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

Search results

  1. APARTMENT
    Waikiki Grand View Penthouse

    Waikiki Grand View Penthouse

    Honolulu, HI

    Gateway to World Famous Waikiki! This luxury 38th floor Penthouse is in Honolulu's prestigious Waikiki Landmark, presenting exquisite and classical finishes and orchestra views of the finest beaches, shops, and restaurants of Waikiki.  Relish in...

    Pool

    $3468 to $7335/night

  2. HOUSE
    Ali’i Honu Kai House

    Ali’i Honu Kai House

    Kailua-Kona, HI

    Perfectly located on the Kona “Gold Coast” of the Big Island between the charming village of Kailua~Kona and Keahou Bay, this home offers you your own personal paradise. From the moment you drive up to this dramatic gated, Ocean Front Estate you...

    Pool

    $3025 to $4840/night

  3. HOUSE
    Blue Lagoon

    Blue Lagoon

    Kamuela, HI

    A Polynesian resort inspired estate with large heated pool and spa, ideal for a spacious getaway or large group. Upon entering through 10 ft mahogany gates, traversing a bridge over a Koi pond past a waterfall, you will be treated to the luxury...

    Pool Hot Tub

    $2813 to $5955/night

  4. VILLA
    Makena Aloha Estate

    Makena Aloha Estate

    Lahaina, HI

    One of West Maui's most exclusive legally permitted rental properties, the Makena Aloha Estate offers exceptional ocean and mountain views, with gated exclusive privacy and seclusion. With 4,400 square feet of interior dwelling space, this...

    Pool

    $1968 to $3075/night

  5. HOUSE
    Home of the Hula Moon

    Home of the Hula Moon

    Waimea, HI

    Stately and serene, Hula Moon sits on one of the most beautiful properties in Puako. Located at the quiet end of the road, you will enjoy year-round sunsets and privacy. As you enter through the gates, lush tropical plantings enhance the large...

    Pool

    $1876 to $2662/night

  6. VILLA
    Hualalai Resort Ocean Front Golf Villa 4202

    Hualalai Resort Ocean Front Golf Villa 4202

    Kailua Kona, HI

    Whale watch while listening to the breaking waves from the shoreline from the Master bedroom's private lanai with unobstructed ocean views! This beautifully appointed three bedroom villa has over 2,500 square feet of living area. Each of the three...

    FREE CANCELLATION

    $1751 to $5546/night

  7. HOUSE
    Hokulani

    Hokulani

    Honolulu, HI

    Hokulani, Hawaiian for “heavenly star,” is your next luxury vacation destination. New to the market, Hokulani is a relaxing executive estate in the heart of upscale Kahala. This meticulously planned estate furnished by the premier Orange...

    Pool Hot Tub

    $1623 to $4152/night

  8. HOUSE
    Indo Lotus Beach House

    Indo Lotus Beach House

    Wailea, HI

    The Indo Lotus Beach House is one of the few vacation homes on Maui that has a legal grandfathered rental history, combined with a beachfront location. Set on Kamaole One Beach at the 'Charley Young' end, Indo Lotus has direct access to a popular...

    Hot Tub

    $1454 to $2356/night

  9. VILLA
    Hualalai Resort Palm Villa 140B

    Hualalai Resort Palm Villa 140B

    Kailua-Kona, HI

    This Hualalai Palm Villa is a spectacular three bedroom, three bath, two-story Hualalai condo on popular Waiulu Street at the world renowned Hualalai Resort. The Resort is home to the Four Seasons Hualalai, regarded by many as the #1 Resort in...

    Pool
    FREE CANCELLATION

    $1401 to $3736/night

  10. TOWNHOUSE
    Hualalai Resort Haliipua Villa 104

    Hualalai Resort Haliipua Villa 104

    Kailua-Kona, HI

    Built in 2009, Haliipua Villas are the newest generation of multi-family villas at Hualalai offering an array of designer finishes throughout the home. Special features include luxurious mahogany finishes, island-inspired ceiling treatments,...

