Hawaii Vacation Rentals – Explore Island Homes, Beach Condos & Luxury Villas

Planning a getaway to the Hawaiian Islands? Whether you're dreaming of waking up to ocean views in a beachfront condo or relaxing in a private villa surrounded by lush tropical gardens, Hawaii offers vacation rentals to match every traveler’s style. From the golden sands of Maui to the serene shores of Kauai, and the adventure-filled landscapes of the Big Island to the vibrant energy of Oahu, each island invites you to discover its unique charm.

Choose from a variety of accommodations including luxury villas, cozy bungalows, oceanfront homes, and resort-style condos with full amenities. Ideal for couples, families, and groups, these rentals provide the perfect base for exploring nearby beaches, cultural landmarks, hiking trails, and snorkeling spots. Enjoy the freedom of a private stay with space to unwind and all the comforts of home.

Each listing is curated with detailed descriptions and high-quality photos, helping you find a place that fits your needs and budget. Whether you're booking your first trip or returning for another island adventure, your perfect Hawaiian escape begins with the right accommodations. Start browsing on To-Hawaii.com and turn your vacation plans into unforgettable memories.

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Beachfront Maui Condo at Sugar Beach Resort
Beachfront Maui Condo at Sugar Beach Resort
Beachfront Maui Condo at Sugar Beach Resort

Beachfront Maui Condo at Sugar Beach Resort

Escape to Sugar Beach Resort, located on the scenic north side of Kihei, Maui. This beachfront condo offers breathtaking ocean views and direct access to miles of pristine Sugar Beach. Wake up to the sunrise from your lanai while sipping coffee, then step outside for beach walks, swimming, snorkeling, and water sports right at your doorstep.

  • 1 bedroom
  • 1 bathroom
  • Sleeps 2
Hawaii> Kihei
from $323 
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Waikiki Ocean and Park View Condo with Rooftop Pool
Waikiki Ocean and Park View Condo with Rooftop Pool
Waikiki Ocean and Park View Condo with Rooftop Pool

Waikiki Ocean and Park View Condo with Rooftop Pool

Discover this beautifully renovated high-floor condo in the heart of Waikiki, offering breathtaking ocean and park views from your private lanai. Natural light floods the spacious interior, which features modern amenities like central air conditioning, a full-size washer and dryer, and high-speed fiber optic internet—ideal for remote work or leisure.
Registration Number: GE-026-663-4240-01, TA-026-663-4240-01, 260070060116

  • 1 bedroom
  • 1 bathroom
  • Sleeps 2
Hawaii> Honolulu
from $182 
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Poipu Beach Suite for Large Groups & Family Reunions
Poipu Beach Suite for Large Groups & Family Reunions
Poipu Beach Suite for Large Groups & Family Reunions

Poipu Beach Suite for Large Groups & Family Reunions

Experience the perfect blend of comfort and tropical charm in this spacious plantation-style beach suite in Poipu, Kauai. Covering 3,000 square feet, the Turtle Suite is part of the historic Pane Makai Beach House duplex, offering ample space for large groups, family reunions, or wedding parties.

  • 4 bedroom
  • 2 bathroom
  • Sleeps 8
Hawaii> koloa
from $1,067 
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Beach Glam @ Turtle Bay - Kuilima Estates West
Beach Glam @ Turtle Bay - Kuilima Estates West
Beach Glam @ Turtle Bay - Kuilima Estates West

Beach Glam @ Turtle Bay - Kuilima Estates West

We are all looking for a quiet, restful, safe place to de-stress and forget the troubles of the world. As a Hawaii born and raised local, there are few places that can rival this task than the North Shore on Oahu. With 24 hr security, free parking, and the Turtle Bay golf course as your backyard, our Kuilima Estates West condominium is perfect for a couple or a family looking for the ultimate Hawaiian escape.
Registration Number: 570010290098, TA-136-982-1184-01, GE-136-982-1184-01

  • 2 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Kahuku
from $780 
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Charming 2BR Ocean View Condo in Kihei Maui
Charming 2BR Ocean View Condo in Kihei Maui
Charming 2BR Ocean View Condo in Kihei Maui

Charming 2BR Ocean View Condo in Kihei Maui

Welcome to Pacific Shores A304, a beautifully updated 2-bedroom, 2-bathroom condo in Kihei, Maui, available for an unforgettable island stay. Freshly renovated in May 2024, this unit features all new furniture, artwork, and decor that create a welcoming and stylish atmosphere.

