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. HOUSE
    Hale Pua

    Hale Pua

    Kailua Kona, HI

    Hale Pua (“House of Flowers”) now features AC as an option in all of its sleeping areas: five king bedrooms, one bunkroom with four twin beds and game room with queen sofabed. This special home is maybe the only 6 bed/6 full bath oceanfront...

    Pool

    $2,212 to $3,444/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
    Rainbow Hale Estate

    Rainbow Hale Estate

    Lahaina, HI

    Maui's Premier Vacation Home! Rainbow Hale Estate Kaanapali! Family Retreat, Private Honeymoon Retreat! Surrounded by 5 acres of Maui tropical plantation, lies a BRAND NEW spectacular estate you've always dreamed of, with the lifestyle you've always...

    Pool

    $1,661 to $2,429/night

  4. CONDOMINIUM
    O-1202: Hale Pumehana Ko Olina Beach Villa

    O-1202: Hale Pumehana Ko Olina Beach Villa

    Kapolei, HI

    This 3 BD, 2.5 BA luxury Penthouse on the 12th floor of the Ocean Tower has stunning direct ocean views, was fully re-decorated by a professional interior designer in early 2015 (NEW paint, furnishings, original artwork, built-in closets,...

    Pool

    $740 to $1,668/night

  5. CONDOMINIUM
    Wailea Elua #2204

    Wailea Elua #2204

    Wailea, Maui, HI

    You will immediately sense that the fabulous Maui vacation you have been looking forward to has begun when you step into this completely remodeled 2 bedroom, 2 bath condo located on one of the best locations in the Wailea Elua Village. From our...

    Pool

    $724 to $1,065/night

  6. CONDOMINIUM
    B-109: Hale Nani Ikena Kai Ko Olina Beach Villa

    B-109: Hale Nani Ikena Kai Ko Olina Beach Villa

    Kapolei, HI

    The Hale Nani Ikena Kai beach villa at Ko Olina offers exactly what its name suggests; a home with a “Beautiful Ocean View”. Spectacular direct whitewater ocean and beach views will be what greets you at this upscale, luxurious ground floor...

    Pool Hot Tub

    $682 to $2,016/night

  7. VILLA
    Kapalua Bay Villa 29B2

    Kapalua Bay Villa 29B2

    Lahaina, HI

    Kapalua Bay Villa at its best! This oceanfront property was built to enjoy the casual lifestyle of Kapalua. Beautiful views and the sound of the blue pacific greet you from every part of this unbelievable property. This spacious two bedroom, three...

    Pool

    $610 to $1,118/night

  8. CONDOMINIUM
    Wailea Elua #2303

    Wailea Elua #2303

    Kihei, HI

    Wailea Elua is the premier ocean front property in Wailea. A gated property situated right on picturesque Ulua Beach, it has one of the best locations in Wailea. There are miles of spectacular walking paths that follow the ocean. In addition, the...

    Pool Hot Tub
    FREE CANCELLATION

    $609 to $1,073/night

  9. 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

  10. CONDOMINIUM
    O-226: Hale Ka Wailele Malu Ko Olina Beach Villa

    O-226: Hale Ka Wailele Malu Ko Olina Beach Villa

    Kapolei, HI

    Hale Ka Wailele Malu is one of the most unique and desirable Beach Villas in all of Ko'Olina. The large (1,650 sq ft) 3 bedroom, 3 bathroom, 2nd floor, ocean-facing Beach Villa is one of only four Villas (out of the 247) that fronts the soothing and...

    Pool Hot Tub

    $543 to $1,668/night

  11. 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

  12. CONDOMINIUM
    Waterfall House

    Waterfall House

    Kailua-Kona, HI

    Beautiful high end home with views directly to the ocean below. Have your own private retreat within a secure, gated community in an expansive open home. Stay in perhaps one of the most unique homes in Hawaii where it rains into the house, filling...

    Pool Hot Tub

    $437 to $1,717/night

  13. CONDOMINIUM
    Papakea Condo Unit D402

    Papakea Condo Unit D402

    Kaanapali, HI

    Ocean views in North Ka'anapali. This 4th floor condo features 2 bedrooms with bathrooms downstairs plus a loft bedroom, with 2 twins beds, and a half bathroom. The living room has a 37" LCD HDTV & Blu-ray player with property HD signal to match....

    Pool
    FREE CANCELLATION

    $406 to $986/night

  14. 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

  15. 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

    $400 to $491/night

  16. CONDOMINIUM
    Lokelani A203

    Lokelani A203

    Lahaina, HI

    Lokelani is a gorgeous 2 -floor oceanfront condo that has been completed renovated. It has 2 bedrooms and 2 full bathrooms. The master suite has a king bed and it's own private lani, the second bedroom has 2 twins that can be converted into a King...

    Pool
    FREE CANCELLATION

    $375 to $1,350/night

  17. CONDOMINIUM
    Kihei Surfside 412

    Kihei Surfside 412

    Kihei, HI

    Completely remodeled condo, from top to bottom. Nothing has been overlooked in this beautifully appointed one bedroom Ocean Front condo. This stunning renovation, features top of the line materials including granite counter tops in kitchen and...

