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Hawaii Vacation Rentals

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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Oceanfront Kailua Bay Condo with Pool & Views

Oceanfront Kailua Bay Condo with Pool & Views

Located on the popular Alii Drive, our True Oceanfront condominium offers breathtaking views of Kailua Bay and beyond. From the lanai, you can observe cruise ships tendering passengers to Kailua Pier, as well as other harbor activities like parasailing.

2 bedroom
2 bathroom
Sleeps 5

from $356

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Oceanfront 1BR Condo at Napili Point Maui

Oceanfront 1BR Condo at Napili Point Maui

Experience the beauty of Maui from Napili Point B34, a charming ground-floor 1-bedroom, 1-bathroom condo offering stunning oceanfront views. The condo comfortably hosts up to 4 guests with a luxurious King bed in the bedroom and a Queen sleeper sofa in the living area.

2 bedroom
1 bathroom
Sleeps 4

from $316

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Charming 1-Bedroom Townhouse Near Kona Beaches

Charming 1-Bedroom Townhouse Near Kona Beaches

Discover this charming 1-bedroom, 1-bath townhouse ideally situated in the heart of Kona. The property features a fully equipped kitchen, a cozy living space, and a private BBQ area, perfect for gatherings. Located just minutes from stunning beaches, vibrant restaurants, and lively sports bars, you'll have easy access to all the best Kona has to offer.

1 bedroom
1 bathroom
Sleeps 6

from $519

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Kanaloa at Kona Oceanfront Condo with Views

Kanaloa at Kona Oceanfront Condo with Views

Experience the ultimate Hawaiian retreat at Kanaloa at Kona, widely regarded as one of the top resorts on the Kona Coast. Nestled on an ancient lava flow that extends into the ocean, this exclusive property offers a peaceful escape away from the hustle and bustle of Alii Drive.

2 bedroom
2 bathroom
Sleeps 6

from $347

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Cozy Maui Beachside Condo Near Mama's Fish House

Cozy Maui Beachside Condo Near Mama's Fish House

Enjoy a cozy, well-located Maui condo just steps from a private beach on the north shore. This 1-bedroom, 1-bath unit is perfect for couples, solo travelers, or small families seeking a relaxing getaway.
Located on the second floor of a three-story walk-up building along Hana Highway, right before Mama's Fish House, this condo offers convenience and comfort in a prime location.

1 bedroom
1 bathroom
Sleeps 4

from $331

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Charming Kailua-Kona Condo Near Ocean and Attractions

Charming Kailua-Kona Condo Near Ocean and Attractions

Step into this charming Kailua-Kona condo located less than a mile from the sparkling ocean and the vibrant Alii Drive. Recently renovated with tropical furnishings and modern upgrades, this unit offers a perfect blend of comfort and island charm.

2 bedroom
1 bathroom
Sleeps 4

from $237

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Beautiful Kaanapali Maui Condo with Pool & Views

Beautiful Kaanapali Maui Condo with Pool & Views

Discover this beautifully renovated condo in the heart of Kaanapali, Maui, perfect for a relaxing getaway. The unit features a spacious bedroom with a plush California king-sized bed and an en-suite bathroom with a walk-in shower, vessel sink, and granite countertops.

2 bedroom
2 bathroom
Sleeps 4

from $813

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Charming Maui 2-Bedroom House Near Beaches

Charming Maui 2-Bedroom House Near Beaches

This charming two-bedroom house offers a cozy and authentic Maui experience. With high vaulted ceilings and shiny wood floors, the home provides a warm, inviting atmosphere for guests. 9 miles from Paia town, it’s ideally situated for exploring the North Shore’s renowned beaches, surf spots, and outdoor activities.

3 bedroom
1 bathroom
Sleeps 4

from $447

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Hawaii Kepuhi Beach Resort Oceanfront Studio Condo

Hawaii Kepuhi Beach Resort Oceanfront Studio Condo

Escape to the stunning Kepuhi Beach Resort located adjacent to Papohaku Beach, offering three miles of pristine white sand. Address: 1131 Kaluakoi Rd, Unit 2174, Maunaloa, HI 96770. This oceanfront studio condo provides everything needed for a relaxing island getaway.

