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
    Wailea Elua Unit #807

    Wailea Elua Unit #807

    Wailea, HI

    Wailea Elua Village is an exclusive beachfront property located in the heart of the resort community of Wailea. This relaxing low-density property consists of two-story buildings terraced over twenty-four acres of immaculate tropical landscaping....

    Pool

    $329 to $528/night

  2. CONDOMINIUM
    Wailea Ekolu Unit #914

    Wailea Ekolu Unit #914

    Wailea, HI

    Wailea Ekolu Village is a tranquil terraced property located on the Wailea Blue Golf Course offering distant panoramic views of the Pacific. This quiet low-density village consists of eighteen two-story buildings spread out over 18 acres of tropical...

    Pool

    $328 to $584/night

  3. CONDOMINIUM
    Noelani #110

    Noelani #110

    Lahaina, HI

    Not one, but two oceanfront pools and a Jacuzzi, what more can you ask for? Unit 110 is a ground floor unit with washer and dryer and air conditioning. You'll love just walking out from your private lanai right into the swimming pool. Turtles play...

    Pool Hot Tub
    FREE CANCELLATION

    $326 to $427/night

  4. VILLA
    Kapalua Bay Villa 29G5 Ocean Front

    Kapalua Bay Villa 29G5 Ocean Front

    Kapalua, HI

    Beauty surrounds you in this lovely 1 bedroom 2 bath split level villa. One of few with an ocean view from the master suite! Just steps from the pools and beaches, a short walk to great restaurants, golf and tennis, this lovely two story ocean front...

    Pool

    $325 to $536/night

  5. VILLA
    Kapalua Bay Villa 11G1

    Kapalua Bay Villa 11G1

    Kapalua, HI

    Just a two minute walk to the beach, surrounded by three beautiful pools and tennis courts it is centrally located to be close to everything. Still, you'll be tempted not to leave the luxury of this well appointed villa. Every creature comfort has...

    Pool

    $324 to $576/night

  6. CONDOMINIUM
    Mahana 1008

    Mahana 1008

    Lahaina, HI

    This luxurious 10th floor suite is directly facing the beach with massive floor to ceiling windows. Extensively remolded in 2001. Every night you'll enjoy unobstructed panoramic sunsets with the islands of Molokai and Lanai in the distance. Mahana...

    Pool
    FREE CANCELLATION

    $324 to $750/night

  7. CONDOMINIUM
    Waipouli Beach Resort E106

    Waipouli Beach Resort E106

    Kapaa, HI

    New Listing! Beautiful Luxury Inner Courtyard Garden View, One bedroom, Two bath Condominium at the Beachfront Waipouli Beach Resort on Kauai. This Beautiful Luxury Condominium features luxury furnishings for your comfort by International interior...

    Pool
    FREE CANCELLATION

    $321 to $428/night

  8. CONDOMINIUM
    Waipouli Beach Resort C305

    Waipouli Beach Resort C305

    Kapaa, HI

    Newest Listing! at Waipouli Beach Resort, Kauai - Trip Advisor Certificate of Excellence! Beautiful 2 Bedroom, 3 Bathroom Condo at #1 Rated 1st Class Waipouli Beachfront Resort & Spa on the beautiful island of Kauai. Located on the 2nd floor, this...

    Pool
    FREE CANCELLATION

    $321 to $491/night

  9. CONDOMINIUM
    Hale Ono Loa 109

    Hale Ono Loa 109

    Lahaina, HI

    Our ground floor "Beach House" is uniquely situated on waters edge! Comfortably furnished in an uncluttered "island style," the master bedroom has a King bed with new Sealey Posturepedic firm mattress. The guest bedroom has new queen bed. The living...

    Pool
    FREE CANCELLATION

    $319 to $686/night

  10. CONDOMINIUM
    Mahana Resort Unit #616

    Mahana Resort Unit #616

    Lahaina, HI

    Welcome to Mahana 616. This oceanfront one bedroom, one bath condo with stunning panoramic views of the ocean, beach and outer islands from the living room, dining area, bedroom, and lanai. King bed (new as of July 2018) + queen sofa sleeper allow...

