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
    Puamana 153-4

    Puamana 153-4

    Lahaina, HI

    Walk to the Beach and Downtown Lahaina. Puamana is the perfect setting for families, romantic getaways, or anniversary celebrations. Puamana is a gated 30 acre ocean front community of low rise high quality attached homes nestled along the sunny...

    Pool
    FREE CANCELLATION

    $503 to $1,616/night

  2. CONDOMINIUM
    Kaleialoha 210

    Kaleialoha 210

    Lahaina, HI

    Views of the gorgeous Pacific Ocean and the neighboring islands from your lanai. Watch sea turtles eat seaweed off of the coral right below the lanai as well as watch whales breach during the winter months. Being just 50ft from the from the ocean...

    Pool
    FREE CANCELLATION

    $186 to $754/night

  3. CONDOMINIUM
    Honua Kai Konea 705

    Honua Kai Konea 705

    Kaanapali, HI

    WOW! HUGE OCEAN VIEWS WITH SUNSETS ALL YEAR LONG!!! This spectacular 7th Floor OCEAN VIEW 2 bed2 bath home is one of the finest at the Honua Kai Resort & Spa. JUST UPGRADED WITH NEW DESIGNER FURNISHINGS AND PORCELAIN TILE FLOORING THROUGHOUT! The...

    Pool Hot Tub

    $429 to $1,685/night

  4. CONDOMINIUM
    Honua Kai Hokulani 709

    Honua Kai Hokulani 709

    Kaanapali, HI

    Never before offered for rental, Honua kai Hokulani 709 is clearly the best 2 bedroom condo available in the Hokulani Building. Top of the highly desirable "09" stack, it just doesn't get any better than this. The best Ocean views from INSIDE the...

    Pool Hot Tub

    $526 to $2,000/night

  5. CONDOMINIUM
    Kaanapali Shores 943

    Kaanapali Shores 943

    Kaanapali, HI

    This beautiful 717 sq ft condo is on the 9th Floor with no one above you! Enjoy Sweeping Ocean Vistas, Sunsets and Whales leaping in Winter! The large 104 sq ft Lanai is perfect for enjoying your morning coffee or an afternoon cocktail as the sun...

    Pool Hot Tub

    $220 to $752/night

  6. CONDOMINIUM
    Luana Garden Villa 3C

    Luana Garden Villa 3C

    Kaanapali, HI

    Luana Garden Villas is the newest offering at the beautiful Honua kai Resort & Spa.  These spacious 3 bedroom Villas are located in 3 private enclaves and include large lanai's, private outdoor kitchens and a private garage. Each Enclave boasts a...

    Pool Hot Tub

    $795 to $3,303/night

  7. CONDOMINIUM
    Honua Kai Konea 606

    Honua Kai Konea 606

    Kaanapali, HI

    NOTE: As of 2/6/18 construction of 72 Townhomes has commenced behind the Konea building at Honua kai. There may be noise and dust on work days during construction hours from 8am to 5pm. Konea 606 is a large 945 square foot (plus 180 sq ft Lanai)...

    Pool Hot Tub

    $293 to $1,211/night

  8. CONDOMINIUM
    Kihei Beach Unit #110

    Kihei Beach Unit #110

    Kihei, HI

    Kihei Beach is a moderately sized six story beachfront property located in North Kihei. It offers sweeping views of Kahoolawe, Molokini and the dazzling Pacific Ocean and a friendly casual atmosphere. Fronting the property is Sugar Beach, well known...

    Pool

    $263 to $421/night

  9. CONDOMINIUM
    Bamboo Waikiki #1103

    Bamboo Waikiki #1103

    Honolulu, HI

    Relaxing tropical retreat in the courtyard of the Bamboo Waikiki hotel. Rest your head at night on the King bed in this one bedroom condo. Just outside the bedroom is the living area which features a futon sofa bed and mini bar area. Options are...

    Pool
    FREE CANCELLATION

    $225 to $267/night

  10. CONDOMINIUM
    Waikiki Banyan Tower 1 Suite 1602

    Waikiki Banyan Tower 1 Suite 1602

    Honolulu, HI

    Newly upgraded condo just minutes from world famous Waikiki Beach! The kitchen includes standard kitchen wares and has a table that seats up to six people. There is also a fan in the living room for additional lighting and air flow. Enjoy views of...

