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

Search results

  1. VILLA
    Hale Waiulu #150470

    Hale Waiulu #150470

    Kailua Kona, HI

    Our well-appointed home has everything you could possible need. Fresh, home grown mango, guava and finger lime for our guests to feast on . Enjoy the relaxing sound of the cascading rush of your private pool's waterfall. The lush golf green views of...

    Pool Hot Tub

    $2,022 to $6,318/night

  2. VILLA
    Makena Aloha Estate

    Makena Aloha Estate

    Lahaina, HI

    One of West Maui's most exclusive legally permitted rental properties, the Makena Aloha Estate offers exceptional ocean and mountain views, with gated exclusive privacy and seclusion. With 4,400 square feet of interior dwelling space, this...

    Pool

    $1,968 to $3,075/night

  3. HOUSE
    Papaua Estate

    Papaua Estate

    Lahaina, HI

    APPROVED MAUI SHORT TERM RENTAL HOUSE #STWM 2104/0003. You and your family and friends will love your stay here for a vacation filled with Aloha! If you are looking for location, luxury and Hawaiian life style, you have found it. Perhaps the most...

    Hot Tub
    FREE CANCELLATION

    $1,869 to $2,874/night

  4. VILLA
    Hualalai Resort Ocean Front Golf Villa 4202

    Hualalai Resort Ocean Front Golf Villa 4202

    Kailua Kona, HI

    Whale watch while listening to the breaking waves from the shoreline from the Master bedroom's private lanai with unobstructed ocean views! This beautifully appointed three bedroom villa has over 2,500 square feet of living area. Each of the three...

    FREE CANCELLATION

    $1,751 to $5,546/night

  5. VILLA
    Hualalai Resort Fairway Villa 110C

    Hualalai Resort Fairway Villa 110C

    Kailua Kona, HI

    This garden level 2 bedroom, 2 bath Fairway Villa overlooks the 15th Fairway of the Hualalai Golf Course with views of the ocean beyond. Located within the master-planned resort community of Hualalai, guests have the option of amenity use privileges...

    FREE CANCELLATION

    $934 to $2,335/night

  6. CONDOMINIUM
    Makena Surf Resort, #G-304

    Makena Surf Resort, #G-304

    Makena, HI

    Makena Surf Resort is a luxurious secluded beachfront condominium located in exclusive Makena. This gated community was developed with six 2 & 3 story buildings each offering sweeping views of the Pacific. The pristine and picturesque beach and...

    Pool

    $898 to $1,235/night

  7. HOUSE
    Kainoa

    Kainoa

    Hanalei, HI

    KAINOA:TVNCU-1227: TA#148-488-1920-01 Walk to Hanalei Bay or to Hanalei shops and restaurants This beautifully appointed 4 bedroom, (two master suites) and 3 bath home with Hawaiian and Asian flair. Hardwood floors extend out to the deck in a...

    Hot Tub

    $881 to $1,110/night

  8. HOUSE
    Ali'i Point 5

    Ali'i Point 5

    Kailua-Kona, HI

    Ali'i Point #5 is located at Ali'i Point, a private and gated community of 16 seaside homes with community pool and tennis court. Central A/C throughout. Main floor has living room, dining room, kitchen, half bath, and master king bedroom with en...

    Pool

    $668 to $846/night

  9. HOUSE
    Ainamalu Home 69-9242

    Ainamalu Home 69-9242

    Waikoloa Village, 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 is the newest resort community in the beautiful Waikoloa Beach Resort,...

    FREE CANCELLATION

    $649 to $896/night

  10. 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

  11. HOUSE
    Piko Nani

    Piko Nani

    Kailua Kona, HI

    Piko Nani “Hilltop Beauty” sits high on a knoll at the very top of O'oma Plantation, a newer subdivision of 19 estate-sized, 2-acre parcels. This quiet, supremely private home is perfect for a serene getaway. The elegantly finished interior of...

    Pool

    $555 to $759/night

  12. CONDOMINIUM
    Kaanapali Condominium 101

    Kaanapali Condominium 101

    Lahaina, HI

    This premium oceanfront Two Bedroom, Two Bath condo is conveniently located on the ground level. Master Bedroom has a King Bed with a private bathroom. Second Bedroom has a queen bed; and the living room has a queen sofa bed for the extra guests....

    Pool Hot Tub
    FREE CANCELLATION

    $516 to $620/night

  13. HOUSE
    Hale Aikane

    Hale Aikane

    Kailua Kona, HI

    Modern Hawaiian island style single level home located in a small private subdivision offers stunning panoramic ocean and sunset views providing for ultimate tranquility. Beautifully furnished in traditional Hawaiian island style décor, this...

    Pool

    $502 to $776/night

  14. CONDOMINIUM
    Wailea Elua Unit #0202

    Wailea Elua Unit #0202

    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

    $494 to $1,065/night

  15. CONDOMINIUM
    Papakea A404

    Papakea A404

    Lahaina, HI

    One of the nicest penthouse units at Papakea Resort. From your lanai and the master bedroom, watch the whales play and the honu (turtles) swim. The KING bed in master bedroom allows you to sleep to the sounds of the ocean just 25 feet away. The...

