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
  1. CONDOMINIUM
    Kahaluu Bay Villas #304

    Kahaluu Bay Villas #304

    Kailua Kona, HI

    This beautiful, private top floor condo at Kahaluu Bay Villas is quite the gem. The unit has a well equipped kitchen and all the rooms are spacious with a balcony overlooking the pool and the ocean. The bedrooms and baths are wonderfully...

    Pool
    FREE CANCELLATION

    $327 to $388/night

  2. CONDOMINIUM
    Kona Isle D4

    Kona Isle D4

    Kailua Kona, HI

    Kona Isle D4 is a lovely, ground floor unit featuring a DIRECT oceanfront view from the living room, kitchen, and bedroom! BRAND NEW MATTRESS PURCHASED AS OF NOVEMBER 2018! This unit is located in the best building in the complex! No stairs,...

    Pool
    FREE CANCELLATION

    $202 to $204/night

  3. TOWNHOUSE
    Puamana Premier Platinum Townhouse 8-1

    Puamana Premier Platinum Townhouse 8-1

    Lahaina, HI

    Come stay with us and enjoy island living Puamana-style! Sip your morning tea on the lanai and watch the sun come up over the majestic West Maui Mountains. Play tennis, swim and surf at the beach, soak up the sun and cool off in the oceanfront...

    Pool
    FREE CANCELLATION

    $291 to $596/night

  4. CONDOMINIUM
    Fairway Villas Waikoloa O21

    Fairway Villas Waikoloa O21

    Waikoloa, HI

    Designer furnishings, tropical artwork, luxurious linens and toiletries! Outstanding accommodations await you. Conveniently located parking to condo and elevator. Well-appointed, spacious master bedroom features a comfy Cal-king size bed, with...

    Pool Hot Tub
    FREE CANCELLATION

    $197 to $464/night

  5. 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

  6. 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

  7. VILLA
    Waikoloa Beach Villas P32

    Waikoloa Beach Villas P32

    Waikoloa, HI

    We have traveled from our island home in Honolulu numerous times over the years to explore the Big Island. The Big Island offers a diversity of amazing sights including a huge selection of beautiful sunny beaches, snow-capped Mauna Kea, and an...

    Pool Hot Tub
    FREE CANCELLATION

    $197 to $407/night

  8. 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

  9. 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

  10. 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

  11. 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

  12. APARTMENT
    Blue Lagoon

    Blue Lagoon

    Kamuela, HI

    A Polynesian resort inspired estate with large heated pool and spa, ideal for a spacious getaway or large group. Upon entering through 10 ft mahogany gates, traversing a bridge over a Koi pond past a waterfall, you will be treated to the luxury...

    $2,743 to $6,408/night

  13. 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

  14. CONDOMINIUM
    Kihei Garden Estates #B-201

    Kihei Garden Estates #B-201

    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 Bar-B-Q feast under the covered pavilion. Enjoy this full outdoor...

    Pool Hot Tub
    FREE CANCELLATION

    $133 to $226/night

  15. CONDOMINIUM
    Maui Banyan #B-204

    Maui Banyan #B-204

    Kihei, HI

    Maui Banyan Resort is situated on 8 acres of beautifully landscaped grounds located in South Maui across the street from the popular Kamaole Beach Park II. This white sandy beach is perfect for swimming and snorkeling. It is a 5-minute drive to the...

    Pool Hot Tub
    FREE CANCELLATION

    $180 to $377/night

  16. CONDOMINIUM
    Island Surf #502

    Island Surf #502

    Kihei, HI

    Island Surf is located in the heart of Kihei, across the street from Kalama Park and Cove Park, and within walking distance of shops, restaurants, and activity shops. The Island Surf building itself has several restaurants and stores. There is a...

    Pool
    FREE CANCELLATION

    $157 to $342/night

  17. CONDOMINIUM
    Nohonani #105

    Nohonani #105

    Lahaina, HI

    Unit #105 is a two bedroom, two bath unit just steps away from the beach. The master bedroom has a king-size bed; and twin beds in the guest bedroom. Free parking and WiFi are provided as well. If you have ever dreamt of lying in bed and going to...

    Pool
    FREE CANCELLATION

    $274 to $353/night

  18. CONDOMINIUM
    Royal Kahana 812 1 Bdrm

    Royal Kahana 812 1 Bdrm

    Lahaina, HI

    Spectacular ocean views from the lanai of this eighth floor condominium. This spacious, one bedroom condo is filled with comfortable island décor. The bedroom features a new ultra comfortable queen size bed and ocean views. The living room has a...