2 bedroom
1 bathroom
Sleeps 2

from $178

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Beachfront Condo at Maui Eldorado with Golf Views

Beachfront Condo at Maui Eldorado with Golf Views

Maui Eldorado Beach Resort welcomes you to our spacious 1200 sq ft ground-floor corner condo, ideally located beside the 4th fairway of the Royal Kaanapali Golf Course. This beautifully maintained unit features two queen-size bedrooms, each with private access to a dressing area, bathroom, and shower, providing comfort and privacy for guests.

2 bedroom
1 bathroom
Sleeps 4

from $409

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Diamond Head Beach Hotel Ocean View Studio with Full Kitchen

Diamond Head Beach Hotel Ocean View Studio with Full Kitchen

Experience a bright and airy 11th-floor studio at the Diamond Head Beach Hotel & Residences, offering stunning ocean views, a comfortable king bed, and a fully equipped kitchen. The private lanai provides an ideal spot to unwind while enjoying breathtaking sunsets over the Pacific.
Registration Number: 310320290051, TA-034-697-0112-01, GE-034-697-0112-02

1 bedroom
1 bathroom
Sleeps 2

from $293

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Oceanfront Maui Condo with Pool and Beach Access

Oceanfront Maui Condo with Pool and Beach Access

Experience the ultimate Maui getaway in this charming oceanfront condo at Lauloa Resort, Ma'alaea. This ground-floor two-bedroom, two-bathroom home offers breathtaking sea views and direct access to miles of sandy beaches.
The spacious condo features a large lanai perfect for relaxing while watching turtles play at the sea wall or enjoying vibrant sunsets over the ocean.

2 bedroom
2 bathroom
Sleeps 4

from $413

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Stunning Ocean & Mountain View Tri-Level Home in Princeville

Stunning Ocean & Mountain View Tri-Level Home in Princeville

Discover this unique tri-level ocean and mountain view home in Princeville, beautifully maintained and fully remodeled. The expansive 5200 sq ft Redwood residence features four bedrooms plus a guest quarters with a king bed, providing comfortable accommodations for up to eight adults and two children.

5 bedroom
4 bathroom
Sleeps 10

from $1,034

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Spacious Mauna Kai 8B Condo with Stunning Views

Spacious Mauna Kai 8B Condo with Stunning Views

Welcome to Mauna Kai 8B, a spacious and beautifully updated condominium located on the North Shore of Kauai. This large unit boasts three bedrooms plus a cozy sleeping loft and three full bathrooms, making it perfect for families or groups seeking comfort and space.

4 bedroom
3 bathroom
Sleeps 8

from $500

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Charming 1-Bedroom Kona Condo Near Beaches

Charming 1-Bedroom Kona Condo Near Beaches

Experience the warmth of Hawaiian sunshine in this charming 1-bedroom, 1-bathroom condo located in Kailua-Kona. 3 miles from Honl's Beach, this quiet retreat offers easy access to Kailua-Kona’s vibrant shops, restaurants, and stunning beaches.

2 bedroom
1 bathroom
Sleeps 4

from $245

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Charming Garden-View Ground-Level Beachfront Condo in Maui

Charming Garden-View Ground-Level Beachfront Condo in Maui

Escape to this charming garden-view ground-level condo located directly on Sugar Beach, Maui’s idyllic beachfront. No roads to cross—just step outside and find yourself on the sandy shores, ready for a day of sun, surf, and relaxation.

1 bedroom
1 bathroom
Sleeps 2

from $583

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Maui Oceanfront Condo with Stunning Beach Views

Maui Oceanfront Condo with Stunning Beach Views

Experience the perfect Maui getaway in this charming oceanfront condo, ideal for up to 6 guests. The property features a spacious master loft with a luxurious king bed, an open-air design, and breathtaking ocean views from the balcony. The main-level bedroom offers two twin beds that can be converted into a king for added flexibility.