  • 2 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Kihei
from $290 
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Luxury Kauai Eco-Retreat with Natural Wood Decor
Luxury Kauai Eco-Retreat with Natural Wood Decor
Luxury Kauai Eco-Retreat with Natural Wood Decor

Luxury Kauai Eco-Retreat with Natural Wood Decor

Experience the ultimate Kauai escape in this beautifully crafted two-story retreat, surrounded by lush jungle sounds and natural light. The spacious layout offers five bedrooms, including a master suite that comfortably fits multiple beds, making it ideal for families or groups.

  • 5 bedroom
  • 3 bathroom
  • Sleeps 30
Hawaii> Princeville
from $1,605 
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Beautiful Maui Eldorado H208 with Ocean Views
Beautiful Maui Eldorado H208 with Ocean Views
Beautiful Maui Eldorado H208 with Ocean Views

Beautiful Maui Eldorado H208 with Ocean Views

Welcome to Maui Eldorado H208! This beautifully renovated second-floor condo offers 1440 sq ft of comfortable living space, featuring 2 bedrooms and 2 bathrooms, ideal for your Maui holiday.
The spacious lanai provides stunning ocean views, perfect for watching sunsets while enjoying a tropical cocktail or an al fresco dinner at the two patio dining tables, making it a great spot for family gatherings or relaxing with friends.

  • 2 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Kaanapali
from $591 
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Baby Beach Bungalow 2 in Poipu Kauai Ocean Views
Baby Beach Bungalow 2 in Poipu Kauai Ocean Views
Baby Beach Bungalow 2 in Poipu Kauai Ocean Views

Baby Beach Bungalow 2 in Poipu Kauai Ocean Views

Welcome to Baby Beach Bungalow 2, a cozy tropical retreat nestled in a family-friendly neighborhood on Ho'ona Road in Poipu, Kauai. Just steps from the crescent-shaped white sand Baby Beach, this charming home offers stunning ocean views, beautiful sunsets, and opportunities to see dolphins, turtles, and seasonal breaching whales right from the living room, kitchen, and covered lanai.

  • 2 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Poipu
from $613 
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Oceanfront Condo Near Punalu'u Black Sand Beach
Oceanfront Condo Near Punalu'u Black Sand Beach
Oceanfront Condo Near Punalu'u Black Sand Beach

Oceanfront Condo Near Punalu'u Black Sand Beach

Aloha! Welcome to Hale Maluhia, a truly special and unique part of Hawaii. This spacious one-bedroom condo sits directly oceanfront at Sea Mountain Resort near Punalu'u Black Sand Beach. Built in the traditional 'Kama'aina' Hawaiian bungalow style, it features fully furnished interiors with hardwood and tile floors throughout.

  • 1 bedroom
  • 1 bathroom
  • Sleeps 4
Hawaii> Pahala
from $237 
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Wailea Grand Champions Villas Vacation Condo
Wailea Grand Champions Villas Vacation Condo
Wailea Grand Champions Villas Vacation Condo

Wailea Grand Champions Villas Vacation Condo

Welcome to Wailea Grand Champions Villas, your ideal Maui vacation destination. Nestled amid Wailea's Blue Golf Course and adjacent to the Wailea Tennis Club, this recently renovated 2-bedroom, 2-bathroom condo offers a perfect blend of comfort and convenience.

  • 2 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Wailea-Makena
from $800 
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Oceanfront Maui Condo with Stunning Views at Mana Kai
Oceanfront Maui Condo with Stunning Views at Mana Kai
Oceanfront Maui Condo with Stunning Views at Mana Kai

Oceanfront Maui Condo with Stunning Views at Mana Kai

Step into paradise at Mana Kai 714, a beautifully updated oceanfront condo perched on the 7th floor with breathtaking views of the Pacific Ocean and Haleakala volcano. This luxurious retreat offers a perfect blend of comfort and style, ideal for families and couples seeking a serene Maui getaway.

