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
    Sea Village 3-317

    Sea Village 3-317

    Kailua Kona, HI

    Sea Village#3-317 is an Amazing Vacation Rental Property. Sitting Directly on top of the water. You can't get closer to the water than this. Phenomenal Price For The Value. Sea Village Resort reflects the tranquil beauty of the Big Island. The...

    Pool Hot Tub
    FREE CANCELLATION
  2. CONDOMINIUM
    Keauhou Kona Surf & Racquet Club 2103

    Keauhou Kona Surf & Racquet Club 2103

    Kailua Kona, HI

    Welcome to Paradise. You found the perfect condo for your Hawaiian Vacation. 2-103 at the Surf & Racquet Club is a gorgeous, 2 bedroom, 2 bath DIRECT oceanfront ground floor property. This property has EVERYTHING you'll need. Wifi, Tennis Racquets,...

    Pool
    FREE CANCELLATION
  3. CONDOMINIUM
    Maui Banyan #G-201

    Maui Banyan #G-201

    Kihei, HI

    The Elevator for G & H building will be closed for Elevator Modernization starting at 10:00 am Monday September 10, 2018. We will have a bellman to help with luggages. Location, Location, Location!! Beautifully remodeled two bedroom Ocean View...

    Pool Hot Tub
    FREE CANCELLATION

    $411 to $514/night

  4. TOWNHOUSE
    Keauhou Kona Surf & Racket Club Townhouse #3

    Keauhou Kona Surf & Racket Club Townhouse #3

    Kailua Kona, HI

    This oceanfront townhouse is beautifullly furnished, very clean, and cozy. It has Wifi, HD Television & DVR. Have a bigger group? We manage Townhome#4 right next door. This property sleeps 4, and next door sleeps 6. A great option for 10 to be right...

    Pool
    FREE CANCELLATION
  5. CONDOMINIUM
    Kona Plaza 217

    Kona Plaza 217

    Kailua Kona, HI

    Welcome to the listing page of Kona Plaza#217. Brand new Vacation Rental as of January 2019. It's amazing location puts you right in immediate walking distance to restaurants, beaches, shopping & entertainment right in the heart of Kailua Village....

    Pool
    FREE CANCELLATION
  6. CONDOMINIUM
    Waipouli Beach Resort H403

    Waipouli Beach Resort H403

    Kapaa, HI

    Resort Living at its Best in this Penthouse Ultimate Luxury Condo Waipouli Beach Resort Oceanfront H403 an Exceptional Oceanfront 2 bedroom 3 bath condo at the beautiful Waipouli Beach Resort & Spa on the island of Kauai awarded Trip Advisor...

    Pool
    FREE CANCELLATION

    $408 to $765/night

  7. CONDOMINIUM
    760 South Kihei Condo Unit 414

    760 South Kihei Condo Unit 414

    Kihei, HI

    Feel Pacific breezes as you unwind on the lanai of your fourth-floor 3BR/2BA condo. This unit commands the most sought-after location in the building (front and center), closest to the ocean and furthest from the road. Take in stunning wide-open...

    Pool
    FREE CANCELLATION

    $408 to $755/night

  8. CONDOMINIUM
    Paki Maui Unit #421 Condo

    Paki Maui Unit #421 Condo

    Lahaina, HI

    Your Million Dollar Direct Ocean Front Views awaits you! 2 bedroom, 2 baths, sleeps 6. Enjoy breath taking panoramic views from 2 separate Lanais in our epic Oceanfront top floor home. This 1,150 sq ft unit has been fully remodeled & upgraded. All...

    Pool
    FREE CANCELLATION

    $406 to $566/night

  9. CONDOMINIUM
    Papakea Condo Unit D402

    Papakea Condo Unit D402

    Kaanapali, HI

    Ocean views in North Ka'anapali. This 4th floor condo features 2 bedrooms with bathrooms downstairs plus a loft bedroom, with 2 twins beds, and a half bathroom. The living room has a 37" LCD HDTV & Blu-ray player with property HD signal to match....

    Pool
    FREE CANCELLATION

    $406 to $986/night

  10. CONDOMINIUM
    Honua Kai Hokulani 306

    Honua Kai Hokulani 306

    Kaanapali, HI

    UPGRADED OCEAN/MOUNTAIN VIEW 2 bed/2 bath - GREAT VALUE! *This condo is so close to the beach you can hear the waves crashing! This 1240 sq ft OCEAN VIEW condo has been upgraded with new DESIGNER FURNISHINGS, SMART TV and TRAVERTINE FLOORING...

