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
    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

    $912 to $2,147/night

  2. CONDOMINIUM
    Panoramic Ocean View Second Level Studio 1-Bedroom Villa 217

    Panoramic Ocean View Second Level Studio 1-Bedroom Villa...

    Kahuku, HI

    This villa is in a private location on the second floor with dramatic ocean views just 20 yards from the ocean! The Pool and BBQs and sandy beach are just 60 yards away. Photographs are of the actual villa. This villa has new furniture in the living...

    Pool Hot Tub

    $502 to $907/night

  3. CONDOMINIUM
    Beach Level Studio Direct Ocean Views Villa 102

    Beach Level Studio Direct Ocean Views Villa 102

    Kahuku, HI

    Beach Level Studio (or 4 Bed with Adjoining 3 Bed) Direct Ocean Views Villa 102 This Villa has just 20 yards of lawn before the sandy beach and the pool and BBQs are just 50 yards to the right!  It has spectacular ocean views that you can see from...

    Pool Hot Tub

    $515 to $920/night

  4. CONDOMINIUM
    Second Level Studio Direct Ocean Views Villa 202

    Second Level Studio Direct Ocean Views Villa 202

    Kahuku, HI

    Second Level Studio (or 4 Bed with Adjoining 3 Bed) Direct Ocean Views Villa 202 Villa 202 is just 20 yards from the sandy beach and has amazing ocean views from just about everywhere in the villa! It has new top of the line furnishings including a...

    Pool Hot Tub

    $502 to $907/night

  5. 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

    $1,069 to $2,538/night

  6. 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

    $1,559 to $3,517/night

  7. CONDOMINIUM
    Villa 317

    Villa 317

    Kahuku, HI

    This villa is in a private location on the third floor with dramatic panoramic ocean views, just 20 yards from the ocean and just 80 yards from the sandy beach! Watch the whales swim past while in your living room during migration season! The Pool...

    Pool Hot Tub

    $515 to $920/night

  8. TOWNHOUSE
    Ko Olina Kai Condo (1085E)

    Ko Olina Kai Condo (1085E)

    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

    $218/night

  9. CONDOMINIUM
    Hale Mahina B401

    Hale Mahina B401

    Lahaina, HI

    Enjoy your Maui vacation from the Hale Mahina Resort! This gorgeous 2 bedroom, 2 bath, lush ocean view condo is the perfect place for couples or families looking to experience and explore the island. Equipped with a full kitchen with stainless...

    Pool Hot Tub
    FREE CANCELLATION

    $331 to $686/night

  10. CONDOMINIUM
    Paki Maui 415

    Paki Maui 415

    Lahaina, HI

    Come enjoy the Paki Maui Oceanfront Resort! This 1 bedroom, 1 bath, lush garden view condo is the perfect place for couples, small families and adventurers looking to experience and explore the island for all the wondrous places and memories it...

    Pool Hot Tub
    FREE CANCELLATION

    $136 to $174/night

  11. VILLA
    Vacation Home in Ko Olina Resort

    Vacation Home in Ko Olina Resort

    Kapolei, HI

    Ko Olina Kai is a peaceful gated community that offers all the tranquil privacy you could desire! The interior is spacious and homey with 2 bedrooms, 2 baths, a living room with an adjacent dining space, and a kitchen. This outstanding villa offers...

    Pool Hot Tub
    FREE CANCELLATION

    $152 to $158/night

  12. HOUSE
    Kahakai Estates Hale

    Kahakai Estates Hale

    Kailua Kona, HI

    This charming home is ideally situated in the gated community of Kahakai Estates on the Big Island's spectacular Kona Gold Coast. Experience the seclusion of your own Hawaiian hideaway just two miles southwest of all the incredible attractions and...

    Pool Hot Tub

    $482 to $839/night

  13. CONDOMINIUM
    Waikiki Banyan Tower 1 Suite 3112

    Waikiki Banyan Tower 1 Suite 3112

    Honolulu, HI

    Deluxe High Level Renovated Condo with Ocean & Diamond Head View, Free parking & Wifi Completely renovated in June 2017! New tile flooring all the way through to the lanai, this special unit has a beach feel with modern furnishings. Enjoy a brand...

    Pool Hot Tub

    $180 to $236/night

  14. CONDOMINIUM
    Honua Kai Konea 215

    Honua Kai Konea 215

    Lahaina, HI

    HONUA KAI RESORT AND SPA SUITE 215 welcomes you with so much This spacious studio, 1 bath can accommodate up to 4 guests. Included in our fabulous price are many owner-supplied extras such as: • Beach chairs (2) • Beach umbrella • Beach...

