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. 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

    $2212 to $3444/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

    $1968 to $3075/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

    $1661 to $2429/night

  4. HOUSE
    The Oasis

    The Oasis

    Kamuela, HI

    Remodeled and redecorated in 2018, The Oasis boasts vaulted ceilings, tropical hardwoods, marble and granite counter tops, air conditioning, and expansive living spaces with plenty of luxurious seating. Along with a professional chef’s kitchen, an...

    Pool

    $1384 to $2811/night

  5. HOUSE
    4BD Estate Home at Puako Bay (74)

    4BD Estate Home at Puako Bay (74)

    Kamuela, HI

    This elegant and timeless oceanfront estate is situated on the scenic shores of beautiful Puako Bay. One of Hawaii's last remaining peaceful little beach communities, Puako is steeped in history from abundant fishing to sugar cane farming and epic...

    $1230 to $3575/night

  6. VILLA
    Fairways Villa 116C

    Fairways Villa 116C

    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

    $1040 to $2918/night

  7. VILLA
    Bay Villa 20G2 Gold Beach Front

    Bay Villa 20G2 Gold Beach Front

    Lahaina, HI

    We invite you to be carried away by this luxury beachfront villa overlooking the azure waters of beautiful Oneloa Bay. Our property is uniquely positioned above the beach in the most desirable location of Kapalua, the crown jewel of West Maui. This...

    Pool

    $847 to $1322/night

  8. 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 $1668/night

  9. CONDOMINIUM
    Wailea Elua Unit #2204

    Wailea Elua Unit #2204

    Wailea, 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 $1065/night

  10. 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 $1065/night

  11. 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

    $624 to $2016/night

  12. 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 $1118/night

  13. 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 $1073/night

  14. VILLA
    Ridge1112 Ocean View

    Ridge1112 Ocean View

    Kapalua, HI

    Enjoy 5 star accommodations in an exclusive private villa paradise! Custom Designed and Fully Upgraded Ridge Villa with Ocean Views from Every Room! Designed from the onset to take advantage of its unique Island setting, Kapalua Ridge Villa 1112 is...

    Pool

    $576 to $942/night

  15. 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

  16. CONDOMINIUM
    Hale Ili Ili #D

    Hale Ili Ili #D

    Kihei, HI

    Hale Ili Ili is an oceanfront gated four-plex in Kihei Maui Hawaii. The property lends itself to a very private and relaxed atmosphere with breathtaking sunsets, sounds of the ocean and rustling palm trees. Many whales, turtles, dolphins and rays...

    Pool Hot Tub
    FREE CANCELLATION

    $556 to $927/night

  17. 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 $1668/night

  18. 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

  19. 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 $3613/night

  20. 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

    $428 to $484/night

  21. CONDOMINIUM
    Ilikai #1743

    Ilikai #1743

    Honolulu, HI

    Escape to Hawaii and indulge in sweeping ocean views from the 17th floor at the Ilikai Hotel in Waikiki. Watch the sail boats glide out to the deep blue Pacific while relaxing on the private lanai of this two-bedroom condo. The spacious, open floor...

    Pool
    FREE CANCELLATION

    $425 to $652/night

  22. CONDOMINIUM
    Honua Kai Konea 312

    Honua Kai Konea 312

    Kaanapali, HI

    UPGRADED 2 PLUS ONE!!! Two Bedroom One Bath! West Maui Mountain & Waterfall Views! 915 sq ft! Just renovated with new DESIGNER FURNISHINGS, new flooring and a brand new Queen Bed in the Private Den! New Flat screen 4K TV's with built in Netflix,...

    Pool Hot Tub
    FREE CANCELLATION

    $421 to $1250/night

  23. CONDOMINIUM
    Honua Kai Konea 606

    Honua Kai Konea 606

    Kaanapali, HI

    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. Konea 606 is a large 945 square foot (plus 180 sq ft Lanai)...

    Pool Hot Tub
    FREE CANCELLATION

    $410 to $1214/night

  24. 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

    $406 to $986/night

  25. 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

  26. VILLA
    Bay Villa 32B3 Gold Ocean View

    Bay Villa 32B3 Gold Ocean View

    Lahaina, HI

    Spectacular views of the Pacific and the neighboring island of Molokai. Magnificent painted sky at dusk and dawn will take your breath away! Perfectly positioned to allow warm tropical breezes and gentle sounds of surf fill every room. This...

    Pool

    $400 to $644/night

  27. 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 $1340/night

  28. 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

  29. 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

    $354 to $1133/night

  30. CONDOMINIUM
    35 Walaka Street Condo Unit P207

    35 Walaka Street Condo Unit P207

    Kihei, HI

    The glittering ocean is at your fingertips at this tropical 1BR Kihei condo. Walk 5 minutes to the wide sands of Kamaole Beach or the waves at The Cove (one of the most popular surf breaks in South Maui) for a day of fun in the sun. Later, head back...

    Pool
    FREE CANCELLATION