2 bedroom
2 bathroom
Sleeps 6

from $731

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Ocean View Maui Condo Near Sugar Beach

Experience the magic of Maui in this spacious ocean view condo, featuring 2 bedrooms and 2 baths. The airy living room opens through sliding glass doors to a lanai, seamlessly connecting indoor comfort with outdoor beauty, all while overlooking the stunning ocean and vibrant sunset views.

2 bedroom
2 bathroom
Sleeps 6

from $404

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Kealia Resort Unit 309 - Ocean Views & Beach Access

Kealia Resort Unit 309 - Ocean Views & Beach Access

Experience the breathtaking beauty of Kealia Resort Unit 309, where unforgettable views and ultimate relaxation await. This charming studio features floor-to-ceiling windows showcasing stunning garden and ocean vistas, creating an awe-inspiring backdrop for your Maui escape.

1 bedroom
1 bathroom
Sleeps 2

from $243

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Ma'alaea Banyans Ocean View Condo Maui

Discover the perfect Maui getaway at Ma'alaea Banyans, a beautifully updated top-floor 2-bedroom, 2-bath condo offering stunning panoramic views of the Pacific Ocean, Haleakala Crater, Molokini, and Kaho'olawe Island. Located in the peaceful village of Ma'alaea, this condo is just 20 minutes from the airport, Kahului, Lahaina, Kihei, and other popular spots on the island.

3 bedroom
2 bathroom
Sleeps 4

from $325

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Luxury Kauai Home in Poipu with Pool & Views

Luxury Kauai Home in Poipu with Pool & Views

Welcome to one of Poipu Beach’s premier vacation destinations! Nestled on a spacious corner lot within the serene Kiahuna Golf Village, this exquisite residence offers an immersive experience in Kauai’s lush natural beauty combined with luxurious comfort.

5 bedroom
5 bathroom
Sleeps 12

from $1,248

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Luxury Garden View Condo in Princeville Kauai

Luxury Garden View Condo in Princeville Kauai

Pali Ke Kua 13 offers a peaceful retreat in lush gardens on Kauai's North Shore. This spacious two-bedroom, two-bath condo spans nearly 1,200 sq. ft. and provides breathtaking mountain and waterfall views. Just steps from the bluffs above the Pacific Ocean, it overlooks the iconic Bali Hai and stunning sunsets, making it an ideal spot for relaxation and scenic beauty.

2 bedroom
2 bathroom
Sleeps 4

from $349

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Oceanfront Maui Condo with Daily Activities Included

Oceanfront Maui Condo with Daily Activities Included

Experience the ultimate Maui vacation in this charming 1-bedroom oceanfront condo located in Honokowai, nestled between Kapalua and Kaanapali. The condo comfortably sleeps four with a king-size bed and a sleeper sofa, perfect for couples or small families.

2 bedroom
1 bathroom
Sleeps 4

from $250

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Stunning Beachfront Guest House at Maili Point, Oahu

Stunning Beachfront Guest House at Maili Point, Oahu

Immerse yourself in the tranquil beauty of Maili Point with this charming guest house on Oahu's sunny west coast. Once a Hollywood actor's favorite retreat, the property offers unparalleled ocean vistas and a peaceful, private setting. Newly installed double-paned windows ensure a quiet stay, allowing you to fully enjoy the breathtaking views of Hawaii's stunning bay.
Registration Number: 870230400000, GE-008-825-8560-01, TA-008-825-8560-01

1 bedroom
1 bathroom
Sleeps 2

from $195

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Beautiful Turtle Bay Ocean View Townhome with Pool

Beautiful Turtle Bay Ocean View Townhome with Pool

Discover this charming family-owned townhome located on the West side of Kuilima Estates at Turtle Bay, offering breathtaking views of the golf course from the lanai. This two-bedroom unit provides a perfect blend of comfort and convenience, ideal for your Hawaii getaway.

Registration Number: GE-063-469-5680-01, 570010290147, TA-063-469-5680-01

2 bedroom
2 bathroom
Sleeps 6

from $422

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Luxury Maui Vacation at Wailea Ekolu #207

Luxury Maui Vacation at Wailea Ekolu #207

Welcome to Wailea Ekolu #207, a luxurious and fully renovated ground-floor condo nestled in the heart of Wailea, Maui. This spacious suite offers breathtaking views of the Pacific Ocean and the surrounding islands of Molokini, Kaho'olawe, and Lanai, reflecting the meaning of its name, "Ekolu," which signifies "three" in Hawaiian.

