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.

Filter by Region:

Filter by Amenities:

Filter by Entertainment:

Close Filters

Search results

  1. CONDOMINIUM
    Mahana 701

    Mahana 701

    Lahaina, HI

    Beautiful 7th floor 2br/2ba condominium at The Mahana at Kaanapali provides everything you need for your vacation in paradise. Equipped with granite counter tops, beautiful tile floors, central A/C, WiFi, flat screen TV, stocked kitchen, and...

    Pool
    FREE CANCELLATION

    $499 to $1000/night

  2. CONDOMINIUM
    Kaanapali Royal #A201 (MAUI)

    Kaanapali Royal #A201 (MAUI)

    Lahaina, HI

    Come stay at our modernly decorated ground floor unit at the kaanapali royal. This 1560 sq. Ft condo was extensively remodeled, and features a spacious floor plan that expands to sweeping golf course views.  Travertine countertops, stone and wood...

    Pool Hot Tub

    $498 to $1255/night

  3. HOUSE
    Pua Nui

    Pua Nui

    Princeville, HI

    PUA NUI - House of Abundant Flowers TA-149-751-5008-01 This extremely lovely and comfortable Princeville home has four bedrooms - including two master suites, and three full baths. The home sleeps 8 guests. The huge lanai overlooks the lush...

    $498 to $651/night

  4. CONDOMINIUM
    Honua Kai Konea 1026

    Honua Kai Konea 1026

    Lahaina, HI

    NOTE: As of 2/6/18 construction of 72 Townhomes has commenced behind the Konea building at Honua kai. This condo overlooks the construction site. There may be noise and dust on work days during construction hours from 8am to 5pm. This beautiful...

    Pool Hot Tub
    FREE CANCELLATION

    $496 to $1479/night

  5. CONDOMINIUM
    Kaanapali Alii 433 The Royal Jewel

    Kaanapali Alii 433 The Royal Jewel

    Lahaina, HI

    Kaanapali Alii is a luxury oceanfront resort located on World Famous Kaanapali's white sandy beach.  Kaanapali Alii's oceanfront towers are set on a wide stretch of Kaanapali Beach, a 3-minute walk from Whalers Village and 36 holes of championship...

    Pool Hot Tub
    FREE CANCELLATION

    $495 to $675/night

  6. CONDOMINIUM
    Wailea Elua Unit #0202

    Wailea Elua Unit #0202

    Wailea, HI

    Wailea Elua Village is an exclusive beachfront property located in the heart of the resort community of Wailea. This relaxing low-density property consists of two-story buildings terraced over twenty-four acres of immaculate tropical landscaping....

    Pool

    $494 to $1065/night

  7. HOUSE
    Holua Kai #34

    Holua Kai #34

    Kailua Kona, HI

    Situated in the exclusive, gated oceanfront community of Holua Kai, this luxurious and inviting home provides the perfect setting for your Hawaiian getaway. The home comfortably accommodates six and is just a 10-minute walk from Keauhou Bay, the...

    Pool

    $493 to $909/night

  8. CONDOMINIUM
    Hanalei Bay Resort 52012

    Hanalei Bay Resort 52012

    Princeville, HI

    Hanalei Bay Resort 52012: Includes both of the elegant, recently updated, air-conditioned suites below, at a savings compared to renting separately. Close the connecting door for complete privacy, or open for a large shared apartment. Combined, the...

    Pool Hot Tub

    $493 to $551/night

  9. CONDOMINIUM
    Wailea Elua #701

    Wailea Elua #701

    Kihei, HI

    The Wailea Elua is the premier ocean front property in Wailea. Situated right on Ulua Beach, it has one of the best locations in Wailea. There are miles of spectacular walking paths that follow the ocean  In addition the property has two swimming...

    Pool
    FREE CANCELLATION

    $493 to $922/night

  10. HOUSE
    Holua Kai #32

    Holua Kai #32

    Kailua Kona, HI

    Experience the ultimate Big Island luxury getaway in this plantation-style home in Holua Kai, Keauhou's exclusive new gated community, where oceanfront golf, panoramic views of the coast, and stunning sunsets await. This brand new home is less than...