    Pool Hot Tub

    $146 to $259/night

  11. CONDOMINIUM
    Kona Isle C28

    Kona Isle C28

    Kailua Kona, HI

    Kona Isle C-28 is a fantastic new addition to Knutson & Associates Property Management as of January 2019! We're proud to represent this wonderful second floor, corner end unit in highly desirable Building C at the Kona Isle! These second floor...

    Pool
    FREE CANCELLATION
  12. CONDOMINIUM
    Waikiki Banyan Tower 1 Suite 3710

    Waikiki Banyan Tower 1 Suite 3710

    Honolulu, HI

    Ocean View Condo Waikiki Banyan condo suite located only one block from world famous Waikiki Beach! Ocean and city views make this condo special. Sleeping arrangements include two queen-sized beds in the bedroom. 2 access door into the bathroom...

    Pool Hot Tub

    $146 to $236/night

  13. CONDOMINIUM
    Kihei Alii Kai #A-305

    Kihei Alii Kai #A-305

    Kihei, HI

    The Kihei Ali'i Kai is a wonderful property located just across the street from the best beach in Kihei; Kamaole Beach #1. This property is in walking distance to shops, activities and restaurants and is a short drive from the championship golf...

    Pool Hot Tub
    FREE CANCELLATION

    $128 to $208/night

  14. CONDOMINIUM
    Kanai A Nalu 302

    Kanai A Nalu 302

    Wailuku, HI

    Oceanfront ocean view third floor! Gorgeous upgraded condo. Quiet home listen to the sounds of the sea. Welcome to Kana'i A Nalu a quiet resort that sits on the ocean away from the road. This property has the BEST ocean front views of Molokini...

    Pool
    FREE CANCELLATION

    $212 to $448/night

  15. CONDOMINIUM
    Maui Kaanapali Villas #A221

    Maui Kaanapali Villas #A221

    Lahaina, HI

    Welcome to Maui Kaanapali Villa Studio #221 on the 2nd floor of the Aloha Tower. This condo sleeps 4 with a king bed and a queen sofa sleeper. Condo features a 50 inch flat screen TV. Plans for kitchen and bathroom remodel slated for Fall 2019:...

    Pool
    FREE CANCELLATION

    $191 to $383/night

  16. APARTMENT
    Mauka Lani (KAUAI)

    Mauka Lani (KAUAI)

    Princeville, HI

    This villa at Villas of Kamalii, Princeville, is an upscale luxurious and tropically decorated, two bedroom, three bath Villa. Two large en-suite bedrooms, one queen with a shower and one king with jacuzzi tub downstairs, and a third reading room on...

    $363 to $744/night

  17. HOUSE
    Sands Of Kahana 318

    Sands Of Kahana 318

    Kahana, HI

    This one bedroom, two bath condominium comes with all the amenities to make your time in paradise truly memorable. Watch the dolphins go by or the turtles on the beach. You will be steps to the ocean, pool, and activities. Recent enhancements...

    Pool Hot Tub

    $236 to $276/night

  18. CONDOMINIUM
    Kihei Bay Vista #D-202

    Kihei Bay Vista #D-202

    Kihei, HI

    Located across the street from Kalepolepo Beach and the Pacific Whale Sanctuary in Kihei Maui, the Kihei Bay Vista is a great property. It is just steps from a long sandy walking beach. It has a pool and hot tub, gas grills for your use as well as...

    Pool
    FREE CANCELLATION

    $126 to $231/night

  19. CONDOMINIUM
    Maui Eldorado, Maui Condo G203

    Maui Eldorado, Maui Condo G203

    Kaanapali, HI

    Maui Eldorado vacation rental in the heart of Kaanapali at the Maui Eldorado Resort. Surrounded by palm and plumeria trees with expansive views of the main pool and partial view of the ocean. Perfect for the couple seeking an exquisite 5 star luxury...

    Pool
    FREE CANCELLATION

    $187 to $408/night

  20. CONDOMINIUM
    O-924: Hale Alii Ko Olina Beach Villa

    O-924: Hale Alii Ko Olina Beach Villa

    Kapolei, HI

    Overview: This 2 BR, 2 BA luxury villa on the 9th floor of the Ocean Tower at the Ko Olina Beach Villas is conveniently located just 20 miles from Honolulu International Airport on the beautiful southwestern shores of Oahu. The four pristine beaches...

