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
    Ka Hale Kaeloha (House of Love) – Romantic Oceanside Condo

    Ka Hale Kaeloha (House of Love) – Romantic Oceanside C...

    Kaunakakai, HI

    The enchanting views and multiple attractions at Molokai Shores await you at this lovingly furnished, one-bedroom condo. With all new, tropical furniture and decor, this home provides a full-blown, Hawaiian experience plus everything you need to...

    Pool Pets OK
    FREE CANCELLATION

    $158 to $191/night

  2. HOUSE
    Junior Suite Oceanfront #303

    Junior Suite Oceanfront #303

    Lahaina, HI

    Jr. Suite - Bright and Easy Island Style. Queen bed (no sofa bed), tiled entryway, Flat Screen TV, light furnishings throughout. Put away your groceries and make yourself at home. Enjoy your private lanai with your favorite beverage. Watch the...

    Pool Hot Tub
    FREE CANCELLATION

    $278 to $341/night

  3. HOUSE
    Junior Suite Oceanfront #706

    Junior Suite Oceanfront #706

    Kaanapali, HI

    Our Junior Suite is spacious and well-appointed with a Queen Bed; as well as a sofa bed for the occasional guest. There are seating arrangements for relaxing and dining. You will find plenty of space to store your clothing and personal items. The...

    Pool Hot Tub
    FREE CANCELLATION

    $278 to $341/night

  4. CONDOMINIUM
    Hale Alii Ko Olina Beach Villa (O924)

    Hale Alii Ko Olina Beach Villa (O924)

    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

    $397 to $1,204/night

  5. CONDOMINIUM
    Waiohuli Beach Hale #C-211

    Waiohuli Beach Hale #C-211

    Kihei, HI

    Waiohuli Beach Hale is a small oceanfront complex located in Kihei Maui Hawaii. This property has a great aloha feeling with a relaxed and quiet atmosphere. Each unit is steps from the ocean and is centrally located to great shopping, restaurants,...

    Pool
    FREE CANCELLATION

    $208 to $347/night

  6. CONDOMINIUM
    G5-1 Bedroom Oceanfront

    G5-1 Bedroom Oceanfront

    Kihei, HI

    Ma'alaea Surf, Unit G5 - Just steps from one of Maui’s longest white sand beaches, recently renovated G-5 has all the amenities of a luxury resort. Centrally located between the tourists centers of Lahaina/Kapalua and Wailea/Makena, Maalaea Surf...

    Pool
    FREE CANCELLATION

    $259 to $428/night

  7. CONDOMINIUM
    Waiohuli Beach Hale #D-220

    Waiohuli Beach Hale #D-220

    Kihei, HI

    Waiohuli Beach Hale is a small oceanfront complex located in Kihei Maui Hawaii. This property has a great aloha feeling with a relaxed and quiet atmosphere. Each unit is steps from the ocean and is centrally located to great shopping, restaurants,...

    Pool
    FREE CANCELLATION

    $157 to $277/night

  8. CONDOMINIUM
    Hale Moana Ko Olina Beach Villa (B305)

    Hale Moana Ko Olina Beach Villa (B305)

    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

    $397 to $1,268/night

  9. CONDOMINIUM
    Hale Lanikai Ko Olina Beach Villa (O1104)

    Hale Lanikai Ko Olina Beach Villa (O1104)

    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 CALENDARIf the calendar shows as available, the property is not reserved and can be...

    Pool Hot Tub

    $408 to $1,384/night

  10. CONDOMINIUM
    A1-2 Bedroom Beachfront

    A1-2 Bedroom Beachfront

    Kihei, HI

    Maalaea Surf, Unit A1 is a conveniently located ground floor unit, direct beachfront, just steps away from the beach. This unit features an updated kitchen with convection oven, dishwasher and large refrigerator. The master bedroom has twin beds....

