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
    Kapalua Bay Villa 23G2

    Kapalua Bay Villa 23G2

    Lahaina, HI

    Hear the ocean just steps away as you enjoy the view from your vacation villa. 23g2 is a luxury villa, fully furnished and beautifully renovated in 2005. Expansive, unobstructed ocean views facing Moloka'i. 1 bedroom, 1 bathroom, 1247 sq ft of...

    Pool
    FREE CANCELLATION

    $310 to $863/night

  2. CONDOMINIUM
    Maui Eldorado: Maui Condo B105

    Maui Eldorado: Maui Condo B105

    Kaanapali, HI

    Enjoy this spacious 1 bedroom almost 1000 sq ft in the Kaanapali beach resort area Short walk to Whaler's Village shops, restaurants & Kaanapali beach. The only resort with exclusive beachfront clubhouse & full kitchen right on the beach - ice...

    Pool
    FREE CANCELLATION

    $220 to $502/night

  3. CONDOMINIUM
    Maui Vista #1-319

    Maui Vista #1-319

    Kihei, HI

    Maui Vista is a lovely complex located across the street and literally a 3-minute walk from this unit to Charley Young Beach - voted one of the most beautiful beaches in the world. Connected to Charlie Young Beach is the famous Kamaole Beach #1....

    Pool
    FREE CANCELLATION

    $184 to $242/night

  4. CONDOMINIUM
    Kihei Garden Estates #H-203

    Kihei Garden Estates #H-203

    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

    $168 to $290/night

  5. CONDOMINIUM
    Maui Eldorado Condo J216

    Maui Eldorado Condo J216

    Kaanapali, HI

    This fully furnished garden view studio is located in the heart of Kaanapali at the Maui Eldorado Resort J216. Short walk to Whaler's Village shops and restaurants and enjoy onsite exclusive beachfront clubhouse with full kitchen, snorkeling at...

    Pool
    FREE CANCELLATION

    $176 to $377/night

  6. HOUSE
    Ho'o Maluhia

    Ho'o Maluhia

    Kailua Kona, HI

    This beautiful home features luxury and artistic touches to add a splash of sophistication to your vacation. The beautiful layout, wood floors and cool tiles fill the house. The master bedroom is located on the upper level. This room includes a...

    Pool

    $444 to $730/night

  7. CONDOMINIUM
    Kapalua Bay Villa 34B-4

    Kapalua Bay Villa 34B-4

    Lahaina, HI

    The Breathtaking views from this fabulous villa is just one of the reason Kapalua is the premier spot for your Hawaiian holiday. The white sand beaches, championship golf course, award winning restaurants are just a few things to dream of before you...

    Pool
    FREE CANCELLATION

    $415 to $1,079/night

  8. CONDOMINIUM
    Puu Poa 401

    Puu Poa 401

    Princeville, HI

    Romantic, AIR CONDITIONED (a/c in living room and master bedroom), totally private, luxury penthouse that guarantees an unequaled experience! The epitome of gracious living, capturing panoramic views of the azure ocean and Bali Hai. The best of the...

    Pool
    FREE CANCELLATION

    $269 to $1,016/night

  9. TOWNHOUSE
    Waikoloa Beach Villas O4

    Waikoloa Beach Villas O4

    Waikoloa, HI

    Come and relax in our unique 3 bedroom, 3 bath floor plan. Amazing views with the beautiful ocean breeze. This property is one of a kind. It is a corner unit with lot's of space including 3 lanai's. We are located in the Waikoloa Beach Resort, just...

    Pool
    FREE CANCELLATION

    $333 to $654/night

  10. CONDOMINIUM
    Pohailani Maui 115

    Pohailani Maui 115

    Lahaina, HI

    Our remodeled villa has all of the modern amenities of home! It is situated half way between Kaanapali and Kapalua Bay with plenty of shopping and restaurants near by. This beautifully furnished 2 bedroom 1 bath condo sleeps up to 6 people and has a...

