Welcome to Hawaii! Paradise on earth! RedAwning has the perfect vacation rental for your island adventures. Beach bungalows, resort condos, and sun-kissed ocean-front villas await. Browse your island destination using the blue location links below or filter your preferences using the panel to the side. RedAwning offers easy, instant, hotel-style reservations and a simplified booking process so you can have your vacation plans covered in no time.

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  1. HOUSE
    Hale Ke Aluala

    Hale Ke Aluala

    Waimea, HI

    This large 2 bedroom/ 2 bath home has enormous square footage, vaulted bamboo ceilings and a huge wrap around deck. New furnishings, top of the line appliances, gourmet kitchen and so much more… Newly installed A/C and many ceiling fans make it a...

    FREE CANCELLATION

    $471 to $683/night

  2. TOWNHOUSE
    Ko Olina Kai Condo (1085E)

    Ko Olina Kai Condo (1085E)

    Kapolei, HI

    Book with confidence! This vacation rental is a LEGAL Oahu vacation rental operating in a Resort Zoned District and is not affected by the passage of Bill 89. LIVE CALENDAR: If the calendar shows as available, the property IS available and can be...

    Pool Hot Tub

    $218/night

  3. CONDOMINIUM
    SkyTower 2602 Condominium

    SkyTower 2602 Condominium

    Honolulu, HI

    High Quality Condo Sleeps 4 plus w/Salt Water Pool & Sauna  ++ Hot New Listing April 2018 ++ Superb High quality 1 bedroom Suite that sleeps 4 guests on High Floor with Great Views. Full Kitchen and Washer Dryer in the Condo. High Speed WiFi and...

    FREE CANCELLATION

    $156 to $201/night

  4. CONDOMINIUM
    Hale Mahina B401

    Hale Mahina B401

    Lahaina, HI

    Enjoy your Maui vacation from the Hale Mahina Resort! This gorgeous 2 bedroom, 2 bath, lush ocean view condo is the perfect place for couples or families looking to experience and explore the island. Equipped with a full kitchen with stainless...

    Pool Hot Tub
    FREE CANCELLATION

    $331 to $686/night

  5. CONDOMINIUM
    Paki Maui 415

    Paki Maui 415

    Lahaina, HI

    Come enjoy the Paki Maui Oceanfront Resort! This 1 bedroom, 1 bath, lush garden view condo is the perfect place for couples, small families and adventurers looking to experience and explore the island for all the wondrous places and memories it...

    Pool Hot Tub
    FREE CANCELLATION

    $136 to $174/night

  6. CONDOMINIUM
    One Block to Waikiki Beach

    One Block to Waikiki Beach

    Waikiki, HI

    2 bedroom, 2 bath luxury condo located in the heart of Waikiki Beach. Only 1 block to the ocean. The unit has a King in the master, 2 Fulls in the guest bedroom and a Queen sleeper in the living room. The kitchen is fully equipped with all...

    Hot Tub
    FREE CANCELLATION

    $366 to $563/night

  7. VILLA
    Vacation Home in Ko Olina Resort

    Vacation Home in Ko Olina Resort

    Kapolei, HI

    Ko Olina Kai is a peaceful gated community that offers all the tranquil privacy you could desire! The interior is spacious and homey with 2 bedrooms, 2 baths, a living room with an adjacent dining space, and a kitchen. This outstanding villa offers...

    Pool Hot Tub
    FREE CANCELLATION

    $152 to $158/night

  8. CONDOMINIUM
    Sands Of Kahana 336

    Sands Of Kahana 336

    Lahaina, HI

    Whether you're snorkeling with the sea turtles, Humpback whale watching in the winter, surfing, SUP’ing or just kicking back on the lanai to enjoy a rainbow, it doesn't get any better than this property. The Sands of Kahana sits on the pristine...

    Pool Hot Tub

    $332 to $388/night

  9. CONDOMINIUM
    Honua Kai Konea 215

    Honua Kai Konea 215

    Lahaina, HI

    HONUA KAI RESORT AND SPA SUITE 215 welcomes you with so much This spacious studio, 1 bath can accommodate up to 4 guests. Included in our fabulous price are many owner-supplied extras such as: • Beach chairs (2) • Beach umbrella • Beach...

    Pool Hot Tub
    FREE CANCELLATION

    $275 to $413/night

  10. COTTAGE
    Mauna Lani KaMilo Home (424)

    Mauna Lani KaMilo Home (424)

    Kamuela, HI

    This spectacular 3 bedroom- 3 bath single-level cottage is located within Kamilo, which is nestled near the heart of the Mauna Lani Resort area. Upon entering Mauna Lani KaMilo Home (424) enjoy the vaulted ceilings and open floor plan which allows...