    Pool

    $493 to $909/night

  11. CONDOMINIUM
    Honua Kai-Konea #539

    Honua Kai-Konea #539

    Lahaina, HI

    Ocean views from the Konea tower in North Ka'anapali with a wrap-around corner Lanai. The stainless steel appliances, granite counter tops and modern decor compliment this brand new 2 bedroom condo at a brand new resort. In addition to the flat...

    Pool

    $493 to $1467/night

  12. APARTMENT
    Mauka Lani (KAUAI)

    Mauka Lani (KAUAI)

    Princeville, HI

    This villa at Villas of Kamalii, Princeville, is an upscale luxurious and tropically decorated, two bedroom, three bath Villa. Two large en-suite bedrooms, one queen with a shower and one king with jacuzzi tub downstairs, and a third reading room on...

    Pool
  13. CONDOMINIUM
    Kapalua Golf Villas 12T5

    Kapalua Golf Villas 12T5

    Kapalua, HI

    Relax and enjoy the tranquil setting of this luxurious Kapalua Golf Villa. Let the gorgeous greenery captivate and soothe your soul. This unit has been remodeled with only top of the line materials and furnishings and is well apointed. Spend your...

    Pool
    FREE CANCELLATION

    $493 to $626/night

  14. CONDOMINIUM
    Kaanapali Shores #255

    Kaanapali Shores #255

    Lahaina, HI

    This Hawaiian themed condo has ocean views from the lanai and both bedrooms in Ka'anapali. Remodeled and updated. The guest bathroom has a glass block walk-in shower only-no tub. Bring your DVD's from home and watch them on the flat screen TV in the...

    Pool

    $493 to $800/night

  15. CONDOMINIUM
    Papakea A404

    Papakea A404

    Lahaina, HI

    One of the nicest penthouse units at Papakea Resort. From your lanai and the master bedroom, watch the whales play and the honu (turtles) swim. The KING bed in master bedroom allows you to sleep to the sounds of the ocean just 25 feet away. The...

    Pool Hot Tub

    $491 to $707/night

  16. CONDOMINIUM
    Sands of Kahana #292

    Sands of Kahana #292

    Kahana, HI

    9th Floor Ocean Front 3 bedroom, 3 bath Penthouse at the beautiful Sands of Kahana with exquisite views of the neighboring islands. This spacious 3 bedroom condo allows for plenty of room and seating areas for the entire family. A fully equipped...

    Pool

    $487 to $1183/night

  17. HOUSE
    Kona Bay Seaclusion-Oceanfront

    Kona Bay Seaclusion-Oceanfront

    Kailua Kona, HI

    Beautifully appointed "like new" 2 bedroom 2.5 bath oceanfront home with pool. Gourmet kitchen and huge deck for tanning, dining & sunset cocktails. Upstairs master has shower & hot tub. Sliding doors disappear into walls for the ultimate "on the...

    Pool

    $486 to $547/night

  18. COTTAGE
    2 Charming Cottages on the Ocean

    2 Charming Cottages on the Ocean

    Kamuela, HI

    Offering an idyllic oceanfront setting in the town of Puako, this rental sleeps up to six guests between the 1BR cottage and a separate studio. Perfect for groups seeking extra privacy, this charming seaside compound boasts unobstructed views of the...

    FREE CANCELLATION

    $486 to $820/night

  19. CONDOMINIUM
    Hale Ko Olina Beach Villa (O222)

    Hale Ko Olina Beach Villa (O222)

    Kapolei, HI

    Are you ready to experience the balmy tranquility of the Beach Villas at Ko Olina? This luxury 2nd floor Beach Villa in the Ocean Tower is ideally situated next to the Lap/Quiet Pool and a short walk to the beach, pool areas, fitness center, dry...

    Pool

    $485 to $1500/night

  20. CONDOMINIUM
    O-805: Hale Makai Ko Olina Beach Villa

    O-805: Hale Makai Ko Olina Beach Villa

    Kapolei, HI

    Overview: This 3 BD, 2.5 BA luxury villa on the 8th floor of the Ocean Tower has stunning direct ocean views and is conveniently located just 20 miles from Honolulu International Airport on the beautiful southwestern shores of Oahu. The four...