    Pool
    FREE CANCELLATION

    $199 to $281/night

  11. CONDOMINIUM
    Maui Eldorado Condo J100

    Maui Eldorado Condo J100

    Kaanapali, HI

    Don't miss this rare opportunity to relax in this privately-owned two bedroom two bath spacious 1500 square foot Maui condo - Maui Eldorado J100!! Situated in the heart of Kaanapali, short walk to world class shopping and restaurants at Whaler's...

    Pool
    FREE CANCELLATION

    $370 to $816/night

  12. CONDOMINIUM
    Kona Plaza 112

    Kona Plaza 112

    Kailua Kona, HI

    Steps to the ocean, shops & restaurants — enjoy life on Alii Drive in Historic Kailua Kona Village! Tropically furnished, this first-floor 2 bedroom / 2 bath retreat is close to elevator and amenities. Throw open the large sliders and the open...

    Pool

    $304 to $482/night

  13. HOUSE
    Kahana Sunset E6

    Kahana Sunset E6

    Kahana, HI

    Come enjoy paradise in this recently renovated two-bedroom, two and a half bath condominium in West Maui, Hawaii. With a panoramic view of the ocean, Kahana Sunset Condo, Unit E-6, is just steps away from a secluded beach. The two-level condo, which...

    Pool

    $276 to $332/night

  14. CONDOMINIUM
    Maui Kamaole #G-210

    Maui Kamaole #G-210

    Kihei, HI

    Maui Kamaole #G-210 is a second floor 2 bedroom, 2 bathroom, ocean view unit with air conditioning throughout, a full kitchen with dishwasher, washer/dryer, TV/DVD, a telephone, and complimentary wireless Internet. Extra large floor plan with 1,244...

    Pool
    FREE CANCELLATION

    $377 to $493/night

  15. HOUSE
    Junior Suite Oceanfront #607

    Junior Suite Oceanfront #607

    Lahaina, HI

    This beautiful sixth floor oceanfront condo has a perfect view of Molokai. The tropical décor and king murphy bed help make your stay comfortable and relaxing. The fully equipped kitchen is great for a quick bite or a full meal. You will find...

    Pool Hot Tub
    FREE CANCELLATION

    $258 to $341/night

  16. VILLA
    Bay Villa 12B2 Ocean View

    Bay Villa 12B2 Ocean View

    Lahaina, HI

    Experience magnificent sunrises and sunsets from this enchanting villa. Perfectly positioned on the top floor with floor to ceiling windows streaming natural light over every surface. Two king size master bedrooms with en suites, a third bath with...

    Pool

    $594 to $1,063/night

  17. HOUSE
    Junior Suite Oceanfront #302

    Junior Suite Oceanfront #302

    Lahaina, HI

    This is a lovely Studio featuring a Queen sized Murphy Bed. The bed is easily placed into the wall to expand your living space if you so desire. One of Maui Kai’s little gems is unit 302. In colorful, floral designs, this room presents itself as a...

    Pool Hot Tub
    FREE CANCELLATION

    $278 to $341/night

  18. HOUSE
    Best Rate- 1 Bedroom Corner Oceanfront 12

    Best Rate- 1 Bedroom Corner Oceanfront 12

    Kaanapali, HI

    One Bedroom Corner - King Bed, NO sofa bed, enclosed lanai which makes the unit , Flat screen TV - hardwood floors; Livingroom is tiled in white. This condo will accommodate a maximum of two people, four with queen areo bed as extra bedding. The...

    Pool Hot Tub
    FREE CANCELLATION

    $351 to $423/night

  19. HOUSE
    Kahana Sunset E8

    Kahana Sunset E8

    Kahana, HI

    E8 is our 2 bedroom/2 bath condo and has been completely remodeled and redecorated.The furnishings are beautiful and comfortable. Kahana Sunset is a small oceanfront property offering an amazing private beach, beautiful pool and gorgeous grounds....

