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:


Filter resultsGo Reset filtersReset Close
  1. VILLA
    3BD Hali'ipua Villa (108) at Four Seasons Resort Hualalai

    3BD Hali'ipua Villa (108) at Four Seasons Resort Hu...

    Kailua Kona, HI

    Among the newest additions to the exclusive Four Seasons Resort Hualalai, this ocean-view villa provides the perfect setting for a romantic getaway for two or a relaxing retreat to paradise for two couples. The villa boasts over 2,600 square feet of...

    Pool Hot Tub

    $1,056 to $3,293/night

  2. CONDOMINIUM
     Luxurious Oceanfront Condo on Molokai- Ka Hale Ola

    Luxurious Oceanfront Condo on Molokai- Ka Hale Ola

    Kaunakakai, HI

    You will feel so comfortable and "at home" in the condo that you will be reluctant to leave, but there are other wonderful experiences awaiting you on the grounds of Wavecrest. Wander through the lush tropical grounds, enjoy the fabulous pool right...

    Pool
    FREE CANCELLATION

    $158 to $191/night

  3. CONDOMINIUM
    Puako Beach Penthouse 405

    Puako Beach Penthouse 405

    Waimea, HI

    Fantastic panoramic ocean views. You can see the whales splashing their tales in the winter from the lanai! You can see the white sand at Hapuna Beach! Gorgeous sunsets, too! Watch the sunset while you BBQ and dine outdoors. This fabulous 3...

    Pool
    FREE CANCELLATION

    $322 to $435/night

  4. VILLA
    3BD Villas at Mauna Kea #39

    3BD Villas at Mauna Kea #39

    Kamuela, HI

    Relax in your own private pool and waterfall spa on a spacious deck while enjoying some of the best panoramic ocean, coastline, sunset, and Maui views in the entire Mauna Kea Resort. This exquisite luxury property, recently renovated and refreshed...

    Pool Hot Tub

    $1,220 to $3,856/night

  5. 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

    $1,703 to $4,290/night

  6. CONDOMINIUM
    Lovely Condo with Pool & Hot Tub! Waikoloa Hills Unit 903

    Lovely Condo with Pool & Hot Tub! Waikoloa Hills Uni...

    Waikoloa, HI

    Centrally located between the rolling green hills of Waimea and the Kohala Coast. Some of the Big Island's most beautiful beaches are located within a 15 minute drive. This condo is located in the Hills complex on Paniolo Ave., directly across from...

    Pool Hot Tub
    FREE CANCELLATION

    $177 to $225/night

  7. VILLA
    3BD Fairways Villa (116C) at Four Seasons Resort Hualalai

    3BD Fairways Villa (116C) at Four Seasons Resort Hualala...

    Kailua Kona, HI

    Make memories with family and friends in this spacious Waiulu Street ground floor villa, overlooking the 15th hole of the Jack Nicklaus Hualalai Golf Course with the Pacific Ocean and Mount Hualalai beyond. The home features an open floor plan, high...

    Pool Hot Tub

    $970 to $2,858/night

  8. TOWNHOUSE
    Poipu Crater

    Poipu Crater

    Koloa, HI

    Tucked away in the heart of an extinct volcano, Poipu Crater Resort offers lush tropical gardens, privacy and comfort. Perched on the upper rim of the crater, perfectly situated to enjoy sunny mornings and cool tradewinds in the afternoon. This...

    Pool

    $314 to $730/night

  9. HOUSE
    Hale Lokahi

    Hale Lokahi

    Waialua, HI

    Hale Lokahi - House of Peace and Serenity - This home is located in one of the best kept, secret neighborhoods on the north shore. Right on a white sand beach, this family-owned house is perfect for your vacation in paradise.. This 4 bedroom, 2...

    FREE CANCELLATION

    $683 to $992/night

  10. CONDOMINIUM
    Wai'ula'ula A102

    Wai'ula'ula A102

    Kamuela, HI

    Your visit to our vacation home will capture the essence of Hawaii. We are located along the Big Island’s exclusive golden Kohala Coast. Play golf on the emerald fairways of the renowned Mauna Kea Resort courses. Experience Kauna’oa and Hapuna,...

    Pool Hot Tub
    FREE CANCELLATION

    $618 to $1,236/night

  11. CONDOMINIUM
    Pohailani 128

    Pohailani 128

    Lahaina, HI

    Relax in this beautiful professionally decorated exquisite West Maui Condo.Lahaina*Kaanapali*KAHANA*Napili*Kapalua -West MAUI HOT SPOTSLocated in KAHANA (3 miles north of Kaanapali) in the center of West Maui and close to all the action. Ten minute...

    Pool

    $178 to $228/night

  12. CONDOMINIUM
    Banyan 1608-I Condominium

    Banyan 1608-I Condominium

    Honolulu, HI

    Free Parking, Central and Well equipped - Ocean View from Waikiki Banyan 1608-ILegally permitted rental ID : 90/TVU-1003 1990/NUC-0728 – NUC for Banyan 1608-1 ** Free Parking - Free WiFi - No Resort Fees !!** Classic Waikiki Banyan unit with...

    Pool
    FREE CANCELLATION

    $152 to $248/night

  13. 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

  14. VILLA
    Villa Cinco Resort at Kona Plantation Estates

    Villa Cinco Resort at Kona Plantation Estates

    Kailua Kona, HI

    This Villa is the owner’s primary residence under section 121 of IRC. The owners offer it for rent during limited periods. As such, it is Exempt from STVR rules, so it has no STVR registration #. TAT is TA-185-465-4464-01 . Villa operates in...

