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
    Hale Kamaole #213

    Hale Kamaole #213

    Kihei, HI

    Ocean View. Completely remodeled condo, with fantastic kitchen, very spacious. Bathroom has walk-in shower enclosure. King bed in bedroom with new carpet & rattan bedroom furniture. Living room has rattan Hawaiian style furniture with queen...

    Pool
    FREE CANCELLATION

    $196 to $281/night

  2. CONDOMINIUM
    Cliffs 8205

    Cliffs 8205

    Princeville, HI

    Located in Princeville on the lush north shore of Kauai, Cliffs 8205 is the perfect home away from home (up to 4). This luxury condo has spectacular unobstructed ocean views, pleasant trade winds and a front row seat for whale watching. Relax in...

    Pool Hot Tub

    $253 to $301/night

  3. VILLA
    Bay Villa 22G2 Gold Ocean Front

    Bay Villa 22G2 Gold Ocean Front

    Kapalua, HI

    Perfectly situated above the waves in the most pristine and highly desired locations in Kapalua! This unique floor plan is the only ground-floor Kapalua Bay villas that can boast an additional 150+ square feet of living space facing the ocean!!...

    Pool

    $813 to $1,219/night

  4. VILLA
    Kapalua Golf Villa 25V2 Gold Ocean View

    Kapalua Golf Villa 25V2 Gold Ocean View

    Kapalua, HI

    If you enjoy the serene and tranquil feel of the Golf Villas but want a nice ocean view, you will be delighted with this little gem. It is the best of both worlds. Just steps from the pool and green or a short walk to the beach. This lovely villa is...

    Pool

    $281 to $494/night

  5. VILLA
    Bay Villa 22G4 Gold Ocean Front

    Bay Villa 22G4 Gold Ocean Front

    Kapalua, HI

    Dreaming of Paradise? You'll pinch yourself when you walk into this gorgeous Bay Villa. It's everything you imagined and more, including discounts on tee times at the world-famous Plantation and Bay Courses. Start your vacation with a frosty...

    Pool

    $563 to $781/night

  6. VILLA
    Kapalua Bay Villa 21B2

    Kapalua Bay Villa 21B2

    Kapalua, HI

    This gorgeous Beach Front Villa occupies the top two floors of building 21. It has two completely private master bedrooms with en-suite. Main floor master has a private lanai. Both master suites have spectacular ocean views. There are 3 bathrooms;...

    Pool

    $1,156 to $1,750/night

  7. VILLA
    Ridge 1721 Gold Ocean View

    Ridge 1721 Gold Ocean View

    Kapalua, HI

    This Kapalua Ridge Villa is located on top of the ridge near World Class Kapalua Beach. It offers it's visitors a panoramic view of the Pacific Ocean. Tropical breezes keep this scenic location pleasant and comfortable even on the warmest Maui...

    Pool

    $294 to $494/night

  8. VILLA
    Bay Villa 35B3 Gold Ocean Front

    Bay Villa 35B3 Gold Ocean Front

    Lahaina, HI

    The spacious interior of this 2 bed 3 bath tranquil retreat is the perfect blend of premium comfort and contemporary modern design. Stately and well-appointed, this lovely villa is uniquely positioned for endless views of the Pacific and neighboring...

    Pool

    $781 to $1,219/night

  9. VILLA
    Kapalua Golf Villa Gold Panoramic View 23V3

    Kapalua Golf Villa Gold Panoramic View 23V3

    Kapalua, HI

    Pamper yourself in this gorgeous penthouse villa. Amazing sunsets and panoramic ocean views with the islands of Molokai and Lanai as a back drop will take your breath away! A portion of the lanai has been enclosed to enhance and expand your living...

    Pool

    $369 to $688/night

  10. VILLA
    Bay Villa 12g5 Ocean View

    Bay Villa 12g5 Ocean View

    Kapalua, HI

    Your own little slice of paradise.. Wake up each morning to breath taking views of the Pacific as you take in the gentle sounds of the sea from your beautiful and spacious master suite with a new king size bed. This lovely villa has air...

