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
    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 a fully equipped kitchen, washer and dryer, room air conditioning in each room as well as ceiling fans throughout.Same day bookings...

    Pool Hot Tub
    FREE CANCELLATION

    $458 to $748/night

  2. CONDOMINIUM
    Maui Banyan #G-406

    Maui Banyan #G-406

    Kihei, HI

    Remodeled Ocean view condo at the Maui Banyan in South Kihei. This one bedroom condo is the perfect Maui retreat! This condo has been completely remodeled. The kitchen features stainless appliances, bamboo cabinets and a stylish counter top. Both...

    Pool Hot Tub
    FREE CANCELLATION

    $312 to $374/night

  3. CONDOMINIUM
    Kamaole Sands #06-405

    Kamaole Sands #06-405

    KIHEI, HI

    You will not be disappointed! This well-appointed two bedroom garden view condo has been remodeled and has new furnishings throughout. The main floor bedroom has two twin beds and there is a full bath located just outside the bedroom. The loft...

    Pool Hot Tub
    FREE CANCELLATION

    $391 to $482/night

  4. CONDOMINIUM
    Kona Reef D32

    Kona Reef D32

    Kailua Kona, HI

    Private, top floor, absolute oceanfront, lovely one bedroom condo at the highly acclaimed Kona Reef Resort!Why Kona Reef:• Conveniently located along the prestigious Alii Drive in the heart of Kona town.• It’s a 5 minute walk in your...

    Pool Hot Tub
    FREE CANCELLATION

    $161 to $292/night

  5. CONDOMINIUM
    Hale Ono Loa 401

    Hale Ono Loa 401

    Lahaina, HI

    Look straight out from condo and large lanai directly at WHALES, SEA TURTLES, MOLOKAI & LANAI! Close to everything in West Maui! Close to Whalers and downtown Lahaina. HUGE OCEANFRONT condo complex with beautifully tiled pool, large grounds, WORLD...

    Pool
    FREE CANCELLATION

    $144 to $274/night

  6. CONDOMINIUM
    Maui Parkshore #312

    Maui Parkshore #312

    KIHEI, HI

    *The Pool at the Maui Parkshore will be CLOSED September 3 - 25, 2019* Enjoy Ocean views from this two bedroom two bathroom condo. The master bedroom has a queen bed and a full bathroom ensuite. The second bedroom has two twin beds and the living...

    Pool
    FREE CANCELLATION

    $314 to $369/night

  7. 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

    $1,518 to $2,364/night

  8. CONDOMINIUM
    Kauhale Makai #132

    Kauhale Makai #132

    KIHEI, HI

    PLEASE NOTE: Kauhale Makai is undergoing exterior building maintenance. Completely Renovated and remodeled into the perfect modern beach style condo. Completed in May 2016, this trendy beach haven is the perfect getaway. Enojy Ocean Views from this...

    Pool Hot Tub
    FREE CANCELLATION

    $321 to $411/night

  9. CONDOMINIUM
    Maui Banyan #H-502

    Maui Banyan #H-502

    Kihei, HI

    This condo has a 40% discount already applied to the rate and will not accept additional promotions. Every detail is perfection in this completely remodeled one bedroom condo at the Maui Banyan in South Kihei. You will be in awe of the top of...

    Pool Hot Tub
    FREE CANCELLATION

    $187 to $374/night

  10. CONDOMINIUM
    Maui Parkshore #306

    Maui Parkshore #306

    KIHEI, HI

    *The Pool at the Maui Parkshore will be CLOSED September 3 - 25, 2019* Completely remodeled two bedroom, partial ocean view condo at the Maui Parkshore. From a new kitchen and bathrooms to new furnishings, new flooring and painted walls, this condo...

    Pool
    FREE CANCELLATION

    $314 to $369/night

  11. CONDOMINIUM
    Kihei Surfside #412

    Kihei Surfside #412

    KIHEI, HI

    Completely remodeled condo, from top to bottom. Nothing has been overlooked in this beautifully appointed one bedroom Ocean Front condo. This stunning renovation, features top of the line materials including granite counter tops in kitchen and...

