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 Pahukoa

    Hale Pahukoa

    Kailua Kona, HI

    This vintage Hawaiian beach house is nestled in a private gated community of Kona Bay Estates. The simple seaside style will melt all of your cares away as you sip on your Mai Tai in the cool shade of the deep, covered lanai. Experience the feel of...

    Pool
    FREE CANCELLATION

    $525 to $555/night

  2. CONDOMINIUM
    Pali Ke Kua 115

    Pali Ke Kua 115

    Princeville, HI

    Feel at home in Paradise in this one bedroom condominium at Pali Ke Kua. Enjoy extraordinary views of the ocean or stroll down to Pali Ke Kua's secret beach via a private, paved path. This condo is perfect for a couple's retreat. Rates may vary –...

    Pool Hot Tub

    $259 to $301/night

  3. HOUSE
    Puu Poa 403

    Puu Poa 403

    Princeville, HI

    Welcome to Pu'u Poa 403....your penthouse in the sky overlooking the endless reaches of the deep blue Pacific Ocean! This wonderful top floor unit gives you a bird's eye view of the tropical world around you. From your open air lanai or glassed in...

    Pool

    $422 to $663/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
    Hale Ono Loa 106

    Hale Ono Loa 106

    Lahaina, HI

    Enjoy this West Maui Ocean Front Resort with lush grounds which includes a pool, lounge area, shuffleboard, picnic area, BBQ’s. Relax on a Lanai and enjoying sunset dinners and beautiful views of Lanai and Molokai in the distance. Maui is known...

    Pool
    FREE CANCELLATION

    $199 to $200/night

  6. 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

  7. VILLA
    Kapalua Bay Villa 22G4 Gold Ocean Front

    Kapalua 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

  8. VILLA
    Kapalua Bay Villa 21B2 Gold Beach Front

    Kapalua Bay Villa 21B2 Gold Beach Front

    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...

    Pool

    $1,219 to $1,813/night

  9. CONDOMINIUM
    Kaleialoha #207

    Kaleialoha #207

    Lahaina, HI

    Completely remodeled condo. Two 55' Flat Screen TV's, A/C, Bosch washer Dryer, wine cooler. Granite and marble throughout. King bed. Free internet/ basic cable, onsite parking and local phone. Near Shopping, Restaurants and all beach activities....

    Pool
    FREE CANCELLATION

    $230 to $384/night

  10. CONDOMINIUM
    Kaleialoha 112

    Kaleialoha 112

    Lahaina, HI

    Enjoy the white sand beach and beautiful tiled pool while you step out of your large ground floor lanai to a gorgeous lawn and lounge area right on the ocean. Five steps to SWIMMING, SNORKELING, SURFING on the PRIVATE white sand beach! See whales...

    Pool
    FREE CANCELLATION

    $167 to $285/night

  11. CONDOMINIUM
    Honua Kai Konea 743 2BD 2BA

    Honua Kai Konea 743 2BD 2BA

    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 accommodate...

    Pool Hot Tub
    FREE CANCELLATION

    $513 to $988/night

  12. CONDOMINIUM
    Hale Mahina Ko Olina Beach Villa (O904)

    Hale Mahina Ko Olina Beach Villa (O904)

    Kapolei, HI

    Book with confidence! This vacation rental is a LEGAL Oahu vacation rental operating in a Resort Zone 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

    $455 to $1,204/night

  13. CONDOMINIUM
    Hale Kaimana Ko Olina Beach Villa (B903)

    Hale Kaimana Ko Olina Beach Villa (B903)

    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

    $617 to $1,784/night

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

    Hale Maluhia Ko Olina Beach Villa (O425)

    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 not reserved and can...

    Pool Hot Tub

    $485 to $1,204/night

  15. CONDOMINIUM
    Hale Lau Wai Ko Olina Beach Villa (O704)

    Hale Lau Wai Ko Olina Beach Villa (O704)

    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 can be booked instantly...

    Pool Hot Tub

    $455 to $1,204/night

  16. CONDOMINIUM
    Hale Kai Ko Olina Beach Villa (B904)

    Hale Kai Ko Olina Beach Villa (B904)

    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

    $594 to $1,784/night

  17. CONDOMINIUM
    Hale Makai Ko Olina Beach Villa (O805)

    Hale Makai Ko Olina Beach Villa (O805)

    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

    $582 to $1,668/night

  18. CONDOMINIUM
    Hale Kahakai Ko Olina Beach Villa (O212)

    Hale Kahakai Ko Olina Beach Villa (O212)

    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 Villa is not reserved and can be...