    Pool Hot Tub

    $406 to $1,455/night

  11. CONDOMINIUM
    Maui Kamaole b-204

    Maui Kamaole b-204

    KIHEI, HI

    Beautifully remodeled Two bedroom and two baths Garden View Condo. This Condo sleeps up to six (6) people with a King bed in the main floor bedroom and a Queen bed and twin daybed in the loft bedroom, as well as a pull out sofa bed in the living...

    Pool
    FREE CANCELLATION

    $404 to $514/night

  12. CONDOMINIUM
    Maui Kamaole #h-207

    Maui Kamaole #h-207

    Kihei, HI

    Enjoy your piece of paradise from this two bedroom, garden view, condo at the Maui Kamaole. This two bedroom, two bathroom, condo sleeps up to six people. There is a loft bedroom with a full en-suite and a sitting area. The second bedroom is on the...

    Pool
    FREE CANCELLATION

    $404 to $514/night

  13. CONDOMINIUM
    Maui Kamaole h-202

    Maui Kamaole h-202

    KIHEI, HI

    Renovated in 2018! This beautiful two bedroom condo at the Maui Kamaole has just been renovated featuring a new, top-of-the-line kitchen. This condo offers Partial Ocean views at garden view prices! Beautiful bathroom renovation summer, 2014. This...

    Pool
    FREE CANCELLATION

    $404 to $514/night

  14. CONDOMINIUM
    O-404: Hale Hauoli Ko Olina Beach Villa

    O-404: Hale Hauoli Ko Olina Beach Villa

    Kapolei, HI

    Experience the ultimate in oceanfront resort living in this beautiful and spacious vacation home located in the Beach Villas at Ko Olina! Overview: This 2 BR, 2 BA luxury villa on the 4th floor of the Beach Tower is conveniently located just 20...

    Pool Hot Tub

    $404 to $1,204/night

  15. CONDOMINIUM
    Kapalua Golf VIlla 14p7&8

    Kapalua Golf VIlla 14p7&8

    Lahaina, HI

    our home away from home is perfectly situated on the Kapalua Golf Villa resort property. Expansive golf views with Molokai drawing your eyes straight out over the Pacific and across the fairways of the Bay Golf Course. Some of the best views from...

    Pool
    FREE CANCELLATION

    $403 to $1,368/night

  16. COTTAGE
    22 Puako Beach Drive Cottage

    22 Puako Beach Drive Cottage

    Kamuela, HI

    Immerse yourself in island life at this unique 1BR oceanfront cottage. Surrounded by lush coconut palms, your rental provides unparalleled access to the turquoise water of Puako Bay and incredible ocean views from the bedroom and living area. Spend...

    FREE CANCELLATION

    $403 to $1,196/night

  17. CONDOMINIUM
    Poipu Shores B202

    Poipu Shores B202

    Koloa, HI

    This second floor 2br/1ba condo has two king beds, with air-conditioning in each bedroom and in the living room. Poipu Shores B202 has a full kitchen, updated with elegant granite counters, and one bathroom, recently remodeled. Enjoy a private...

    Pool
    FREE CANCELLATION

    $402 to $1,141/night

  18. CONDOMINIUM
    Kamaole Sands 10-407

    Kamaole Sands 10-407

    Kihei, HI

    Beautiful views of the Ocean, West Maui Mountains and the lush garden landscape await you at this top floor tastefully decorated two bedroom condo. The bedroom on the main floor has two twin beds and the loft bedroom serves as the master with a...

    Pool
    FREE CANCELLATION

    $402 to $506/night

  19. CONDOMINIUM
    Kamaole Sands 10-410

    Kamaole Sands 10-410

    KIHEI, HI

    Enjoy ocean views from this fourth floor, two bedroom condo. This unit sleeps up to six (6) people with a King Bed with a Simmons Beauty Rest mattress in the master bedroom loft, two twins that can convert into a King in the second bedroom and a...

    Pool
    FREE CANCELLATION

    $402 to $506/night

  20. CONDOMINIUM
    Kamaole Sands 08-411

    Kamaole Sands 08-411

    KIHEI, HI

    Beautiful Ocean View Unit in Building 8! With recent updates and renovations to the fully equipped kitchen, this unit is our ideal vacation rental condo. The unit allows for 6 guests with a King bed in the upstairs loft, 2 twins in the main level...

