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
    Kihei Garden Estates #E-102

    Kihei Garden Estates #E-102

    Kihei, HI

    Kihei Garden Estates is a lovely property right across the street from Waiohuli Beach. Kihei Garden Estates boasts a family friendly gathering area, seating up to 25 people to your barbecue feast under the covered pavilion. Enjoy this full outdoor...

    Pool Hot Tub
    FREE CANCELLATION

    $133 to $244/night

  2. CONDOMINIUM
    Aina Nalu K 205

    Aina Nalu K 205

    lahaina, HI

    AINA NALU K-205 Welcomes you with Aloha... This unique condo, in the heart of Old Lahaina Town, is a perfect vacation spot! K-205 was remodeled with the touch of ALOHA in 2017. Included in our fabulous price are many owner-supplied extras such...

    Pool Hot Tub
    FREE CANCELLATION

    $175 to $239/night

  3. VILLA
    Villa Cinco Resort at Kona Plantation Estates

    Villa Cinco Resort at Kona Plantation Estates

    Kailua Kona, HI

    This Villa is the owner’s primary residence under section 121 of IRC. The owners offer it for rent during limited periods. As such, it is Exempt from STVR rules, so it has no STVR registration #. TAT is TA-185-465-4464-01 . Villa operates in...

    Pool Hot Tub
    FREE CANCELLATION

    $759 to $760/night

  4. CONDOMINIUM
    Palms at Wailea #2305

    Palms at Wailea #2305

    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

    $196 to $347/night

  5. VILLA
    3BD Hali'ipua Villa (108) at Four Seasons Resort Hualalai

    3BD Hali'ipua Villa (108) at Four Seasons Resort Hu...

    Kailua Kona, HI

    Among the newest additions to the exclusive Four Seasons Resort Hualalai, this ocean-view villa provides the perfect setting for a romantic getaway for two or a relaxing retreat to paradise for two couples. The villa boasts over 2,600 square feet of...

    Pool Hot Tub

    $1,056 to $3,452/night

  6. CONDOMINIUM
    Palm Villas (H23) at Mauna Lani 2 Bedrooms + Loft

    Palm Villas (H23) at Mauna Lani 2 Bedrooms + Loft

    Kamuela, HI

    This beautifully decorated 2 bedroom, 2 bath, plus large spacious loft property is located in Palm Villas, a privately gated, small group of condominium homes, centrally located in the heart of the fabulous Mauna Lani Resort. This exceptional unit...

    Pool Hot Tub

    $393 to $962/night

  7. CONDOMINIUM
    Aina Nalu B106- Extremely Rare Unit

    Aina Nalu B106- Extremely Rare Unit

    Lahaina, HI

    October Discount - $15 off per night - Now through October 31! Aina Nalu B-106 features a queen bed, a dining space for two, and a well-equipped kitchenette with gorgeous stone flooring and granite counter tops. Its full bath includes a large,...

    Pool Hot Tub

    $243 to $738/night

  8. CONDOMINIUM
    Noelani #110

    Noelani #110

    Lahaina, HI

    Not one, but two oceanfront pools and a Jacuzzi, what more can you ask for? Unit 110 is a ground floor unit with washer and dryer. New kitchen cabinets and counter tops. You'll love to just walking out from your private lanai right into the...

    Pool Hot Tub
    FREE CANCELLATION

    $296 to $426/night

  9. APARTMENT
    Golf Course Views & Private! Lovely Renovated 2 Bed/2 Bath- Elima Lani 207

    Golf Course Views & Private! Lovely Renovated 2 Bed/...

    Waikoloa, HI

     This stunning 2 bedroom, 2 bathroom condo with gorgeous golf course views has everything you need for a relaxing vacation. The unit has been exquisitely remodeled from top to bottom. Beautiful new floors, cabinets and counters along with all brand...

    Pool Hot Tub
    FREE CANCELLATION

    $152 to $164/night

  10. HOUSE
    Happy Leilani Hale

    Happy Leilani Hale

    Kailua Kona, HI

    Tucked into the side of the mountain just above Kona at a cooler 600 ft. elevation Happy Leilani Hale has a zen feel to it as you look out over the blue pacific and feel the Soft ocean breezes take you away from it all. Enter through the Asian...

    Pool Hot Tub

    $425 to $729/night

  11. CONDOMINIUM
    Wai'ula'ula A102

    Wai'ula'ula A102

    Kamuela, HI

    Your visit to our vacation home will capture the essence of Hawaii. We are located along the Big Island’s exclusive golden Kohala Coast. Play golf on the emerald fairways of the renowned Mauna Kea Resort courses. Experience Kauna’oa and Hapuna,...

    Pool Hot Tub
    FREE CANCELLATION

    $525 to $1,205/night

  12. CONDOMINIUM
    Waikoloa Beach Villas B2

    Waikoloa Beach Villas B2

    Waikoloa, HI

    Come share the enjoyment of our home away from home in Hawaii! We fell in love with the Big Island 30 plus years ago on our honeymoon and have been vacationing here ever since. We love bringing our children and grandchildren because this island...

    Pool Hot Tub
    FREE CANCELLATION

    $209 to $431/night

  13. CONDOMINIUM
    Vista Waikoloa G-104

    Vista Waikoloa G-104

    Waikoloa, HI

    Aloha! Welcome to our 2 bedroom, 2.5 bathroom spacious Hawaiian retreat at the beautifully landscaped Vista Waikoloa. Conveniently located in a relaxing and peaceful gated community, our condo is situated on the ground floor near the 4th green of...

    Pool Hot Tub
    FREE CANCELLATION

    $221 to $464/night

  14. CONDOMINIUM
    Vista Waikoloa B-302

    Vista Waikoloa B-302

    Waikoloa, HI

    Newly remodeled unit, master bedroom has a king bed, guest bedroom has 2 twins beds that can be converted to a king upon request. Master bath and a guest full bathroom. Queen size sleeper sofa. Fully stocked kitchen with a convection microwave...

