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
    Aina Nalu D-207: Affordable luxury at it's best!

    Aina Nalu D-207: Affordable luxury at it's best!

    Lahaina, HI

    Welcome to Paradise! This home is a 2 bedroom, 2 bath condo on the top floor of Aina Nalu, a centrally located, boutique property in downtown Lahaina. Our guests love the proximity to Lahaina Harbor and the shops/restaurants of Front Street,...

    Pool Hot Tub

    $279 to $1,070/night

  2. APARTMENT
    Nohea Villa

    Nohea Villa

    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...

    Pool Hot Tub

    $393 to $863/night

  3. CONDOMINIUM
    Hawaii Living! Close to Beaches! 2 Bed/2 Bath

    Hawaii Living! Close to Beaches! 2 Bed/2 Bath

    Waikoloa, HI

    2 bedroom 2 bath unit at the Waikoloa Villas in conveniently located Waikoloa Village. Enjoy golf and ocean views. Complex includes two pools, jacuzzis and two large bbq areas. Unit will accommodate 4 people comfortably. This unit is close to nearby...

    Pool Hot Tub
    FREE CANCELLATION

    $164 to $244/night

  4. 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

    $780 to $2,199/night

  5. HOUSE
    Keauhou Estates #185

    Keauhou Estates #185

    Kailua Kona, HI

    Experience privacy and panoramic Pacific views just ten minutes from endless dining and shopping options in downtown Kailua-Kona. Situated in the exclusive gated Keauhou Estates community, this elegant custom home features three bedrooms and two...

    Hot Tub

    $482 to $780/night

  6. CONDOMINIUM
    Kaanapali Royal #A201 (MAUI)

    Kaanapali Royal #A201 (MAUI)

    Lahaina, HI

    FALL SPECIAL! 10% off until the end of November!Experience five-star Maui luxury at an affordable price! This modern ground-floor unit at Kaanapali Royal features a spacious floor plan that opens to sweeping golf course views. Extensively remodeled...

    Pool Hot Tub

    $393 to $1,336/night

  7. HOUSE
    Kiahuna Plantation Hale

    Kiahuna Plantation Hale

    Koloa, HI

    Enjoy the ultimate Poipu vacation experience at Kiahuna Plantation Hale, located on the fourth fairway of the Kiahuna Plantation Golf Course in lovely Wainani at Poipu. This stunning home boasts gorgeous mountain views, a split air conditioning...

    Pool Hot Tub

    $542 to $1,508/night

  8. HOUSE
    Hale Anu Keanu

    Hale Anu Keanu

    Princeville, HI

    With an ideal location, plenty of privacy, and a backyard jacuzzi, this newly remodeled, plantation-style vacation home on Kauai's north shore allows you to experience the perfect balance of relaxation and adventure. Meaning “house of cool...

    Hot Tub

    $631 to $1,693/night

  9. HOUSE
    Junior Suite Oceanfront #303

    Junior Suite Oceanfront #303

    Lahaina, HI

    Jr. Suite - Bright and Easy Island Style. Queen bed (no sofa bed), tiled entryway, Flat Screen TV, light furnishings throughout. Put away your groceries and make yourself at home. Enjoy your private lanai with your favorite beverage. Watch the...

    Pool Hot Tub
    FREE CANCELLATION

    $278 to $341/night

  10. CONDOMINIUM
    Palms at Wailea #1209

    Palms at Wailea #1209

    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

    $267 to $365/night

  11. CONDOMINIUM
    Wailea Elua #701

    Wailea Elua #701

    Wailea, HI

    The Wailea Elua is the premier ocean front property in Wailea. Situated right on Ulua Beach, it has one of the best locations in Wailea. There are miles of spectacular walking paths that follow the ocean In addition the property has two swimming...

    Pool Hot Tub
    FREE CANCELLATION

    $493 to $922/night

  12. CONDOMINIUM
    Kihei Garden Estates #A-102

    Kihei Garden Estates #A-102

    Kihei, HI

    Kihei Garden Estates is a lovely property right across the street from Waiohuli Beach. Kihei Garden Estates boasts a family friendly gathering area, seating up to 25 people to your Bar-B-Q feast under the covered pavilion. Enjoy this full outdoor...