2 bedroom
2 bathroom
Sleeps 4

from $506

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Waikiki Shore #1316 - Beachfront Waikiki Condo

Waikiki Shore #1316 - Beachfront Waikiki Condo

Experience the unique opportunity to stay in Waikiki Shore #1316, the only condo directly on Waikiki Beach with private access to the sands. This spacious one-bedroom unit offers 717 sqft of living space plus a 124 sqft balcony/lanai, perfect for relaxing with a stunning ocean view.
Registration Number: GE-121-591-0912-01, 260040120134, TA-121-591-0912-01

2 bedroom
1 bathroom
Sleeps 4

from $479

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Spacious 2BR Condo with Ocean & Garden Views

Spacious 2BR Condo with Ocean & Garden Views

This inviting two-bedroom condo offers stunning ocean and garden views, creating a relaxing atmosphere for your stay. The master bedroom features a comfortable king bed, while the downstairs bedroom is furnished with two extra-long twin beds. The living room includes a pull-out sofa bed, providing additional sleeping space for guests.

3 bedroom
2 bathroom
Sleeps 4

from $418

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Hiʻiaka Guesthouse in Hawaii Volcanoes National Park

Hiʻiaka Guesthouse in Hawaii Volcanoes National Park

Set on a peaceful street in historic Volcano Village, Hiʻiaka Guesthouse offers a private, romantic retreat on the second floor of a beautiful custom home surrounded by lush old-growth ʻōhiʻa forest. The property provides a unique treehouse-like experience with close contact to nature and stunning views of the tropical landscape.

2 bedroom
1 bathroom
Sleeps 4

from $238

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Waikiki Sunset Condo with Mountain & City Views

Waikiki Sunset Condo with Mountain & City Views

Aloha from Midway Vacations! Our team of local hospitality experts is committed to making your Hawaiian getaway unforgettable. When you stay at this beautifully maintained condo, you’ll enjoy a professionally cleaned, comfortable space with all the amenities you need for a relaxing vacation.
Registration Number: NUC #: 90/TVU-1271 - 1990/NUC-1438 Exp. date: 09/30/2025, TA-161-478-9120-01, GE-161-478-9120-01, 126280110165

2 bedroom
1 bathroom
Sleeps 4

from $452

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Renovated Oceanfront Condo at Kuleana Unit 415

Renovated Oceanfront Condo at Kuleana Unit 415

Experience a beautifully renovated oceanfront condo at Kuleana Unit 415, perfect for a relaxing Maui getaway. This modern one-bedroom, one-bathroom unit combines island charm with contemporary amenities, offering a peaceful retreat from everyday life.

1 bedroom
1 bathroom
Sleeps 2

from $332

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Luxury Villa in Ko Olina with Private Lanai

Luxury Villa in Ko Olina with Private Lanai

Welcome to your dream vacation at this stunning villa nestled in the peaceful Hillside Villa neighborhood of Ko Olina, Hawaii. Perfectly suited for families and friends, this spacious 3-bedroom property comfortably accommodates up to six guests, offering a blend of comfort, privacy, and convenience.
Registration Number: 910560130101, GE-190-223-2576-01, TA-190-223-2576-01

3 bedroom
3 bathroom
Sleeps 6

from $658

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Ohia Kai Hale Vacation Rental Near Mormon Temple

Ohia Kai Hale Vacation Rental Near Mormon Temple

The Ohia Kai Vacation Rentals offer a peaceful retreat just steps from popular attractions. This Hale unit is situated on a tranquil street across from the Mormon Temple, providing a serene setting for your stay. The property features a charming Front Cottage and the Hale unit, with convenient parking for both renters and owners who live on-site.

