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
    Kahana Sunset E 11

    Kahana Sunset E 11

    Lahaina, HI

    The Kahana Sunset Welcomes you with This unique condo is a beachfront property on the world famous West Coast of Maui between Kaanapali and Kapalua. Included in our fabulous price are many owner-supplied extras such as: • Beach chairs (2) •...

    Pool
    FREE CANCELLATION

    $251 to $389/night

  2. CONDOMINIUM
    Hale Pineapple

    Hale Pineapple

    Lahaina, HI

    Welcome to Hau'oli Hala Kahiki, a hidden gem in Honokowai on Maui's beautiful west shore. Located in the quiet, low-density Kaleialoha building, this sweet 1 bedroom/1 bath condo sits on the ground floor, so no stairs to climb or having to wait for...

    FREE CANCELLATION

    $181 to $239/night

  3. CONDOMINIUM
    Honua Kai Konea 215

    Honua Kai Konea 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

    $275 to $413/night

  4. CONDOMINIUM
    Diamond Head Beach Hotel 1401

    Diamond Head Beach Hotel 1401

    Honolulu, HI

    Oceanfront - Spacious 1 Bd Penthouse With Large Living Area And Full Kitchen. Rooftop Penthouse - Sitting above the Pacific Ocean and nestled under Hawaii's iconic Diamond Head crater. Beautifully furnished with a light and airy ocean theme, this...

    FREE CANCELLATION

    $360 to $557/night

  5. CONDOMINIUM
    Honua kai 437

    Honua kai 437

    Lahaina, HI

    HONUA KAI RESORT AND SPA SUITE 437 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

    $263 to $413/night

  6. CONDOMINIUM
    Hale Maluhia Ko Olina Beach Villa (O425)

    Hale Maluhia Ko Olina Beach Villa (O425)

    Kapolei, HI

    LIVE CALENDAR If the calendar shows as available, the property is not reserved and can be booked instantly online. This listing is updated in real-time. Please click the calendar tab to see availability. This Villa requires a minimum 6 night stay....

    Pool Hot Tub

    $485 to $1,204/night

  7. CONDOMINIUM
    Wailea Ekahi Unit #22D

    Wailea Ekahi Unit #22D

    Wailea, HI

    Wailea Ekahi Village is a beautifully terraced property located at the entrance to the resort community of Wailea. This relaxing low-density property consists of 54 two-story buildings spread out over thirty-four acres of immaculate tropical...

    Pool

    $336 to $432/night

  8. CONDOMINIUM
    Makena Surf Resort, #C-102

    Makena Surf Resort, #C-102

    Makena, HI

    Makena Surf Resort is a luxurious secluded beachfront condominium located in exclusive Makena. This gated community was developed with six 2 & 3 story buildings each offering sweeping views of the Pacific. The pristine and picturesque beach and...

    Pool

    $538 to $926/night

  9. CONDOMINIUM
    Wailea Elua Unit #0202

    Wailea Elua Unit #0202

    Wailea, HI

    Wailea Elua Village is an exclusive beachfront property located in the heart of the resort community of Wailea. This relaxing low-density property consists of two-story buildings terraced over twenty-four acres of immaculate tropical landscaping....

    Pool

    $494 to $1,065/night

  10. CONDOMINIUM
    Makena Surf Resort, #G-101

    Makena Surf Resort, #G-101

    Makena, HI

    A note from the owner. Welcome to our Maui ohana. Our unit is special because of the extra space and privacy, including the cool, shady side lanai we call our grotto - the perfect place to curl up with a good book, and a lovely respite from the...

    Pool

    $775 to $1,094/night

  11. CONDOMINIUM
    Wailea Elua Unit #1309

    Wailea Elua Unit #1309

    Wailea, HI

    Our condo has been in our family for 25 years. The grandparents recognized the gorgeous views that Elua represented, snorkeling among the turtles, abundant sea life, great diving, fishing, and the opportunities to bike down the side of Mt....

    Pool

    $634 to $896/night

  12. CONDOMINIUM
    Wailea Grand Champion, #148

    Wailea Grand Champion, #148

    Wailea, HI

    Wailea Grand Champions Golf Villas is a modern property located between the Wailea Blue Golf Course and the Wailea Tennis Club. This quiet low density development consists of twenty mostly two-story buildings set amongst lush tropical landscaping...

    Pool Hot Tub

    $201 to $549/night

  13. CONDOMINIUM
    Wailea Elua Unit #807

    Wailea Elua Unit #807

    Wailea, HI

    Wailea Elua Village is an exclusive beachfront property located in the heart of the resort community of Wailea. This relaxing low-density property consists of two-story buildings terraced over twenty-four acres of immaculate tropical landscaping....

    Pool

    $329 to $528/night

  14. CONDOMINIUM
    Wailea Elua Unit #0106

    Wailea Elua Unit #0106

    Wailea, HI

    About this condo: Wailea Elua Village #106 is a second floor, two bedroom-two bath, ocean view condo with a large lanai complete with a sun shade screen. It has a king bed in the master bedroom and a queen bed in the guest bedroom. This unit can be...

    Pool

    $299 to $488/night

  15. CONDOMINIUM
    Wailea Elua Unit #1403

    Wailea Elua Unit #1403

    Wailea, HI

    Wailea Elua Village is an exclusive beachfront property located in the heart of the resort community of Wailea. This relaxing low-density property consists of two-story buildings terraced over twenty-four acres of immaculate tropical landscaping....

    Pool

    $931 to $1,459/night

  16. CONDOMINIUM
    Sugar Beach Resort, #524

    Sugar Beach Resort, #524

    Kihei, HI

    A note from the owner: Tropical bliss welcomes you from the moment you walk through the door and past the gorgeous island artwork hanging on the wall. As you step into the main living area of the condo, prepare yourself to see one of the most...