    Pool Hot Tub
    FREE CANCELLATION

    $115 to $196/night

  13. CONDOMINIUM
    Kamaole Sands #9-207

    Kamaole Sands #9-207

    Kihei, HI

    We welcome you to this beautiful condo at the Kamaole Sands #9-207 (second closest bldg to the BEACH) – Design by Jillian Harris (Designer from the famous Extreme Home Makeover Home Edition television series)Same day bookings (meaning arrival is...

    Pool Hot Tub
    FREE CANCELLATION

    $150 to $273/night

  14. CONDOMINIUM
    Maui Kamaole #A-202

    Maui Kamaole #A-202

    Kihei, HI

    Unit A-202 has been completely renovated. This renovation includes: the kitchen cabinets, granite countertops, new kitchen appliances; lighting, carpeting and new tile everywhere; redesigned bathrooms with walk-in showers, new bathroom cabinets and...

    Pool Hot Tub
    FREE CANCELLATION

    $289 to $405/night

  15. CONDOMINIUM
    Kihei Garden Estates #G-103

    Kihei Garden Estates #G-103

    Kihei, HI

    Kihei Garden Estates is a lovely property right across the street from Waiohuli Beach. Kihei Garden Estates boasts a family friendly gathering area, seating up to 25 people to your barbecue feast under the covered pavilion. Enjoy this full outdoor...

    Pool Hot Tub
    FREE CANCELLATION

    $145 to $244/night

  16. CONDOMINIUM
    Hale Moana Ko Olina Beach Villa (B305)

    Hale Moana Ko Olina Beach Villa (B305)

    Kapolei, HI

    Book with confidence! This vacation rental is a LEGAL Oahu vacation rental operating in a Resort Zoned District and is not affected by the passage of Bill 89.LIVE CALENDAR: If the calendar shows as available, the property IS available and can be...

    Pool Hot Tub

    $397 to $1,268/night

  17. CONDOMINIUM
    Kamaole Sands #6-408

    Kamaole Sands #6-408

    Kihei, HI

    Kamaole Sands is the premiere property in South Kihei. Kamaole Sands is located across the street from Kamaole Beach III. Whale watch, swim, snorkel, walk miles on the beach and watch the most amazing sunsets imaginable. There are 15 acres of lush...

    Pool Hot Tub
    FREE CANCELLATION

    $232 to $347/night

  18. CONDOMINIUM
    Maui Kamaole #A-203

    Maui Kamaole #A-203

    Kihei, HI

    Kamaole Beach #3 is just across from the upscale Maui Kamaole. This property features lush tropical landscaping, two gorgeous pool areas with hot tubs and water features. There are gas grills peppered throughout the property and tennis courts...

    Pool Hot Tub
    FREE CANCELLATION

    $302 to $458/night

  19. CONDOMINIUM
    Hale Lanikai Ko Olina Beach Villa (O1104)

    Hale Lanikai Ko Olina Beach Villa (O1104)

    Kapolei, HI

    Book with confidence! This vacation rental is a LEGAL Oahu vacation rental operating in a Resort Zoned District and is not affected by the passage of Bill 89.LIVE CALENDARIf the calendar shows as available, the property is not reserved and can be...

    Pool Hot Tub

    $408 to $1,384/night

  20. APARTMENT
    Waikiki Banyan Tower 2 Suite 2310

    Waikiki Banyan Tower 2 Suite 2310

    Honolulu, HI

    2 Full Sized Beds, Waikiki Banyan, Free WiFi and ParkingEnjoy a fully-equipped kitchen and comfortable seating in the living room. Kitchen includes refrigerator, range, microwave, rice maker, coffee maker, and other standard kitchen wares. All...

    Pool Hot Tub

    $180 to $259/night

  21. CONDOMINIUM
    Valley Isle Resort #901 (MAUI)

    Valley Isle Resort #901 (MAUI)

    Lahaina, HI

    Welcome to Paradise. This is a unique property, right after Kaanapali Beach, featuring this outstanding oceanfront unit with panoramic views of the Pacific Ocean and the islands of Lanai and Molokai.The unit has a fully equipped kitchen, a...

