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
    Hale Kamaole #318

    Hale Kamaole #318

    Kihei, HI

    Kamaole Beach #3 is just across the street from Hale Kamaole. This beach is one of the best beaches in the world. Whale watch, snorkel, walk the beach and witness the most amazing sunsets imaginable. Hale Kamaole features two pool areas, charcoal...

    Pool
    FREE CANCELLATION

    $249 to $348/night

  2. CONDOMINIUM
    Maui Hill #I-99

    Maui Hill #I-99

    Kihei, HI

    Maui Hill Resort is located minutes from the premier resort area of Wailea. Keawakapu and Kamaole beaches are within walking distance. The resort features a swimming pool, barbecue grills, tennis, a putting green, and shuffleboard. Enjoy free...

    Pool Hot Tub
    FREE CANCELLATION

    $347 to $695/night

  3. CONDOMINIUM
    Kihei Akahi #C-217

    Kihei Akahi #C-217

    Kihei, HI

    Kihei Akahi is just across from Kamaole Beach #1 and it is moderately priced. Each unit has a private lanai, washer and dryer, AC in the living room and ceiling fans throughout. It also has Cable TV/DVD players and high speed internet service. The...

    Pool
    FREE CANCELLATION

    $150 to $242/night

  4. HOUSE
    Kalina at Hapuna Beach

    Kalina at Hapuna Beach

    Kamuela, HI

    Hapuna Beach house descriptionWelcome to Kalina at the High Bluffs of Mauna KeaLocated 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

  5. CONDOMINIUM
    Nohonani #202

    Nohonani #202

    Lahaina, HI

    Unit 202 is a beautiful two bedroom 2 bath unit on the 2nd floor with breathtaking ocean views from the kitchen, dining areas, living room and master bedroom. As with all the Nohonani units, the master bedroom is ocean side and has a sliding door...

    Pool
    FREE CANCELLATION

    $274 to $403/night

  6. CONDOMINIUM
    Nohonani #105

    Nohonani #105

    Lahaina, HI

    Unit #105 is a two bedroom, two bath unit just steps away from the beach. The master bedroom has a king-size bed; and twin beds in the guest bedroom. Free parking and WiFi are provided as well.If you have ever dreamt of lying in bed and going to...

    Pool
    FREE CANCELLATION

    $274 to $353/night

  7. CONDOMINIUM
    AV 302

    AV 302

    Kailua Kona, HI

    Description:Perched above tropical flora and fauna, this one-bedroom, top-floor couple’s retreat in Alii Villa offers plenty of space for two, plus all the classic Kona personality you seek from a Hawaiian resort.Glimpse ocean views as you relax...

    Pool

    $102 to $162/night

  8. CONDOMINIUM
    Leinaala Oceanfront #301

    Leinaala Oceanfront #301

    Kihei, HI

    Leinaala Oceanfront Unit 301 is a 1 bedroom 1 bath fully furnished condo. This property has a panoramic view of the ocean, mountains and sunsets. Watch the whales from your lanai while you have your morning coffee. In addition,this property offers...

    Pool
    FREE CANCELLATION

    $216 to $473/night

  9. CONDOMINIUM
    Shores of Maui #124

    Shores of Maui #124

    Kihei, HI

    Shores of Maui is located across the street from Cove Park in Kihei, a popular surfing and stand-up paddling spot. It features a tennis court, barbecue grills, swimming pool, and hot tub.Same day bookings (meaning arrival is within 24 hours of...

    Pool Hot Tub
    FREE CANCELLATION

    $180 to $209/night

  10. CONDOMINIUM
    Waiohuli Beach Hale #D-122

    Waiohuli Beach Hale #D-122

    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

  11. CONDOMINIUM
    Ocean View from Lanai, Walk to Beach- 2BR w/ Pool

    Ocean View from Lanai, Walk to Beach- 2BR w/ Pool

    Lahaina, HI

    This all-suite 2BR condo boasts the ultimate backdrop for a dream Maui vacation. Relax on a huge covered lanai with sweeping views that stretch out from the Royal Kaanapali Golf Course to the sparkling blue Pacific Ocean.Nestled in the gated...