    Pool
    FREE CANCELLATION

    $363 to $485/night

  18. CONDOMINIUM
    Honua Kai #316

    Honua Kai #316

    Lahaina, HI

    This couples and family friendly resort is located on the exquisite Kaanapali Beach!  Enjoy  extraordinary dining, shopping, and top of the line amenities at our 4 diamond property. The resort has 3 large pools, 5 hot tubs and a spa! The FORMAL...

    Pool Hot Tub
    FREE CANCELLATION

    $359 to $474/night

  19. CONDOMINIUM
    Royal Kahana Unit #911

    Royal Kahana Unit #911

    Kahana, HI

    Stunning ocean front views from the 9th floor in this beautifully remodeled & tastefully furnished condo on Kahana Bay. A large wrap-around lanai, accessible from the living room and master bedroom, adds to the view. In addition to the HD TV &...

    Pool
    FREE CANCELLATION

    $354 to $1,133/night

  20. CONDOMINIUM
    Maui Hill #I-99

    Maui Hill #I-99

    Kihei, HI

    Maui Hill Resort is located minutes from the premier resort area of Wailea. Keawakapu and Kamaole beaches are within walking distance. The resort features a swimming pool, barbecue grills, tennis, a putting green, and shuffleboard. Enjoy free...

    Pool Hot Tub
    FREE CANCELLATION

    $347 to $695/night

  21. CONDOMINIUM
    Papakea Unit #A201 Condo

    Papakea Unit #A201 Condo

    Lahaina, HI

    2nd floor corner unit with AMAZING ocean front views! Smell and hear the sound of the ocean from our condo. It does not get better than this! As of Aug 2017** Newly remodeled unit with new kitchen, bathroom, living room, custom built-in cabinetry...

    Pool
    FREE CANCELLATION

    $336 to $603/night

  22. CONDOMINIUM
    Mahana Resort Unit #405

    Mahana Resort Unit #405

    Lahaina, HI

    Welcome to Mahana 405! This beautiful oceanfront condo on North Kaanapali beach sleeps 2-4 and features a convenient second bathroom. Enjoy stunning views of the ocean, beach and outer islands from the living room, dining area, bedroom, and lanai....

    Pool
    FREE CANCELLATION

    $325 to $797/night

  23. CONDOMINIUM
    Mahana Resort Unit #305

    Mahana Resort Unit #305

    Lahaina, HI

    Ocean front on North Ka'anapali beach. An ocean front bedroom allows for a greater view in this Deluxe unit that has been completely remodeled. In addition to the 52" flat screen plasma TV, Blu-Ray DVD player and surround sound in the living room...

    Pool
    FREE CANCELLATION

    $325 to $606/night

  24. CONDOMINIUM
    Mahana Resort Unit #1107

    Mahana Resort Unit #1107

    Lahaina, HI

    Welcome to Mahana 1107! Located on the eleventh-floor, this recently remodeled one bedroom, one bath condo sleeps 2-4 and features stunning panoramic views of the ocean, beach and outer islands from the living room, dining area, bedroom, and lanai....

    Pool
    FREE CANCELLATION

    $325 to $638/night

  25. CONDOMINIUM
    Maui Kamaole #J-219

    Maui Kamaole #J-219

    Kihei, HI

    Kamaole Beach III is just across the street 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...

    Pool
    FREE CANCELLATION

    $324 to $486/night

  26. CONDOMINIUM
    Kaanapali Royal Q101

    Kaanapali Royal Q101

    Lahaina, HI

    Newly redecorated! Spacious corner unit has 1,500 square foot with 500 square foot lanai 2 bedroom, 2 bathroom sleeps a maximum of 8 guests. Located in the gated condominium complex of Kaanapali Royal in the heart of the Kaanapali Resort,This...

    Pool
    FREE CANCELLATION

    $316 to $1,238/night

  27. CONDOMINIUM
    Honua Kai Konea 314

    Honua Kai Konea 314

    Kaanapali, HI

    GREAT PRIVATE ONE BEDROOM!! NOTE: As of 2/6/18 construction of 72 Townhomes has commenced behind the Konea building at Honua kai. There may be noise and dust on work days during construction hours from 8am to 5pm. Best one bedroom plan available...

    Pool Hot Tub
    FREE CANCELLATION

    $315 to $1,003/night

  28. CONDOMINIUM
    Mahana Resort Unit #706

    Mahana Resort Unit #706

    Kaanapali, HI

    Ocean front on the 7th floor on North Kaanapali beach. Nov '12 remodel included new kitchen cabinets, fresh paint, new furniture and flooring. Professionally decorated this 7th floor condo is a must see! Floor to ceiling windows in the living room...

    Pool
    FREE CANCELLATION

    $313 to $669/night

  29. CONDOMINIUM
    Wailea Ekolu #105

    Wailea Ekolu #105

    Kihei, 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

    $307 to $534/night

  30. CONDOMINIUM
    Maui Vista 3420

    Maui Vista 3420

    Kihei, HI

    100% remodeled condo! This spacious two bedroom condo has mountain and partial ocean views and is located across the street from the long sandy shore of Charley Young beach. Located in the back of the property, this unit is quiet and peaceful....

    Pool
    FREE CANCELLATION

    $306 to $369/night