    Pool Hot Tub
    FREE CANCELLATION

    $759 to $762/night

  15. CONDOMINIUM
    Kapalua Bay Villa 23B3 Ocean Front

    Kapalua Bay Villa 23B3 Ocean Front

    Kapalua, HI

    This unique oceanfront villa is a whale watchers dream! Ocean views span the entire coastline! Uniquely positioned to include sunset views and situated on one of the most beautiful stretches of coastline in Maui. You will be captivated by the...

    Pool

    $581 to $969/night

  16. 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

  17. 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

  18. HOUSE
    Hale Nui

    Hale Nui

    Kaanapali, HI

    Thoughtfully designed with your comfort in mind, Hale Nui will exceed your expectations! After a long, arduous flight, each guest will feel embraced upon entering this exquisite, spacious home and everyone will immediately marvel at the panoramic...

    Pool Hot Tub
    FREE CANCELLATION

    $2,000 to $4,750/night

  19. CONDOMINIUM
    117

    117

    Kihei, HI

    Hale Kamaole is just a short walk from the Kamaole Beach III, where milder tides, full facilities and a lifeguard post makes for a low stress family atmosphere. Kamaole III is one of Maui’s favorite beaches and is great for snorkeling, a morning...

    Pool
    FREE CANCELLATION

    $188 to $270/night

  20. CONDOMINIUM
    Hale Kona Kai Ko Olina Beach Villa (O1105)

    Hale Kona Kai Ko Olina Beach Villa (O1105)

    Kapolei, HI

    Book with confidence! This vacation rental is a LEGAL Oahu vacation rental operating in a Resort Zoned District and is not affected by the passage of Bill 89.LIVE CALENDAR: If the calendar shows as available, the property IS available and can be...

    Pool Hot Tub

    $508 to $1,668/night

  21. CONDOMINIUM
    Aina Nalu A 201

    Aina Nalu A 201

    Lahaina, HI

    AINA NALU A-201 Welcomes you with Aloha...This unique condo in the heart of Old Lahaina Town is a perfect vacation spot!A-201 has been remodeled with a decor that speaks "ALOHA"Included in our fabulous price are many owner-supplied extras such...

    Pool Hot Tub
    FREE CANCELLATION

    $204 to $371/night

  22. CONDOMINIUM
    HiiLani-204

    HiiLani-204

    Lahaina, HI

    Book today and Fall in LOVE with "HiiLani" (In the arms of Heaven)...You will feel like you have gone back in time to the true Hawaiian experience in this condo just 15 FT from the water's edge!204 Pohailani Welcomes you with so much ALOHA..Included...

    Pool
    FREE CANCELLATION

    $175 to $264/night

  23. CONDOMINIUM
    Honua Kai 322

    Honua Kai 322

    Lahaina, HI

    This luxury Honua Kai one bedroom located in the 'Konea Tower' features everything you need to make your Hawaiian vacation truly enjoyable!We provide you with those extra amenities that make a difference, including comfortable beach chairs, beach...

    Pool Hot Tub
    FREE CANCELLATION

    $235 to $370/night

  24. CONDOMINIUM
    Papakea A307

    Papakea A307

    Lahaina, HI

    Highly upgraded West Maui Ka’anapali Papakea 1 bedroom, 1 full bathroom, third floor condo, 25 feet from the oceans edge. Watch the whales, sunsets, and the ocean from the kitchen, living room and lanai. Sleep to the sound of the waves. This condo...

    Pool Hot Tub

    $245 to $381/night

  25. 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

  26. CONDOMINIUM
    Kamahana 24

    Kamahana 24

    Princeville, HI

    This two bedroom, two full bath, upper floor end unit at the edge of the Kamahana complex features ocean, mountain, and golf course views from each room. As you end your day snuggled in the master bedroom's king bed, you'll fall asleep to the sound...

    Pool
    FREE CANCELLATION

    $183 to $214/night

  27. CONDOMINIUM
    Kaanapali Shores- 259- So close to the Beach!! 2b/2b

    Kaanapali Shores- 259- So close to the Beach!! 2b/2b

    Kaanapali, HI

    Best Ocean View Condo At Kaanapali Shores and JUST RENOVATED!This amazing condo has just been updated with new Luxury Vinyl Plank Flooring throughout and new modern furnishings including a great new Sofa/sleeper with brand new 6" mattress! (New...

    Pool Hot Tub

    $287 to $1,190/night

  28. CONDOMINIUM
    Papakea L108

    Papakea L108

    Lahaina, HI

    The condo is totally renovated and updated. From your private lanai you have a lovely area to sit and dine or just relax with nothing but the crystal blue ocean and the famous Maui sunsets in front, FRONT SEAT WHALE WATCHING from the lanai.Tile thru...

    Pool Hot Tub
    FREE CANCELLATION

    $206 to $841/night

  29. CONDOMINIUM
    Kaleialoha 309

    Kaleialoha 309

    Lahaina, HI

    Roof Sealing Construction Special!! $109 Aug. 26 - Sept. 2ndCome stay at the Kaleialoha Oceanfront Codominium!!This great direct oceanfront 1 bedroom, 1 bathroom condo offers the best of Hawaiian style living just a stones throw away from the...

    Pool
    FREE CANCELLATION

    $171 to $311/night

  30. CONDOMINIUM
    Papakea K306

    Papakea K306

    Lahaina, HI

    A beautifully updated kitchen allows for cooking family meals in, saving money for activities and adventures. In addition to the flat screen TV and dvd player in the living room, there is also a TV in the bedroom.. Bring your electronic equipment...

    Pool Hot Tub
    FREE CANCELLATION

    $161 to $688/night