    Pool
    FREE CANCELLATION

    $230 to $461/night

  19. CONDOMINIUM
    Royal Kahana 315

    Royal Kahana 315

    Lahaina, HI

    Aloha from paradise! We are excited to offer a much demanded 3rd level one bedroom suite at this popular West Maui resort! Our beautifully REMODELED condo has all of the amenities you would want on a tropical vacation (including AC and a washer and...

    Pool
    FREE CANCELLATION

    $179 to $346/night

  20. CONDOMINIUM
    Royal Kahana 107 1Bdrm

    Royal Kahana 107 1Bdrm

    Lahaina, HI

    Experience the true sense of ALOHA at the Royal Kahana Resort! We offer a much in demand ground level condo with all the amenities of home. This spacious one bedroom, one bathroom suite is elegantly REMODELED with beautiful island décor. It has a...

    Pool
    FREE CANCELLATION

    $199 to $423/night

  21. CONDOMINIUM
    Royal Kahana 119 Studio

    Royal Kahana 119 Studio

    Lahaina, HI

    Experience the true sense of ALOHA at the Royal Kahana Resort! We offer a much in demand ground level condo with all the amenities of home. This spacious studio suite (unit #119) is elegantly REMODELED with beautiful island décor. Royal Kahana...

    Pool Hot Tub
    FREE CANCELLATION

    $191 to $341/night

  22. CONDOMINIUM
    Sands of Kahana 316

    Sands of Kahana 316

    Lahaina, HI

    The Sands of Kahana has something for everyone! With an ocean front pool that the whole family will love and a pool just for children where the little ones can enjoy. After a adventuring Maui, make your way and relax in the Jacuzzi. There is a sand...

    Pool Hot Tub
    FREE CANCELLATION

    $249 to $930/night

  23. CONDOMINIUM
    Spinnaker 216C

    Spinnaker 216C

    Lahaina, HI

    Master has Cal King bed, flat screen tv/cable, Bedroom 2 has two twin beds. Kitchen includes stainless steel appliances, stove top, microwave, wall oven, coffee maker, granite countertops/island with stools. Fully tiled bathroom with walk-in shower....

    Pool Hot Tub
    FREE CANCELLATION

    $161 to $664/night

  24. CONDOMINIUM
    Kaleialoha 309

    Kaleialoha 309

    Lahaina, HI

    Come stay at the Kaleialoha Oceanfront Codominium!! This great direct oceanfront 1 bedroom, 1 bathroom condo offers the best of Hawaiian style living just a stones throw away from the beautiful blue pacific ocean! Enjoy the sounds of the waves right...

    Pool
    FREE CANCELLATION

    $174 to $321/night

  25. CONDOMINIUM
    Hololani A701

    Hololani A701

    Lahaina, HI

    Come and enjoy your Maui vacation at this beautiful 2 bedroom condo at the Hololani Oceanfront resort in wonderful West Maui! Bright blue is all you see as you enter this wonderful space! There is a perfect view of Maui’s majestic sister island of...

    Pool
    FREE CANCELLATION

    $261 to $474/night

  26. CONDOMINIUM
    Kahana Sunset E4

    Kahana Sunset E4

    Lahaina, HI

    Come and enjoy the amazing views and sunsets at Kahana Sunset Oceanfront Condos!! This beautiful 2-bedroom, 2-bathroom condo with breathtaking views of the ocean provides everything you need for your vacation in paradise. With a fully equipped...

    Pool Hot Tub
    FREE CANCELLATION

    $224 to $500/night

  27. 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

    $249 to $820/night

  28. CONDOMINIUM
    Kaleialoha 202

    Kaleialoha 202

    Lahaina, HI

    Come stay with us at the beautiful Kaleialoha Oceanfront Resort!! This spacious studio condominium has all of the comforts of home. It's the perfect place for an active family vacation or a couple looking for a romantic getaway. The living area has...

    Pool
    FREE CANCELLATION

    $148 to $489/night

  29. CONDOMINIUM
    Royal Kahana 618

    Royal Kahana 618

    Lahaina, HI

    Aloha and welcome to our Maui paradise! This is a 6th floor studio with AC offers amazing views of the Pacific Ocean with views of our neighboring island. Enjoy your morning coffee and/or afternoon cocktails on the lanai while savoring the...

    Pool
    FREE CANCELLATION

    $124 to $456/night

  30. CONDOMINIUM
    Napili Point A8

    Napili Point A8

    Lahaina, HI

    Brand new tile throughout the entire condo! The bedroom has a comfortable King bed and TV to help you relax at the end of your day. The bathroom has a nice large vanity area separate from the toilet and walk-in shower area. The living room has a...

    Pool
    FREE CANCELLATION

    $259 to $469/night