    Pool Hot Tub

    $485 to $1668/night

  21. CONDOMINIUM
    Ko Olina Beach Villa B806

    Ko Olina Beach Villa B806

    Kapolei, HI

    Beachfront Living at its finest! This 2 bedroom, 2 bath Villa is located in the beautiful Ko Olina Resort on the quiet West side of Oahu. The Beach Villas are the newest, and only, beachfront condominiums available on the island in 25 years. You...

    Pool Hot Tub

    $485 to $1500/night

  22. CONDOMINIUM
    Maui Kaanapali Villas #A101

    Maui Kaanapali Villas #A101

    Kaanapali, HI

    Luxury + Privacy = Our Maui Kaanapali Villa Vacation Rental Home. Our Villa, located on the ocean side ground level of Aloha Tower, represents the finest in gracious Hawaiian living. Featuring soaring ceilings and fine Asian art throughout, this 2...

    Pool

    $481 to $1167/night

  23. CONDOMINIUM
    Wai'ula'ula D201 Condominium

    Wai'ula'ula D201 Condominium

    Waimea, HI

    Welcome to Wai'ula'ula at the Mauna Kea Resort! Your vacation will truly be one to remember in this beautifully decorated condominium in the gated community of Wai'ula'ula, located on the Hapuna Golf Course. This recently built luxury development...

    Pool
    FREE CANCELLATION

    $481 to $1174/night

  24. APARTMENT
    Beach Villas at Kahalu'u 2-101

    Beach Villas at Kahalu'u 2-101

    Kailua Kona, HI

    Beach Villas at Kahaluu-. 2 bedroom, 2 bath condo with Central AC, Shared Infinity Pool, Walk to Beach Family and friends will love staying at The Beach Villas at Kahalu'u. This 2 bedroom/2 bathroom vacation home features an ocean view and can...

    Pool

    $481 to $647/night

  25. CONDOMINIUM
    Hale Kai O'Kona

    Hale Kai O'Kona

    Kailua Kona, HI

    Hale Kai O'Kona is an exclusive oceanfront Hawaii vacation home one mile south of the town of Kailua-Kona, on the Big Island of Hawaii. Our home is a 2400 Sq. Ft. end property with no connecting walls. The beauty and privacy of this 4 bedroom, 3...

    Pool

    $479 to $642/night

  26. CONDOMINIUM
    Wailea Elua Unit #2107

    Wailea Elua Unit #2107

    Wailea, HI

    A Note From the Owner: You will love the extra space in this remodeled supersized two-bedroom, two-bath Elua condo. With nearly 300 square feet more than the typical Elua two-bedroom unit, you can spread out, relax and truly enjoy your stay in...

    Pool Hot Tub

    $477 to $897/night

  27. VILLA
    Bay Villa 19G4 Gold Beach Front

    Bay Villa 19G4 Gold Beach Front

    Kapalua, HI

    This lovely ocean front beauty will make you feel like you are on top of the world! Too many upgrades to list. Beautiful new kitchen, granite, and brushed stainless; new furniture, 60" flat screen and central AC throughout. Inside, the king size...

    Pool

    $475 to $780/night

  28. HOUSE
    1332 Mokolea Dr Home

    1332 Mokolea Dr Home

    Kailua, HI

    Located in the upscale neighborhood of Lanikai, this 3BR/2BA ocean tree house is strolling distance to Lanikai Beach — regarded as one of the world's most beautiful top beaches, with its flour-soft white sands, cooling ocean breezes, and pristine...

    FREE CANCELLATION

    $473 to $803/night

  29. CONDOMINIUM
    Wai'ula'ula Ridge J202

    Wai'ula'ula Ridge J202

    Waimea, HI

    Wai'ula'ula, located on the 'mauka' or mountain side of the highway in the Uplands development, accessed through the Hapuna Prince Resort entrance. This gated community is surrounded by the fairways of the Hapuna golf course and boasts panoramic...

    Pool

    $473 to $817/night

  30. 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...