  • 2 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Kihei
from $953 
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Vista Waikoloa D301 Beach Resort Condo
Vista Waikoloa D301 Beach Resort Condo
Vista Waikoloa D301 Beach Resort Condo

Vista Waikoloa D301 Beach Resort Condo

Welcome to Vista Waikoloa D301, your perfect slice of paradise on the Big Island. This beautifully furnished end-unit condo offers 350 sq ft of wrap-around lanai space with peek-a-boo views of Anaeho'omalu Bay, providing an ideal setting for relaxation and sightseeing.

  • 2 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Waikoloa Village
from $426 
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Honua Kai Oceanview 2BR Condo with Spectacular Views
Honua Kai Oceanview 2BR Condo with Spectacular Views
Honua Kai Oceanview 2BR Condo with Spectacular Views

Honua Kai Oceanview 2BR Condo with Spectacular Views

Discover the stunning beauty of Maui from our luxurious 2-bedroom, 2-bath condo at Honua Kai Resort. Located on the top floor of Hokulani Tower, our condo offers unobstructed panoramic ocean and resort views from the lanai, making it an ideal retreat for relaxation and adventure.

  • 2 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Lahaina
from $873 
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Stunning Maui Golf Condo with Ocean & Sunset Views
Stunning Maui Golf Condo with Ocean & Sunset Views
Stunning Maui Golf Condo with Ocean & Sunset Views

Stunning Maui Golf Condo with Ocean & Sunset Views

Discover the ultimate Maui vacation at this stunning ground-floor condo, perfectly situated on the 10th fairway with breathtaking ocean and sunset views. Step onto your lanai to watch whales breaching and enjoy the serene beauty of the island. Located in the exclusive Kapalua Resort, this villa offers easy access to five nearby beaches ideal for snorkeling with sea turtles, swimming, paddleboarding, or sunbathing.

  • 2 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Kapalua
from $607 
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Luxury Family Reunion Vacation Home with Private Pools
Luxury Family Reunion Vacation Home with Private Pools
Luxury Family Reunion Vacation Home with Private Pools

Luxury Family Reunion Vacation Home with Private Pools

Discover this exceptional vacation home perfect for small family reunions, birthdays, graduations, or vow renewals. The property boasts eight spacious bedrooms, each with its own private lanai and en-suite bathroom, providing privacy and comfort for all guests.

  • 8 bedroom
  • 7 bathroom
  • Sleeps 23
Hawaii> Mountain View
from $2,117 
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Oceanfront 1BR Condo at Sugar Beach Resort Maui
Oceanfront 1BR Condo at Sugar Beach Resort Maui
Oceanfront 1BR Condo at Sugar Beach Resort Maui

Oceanfront 1BR Condo at Sugar Beach Resort Maui

Welcome to Sugar Beach 518, a beautifully updated oceanfront condo offering a perfect Maui getaway. This 1-bedroom, 1-bathroom unit comfortably accommodates 4 guests and boasts stunning ocean views from every room, including your private lanai.

  • 1 bedroom
  • 1 bathroom
  • Sleeps 4
Hawaii> Kihei
from $364 
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Spacious 1-Bedroom with Modern Updates and Paradise Views
Spacious 1-Bedroom with Modern Updates and Paradise Views
Spacious 1-Bedroom with Modern Updates and Paradise Views

Spacious 1-Bedroom with Modern Updates and Paradise Views

Experience a beautifully renovated 1-bedroom condo in a peaceful concrete building with high ceilings and lush Hawaiian plants. Recent upgrades include new flooring, a walk-in shower, a new vanity, and modern kitchen cabinets with new countertops and appliances.

  • 1 bedroom
  • 1 bathroom
  • Sleeps 2
Hawaii> Lahaina
from $315 
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Wailea Ekahi 2BR Ocean View Condo with Bunk Beds
Wailea Ekahi 2BR Ocean View Condo with Bunk Beds
Wailea Ekahi 2BR Ocean View Condo with Bunk Beds

Wailea Ekahi 2BR Ocean View Condo with Bunk Beds

A modern and spacious 2-bedroom, 2-bath condo located in the beautiful Wailea Ekahi Village, offering breathtaking ocean views and comfortable living spaces. The unit features extra bunk beds, making it ideal for families or groups of friends. At 1200 sqft, this top-floor, professionally decorated apartment combines luxury finishes with practical amenities, ensuring a relaxing stay in Maui.

