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. HOUSE
    Pair of 2BR Hawaiian Cottages

    Pair of 2BR Hawaiian Cottages

    Honolulu, HI

    Ideal for groups who want both togetherness and privacy, this pair of vintage-inspired Hawaiian cottages are a delightful home base within walking distance to many Honolulu highlights, including legendary Waikiki Beach (20-minute walk), the Honolulu...

    FREE CANCELLATION

    $413 to $493/night

  2. ESTATE
    Ali'i Villa

    Ali'i Villa

    Kailua Kona, HI

    Dream like ocean views, breathtaking sunsets and a stunning infinity pool with spa, await you at this brand-new luxury residence. The home's 2,800 square feet of indoor space and 1,200 square feet of lanai space, create ideal island surroundings for...

    Pool Hot Tub

    $1,077 to $2,386/night

  3. CONDOMINIUM
    Kahana Sunset F6

    Kahana Sunset F6

    Lahiana, HI

    Enjoy snorkeling with the sea turtles, humpback whale watching in the winter or gazing at rainbows, this property is perfect for it all! The Kahana Sunset sits on Keonenui Bay and feels as though it has its own private beach. Conveniently located...

    Pool

    $371 to $484/night

  4. CONDOMINIUM
    Kauhale Makai #330

    Kauhale Makai #330

    Kihei, HI

    Hawaiian for "Village By The Sea," the Kauhale Makai complex is an oceanfront property located in Kihei. This is one of a few buildings in the area with central air conditioning - not window units. This condo stays as cool as you like it. Kihei is...

    Pool Hot Tub
    FREE CANCELLATION

    $161 to $266/night

  5. CONDOMINIUM
    Ilikai #1743

    Ilikai #1743

    Honolulu, HI

    **Please see notes below on Amenity Fee, due to the resort at time of check-in* Panoramic Views of the Pacific Ocean nestled above the Ala Wai Boat Harbor at the Ilikai Hotel. Escape to Hawaii and indulge in sweeping ocean views from the 17th...

    Pool
    FREE CANCELLATION

    $404 to $619/night

  6. 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

  7. CONDOMINIUM
    Turtle Bay Pupukea***NUC 90-TVU-0246

    Turtle Bay Pupukea***NUC 90-TVU-0246

    Kahuku, HI

    Welcome to Kuilima Estates, the condo property located on the grounds of world-renowned Turtle Bay. The condos are surrounded by two beautifully manicured golf courses, and are the only condos on the North Shore. This is a great place to relax,...

    Pool
    FREE CANCELLATION

    $323 to $358/night

  8. CONDOMINIUM
    Haleakala Shores #A-211

    Haleakala Shores #A-211

    Kihei, HI

    Across from Kamaole Beach III. 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...

    Pool
    FREE CANCELLATION

    $150 to $331/night

  9. CONDOMINIUM
    Kihei Bay Surf #257

    Kihei Bay Surf #257

    Kihei, HI

    The Kihei Bay Surf is located in North Kihei across the street from the Whale Sanctuary and Kalepolepo Beach Kihei Bay Surf has a large pool, hot tub, tennis court, gas grills, and a coin-operated common laundry area. Whale watch, windsurf, walk the...

    Pool Hot Tub
    FREE CANCELLATION

    $103 to $173/night

  10. CONDOMINIUM
    Maui El Dorado J218

    Maui El Dorado J218

    LAHAINA, HI

    Maui Eldorado sits in the heart of Kaanapali! Steps away from famous Kaanapali Beach, J218 is the perfect studio unit for your Maui getaway. With the use of the sofa sleeper, this large studio can sleep four guests. Sip on your favorite beverage...

    Pool Hot Tub

    $208 to $259/night

  11. CONDOMINIUM
    Wailea Ekolu #1608

    Wailea Ekolu #1608

    Wailea, HI

    Wailea Ekolu is one of most sought after properties in Wailea as it is nestled on the Wailea Golf Course. The property has a quiet and private atmosphere as the buildings are spread out across the lush tropical foliage. Wailea Ekolu has two lovely...

    Pool
    FREE CANCELLATION

    $312 to $428/night

  12. CONDOMINIUM
    Sands Of Kahana 272

    Sands Of Kahana 272

    Lahaina, HI

    Whether you're snorkeling with the sea turtles, Humpback whale watching in the winter, surfing, SUP’ing or just kicking back on the lanai to enjoy a rainbow, it doesn't get any better than this property. The Sands of Kahana sits on the pristine...

    Pool Hot Tub

    $506 to $563/night

  13. COTTAGE
    The Cottage

    The Cottage

    Kailua-Kona, HI

    "The Cottage", Mahina Meli Makai (Oceanside Honey Moon)This truly oceanfront Cottage, captures spectacular coastline views as well as the captivating ocean right in front of you. The "Honeymoon Getaway" begins the moment you arrive and step through...

    $239 to $379/night

  14. CONDOMINIUM
    Kaleialoha #109

    Kaleialoha #109

    Lahaina, HI

    Kaleialoha #109This DIRECT oceanfront unit has Queen bed and is fully equipped with all basic amenities. AC in living area! New 55" flat screen in living room and 2nd TV in bedroom. Open and airy living area and open kitchen with recent upgrades...

    Pool
    FREE CANCELLATION

    $183 to $384/night

  15. CONDOMINIUM
    Maui Kamaole #B-206

    Maui Kamaole #B-206

    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

    $230 to $473/night

  16. CONDOMINIUM
    Maui Kamaole #H-205

    Maui Kamaole #H-205

    Kihei, HI

    Kamaole Beach Park #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

    $297 to $448/night

  17. CONDOMINIUM
    133

    133

    Kihei, HI

    This is one bedroom ground floor unit decorated in Hawaiian style prints and artwork, with a Garden View and easy access to pool and BBQ. King bed in bedroom and queen hide-a-bed in living room, to sleep four guests comfortably. Kitchen cabinets are...