    FREE CANCELLATION

    $1401 to $3736/night

  11. HOUSE
    The Oasis

    The Oasis

    Kamuela, HI

    Remodeled and redecorated in 2018, The Oasis boasts vaulted ceilings, tropical hardwoods, marble and granite counter tops, air conditioning, and expansive living spaces with plenty of luxurious seating. Along with a professional chef’s kitchen, an...

    Pool

    $1384 to $2811/night

  12. CONDOMINIUM
    Wailea Elua Unit #1305

    Wailea Elua Unit #1305

    Wailea, HI

    A note from the owner: Wailea Elua Village #1305 boasts 3 bedrooms (king bed in the master, queen bed in the 2nd bedroom and 2 twin beds in the 3rd bedroom) and a prime oceanfront ground floor location just steps from the white sands of Elua Beach....

    Pool

    $1346 to $2076/night

  13. VILLA
    4BD Villas at Mauna Kea #21

    4BD Villas at Mauna Kea #21

    Kamuela, HI

    Relax and luxuriate in this spacious and bright four bedroom luxury property, newly renovated, redesigned and brand new to the rental market! Professional and cheerful Fine Design interior decor echoes tones of the nearby Pacific. Unwind on the...

    Pool Hot Tub

    $1337 to $3873/night

  14. VILLA
    3BD Villas at Mauna Kea #39

    3BD Villas at Mauna Kea #39

    Kamuela, HI

    Relax in your own private pool and waterfall spa on a spacious deck while enjoying some of the best panoramic ocean, coastline, sunset, and Maui views in the entire Mauna Kea Resort. This exquisite luxury property, recently renovated and refreshed...

    Pool Hot Tub

    $1261 to $3628/night

  15. 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

    $1254 to $1898/night

  16. HOUSE
    4BD Estate Home at Puako Bay (74)

    4BD Estate Home at Puako Bay (74)

    Kamuela, HI

    This elegant and timeless oceanfront estate is situated on the scenic shores of beautiful Puako Bay. One of Hawaii's last remaining peaceful little beach communities, Puako is steeped in history from abundant fishing to sugar cane farming and epic...

    $1230 to $3575/night

  17. HOUSE
    Pua Lani Home 69-1854

    Pua Lani Home 69-1854

    Waimea, HI

    A sophisticated touch of "old Hawaii" with easy ocean front living.  Large open spaces, Ocean views from two master suites, kitchen and living room with expansive covered lanai across the ocean side of the home.  Enter into two private landscaped...

    Pool

    $1210 to $2420/night

  18. HOUSE
    Aina Malia (4-Bedroom Home)

    Aina Malia (4-Bedroom Home)

    Waimea, HI

    This unique property is situated above beautiful Wailea Bay on the Kohala Coast of the Big Island of Hawaii, one of the few white sand beaches on the island of Hawaii. Beautiful tropical landscaping abounds with privacy and romance. Custom designed...

    $1204 to $2420/night

  19. VILLA
    Hualalai Palm Villa 140C

    Hualalai Palm Villa 140C

    Kailua-Kona, HI

    The spacious floor plan includes a downstairs master bedroom suite with king bed and luxury spa-like bath. Just off the master is a large living room with queen sized sofa pull out that opens to the downstairs lanai, leading to the lawn and golf...

    Pool
    FREE CANCELLATION

    $1168 to $3736/night

  20. VILLA
    Hualalai Resort- Palm Villa 130A

    Hualalai Resort- Palm Villa 130A

    Kailua-Kona, HI

    One of the largest floor plans of any villa at Hualalai, this spacious and centrally located 3 bedroom, 3 bath villa is ideal for your Hawaii getaway. Extra bedding available with a "bonus" living room on the first level. The down-stairs suite opens...

    Pool
    FREE CANCELLATION

    $1168 to $3736/night

  21. VILLA
    Hualalai Resort- Waiulu 137D

    Hualalai Resort- Waiulu 137D

    Kailua-Kona, HI

    This spacious 3 bedroom, 3.5 bath single-level villa is centrally located on the Resort’s popular Waiulu Street overlooking beautiful Punawai Pond, the 5th Hole of the Member’s Ke`olu Golf Course and the ocean beyond. With 2642 square feet of...