  • 2 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Kihei
from $865 
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Charming Hanalei Bay Vacation Home with Mountain Views
Charming Hanalei Bay Vacation Home with Mountain Views
Charming Hanalei Bay Vacation Home with Mountain Views

Charming Hanalei Bay Vacation Home with Mountain Views

Discover this charming and spacious vacation home located just steps from Hanalei Bay, nestled in the beautiful landscape of Kauai. The property offers over 900 square feet of living space, perfect for relaxing and exploring the island. Enjoy stunning mountain views and waterfalls from the private upstairs unit, which features its own entrance and parking area.

  • 1 bedroom
  • 1 bathroom
  • Sleeps 2
Hawaii> Hanalei
from $336 
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Ocean View Pool Home in Discovery Harbour
Ocean View Pool Home in Discovery Harbour
Ocean View Pool Home in Discovery Harbour

Ocean View Pool Home in Discovery Harbour

Discover your perfect Hawaiian retreat in this beautifully designed 3-bedroom, 2-bath single-level home located in Discovery Harbour. The house features a stunning saltwater solar-heated pool, ideal for relaxing or entertaining. A Japanese-inspired pagoda and gazebo create a tranquil outdoor space where you can enjoy your morning coffee, afternoon cocktails, or peaceful yoga sessions amidst lush tropical gardens and panoramic views of the ocean, hills, and vibrant flowers.

  • 3 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Naalehu
from $409 
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Island Surf #605 Maui Beachfront Condo with Ocean Views
Island Surf #605 Maui Beachfront Condo with Ocean Views
Island Surf #605 Maui Beachfront Condo with Ocean Views

Island Surf #605 Maui Beachfront Condo with Ocean Views

Welcome to Island Surf #605, a beautifully remodeled top-floor condo in sunny South Kihei, Maui. This unit offers spectacular, unobstructed Pacific Ocean vistas, including stunning sunsets and views of Lanai, Kaho'olawe, and Molokini crater through floor-to-ceiling glass in the living area and a large 16-foot lanai.

  • 1 bedroom
  • 1 bathroom
  • Sleeps 2
Hawaii> Kihei
from $309 
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Luxury Flora Paradise Villa in Kohala Coast
Luxury Flora Paradise Villa in Kohala Coast
Luxury Flora Paradise Villa in Kohala Coast

Luxury Flora Paradise Villa in Kohala Coast

Welcome to Flora Paradise Villa, a stunning part of our Hawaiian Luxury Collection on the beautiful Kohala Coast. This 3-bedroom, 3-bathroom home offers two spacious master suites and is professionally decorated to provide a luxurious and comfortable stay.

  • 3 bedroom
  • 3 bathroom
  • Sleeps 8
Hawaii> Kohala Coast
from $672 
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Charming 600sqft Maui Vista Condo Near Beach
Charming 600sqft Maui Vista Condo Near Beach
Charming 600sqft Maui Vista Condo Near Beach

Charming 600sqft Maui Vista Condo Near Beach

Aloha! Discover our beautifully renovated 600 sqft condo nestled in the heart of Kihei, just a 3-minute stroll from stunning white sand beaches like Charlie Young and Kam I & II.
This inviting condo offers a luxurious king-sized bed with a plush 14-inch hotel-style mattress, perfect for restful nights after a day of island adventures.

  • 1 bedroom
  • 1 bathroom
  • Sleeps 4
Hawaii> Kihei
from $269 
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Luxury Big Island Hale Ali'i Villa with Pool
Luxury Big Island Hale Ali'i Villa with Pool
Luxury Big Island Hale Ali'i Villa with Pool

Luxury Big Island Hale Ali'i Villa with Pool

Discover the beauty and tranquility of our Big Island Hale Ali'i villa, offering resort-style living in a private, lush setting. Located in the exclusive Aliʻi Heights neighborhood of Kailua Kona, this home provides the perfect blend of comfort and elegance for your island escape.