    Pool
    FREE CANCELLATION

    $402 to $506/night

  21. CONDOMINIUM
    Puu Poa 309

    Puu Poa 309

    Princeville, HI

    Puu Poa 309 offers 1800 Square feet of living space, two huge lanais, 2 bedrooms, 2 baths. All marble and glass-block master bath with dual shower heads and jacuzzi tub. Solid Teak Furniture, Beautiful Tile Floors throughout, Classic Plantation...

    Pool
    FREE CANCELLATION

    $402 to $998/night

  22. CONDOMINIUM
    Kamaole Sands 10-404

    Kamaole Sands 10-404

    KIHEI, HI

    Your Piece of Paradise at Kamaole Sands in South Kihei. This two Bedroom, 2 bath, Renovated Ocean view condominium is conveniently located at the front of the property and is a short walk across the street to the Kamaole Beach 3. The condo has two...

    Pool
    FREE CANCELLATION

    $402 to $506/night

  23. CONDOMINIUM
    Kamaole Sands 10-405

    Kamaole Sands 10-405

    KIHEI, HI

    Large Two bedroom Ocean view Loft. This two bedroom, two baths condo has a Queen Bed in Master bedroom (main level), two twins in second bedroom (upstairs in loft), and a pull out sofa bed in the living room, allowing this unit to sleep up to six...

    Pool
    FREE CANCELLATION

    $402 to $506/night

  24. TOWNHOUSE
    Kulalani at Mauna Lani 405

    Kulalani at Mauna Lani 405

    Kamuela, HI

    Welcome to our beautifully appointed town home at Kulalani, located at the prestigious Mauna Lani Resort on the Big Island of Hawaii. Kulalani is one of the newest developments in Mauna Lani and boasts the largest and best pools and workout center...

    Pool

    $401 to $731/night

  25. VILLA
    Bay Villa 31B1 Ocean View

    Bay Villa 31B1 Ocean View

    Kapalua, HI

    This Bay Villa boasts amazing ocean views and it gives you a feeling of being perched above the landscape and ocean below. Come experience the warm breezes and true aloha spirit. For your comfort and convenience we include the following amenities:...

    Pool

    $400 to $563/night

  26. CONDOMINIUM
    Papakea L106

    Papakea L106

    Lahaina, HI

    Highly upgraded West Maui Kaanapali Papakea 2 bedroom, 2 full bathrooms, ground floor condo 25 feet from the oceans edge. Watch the whales, sunsets, and the ocean from the kitchen, living room and lanai. Sleep to the sound of the waves. This condo...

    Pool

    $400 to $491/night

  27. CONDOMINIUM
    Palms at Wailea #1102

    Palms at Wailea #1102

    Wailea, HI

    The fabulous Keawakapu Beach is just a short 10 minute stroll from the Palms at Wailea. This beach is world famous for its great snorkeling and long walking beach. The Palms at Wailea is a gorgeous property; lush with tropical landscaping. There is...

    Pool Hot Tub
    FREE CANCELLATION

    $400 to $580/night

  28. CONDOMINIUM
    Kona Makai 1-204

    Kona Makai 1-204

    Kailua Kona, HI

    This 2 bedroom 2 bath condo has everything you need to relax in paradise! Enjoy ocean views and gorgeous kona sunsets from your private lanai. The well appointed kitchen is fully equipped to comfortably prepare meals/drinks and the spacious living...

    Pool Hot Tub
    FREE CANCELLATION
  29. CONDOMINIUM
    Whaler at Kaanapali Beach 163

    Whaler at Kaanapali Beach 163

    Lahaina, HI

    Upgraded and Renovated studio garden view condo at the Whaler on Ka'anapali beach. This spacious studio can sleep up to two people. There is a King bed and a Full size sofa bed. Located on the ground floor and a short walk to the beach. There is a...

    Pool
    FREE CANCELLATION

    $397 to $591/night

  30. CONDOMINIUM
    Puu Poa 405

    Puu Poa 405

    Princeville, HI

    Puu Poa 405: This spacious top floor condo in the upscale Puu Poa complex on the north shore of beautiful Kauai is located directly next door to the Princeville St Regis Hotel. You'll love the newly renovated oceanfront pool! Also available onsite...

    Pool
    FREE CANCELLATION

    $397 to $458/night