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
  1. CONDOMINIUM
    Kaleialoha #215

    Kaleialoha #215

    Lahaina, HI

    Nice corner unit offers privacy and expanded views. Cal King bed, New carpet and appliances. AC, washer/dryer, free wireless internet, local phone and basic cable.Flat screen TV. All basic amenities included including linens, beach supplies and...

    Pool
    FREE CANCELLATION

    $183 to $325/night

  2. CONDOMINIUM
    Hale Ikena Ko Olina Beach Villa (O1406)

    Hale Ikena Ko Olina Beach Villa (O1406)

    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

    $432 to $1,384/night

  3. CONDOMINIUM
    3BR w/ Infinity Pool & Spa, Near Snorkeling Beach

    3BR w/ Infinity Pool & Spa, Near Snorkeling Beach

    Kailua Kona, HI

    Set right across the street from Kahalu’u Beach, this 3BR/2BA condo is within steps of one of the best beaches in Hawaii for surfing. Your prime locale is also close to Kona Town and Keauhou.Perched on the second-floor, this corner unit boasts...

    Pool Hot Tub
    FREE CANCELLATION

    $216 to $493/night

  4. CONDOMINIUM
    Honua kai- Luana Garden Villa 3C

    Honua kai- Luana Garden Villa 3C

    Kaanapali, HI

    Luana Garden Villas is the newest offering at the beautiful Honua kai Resort & Spa.  These spacious 3 bedroom Villas are located in 3 private enclaves and include large lanai's, private outdoor kitchens and a private garage. Each Enclave boasts a...

    Pool Hot Tub

    $844 to $2,843/night

  5. CONDOMINIUM
    Sugar Beach Resort PH 27

    Sugar Beach Resort PH 27

    Kihei, HI

    Penthouse unit #27 is is an extremely well maintained, top-floor unit with breathtaking views of the Pacific and neighbor islands. You can whale watch from the private lanai, when the humpback whales return to the warm tropical waters around Maui....

    Pool Hot Tub
    FREE CANCELLATION

    $174 to $290/night

  6. CONDOMINIUM
    Hale Ka Wailele Malu Ko Olina Beach Villa (O226)

    Hale Ka Wailele Malu Ko Olina Beach Villa (O226)

    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

  7. CONDOMINIUM
    Hoyochi Nikko #102

    Hoyochi Nikko #102

    Lahaina, HI

    Large one bedroom, custom tile throughout, glass block shower, new appliances and new cabinetry all make for a beautiful unit that flows from the living room onto the lanai and oceanfront garden area. King size bed allows total comfort. The lanai...

    Pool
    FREE CANCELLATION

    $240 to $330/night

  8. HOUSE
    Junior Suite Oceanfront #303

    Junior Suite Oceanfront #303

    Lahaina, HI

    Jr. Suite - Bright and Easy Island Style. Queen bed (no sofa bed), tiled entryway, Flat Screen TV, light furnishings throughout. Put away your groceries and make yourself at home. Enjoy your private lanai with your favorite beverage. Watch the...

    Pool Hot Tub
    FREE CANCELLATION

    $278 to $341/night

  9. CONDOMINIUM
    Islander on the Beach 259

    Islander on the Beach 259

    Kapaa, HI

    Special discount for open August dates! Air-conditioned, ocean view, right on the beach, pool-side bar and grill, two minute walk to the Coconut Marketplace or Lava Lava Beach Club. This upgraded studio with kitchenette is absolutely perfect!...

    Pool
    FREE CANCELLATION

    $170/night

  10. CONDOMINIUM
    D10-Beachfront Loft Suite

    D10-Beachfront Loft Suite

    Kihei, HI

    Ma'alaea Surf, Unit D10 is a townhouse unit on the second floor which offers our guest total privacy and is located beach front on the property. This loft suite with 2 baths is very well furnished.Enjoy ocean front outdoor living on your spacious...