    Pool Hot Tub

    $501 to $1,500/night

  19. HOUSE
    Kauhale Pilialoha

    Kauhale Pilialoha

    Kamuela, HI

    Indulge yourself in the ultimate island style luxury at the Big Island of Hawaii’s most exclusive retreat, Kauhale Pilialoha. Experience breathtaking sunsets, enjoy the natural beauty of Hawaii from the ultimate poolside lanai perched on the...

    Pool Hot Tub

    $17,975 to $27,561/night

  20. CONDOMINIUM
    Sugar Beach Resort PH 40

    Sugar Beach Resort PH 40

    Kihei, HI

    The Sugar Beach Resort is the perfect destination for your tropical Hawaiian getaway! This oceanfront complex is just a few steps away from Maui's longest continual white sand beach, perfect for long strolls on the beach or enjoying postcard...

    Pool Hot Tub
    FREE CANCELLATION

    $393 to $544/night

  21. CONDOMINIUM
    Nohonani 405

    Nohonani 405

    Lahaina, HI

    Nohonani 405 is a beautiful two bedroom one and a half bath unit on the fourth floor, with vaulted ceilings and a breathtaking ocean view. Ocean views can be seen from the kitchen, dining areas, living room and master bedroom. As with all the...

    Pool
    FREE CANCELLATION

    $274 to $403/night

  22. CONDOMINIUM
    Waiohuli Beach Hale #A-201

    Waiohuli Beach Hale #A-201

    Kihei, HI

    Gorgeous Remodeled Oceanfront Kihei Condo – 2BR You can’t do better than this! Not only does this beautifully renovated second-floor unit have an unobstructed ocean view but the quality of the complex and its location cannot be beat. The ocean...

    Pool
    FREE CANCELLATION

    $208 to $347/night

  23. CONDOMINIUM
    Hale Leilani Ko Olina Beach Villa (B708)

    Hale Leilani Ko Olina Beach Villa (B708)

    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

    $508 to $1,384/night

  24. CONDOMINIUM
    A5-1 Beachfront Loft Suite

    A5-1 Beachfront Loft Suite

    Kihei, HI

    Maalaea Surf, Unit A5 is a townhouse unit on the second floor which offers our guest total privacy and is located beach front on the property. This loft suite with 2 baths is very well furnished. Enjoy ocean front outdoor living on your spacious...

    FREE CANCELLATION

    $304 to $467/night

  25. CONDOMINIUM
    G9-2 Bedroom Oceanfront Townhouse

    G9-2 Bedroom Oceanfront Townhouse

    Kihei, HI

    Ma'alaea Surf, Unit G9 is a townhouse unit situated on the second floor which offers our guest total privacy. This unit has stunning ocean views and overlooks the large pool. This elegant unit features a fully furnished gorgeous kitchen and is...

    Pool
    FREE CANCELLATION

    $343 to $540/night

  26. CONDOMINIUM
    A3-1 Bedroom Beachfront

    A3-1 Bedroom Beachfront

    Kihei, HI

    Ma'alaea Surf, Unit A3 is a conveniently located ground floor condo, just steps from Sugar beach. This condo features a full kitchen and dining table. The master bedroom has a king sized bed. The large living room has expansive views and a flat...

    Pool
    FREE CANCELLATION

    $304 to $467/night

  27. CONDOMINIUM
    D3-1 Bedroom Beachfront

    D3-1 Bedroom Beachfront

    Kihei, HI

    Ma'alaea Surf, Unit D3 is an ideally located ground floor unit, approximately 5 steps from the white sandy beach. This well-appointed unit features a fully furnished kitchen, large master suite with king size bed and a queen size sofa bed in the...

    Pool
    FREE CANCELLATION

    $304 to $467/night

  28. CONDOMINIUM
    H2-1 Bedroom Beachfront

    H2-1 Bedroom Beachfront

    Kihei, HI

    Ma'alaea Surf, Unit H2 - Beautifully appointed, H2 is an ideally located ground floor unit, approximately 5 steps from the white sandy beach. This comfortable unit features a contemporary kitchen and a large living area that looks out on the ocean....

    Pool
    FREE CANCELLATION

    $304 to $467/night

  29. CONDOMINIUM
    H3-1 Bedroom Beachfront

    H3-1 Bedroom Beachfront

    Kihei, HI

    Ma'alaea Surf, Unit H3 is a conveniently located ground floor condo, just steps from our large pool and Sugar beach. This condo features a full kitchen and dining table. The master bedroom has a king sized bed. The large living room has expansive...

    Pool
    FREE CANCELLATION

    $304 to $467/night

  30. CONDOMINIUM
    Pikake A-4

    Pikake A-4

    Lahaina, HI

    An incredibly comfortable unit! This renovated one bedroom unit fronts directly on a beautiful white sand beach. You'll have just enough lawn area to stretch out and shake the sand off before stepping directly into your beautiful ocean side living...

    FREE CANCELLATION

    $161 to $308/night