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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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Beautiful Waikiki Condo with Ocean Views & Amenities

Beautiful Waikiki Condo with Ocean Views & Amenities

Experience the perfect Hawaiian getaway in this beautifully maintained Waikiki condo, offering stunning peek-a-boo ocean views and a prime location just minutes from Waikiki Beach. ft. plus a lanai, this unit comfortably accommodates up to 4 guests with a cozy king bed, queen sleeper sofa, and modern amenities.
Registration Number: TA-138-189-2096-01, GE-138-189-2096-01, 260170570136

2 bedroom
1 bathroom
Sleeps 4

from $285

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Kiahuna Plantation 420 - Garden View Condo in Kauai

Kiahuna Plantation 420 - Garden View Condo in Kauai

Discover the beauty of Kauai at Kiahuna Plantation 420, a charming ground-floor condo nestled amidst 35 acres of lush lawns and tropical gardens. This historic property, once part of Hawaii's sugar plantation era, offers a perfect blend of natural beauty and modern comfort.

2 bedroom
1 bathroom
Sleeps 4

from $410

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Luxurious Hualalai Estate with Pool and Ocean Views

Luxurious Hualalai Estate with Pool and Ocean Views

Experience the ultimate Hawaiian retreat in this spectacular estate at Hualalai Resort. 5 bathrooms, each with luxurious en-suite facilities, including dual vanities, bathtubs, and outdoor garden showers. The primary suite offers ocean vistas, a king bed, smart TV, and direct access to a lanai, creating a perfect sanctuary.

4 bedroom
5 bathroom
Sleeps 8

from $4,028

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Renovated Condo Near Punaluu Beach and Volcanoes

Renovated Condo Near Punaluu Beach and Volcanoes

This charming condo is part of a small, well-maintained community with approximately 70 units. Guests can enjoy amenities like a pool, hot tub, and grills in a lush, landscaped setting. Although the condo overlooks SeaMountain Golf Course, please note the course is currently closed until further notice.

2 bedroom
1 bathroom
Sleeps 4

from $173

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Charming Kauai Townhome with Pool and Spacious Living

Charming Kauai Townhome with Pool and Spacious Living

This tastefully decorated second-floor townhome offers nearly 2000 square feet of comfortable living space, combining style and functionality. The interior boasts artistic touches and high-quality furnishings, ensuring a luxurious stay. With two spacious lanais, you can enjoy outdoor relaxation and scenic views, perfect for morning coffees or evening cocktails.

3 bedroom
3 bathroom
Sleeps 6

from $560

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Poipu Ocean View Condo with Stunning Pacific Vistas

Poipu Ocean View Condo with Stunning Pacific Vistas

Escape to this beautiful contemporary condo located on the second floor, offering breathtaking views of the Pacific Ocean. Inside, enjoy modern furnishings and a spacious living area that opens onto a private lanai, where you can unwind while watching sea turtles, playful dolphins, and majestic humpback whales.

2 bedroom
2 bathroom
Sleeps 4

from $512

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Hawaii Two-Bedroom Suite with Aloha & Turtle Rooms

Hawaii Two-Bedroom Suite with Aloha & Turtle Rooms

Discover our charming two-bedroom suite designed for 2-4 guests, offering a cozy Hawaiian ambiance. The suite features the Aloha Room on the upper main level, which boasts a luxurious king-size bed, in-room cable TV, DVD player, and private lanai access.

2 bedroom
1 bathroom
Sleeps 4

from $438

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Spacious 14th Floor Condo at Ilikai Hotel

Spacious 14th Floor Condo at Ilikai Hotel

Experience the comfort and convenience of this spacious condo on the 14th floor of the Ilikai Hotel in Waikiki. Covering over 500 sq ft, this unit is ideal for couples, friends, or families seeking a relaxing island getaway. Recent upgrades include new vinyl flooring, replacing carpets, and providing a fresh, modern feel.
Registration Number: GE-147-357-9008-01, TA-147-357-9008-01

2 bedroom
1 bathroom
Sleeps 4

from $370

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Luxury 3-Bedroom Mauna Lani Vacation Home

Luxury 3-Bedroom Mauna Lani Vacation Home

5-bath vacation home located within the prestigious Mauna Lani Resort. This luxurious property offers a perfect blend of comfort, elegance, and exclusive amenities, making it an ideal choice for families, couples, or groups seeking a memorable island retreat.