2 bedroom
1 bathroom
Sleeps 4

from $450

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Beautiful Kaanapali Plantation 8 with Ocean Views

Beautiful Kaanapali Plantation 8 with Ocean Views

Experience the perfect Maui vacation at Kaanapali Plantation 8, a beautifully remodeled 2-bedroom, 2-bath condo nestled in lush tropical grounds on West Maui's hillside. This peaceful, Hawaiian plantation-style property offers breathtaking ocean and outer island views, making it an ideal retreat for families, couples, or groups seeking relaxation and adventure.

3 bedroom
2 bathroom
Sleeps 6

from $348

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Maui Sunset Oceanfront Top Floor Condo with View

Maui Sunset Oceanfront Top Floor Condo with View

Welcome to your perfect Maui getaway at the Maui Sunset Oceanfront Resort! This top-floor 671 sq ft condo offers breathtaking ocean views, including a glimpse of the volcano, and has been recently remodeled with tiled baths and flooring throughout.

1 bedroom
2 bathroom
Sleeps 3

from $514

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Luxury Beachfront Estate on North Shore Oahu

Luxury Beachfront Estate on North Shore Oahu

A rare opportunity to stay in paradise on the North Shore of Oahu. This luxurious beachfront estate offers panoramic ocean views, direct beach access, and year-round sunsets. Designed for larger families or groups, the home features five bedrooms and four bathrooms, providing ample space for up to 10 guests.
Registration Number: 61010005, TA-147-196-7232-02, GE-147-196-7232-03

5 bedroom
4 bathroom
Sleeps 10

from $1,440

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Waikiki Sunset #3704 Ocean View Condo

Welcome to Waikiki Sunset #3704, a beautifully appointed one-bedroom condo offering spectacular views of the Pacific Ocean, Diamond Head, and Kapiolani Park from the 37th floor. This 564 sqft unit features a spacious lanai with a table and chairs, perfect for relaxing while taking in the stunning scenery.
Registration Number: 1565, TA-147-447-8080-01, GE-147-447-8080-01, 260280110418

2 bedroom
1 bathroom
Sleeps 4

from $354

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Beautiful Newly Renovated Hawaii Condo Near Ko Olina

Beautiful Newly Renovated Hawaii Condo Near Ko Olina

Welcome to your perfect Hawaiian retreat! Our newly renovated two-bedroom, two-bath condo offers a tranquil escape away from the crowds of Waikiki. Located in the upstairs of the Fairways community, this property provides easy access to the stunning lagoons of Ko Olina, renowned for their crystal-clear waters and peaceful ambiance.
Registration Number: GE-033-928-8064-01, TA-033-928-8064-01

2 bedroom
2 bathroom
Sleeps 4

from $222

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West Maui Oceanfront Condo at Polynesian Shores

West Maui Oceanfront Condo at Polynesian Shores

Experience the best of West Maui at Polynesian Shores, a serene oceanfront community nestled on 2 lush acres with only 52 units. This top-floor 2-bedroom, 2-bath condo offers breathtaking ocean and Molokai views from both the unit and the spacious balcony (lanai).

2 bedroom
2 bathroom
Sleeps 6

from $354

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Spacious Kihei Condo Near Kamaole Beach Park

Spacious Kihei Condo Near Kamaole Beach Park

Welcome to our spacious 818 sq ft condo in the highly acclaimed Kamaole Sands Resort, ideally located in South Kihei just across from the popular Kamaole Beach Park III. Situated in building 4 on the third floor, our unit offers a peaceful retreat away from the resort's busier areas, providing privacy and tranquility.

2 bedroom
2 bathroom
Sleeps 3

from $260

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South Maui Oceanfront Condo with Partial Views

South Maui Oceanfront Condo with Partial Views

Experience the stunning beauty of South Maui from this beautifully remodeled ground-floor condo. Located on a 5-acre oceanfront property in Kihei, this spacious one-bedroom, two-bath unit offers partial ocean views and modern comforts for a perfect vacation.

