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. CONDOMINIUM
    Diamond Head Beach Hotel 1401

    Diamond Head Beach Hotel 1401

    Honolulu, HI

    Oceanfront - Spacious 1 Bd Penthouse With Large Living Area And Full Kitchen. Rooftop Penthouse - Sitting above the Pacific Ocean and nestled under Hawaii's iconic Diamond Head crater. Beautifully furnished with a light and airy ocean theme, this...

    FREE CANCELLATION

    $360 to $557/night

  2. CONDOMINIUM
    Kahana Sunset E 11

    Kahana Sunset E 11

    Lahaina, HI

    The Kahana Sunset Welcomes you with This unique condo is a beachfront property on the world famous West Coast of Maui between Kaanapali and Kapalua. Included in our fabulous price are many owner-supplied extras such as: • Beach chairs (2) •...

    Pool
    FREE CANCELLATION

    $251 to $389/night

  3. APARTMENT
    Waikiki Grand 411 Studio

    Waikiki Grand 411 Studio

    Honolulu, HI

    A Sweet Freshly Remodeled & updated balcony Studio Suite next to Waikiki Beach Great View & Balcony. Recently remodeled, painted and upgraded as of November 2018 - park, zoo and ocean views from this comfortable studio with balcony - You’ll love...

    Pool
    FREE CANCELLATION

    $124 to $174/night

  4. CONDOMINIUM
    Sugar Beach Resort, #418

    Sugar Beach Resort, #418

    Kihei, HI

    Sugar Beach Resort is the Winner of Building of the Year and Manager of the Year Awards from the Institute of Real Estate Management (IREM®) Sugar Beach Resort is a tranquil beachfront condominium resort located in North Kihei offering sweeping...

    Pool

    $190 to $387/night

  5. CONDOMINIUM
    Pali Ke Kua 203

    Pali Ke Kua 203

    Princeville, HI

    This spacious two bedroom vacation rental is the perfect home away from home for traveling families and friends. Relax in Paradise at Pali Ke Kua 203. Enjoy magnificent views from your unit or lanai of the ocean or stroll down to Pali Ke Kua's...

    Pool Hot Tub

    $362 to $422/night

  6. CONDOMINIUM
    Koa Lagoon #505

    Koa Lagoon #505

    Kihei, HI

    The Koa Lagoon is an ocean front condominium complex in North Kihei with spectacular panoramic views of the Pacific ocean and Mauna Kahalawai, also known as the West Maui Mountains. Situated just 15 minutes from Kahului Airport on Sugar Beach, Koa...

    Pool
    FREE CANCELLATION

    $208 to $296/night

  7. CONDOMINIUM
    O-904 Ko Olina Beach Villa

    O-904 Ko Olina Beach Villa

    Kapolei, HI

    Experience the ultimate in oceanfront resort living in this beautiful and spacious vacation home located in the Beach Villas at Ko Olina! Overview: This 2 BR, 2 BA luxury villa on the 9th floor of the Ocean Tower is conveniently located just 20...

    Pool Hot Tub

    $485 to $1,204/night

  8. CONDOMINIUM
    Alii Kai 3103

    Alii Kai 3103

    Princeville, HI

    Alii Kai 3103 is perfect for a family with sleeping room for 6 in 3 comfortable queen beds. Great north shore beaches and activities just minutes away, and a view so amazing you'll be tempted to just stay in and relax! This comfortable Alii Kai...

    Pool
    FREE CANCELLATION

    $238 to $293/night

  9. CONDOMINIUM
     Hale Ono Loa #119

    Hale Ono Loa #119

    Lahaina, HI

    Beautifully updated ground floor unit. Private and unique! Enter through your own private entrance and enjoy the distinctive qualities of this exceptional condo! Large lanai with direct ocean views! A/C in both bedrooms. All stainless steel...

    Pool
    FREE CANCELLATION

    $277 to $502/night

  10. CONDOMINIUM
    Honua Kai Konea 743

    Honua Kai Konea 743

    Lahaina, HI

    This rarely-available top-floor penthouse condominium is the ultimate in luxury living.  Konea 743 boasts amazing ocean views of Maui and the surrounding islands. This spacious suite includes two bedroom, two full baths and a sofa-bed to...

