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
    Ali'i Kai 6102

    Ali'i Kai 6102

    Princeville, HI

    Enjoy oceanfront views from every window in this spacious, updated 2br/2ba condo. Unique location in a single-story building, so you have all the advantages of a ground floor unit, but no other condos above you. A variety of beach gear is...

    Pool
    FREE CANCELLATION

    $152 to $539/night

  2. CONDOMINIUM
    Poipu Shores B201

    Poipu Shores B201

    Koloa, HI

    This newly remodeled 2br/1.5ba has one of the best oceanfront views on the island. With full kitchen, washer/dryer, phone, and free wifi, you'll have all the comforts of home at Poipu Shores B201...plus walk to Brennecke's Beach and the Poipu Beach...

    Pool
    FREE CANCELLATION

    $402 to $1,054/night

  3. CONDOMINIUM
    Puu Poa 401

    Puu Poa 401

    Princeville, HI

    Romantic, AIR CONDITIONED (a/c in living room and master bedroom), totally private, luxury penthouse that guarantees an unequaled experience! The epitome of gracious living, capturing panoramic views of the azure ocean and Bali Hai. The best of the...

    Pool
    FREE CANCELLATION

    $269 to $1,018/night

  4. CONDOMINIUM
    Villas of Kamalii 44

    Villas of Kamalii 44

    Princeville, HI

    Enjoy comfort and luxury in this three bedroom/three bathroom townhouse with spectacular mountain and waterfall views, heated salt water pool, and jacuzzi. Located in a gated community adjacent to the Makai golf course, Villas of Kamalii 44 boasts a...

    Pool Hot Tub
    FREE CANCELLATION

    $240 to $866/night

  5. CONDOMINIUM
    Ali'i Kai 7204

    Ali'i Kai 7204

    Princeville, HI

    Great family vacation spot right on the bluff. Beautiful natural Koa Wood upgrades create a feeling of quality and Hawaiian comfort. Great details! Granite countertops, bamboo floors. Comfortable furniture to relax your body and ocean sounds and...

    Pool
    FREE CANCELLATION

    $161 to $514/night

  6. CONDOMINIUM
    Ali'i Kai 4303

    Ali'i Kai 4303

    Princeville, HI

    A Million Dollar View! Take in the phenomenal Hawaiian wildlife from this 20 ft. lanai - whales, spinner dolphins and more. View the ~180 degree coastline from the beacon of the Kilauea lighthouse to sunsets over Bali Hai on the West. With the...

    Pool
    FREE CANCELLATION

    $124 to $514/night

  7. CONDOMINIUM
    Nohonani 405

    Nohonani 405

    Lahaina, HI

    Nohonani 405 is a beautiful two bedroom one and a half bath unit on the fourth floor, with vaulted ceilings and a breathtaking ocean view. Ocean views can be seen from the kitchen, dining areas, living room and master bedroom. As with all the...

    Pool
    FREE CANCELLATION

    $274 to $403/night

  8. CONDOMINIUM
    WPH1507 THTC-CTOQ(XS)-STALL-ACH

    WPH1507 THTC-CTOQ(XS)-STALL-ACH

    Honolulu, HI

    This privately owned 1 bedroom condo fully furnished and fully equipped providing a private "Home Away From Home" experience. This one bedroom suite is prefect for the traveler who wants to be in a full apartment in the center of Waikiki with FREE...

    Pool
    FREE CANCELLATION

    $1,249/night

  9. CONDOMINIUM
    Menehune Shores Unit #427

    Menehune Shores Unit #427

    Maui, HI

    A note from the owner: Our unit was completely remodeled in 2006. It is great for families or couples traveling together. This ocean front condo has spectacular outer island views. The condo is well appointed with all you will need for a comfortable...

    Pool

    $246 to $336/night

  10. CONDOMINIUM
    Wailea Grand Champion, #148

    Wailea Grand Champion, #148

    Wailea, HI

    Wailea Grand Champions Golf Villas is a modern property located between the Wailea Blue Golf Course and the Wailea Tennis Club. This quiet low density development consists of twenty mostly two-story buildings set amongst lush tropical landscaping...

    Pool Hot Tub

    $201 to $549/night

  11. HOUSE
    Indo Lotus Beach House

    Indo Lotus Beach House

    Wailea, HI

    The Indo Lotus Beach House is one of the few vacation homes on Maui that has a legal grandfathered rental history, combined with a beachfront location. Set on Kamaole One Beach at the 'Charley Young' end, Indo Lotus has direct access to a popular...

    Hot Tub

    $1,458 to $2,694/night

  12. CONDOMINIUM
    Palm Leaf

    Palm Leaf

    Kamuela, HI

    Find outdoor living at its finest at the 2-bedroom, 2.5-bath Kulalani 104 at Mauna Lani. Several spacious, private lanais offer lush tropical views, including one with al fresco dining and a luxury outdoor kitchen with built-in stainless BBQ. With...

    Pool Hot Tub

    $238 to $598/night

  13. VILLA
    Hale Waiulu

    Hale Waiulu

    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...

    Pool Hot Tub

    $1,917 to $5,992/night

  14. CONDOMINIUM
    Wailea Ekolu #103

    Wailea Ekolu #103

    Wailea, HI

    Wailea Ekolu has several lovely pool areas as well as a large pavilion area for larger groups. There are also additional barbecue and picnic areas on the grounds with panoramic views of the ocean and the sunsets. The beautiful Mokapu and Ulua...

