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
    1BR w/ Pools, Steps to Kamaole Beach 3

    1BR w/ Pools, Steps to Kamaole Beach 3

    Kihei, HI

    Pool
    FREE CANCELLATION

    $114 to $414/night

  2. CONDOMINIUM
    2BR Beachfront Condo w/ Ocean View

    2BR Beachfront Condo w/ Ocean View

    Kihei, HI

    Pool
    FREE CANCELLATION

    $320 to $799/night

  3. CONDOMINIUM
    2BR/2BA at Kahalu’u Beach w/ Pool, Spa, Ocean View

    2BR/2BA at Kahalu’u Beach w/ Pool, Spa, Ocean View

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $174 to $445/night

  4. TOWNHOUSE
    3BR Pacific Paradise w/ Pool- 5 Minutes to Beach

    3BR Pacific Paradise w/ Pool- 5 Minutes to Beach

    Kamuela, HI

    Pool Hot Tub
    FREE CANCELLATION

    $175 to $632/night

  5. CONDOMINIUM
    3BR w/ Infinity Pool & Spa, Near Snorkeling Beach

    3BR w/ Infinity Pool & Spa, Near Snorkeling Beach

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $177 to $424/night

  6. CONDOMINIUM
    Aina Nalu 1BR w/ On-Site Pools, Spa & Cabanas

    Aina Nalu 1BR w/ On-Site Pools, Spa & Cabanas

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $157 to $489/night

  7. HOUSE
    Ainamalu 29 at Waikoloa Beach Resort

    Ainamalu 29 at Waikoloa Beach Resort

    Waikoloa, HI

    FREE CANCELLATION

    $481 to $896/night

  8. CONDOMINIUM
    Big Island Paradise

    Big Island Paradise

    Waikoloa, HI

    Pool Hot Tub

    $330 to $689/night

  9. CONDOMINIUM
    Colony Villas at Waikoloa Beach Resort #2204

    Colony Villas at Waikoloa Beach Resort #2204

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $234 to $464/night

  10. CONDOMINIUM
    Exceptional Value for Family! Beautiful Views, Sunsets & Minutes from the Beach!

    Exceptional Value for Family! Beautiful Views, Sunsets &...

    Waikoloa Village, HI

    Pool Hot Tub
    FREE CANCELLATION

    $152 to $286/night

  11. CONDOMINIUM
    Fairway Villas Waikoloa A21

    Fairway Villas Waikoloa A21

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $234 to $407/night

  12. VILLA
    Fairway Villas Waikoloa N21

    Fairway Villas Waikoloa N21

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $234 to $407/night

  13. CONDOMINIUM
    Hale Malu Ko Olina Beach Villa (O221)

    Hale Malu Ko Olina Beach Villa (O221)

    Kapolei, HI

    Pool Hot Tub

    $362 to $1,204/night

  14. CONDOMINIUM
    Hale Maluhia Ko Olina Beach Villa (O425)

    Hale Maluhia Ko Olina Beach Villa (O425)

    Kapolei, HI

    Pool Hot Tub

    $362 to $1,204/night

  15. HOUSE
    Hawaii Kai 4BR w/ Wraparound Lanai & Ocean Views

    Hawaii Kai 4BR w/ Wraparound Lanai & Ocean Views

    Honolulu, HI

    FREE CANCELLATION

    $606 to $883/night

  16. CONDOMINIUM
    Kahana Villa 2BR w/ Ocean-View Lanai, Pool & Spa

    Kahana Villa 2BR w/ Ocean-View Lanai, Pool & Spa

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $159 to $503/night

  17. CONDOMINIUM
    Kapalua Bay Villa 29B2 Ocean Front

    Kapalua Bay Villa 29B2 Ocean Front

    Lahaina, HI

    Pool

    $563 to $1,031/night

  18. TOWNHOUSE
    Ko Olina Kai Condo (1085E)

    Ko Olina Kai Condo (1085E)