    Pool Hot Tub
    FREE CANCELLATION

    $513 to $988/night

  11. CONDOMINIUM
    O-704 Hale Lau Wai Ko Olina Beach Villa

    O-704 Hale Lau Wai Ko Olina Beach Villa

    Kapolei, HI

    Enjoy direct ocean-facing views and beautiful garden and pool area views from this luxury Beach Villa at Ko'Olina. This well-appointed 1,171 square foot 2 bedroom 2 bathroom 7th floor Beach Villa has direct ocean views overlooking the lap pool and...

    Pool

    $485 to $1,204/night

  12. CONDOMINIUM
    B-708: Hale Leilani Ko Olina Beach Villa

    B-708: Hale Leilani Ko Olina Beach Villa

    Kapolei, HI

    This 2bd, 2ba luxury oceanfront villa sleeps 4-6 and is located steps away from the pristine and relaxing beaches, lagoons, pools and jacuzzis. Close to shops, dining, golf and a variety of outdoor activities. Why ko olina? If you haven't been to...

    Pool

    $508 to $1,384/night

  13. CONDOMINIUM
    Sealodge E4

    Sealodge E4

    Princeville, HI

    Sealodge is located on Kauai’s most spectacular coastline, overlooking the majestic Pacific ocean. This 1 bedroom 1 bath condo is incredibly affordable considering the amazing views it provides of the ocean and Kilauea lighthouse. Enjoy the...

    Pool

    $235 to $301/night

  14. CONDOMINIUM
    Kanai A Nalu 212

    Kanai A Nalu 212

    Maalaea, HI

    Kanai A Nalu #212 is registered as a Transient Accommodation. Owner Registration I.D. TA-097-282-8672-01 Right On The Beach And Only Steps To The Sand / New Kitchen Remodel! This 2 br/ba second floor condo beach retreat is located at the popular...

    Pool
    FREE CANCELLATION
  15. VILLA
    Bay Villa 34b2 Gold Ocean Front

    Bay Villa 34b2 Gold Ocean Front

    Kapalua, HI

    Stunning ocean views from every room! Recent upgrades include new furnishings inside and out, new carpet, fresh paint and accessories. The rugged shore below is home to a variety of tropical birds, exotic plants, fish, and giant sea turtles. During...

    Pool

    $781 to $1,219/night

  16. CONDOMINIUM
    760 South Kihei Condo Unit 407

    760 South Kihei Condo Unit 407

    Kihei, HI

    Enjoy sun-soaked beach days and relaxing balmy evenings at this fourth-floor 2BR/2BA Menehune Shores condo. Your rental offers a prime location on the right side of the building, overlooking the pool and ocean. Take a dip in the heated pool, or...

    Pool
    FREE CANCELLATION

    $224 to $554/night

  17. HOUSE
    1 Bedroom Corner Oceanfront #701

    1 Bedroom Corner Oceanfront #701

    Kaanapali, HI

    Our One Bedroom Corner unit is spacious and well-appointed with a King Bed in the bedroom and a Queen sofa bed in the living room. There is seating arrangements for relaxing and dining. You will find plenty of space to store your clothing and...

    Pool Hot Tub
    FREE CANCELLATION

    $372 to $444/night

  18. HOUSE
    Junior Suite Oceanfront #1006

    Junior Suite Oceanfront #1006

    Lahaina, HI

    {Jr. Suite (Studio) - King bed; Flat screen TV; extended lanai} MAUI KAI 1006 This oceanfront junior suite is a bright, airy unit decorated in light tones, pale off-white tile in the kitchen and bath, with carpet in the center living area of the...

    Pool Hot Tub
    FREE CANCELLATION

    $278 to $341/night

  19. CONDOMINIUM
    Sealodge J9 Condo

    Sealodge J9 Condo

    Princeville, HI

    Sealodge J9 gives you dramatic and uninterrupted oceanfront views, top floor privacy, and your own furnished oceanfront lanai. With a full kitchen, this charming sea view rental gives you the option to stay in and enjoy a romantic al fresco dinner...