    Pool
    FREE CANCELLATION

    $1168 to $3736/night

  22. VILLA
    Hali'ipua Villa #108

    Hali'ipua Villa #108

    Kailua Kona, HI

    Among the newest additions to the exclusive Four Seasons Resort Hualalai, this ocean-view villa provides the perfect setting for a romantic getaway for two or a relaxing retreat to paradise for two couples. The villa boasts over 2,600 square feet of...

    Pool Hot Tub

    $1126 to $3191/night

  23. VILLA
    Hualalai Resort Ke Alaula Villa 210A

    Hualalai Resort Ke Alaula Villa 210A

    Kailua-Kona, HI

    Spectacular three bedroom three bath villa centrally located within the Hualalai Resort. Two story townhome style in the exclusive Ke Alaula neighborhood, just a 3-4 minute cart ride to the Four Seasons Hotel. Fully receding pocket glass, screen and...

    FREE CANCELLATION

    $1109 to $3736/night

  24. VILLA
    Hualalai Resort Hillside 4102

    Hualalai Resort Hillside 4102

    Kailua-Kona, HI

    Location-Location-Location! This spectacular 2 bedroom, 2 bath luxury villa is a short distance to the Four Seasons Resort Hualalai - truly one of the worlds' great resorts. Enjoy the soothing sounds of gentle waves on the shoreline from this ground...

    Pool
    FREE CANCELLATION

    $1109 to $3736/night

  25. HOUSE
    Hawaii Happy Healthy House

    Hawaii Happy Healthy House

    Waimea, HI

    Hawaii Happy Healthy House is a five bedroom, five bathroom (plus powder room) located in the exclusive, gated Kohala Ranch community on the Big island of Hawaii. The Kohala Coast is one of the sunniest destinations in Hawaii with a unique blend of...

    Pool Hot Tub

    $1089 to $1513/night

  26. CONDOMINIUM
    Whaler at Kaanapali Beach 852

    Whaler at Kaanapali Beach 852

    Lahaina, HI

    Sweeping Ocean Views from Molokai to Lanai from this 8th floor Ocean Front condo. Floor to ceiling windows and doors bring the ocean views into the living area and the bedrooms. Ocean views can be enjoyed from the king bed in the master bedroom. The...

    Pool Hot Tub
    FREE CANCELLATION

    $1089 to $1445/night

  27. CONDOMINIUM
    Whaler at Kaanapali Beach 402

    Whaler at Kaanapali Beach 402

    Lahaina, HI

    Ocean Front like you’ve never seen before! Located on the end of the building, this condo sits right on the world famous, Ka’anapali Beach. Enjoy spectacular ocean views from each room, whether you are relaxing on the couch, lying in bed or...

    Pool
    FREE CANCELLATION

    $1089 to $1445/night

  28. VILLA
    Fairways Villa 116C

    Fairways Villa 116C

    Kailua Kona, HI

    Make memories with family and friends in this spacious Waiulu Street ground floor villa, overlooking the 15th hole of the Jack Nicklaus Hualalai Golf Course with the Pacific Ocean and Mount Hualalai beyond. The home features an open floor plan, high...

    Pool Hot Tub

    $1040 to $2918/night

  29. CONDOMINIUM
    2BD Hainoa Villa (2901B) at Four Seasons Resort Hualalai

    2BD Hainoa Villa (2901B) at Four Seasons Resort Hualalai...

    Kailua Kona, HI

    An upstairs residence at Four Seasons Resort Hualalai, 2901B offers the ultimate in Big Island luxury. With amazing ocean and sunset views, central air conditioning, stylish décor, and use of a golf cart included in every rental, this villa...

    Pool

    $1027 to $2188/night

  30. VILLA
    Hualalai Resort Fairway Villa 104D

    Hualalai Resort Fairway Villa 104D

    Kailua-Kona, HI

    Upper level 2-bedroom, 2-bath villa overlooking the 15th tee of the Hualalai Golf Course with stunning Mauna Kea, Island of Maui and horizon views of the ocean. Designed by Honolulu-based Architect Warren Sunnland, the Fairway Villas at Hualalai are...

    Pool
    FREE CANCELLATION

    $934 to $2335/night