    Pool

    $281 to $494/night

  11. VILLA
    Bay Villa 31G4 Gold Ocean View

    Bay Villa 31G4 Gold Ocean View

    Kapalua, HI

    This luxurious Island Villa is uniquely positioned to offer nice ocean views! The perfect Rx for leaving your every care behind. Surround yourself with rare exotic wood cabinetry, new granite counter tops and new stainless steel appliances, Cool...

    Pool

    $531 to $969/night

  12. CONDOMINIUM
    Kaleialoha #207

    Kaleialoha #207

    Lahaina, HI

    Completely remodeled condo. Two 55' Flat Screen TV's, A/C, Bosch washer Dryer, wine cooler. Granite and marble throughout. King bed. Free internet/ basic cable, onsite parking and local phone. Near Shopping, Restaurants and all beach activities....

    Pool
    FREE CANCELLATION

    $218 to $348/night

  13. CONDOMINIUM
    O-704 Hale Lau Wai Ko Olina Beach Villa

    O-704 Hale Lau Wai Ko Olina Beach Villa

    Kapolei, HI

    Enjoy direct ocean-facing views and beautiful garden and pool area views from this luxury Beach Villa at Ko'Olina. This well-appointed 1,171 square foot 2 bedroom 2 bathroom 7th floor Beach Villa has direct ocean views overlooking the lap pool and...

    Pool

    $392 to $1,204/night

  14. CONDOMINIUM
    Hale Kamaole #129

    Hale Kamaole #129

    Kihei, HI

    Welcome to suite 129. This beautifully appointed one bedroom, one bath ground floor unit has brand new hardwood floors in the bedroom and living room, and ceramic tile throughout the rest of the condo. It features new bedroom furniture including a...

    Pool
    FREE CANCELLATION

    $214 to $312/night

  15. HOUSE
    Junior Suite Oceanfront #1006

    Junior Suite Oceanfront #1006

    Lahaina, HI

    {Jr. Suite (Studio) - King bed; Flat screen TV; extended lanai} MAUI KAI 1006 This oceanfront junior suite is a bright, airy unit decorated in light tones, pale off-white tile in the kitchen and bath, with carpet in the center living area of the...

    Pool Hot Tub
    FREE CANCELLATION

    $278 to $341/night

  16. VILLA
    Golf Villa 25T4

    Golf Villa 25T4

    Kapalua, HI

    This lovely Villa has the feeling of casual island elegance with it's open style kitchen and living-dining area. Featuring a luxury gourmet kitchen with quality stainless steel appliances, surrounded by natural stone and warm exotic woods. It will...

    Pool

    $294 to $563/night

  17. CONDOMINIUM
    Kaleialoha #115

    Kaleialoha #115

    Lahaina, HI

    Lovely corner unit with all one side louvered windows to let the outside in! Recently upgraded with gorgeous granite counter, all new appliances and tile through out! Unit has unique four poster bed, walk in tiled shower, AC in living area, in suite...

    Pool
    FREE CANCELLATION

    $207 to $336/night

  18. CONDOMINIUM
    Puu Poa 102

    Puu Poa 102

    Princeville, HI

    Pu’u Po’a 102 is located on the bluff of Princeville with spectacular ocean views. There are 2 tastefully decorated bedrooms and 2 bathrooms. Two private lanais for relaxing, dining, and barbequing. A large flat screen TV/DVD with a movie...

    Pool

    $362 to $512/night

  19. CONDOMINIUM
    Grand Champions #143

    Grand Champions #143

    Wailea, HI

    Unit 143 at the Wailea Grand Champions is a rare 3 bedroom 2 bath unit with magnificent golf course views. It has been recently renovated with all new furnishings. It has a fully equipped kitchen, washer and dryer, room AC in each room as well as...

    Pool Hot Tub
    FREE CANCELLATION

    $458 to $748/night

  20. CONDOMINIUM
    Wailea Ekolu #310

    Wailea Ekolu #310

    Kihei, HI

    Wailea Ekolu has several lovely pool areas as well as a large pavilion area for larger groups. There are also additional barbecue and picnic areas on the grounds with panoramic views of the ocean and the sunsets. The beautiful Mokapu and Ulua...