    Pool
    FREE CANCELLATION

    $238 to $275/night

  20. CONDOMINIUM
    Kona Alii 201

    Kona Alii 201

    Kailua-Kona, HI

    Right in the middle of town in walking distance from the Kona Pier. Remodeled and AC included. The pictures say it all! The unit has a Queen size sofa sleeper so can sleep 4 people comfortably. Stroll down Alii Drive and you will find a variety...

    Pool

    $181 to $309/night

  21. VILLA
    Bay Villa 36B3 Gold Ocean Front

    Bay Villa 36B3 Gold Ocean Front

    Kapalua, HI

    This elegant and upscale villa occupies the top two floors and features rare West-facing views for magnificent sunsets! A whale watchers dream! This villa offers the best vantage of whales and their young who make the bay their playground during...

    Pool

    $563 to $781/night

  22. CONDOMINIUM
    Paki Maui 414

    Paki Maui 414

    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
    FREE CANCELLATION

    $124 to $274/night

  23. CONDOMINIUM
    Maui Sunset #A-509

    Maui Sunset #A-509

    Kihei, HI

    Maui Sunset – 1BR Oceanfront Condo with a Whale-Watching Lanai There’s a reason many of our lovely guests return year after year to our oceanfront Maui condo. Actually, there are lots of reasons. The condo community’s sparkling pool which is...

    Pool Hot Tub
    FREE CANCELLATION

    $173 to $231/night

  24. VILLA
    Kapalua Bay Villa 21B2

    Kapalua Bay Villa 21B2

    Kapalua, HI

    This gorgeous Beach Front Villa occupies the top two floors of building 21. It has two completely private master bedrooms with en-suite. Main floor master has a private lanai. Both master suites have spectacular ocean views. There are 3 bathrooms;...

    Pool

    $1,219 to $1,813/night

  25. CONDOMINIUM
    Sugar Beach Resort, #524

    Sugar Beach Resort, #524

    Kihei, HI

    A note from the owner: Tropical bliss welcomes you from the moment you walk through the door and past the gorgeous island artwork hanging on the wall. As you step into the main living area of the condo, prepare yourself to see one of the most...

    Pool

    $190 to $387/night

  26. CONDOMINIUM
    Makena Surf Resort, #G-101

    Makena Surf Resort, #G-101

    Makena, HI

    A note from the owner. Welcome to our Maui ohana. Our unit is special because of the extra space and privacy, including the cool, shady side lanai we call our grotto - the perfect place to curl up with a good book, and a lovely respite from the...

    Pool

    $775 to $1,094/night

  27. VILLA
    Bay Villa 22G2 Gold Ocean Front

    Bay Villa 22G2 Gold Ocean Front

    Kapalua, HI

    Perfectly situated above the waves in the most pristine and highly desired locations in Kapalua! This unique floor plan is the only ground-floor Kapalua Bay villas that can boast an additional 150+ square feet of living space facing the ocean!!...

    Pool

    $813 to $1,219/night

  28. VILLA
    Bay Villa 22G4 Gold Ocean Front

    Bay Villa 22G4 Gold Ocean Front

    Kapalua, HI

    Dreaming of Paradise? You'll pinch yourself when you walk into this gorgeous Bay Villa. It's everything you imagined and more, including discounts on tee times at the world-famous Plantation and Bay Courses. Start your vacation with a frosty...

    Pool

    $563 to $781/night

  29. VILLA
    Bay Villa 28B2 Gold Ocean Front

    Bay Villa 28B2 Gold Ocean Front

    Lahaina, HI

    E Komo Mai 'Welcome' to Aloha Vacation Villa’s newest WATERFRONT vacation property! Nestled in the luxurious Kapalua area in north Maui, the spacious interior of this 2 bed 3 bath tranquil retreat is the perfect blend of premium comfort and...

    Pool

    $594 to $1,063/night

  30. CONDOMINIUM
    Oceanfront 3BR w/ Private Beach & AC

    Oceanfront 3BR w/ Private Beach & AC

    Kihei, HI

    Feel Pacific breezes as you unwind on the lanai of your fourth-floor 3BR/2BA condo. This unit commands the most sought-after location in the building (front and center), closest to the ocean and furthest from the road. Take in stunning wide-open...

    Pool
    FREE CANCELLATION

    $471 to $794/night