    Pool Hot Tub
    FREE CANCELLATION

    $255 to $696/night

  12. CONDOMINIUM
    Nohonani #300

    Nohonani #300

    Lahaina, HI

    Nohonani 300 has recently completed a brand new renovation. Improvements include new carpeting and beautiful furnishings. This is an end unit on the third floor giving added privacy and a spectacular crows nest view of the outer islands and golden...

    Pool Hot Tub
    FREE CANCELLATION

    $274 to $403/night

  13. CONDOMINIUM
    Kihei Bay Vista #D-208

    Kihei Bay Vista #D-208

    Kihei, HI

    Located across the street from Kalepolepo Beach and the Pacific Whale Sanctuary in Kihei Maui, the Kihei Bay Vista is a great property. It is just steps from a long sandy walking beach. It has a pool and hot tub, gas grills for your use as well as...

    Pool Hot Tub
    FREE CANCELLATION

    $121 to $219/night

  14. CONDOMINIUM
    Waipuilani Park 2BR w/ Pool- Walk to Beach, Shops

    Waipuilani Park 2BR w/ Pool- Walk to Beach, Shops

    Kihei, HI

    Overlooking tranquil Waipuilani Park, this oceanfront 2BR condo boasts beautiful unobstructed views from the private lanai. As part of the quiet complex at Leinaala, you’ll enjoy access to a grill area and a sparkling pool (steps from your...

    Pool
    FREE CANCELLATION

    $164 to $504/night

  15. CONDOMINIUM
    Keawakapu Views #206

    Keawakapu Views #206

    Kihei, HI

    This is not your typical vacation rental—across the street from the most beautiful beach on Maui, Keawakapu. Constantly being updated. Furnished with unique contemporary and Asian furniture, original art and ethnic artifacts. Comfortable and...

    FREE CANCELLATION

    $157 to $261/night

  16. CONDOMINIUM
    Wailea Ekolu #407

    Wailea Ekolu #407

    Wailea, HI

    Wailea Ekolu Unit 407 is a fabulous ocean view 1 bedroom 2 bath condo with a fully equipped kitchen, granite countertops, and GE Profile appliances. There are panoramic ocean views from the living room, kitchen and the master bedroom. The condo is...

    Pool
    FREE CANCELLATION

    $261 to $347/night

  17. HOUSE
    Hale Keanu

    Hale Keanu

    Kamuela, HI

    Sweeping Ocean Views & Separate Ohana. Rare 4 bedroom - Wai'ula'ula at Mauna Kea.Step into a dream at an exceptional four-bedroom ocean-view rental at Wai'ula'ula within the Mauna Kea Resort.At this single level brand new home, you will find a...

    Pool Hot Tub

    $1,168 to $2,876/night

  18. CONDOMINIUM
    Waipouli Beach Resort A-303

    Waipouli Beach Resort A-303

    Kapaa, HI

    First class Waipouli Beach Resort. Location: Waipouli, East Kauai, Hawaii, USA (Next to the Historic Town of Kapaa).This resort has all the modern-day amenities that you would expect in a Five-Star resort, including a lazy river-style saline pool...

    Pool

    $310 to $404/night

  19. CONDOMINIUM
    Plantations at Princeville #1122

    Plantations at Princeville #1122

    Princeville, HI

    Located along Pepelani Loop and adjacent to the Lakes golf course and Princeville Tennis Club. Natural moss rock and water features make a distinctive entrance and convey a stately address. Plantations #1122 is a 3 bedroom, 3 bath condo with A/C in...

    Pool

    $259 to $311/night

  20. CONDOMINIUM
    Regency at Poipu Kai #721

    Regency at Poipu Kai #721

    Koloa, HI

    This 3 Bedroom, 3 Bath Condo features Hawaiian style furniture and décor, a wonderful granite kitchen with all the amenities of home. The master bathroom features a jetted tub and walk-in marble shower. The living area is complimented with a TV....

