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
    Surfs Up (3-Bedroom Condo)

    Surfs Up (3-Bedroom Condo)

    Waikoloa, HI

    Stunning mountain and garden views surround you in this newly renovated, well-appointed end unit ground floor Villa, our second home. A spacious 3 bedroom, 1407 sq ft offers room for everyone. The Villa sleeps up to six people (king, queen and two...

    Pool Hot Tub

    $302 to $618/night

  2. VILLA
    Waikoloa Colony Villas 403

    Waikoloa Colony Villas 403

    Waikoloa, HI

    Spring Special - 10% off from April 1-June 15 This beautiful two bedroom townhome style property is in the prime location of Colony Villas in the desirable Waikoloa Beach Resort area. Colony Villas is an ideal vacation destination with two...

    Pool Hot Tub

    $302 to $607/night

  3. CONDOMINIUM
    Maui Kamaole #F-207

    Maui Kamaole #F-207

    Kihei, HI

    Kamaole Beach #3 is just across from the upscale Maui Kamaole. This property features lush tropical landscaping, two gorgeous pool areas with hot tubs and water features. There are gas grills peppered throughout the property and tennis courts...

    Pool Hot Tub
    FREE CANCELLATION

    $302 to $418/night

  4. CONDOMINIUM
    Hale Ohana Aloha

    Hale Ohana Aloha

    Waikoloa, HI

    Big Island dreams begin at Hali'i Kai 7D, an ocean-view vacation condominium at renowned Waikoloa Beach Resort. Ideal for group getaways of up to six people, this 2-bedroom, 2-bath condo features an updated interior, access to impeccable resort...

    Pool Hot Tub

    $302 to $504/night

  5. CONDOMINIUM
    Mauna Kai 7B

    Mauna Kai 7B

    Princeville, HI

    Dream. Believe. Discover. These are the words imprinted on several walls of Mauna Kai #7B, and this architecturally bold villa lends itself to all three activities quite nicely. It’s a two level unit with a large lanai facing the Makai Golf Course...

    Pool Hot Tub

    $301 to $482/night

  6. CONDOMINIUM
    Hanalei Bay Resort 6302

    Hanalei Bay Resort 6302

    Princeville, HI

    This unit has among the most extraordinary views in the entire resort. A top floor unit, the view from every room is exceptional, encompassing the entire expanse of the bay, from the mountains behind Hanalei to “Bali Hai” peak and the ocean...

    Pool Hot Tub

    $301 to $355/night

  7. CONDOMINIUM
    Sugar Beach #406

    Sugar Beach #406

    Kihei, HI

    **The Pool will be CLOSED beginning September 10th, through September 17th, 2018. In 2019 the pool will be closed September 9th, through September 16th. Each year the pool will be closed for one week, starting on the second Monday of the month....

    Pool Hot Tub
    FREE CANCELLATION

    $299 to $412/night

  8. CONDOMINIUM
    Sugar Beach 308

    Sugar Beach 308

    Kihei, HI

    **The Pool will be CLOSED beginning September 10th, through September 17th, 2018. In 2019 the pool will be closed September 9th, through September 16th. Each year the pool will be closed for one week, starting on the second Monday of the month....

    Pool Hot Tub
    FREE CANCELLATION

    $299 to $412/night

  9. CONDOMINIUM
    Maui Banyan #G-105

    Maui Banyan #G-105

    KIHEI, HI

    The Elevator for G & H building will be closed for Elevator Modernization starting at 10:00 am Monday September 10, 2018. We will have a bellman to help with luggage. Beautifully furnished one bedroom Garden view Condo. The bedroom has a king bed...

    Pool Hot Tub
    FREE CANCELLATION

    $299 to $360/night

  10. CONDOMINIUM
    Honua Kai Konea 924

    Honua Kai Konea 924

    Kaanapali, 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. NOW FEATURING HIGH...

    Pool Hot Tub
    FREE CANCELLATION

    $299 to $1,003/night

  11. CONDOMINIUM
    Papakea Unit #H103 Condo

    Papakea Unit #H103 Condo

    Lahaina, HI

    Welcome to: "Tranquility Maui Condo" This charming 2 bedroom Papakea condominium is located in "H" building near ponds and gardens. Great views from the beach and off to the neighbor islands of Lanai and Molokai. Tastefully decorated with Hawaiian...