3 bedroom
4 bathroom
Sleeps 6

from $550

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Cozy Ocean-View Studio at Maui Kaanapali Villas

Cozy Ocean-View Studio at Maui Kaanapali Villas

Experience the ideal Hawaiian escape at Maui Kaanapali Villas in this cozy ocean-view studio. Located just steps from the pristine beach and surrounded by lush gardens, this villa offers a perfect blend of comfort, luxury, and convenience.

2 bedroom
1 bathroom
Sleeps 2

from $891

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Oceanfront Condo at Sugar Beach Resort Kihei

Oceanfront Condo at Sugar Beach Resort Kihei

Welcome to Sugar Beach Resort #130, your perfect oceanfront getaway in North Kihei! This beautifully maintained condominium offers breathtaking Pacific Ocean views and easy access to a pristine beach. The resort features two six-story buildings with elevators, making it convenient to enjoy stunning sunsets, swimming, windsurfing, leisurely beach walks, and seasonal whale watching.

2 bedroom
1 bathroom
Sleeps 4

from $321

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Hana Kai Maui Unit 203 Ocean View Retreat

Hana Kai Maui Unit 203 Ocean View Retreat

Experience the tranquility and natural beauty of Hana in 'Lanakila' Unit 203, a charming upper-floor one-bedroom, one-bath condo nestled in Hana Kai Maui's Mauka building. This spacious unit combines comfort with tropical elegance, featuring an open kitchen with koa accents, hardwood floors, stainless steel appliances, and granite countertops that create a warm, inviting atmosphere.

2 bedroom
1 bathroom
Sleeps 4

from $484

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Oceanfront Garden View Condo at Pono Kai Resort

Oceanfront Garden View Condo at Pono Kai Resort

Pono Kai Resort, nestled on a stunning oceanfront property in the heart of Kapaa, Kauai, offers this inviting third-floor garden view condo. The unit features a comfortable king-sized bed in the bedroom and a pull-out queen sleeper sofa in the living room, making it perfect for couples or small families.

2 bedroom
1 bathroom
Sleeps 4

from $267

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Beautiful Ground Floor Ocean View Condo in Lae Nani

Beautiful Ground Floor Ocean View Condo in Lae Nani

Discover this beautifully renovated ground floor condo at Lae Nani, offering stunning ocean views and modern amenities. Stay cool with split system AC and enjoy the refreshing ocean breeze through the lanai door. Located just steps from the beach, pool, and BBQ areas, this unit provides the perfect setting for a relaxing getaway.

2 bedroom
2 bathroom
Sleeps 6

from $476

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Beautiful Ocean View Condo in Kailua-Kona

Beautiful Ocean View Condo in Kailua-Kona

Discover this stunning, fully furnished three-bedroom condo in Kailua-Kona offering breathtaking ocean views and modern comforts. Located just a three-minute walk from the waterfront, guests can enjoy spectacular sunsets and easy access to some of Hawaii's most beautiful white sand beaches.

4 bedroom
3 bathroom
Sleeps 8

from $324

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Beautiful Ocean View Condo at Shores of Maui

Beautiful Ocean View Condo at Shores of Maui

The Shores of Maui offers a charming condominium community in a prime location right across from Cove Beach Park in Kihei. This condo features breathtaking ocean views visible from both the living room and the spacious private lanai, making it an ideal spot for relaxing and soaking in Maui’s natural beauty.

2 bedroom
1 bathroom
Sleeps 5

from $330

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Oceanfront 2-Bedroom Villa with Panoramic Views in Maui

Oceanfront 2-Bedroom Villa with Panoramic Views in Maui

Experience the ultimate Maui getaway in this beautiful oceanfront 2-bedroom villa featuring dual lanais with stunning panoramic views of Molokai and Lanai. The spacious townhouse-style unit comfortably hosts up to 6 guests, making it ideal for families or groups seeking luxurious island living.

3 bedroom
2 bathroom
Sleeps 6

from $1,902

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Waikiki Ocean View Studio at Colony Surf

Waikiki Ocean View Studio at Colony Surf

This fully furnished studio at Colony Surf offers an unbeatable location on the east end of Waikiki, just minutes from Diamond Head and nearby shops, restaurants, and attractions. Situated on the 19th floor, the unit provides breathtaking unobstructed ocean views, including spectacular sunrises, sunsets, and Friday night fireworks, all visible from the comfort of your space.
Registration Number: TA-159-695-6672-01, GE-159-695-6672-01, 310320100156

1 bedroom
1 bathroom
Sleeps 2

from $123

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Surfer Hale - Kuilima Estates East # 1

Experience the laid-back charm of this beautiful downstairs end unit at Kuilima Estates East, located near Turtle Bay on Oahu's North Shore. The condo features authentic Hawaiian decor with natural wood and rattan furniture, complemented by tropical colors that evoke the island's spirit.