    Pool
    FREE CANCELLATION

    $416 to $664/night

  11. CONDOMINIUM
    Hale Nani Ikena Kai Ko Olina Beach Villa (B109)

    Hale Nani Ikena Kai Ko Olina Beach Villa (B109)

    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

    $548 to $2,016/night

  12. CONDOMINIUM
    Hale Papakea Ko Olina Beach Villa (B110)

    Hale Papakea Ko Olina Beach Villa (B110)

    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

    $548 to $2,016/night

  13. CONDOMINIUM
    D4-1 Bedroom Beachfront

    D4-1 Bedroom Beachfront

    Kihei, HI

    Ma'alaea Surf, Unit D4 - Deluxe in every sense. D4 is an ideally located ground floor unit, approximately 5 steps from the white sandy beach. This luxurious unit features a contemporary kitchen. Enjoy the ocean views and Maui's majestic sunset from...

    Pool
    FREE CANCELLATION

    $304 to $467/night

  14. HOUSE
    Junior Suite Oceanfront #707

    Junior Suite Oceanfront #707

    Kaanapali, HI

    Our 7th floor Junior Suite is spacious and well-appointed with a Queen Bed; as well as a queen sofa sleeper for the occasional guest. There are seating arrangements for relaxing and dining. You will find plenty of space to store your clothing and...

    Pool Hot Tub
    FREE CANCELLATION

    $258 to $309/night

  15. CONDOMINIUM
    B2-1 Bedroom Oceanfront

    B2-1 Bedroom Oceanfront

    Kihei, HI

    Maalaea Surf, Unit B2, is a conveniently located ground floor unit, just steps away from the pool and ocean. This luxurious unit features a fully furnished kitchen, large master suite with king size bed and a queen size sofa bed in the living room....

    Pool
    FREE CANCELLATION

    $259 to $428/night

  16. HOUSE
    Junior Suite Oceanfront #702

    Junior Suite Oceanfront #702

    Lahaina, HI

    This Studio Unit offers a Magnificent ocean view; with the Islands of Lanai and Molokai off in the distance. The living area features a Queen sized bed in a tranquil earth-tone setting. The Sofa has a hidden pull-out bed for the occasional guest....

    Pool Hot Tub
    FREE CANCELLATION

    $278 to $341/night

  17. CONDOMINIUM
    Hale Ili Ili #A

    Hale Ili Ili #A

    Kihei, HI

    Hale Ili Ili is an oceanfront gated 4 plex.This property is steps from Kamaole Beach #1 and Charley Young's Cove. Panoramic ocean views and magnificent sunsets can be seen daily from this property. This property has an oceanfront pool, hot tub and...

    Pool Hot Tub
    FREE CANCELLATION

    $695 to $1,043/night

  18. CONDOMINIUM
    Keauhou Kona Surf and Racquet Club 2-204

    Keauhou Kona Surf and Racquet Club 2-204

    Kailua Kona, HI

    Welcome to the page of our gorgeous Keauhou Kona Surf & Racquet Club#2-204! DIRECT OCEANFRONT CORNER units are extra special here. The lanai is extended for extra space. 2nd floor, so only 1 flight of stairs! This property is absolutely spectacular....

    Pool
    FREE CANCELLATION

    $311 to $350/night

  19. CONDOMINIUM
    Hale Ikena Ko Olina Beach Villa (O1406)

    Hale Ikena Ko Olina Beach Villa (O1406)

    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

    $432 to $1,384/night

  20. CONDOMINIUM
    Kaleialoha #215

    Kaleialoha #215

    Lahaina, HI

    Nice corner unit offers privacy and expanded views. Cal King bed, New carpet and appliances. AC, washer/dryer, free wireless internet, local phone and basic cable.Flat screen TV. All basic amenities included including linens, beach supplies and...

    Pool
    FREE CANCELLATION

    $183 to $384/night

  21. CONDOMINIUM
    D1-2 Bedroom Beachfront

    D1-2 Bedroom Beachfront

    Kihei, HI

    Ma'alaea Surf, Unit D1 is a conveniently located ground floor unit, direct beachfront, just steps away from the beach. This unit features a full kitchen and dining table. The master bedroom has a king size bed. The guest room also features a king...