    Pool Hot Tub

    $481 to $1,286/night

  11. CONDOMINIUM
    Mauna Lani Golf Villas C1

    Mauna Lani Golf Villas C1

    Kamuela, HI

    Our 2-story villa is the best unit in the Golf Villas! C1 is situated in a superior end villa location on the 10th fairway of the famed championship Francis H. I'I Brown South Course at Mauna Lani. The course was the former home to the annual Senior...

    Pool

    $418 to $720/night

  12. CONDOMINIUM
    Hanalei Bay Resort 8133/4

    Hanalei Bay Resort 8133/4

    Princeville, HI

    This bay view 2br/2ba (Hanalei Bay Resort 8133/4) includes one king bed in the first bedroom and two double beds in the second bedroom. Sleeps 6. Air conditioning (in living room and guest bedroom)! Included are two full baths, full kitchen,...

    Pool Hot Tub
    FREE CANCELLATION

    $253 to $904/night

  13. CONDOMINIUM
    Hale Pineapple

    Hale Pineapple

    Lahaina, HI

    Welcome to Hau'oli Hala Kahiki, a hidden gem in Honokowai on Maui's beautiful west shore. Located in the quiet, low-density Kaleialoha building, this sweet 1 bedroom/1 bath condo sits on the ground floor, so no stairs to climb or having to wait for...

    FREE CANCELLATION

    $180 to $239/night

  14. ESTATE
    Mauna Kea Resort Bluffs 22- The Beach House

    Mauna Kea Resort Bluffs 22- The Beach House

    Kamuela, HI

    This 8,000-square foot luxury estate with 2,750 square feet of outdoor living space is situated on a private, secure cul-de-sac in the Bluffs area of the Kohala Coast. The Beach House at the Bluffs features an award-winning green design, original...

    Pool Hot Tub

    $3,695 to $6,075/night

  15. VILLA
    Kapalua Ridge Villa 114 Gold Ocean View

    Kapalua Ridge Villa 114 Gold Ocean View

    Kapalua, HI

    This enchanting ridge villa, is newly remodeled to include all the high end upgrades you would expect to find in a 5 star resort. It has an attached covered carport for 2 cars, a lovely garden off the master suite and beautiful ocean views. Just a...

    Pool

    $294 to $494/night

  16. CONDOMINIUM
    Keauhou Kona Surf & Racquet Club #6-104

    Keauhou Kona Surf & Racquet Club #6-104

    Kailua Kona, HI

    **BRAND NEW PROPERTY IN OUR INVENTORY! AIR CONDITIONING INSTALLED AS OF SEPTEMBER 2018!** Unit#6-104 is a well-maintained 2BR/2BA ground floor unit in a 15-acre, gated oceanfront complex at the Keauhou Kona Surf & Racquet Club. It's also an end...

    Pool
    FREE CANCELLATION

    $256 to $292/night

  17. CONDOMINIUM
    Casa De Emdeko 111

    Casa De Emdeko 111

    Kailua Kona, HI

    Casa#111 is an excellent ground floor unit, that's VERY spacious! Nearly 1300 square feet! Close to the pool for easy access. There are new owners who own the property! Wifi! Casa De Emdeko offers owners and guests the perfect blend of Hawaiian...

    Pool
    FREE CANCELLATION

    $309 to $323/night

  18. CONDOMINIUM
    Kona Plaza#220

    Kona Plaza#220

    Kailua Kona, HI

    Welcome to the listing page of Kona Plaza#220! It's amazing location puts you right in immediate walking distance to restaurants, beaches, shopping & entertainment right in the heart of Kailua Village. This comfortable 1 bedroom, 1 bath that sleeps...

    Pool
    FREE CANCELLATION

    $139 to $211/night

  19. CONDOMINIUM
    Casa De Emdeko 204

    Casa De Emdeko 204

    Kailua Kona, HI

    Casa 204 is an excellent, affordable 2nd floor property that you will certainly love. Unit#204 has been NEWLY REMODELED IN APRIL 2019! All new flooring, furniture, kitchen, bathrooms, paint, appliances! Central AC, WIFI, Elevators, Beach gear! Look...