    Pool

    $369 to $1,204/night

  21. CONDOMINIUM
    Junior Suite Oceanfront 707

    Junior Suite Oceanfront 707

    Kaanapali, HI

    Our 7th floor Junior Suite is spacious and well-appointed with a Queen Bed; as well as a queen sofa sleeper for the occasional guest. There are seating arrangements for relaxing and dining. You will find plenty of space to store your clothing and...

    Pool Hot Tub
    FREE CANCELLATION

    $258 to $309/night

  22. HOUSE
    Plantation Cottage at Poipu

    Plantation Cottage at Poipu

    Koloa, HI

    Island living at its finest! Experience charming plantation style living in this gorgeous Poipu home. Enjoy all the Robert Trent Jones, Jr. community has to offer conveniently located along the Kiahuna Golf Course. Shopping, golf, and beach...

    Pool Hot Tub

    $720 to $1,910/night

  23. CONDOMINIUM
    Cliffs 6301

    Cliffs 6301

    Princeville, HI

    Located on top floor at the very end of building 6 this one bedroom with the loft serving as a second bedroom offers you a 180 degree view of the spectacular deep blue waters of Kauai’s northern coastline from the open air lanai, with serene quiet...

    Pool Hot Tub

    $271 to $392/night

  24. CONDOMINIUM
    Kona Plaza 201

    Kona Plaza 201

    Kailua Kona, HI

    Please note that this property was previously managed by Boundless Hawaii, during which time it earned a guest rating of 4.6, based on over 50 reviews. In the interest of providing our guests with the highest level of service, we at Boundless Hawaii...

    Pool

    $268 to $562/night

  25. CONDOMINIUM
    Sea Village 1-205-Oceanfront

    Sea Village 1-205-Oceanfront

    Kailua Kona, HI

    Lovely oceanfront 2nd floor unit totally upgraded and showing beautifully. Lanai seats four for outside dining with fab views of Kona Bay and those unforgettable Kona Sunsets. Very popular vacation complex with Oceanfront Pool and Hot Tub, BBQ and...

    Pool

    $194 to $279/night

  26. CONDOMINIUM
    Sea Village 1-203

    Sea Village 1-203

    Kailua-Kona, HI

    Sea Village Resort sits right on the sea wall. Located on prestigious Alii Drive. The well kept grounds surround a newly renovated pool, spa, barbeque and tennis court. Walk to town for a morning cup of the famous Kona coffee, shopping and evening...

    Pool

    $164 to $231/night

  27. HOUSE
    Kahana Sunset C4

    Kahana Sunset C4

    kahana, HI

    Enjoy a relaxing vacation at a friendly and beautiful small resort by the ocean, to which satisfied guests return year-after-year. The apartment has 2 fully separated bedrooms, each with its own bathroom, and an additional sofa bed sleeping 2 in the...

    Pool

    $219 to $276/night

  28. HOUSE
    Bay Villa 38G2

    Bay Villa 38G2

    Kapalua, HI

    This is a beautiful remodeled unit ocean view unit! It has stainless steele appliances, tile floors, granite countertops, flat screen TV's, DVD, CD player, all new furniture, king bed with queen sofa sleeper in livingroom, free internet hook-up, and...

    Pool

    $248 to $304/night

  29. HOUSE
    Kahana Sunset A4

    Kahana Sunset A4

    Kahana, HI

    Incredible townhouse condominium with the perfect oceanfront location right next to one of Maui’s most beautiful and safest reef-protected beaches. This beautiful townhouse condominium has just undergone a complete designer remodel. The remodel...

    Pool

    $428 to $484/night

  30. CONDOMINIUM
    Villas on the Prince 34

    Villas on the Prince 34

    Princeville, HI

    The gated, upscale Villas on the Prince is located in Princeville on the north shore of Kauai. These spacious 1800sf Kauai vacation rentals enjoy nearby beach path access to Anini Beach, with its tranquil shallow waters and long sandy ocean floor....

    Pool Hot Tub
    FREE CANCELLATION

    $164 to $183/night