    Pool Hot Tub
    FREE CANCELLATION

    $296 to $580/night

  12. CONDOMINIUM
    Kamaole Sands 05-107

    Kamaole Sands 05-107

    Kihei, HI

    Beauty and The Beach ~ Unit 5-107 is a fully remodeled, fully air conditioned ground level Condo in a lush tropical setting with a level of privacy rarely found in vacation Condo living ~ This premier Condominium home is close to all property...

    Pool Hot Tub
    FREE CANCELLATION

    $296 to $350/night

  13. CONDOMINIUM
    Hali'i Kai 19G Condominium

    Hali'i Kai 19G Condominium

    Waikoloa, HI

    Come and take a vacation in our new professionally designed townhome with everything you need to make your vacation the most memorable.. Hali'i Kai is located in the most famous Waikoloa Beach Resort nestled on the point with outstanding ocean views...

    Pool Hot Tub
    FREE CANCELLATION

    $295 to $741/night

  14. VILLA
    Hali'i Kai 18G Villa

    Hali'i Kai 18G Villa

    Waikoloa, HI

    Come and stay in our Beautiful Furnished Villa and the Hawaiian-themed artwork attitude shine in this gorgeous villa via air-conditioned living spaces, open stainless steel kitchen, the master has a king bed with a private bath and lanai, the 1st...

    Pool Hot Tub
    FREE CANCELLATION

    $295 to $741/night

  15. CONDOMINIUM
    Mahana 307

    Mahana 307

    Lahaina, HI

    This beautifully appointed unit has tile and bamboo flooring throughout. The updated kitchen has cherry pecan cabinets with self-closing drawers/doors, gorgeous granite counter tops, stainless steel appliances including a French door refrigerator...

    Pool Hot Tub
    FREE CANCELLATION

    $294 to $750/night

  16. CONDOMINIUM
    Kona Makai 1-301

    Kona Makai 1-301

    Kailua Kona, HI

    Kona Makai #1-301 is arguably the best condo in the entire complex. Being the top floor corner in building 1, the location is undeniably too perfect. Private & upgraded, this is direct oceanfront condo living at its finest. You can't get a better...

    Pool Hot Tub
    FREE CANCELLATION

    $292 to $740/night

  17. CONDOMINIUM
    Waikiki Dream Vacation

    Waikiki Dream Vacation

    Honolulu, HI

    Beautifully remodeled 2 bedroom 2 bath with large lanai facing Diamond Head with Ocean and Mountain Views. free assigned, covered and secure parking. One queen bed in master bedroom. 2 twins in the view suite can be put together. Located centrally...

    Pool Hot Tub

    $292 to $352/night

  18. CONDOMINIUM
    Palms at Wailea #704

    Palms at Wailea #704

    Wailea, HI

    The fabulous Keawakapu Beach is just a short 10 minute stroll from the Palms at Wailea. This beach is world famous for its great snorkeling, whale watching and strolling. The Palms at Wailea is a gorgeous property; lush with tropical landscaping....

    Pool Hot Tub
    FREE CANCELLATION

    $290 to $463/night

  19. CONDOMINIUM
    Palms at Wailea #2205

    Palms at Wailea #2205

    Kihei, HI

    We are pleased that our properties at the Palms at Wailea have been chosen to be featured in the number 1 selling book "Maui Revealed" and their website. These properties were chosen because of their superior quality and great rates! The fabulous...

    Pool Hot Tub
    FREE CANCELLATION

    $290 to $463/night

  20. CONDOMINIUM
    Palms at Wailea #2303

    Palms at Wailea #2303

    Wailea, HI

    We are pleased that our properties at the Palms at Wailea have been chosen to be featured in the number 1 selling book "Maui Revealed" and their website. These properties were chosen because of their superior quality and great rates! The fabulous...

    Pool Hot Tub
    FREE CANCELLATION

    $290 to $463/night

  21. CONDOMINIUM
    Maui Kamaole #A-202

    Maui Kamaole #A-202

    Kihei, HI

    Unit A-202 has been completely renovated. This renovation includes: the kitchen cabinets, granite countertops, new kitchen appliances; lighting, carpeting and new tile everywhere; redesigned bathrooms with walk-in showers, new bathroom cabinets and...