    Pool
    FREE CANCELLATION

    $188 to $270/night

  18. CONDOMINIUM
    Ridge Villa 1422

    Ridge Villa 1422

    LAHAINA, HI

    Kapalua Resort has an inherent richness of beauty and culture. From snorkeling with the sea turtles in pristine waters on white sandy beaches, or taking in the beautiful views while whale watching from the Kapalua coastal trail, this property has so...

    Pool Hot Tub

    $197 to $248/night

  19. CONDOMINIUM
    Bay Villa 33B2

    Bay Villa 33B2

    Lahaina, HI

    Enjoy the inherent richness of beauty and culture that embellishes what we know today as the Kapalua Resort. From snorkeling with the sea turtles in white sandy beaches with pristine waters, or taking in the beautiful views while whale watching from...

    Pool

    $214 to $270/night

  20. CONDOMINIUM
    Kaleialoha #305

    Kaleialoha #305

    Lahaina, HI

    Nicely updated 3rd floor unit. New King bed, tile throughout. AC, washer/dryer, Free internet, local phone, cable and onsite parking.Near Shopping, Restaurants and all beach activities. Farmer's Market, coffee shop and beach park 3 blks away. Swim...

    Pool
    FREE CANCELLATION

    $183 to $384/night

  21. CONDOMINIUM
    Turtle Bay Hula House Budget NUC 90-TVU-0566

    Turtle Bay Hula House Budget NUC 90-TVU-0566

    Kahuku, HI

    Ground Floor. Older unit. A/C in bedroom. Great rate. On the first fairway of the Fazio Golf Course, steps away from Lei Lei's and a short walk to the beach and hotel. WiFi.Welcome to Kuilima Estates, the condo property located on the grounds of...

    Pool
    FREE CANCELLATION

    $144 to $156/night

  22. 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

  23. CONDOMINIUM
    Hale Ili Ili #D

    Hale Ili Ili #D

    Kihei, HI

    Hale Ili Ili is an oceanfront gated four-plex in Kihei Maui Hawaii. The property lends itself to a very private and relaxed atmosphere with breathtaking sunsets, sounds of the ocean and rustling palm trees. Many whales, turtles, dolphins and rays...

    Pool Hot Tub
    FREE CANCELLATION

    $556 to $927/night

  24. CONDOMINIUM
    Kihei Bay Vista #A-103

    Kihei Bay Vista #A-103

    Kihei, HI

    Kihei Bay Vista #A-103 is a ground floor ocean view 1 bedroom 1 bath fully equipped condo. This includes a full-equipped kitchen with updated wood cabinets and quartz countertops, washer and dryer, air conditioning window unit in the living room...

    Pool Hot Tub
    FREE CANCELLATION

    $126 to $231/night

  25. CONDOMINIUM
    Honua Kai- Hokulani 612- Great Ocean View! 2b/2b

    Honua Kai- Hokulani 612- Great Ocean View! 2b/2b

    Kaanapali, HI

    GREAT SOUTHSIDE OCEAN VIEW!This great 2 bedroom 2 bath 1100 sq ft OCEAN VIEW condo at the Honua Kai resort and spa has just been upgraded with NEW DESIGNER FURNISHINGS, PORCELAIN TILE FLOORING THROUGHOUT and SAMSUNG SMART TV's. It is located on the...

    Pool Hot Tub

    $376 to $1,650/night

  26. CONDOMINIUM
    Kona Nalu 304

    Kona Nalu 304

    Kailua Kona, HI

    Enjoy an amazing Hawaiian vacation in this completely remodeled spacious Air Conditioned, 1200 sq ft 2 bedroom, 2 bath third-floor top floor unit in a private 15-unit, elevator equipped, shoreline complex. This unit has spectacular ocean views from...

    Pool

    $263 to $397/night

  27. CONDOMINIUM
    Sands Of Kahana 474

    Sands Of Kahana 474

    Lahaina, HI

    Whether you're snorkeling with the sea turtles, Humpback whale watching in the winter, surfing, SUP’ing or just kicking back on the lanai to enjoy a rainbow, it doesn't get any better than this property. The Sands of Kahana sits on the pristine...

    Pool Hot Tub

    $501 to $557/night

  28. CONDOMINIUM
    Kihei Garden Estates #E-102

    Kihei Garden Estates #E-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 barbecue feast under the covered pavilion. Enjoy this full outdoor...

    Pool Hot Tub
    FREE CANCELLATION

    $133 to $244/night

  29. CONDOMINIUM
    Hanalei Colony Resort E3

    Hanalei Colony Resort E3

    Hanalei, HI

    Wow, you'll have this fabulous north shore beach all to yourselves!!! All remaining August 2019 dates now discounted! For over a year now, the North Shore past Hanalei has been closed to everyone except local residents. Wildlife, like fish and...

    Pool
    FREE CANCELLATION

    $488 to $581/night

  30. VILLA
    4BD Villas at Mauna Kea #21

    4BD Villas at Mauna Kea #21

    Kamuela, HI

    Relax and luxuriate in this spacious and bright four bedroom luxury property, newly renovated, redesigned and brand new to the rental market! Professional and cheerful Fine Design interior decor echoes tones of the nearby Pacific. Unwind on the...

    Pool Hot Tub

    $2,002 to $4,290/night