    Pool Hot Tub
    FREE CANCELLATION

    $209 to $464/night

  15. CONDOMINIUM
    Waikoloa Beach Villas B22

    Waikoloa Beach Villas B22

    Waikoloa, HI

    Come share the enjoyment of our home away from home in Hawaii!? We fell in love with the Big Island 30 plus years ago on our honeymoon and have been vacationing here ever since. We love bringing our children and grandchildren because this island...

    Pool Hot Tub
    FREE CANCELLATION

    $234 to $464/night

  16. CONDOMINIUM
    Waikoloa Beach Villas H32

    Waikoloa Beach Villas H32

    Waikoloa, HI

    Our unit is across from the Queens’ Market Place shopping village and has views of the golf course & lake. It is an elegant 2 bedroom, 2 bath top floor vacation retreat with all the comforts of your own home, including gourmet-equipped kitchen,...

    Pool Hot Tub
    FREE CANCELLATION

    $234 to $476/night

  17. CONDOMINIUM
    Kaanapali Alii 456

    Kaanapali Alii 456

    Lahaina, HI

    Our Luxury Ocean View condo is PRIVATELY MANAGED. Our condo is not in the Rental Program, so rest assure that our condo photos that you see here, is the one that you will rent from us. The condo unit is located in building 4 on the 5th floor end...

    Pool Hot Tub
    FREE CANCELLATION

    $563 to $1,500/night

  18. CONDOMINIUM
    Makahuena 2202

    Makahuena 2202

    Koloa, HI

    The Poipu vacation rentals at Makahuena Point are located in the most southern point on the island, from which you can watch both the sunrise and sunset. Makahuena Point has crashing waves and beautiful splashing surf, with only a short walk to...

    Pool Hot Tub
    FREE CANCELLATION

    $157 to $779/night

  19. CONDOMINIUM
    Nohonani #300

    Nohonani #300

    Lahaina, HI

    Nohonani 300 has recently completed a brand new renovation. Improvements include new carpeting and beautiful furnishings. This is an end unit on the third floor giving added privacy and a spectacular crows nest view of the outer islands and golden...

    Pool Hot Tub
    FREE CANCELLATION

    $274 to $403/night

  20. 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

    $286 to $478/night

  21. CONDOMINIUM
    Kauhale Makai #330

    Kauhale Makai #330

    Kihei, HI

    Hawaiian for "Village By The Sea," the Kauhale Makai complex is an oceanfront property located in Kihei. This is one of a few buildings in the area with central air conditioning - not window units. This condo stays as cool as you like it. Kihei is...

    Pool Hot Tub
    FREE CANCELLATION

    $161 to $266/night

  22. CONDOMINIUM
    Maui Kamaole #J-219

    Maui Kamaole #J-219

    Kihei, HI

    Kamaole Beach III is just across the street 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...

    Pool Hot Tub
    FREE CANCELLATION

    $324 to $486/night

  23. CONDOMINIUM
    Hale Pumehana Ko Olina Beach Villa (O1202)

    Hale Pumehana Ko Olina Beach Villa (O1202)

    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. L I V E C A L E N D A R If the calendar shows as available, the Villa is not reserved...

    Pool Hot Tub

    $740 to $1,668/night

  24. CONDOMINIUM
    Hale Welo Ko Olina Beach Villa (B806)

    Hale Welo Ko Olina Beach Villa (B806)

    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 $1,500/night

  25. CONDOMINIUM
    Waikiki Banyan Tower 1 Suite 813

    Waikiki Banyan Tower 1 Suite 813

    Honolulu, HI

    Deluxe Condo 8th Floor Pool View, Free Parking/Wifi Renovated and modern deluxe condo suite with pool and partial Diamond Head Views! This is a corner unit which is larger than the standard sized suites. Harwood flooring in the living areas and...

    Pool Hot Tub

    $185 to $259/night

  26. CONDOMINIUM
    Papakea A307

    Papakea A307

    Lahaina, HI

    Highly upgraded West Maui Ka’anapali Papakea 1 bedroom, 1 full bathroom, third floor condo, 25 feet from the oceans edge. Watch the whales, sunsets, and the ocean from the kitchen, living room and lanai. Sleep to the sound of the waves. This condo...

    Pool Hot Tub

    $258 to $381/night

  27. CONDOMINIUM
    Papakea J103

    Papakea J103

    Lahaina, HI

    Quiet Garden Unit! Awesome Garden and Pond View! West Maui Kaanapali Papakea 2 bedroom, 2 bathroom, sleeps 6, ground floor condo 100 yards from the ocean's edge. Enjoy dinner or a cocktail with the awesome pond and garden view. Updated kitchen and...

    Pool Hot Tub

    $215 to $351/night

  28. 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

  29. CONDOMINIUM
    Papakea A309

    Papakea A309

    Lahaina, HI

    Direct Ocean Front! Sleep to the sound of the waves! West Maui Kaanapali Papakea 1 bedroom, 1 bathroom, sleeps 4, third floor corner condo 25 feet from the ocean's edge. Watch the whales, sunsets, and the ocean from the kitchen, living room and...

    Pool Hot Tub

    $234 to $357/night

  30. CONDOMINIUM
    Papakea A108

    Papakea A108

    Lahaina, HI

    This GROUND FLOOR, OCEANFRONT condo is just feet from ocean access. Completely remodeled kitchen, bathroom and living room, with queen size bed in the bedroom, and queen size convertible sofa bed in the living room. Relax with the 55" SMART blue...

    Pool Hot Tub

    $258 to $381/night