1 bedroom
2 bathroom
Sleeps 4

from $330

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Modern Ilikai Marina Studio with City Views

Modern Ilikai Marina Studio with City Views

Experience the vibrant city life from this modern studio at Ilikai Marina, perfectly positioned at the gateway of Waikiki. The spacious open layout features large windows that flood the space with natural light, highlighting the stunning city and mountain views.
Registration Number: GE-165-379-6864-01, TA-165-379-6864-01

2 bedroom
1 bathroom
Sleeps 3

from $348

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Waikiki Ocean View Studio with Rooftop Pool

Waikiki Ocean View Studio with Rooftop Pool

Aloha from Midway Vacations! Discover this beautifully remodeled, east-facing studio on the 22nd floor in Waikiki, offering stunning ocean vistas you have to see to believe. Designed to host up to 3 guests, this unit is nestled in the heart of historic Waikiki at the Pacific Monarch, just a three-minute walk from the famous beaches with warm sands and azure waters.
Registration Number: 260230560138, GE-168-854-9888-01, TA-168-854-9888-01

2 bedroom
1 bathroom
Sleeps 3

from $508

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Sugar Beach Resort 106 Maui Beachfront Condo

Sugar Beach Resort 106 Maui Beachfront Condo

Escape to Sugar Beach Resort 106, a beautiful beachfront condo on Maui offering spectacular ocean views and direct access to five miles of white-sand beaches. This condo provides a perfect home-away-from-home experience with a private lanai, fully-equipped kitchen, and modern conveniences including free WiFi and a washer/dryer.

2 bedroom
1 bathroom
Sleeps 4

from $268

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Luxury Oceanfront Condo in Poipu Beach with Views

Luxury Oceanfront Condo in Poipu Beach with Views

com, offering stylish boutique hotel-style condos and homes designed for comfort and elegance. Our oceanfront condo in the heart of Poipu Beach provides unobstructed views of the Pacific Ocean from both the living room and the master bedroom, creating a stunning backdrop for your vacation.

2 bedroom
3 bathroom
Sleeps 6

from $653

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Beautiful Princeville End Unit with AC and Pool

Beautiful Princeville End Unit with AC and Pool

Immerse yourself in the stunning natural beauty of Kauai with this beautifully furnished end unit townhouse located in Princeville. Positioned next to the renowned Princeville Makai Golf Course, this property offers the perfect blend of comfort and convenience for couples, families, and friends seeking a tropical escape.

3 bedroom
3 bathroom
Sleeps 6

from $576

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Ocean View 1-Bedroom Condo at Lae Nani Kauai

Ocean View 1-Bedroom Condo at Lae Nani Kauai

Immerse yourself in the breathtaking ocean views of Lae Nani from this beautifully renovated third-floor unit. The light, airy decor and laminate floors create a welcoming atmosphere, complemented by a new king-sized bed for restful nights. 5-bath condo offers a private lanai ideal for morning coffee or afternoon cocktails while soaking in the ocean breeze.

1 bedroom
2 bathroom
Sleeps 2

from $373

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Charming Garden Condo Near Keawakapu Beach Maui

Charming Garden Condo Near Keawakapu Beach Maui

This charming garden condo is located on the first floor of the south side of the building, offering privacy and easy access to the outdoor space. Just about 60 steps along the pathway leads you to the breathtaking Keawakapu Beach, renowned for its soft golden sands, clear waters, and lush surroundings.

2 bedroom
2 bathroom
Sleeps 4

from $654

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Legal Short Term on North Shore Oahu, Upper Floor - Kuilima Estates

Legal Short Term on North Shore Oahu, Upper Floor - Kuilima Estates

Welcome to this beautifully updated two-bedroom condo nestled on the peaceful east side of Kuilima Estates at Turtle Bay. This inviting unit features modern touches like new tile flooring in the living room and kitchen, along with fresh kitchen cabinetry.
Registration Number: GE-102-829-8752-01, 570010270083, TA-102-829-8752-01

2 bedroom
4 bathroom
Sleeps 6

from $445

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Luxury Kauai Condo Near Makai Golf Course

Luxury Kauai Condo Near Makai Golf Course

Discover this luxurious Kauai condo nestled next to the iconic Makai Golf Course at the Princeville Resort. This intimate resort offers only 42 units, creating a peaceful retreat with amenities like a swimming pool, spa, and outdoor barbecue area.

2 bedroom
2 bathroom
Sleeps 4

from $454

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