Registration Number: TA-155-037-9008-01, GE-155-037-9008-01, 570010270001

2 bedroom
1 bathroom
Sleeps 2

from $371

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Luxury Turtle Bay Hawaii Condo - Remodeled unit at Kuilima East

Luxury Turtle Bay Hawaii Condo - Remodeled unit at Kuilima East

Welcome to our beautifully renovated upscale condo located on Oahu's stunning North Shore. This fully air-conditioned unit offers mountain and golf course views, complemented by a refreshing tropical breeze, and is nestled within a safe, family-friendly community.
Registration Number: GE-010-632-8064-02, STR #23, TA-010-632-8064-02, 570010270021

2 bedroom
1 bathroom
Sleeps 4

from $526

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Poipu Sands 222 Ocean-View Condo Near Beaches

Poipu Sands 222 Ocean-View Condo Near Beaches

Welcome to Poipu Sands 222, a beautifully designed two-story condo nestled on the lush Poipu Kai Greenbelt, offering stunning ocean views from multiple lanais. This tropical retreat is ideal for families, couples, or friends looking for a relaxing getaway with plenty of adventure options within easy reach.

2 bedroom
2 bathroom
Sleeps 4

from $535

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Stunning Hawaii Condo with 360° Ocean & Mountain Views

Stunning Hawaii Condo with 360° Ocean & Mountain Views

Come enjoy your Hawaii vacation at our beautifully remodeled condo. The spectacular views from the wrap-around balcony offer a 360-degree panorama of the ocean and mountains. This spacious unit has been decorated with a personal touch, creating a welcoming and stylish atmosphere.
Registration Number: TA-092-737-3312-01, GE-092-737-3312-01

1 bedroom
3 bathroom
Sleeps 2

from $286

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Hanalei Beach House Oceanfront Vacation Retreat

Hanalei Beach House Oceanfront Vacation Retreat

The Hanalei Beach House offers an unparalleled oceanfront experience on a spacious half-acre lot just steps from the sandy shores of Hanalei Bay. Surf the gentle, beginner-friendly waves right in front at Kiddies surf spot, perfect for families and beginners alike.

2 bedroom
2 bathroom
Sleeps 4

from $1,255

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Spacious 3BR Poipu Beach Vacation Home

Enjoy a memorable stay in this spacious 3-bedroom, 2-bath home located at the end of a quiet cul-de-sac in a prestigious Poipu neighborhood. Spanning 1800 sqft on a single level, it offers a comfortable, accessible layout without stairs. The highlight is the outdoor atrium, nestled in the center of the home, with double French doors opening to a private, fully fenced backyard perfect for barbecues and outdoor relaxation.

3 bedroom
3 bathroom
Sleeps 6

from $969

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Oceanfront Condo at Sands of Kahana with Free Activities

Oceanfront Condo at Sands of Kahana with Free Activities

Experience an unforgettable Maui vacation at Sands of Kahana 316, a spacious 2-bedroom, 2-bathroom oceanfront condo that comfortably sleeps 6 guests. This modern, open-concept unit offers breathtaking direct ocean views from the third-floor lanai, perfect for relaxing and enjoying the island's beauty.

2 bedroom
2 bathroom
Sleeps 6

from $465

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Bright Oceanfront 2BR Condo with Sunset Views in Maui

Bright Oceanfront 2BR Condo with Sunset Views in Maui

This charming ground-floor 2-bedroom, 2-bath condo offers a bright, airy space perfect for your Maui getaway. Located on South Maui, it provides easy access to beautiful beaches, local shops, and delicious dining options just steps from your door.

3 bedroom
2 bathroom
Sleeps 7

from $415

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Charming 3-Bed Maui Townhome Near Beach & Pool

Charming 3-Bed Maui Townhome Near Beach & Pool

Relax and unwind at Puamana 80-2, a beautifully updated three-bedroom townhome nestled on the south shore of Maui. This spacious and modern vacation home offers a perfect blend of comfort and convenience for your tropical escape. The expansive private lanai overlooks a lush greenbelt, creating an ideal setting for outdoor dining, grilling, or simply soaking up the island ambiance.