    Pool

    $276 to $332/night

  20. HOUSE
    Blue Kehena

    Blue Kehena

    Pahoa, HI

    Walking distance to Kehena Black Sand Beach, a clothing optional destination beach, Blue Kehena sits in the verdant jungle of the lush Kehena neighborhood. Elegant and exotic, the décor in Blue Kehena hearkens back to both missionary Hawaii and...

    $292 to $315/night

  21. CONDOMINIUM
    Waikiki Sunset Suite 2404

    Waikiki Sunset Suite 2404

    Waikiki, HI

    Partial Ocean View Waikiki Sunset Condo, Free Parking & Wifi Soak in the view from this high level condo. The view from the lanai is of Diamond Head Crater and Kapiolani Park to the left and the ocean to the right. This condo suite is one block...

    Pool

    $146 to $236/night

  22. CONDOMINIUM
    Paki Maui 316

    Paki Maui 316

    Lahaina, HI

    Enjoy your Maui vacation from the Paki Maui Oceanfront Resort! This gorgeous 1 bedroom, 1 bath, lush garden view condo is the perfect place for singles, couples or small families looking to experience and explore the island. Equipped with a...

    Pool
    FREE CANCELLATION

    $136 to $478/night

  23. CONDOMINIUM
    Hale Kamaole #264

    Hale Kamaole #264

    Kihei, HI

    Great Ocean and mountain Views. Two bedroom with loft. Upstairs master bedroom has king bed, downstairs bedroom has two twin beds, with queen hide-a-bed in living room. Loft has twin bed. Kitchen and Bathrooms have new cabinets. Bathrooms provide...

    Pool
    FREE CANCELLATION

    $269 to $379/night

  24. CONDOMINIUM
    E6-2 Bedroom Oceanfront Townhouse

    E6-2 Bedroom Oceanfront Townhouse

    Kihei, HI

    Ma'alaea Surf, Unit E6 - WHAT A VIEW! Sunsets on the lanai….Stunning views of the ocean and the West Maui Mountains… This 2 bedroom 2 bath second floor private condo sleeps 4 on comfortable Cal King beds, and is on a property built in the unique...

    Pool
    FREE CANCELLATION

    $343 to $540/night

  25. 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

  26. 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

  27. CONDOMINIUM
    Kaanapali Royal G102

    Kaanapali Royal G102

    Lahaina, HI

    Spend your dream Maui vacation here with us at the Kaanapali Royal G102!! You can spend your days relaxing in Kaanapali on your spacious lanai steps away from the pool, or walk to the beach for a swim or snorkel with the sea turtles at famous Black...

    Pool
    FREE CANCELLATION

    $274 to $605/night

  28. CONDOMINIUM
    Kuleana 310

    Kuleana 310

    Lahaina, HI

    Enjoy Spectacular views as you relax on the lanai in this newly updated unit. Beautifully landscaped grounds on the water. Hear the waves rolling in while you enjoy this upgraded unit with granite counter tops in the kitchen and bath and tile floors...

    Pool
    FREE CANCELLATION

    $161 to $331/night

  29. CONDOMINIUM
    Kauhale Makai 529

    Kauhale Makai 529

    Kihei, HI

    Come stay and relax at this newly renovated 1bd/1ba condo. This unit offers all the comforts of home with its WiFi, Cable, DVD Player, AC in the living room, and Ceiling Fans throughout. You'll also get to enjoy the fully-stocked kitchen, on-site...

    Pool Hot Tub
    FREE CANCELLATION

    $171 to $651/night

  30. HOUSE
    O'oma Plantation

    O'oma Plantation

    Kailua Kona, HI

    Why book individual resorts or condos when your whole group can enjoy a mansion in paradise? Enjoy exceptional panoramic coastal views from the private and quiet custom home at the O’oma Plantation. This large home is the perfect escape for a...

    Pool

    $1,179 to $1,664/night