    Pool
    FREE CANCELLATION

    $304 to $467/night

  11. CONDOMINIUM
    D4-1 Bedroom Beachfront

    D4-1 Bedroom Beachfront

    Kihei, HI

    Ma'alaea Surf, Unit D4 - Deluxe in every sense. D4 is an ideally located ground floor unit, approximately 5 steps from the white sandy beach. This luxurious unit features a contemporary kitchen. Enjoy the ocean views and Maui's majestic sunset from...

    Pool
    FREE CANCELLATION

    $304 to $467/night

  12. CONDOMINIUM
    Waiohuli Beach Hale #D-220

    Waiohuli Beach Hale #D-220

    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

  13. HOUSE
    Junior Suite Oceanfront #706

    Junior Suite Oceanfront #706

    Kaanapali, HI

    Our Junior Suite is spacious and well-appointed with a Queen Bed; as well as a sofa bed for the occasional guest. There are seating arrangements for relaxing and dining. You will find plenty of space to store your clothing and personal items. The...

    Pool Hot Tub
    FREE CANCELLATION

    $278 to $341/night

  14. CONDOMINIUM
    Sealodge A6

    Sealodge A6

    Princeville, HI

    Enjoy a picnic or snorkel trip just steps from your door. This Kauai vacation rental is a great choice for a those in search of more seclusion and peaceful surroundings. There are oceanfront views from everywhere in this condo -- with great whale...

    Pool

    $235 to $301/night

  15. HOUSE
    Kona Bay Bliss

    Kona Bay Bliss

    Kailua Kona, HI

    This incredible home is secluded in a 24 hour guard gated oceanfront community, yet is close to all that Kona has to offer. It is located just a short walk from the classic old Hawaiian town of Kailua and the start/finish of the Ironman.In all of...

    Pool Hot Tub

    $1,343 to $2,014/night

  16. CONDOMINIUM
    Kaleialoha 205

    Kaleialoha 205

    Lahaina, HI

    A direct Beach/Oceanfront condo with an amazing view. Beach and ocean access for swimming, snorkeling, whale watching and relaxing in the sun.You can't get closer to the ocean than this unless you're on a boat. Watch the whales December through...

    Pool
    FREE CANCELLATION

    $186 to $331/night

  17. CONDOMINIUM
    Valley Isle 110

    Valley Isle 110

    Lahaina, HI

    ~Book today and Fall in LOVE with 110 Valley iIsle The"Aloha House"You will feel like you have gone back in time to the true Hawaiian experience in this condo just STEPS from the water's edge!110 Valley Isle Welcomes you with so muchSome of the many...

    Pool
    FREE CANCELLATION

    $187 to $312/night

  18. CONDOMINIUM
    G5-1 Bedroom Oceanfront

    G5-1 Bedroom Oceanfront

    Kihei, HI

    Ma'alaea Surf, Unit G5 - Just steps from one of Maui’s longest white sand beaches, recently renovated G-5 has all the amenities of a luxury resort. Centrally located between the tourists centers of Lahaina/Kapalua and Wailea/Makena, Maalaea Surf...

    Pool
    FREE CANCELLATION

    $259 to $428/night

  19. CONDOMINIUM
    Hale Ono Loa 214

    Hale Ono Loa 214

    Lahaina, HI

    Beautiful Views – Currently Being Remodeled!Enjoy this West Maui Ocean Front Resort with lush grounds which includes a pool, lounge area, shuffleboard, picnic area, BBQ’s. Relax on a Lanai and enjoying sunset dinners and beautiful views.This...

    Pool
    FREE CANCELLATION

    $200 to $513/night

  20. CONDOMINIUM
    Puu Poa 410

    Puu Poa 410

    Princeville, HI

    The Puu Poas are known for their distinctive, contemporary architecture and their amazing ocean and Bali Hai views. Puu Poa 410 is located up on the bluff of Princeville and is conveniently located near the St. Regis Hotel and just down the street...