    Pool Hot Tub

    $302 to $481/night

  22. HOUSE
    Hale Alaula- Ocean View

    Hale Alaula- Ocean View

    Kailua Kona, HI

    May Special! 15% Off Nightly Rates for Reservations through June!Hale Alaula- (House of Sunset Glow)Bring the whole family to our home within the beautiful Malulani Gardens, a gated Community in Kailua-Kona! There's plenty of space for everyone,...

    Hot Tub

    $393 to $1,041/night

  23. CONDOMINIUM
    Hale Nani Ikena Kai Ko Olina Beach Villa (B109)

    Hale Nani Ikena Kai Ko Olina Beach Villa (B109)

    Kapolei, HI

    Book with confidence! This vacation rental is a LEGAL Oahu vacation rental operating in a Resort Zoned District and is not affected by the passage of Bill 89.LIVE CALENDAR: If the calendar shows as available, the property IS available and can be...

    Pool Hot Tub

    $548 to $2,016/night

  24. CONDOMINIUM
    Hale Papakea Ko Olina Beach Villa (B110)

    Hale Papakea Ko Olina Beach Villa (B110)

    Kapolei, HI

    Book with confidence! This vacation rental is a LEGAL Oahu vacation rental operating in a Resort Zoned District and is not affected by the passage of Bill 89.LIVE CALENDAR: If the calendar shows as available, the property IS available and can be...

    Pool Hot Tub

    $548 to $2,016/night

  25. CONDOMINIUM
    Kamaole Sands #4-408

    Kamaole Sands #4-408

    Kihei, HI

    Kamaole Sands is the premiere property in South Kihei. Located across the street from Kamaole Beach III. Whale watch, swim, snorkel, walk miles on the beach and watch the most amazing sunsets imaginable. There are 15 acres of lush tropical...

    Pool Hot Tub
    FREE CANCELLATION

    $261 to $406/night

  26. CONDOMINIUM
    Honua Kai Konea 224

    Honua Kai Konea 224

    Lahaina, HI

    This luxury Honua Kai one bedroom located in the 'Konea Tower' features everything you need to make your Hawaiian vacation truly enjoyable!We provide you with those extra amenities that make a difference, including comfortable beach chairs, beach...

    Pool Hot Tub
    FREE CANCELLATION

    $217 to $401/night

  27. CONDOMINIUM
    Kamaole Sands #6-108

    Kamaole Sands #6-108

    Kihei, HI

    This is a beautiful ground floor spacious condo with a new king size bed in the master bedroom and a new queen sleeper sofa with memory foam mattress in the living room and two bathrooms. Because of the unique sea life tile floor, custom mural...

    Pool Hot Tub
    FREE CANCELLATION

    $151 to $360/night

  28. CONDOMINIUM
    Kihei Bay Surf #144

    Kihei Bay Surf #144

    Kihei, HI

    Kihei Bay Surf unit 144 is a beautifully remodeled studio that can sleep up to 3 with a queen bed and a queen Tommy Bahama sofa bed. The unit is conveniently located on the lower level, and the lanai overlooks the pool area. This tiled unit features...

    Pool Hot Tub
    FREE CANCELLATION

    $104 to $168/night

  29. CONDOMINIUM
    Luana Kai #B-203

    Luana Kai #B-203

    Kihei, HI

    Luana Kai is a large oceanfront complex in Kihei. It is centrally located to shops, activities, and restaurants. It features a large oceanfront pool, hot tub, shuffleboard, and gas grills for your use. There is an expansive lawn between the...

    Pool Hot Tub
    FREE CANCELLATION

    $184 to $335/night

  30. CONDOMINIUM
    Villas on the Prince 34

    Villas on the Prince 34

    Princeville, HI

    NOTE: 30-DAY MINIMUM STAY AT THIS LOCATION. Villas on the Prince 34 is a spacious luxury town house with pool and easy walking distance to Anini Beach and Princeville shopping. This beautifully cared for villa has 3 bedrooms and 2 1/2 baths. Two...

    Pool Hot Tub
    FREE CANCELLATION

    $175 to $183/night