    Pool
    FREE CANCELLATION

    $363 to $485/night

  12. CONDOMINIUM
    Maui Kamaole #f-208

    Maui Kamaole #f-208

    KIHEI, HI

    There are two (2) bedrooms and two (2) bathrooms in this Garden View Condo. This unit sleeps up to 6 people with a King bed in the loft Master bedroom, a queen bed in the second bedroom and a pull out sofa bed in the living room. The kitchen is...

    Pool Hot Tub
    FREE CANCELLATION

    $404 to $514/night

  13. HOUSE
    Koa Kai Hale

    Koa Kai Hale

    Princeville, HI

    The ultimate Kauai vacation home, Koa Kai Hale has large windows in every room that surround you with lush north shore views. With 3,300 square feet of living space, this home has plenty of room for everyone to relax into their Hawaiian getaway.Koa...

    $601 to $1,227/night

  14. COTTAGE
    Mauna Lani KaMilo Home (424)

    Mauna Lani KaMilo Home (424)

    Kamuela, HI

    This spectacular 3 bedroom- 3 bath single-level cottage is located within Kamilo, which is nestled near the heart of the Mauna Lani Resort area. Upon entering Mauna Lani KaMilo Home (424) enjoy the vaulted ceilings and open floor plan which allows...

    Pool Hot Tub

    $481 to $1,285/night

  15. HOUSE
    7 C's Kona (Big Island)

    7 C's Kona (Big Island)

    Kailua Kona, HI

    ***Please note there is a 7 night minimum during the holidays. Christmas reservations must check out by 10AM on Dec. 27 and New Year's reservations can check in on Dec. 27 or after for a week. There is a 14 night minimum to book both Christmas and...

    Pool

    $482 to $720/night

  16. BUNGALOW
    He'eia Bay Beach Bungalow (Big Island)

    He'eia Bay Beach Bungalow (Big Island)

    Kailua Kona, HI

    Located in a very desirable neighborhood, the Keauhou subdivision, this beautifully remodeled home sits right on the Kona Country Club Golf Course and offers exceptional golf course views! This home is surrounded by beauty and is directly across...

    $411 to $720/night

  17. CONDOMINIUM
    Kona Isle B31

    Kona Isle B31

    Kailua Kona, HI

    B31 at the Kona Isle is an amazing top floor condo in building B at the Kona Isle.Comfortable Queen Sized bed, and pull out sofa that can sleep 2! Comfortably sleep 4 in the property.Being on the top floor gives you a beautiful view of the grounds....

    Pool
    FREE CANCELLATION

    $152 to $280/night

  18. TOWNHOUSE
    Pili Mai 11I

    Pili Mai 11I

    Koloa, HI

    Enjoy modern Hawaii living at Pili Mai 11IPack your golf clubs and get ready to enjoy modern Hawaii living in this exclusive Poipu community. Located on the 9th hole of the beautiful Kiahuna Golf Course, this exceptionally beautiful,...

    Pool Hot Tub

    $476 to $1,214/night

  19. CONDOMINIUM
    Kihei Akahi #C-608

    Kihei Akahi #C-608

    KIHEI, HI

    This one bedroom garden view condo has many upgrades throughout featuring new living room furnishings, new dinning table, large flat screen TV in the living room and tile floors. This one bedroom condo sleeps up to four people with a king bed in the...

    Pool
    FREE CANCELLATION

    $248 to $312/night

  20. CONDOMINIUM
    Royal Kahana 702

    Royal Kahana 702

    Lahaina, HI

    Aloha from paradise! We are excited to offer our beautiful 7th floor studio suite at this popular West Maui resort! The condo has all of the amenities you would want on a tropical vacation (including AC and a washer and dryer in the unit)! The...