  • 3 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Kailua-Kona
from $518 
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Charming Palaka Cottage Near Hanalei Bay Kauai
Charming Palaka Cottage Near Hanalei Bay Kauai
Charming Palaka Cottage Near Hanalei Bay Kauai

Charming Palaka Cottage Near Hanalei Bay Kauai

Escape to the enchanting Palaka Cottage, a beautifully renovated 2-bedroom, 1-bath vacation home that captures the nostalgic charm of old Hawaiian plantation cottages. Located directly across from the iconic Hanalei Bay, this cottage offers a perfect blend of historic appeal and modern comforts.

  • 2 bedroom
  • 1 bathroom
  • Sleeps 4
Hawaii> Hanalei
from $950 
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Luxury 2BR Condo at Fairways Mauna Lani Hawaii
Luxury 2BR Condo at Fairways Mauna Lani Hawaii
Luxury 2BR Condo at Fairways Mauna Lani Hawaii

Luxury 2BR Condo at Fairways Mauna Lani Hawaii

Welcome to Fairways at Mauna Lani 1001, a beautifully renovated two-bedroom, two-bathroom condo situated in one of the best locations within the complex. Recently updated with attention to detail in May 2024, this home offers a perfect blend of comfort and style.

  • 2 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Kamuela
from $419 
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Hawaii Pickleball Addicts Lodge with Courts & Views
Hawaii Pickleball Addicts Lodge with Courts & Views
Hawaii Pickleball Addicts Lodge with Courts & Views

Hawaii Pickleball Addicts Lodge with Courts & Views

Welcome to Hawaii Pickleball Addicts Lodge, a stunning private residence nestled on two lush acres in Mountain View, HI. This spacious home is specifically designed for large groups, families, or multiple families traveling together, offering the perfect combination of comfort, adventure, and sport.

  • 7 bedroom
  • 3 bathroom
  • Sleeps 14
Hawaii> Mountain View
from $1,052 
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Beautiful 2BR Ocean View Condo in Hawaii
Beautiful 2BR Ocean View Condo in Hawaii
Beautiful 2BR Ocean View Condo in Hawaii

Beautiful 2BR Ocean View Condo in Hawaii

Come and indulge in a well-deserved vacation in paradise at this lovely 2-bedroom, 2-bath ocean view condo. This townhouse features two lanais with stunning ocean vistas and comes equipped with central air conditioning for your comfort. Located within walking distance to Kahalu'u, a renowned snorkeling beach on The Big Island, you'll have easy access to vibrant marine life and warm waters.

  • 2 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Kailua Kona
from $318 
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Hawaii East Hawaii Waterfall View Villa with Hot Tub
Hawaii East Hawaii Waterfall View Villa with Hot Tub
Hawaii East Hawaii Waterfall View Villa with Hot Tub

Hawaii East Hawaii Waterfall View Villa with Hot Tub

Set on the slopes of Mauna Kea at 1200 feet above the charming town of Honomu, this stunning property offers unparalleled views of East Hawaii's lush landscape and ocean vistas. Nestled on fifteen acres bordering a peaceful stream, the home provides a serene escape from everyday life.

  • 3 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Honomu
from $307 
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Oceanfront Maui Penthouse with Beach Access and Views
Oceanfront Maui Penthouse with Beach Access and Views
Oceanfront Maui Penthouse with Beach Access and Views

Oceanfront Maui Penthouse with Beach Access and Views

Welcome to Papakea B406, your perfect oceanfront retreat in Maui! This spacious three-bedroom, two-bath penthouse offers breathtaking ocean views, soothing sounds of waves, and a prime location within walking distance to beautiful beaches, local markets, the ABC store, restaurants, and food trucks.

  • 3 bedroom
  • 2 bathroom
  • Sleeps 8
Hawaii> Lahaina
from $773 
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Spacious 3-Bedroom Plantation Condo with Luxurious Amenities
Spacious 3-Bedroom Plantation Condo with Luxurious Amenities
Spacious 3-Bedroom Plantation Condo with Luxurious Amenities

Spacious 3-Bedroom Plantation Condo with Luxurious Amenities

Welcome to our beautiful Plantation condo #1522, your perfect vacation retreat. This spacious 3-bedroom, 3-bath property offers comfort and elegance, ideal for families or groups seeking a relaxing escape. The condo features a builder upgrade package, adding touches of sophistication throughout.