3 bedroom
3 bathroom
Sleeps 6

from $486

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Beautiful Oceanfront 2BR Condo at Papakea Maui

Beautiful Oceanfront 2BR Condo at Papakea Maui

Welcome to G404 at Papakea Oceanfront Resort, a stunning top-floor 2BR condo nestled on Maui's North Kaanapali Beach. This beautifully renovated unit offers breathtaking views of the Pacific Ocean, Molokai, and Lanai, making it an ideal retreat for families, couples, or friends seeking the perfect Hawaiian getaway.

2 bedroom
1 bathroom
Sleeps 6

from $926

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Sunset Kahili 403 Ocean View Condo in Poipu

Sunset Kahili 403 Ocean View Condo in Poipu

Located in the heart of sunny Poipu, Sunset Kahili 403 offers breathtaking panoramic ocean views from its fourth-floor vantage point. This fully refurbished and tastefully decorated condo combines comfort with style, ensuring a relaxing stay. The bedroom features a cal-king bed and a full en-suite bathroom with a sliding privacy screen, providing flexibility and privacy.

1 bedroom
1 bathroom
Sleeps 2

from $346

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Oceanfront Kona Bay View Condo with Pool & Hot Tub

Oceanfront Kona Bay View Condo with Pool & Hot Tub

Experience the beauty of Kona from this charming second-floor oceanfront condo, recently upgraded to ensure a comfortable stay. The unit boasts new mattresses, modern mini-split A/C units in both bedrooms, and a standalone A/C in the living room, providing cool comfort during warm days.

3 bedroom
2 bathroom
Sleeps 6

from $329

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Luxury Maui Kapalua Golf Villa with Ocean Views

Luxury Maui Kapalua Golf Villa with Ocean Views

5-bathroom condo. The spacious living area features stunning views of the lush green golf course and the vast Pacific Ocean, creating a perfect backdrop for your Maui getaway.
The well-appointed kitchen is equipped with granite countertops, stainless steel appliances, olive oil, salt & pepper, and essential cookware, making meal preparation a breeze.

2 bedroom
2 bathroom
Sleeps 2

from $400

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Oceanfront Hale Kai Condo in West Maui

Welcome to our charming #104 Ocean Front "home by the sea" in West Maui. This unique condo offers a nostalgic glimpse of old Hawaii, with vibrant tropical decor and breathtaking ocean views visible from the kitchen, living room, and dining area through reflecting mirrors.

2 bedroom
1 bathroom
Sleeps 4

from $213

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Beachfront Garden Apartment at Paki Maui, Maui

Beachfront Garden Apartment at Paki Maui, Maui

Located on the northern end of the renowned Kaanapali Beach, Paki Maui offers a tranquil retreat with direct ocean access, a sandy beach, and a double-reef safe for swimming and snorkeling. The complex features four stories with three buildings, totaling 108 units, and includes a lush lawn area where you can relax under palm trees and enjoy views of Molokai and Lanai.

1 bedroom
1 bathroom
Sleeps 4

from $147

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Modern Oceanfront 1-Bedroom Retreat on Sugar Beach

Modern Oceanfront 1-Bedroom Retreat on Sugar Beach

Welcome to your perfect Maui getaway in this beautifully remodeled oceanfront condo on Sugar Beach. This one-bedroom, two-bathroom unit combines modern comforts with breathtaking views, making it an ideal retreat for relaxation and adventure.

2 bedroom
2 bathroom
Sleeps 4

from $396

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Valley Isle 208: Oceanfront Maui Condo with Free Activities

Valley Isle 208: Oceanfront Maui Condo with Free Activities

Escape to Valley Isle 208, a beautifully renovated oceanfront condo in Kahana, Maui, offering breathtaking direct ocean views from the master bedroom and living room. This spacious 2-bedroom, 2-bathroom unit comfortably sleeps six, featuring king beds in both bedrooms, a queen Murphy bed in the living room, and large flat-screen smart TVs in all rooms.

3 bedroom
2 bathroom
Sleeps 6

from $367

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Remodeled 2BR Oceanview Suite at Kaanapali Alii

Remodeled 2BR Oceanview Suite at Kaanapali Alii

Immerse yourself in the luxury of suite 274 at Kaanapali Alii, a beautifully remodeled 2-bedroom condo offering stunning partial ocean and West Maui Mountain views from the 7th floor. Recent upgrades include a new sectional queen sofa sleeper, a modern dining table, and smart TVs for your entertainment.

3 bedroom
2 bathroom
Sleeps 6

from $918

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Luxury Geodesic Home Near Hawaii Volcano National Park

Luxury Geodesic Home Near Hawaii Volcano National Park

This exquisite 2,000 sq ft geodesic home offers a luxurious retreat set on two private acres amidst the vibrant rainforest of Hawaii. The property boasts lush tropical gardens filled with the soothing sounds of coquis and native Hawaiian birds, creating a peaceful and rejuvenating atmosphere.