    Pool
    FREE CANCELLATION

    $165 to $239/night

  20. CONDOMINIUM
    Cliffs 4206

    Cliffs 4206

    Princeville, HI

    The Cliffs with an Ocean View! Enjoy the wonderful ocean views from this 1 bedroom 2 bath condo. This condo offers great cross ventilation to keep your stay more comfortable. You may dine out on the lanai and take in the cool ocean breezes. The...

    Pool Hot Tub

    $241 to $301/night

  21. CONDOMINIUM
    Cliffs 1206

    Cliffs 1206

    Princeville, HI

    If you are coming to Kauai to view the ocean from afar in the comfort of your vacation rental then this condo is not for you. But if you are coming to Kauai to be in the ocean and explore the many wonders of the Garden Isle during the day, then this...

    Pool Hot Tub

    $211 to $259/night

  22. CONDOMINIUM
    Cliffs 8205

    Cliffs 8205

    Princeville, HI

    Building 8 will have some renovations taking place from 9/29/2017 - 12/24/2017 Located in Princeville on the lush north shore of Kauai, Cliffs 8205 is the perfect home away from home (up to 4). This luxury condo has spectacular unobstructed ocean...

    Pool Hot Tub

    $253 to $301/night

  23. CONDOMINIUM
    Cliffs 4205

    Cliffs 4205

    Princeville, HI

    This beautiful Kauai vacation rental is equipped with all of the modern luxury you’ll need, while also providing an easy, tranquil vacation-getaway on Kauai's paradisical north shore in Princeville. Stare into the expanse of the deep blue Pacific...

    Pool Hot Tub

    $235 to $301/night

  24. CONDOMINIUM
    Maui Ka'anapali Villas Studio Premier Condo A417

    Maui Ka'anapali Villas Studio Premier Condo A417

    Lahaina, HI

    We invite you to come and stay in our upgraded condo just steps from famous Ka'anapali Beach! Relax and enjoy this Premier Studio Maui Ka'anapali Villas condo in Lahaina, Maui. 544 sq. ft. of island living for up to 4 adults (King Murphy bed, queen...

    Pool
    FREE CANCELLATION

    $336 to $636/night

  25. CONDOMINIUM
    Kamaole Sands #7-403

    Kamaole Sands #7-403

    Kihei, HI

    Kamaole Sands Unit 7-403, a spacious fourth floor (top level), 2 bedroom, 2 bath unit with a partial ocean view. Located across the street from Kamaole Beach III, this unit is great for fun-filled days and quiet evenings. All the amenities from home...

    Pool Hot Tub
    FREE CANCELLATION

    $219 to $429/night

  26. CONDOMINIUM
    Kona Makai 6301

    Kona Makai 6301

    Kailua Kona, HI

    One of the best ocean front locations along the Kona Coast; top level corner unit with panoramic ocean views. These oceanfront units are the most prized units in the complex. Completely remodeled 2 bedroom, 2 bath condo with an amazing wrap around...

    Pool

    $286 to $409/night

  27. HOUSE
    O'oma Plantation

    O'oma Plantation

    Kailua Kona, HI

    Why book individual resorts or condos when your whole group can enjoy a mansion in paradise? Enjoy exceptional panoramic coastal views from the private and quiet custom home at the O’oma Plantation. This large home is the perfect escape for a...

    Pool Hot Tub

    $1,179 to $1,664/night

  28. CONDOMINIUM
    Honua Kai 520

    Honua Kai 520

    Lahaina, HI

    What sounds better than waking up to a hot cup of delicious coffee on a lanai that opens up to sweeping views of the majestic West Maui mountains? We invite you to indulge in the authentic Maui lifestyle, making our Honua Kai 520K your home away...

    Pool Hot Tub
    FREE CANCELLATION

    $427 to $1,075/night

  29. CONDOMINIUM
    Maui Kamaole #G-210

    Maui Kamaole #G-210

    Kihei, HI

    The famous Kamaole Beach III is just across the street from the upscale Maui Kamaole. This property features lush tropical landscaping, two gorgeous pool areas with hot tubs and water features. There are gas grills peppered throughout the property...

    Pool Hot Tub
    FREE CANCELLATION

    $377 to $493/night

  30. HOUSE
    Alii Point #15- Almost Oceanfront

    Alii Point #15- Almost Oceanfront

    Kailua Kona, HI

    Almost Oceanfront. Spend your vacation in a luxurious single family home within a private, gated, enclave of 16 seaside homes. This Alii Point subdivision of fine, luxury residences is a tropical paradise surrounded by a botanical garden with beach...

    Pool
    FREE CANCELLATION

    $608 to $791/night