    Pool
    FREE CANCELLATION

    $313 to $669/night

  11. CONDOMINIUM
    Royal Mauian #416

    Royal Mauian #416

    Kihei, HI

    Royal Mauian is a unique six story oceanfront property located in South Kihei offering unobstructed views of the clear blue Pacific. The property and adjacent Kamaole Beach together provide excellent locations for stunning sunsets, snorkeling,...

    Pool

    $313 to $505/night

  12. HOUSE
    Sands Of Kahana 344

    Sands Of Kahana 344

    Kahana, HI

    Whether you're snorkeling with the sea turtles, whale watching in the winter, surfing, boogey boarding or just kicking back on the lanai to enjoy a rainbow, it just doesn't get any better than this 2 bedroom, 2 bathroom unit at Sands of Kahana. This...

    Pool Hot Tub

    $313 to $367/night

  13. HOUSE
    Sands Of Kahana 336

    Sands Of Kahana 336

    Kahana, HI

    Nestled on the pristine coastline of Kahana, located approximately halfway between Kaanapali and Kapalua, the beachfront condominium community known as the Sands of Kahana is the perfect family resort. With 2 bedrooms and two baths, this unit...

    Pool Hot Tub

    $313 to $367/night

  14. CONDOMINIUM
    Pacific Shores B102

    Pacific Shores B102

    Kihei, HI

    New Inventory!!! This beautifully decorated 3 bedroom condo is located in the heart of Kihei. This condo features a cozy and elegant living for your home away from home. Master bedroom has a Queen size bed, a queen in the 2nd bedroom and 2 twins in...

    Pool
    FREE CANCELLATION

    $313 to $531/night

  15. HOUSE
    Sands Of Kahana 373

    Sands Of Kahana 373

    Kahana, HI

    With spectacular views of Lanai, Molokai and the West Maui coastline, this ocean front two bedroom, two bath condominium offers unique photo opportunities. Create your perfect vacation memories with sunsets, surfers, sailboats, and whales....

    Pool Hot Tub

    $313 to $367/night

  16. CONDOMINIUM
    Maalaea Surf Unit #G-7

    Maalaea Surf Unit #G-7

    Kihei, Maui, HI

    Maalaea Surf Resort is an exceptional beachfront property located in North Kihei offering spectacular ocean views. This property consists of eight two story buildings spread out over five acres of immaculate tropical landscaping. It lies on the...

    Pool

    $313 to $526/night

  17. CONDOMINIUM
    Kaanapali Royal #N302

    Kaanapali Royal #N302

    Lahaina, HI

    New to program: Two story large vacation condo on the 3rd floor walking distance to Whaler's Village and Kaanapali Beach. (Stairs to entrance). King bed in the master suite upstairs, king bed in the guest bedroom downstairs and a queen sofa sleeper...

    Pool Hot Tub
    FREE CANCELLATION

    $310 to $922/night

  18. CONDOMINIUM
    Pili Mai Condominium 1-G

    Pili Mai Condominium 1-G

    Koloa, HI

    Brand New Luxury Condo at Pili Mai in Sunny Poipu! This is Kauai's Newest resort development! Located next to the Kiahuna Golf Course, Pili Mai offers Luxury living in peaceful, sunny Poipu! Condo 1-G is a 2 bedroom / 2 bath with a gorgeous Mountain...

    Pool
    FREE CANCELLATION

    $309 to $709/night

  19. HOUSE
    Pacific Edge Kona

    Pacific Edge Kona

    Kailua Kona, HI

    Pacific Edge Kona, a gracious oceanfront island style beach home! From the lanai of this waterfront vintage Hawaiian home see breaching humpback whales (when in season) and spinner dolphins frolic by day, spectacular sunsets at twilight and watch...

    $309 to $438/night

  20. HOUSE
    Kahana Sunset A3

    Kahana Sunset A3

    Kahana, HI

    Our ocean front home sits on a cliff directly in front of and above the ocean and only a single flight of stairs separates you from a secluded bay with white pristine sands. You can hear and see the ocean from the Master bedroom and living room...