  • 3 bedroom
  • 3 bathroom
  • Sleeps 6
Hawaii> Princeville
from $483 
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Oceanview Papakea Resort K-301 Maui Retreat
Oceanview Papakea Resort K-301 Maui Retreat
Oceanview Papakea Resort K-301 Maui Retreat

Oceanview Papakea Resort K-301 Maui Retreat

Aloha from Midway Vacations! Our dedicated team of local hospitality experts ensures your Hawaiian escape is seamless and memorable. When you choose one of our properties, you benefit from professionally cleaned, meticulously maintained spaces and 24/7 support for any needs.

  • 1 bedroom
  • 1 bathroom
  • Sleeps 4
Hawaii> Lahaina
from $496 
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Secluded Maui Coffee Estate Cottage with Ocean Views
Secluded Maui Coffee Estate Cottage with Ocean Views
Secluded Maui Coffee Estate Cottage with Ocean Views

Secluded Maui Coffee Estate Cottage with Ocean Views

This charming, all-one-level cottage is nestled on a 20-acre shade-grown coffee plantation bordering a lush forest preserve. It offers complete privacy and breathtaking panoramic views of the ocean, jungle, and mountains, with a seasonal waterfall adding to the scenic beauty.

  • 1 bedroom
  • 1 bathroom
  • Sleeps 4
Hawaii> Makawao
from $442 
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Luxurious Oceanfront 2-Bedroom Condo in Kihei Maui
Luxurious Oceanfront 2-Bedroom Condo in Kihei Maui
Luxurious Oceanfront 2-Bedroom Condo in Kihei Maui

Luxurious Oceanfront 2-Bedroom Condo in Kihei Maui

Experience the ultimate Maui getaway in this fully remodeled and professionally decorated 2-bedroom, 2-bath oceanfront condo at Menehune Shores in Kihei. Completed in April 2023, the condo boasts luxurious furnishings and all new amenities, creating a stylish and comfortable retreat just steps from the beach.

  • 2 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Kihei
from $665 
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Luxury Two-Bedroom Condo Near Kahana Beach
Luxury Two-Bedroom Condo Near Kahana Beach
Luxury Two-Bedroom Condo Near Kahana Beach

Luxury Two-Bedroom Condo Near Kahana Beach

Indulge in a week of luxurious comfort in this elegant two-bedroom unit located directly across from the beautiful Kahana Beach. Designed for relaxation and adventure, the condo offers a range of amenities including a refreshing pool, tennis courts, and air conditioning to ensure a comfortable stay.

  • 2 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Lahaina
from $347 
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Spacious 1 Bedroom Ground Floor Condominium in Kailua-Kona
Spacious 1 Bedroom Ground Floor Condominium in Kailua-Kona
Spacious 1 Bedroom Ground Floor Condominium in Kailua-Kona

Spacious 1 Bedroom Ground Floor Condominium in Kailua-Kona

Experience the beauty of Hawaii at Casa De Emdeko, where this charming 920 sq ft ground-floor condo offers an unbeatable location just 30 feet from the sandy beach. Wake up to breathtaking ocean views and enjoy the soothing sounds of the waves from the comfort of your condo.

  • 2 bedroom
  • 1 bathroom
  • Sleeps 4
Hawaii> Kailua-Kona
from $245 
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Luxury Oceanfront Beach Villa at Ko Olina
Luxury Oceanfront Beach Villa at Ko Olina
Luxury Oceanfront Beach Villa at Ko Olina

Luxury Oceanfront Beach Villa at Ko Olina

Experience the ultimate Hawaiian getaway in this luxurious 2nd-floor Beach Villa at Ko Olina, renowned for its pristine lagoons and top-tier amenities. Nestled just 500 feet from the ocean, this spacious 1478 sq. ft. villa offers stunning sunset views from a large private lanai.
Registration Number: GE-203-453-6448-01, TA-203-453-6448-01

  • 3 bedroom
  • 3 bathroom
  • Sleeps 6
Hawaii> Ko Olina
from $978 
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Honeymoon Tiki Suite in Princeville Kauai
Honeymoon Tiki Suite in Princeville Kauai
Honeymoon Tiki Suite in Princeville Kauai

Honeymoon Tiki Suite in Princeville Kauai

Welcome to the beautifully renovated Honeymoon Tiki Suite, a top-floor retreat nestled in Princeville's most desirable location. Just a short stroll from some of Kauai's most iconic beaches—Hideaways Beach, Secret Beach, and Pali Ke Kua Beach—this suite provides an idyllic setting for your island escape.