    Pool
    FREE CANCELLATION

    $302 to $534/night

  21. CONDOMINIUM
    Wailea Ekolu #103

    Wailea Ekolu #103

    Wailea, HI

    Wailea Ekolu has several lovely pool areas as well as a large pavilion area for larger groups. There are also additional barbecue and picnic areas on the grounds with panoramic views of the ocean and the sunsets. The beautiful Mokapu and Ulua...

    Pool
    FREE CANCELLATION

    $240 to $521/night

  22. CONDOMINIUM
    Maui Kamaole #D-107

    Maui Kamaole #D-107

    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

    $174 to $238/night

  23. CONDOMINIUM
    Waiohuli Beach Hale #C-210

    Waiohuli Beach Hale #C-210

    Kihei, HI

    Waiohuli Beach Hale is a small oceanfront complex located in Kihei Maui Hawaii. This property has a great aloha feeling with a relaxed and quiet atmosphere. Each unit is steps from the ocean and is centrally located to great shopping, restaurants,...

    Pool
    FREE CANCELLATION

    $208 to $347/night

  24. CONDOMINIUM
    Hale Kamaole #311

    Hale Kamaole #311

    Kihei, HI

    This two bedroom condo without a loft, has a good Ocean and Garden View. Master bedroom has king bed. Down stairs bedroom has king bed. Hide a bed couch in the living room. Spacious kitchen cabinets. Wood and tile floor including lanai no carpet....

    Pool
    FREE CANCELLATION

    $245 to $355/night

  25. HOUSE
    1 Bedroom Corner Oceanfront #908

    1 Bedroom Corner Oceanfront #908

    Kaanapali, HI

    This beautiful One Bedroom Corner unit was recently renovated and has a breathtaking view! Featuring a King Bed, Queen Sofa Sleeper, full kitchen, all done in the warm island style. Wake up and have breakfast on your spacious open lanai while you...

    Pool Hot Tub
    FREE CANCELLATION

    $372 to $444/night

  26. CONDOMINIUM
    Hale Kamaole #217

    Hale Kamaole #217

    Kihei, HI

    Great Garden and Ocean view. New living room furniture, two lazy boy chairs along with queen hide-a-bed. King bed bought in 2013 in bedroom with rattan furniture. Nice, spacious, updated kitchen and appliances. 42 inch flat screen TV, safe in unit...

    Pool
    FREE CANCELLATION

    $196 to $281/night

  27. CONDOMINIUM
    Kanaloa 202 (2-Bedroom Condo)

    Kanaloa 202 (2-Bedroom Condo)

    Keauhou, HI

    Historic and Charming Keauhou Bay is just steps away from Kanaloa at Kona. The premier resort in Keauhou Resort area. The location is perfect. Close to supermarket, restaurants, shopping, golf, beaches, sport fishing, and other vacation activities....

    Pool

    $169 to $230/night

  28. CONDOMINIUM
    Kulakane 304

    Kulakane 304

    Lahaina, HI

    The Kulakane is the most distinctive condominium building on the beautiful West Maui shore. Picturesque views of neighboring islands and spectacular sunsets. Watch the whales, dolphins and sea turtles up close while relaxing at our oceanside pool or...

    Pool
    FREE CANCELLATION

    $261 to $925/night

  29. CONDOMINIUM
    Kaleialoha 211

    Kaleialoha 211

    Lahaina, HI

    This beautiful 1 bedroom, 1 bathroom oceanfront condominium provides everything you need for your vacation in paradise. With spectacular panoramic views over Maui’s neighbor islands, Lanai and Molokai, you can’t beat watching the whales and...

    Pool
    FREE CANCELLATION

    $174 to $340/night

  30. CONDOMINIUM
    Mahana 1113

    Mahana 1113

    Lahaina, HI

    Mahana 1113 New Studio Listing! Breathtaking Oceanfront Views Greet you! Sleeps 2. When you first open the door to your eleventh-floor unit, you are facing a wall of windows in your studio showcasing the panorama of the endless waves, spectacular...

    Pool Hot Tub
    FREE CANCELLATION

    $206 to $844/night