    Pool

    $308 to $361/night

  21. VILLA
    Hanalei Bay Villas #16

    Hanalei Bay Villas #16

    Princeville, HI

    Hanalei Bay Villas #16-Amazing Hanalei Bay Views   Vacation in a lush tropical setting in beautiful Princeville with stunning panoramic ocean and mountain views seen from nearly every room. This vacation rental is a well designed two story town...

    $306 to $383/night

  22. HOUSE
    Hanalei Bay Villas #17

    Hanalei Bay Villas #17

    Princeville, HI

    Hanalei Bay Villas # 17-A townhouse close to St Regis Princeville New Remodel! A fun and casual bungalow with Golf Course, Ocean and Mountain Views. 3 bedrooms, 2.5 baths. This stand alone condominium is located close to the Princeville Hotel and...

    $306 to $383/night

  23. HOUSE
    Ka Hale

    Ka Hale

    Hanalei, HI

    Walking distance to beautiful Hanalei Bay or to quaint Hanalei Town, this one-story, 1,100 square foot vacation home offers you the best of both worlds. Surrounded by the peace and quiet of our neighborhood, relax on the back lanai to discover the...

    $306 to $383/night

  24. CONDOMINIUM
    Wailea Ekolu 1604

    Wailea Ekolu 1604

    Kihei, HI

    Wailea Ekolu is a beautiful 148-unit condominium development in luxurious Wailea, Maui. It is centrally located within a mile of The Shops at Wailea and many elegant restaurants such as Spago, Humble Market and Humuhumu. It is also a few minutes...

    Pool
    FREE CANCELLATION

    $306 to $1,398/night

  25. HOUSE
    Hale Hookaana

    Hale Hookaana

    Kailua Kona, HI

    Nicely manicured property with large grassy areas and fruit trees. Huge lanai, partially covered for relaxing and BBQ's, Main house consists of a gourmet kitchen with center Island, living room area with wrap around couch and large HD TV, dining...

    $304 to $609/night

  26. CONDOMINIUM
    South Kihei Condo A5-1

    South Kihei Condo A5-1

    Kihei, HI

    A5 is a townhouse unit on the second floor which offers our guest total privacy and is located beachfront on the property. This loft suite with 2 baths is very well furnished. Enjoy oceanfront outdoor living on your spacious private lanai (patio)...

    FREE CANCELLATION

    $304 to $467/night

  27. CONDOMINIUM
    South Kihei Condo H3-1

    South Kihei Condo H3-1

    Kihei, HI

    H3 is a conveniently located ground floor condo, just steps from our large pool and Sugar beach. This condo features a full kitchen and dining table. The master bedroom has a king sized bed. The large living room has expansive views and a...

    Pool
    FREE CANCELLATION

    $304 to $467/night

  28. COTTAGE
    Bamboo Beach Cottage

    Bamboo Beach Cottage

    Waimea, HI

    Bamboo Cottage is great for adventure seekers and lanai loungers. This double story 2 bedroom 3 bath home feels like true island style living. Directly across the street from the famous surf spot of Paniau Beach, Hawaii. Only a short walk to the...

    $303 to $478/night

  29. COTTAGE
    Paniau Surf Cottage 163

    Paniau Surf Cottage 163

    Waimea, HI

    Discover the pleasure of an authentic Old Hawaii Puako Beach House with modern day quality of granite counter tops, beautifully tiled floors throughout in the privacy of your very own cottage. The private outdoor garden shower offers highly desired...

    $303 to $545/night

  30. CONDOMINIUM
    Hanalei Bay Resort 6302

    Hanalei Bay Resort 6302

    Princeville, HI

    This unit has among the most extraordinary views in the entire resort. A top floor unit, the view from every room is exceptional, encompassing the entire expanse of the bay, from the mountains behind Hanalei to “Bali Hai” peak and the ocean...

    Pool Hot Tub

    $301 to $355/night