  • 1 bedroom
  • 1 bathroom
  • Sleeps 2
Hawaii> Princeville
from $459 
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Beautiful Maui Eldorado Condo with Ocean Views & Activities
Beautiful Maui Eldorado Condo with Ocean Views & Activities
Beautiful Maui Eldorado Condo with Ocean Views & Activities

Beautiful Maui Eldorado Condo with Ocean Views & Activities

Discover the perfect Hawaiian escape in this beautifully updated 1-bedroom, 2-bath condo located within the Maui Eldorado Resort along the stunning shores of Kaanapali Beach. The bright, airy interior features charming Hawaiian coastal decor that creates a peaceful retreat to unwind and enjoy island living.

  • 1 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Lahaina
from $307 
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Honua Kai Corner Studio with Ocean Views
Honua Kai Corner Studio with Ocean Views
Honua Kai Corner Studio with Ocean Views

Honua Kai Corner Studio with Ocean Views

Experience the ultimate Maui retreat in this luxurious corner studio condo located at Honua Kai, perched above the lush courtyard offering delightful peek-a-boo ocean views through vibrant tropical foliage. Step outside onto the spacious lanai and be captivated by the surrounding flowers, swaying trees, and tranquil koi ponds that create a serene backdrop for your stay.

  • 2 bedroom
  • 1 bathroom
  • Sleeps 4
Hawaii> Lahaina
from $382 
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Beachfront Condo with Pool and Stunning Sunsets
Beachfront Condo with Pool and Stunning Sunsets
Beachfront Condo with Pool and Stunning Sunsets

Beachfront Condo with Pool and Stunning Sunsets

This recently updated condo offers an unbeatable location right next to the beach and pool, with nothing obstructing your view of the ocean. Situated on the ground floor in a corner unit, it provides easy access to the sandy shores and the pool area, making it ideal for those seeking convenience and stunning scenery.

  • 2 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Lahaina
from $560 
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Kaunakakai Oceanfront Condo with Pool & Views
Kaunakakai Oceanfront Condo with Pool & Views
Kaunakakai Oceanfront Condo with Pool & Views

Kaunakakai Oceanfront Condo with Pool & Views

Experience a relaxing island escape in this beautiful oceanfront condo located in the Wavecrest Resort in Kaunakakai, Molokai. This 1-bedroom, 1-bath unit offers stunning ocean and island views from your private lanai, making it the perfect spot for your Hawaiian vacation.

  • 1 bedroom
  • 1 bathroom
  • Sleeps 2
Hawaii> Kaunakakai
from $145 
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Oceanfront Vacation Rental 'Livin the Aloha Dream'
Oceanfront Vacation Rental 'Livin the Aloha Dream'
Oceanfront Vacation Rental 'Livin the Aloha Dream'

Oceanfront Vacation Rental 'Livin the Aloha Dream'

Welcome to 'Livin the Aloha Dream', a stunning oceanfront retreat where the magic of Maui unfolds right outside your door. Imagine waking up to panoramic views of the Pacific Ocean, with the islands of Molokai and Lanai visible from your private lanai.

