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
    Kihei Bay Surf #226

    Kihei Bay Surf #226

    Kihei, HI

    The Kihei Bay Surf is located in North Kihei across the street from the Humpback Whale Marine 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...

    Pool Hot Tub
    FREE CANCELLATION

    $103 to $173/night

  2. VILLA
    Kapalua Bay Villa 29B2 Ocean Front

    Kapalua Bay Villa 29B2 Ocean Front

    Lahaina, HI

    Kapalua Bay Villa at its best! This oceanfront property represents the best of Kapalua! Currently undergoing a beautiful renovation. New pics on the way! The owner spares no expense in this high end renovation Exotic Acacia Wood floors and a...

    Pool

    $563 to $1,031/night

  3. CONDOMINIUM
    Waikoloa Beach Villas B2

    Waikoloa Beach Villas B2

    Waikoloa, HI

    Come share the enjoyment of our home away from home in Hawaii! We fell in love with the Big Island 30 plus years ago on our honeymoon and have been vacationing here ever since. We love bringing our children and grandchildren because this island...

    Pool Hot Tub
    FREE CANCELLATION

    $209 to $431/night

  4. CONDOMINIUM
    Wailea Ekolu #805

    Wailea Ekolu #805

    Wailea, HI

    Unit #805 has a fully equipped kitchen, split system air conditioning in the living room, guest bedroom, and master bedroom. The unit is equipped with a washer and dryer. The condo has a California king size bed in the master bedroom and two twin...

    Pool
    FREE CANCELLATION

    $249 to $481/night

  5. CONDOMINIUM
    Maui Kamaole #J-219

    Maui Kamaole #J-219

    Kihei, HI

    Kamaole Beach 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 tennis...

    Pool Hot Tub
    FREE CANCELLATION

    $324 to $486/night

  6. CONDOMINIUM
    Hale Ono Loa #316

    Hale Ono Loa #316

    Lahaina, HI

    Enjoy our tropical paradise – Feel tension melt away when take your first look from our unit and see an unobstructed, breath-taking views of Lana'i, Molokai'i and the vast expanse of ocean. It is magnificent at all times of day. Relax to the...

    Pool
    FREE CANCELLATION

    $178 to $263/night

  7. CONDOMINIUM
    New! Updated! Modern, Maui Beachfront with Central A/C

    New! Updated! Modern, Maui Beachfront with Central A/C

    Lahaina, HI

    Most frequently asked questions re: payments, cancellations, our home, and the area, can be answered in the property info, guest reviews, and pictures, below. We kindly ask that you read all of these details, as we offer a lot of amenities that...

    Pool Hot Tub
    FREE CANCELLATION

    $561 to $731/night

  8. CONDOMINIUM
    Pohailani #133

    Pohailani #133

    Lahaina, HI

    A cozy Hawaiian getaway welcomes you at Pohailani 133. This ground floor unit sits at the edge of a lush garden with mature trees and landscaping. Experience serenity and peace in this 2 bedroom condo filled with natural light. A perfect option if...

    Pool
    FREE CANCELLATION

    $183 to $353/night

  9. HOUSE
    Ainamalu 29 at Waikoloa Beach Resort

    Ainamalu 29 at Waikoloa Beach Resort

    Waikoloa, HI

    Come and enjoy a luxurious laid-back island living in our new home located in the beautiful new neighborhood in Waikoloa Beach Resort – Ainamalu. This gated community Ainamalu "Protected, Peaceful Land" is the newest resort community in the...

    FREE CANCELLATION

    $481 to $896/night

  10. CONDOMINIUM
    Fairway Villas Waikoloa O21

    Fairway Villas Waikoloa O21

    Waikoloa, HI

    Designer furnishings, tropical artwork, luxurious linens and toiletries! Outstanding accommodations await you. Conveniently located parking to condo and elevator. Well-appointed, spacious master bedroom features a comfy Cal-king size bed, with...

    Pool Hot Tub
    FREE CANCELLATION

    $197 to $464/night

  11. CONDOMINIUM
    Maui Sunset #A-204

    Maui Sunset #A-204

    Kihei, HI

    Maui Sunset is a fabulous oceanfront property in Kihei that has lush tropical landscaping, large pool which is heated during the winter months, hot tub, gas grills, work out room and tennis courts out on the beach for your use. Guests return here...

    Pool Hot Tub
    FREE CANCELLATION

    $173 to $266/night

  12. VILLA
    Waikoloa Beach Villas C3

    Waikoloa Beach Villas C3

    Waikoloa, HI

    This Villa is in an excellent location right at one of the two lava rock pools that Waikoloa Beach Villas has to offer. The property is located on the ground floor which comes with many benefits. No stairs to climb, which makes bringing groceries...

    Pool Hot Tub
    FREE CANCELLATION

    $184 to $431/night

  13. CONDOMINIUM
    Palms at Wailea #205

    Palms at Wailea #205

    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

    $277 to $521/night

  14. CONDOMINIUM
    Kihei Garden Estates #D-201

    Kihei Garden Estates #D-201

    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

    $139 to $231/night

  15. CONDOMINIUM
    Kanai A Nalu #311

    Kanai A Nalu #311

    Maalaea, HI

    The Kanai A Nalu is an oceanfront property located right in the heart of Ma'alaea Bay. From your lanai you will enjoy the an unobstructed ocean view, with postcard sunsets. In the winter you will enjoy amazing shows put on by the Humpback Whales...