    Pool

    $363 to $514/night

  21. CONDOMINIUM
    Plantations at Princeville #111

    Plantations at Princeville #111

    Princeville, HI

    Welcome to our Princeville home on the north shores of Kauai. The Plantation at Princeville is an upscale condo complex with all the amenities you could ever desire including pool and exercise room. Our home is on the corner lot giving you the most...

    Pool

    $253 to $311/night

  22. CONDOMINIUM
    Puu Poa #305

    Puu Poa #305

    Princeville, HI

    Spacious 2 bedroom, 2 bath condo. Washer/Dryer, fully equipped kitchen, stereo, Cable TV, VCR/DVD. Ceiling fans and natural trade winds. From the lanai and atrium of Pu`u Poa Units, the beautiful blue Pacific Ocean of Kauai's North Shore coastline...

    Pool

    $363 to $369/night

  23. CONDOMINIUM
    Pali Ke Kua #204

    Pali Ke Kua #204

    Princeville, HI

    Perched on an ocean bluff near HANALEI BAY, Pali Ke Kua Unit #204 is a two bedroom, two bath, second floor unit with sweeping ocean views.Pali Ke Kua #204 is located in the Princeville Resort on Kauai's verdant North Shore.There is a swimming pool,...

    Pool

    $270 to $305/night

  24. CONDOMINIUM
    Waipouli Beach Resort A-404

    Waipouli Beach Resort A-404

    Kapaa, HI

    First class Waipouli Beach Resort unit A-404 is located in Waipouli, East Kauai, Hawaii, USA (Next to the Historic Town of Kapaa). This 4th floor unit is most sought after for direct ocean views and being the building closest to the ocean.This...

    Pool

    $456 to $572/night

  25. CONDOMINIUM
    1BR w/ Pools, Steps to Kamaole Beach 3

    1BR w/ Pools, Steps to Kamaole Beach 3

    Kihei, HI

    PROPERTY OVERVIEWSituated directly across from famous Kamaole Beach III, this charming 1BR condo affords a peek-a-boo ocean view and the perfect Maui location - walking distance to excellent restaurants and a short drive to more fantastic dining and...

    Pool
    FREE CANCELLATION

    $112 to $401/night

  26. HOUSE
    Kona Bay Seaclusion-Oceanfront

    Kona Bay Seaclusion-Oceanfront

    Kailua Kona, HI

    Beautifully appointed "like new" 2 bedroom 2.5 bath oceanfront home with pool. Gourmet kitchen and huge deck for tanning, dining & sunset cocktails. Upstairs master has shower & hot tub. Sliding doors disappear into walls for the ultimate "on the...

    Pool
    FREE CANCELLATION

    $486 to $608/night

  27. CONDOMINIUM
    Kona Bali Kai 317- Oceanfront

    Kona Bali Kai 317- Oceanfront

    Kailua Kona, HI

    Lovely Oceanfront 3rd floor 2bd/2bth Beautifully maintained unit in Kona Bali Kai, one of Kona's most popular oceanfront destinations. Watch the dolphins, whales (during winter season) surfers, and those magnificent Kona Sunsets right from your own...

    Pool
    FREE CANCELLATION

    $181 to $242/night

  28. HOUSE
    Happy Leilani Hale

    Happy Leilani Hale

    Kailua Kona, HI

    Tucked into the side of the mountain just above Kona at a cooler 600 ft. elevationHappy Leilani Hale has a zen feel to it as you look out over the blue pacific and feel theSoft ocean breezes take you away from it all.Enter through the Asian...

    Pool Hot Tub
    FREE CANCELLATION

    $425 to $729/night

  29. HOUSE
    Hale Nui Ohana

    Hale Nui Ohana

    Kailua-Kona, HI

    If you have a large group or extended family this is the home for you.Hale Nui Ohana (Large family home) is a large 2 story home with panoramic ocean views.Both upper and lower areas have separate entrances.Main upper floor has a full kitchen,...

    FREE CANCELLATION

    $364 to $608/night

  30. 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