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. HOUSE
    Kauhale Pilialoha

    Kauhale Pilialoha

    Kamuela, HI

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

    Pool Hot Tub

    $18953 to $29061/night

  2. VILLA
    Hale Waiulu #150470

    Hale Waiulu #150470

    Kailua Kona, HI

    Our well-appointed home has everything you could possible need. Fresh, home grown mango, guava and finger lime for our guests to feast on . Enjoy the relaxing sound of the cascading rush of your private pool's waterfall. The lush golf green views of...

    Pool Hot Tub

    $2274 to $6318/night

  3. HOUSE
    Hale Pua

    Hale Pua

    Kailua Kona, HI

    Hale Pua (“House of Flowers”) now features AC as an option in all of its sleeping areas: five king bedrooms, one bunkroom with four twin beds and game room with queen sofabed. This special home is maybe the only 6 bed/6 full bath oceanfront...

    Pool

    $2212 to $3444/night

  4. 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

  5. HOUSE
    Papaua Estate

    Papaua Estate

    Lahaina, HI

    APPROVED MAUI SHORT TERM RENTAL HOUSE #STWM 2104/0003. You and your family and friends will love your stay here for a vacation filled with Aloha! If you are looking for location, luxury and Hawaiian life style, you have found it. Perhaps the most...

    Hot Tub
    FREE CANCELLATION

    $1869 to $2874/night

  6. CONDOMINIUM
    The Montage Kapalua Bay Heliconia 2302

    The Montage Kapalua Bay Heliconia 2302

    Kapalua, HI

    Beautiful 3 bedroom/3.5 bath plus Den Residence. Heliconia Residence at Residences at Montage This beautiful 3 bedroom/3.5 bath plus Den home is situated in Building #2 at the Residences at Montage in beautiful Kapalua. Enjoy the ocean views from...

    Pool
    FREE CANCELLATION

    $1506 to $4833/night

  7. HOUSE
    Hale Keanu- Waimea Home

    Hale Keanu- Waimea Home

    Waimea, HI

    Sweeping Ocean Views & Separate Ohana. Rare 4 bedroom - Wai'ula'ula at Mauna Kea Step into a dream at an exceptional four-bedroom ocean-view rental at Wai'ula'ula within the Mauna Kea Resort. At this single level brand-new home, you will find a...

    Pool Hot Tub

    $1390 to $3032/night

  8. HOUSE
    Kona Bay Bliss

    Kona Bay Bliss

    Kailua Kona, HI

    This incredible home is secluded in a 24 hour guard gated oceanfront community, yet is close to all that Kona has to offer. It is located just a short walk from the classic old Hawaiian town of Kailua and the start/finish of the Ironman. In all of...

    $1343 to $2014/night

  9. HOUSE
    Hahalua Hale

    Hahalua Hale

    Kailua Kona, HI

    Welcome to "Hahalua Hale" (House of the Manta Ray) located in a quiet gate community. Located at a perfect coffee growing elevation that receives those cool tropical Hawaiian breezes, this magnificent, one-of-kind, architectural showpiece sited for...

    Pool

    $1261 to $1664/night

  10. 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

  11. 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

  12. HOUSE
    O'oma Plantation

    O'oma Plantation

    Kailua Kona, HI

    Why book individual resorts or condos when your whole group can enjoy a mansion in paradise? Enjoy exceptional panoramic coastal views from the private and quiet custom home at the O’oma Plantation. This large home is the perfect escape for a...

    Pool

    $1179 to $1664/night

  13. CONDOMINIUM
    Ocean View Beachfront Beach Level 4-Bed Turtle Bay Villa 104

    Ocean View Beachfront Beach Level 4-Bed Turtle Bay Villa...

    Kahuku, HI

    Ocean View & Beachfront Beach Level 4-Bedroom (2 Masters) Turtle Bay Villa 104 At Ocean Villa 104 you have dramatic ocean views from just about everywhere! My 4-bedroom villa is located on the beach level so you can walk right out your living room...