    Pool
    FREE CANCELLATION

    $162 to $324/night

  16. CONDOMINIUM
    Haleakala Shores #B-309

    Haleakala Shores #B-309

    Kihei, HI

    Haleakala Shores is a condominium complex located directly across from Kamaole Beach II and III. The Kamaole Beaches are world class beaches with lifeguards, restrooms, showers, and playground with picnic areas. It has a protected sandy beach which...

    Pool
    FREE CANCELLATION

    $184 to $331/night

  17. CONDOMINIUM
    Waiohuli Beach Hale #D-221

    Waiohuli Beach Hale #D-221

    Kihei, HI

    Waiohuli Beach Hale is a small oceanfront complex located in Kihei Maui Hawaii along a long walking beach and near the bus route. This property has a great aloha feeling with a relaxed and quiet atmosphere. Each unit is steps from the ocean and is...

    Pool
    FREE CANCELLATION

    $157 to $277/night

  18. CONDOMINIUM
    Palms at Wailea #1503

    Palms at Wailea #1503

    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 white sandy shoreline. The Palms at Wailea is a gorgeous property; lush with tropical landscaping....

    Pool Hot Tub
    FREE CANCELLATION

    $418 to $585/night

  19. CONDOMINIUM
    Kihei Kai Nani #8-363

    Kihei Kai Nani #8-363

    Kihei, HI

    Kihei Kai Nani is located right across from the world renowned Kamaole Beach Park #2. This gorgeous beach is famous for its long sandy shoreline, clean clear water for snorkeling, and great body surfing. Whale watch, paddle board, walk the beach...

    Pool
    FREE CANCELLATION

    $161 to $208/night

  20. CONDOMINIUM
    Kamaole Sands #8-310

    Kamaole Sands #8-310

    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

    $157 to $289/night

  21. CONDOMINIUM
    Waiohuli Beach Hale #D-121

    Waiohuli Beach Hale #D-121

    Kihei, HI

    Waiohuli Beach Hale is a small oceanfront complex located in Kihei Maui Hawaii. This property has a great aloha feeling with a relaxed and quiet atmosphere. Each unit is steps from the ocean and is centrally located to great shopping, restaurants,...

    Pool
    FREE CANCELLATION

    $157 to $277/night

  22. HOUSE
    Kalina at Hapuna Beach

    Kalina at Hapuna Beach

    Kamuela, HI

    Hapuna Beach house description Welcome to Kalina at the High Bluffs of Mauna Kea Located on Kohala Coast on the Big Island of Hawaii, this luxurious private home is just a short golf cart ride away from the premier Mauna Kea Golf Course. It is...

    Pool Hot Tub

    $4,524 to $4,955/night

  23. CONDOMINIUM
    Maui Kamaole #J-221

    Maui Kamaole #J-221

    Kihei, HI

    Kamaole Beach 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 on the property and tennis courts available...

    Pool Hot Tub
    FREE CANCELLATION

    $244 to $463/night

  24. CONDOMINIUM
    Hoyochi Nikko #201

    Hoyochi Nikko #201

    Lahaina, HI

    One bedroom with high vaulted ceilings (additional sleeping capacity on sofa bed in living room). Brand new memory foam mattress. This unit has air conditioning in the bedroom along with a comfortable queen size bed. This condo is fully equipped...

    Pool
    FREE CANCELLATION

    $218 to $369/night

  25. CONDOMINIUM
    Turtle Bay Lanikai***90-TVU-0572

    Turtle Bay Lanikai***90-TVU-0572

    Kahuku, HI

    Ground Floor Unit. Great location directly across from the pool. Lanai has a glass table with 4 chairs. A/C in the bedroom. WIFI. 46" flat screen TV with smart Blueray / DVD player, Netflix streaming. Recent upgrades. ( 2014) Welcome to Kuilima...

    Pool
    FREE CANCELLATION

    $191 to $237/night

  26. CONDOMINIUM
    Villas on the Prince 28

    Villas on the Prince 28

    Princeville, HI

    Villas on the Prince 28: NOTE: 30-DAY MINIMUM STAY AT THIS LOCATION. Enjoy this elegant, very private end unit which provides both mountain and golf course views. Inside you'll find three bedrooms and three bathrooms, as well as numberous...

    Pool
    FREE CANCELLATION

    $164 to $183/night

  27. CONDOMINIUM
    Kihei Bay Surf #126

    Kihei Bay Surf #126

    Kihei, HI

    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 and cable TV. In addition there is a large pool, hot tub, tennis...

    Pool Hot Tub
    FREE CANCELLATION

    $103 to $173/night

  28. CONDOMINIUM
    Kihei Bay Surf #136

    Kihei Bay Surf #136

    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 and Cable TV. In addition there is a large pool, hot tub, tennis...

    Pool Hot Tub
    FREE CANCELLATION

    $99 to $173/night

  29. CONDOMINIUM
    Maui Kamaole #L-202

    Maui Kamaole #L-202

    Kihei, HI

    The famous Kamaole Beach 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...

    Pool Hot Tub
    FREE CANCELLATION

    $219 to $440/night

  30. CONDOMINIUM
    Hanalei Colony Resort E3

    Hanalei Colony Resort E3

    Hanalei, HI

    Wow, you'll have this fabulous north shore beach all to yourselves!!! July 1 marks the date our Hanalei Colony Resort rentals re-open to guests - and for a limited time we'll have a special rate available. For a year now, the North Shore past...

    Pool
    FREE CANCELLATION

    $488 to $581/night