    Pool

    $190 to $387/night

  17. CONDOMINIUM
    Maui Sunset #A-407

    Maui Sunset #A-407

    Kihei, HI

    Maui Sunset is a fabulous oceanfront property in Kihei that has lush tropical landscaping, large pool which is heated during the winter months, hot tub, gas grills, work out room and tennis courts out on the beach for your use. Guests return here...

    Pool Hot Tub
    FREE CANCELLATION

    $126 to $219/night

  18. CONDOMINIUM
    Maui Sunset #A-509

    Maui Sunset #A-509

    Kihei, HI

    Maui Sunset – 1BR Oceanfront Condo with a Whale-Watching Lanai There’s a reason many of our lovely guests return year after year to our oceanfront Maui condo. Actually, there are lots of reasons. The condo community’s sparkling pool which...

    Pool Hot Tub
    FREE CANCELLATION

    $173 to $231/night

  19. CONDOMINIUM
    H3-1 Bedroom Beachfront

    H3-1 Bedroom Beachfront

    Kihei, HI

    Ma'alaea Surf, Unit H3 is a conveniently located ground floor condo, just steps from our large pool and Sugar beach. This condo features a full kitchen and dining table. The master bedroom has a king sized bed. The large living room has expansive...

    Pool
    FREE CANCELLATION

    $304 to $467/night

  20. CONDOMINIUM
    Maui Sunset #A-117

    Maui Sunset #A-117

    Kihei, HI

    Maui Sunset is a fabulous oceanfront property in Kihei that has lush tropical landscaping, large pool which is heated during the winter months, hot tub, gas grills, workout room, and tennis courts out on the beach for your use. Guests return here...

    Pool Hot Tub
    FREE CANCELLATION

    $144 to $231/night

  21. CONDOMINIUM
    Nohonani 405

    Nohonani 405

    Lahaina, HI

    Nohonani 405 is a beautiful two bedroom one and a half bath unit on the fourth floor, with vaulted ceilings and a breathtaking ocean view. Ocean views can be seen from the kitchen, dining areas, living room and master bedroom. As with all the...

    Pool
    FREE CANCELLATION

    $274 to $403/night

  22. HOUSE
    Hale Pua

    Hale Pua

    Kailua Kona, HI

    Hale Pua (“House of Flowers”) is one of the few 5 bedroom/6 full bath oceanfront vacation rental homes with its own private pool & spa in the Kailua-Kona area. For recent candid photos and input from guests, please visit our FB page,...

    Pool Hot Tub

    $1,938 to $2,627/night

  23. CONDOMINIUM
    Keauhou Kona Surf & Racquet Club #6-104

    Keauhou Kona Surf & Racquet Club #6-104

    Kailua Kona, HI

    **BRAND NEW PROPERTY IN OUR INVENTORY! AIR CONDITIONING INSTALLED AS OF SEPTEMBER 2018!** Unit#6-104 is a well-maintained 2BR/2BA ground floor unit in a 15-acre, gated oceanfront complex at the Keauhou Kona Surf & Racquet Club. It's also an end...

    Pool
    FREE CANCELLATION

    $292/night

  24. CONDOMINIUM
    Ilikai Marina Condo 1290

    Ilikai Marina Condo 1290

    Honolulu, HI

    If you are looking for a fully equipped unit with 180 degree of ocean and beautiful Hawaiian scenery, then your search is over and you have found your home away from home in paradise. The location cant be beat and the peaceful ambiance and tranquil...

    FREE CANCELLATION

    $168 to $309/night

  25. CONDOMINIUM
    Hoyochi Nikko #109

    Hoyochi Nikko #109

    Lahaina, HI

    One bedroom condo located in beautiful west Maui. For those wishing additional solitude, this is an end unit with a new queen bed and bedroom air conditioning. All units are fully equipped with Cable TV, DVD, CD player, washer/dryer, and...

    Pool
    FREE CANCELLATION

    $201 to $296/night

  26. CONDOMINIUM
    Kahana Villa F-410

    Kahana Villa F-410

    Lahaina, HI

    F-410 is the newest, most beautifully upgraded unit around - and the prices are FANTASTIC! There is literally nothing more you could ask for in a vacation rental condo. Everything is available to you. Upgraded kitchen, granite counter tops,...

    Pool Hot Tub
    FREE CANCELLATION

    $206/night

  27. CONDOMINIUM
    Kanai A Nalu 212

    Kanai A Nalu 212

    Maalaea, HI

    Kanai A Nalu #212 is registered as a Transient Accommodation. Owner Registration I.D. TA-097-282-8672-01 Right On The Beach And Only Steps To The Sand / New Kitchen Remodel! This 2 br/ba second floor condo beach retreat is located at the popular...

    Pool
    FREE CANCELLATION

    $287/night

  28. HOUSE
    Kauhale Pilialoha

    Kauhale Pilialoha

    Kamuela, HI

    Indulge yourself in the ultimate island style luxury at the Big Island of Hawaii’s most exclusive retreat, Kauhale Pilialoha. Experience breathtaking sunsets, enjoy the natural beauty of Hawaii from the ultimate poolside lanai perched on the...

    Pool Hot Tub

    $17,975 to $27,561/night

  29. CONDOMINIUM
    Sugar Beach Resort, #418

    Sugar Beach Resort, #418

    Kihei, HI

    Sugar Beach Resort is the Winner of Building of the Year and Manager of the Year Awards from the Institute of Real Estate Management (IREM®) Sugar Beach Resort is a tranquil beachfront condominium resort located in North Kihei offering sweeping...

    Pool

    $190 to $387/night

  30. 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