    Pool Hot Tub

    $1168 to $3647/night

  14. HOUSE
    Alii Point

    Alii Point

    Kailua Kona, HI

    Experience a vacation of a lifetime in this massive oceanfront custom home tucked away in an exclusive and quiet gated community along the Kona coast. A pond with a waterfall, filled with flowers welcomes you upon entering this beautiful custom...

    Pool Hot Tub

    $1150 to $1605/night

  15. HOUSE
    Hale Grace Aloha

    Hale Grace Aloha

    Kailua Kona, HI

    Searching for vacation rentals with a private pool? Look no further because this is one of the best vacation rentals with a private pool on the Big Island. Nestled in an enclosed tropical garden across the way from the Ali’i outdoor marketplace...

    Pool

    $876 to $1284/night

  16. CONDOMINIUM
    Direct Ocean View Beach Level 3Bed Villa 103

    Direct Ocean View Beach Level 3Bed Villa 103

    Kahuku, HI

    Direct Ocean View Beach Level 3Bed (or 4Bed w/Adjoin Studio) Villa 103 This villa is in the most desirable location in the complex. It has just 20 yards of lawn before the sandy beach and the pool and BBQs are just 50 yards to the right!  It has...

    Pool Hot Tub

    $860 to $2609/night

  17. CONDOMINIUM
    Villa 316

    Villa 316

    Kahuku, HI

    This penthouse villa is located in the most desirable location in the complex, on the third level just steps from the sandy beach with panoramic ocean views and a private serene lanai. This villa is only about 20 yards from the ocean! Photographs...

    Pool Hot Tub

    $860 to $2609/night

  18. CONDOMINIUM
    Hale Lelea Ko Olina Beach Villa (B310)

    Hale Lelea Ko Olina Beach Villa (B310)

    Kapolei, HI

    This vacation home has been registered as a Transient Accommodation with the State of Hawaii – HAWAII TAX ID TA-083-717-4272-01 #groundfloor #view #oceanview #whitewater #group  #wedding #KoOlina #resort #luxury #villa #Kapolei #Oahu #Hawaii...

    Pool Hot Tub

    $856 to $2016/night

  19. HOUSE
    Keauhou Elima

    Keauhou Elima

    Kalilua Kona, HI

    What is better than a Hawaiian sunset over the ocean? A sunset over the ocean that you can take in from the privacy of your tropical home-away-from-home! With nearly 5,000 square feet of indoor/outdoor living space, including a lanai with a pool...

    Pool

    $853 to $1769/night

  20. CONDOMINIUM
    Direct Ocean & Beach View 2nd Level 3Bd Villa 203

    Direct Ocean & Beach View 2nd Level 3Bd Villa 203

    Kahuku, HI

    Direct Ocean & Beach View 2nd Level 3Bd (or 4bd w/adjoin studio) Villa 203This villa is located on the second floor in the most desirable location in the complex, just 20 yards from the sandy beach with direct ocean and beach views from just about...

    Pool Hot Tub

    $808 to $2478/night

  21. CONDOMINIUM
    Beach Level 3 Bed Direct Ocean Views Villa 106 Turtle Bay

    Beach Level 3 Bed Direct Ocean Views Villa 106 Turtle Ba...

    Kahuku, HI

    This beach level villa has beach and ocean views and is located just steps from the sandy beach with a lawn area before the sand starts. The Ocean Villas pool, jaccuzzi and BBQs are all just 20 yards to your right! It has a serene lanai where you...

    Pool Hot Tub

    $808 to $2478/night

  22. VILLA
    Villa Cinco Resort at Kona Plantation Estates

    Villa Cinco Resort at Kona Plantation Estates

    Kailua Kona, HI

    This beautiful custom home, built in 2007, boasts 5 buildings totaling interior 3,829 sq. feet; including main house, and a private master suite situated at each of 4 corners. Main house has a private study converted to bedroom with a sink, a half...

