, in Keauhou.

    Experience the Hawaiian charm and privacy this upgraded top floor unit has to offer! This beautiful and well maintained 1 bed 2 bath unit overlooks the scenic fairways with ocean views beyond - it's private, comfortable and really shows pride of o...

    1 Bedrooms, 2 Bathrooms, Sleeps 4

    HI>Kailua Kona

    630 USD - 1,050 USD

    weekly

    2,700 USD - 4,500 USD

    monthly

    90 USD - 150 USD

    nightly

  • Kona Big Island Oceanfront Complex - Alii Villas

    Second floor condo with great ocean views. This condo offers all the comforts of home in a tropical paradise. Enjoy the beautiful pool with amazing ocean views. Have a great family BBQ while listening to the waves just a few yards away. This co...

    1 Bedrooms, 1 Bathrooms, Sleeps 2

    HI>Kailua-Kona

    604 USD - 1,386 USD

    weekly

    92 USD - 162 USD

    nightly

    2,497 USD - 4,966 USD

    monthly

  • Clean, comfortable and accross from the ocean $595/wk

    Nestled at the foot of Hualalai Volcano Kailua Kona had its beginning as a tiny fishing village. We are directly across the 2 lane street (Alii Dr)from the ocean Today you will still find that small village feeling and the Aloha Spirit alive and w...

    1 Bedrooms, 1 Bathrooms, Sleeps 4

    HI>Kailua-Kona

    94 USD - 100 USD

    nightly

    595 USD - 625 USD

    weekly

    2,150 USD - 2,400 USD

    monthly

  • IN TOWN 1 BEDROOM 2 BATH CONDO! AFFORDABLE

    Malia Kai #8 is located in a small condo community right in town. In the lovely interior garden is a sparkling pool and beautiful tropical landscaping. Malia Kai has 3 levels: the entry with adjacent laundry room, the second floor main living ar...

    1 Bedrooms, 2 Bathrooms, Sleeps 4

    HI>KAILUA KONA

    95 USD - 121 USD

    nightly

    595 USD - 850 USD

    weekly

    2,000 USD - 2,500 USD

    monthly

  • BEAUTIFUL KONA SUNSETS AND A SHORT STROLL TO TOWN

    OUR UNIT OFFERS THE FOLLOWING: - Beautiful Ocean and Sunset View - Corner Third Top Floor Unit - No Elevator - 48" 4k TV with basic cable and BluRay DVD/CD player - Free WiFi - Ceiling Fans - Free Assigned Parking Right Next to Building - King Siz...

    1 Bedrooms, 1 Bathrooms, Sleeps 4

    HI>Kailua-Kona

    95 USD - 95 USD

    nightly

    625 USD - 650 USD

    weekly

  • Condo in Casa De Emdeko Oceanfront Condominium Complex

    The Casa De Emdeko oceanfront complex is located on Alii Drive, 2 miles south of downtown Kailua-Kona and approximately 15 minutes from the airport. Relax on the sandy sunning area facing the ocean and hop in the oceanfront pool a few steps away...

    1 Bedrooms, 1 Bathrooms, Sleeps 3

    HI>Kailua-Kona

    95 USD - 105 USD

    nightly

    625 USD - 695 USD

    weekly

    2,200 USD - 2,400 USD

    monthly

  • NEW OWNER DISCOUNT - Beautiful, Ocean Views, Excellent Location. Book it!

    E Komo Mai.....Welcome! A beautiful, well maintained home in paradise is waiting for you. The interior is beautiful, the kitchen is well equipped, and has all the conveniences for your enjoyment. But most of the time you will find yourself on the...

    1 Bedrooms, 1 Bathrooms, Sleeps 4

    HI>Kailua-Kona

    95 USD - 299 USD

    nightly

    600 USD - 1,800 USD

    weekly

    2,550 USD - 2,800 USD

    monthly

  • Amazing ocean views,newly renovated,quick walk to town, close to beaches

    Your home away from home-everything you need is here, just come and enjoy. Newly renovated, fully equipped apartment on the second floor(easy access) in friendly complex close to town (10-15 minute walk), only 7 miles from airport Sleeps 2-4 real...

    1 Bedrooms, 1 Bathrooms, Sleeps 4

    HI>Kailua-Kona

    95 USD - 135 USD

    nightly

    625 USD - 945 USD

    weekly

    2,100 USD - 2,600 USD

    monthly

  • Red Ginger Garden Studio

    Peaceful private well appointed room with private entrance overlooking garden of fruit trees and red ginger blooms. Private bath with shower,queen bed ,walk in closet, kitchenette,outdoor seating yourself lounging under the mango tree swinging in...

    1 Bedrooms, 1 Bathrooms, Sleeps 2

    HI>Kailua-Kona

    95 USD - 143 USD

    nightly

    1,000 USD - 1,000 USD

    weekly

  • White Sands Village - Beautiful Ocean View - 2Bed/2Bath

    White Sands Village is directly across from the best boogie boarding beach on the island, also called "Magic Sands Beach". Begin your mornings sipping Kona coffee on the large lanai while looking at the boats on the beautiful ocean overlooking go...

    2 Bedrooms, 2 Bathrooms, Sleeps 4

    HI>Kailua Kona

    98 USD - 145 USD

    nightly

    950 USD - 950 USD

    weekly

    3,500 USD - 3,500 USD

    monthly

  • Luxury Condo, Downtown Kailua Kona, Great 5th floor, Ocean Views & Breezes

    Welcome to our home in Kailua Vilage Condos, located in the heart of Kailua Kona. Our condo is on the 5th floor with wonderful views, ocean and mountain breezes, and fantastic sunsets. The condo complex has keyed elevators and stairwells for your ...

    1 Bedrooms, 1 Bathrooms, Sleeps 4

    HI>Kailua Kona

    99 USD - 175 USD

    nightly

    640 USD - 640 USD

    weekly

    2,470 USD - 3,550 USD

    monthly

  • Aloha Romantic Hawaiian Beach Condo Lovely, Clean & Comfy Downtown Kona

    Perfect location! Lush tropical grounds!. Lovely, clean and comfy upgraded seaside studio. A fabulous setting with Olde Hawaii plantation-style architecture and Tiki torches creates a romantic ambiance straight out of a classic Hawaiian adventure ...

    0 Bedrooms, 1 Bathrooms, Sleeps 4

    HI>Kailua-Kona

    99 USD - 199 USD

    nightly

    660 USD - 1,393 USD

    weekly

    2,390 USD - 2,460 USD

    monthly

  • Tropical Paradise Home W Heated Pool, Spa, Waterfall, And Gardens (1B)

    Homes Over Kona: Property Description Enjoy resort living on hillside slopes at a perfect elevation. Aromatic tropical breezes, spring-like temperatures, and birds singing in this sub-climate are to be sure to tickle your senses. Not too hot, ...

    2 Bedrooms, 1 Bathrooms, Sleeps 6

    HI>Holualoa

    99 USD - 254 USD

    nightly

    494 USD - 1,769 USD

    weekly

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