    Pool Hot Tub

    $491 to $707/night

  16. CONDOMINIUM
    Wai'ula'ula D201 Condominium

    Wai'ula'ula D201 Condominium

    Waimea, HI

    Welcome to Wai'ula'ula at the Mauna Kea Resort! Your vacation will truly be one to remember in this beautifully decorated condominium in the gated community of Wai'ula'ula, located on the Hapuna Golf Course. This recently built luxury development...

    Pool
    FREE CANCELLATION

    $481 to $1,174/night

  17. CONDOMINIUM
    Wailea Elua Unit #0702

    Wailea Elua Unit #0702

    Wailea, HI

    About this condo: Wailea Elua Village #702 is a spacious two bedroom, two bath oceanview condo with a king bed in the master bedroom, 2 twins in the guest bedroom and a sofa sleeper in the living room. It's located in the oceanfront area of the...

    Pool

    $448 to $953/night

  18. CONDOMINIUM
    Hali'i Kai at Waikoloa Beach Resort

    Hali'i Kai at Waikoloa Beach Resort

    Kailua Kona, HI

    On the sun-drenched Kohala coast on the Big Island of Hawaii, the elements have come together to create a place like no other.  It is at this point of convergence that we have chosen to situate our residential community Hali’i Kai at Waikoloa. ...

    Pool

    $444 to $689/night

  19. CONDOMINIUM
    Puamana 153-4

    Puamana 153-4

    Lahaina, HI

    Walk to the Beach and Downtown Lahaina. Puamana is the perfect setting for families, romantic getaways, or anniversary celebrations. Puamana is a gated 30 acre ocean front community of low rise high quality attached homes nestled along the sunny...

    Pool
    FREE CANCELLATION

    $438 to $999/night

  20. CONDOMINIUM
    Honua Kai 346

    Honua Kai 346

    Lahaina, HI

    We invite you to stay in our gorgeous ocean view 1 bedroom/1 bathroom condo at Honua Kai! Enjoy the sparkling blue water views from the open lanai and the bedroom, bringing a total sense of relaxation to your time in Maui. Honua Kai 346 is one of...

    Pool Hot Tub
    FREE CANCELLATION

    $427 to $1,044/night

  21. CONDOMINIUM
    Honua Kai 520

    Honua Kai 520

    Lahaina, HI

    What sounds better than waking up to a hot cup of delicious coffee on a lanai that opens up to sweeping views of the majestic West Maui mountains? We invite you to indulge in the authentic Maui lifestyle, making our Honua Kai 520K your home away...

    Pool Hot Tub
    FREE CANCELLATION

    $427 to $1,169/night

  22. HOUSE
    Leilani Hale

    Leilani Hale

    Kailua Kona, HI

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

    Pool

    $425 to $729/night

  23. CONDOMINIUM
    Hanalei Bay Resort 6301-2

    Hanalei Bay Resort 6301-2

    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

    $422 to $482/night

  24. CONDOMINIUM
    Mauna Lani Terrace D201

    Mauna Lani Terrace D201

    Kamuela, HI

    Mauna lani terrace#D-201 Beachfront Location, Breathtaking Views, Best Value. Amazing new property booking specials for last minute vacancies. Brand new ownership at one of the finest properties that the Mauna Lani Terrace has to offer. Enjoy...

    Pool Hot Tub
    FREE CANCELLATION

    $419 to $759/night

  25. CONDOMINIUM
    Palms at Wailea #1503

    Palms at Wailea #1503

    Kihei, 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
    FREE CANCELLATION

    $418 to $585/night

  26. CONDOMINIUM
    Grand Champions #72

    Grand Champions #72

    Wailea, HI

    The nearby Ulua and Mokapu Beaches are a quick drive down the hill from the Grand Champions Villas in Wailea. The complex is surrounded by lovely tropical gardens. It is located in the exclusive Wailea Resort. The complex offers two swimming pools,...

    Pool
    FREE CANCELLATION

    $406 to $696/night

  27. HOUSE
    Kahana Sunset A4

    Kahana Sunset A4

    Kahana, HI

    Incredible townhouse condominium with the perfect oceanfront location right next to one of Maui’s most beautiful and safest reef-protected beaches. This beautiful townhouse condominium has just undergone a complete designer remodel. The remodel...

    Pool

    $404 to $457/night

  28. CONDOMINIUM
    Hanalei Colony Resort I1

    Hanalei Colony Resort I1

    Hanalei, HI

    Hanalei Colony Resort I1 is unique among north shore Kauai condo complexes. It's directly on the path to follow, just take a few steps and you're on the sand. You can also take advantage of the restaurant and spa onsite, or prepare your own food in...

    Pool

    $397 to $520/night

  29. COTTAGE
    Plantation Cottage

    Plantation Cottage

    Hanalei, HI

    PLANTATION COTTAGE: TVNC-1104: TA#154-325-1968-01 Charming 1 bedroom, 1 bath, Hawaiian style cottage. A Private and Romantic Location. Palm trees surround the expansive yard. Very serene setting. High Speed WiFi Internet Service. A Weber Charcoal...

    $383 to $475/night

  30. CONDOMINIUM
    Hale Mahina Unit #A-201

    Hale Mahina Unit #A-201

    Lahaina, HI

    Hale Mahina Beach Resort, West Maui Hale Mahina (House of the Moon) is located on the world famous West Coast of Maui adjacent to the West Maui Mountains, nestled between Kaanapali and Kapalua in the charming oceanfront town of Honokowai. Hale...

    $358 to $560/night