  • 2 bedroom
  • 1 bathroom
  • Sleeps 4
Hawaii> Lahaina
from $415 
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Beachfront Surfer's Paradise on Oahu North Shore
Beachfront Surfer's Paradise on Oahu North Shore
Beachfront Surfer's Paradise on Oahu North Shore

Beachfront Surfer's Paradise on Oahu North Shore

Welcome to Surfer's Paradise by Gather, the ultimate beachfront vacation rental on the North Shore of Oahu. With its clean, spacious, and uncluttered space, Surfer’s Paradise is the perfect place to enjoy every second of your vacation.
Registration Number: 590020340000, TA-155-479-0912-01, GE-155-479-0912-01

  • 3 bedroom
  • 2 bathroom
  • Sleeps 8
Hawaii> Haleiwa
from $1,617 
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Luxury Bay View Farms Estate House in Hawaii
Luxury Bay View Farms Estate House in Hawaii
Luxury Bay View Farms Estate House in Hawaii

Luxury Bay View Farms Estate House in Hawaii

Escape to the serene beauty of Bay View Farms Estate House, a luxurious 6,400 sq. ft. retreat nestled on a working coffee plantation on Hawaii's Big Island. This beautifully decorated estate offers a perfect blend of indoor comfort and outdoor paradise, making it ideal for families or groups seeking a memorable vacation.

  • 3 bedroom
  • 6 bathroom
  • Sleeps 20
Hawaii> Captain Cook
from $2,902 
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Kanai A Nalu Beachfront Condo in Maui
Kanai A Nalu Beachfront Condo in Maui
Kanai A Nalu Beachfront Condo in Maui

Kanai A Nalu Beachfront Condo in Maui

Experience the beauty of Maui from Kanai A Nalu, a beautifully remodeled beachfront condo offering stunning ocean views and modern comforts. This ground-floor unit features tile flooring throughout, island-style furniture, and a fully equipped kitchen with a full-size front load washer and dryer, making it feel like a home away from home in paradise.

  • 2 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Wailuku
from $360 
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Spacious 5-Bedroom Family Home in Aina Haina
Spacious 5-Bedroom Family Home in Aina Haina
Spacious 5-Bedroom Family Home in Aina Haina

Spacious 5-Bedroom Family Home in Aina Haina

This charming five-bedroom, three-bathroom residence is nestled in the peaceful neighborhood of Aina Haina, offering a serene retreat just a short drive from the vibrant attractions of south Oahu. The home features an open floor plan that’s ideal for family gatherings, with a spacious living room boasting vaulted ceilings and ample seating.
Registration Number: 350450560000, GE-040-366-2848-01, TA-040-366-2848-01

  • 5 bedroom
  • 3 bathroom
  • Sleeps 10
Hawaii> Honolulu
from $551 
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Modern Luxury Remodel - Maui Kamaole J114
Modern Luxury Remodel - Maui Kamaole J114
Modern Luxury Remodel - Maui Kamaole J114

Modern Luxury Remodel - Maui Kamaole J114

Boasting ocean and West Maui Mountain views from the lanai, a modern chef’s kitchen, a resort-style en-suite bathroom with a Calcutta Laza Quartz double vanity, and a King size bed featuring a Sealy Tempurpedic cooling memory foam mattress, this is the luxury rental you’ve been dreaming of.

  • 1 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Kihei
from $391 
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Elegant 4-Bedroom Kauai Vacation Home with Pool
Elegant 4-Bedroom Kauai Vacation Home with Pool
Elegant 4-Bedroom Kauai Vacation Home with Pool

Elegant 4-Bedroom Kauai Vacation Home with Pool

5-bath vacation home offers a perfect blend of luxury, comfort, and convenience in a quiet, upscale neighborhood on Kauai. Spanning 2,234 square feet, this bright and airy residence features four spacious bedrooms, each with plush king-size beds dressed in high-end Frette linens, providing a restful retreat after a day exploring the island.

  • 4 bedroom
  • 3 bathroom
  • Sleeps 8
Hawaii> Koloa
from $1,173 
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Waikiki Oceanview Condo with Rooftop Pool
Waikiki Oceanview Condo with Rooftop Pool
Waikiki Oceanview Condo with Rooftop Pool

Waikiki Oceanview Condo with Rooftop Pool

Aloha from Midway Vacations! Our dedicated team of local hospitality experts is here to help make your Hawaiian dream a reality. Staying at one of our properties ensures a professionally cleaned, meticulously maintained, and welcoming experience.
Registration Number: 260230560149, GE-199-719-4752-01, TA-199-719-4752-01

  • 1 bedroom
  • 1 bathroom
  • Sleeps 4
Hawaii> Honolulu
from $483 
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