    Pool Hot Tub
    FREE CANCELLATION

    $759 to $1051/night

  23. CONDOMINIUM
    Ocean & Garden View Beach Level 3-Bed Villa 115

    Ocean & Garden View Beach Level 3-Bed Villa 115

    Kahuku, HI

    Beachfront Ocean & Garden View Beach Level by Pool & BBQs 3-Bed Villa 115 This beach level villa is just 20 yards from the sandy beach and 10 yards from the pool and BBQs! It has all new, top of the line, furniture including a sleeper sofa with a...

    Pool Hot Tub

    $756 to $2348/night

  24. HOUSE
    Honu Ohana House 69-1757

    Honu Ohana House 69-1757

    Waimea, HI

    This is a big, fun beach house with several areas to enjoy as a whole group or to tuck away from the rest of the group’s festivities for some private time. Perfect for multi-generational families and/or extended family with friends. The home is...

    Pool

    $756 to $1585/night

  25. CONDOMINIUM
    Kaanapali Alii 456

    Kaanapali Alii 456

    Lahaina, HI

    Our Luxury Ocean View condo is PRIVATELY MANAGED. Our condo is not in the Rental Program, so rest assure that our condo photos that you see here, is the one that you will rent from us. The condo unit is located in building 4 on the 5th floor end...

    Pool
    FREE CANCELLATION

    $749 to $1500/night

  26. CONDOMINIUM
    Ocean and Pool View Beachfront 2nd Floor Villa 208

    Ocean and Pool View Beachfront 2nd Floor Villa 208

    Kahuku, HI

    This villa is located on the second level with Spectacular Ocean and pool views from the lanai, the living room, the dining room, and the master bedroom! This villa is just 35 yards from the sandy beach and 10 yards to the Pool and BBQs. It has...

    Pool Hot Tub

    $703 to $2217/night

  27. CONDOMINIUM
    Ocean & Pool View Beachfront 3rd Floor Penthouse Villa 309

    Ocean & Pool View Beachfront 3rd Floor Penthouse Vil...

    Kahuku, HI

    Ocean & Pool View Beachfront 3rd Floor (top) Penthouse Villa 309 This penthouse villa is located on the third level just steps from the sandy beach with beautiful ocean and pool views from the lanai, living room and master bedroom. It has a serene...

    Pool Hot Tub

    $703 to $2217/night

  28. CONDOMINIUM
    Ocean View and Beachfront Beach Level 3 Bedroom Villa 110

    Ocean View and Beachfront Beach Level 3 Bedroom Villa 11...

    Kahuku, HI

    This beach level villa is located just steps from the pool, BBQs, and the sandy beach! It has partial ocean views from the dining room, kitchen, living room, master bedroom and lanai. It has a serene lanai with Tiki torches lighting the grounds at...

    Pool Hot Tub

    $703 to $2217/night

  29. CONDOMINIUM
    Honua Kai Konea 301

    Honua Kai Konea 301

    Kaanapali, HI

    One of the MOST DESIRABLE 2 bedroom 2.5 bath condo in the entire complex. Konea 301 is one of only 5 Two Bedroom Ali'I Suites with Direct Ocean Views and private Outdoor Kitchens. At 1620 sq ft with a HUGE 415 sq ft lanai this gorgeous home has 180...

    Pool Hot Tub
    FREE CANCELLATION

    $699 to $2099/night

  30. HOUSE
    Hale Lani

    Hale Lani

    Kailua Kona, HI

    Welcome to Hale Lani. This gorgeous house is a Brand New Vacation Rental that Knutson & Associates Management is proud to represent. Hale Lani is the perfect spot to host a unforgettable Hawaii Vacation. With 4 bedrooms, and a capacity to sleep 14,...

    Pool
    FREE CANCELLATION

    $695 to $1758/night