    Pool
    FREE CANCELLATION

    $240 to $521/night

  15. CONDOMINIUM
    Waiohuli Beach Hale #A-201

    Waiohuli Beach Hale #A-201

    Kihei, HI

    Gorgeous Remodeled Oceanfront Kihei Condo – 2BR You can’t do better than this! Not only does this beautifully renovated second-floor unit have an unobstructed ocean view but the quality of the complex and its location cannot be beat. The ocean...

    Pool
    FREE CANCELLATION

    $208 to $347/night

  16. CONDOMINIUM
    Palms at Wailea #1507

    Palms at Wailea #1507

    Wailea, HI

    Unit 1507 is a spacious, beautiful condo with a gorgeous ocean view located in the desirable inner courtyard just a short stroll to the picturesque pool, all without climbing steep stairs. Fully air conditioned with a 3 zone split system, this condo...

    Pool Hot Tub
    FREE CANCELLATION

    $405 to $579/night

  17. CONDOMINIUM
    Maui Kamaole #D-107

    Maui Kamaole #D-107

    Kihei, HI

    Kamaole Beach #3 is just across from the upscale Maui Kamaole. This property features lush tropical landscaping, two gorgeous pool areas with hot tubs and water features. There are gas grills peppered throughout the property and tennis courts...

    Pool Hot Tub
    FREE CANCELLATION

    $174 to $238/night

  18. CONDOMINIUM
    127

    127

    Kihei, HI

    This super-modern ground floor condo has been completely remodeled for your comfort and style. Kitchen has beautiful wood cabinets with granite counter tops for easy clean-up. Granite top is used as a dining set with tall comfortable rattan chairs...

    Pool
    FREE CANCELLATION

    $188 to $270/night

  19. CONDOMINIUM
    Hale Leilani Ko Olina Beach Villa (B708)

    Hale Leilani Ko Olina Beach Villa (B708)

    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 $1,384/night

  20. CONDOMINIUM
    Hale Makai Ko Olina Beach Villa (O805)

    Hale Makai Ko Olina Beach Villa (O805)

    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

    $594 to $1,668/night

  21. CONDOMINIUM
    Hale Uliuli Lani Ko Olina Beach Villa (O1602)

    Hale Uliuli Lani Ko Olina Beach Villa (O1602)

    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

    $571 to $1,668/night

  22. CONDOMINIUM
    Hale Koa Ko Olina Beach Villa (O222)

    Hale Koa Ko Olina Beach Villa (O222)

    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...

    $531 to $1,500/night

  23. CONDOMINIUM
    2BR w/ 3 Lanais & 2 Pools, Walk to Beach

    2BR w/ 3 Lanais & 2 Pools, Walk to Beach

    Kihei, HI

    Set on a hilltop overlooking the Pacific, this beautiful 2BR/2BA offers a private beachside getaway. Your spacious condo boasts 1,279 square feet across of living space on two levels, vaulted ceilings, upgraded finishes, tropical furniture, and...

    Pool Hot Tub
    FREE CANCELLATION

    $206 to $494/night

  24. CONDOMINIUM
    Waikiki Banyan Tower 1 Suite 2210

    Waikiki Banyan Tower 1 Suite 2210

    Honolulu, HI

    Deluxe High level condo with Ocean View Enjoy a fully-equipped kitchen and comfortable seating in the living room. Kitchen includes standard kitchen wares and there is plenty of counter space and an island with seating for four people. Sleeping...

    Pool Hot Tub

    $191 to $293/night

  25. CONDOMINIUM
    Waikiki Banyan Tower 2 Suite 807

    Waikiki Banyan Tower 2 Suite 807

    Honolulu, HI

    Deluxe Mountain View Condo, Free parking & WiFi Upgraded Waikiki Banyan condo at an affordable rate. Enjoy paradise in this Mountain View Waikiki Banyan condo suite with 2 high-end luxury queen sized mattresses! Only one block from world famous...

    Pool Hot Tub

    $180 to $236/night

  26. APARTMENT
    WS2105 RFRF-CTOQ(RM)-00-ACH

    WS2105 RFRF-CTOQ(RM)-00-ACH

    Honolulu, HI

    Let us welcome you to this Completely Remodeled 1 Bedroom Suite "Majestic Views that will Awe you" in the Waikiki Sunset. World Famous White Sandy Beaches only one block away, Relax and enjoy all the fabulous amenities, Sapphire Blue Tiled Pool,...

    Pool
    FREE CANCELLATION

    $199 to $311/night

  27. CONDOMINIUM
    Hoyochi Nikko #109

    Hoyochi Nikko #109

    Lahaina, HI

    One bedroom condo located in beautiful west Maui. For those wishing additional solitude, this is an end unit with a new queen bed and bedroom air conditioning. All units are fully equipped with Cable TV, DVD, CD player, washer/dryer, and...

    Pool
    FREE CANCELLATION

    $201 to $296/night

  28. CONDOMINIUM
    Pikake A-4

    Pikake A-4

    Lahaina, HI

    An incredibly comfortable unit! This renovated one bedroom unit fronts directly on a beautiful white sand beach. You'll have just enough lawn area to stretch out and shake the sand off before stepping directly into your beautiful ocean side living...

    FREE CANCELLATION

    $161 to $308/night

  29. CONDOMINIUM
    Sugar Beach Resort, #418

    Sugar Beach Resort, #418

    Kihei, HI

    Sugar Beach Resort is the Winner of Building of the Year and Manager of the Year Awards from the Institute of Real Estate Management (IREM®) Sugar Beach Resort is a tranquil beachfront condominium resort located in North Kihei offering sweeping...

    Pool

    $190 to $387/night

  30. CONDOMINIUM
    Papakea L106

    Papakea L106

    Lahaina, HI

    Highly upgraded West Maui Kaanapali Papakea 2 bedroom, 2 full bathrooms, ground 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

    $400 to $491/night