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
    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

    $1,017 to $2,408/night

  2. 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

    $912 to $2,147/night

  3. CONDOMINIUM
    Beach Level Studio Direct Ocean Views Villa 105

    Beach Level Studio Direct Ocean Views Villa 105

    Kahuku, HI

    Beach Level Studio (Or 4 Bed with Adjoining 3 Bed) Direct Ocean Views Villa 105 This villa is located on the beach level just 30 yards from the sandy beach and 50 yards from the pool! It has all new top of the line furniture including a sleeper sofa...

    Pool Hot Tub

    $502 to $907/night

  4. 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

    $964 to $2,277/night

  5. CONDOMINIUM
    Kahana Villa F406 1Bdrm

    Kahana Villa F406 1Bdrm

    Lahaina, HI

    Welcome to the Kahana Villas and our beautiful newly remodeled high end furnished condo. A wonderful view of the ocean and the tropical landscaped grounds are yours to enjoy in this 4th level ocean view one-bedroom, one-bath condo. This home sleeps...

    Pool Hot Tub
    FREE CANCELLATION

    $179 to $320/night

  6. 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

  7. CONDOMINIUM
    Palms at Wailea #1105

    Palms at Wailea #1105

    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

    $347 to $521/night

  8. 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

  9. CONDOMINIUM
    Kamaole Sands #10-312

    Kamaole Sands #10-312

    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

    $174 to $348/night

  10. 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

  11. 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

  12. 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

  13. 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

  14. CONDOMINIUM
    Colony Villas at Waikoloa Beach Resort #2503

    Colony Villas at Waikoloa Beach Resort #2503

    Waikoloa, HI

    Kohala Coast OasisNestled poolside in a luxury gated community on the Kohala coast (which sport the very best beaches on the Big Island), this 1,446 square foot spacious townhome is surrounded by gorgeous lush gardens, has an open floor plan with...

    Pool Hot Tub
    FREE CANCELLATION

    $221 to $464/night

  15. CONDOMINIUM
    Sugar Beach Resort PH 14

    Sugar Beach Resort PH 14

    Kihei, HI

    The Sugar Beach Resort is the perfect destination for your tropical Hawaiian getaway! This oceanfront complex is just a few steps away from Maui's longest continual white sand beach, perfect for long strolls on the beach or enjoying postcard...

    Pool Hot Tub
    FREE CANCELLATION

    $358 to $579/night

  16. CONDOMINIUM
    Kolepa Aloha

    Kolepa Aloha

    Waikoloa, HI

    Description :Views of Mauna Kea and emerald fairways are yours at this two-bedroom, two-bath vacation rental at Fairway Villas, located within the prestigious Waikoloa Beach Resort. Step onto your private, covered lanai with the day's first cup of...

    Pool Hot Tub

    $162 to $401/night

  17. CONDOMINIUM
    Hale Ili Ili #A

    Hale Ili Ili #A

    Kihei, HI

    Hale Ili Ili is an oceanfront gated 4 plex.This property is steps from Kamaole Beach #1 and Charley Young's Cove. Panoramic ocean views and magnificent sunsets can be seen daily from this property. This property has an oceanfront pool, hot tub and...

    Pool Hot Tub
    FREE CANCELLATION

    $695 to $1,043/night

  18. CONDOMINIUM
    Grand Champions #151

    Grand Champions #151

    Wailea, HI

    THE VILLA LOCATION: Our REMODELED and PROFESSIONALLY DECORATED villa overlooks the gorgeous fairways of the Wailea Blue golf course, our location is known as GOLF FRONT. Watch the putting on the 1st green! We are located in a very private and serene...

    Pool Hot Tub
    FREE CANCELLATION

    $193 to $429/night

  19. CONDOMINIUM
    Palms at Wailea #603

    Palms at Wailea #603

    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 stretch of beach. The Palms at Wailea is a gorgeous property; lush with tropical landscaping. There...

    Pool Hot Tub
    FREE CANCELLATION

    $310 to $639/night

  20. CONDOMINIUM
    Kamaole Sands #5-103

    Kamaole Sands #5-103

    Kihei, HI

    Kamaole Sands is the premiere property in South Kihei. It is located across the street from Kamaole Beach III. Have a picnic, whale watch, swim, snorkel, stand-up paddle board, walk miles on the beach and watch the most amazing sunsets imaginable....

    Pool Hot Tub
    FREE CANCELLATION

    $133 to $360/night

  21. CONDOMINIUM
    Kona Makai 3-203

    Kona Makai 3-203

    Kailua Kona, HI

    Kona Makai 3-203 is a beautifully appointed 2nd floor condo with a partial ocean view. The owner has completely remodeled the bathroom with a walk in shower in 2015! This condo is fully equipped with everything you may need for your Vacation! Your...

    Pool Hot Tub
    FREE CANCELLATION

    $256 to $326/night

  22. CONDOMINIUM
    Hali'i Kai at Waikoloa Beach Resort 9F

    Hali'i Kai at Waikoloa Beach Resort 9F

    Waikoloa, HI

    On the sun-drenched Kohala coast on the Big Island of Hawaii, the elements have come together to create a place like no other. It is at this point of convergence that we have chosen to situate our residential community Hali’i Kai at Waikoloa....

    Pool Hot Tub

    $409 to $689/night

  23. CONDOMINIUM
    Kamaole Sands #1-406

    Kamaole Sands #1-406

    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

    $284 to $589/night

  24. CONDOMINIUM
    Palms at Wailea #702

    Palms at Wailea #702

    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, whale watching and strolling. The Palms at Wailea is a gorgeous property; lush with tropical landscaping....

    Pool Hot Tub
    FREE CANCELLATION

    $254 to $523/night

  25. CONDOMINIUM
    Kamaole Sands #7-408

    Kamaole Sands #7-408

    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

    $297 to $615/night

  26. CONDOMINIUM
    Palms at Wailea #1005

    Palms at Wailea #1005

    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

    $309 to $639/night

  27. CONDOMINIUM
    Big Island Paradise

    Big Island Paradise

    Waikoloa, HI

    Sprawling, Exclusive Hali’i Kai Condo 22FImagine this: You wake up to balmy Hawaiian breeze and wander onto your bedrooms personal lanai to watch the morning sun on the mountains. After a hike along the lava-rock seashore, you take a dip in the...

    Pool Hot Tub

    $330 to $689/night

  28. HOUSE
    Hale Honu-Oceanfront

    Hale Honu-Oceanfront

    Kailua Kona, HI

    Oceanfront estate with breathtaking panoramic unobstructed views. 4 BR, 4 elegant baths. All bedrooms have oceanfront balconies. Walls of glass open to lanai & main living area making this an ideal Hawaiian indoor/outdoor living experience. Elegant...

    Hot Tub
    FREE CANCELLATION

    $766 to $846/night

  29. CONDOMINIUM
    Makena Surf Resort, #G-201

    Makena Surf Resort, #G-201

    Kihei, HI

    akena Surf Resort is a luxurious secluded beachfront condominium located in exclusive Makena. This gated community was developed with six 2 & 3 story buildings each offering sweeping views of the Pacific. The pristine and picturesque beach and rocky...

    Pool Hot Tub

    $775 to $1,094/night

  30. CONDOMINIUM
    Wailea Elua Unit #0307

    Wailea Elua Unit #0307

    Wailea, HI

    A note from the owner: Welcome to Wailea Elua Village #307, our newly remodeled ground floor condo and our piece of paradise. With outstanding views, beach access through beautifully sculpted gardens, and Hawaiian-home class, it has everything you...

    Pool Hot Tub

    $459 to $953/night