    Pool

    $392 to $512/night

  21. CONDOMINIUM
    Sealodge E9

    Sealodge E9

    Princeville, HI

    ONE OF THE MOST SPECTACULAR VIEWS IN ALL OF KAUAI! This premium (yet affordable) Kauai vacation rental is perched on a cliff with expansive oceanfront views of the Pacific Ocean and the Kauai coastline. From your lanai or living area you may see...

    Pool

    $235 to $301/night

  22. CONDOMINIUM
    Alii Kai 5103

    Alii Kai 5103

    Princeville, HI

    This Alii Kai condo opens its sliding glass back door onto a grassy knoll on which you have an unobstructed view of the majestic Kauai coastal panorama. Wake up to the gentle northeastern ocean breezy skies and step out onto the lawn overlooking the...

    Pool

    $283 to $331/night

  23. CONDOMINIUM
    Sealodge G3

    Sealodge G3

    Princeville, HI

    Special discount for open August dates! Sealodge G3: Unbelievable oceanfront views from this intimate ground floor hideaway with updated interior and King sized bed! One bedroom, one bathroom, with private oceanfront lanai to enjoy the view and...

    Pool
    FREE CANCELLATION

    $226 to $257/night

  24. CONDOMINIUM
    Cliffs 9201

    Cliffs 9201

    Princeville, HI

    Enjoy the cooling trade winds while watching the dolphins and whales (depending on season) frolicking in front of you as you are lounging on your private oceanfront lanai (patio). This very comfortable condo provides spectacular sunrises and sunsets...

    Pool Hot Tub

    $253 to $271/night

  25. CONDOMINIUM
    A1-2 Bedroom Beachfront

    A1-2 Bedroom Beachfront

    Kihei, HI

    Maalaea Surf, Unit A1 is a conveniently located ground floor unit, direct beachfront, just steps away from the beach. This unit features an updated kitchen with convection oven, dishwasher and large refrigerator. The master bedroom has twin beds....

    Pool
    FREE CANCELLATION

    $416 to $664/night

  26. CONDOMINIUM
    Sealodge E10

    Sealodge E10

    Princeville, HI

    Very private top floor ocean front location. Sealodge E10 is the perfect choice for a honeymoon. All of the north shore's great beaches and attractions are conveniently close, and there's a beach path onsite, but you'll be perfectly happy to stay...

    Pool
    FREE CANCELLATION

    $226 to $275/night

  27. CONDOMINIUM
    Paki Maui 422

    Paki Maui 422

    Lahaina, HI

    Ocean Front 2 Bedroom/2 Bathrooms/Sleeps: 4 Persons Queen, Queen, No Sofa Bed, No A/C A great oceanfront value on the Kaanapali coast. Beach Towels Provided! Panoramic oceanront and shoreline views await you fron one of the most desirable units in...

    Pool

    $298 to $354/night

  28. CONDOMINIUM
    Alii Kai 4103

    Alii Kai 4103

    Princeville, HI

    Enjoy panoramic ocean views from the living room and both bedrooms of this spacious condo in Princeville. Ground-floor unit includes fully equipped kitchen with brand new custom cabinets and washer/dryer, dining area, king bed in master bedroom,...

    Pool

    $283 to $331/night

  29. APARTMENT
    Kahana Reef 201

    Kahana Reef 201

    Lahaina, HI

    Whales and dolphins frolic in our clear, warm water and you can watch surfers, windsurfers, and kite surfers playing in our waves. The occasional sea turtle (Honu) pops his head up for a quick peek at our visitors. Snorkeling and kayaking are also a...

    Pool
    FREE CANCELLATION

    $169/night

  30. CONDOMINIUM
    Banyan Tree 200

    Banyan Tree 200

    Kailua Kona, HI

    This island home is so close to the ocean you might get wet! Enjoy a cup of famous Kona Coffee and soak up the amazing views while watching, dolphins, whales (when in season) or surfers catching waves all the while listening to the sounds of the...

    Pool Hot Tub

    $210 to $315/night