    Pool Hot Tub
    FREE CANCELLATION

    $289 to $405/night

  22. DUPLEX
    Diamond Head Duplex Unit #B

    Diamond Head Duplex Unit #B

    Honolulu, HI

    Your Manoa Valley crew of five will adore this lovely 2BR duplex. Unique Craftsman touches include captivating stained glass windows, while an outdoor shower provides added convenience. Find another full living room on the enclosed lanai and views...

    Hot Tub Pets OK
    FREE CANCELLATION

    $289 to $401/night

  23. CONDOMINIUM
    Maui Kamaole #A-207

    Maui Kamaole #A-207

    Kihei, HI

    Maui Kamaole #A207 is a beautifully furnished and decorated ocean view condo that has all the amenities to make your vacation in paradise perfect. The Lanai furniture is comfortable and is the best spot to start your morning and end an evening. It...

    Pool Hot Tub
    FREE CANCELLATION

    $289 to $451/night

  24. CONDOMINIUM
    Palms at Wailea #1101

    Palms at Wailea #1101

    Wailea, HI

    The fabulous Keawakapu Beach is just a short 10 minute stroll from the Palms at Wailea. This beach is world famous for its great snorkeling and long walking beach. The Palms at Wailea is a gorgeous property; lush with tropical landscaping. There is...

    Pool Hot Tub
    FREE CANCELLATION

    $289 to $493/night

  25. CONDOMINIUM
    Honua Kai 508

    Honua Kai 508

    Lahaina, HI

    HONUA KAI RESORT AND SPA SUITE 508 Welcomes you... This spacious one bedroom one bath plus den can accommodate up to six (6) guests … Included in our fabulous price are many owner-supplied extras such as: • Beach chairs (2) • Beach...

    Pool Hot Tub
    FREE CANCELLATION

    $288 to $608/night

  26. CONDOMINIUM
    Kapalua Ridge Villa #311

    Kapalua Ridge Villa #311

    Lahaina, HI

    This enchanting villa is the quiet retreat you have been yearning for! Spectacular ocean views and the quiet serenity of the resort will be an experience to remember. The views from this property will send your spirits soaring! You’ll feel a sense...

    Pool Hot Tub
    FREE CANCELLATION

    $288 to $1,956/night

  27. CONDOMINIUM
    Honua Kai 215

    Honua Kai 215

    Lahaina, HI

    HONUA KAI RESORT AND SPA SUITE 215 welcomes you with so much This spacious studio, 1 bath can accommodate up to 4 guests. Included in our fabulous price are many owner-supplied extras such as: • Beach chairs (2) • Beach umbrella • Beach...

    Pool Hot Tub
    FREE CANCELLATION

    $287 to $413/night

  28. TOWNHOUSE
    N Kaniku Townhouse Unit 2002

    N Kaniku Townhouse Unit 2002

    Kamuela, HI

    Located in the gated Kulalani community, this spacious 3BR/2.5BA is your Pacific paradise. Interiors include updated floors and towering ceilings throughout. Your rental offers prime outdoor living space with a lanai, as well as access to a shared...

    Pool Hot Tub
    FREE CANCELLATION

    $285 to $739/night

  29. CONDOMINIUM
    Palms at Wailea #305

    Palms at Wailea #305

    Wailea, HI

    The fabulous Keawakapu Beach is just a short 10 minute stroll from the Palms at Wailea. This beach is world famous for its great snorkeling and long white sandy shoreline. The Palms at Wailea is a gorgeous property; lush with tropical landscaping....

    Pool Hot Tub
    FREE CANCELLATION

    $284 to $429/night

  30. CONDOMINIUM
    Palms at Wailea #1902

    Palms at Wailea #1902

    Wailea, HI

    Enjoy your stay in paradise at The Palms at Wailea, a gorgeous property with lush, tropical landscaping and expansive lawn areas. The complex is conveniently located within short walking distance of popular restaurants, shops, and a spectacular...

    Pool Hot Tub
    FREE CANCELLATION

    $284 to $458/night