    Pool Hot Tub
    FREE CANCELLATION

    $275 to $413/night

  15. 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 Pets OK

    $1,910 to $4,082/night

  16. COTTAGE
    Mauna Lani KaMilo Home (424)

    Mauna Lani KaMilo Home (424)

    Kamuela, HI

    This spectacular 3 bedroom- 3 bath single-level cottage is located within Kamilo, which is nestled near the heart of the Mauna Lani Resort area. Upon entering Mauna Lani KaMilo Home (424) enjoy the vaulted ceilings and open floor plan which allows...

    Pool Hot Tub

    $481 to $1,286/night

  17. HOUSE
    Awapuhi Hale

    Awapuhi Hale

    Koloa, HI

    Relax into resort-style living in this nearly 2,100-square foot, fully air-conditioned home on a Kiahuna Golf Club fairway in the new Wainani at Poipu neighborhood. Awapuhi Hale is a beautifully appointed single-level home with vaulted ceilings and...

    Pool Hot Tub

    $542 to $1,338/night

  18. HOUSE
    Leilani Kai Hale

    Leilani Kai Hale

    Princeville, HI

    Panoramic mountain views and tropical vegetation surround you in this beautifully updated Princeville luxury home with air conditioning and its own saltwater pool and spa. Complete with stylish furnishings and fine finishes such as granite counter...

    Pool Hot Tub

    $595 to $1,223/night

  19. ESTATE
    Mauna Kea Resort Bluffs 22- The Beach House

    Mauna Kea Resort Bluffs 22- The Beach House

    Kamuela, HI

    This 8,000-square foot luxury estate with 2,750 square feet of outdoor living space is situated on a private, secure cul-de-sac in the Bluffs area of the Kohala Coast. The Beach House at the Bluffs features an award-winning green design, original...

    Pool Hot Tub

    $3,695 to $6,075/night

  20. CONDOMINIUM
    Kona Makai 1-301

    Kona Makai 1-301

    Kailua Kona, HI

    Kona Makai #1-301 is arguably the BEST condo in the entire complex! Being the top floor corner in building 1, the location is undeniably too perfect. Private & upgraded, this is direct oceanfront condo living at its finest. You can't get a better...

    Pool Hot Tub
    FREE CANCELLATION

    $626 to $674/night

  21. CONDOMINIUM
    Kahana Villa F-410

    Kahana Villa F-410

    Lahaina, HI

    F-410 is the newest, most beautifully upgraded unit around - and the prices are FANTASTIC! There is literally nothing more you could ask for in a vacation rental condo. Everything is available to you. Upgraded kitchen, granite counter tops,...

    Pool Hot Tub
    FREE CANCELLATION

    $206 to $263/night

  22. CONDOMINIUM
    Kihei Garden Estates #H-203

    Kihei Garden Estates #H-203

    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

    $157 to $290/night

  23. CONDOMINIUM
    Maui Kamaole #A-102

    Maui Kamaole #A-102

    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

    $168 to $360/night

  24. CONDOMINIUM
    Maui Kamaole #G-107

    Maui Kamaole #G-107

    Kihei, HI

    Kamaole Beach Park III is just across the street 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...

    Pool Hot Tub
    FREE CANCELLATION

    $174 to $348/night

  25. CONDOMINIUM
    Maui Kamaole #A-201

    Maui Kamaole #A-201

    Kihei, HI

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

    Pool Hot Tub
    FREE CANCELLATION

    $277 to $459/night

  26. CONDOMINIUM
    Kamaole Sands #10-205

    Kamaole Sands #10-205

    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

    $191 to $383/night

  27. CONDOMINIUM
    Kihei Bay Surf #250

    Kihei Bay Surf #250

    Kihei, HI

    The Kihei Bay Surf is located in North Kihei across the street from the Whale Sanctuary and Kalepolepo Beach and an ancient Hawaiian fishpond. Each studio has a fully equipped kitchen, Cable TV and can sleep from 2-3 people. In addition there is a...

    Pool Hot Tub
    FREE CANCELLATION

    $115 to $186/night

  28. CONDOMINIUM
    Maui Kamaole #J-103

    Maui Kamaole #J-103

    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

    $196 to $342/night

  29. CONDOMINIUM
    Kamaole Sands #9-203

    Kamaole Sands #9-203

    Kihei, HI

    Kamaole Sands is the premiere property in South Kihei. Located across the street from Kamaole Beach III. A 2 minute walk from the beach park and a 2 minute drive to Shops at Wailea, golf courses and dining makes Kamaole Sands a great 'destination'...

    Pool Hot Tub
    FREE CANCELLATION

    $173 to $208/night

  30. CONDOMINIUM
    Kamaole Sands #3-402

    Kamaole Sands #3-402

    Kihei, HI

    Unit 3-402 is a top floor two bedroom, Two bath condo in Kamaole Sands is located in Preferred Building 3. It has Ocean, Garden and Pool views. Tile flooring from the entry through the living room to the lanai gives a fresh feeling. The living room...

    Pool Hot Tub
    FREE CANCELLATION

    $219 to $347/night