    Pool
    FREE CANCELLATION

    $416 to $664/night

  22. CONDOMINIUM
    Noelani #219

    Noelani #219

    Lahaina, HI

    One way to enhance an ocean view is to wrap it in lush lawns and gardens. Add to that not one, but two oceanfront pools and a Jacuzzi, and what more can you ask for? How about being as close to the ocean as you can possibly get without being on a...

    Pool Hot Tub
    FREE CANCELLATION

    $173 to $251/night

  23. CONDOMINIUM
    Waiohuli Beach Hale #D-223

    Waiohuli Beach Hale #D-223

    Kihei, HI

    Waiohuli Beach Hale is a small oceanfront complex located in Kihei Maui Hawaii. This property has a great aloha feeling with a relaxed and quiet atmosphere. Each unit is steps from the ocean and is centrally located to great shopping, restaurants,...

    Pool
    FREE CANCELLATION

    $218 to $440/night

  24. CONDOMINIUM
    Waiohuli Beach Hale #D-225

    Waiohuli Beach Hale #D-225

    Kihei, HI

    Waiohuli Beach Hale #D-225 is a completely remodeled second floor oceanfront, ocean view 1 bedroom, 1 bath condo. It is just steps from the ocean. It has a full kitchen, window unit air conditioning in the bedroom only, 2 flat screen TVs, DVD, high...

    Pool
    FREE CANCELLATION

    $232 to $465/night

  25. CONDOMINIUM
    Kuleana 321

    Kuleana 321

    Lahaina, HI

    Beautifully landscaped grounds on the water. Hear the waves rolling in while you enjoy this upgraded unit with granite counter tops in the kitchen and bath and tile floors throughout. Cable TV in living room and bedroom.Master Bedroom has a king bed...

    Pool
    FREE CANCELLATION

    $158 to $611/night

  26. CONDOMINIUM
    Valley Isle 902

    Valley Isle 902

    Lahaina, HI

    The Valley Isle Resort offers amazing views of the pacific ocean. Sound of waves replace music and ocean breeze keeps the house cool. It is located 5-8 minutes away from Kaanapali, Napili and Kapalua beaches but secluded from the touristic sites.The...

    Pool
    FREE CANCELLATION

    $150 to $473/night

  27. CONDOMINIUM
    Mahana 501

    Mahana 501

    LAHAINA, HI

    This brand-new beautiful new 5th floor listing at the Mahana at Kaanapali boasts gorgeous views of both the tranquil blue Pacific Ocean AND the lush West Maui Mountains. This property is extremely close to the water, you can literally sit in the 5th...

    Pool Hot Tub
    FREE CANCELLATION

    $438 to $1,689/night

  28. CONDOMINIUM
    Kulakane 301

    Kulakane 301

    Lahaina, HI

    Incredible ocean views and sunset views from this west facing 2-story condo. Wrap around windows and lanai with one of the most expansive view on West Maui. Watch dolphins, sea turtles, and whales from the private lanai. Extra wide and spacious...

    Pool
    FREE CANCELLATION

    $284 to $708/night

  29. CONDOMINIUM
    Kaanapali Shores 515

    Kaanapali Shores 515

    Lahaina, HI

    Relax on our 5th floor lanai, overlooking the ocean, well-kept grounds and pool at Kaanapali Shores! Kaanapali Shores resort is located on the beach in North Kaanapali. Unit 515 lanai has views of the ocean, renovated garden pool and spa,...

    Pool Hot Tub
    FREE CANCELLATION

    $374 to $1,000/night

  30. CONDOMINIUM
    Kaanapali Shores 725

    Kaanapali Shores 725

    Lahaina, HI

    Wonderful ocean and garden views from this spacious 2 bedroom unit . The owners have completed a beautiful remodel featuring carpeting, kitchen and bath upgrades and new furniture. The full kitchen was recently re-done with new appliances, granite...

    Pool Hot Tub
    FREE CANCELLATION

    $290 to $898/night