    Kapolei, HI

    Pool Hot Tub
  19. CONDOMINIUM
    Kolepa Aloha

    Kolepa Aloha

    Waikoloa, HI

    Pool Hot Tub

    $162 to $401/night

  20. CONDOMINIUM
    Luxe 2BR/2BA- Infinity Pool & Spa- 1 Mile to Bay

    Luxe 2BR/2BA- Infinity Pool & Spa- 1 Mile to Bay

    Waikoloa Beach Resort, HI

    Pool Hot Tub
    FREE CANCELLATION

    $137 to $260/night

  21. CONDOMINIUM
    Luxe 3BR w/ Pool & 2 Private Lanais, Walk to Beach

    Luxe 3BR w/ Pool & 2 Private Lanais, Walk to Beach

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $190 to $633/night

  22. CONDOMINIUM
    Maui Kamaole 2BR w/ Lanais & 2 Pools

    Maui Kamaole 2BR w/ Lanais & 2 Pools

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $197 to $540/night

  23. CONDOMINIUM
    Mauna Lani Terrace D201

    Mauna Lani Terrace D201

    Kamuela, HI

    Pool Hot Tub
    FREE CANCELLATION

    $688 to $759/night

  24. HOUSE
    New Listing! 2-Acre Retreat w/ Pool, Ocean Views

    New Listing! 2-Acre Retreat w/ Pool, Ocean Views

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $219 to $600/night

  25. CONDOMINIUM
    New Listing! Ocean-View Apartment w/ Pool & Spa

    New Listing! Ocean-View Apartment w/ Pool & Spa

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $128 to $343/night

  26. CONDOMINIUM
    Noelani #110

    Noelani #110

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $296 to $521/night

  27. CONDOMINIUM
    Noelani #219

    Noelani #219

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $173 to $381/night

  28. CONDOMINIUM
    Nohonani #105

    Nohonani #105

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $274 to $381/night

  29. CONDOMINIUM
    Nohonani #300

    Nohonani #300

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $274 to $521/night

  30. CONDOMINIUM
    Ocean View w/Pool- Across from Kalama Beach

    Ocean View w/Pool- Across from Kalama Beach

    Kihei, HI

    Pool
    FREE CANCELLATION

    $146 to $378/night

  31. CONDOMINIUM
    Oceanfront 1BR w/ Lanai & Pool

    Oceanfront 1BR w/ Lanai & Pool

    Kihei, HI

    Pool
    FREE CANCELLATION

    $138 to $316/night

  32. CONDOMINIUM
    Pikake A-4

    Pikake A-4

    Lahaina, HI

    FREE CANCELLATION

    $195 to $381/night

  33. CONDOMINIUM
    Sea Village 1-203

    Sea Village 1-203

    Kailua-Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $164 to $231/night

  34. CONDOMINIUM
    Shores at Waikoloa #234 at Bo Tree Tower

    Shores at Waikoloa #234 at Bo Tree Tower

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $221 to $464/night

  35. CONDOMINIUM
    The Mauna Lani Golf Villas B5

    The Mauna Lani Golf Villas B5

    Kamuela, HI

    Pool Hot Tub
    FREE CANCELLATION

    $370 to $741/night

  36. HOUSE
    Tranquil 4BR Home by Private Beach

    Tranquil 4BR Home by Private Beach

    Kahuku, HI

    FREE CANCELLATION

    $344 to $479/night

  37. CONDOMINIUM
    Unobstructed Oceanfront! 2BR + Loft w/ Lanai, Pool

    Unobstructed Oceanfront! 2BR + Loft w/ Lanai, Pool

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $174 to $444/night

  38. VILLA
    Vacation Home in Ko Olina Resort

    Vacation Home in Ko Olina Resort

    Kapolei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $146 to $158/night

  39. CONDOMINIUM
    Villages At Mauna Lani #621

    Villages At Mauna Lani #621

    Kamuela, HI

    Pool Hot Tub
    FREE CANCELLATION

    $370 to $901/night

  40. CONDOMINIUM
    Vista Waikoloa D-102

    Vista Waikoloa D-102

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $234 to $464/night

  41. CONDOMINIUM
    Waikoloa Beach Villas B2

    Waikoloa Beach Villas B2

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $221 to $431/night

  42. VILLA
    Waikoloa Beach Villas C3

    Waikoloa Beach Villas C3

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $197 to $431/night

  43. VILLA
    Waikoloa Beach Villas I1

    Waikoloa Beach Villas I1

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $333 to $741/night

  44. CONDOMINIUM
    Waipuilani Park 2BR w/ Pool- Walk to Beach, Shops

    Waipuilani Park 2BR w/ Pool- Walk to Beach, Shops

    Kihei, HI

    Pool
    FREE CANCELLATION

    $134 to $490/night