    Pool
    FREE CANCELLATION

    $191 to $346/night

  21. CONDOMINIUM
    Kamaole Sands #5-414

    Kamaole Sands #5-414

    Kihei, HI

    Unit 5-414 is a breathtakingly beautiful penthouse suite with a gorgeous ocean view! Our condo is located in the desirable building #5 in the heart of the richly manicured tropical oasis of Kamaole Sands located across from Kamaole Beach Park III --...

    Pool Hot Tub
    FREE CANCELLATION

    $273 to $429/night

  22. HOUSE
    Mana Alana at Poipu

    Mana Alana at Poipu

    Koloa, HI

    This stunning Poipu home boasts over 3,300 square feet of elegant living space, along with sweeping views from the coastline up the sloping hills of Kalaheo. An open floor plan provides guests with the perfect setting for quality time together,...

    Pool Hot Tub

    $899 to $2,487/night

  23. HOUSE
    Ono Oasis

    Ono Oasis

    Kailua Kona, HI

    True to its name, Ono Oasis offers a unique tropical retreat for a dream Big Island vacation, with distant ocean and sunset views, a heated saltwater pool, and over 2,800 square feet of luxury living space. This extraordinary home provides the...

    Pool

    $512 to $957/night

  24. HOUSE
    Leilani Kai Hale

    Leilani Kai Hale

    Princeville, HI

    Panoramic mountain views and tropical vegetation surround you in this beautifully updated Princeville luxury home with air conditioning and its own saltwater pool and spa. Complete with stylish furnishings and fine finishes such as granite counter...

    Pool Hot Tub

    $595 to $1,227/night

  25. CONDOMINIUM
    Kamaole Sands #03-407

    Kamaole Sands #03-407

    KIHEI, HI

    Large two bedroom loft, Garden view Condo. Feel right at home in this spacious condo overlooking the pool and beautifully manicured green way. There is a King bed in the loft bedroom, two twins in the second bedroom, and a sofa bed in the living...

    Pool Hot Tub
    FREE CANCELLATION

    $391 to $482/night

  26. CONDOMINIUM
    Kaleialoha 112

    Kaleialoha 112

    Lahaina, HI

    Enjoy the white sand beach and beautiful tiled pool while you step out of your large ground floor lanai to a gorgeous lawn and lounge area right on the ocean. Five steps to SWIMMING, SNORKELING, SURFING on the PRIVATE white sand beach! See whales...

    Pool
    FREE CANCELLATION

    $167 to $324/night

  27. 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

    $150 to $254/night

  28. CONDOMINIUM
    Lower Honoapiilani Condo 2 Bedrooms Sleeps 6

    Lower Honoapiilani Condo 2 Bedrooms Sleeps 6

    Lahaina, HI

    Here at Serenity By the Sea all of your senses will be delighted…starting with the picturesque ocean/sunset views from the living room, kitchen & both bedrooms… to the music of the sound of the waves… to the smell of the fresh ocean air…. to...

    Pool
    FREE CANCELLATION

    $330 to $379/night

  29. CONDOMINIUM
    Kona Makai 1-301

    Kona Makai 1-301

    Kailua Kona, HI

    Kona Makai #1-301 is arguably the BEST condo in the entire complex! Being the top floor corner in building 1, the location is undeniably too perfect. Private & upgraded, this is direct oceanfront condo living at its finest. You can't get a better...

    Pool Hot Tub
    FREE CANCELLATION

    $625 to $674/night

  30. CONDOMINIUM
    Maui Kamaole #i-111

    Maui Kamaole #i-111

    KIHEI, HI

    Ground floor condo with one (1) bedroom and two (2) bathrooms. There is a king bed in the bedroom and a full bathroom ensuite and a pull out sofa bed in the living room, which allows this condo to accommodate up to four (4) people. The kitchen...

    Pool Hot Tub
    FREE CANCELLATION

    $313 to $411/night