4 bedroom
3 bathroom
Sleeps 10

from $426

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Luxury Oceanfront Retreat with Bay Views in Kauai

Luxury Oceanfront Retreat with Bay Views in Kauai

Experience the ultimate Kauai escape from this private oceanfront retreat perched on a seaside cliff. Just steps from Kalapaki Beach, guests can indulge in kayaking, surfing, or simply relax while soaking in incredible views overlooking Nawiliwili Harbor from the comfort of their private balcony.

2 bedroom
2 bathroom
Sleeps 4

from $785

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Hale Pohaku 3 Oceanfront Condo with Panoramic Views

Hale Pohaku 3 Oceanfront Condo with Panoramic Views

Welcome to Hale Pohaku 3, a beautifully remodeled, stylish condo managed by Kona Coast Vacations. This stunning two-bedroom, two-bathroom property offers an elevated 180-degree view of the azure Pacific Ocean, perfect for those seeking a luxurious and relaxing getaway.

2 bedroom
2 bathroom
Sleeps 4

from $447

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Family-Friendly Tropical Condo with Pool and Garden Views

Family-Friendly Tropical Condo with Pool and Garden Views

Escape to this charming, budget-friendly tropical condo perfect for families seeking a relaxing getaway. The fully equipped kitchen boasts new granite counters, while the cozy living room features fresh furniture and a flat-screen TV with Bluetooth speaker.

2 bedroom
2 bathroom
Sleeps 4

from $300

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Hanalei Bay Resort Studio with Ocean Views

Hanalei Bay Resort Studio with Ocean Views

Discover the charming Hanalei Bay Resort unit 7101, affectionately known as "Honu Hideaway," a beautifully upgraded and meticulously maintained studio condo designed for comfort and relaxation. This private retreat offers a cozy living space with modern furnishings, a inviting breakfast bar featuring bamboo cabinets, granite countertops, and a Keurig coffee maker, perfect for starting your day.

1 bedroom
1 bathroom
Sleeps 3

from $348

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Charming 2BR Condo Near Charley Young Beach

Charming 2BR Condo Near Charley Young Beach

Experience the perfect island retreat in this beautifully remodeled two-bedroom, two-bath condo located in the heart of South Kihei. The property boasts a stunning renovation with modern touches, including waterproof vinyl flooring, Caesarstone countertops with a waterfall edge, new cabinetry, appliances, and stylish beach-inspired furnishings.

3 bedroom
2 bathroom
Sleeps 6

from $288

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Alii Point Oceanfront Vacation Home in Kona

Alii Point Oceanfront Vacation Home in Kona

Welcome to your dream Hawaiian escape at Alii Point, a lush private community just two miles south of Kailua-Kona. This beautifully updated oceanfront residence offers breathtaking coastal views, modern comfort, and a tropical paradise setting.

4 bedroom
3 bathroom
Sleeps 8

from $1,191

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Beachfront Maui Deluxe Suite at Kahana Reef

Beachfront Maui Deluxe Suite at Kahana Reef

Step into this beautifully renovated ground-floor deluxe suite at Kahana Reef, offering a perfect blend of island charm and modern comfort for your Maui vacation.
The unit features a spacious living area with plush furnishings, a new flat-screen TV, and a pull-out sofa for extra seating.

2 bedroom
1 bathroom
Sleeps 2

from $300

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Renovated Diamond Head Beach Hotel Studio Suite

Renovated Diamond Head Beach Hotel Studio Suite

Experience a beautifully renovated studio suite at the Diamond Head Beach Hotel, completed in 2024. Located on the 5th floor with stunning garden rooftop views, this cozy yet luxurious space offers a king bed with Tommy Bahama pillows, a queen sleeper sofa, and modern amenities including a new AC unit, TV with HD cable, and high-speed WiFi.
Registration Number: TA-212-173-8240-01, 310320290022, GE-212-173-8240-01

0 bedroom
1 bathroom
Sleeps 2

from $235

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Casa de Emdeko Kona Coast Vacation Rental

Casa de Emdeko Kona Coast Vacation Rental

Experience the perfect Hawaiian escape at Casa de Emdeko, the Crown Jewel of the Kona Coast. This inviting condo offers stunning garden views and easy access to the saltwater pool and oceanfront lounging areas. With a comfortable king-sized bed in the bedroom and a sofa sleeper in the living room, it’s ideal for families or groups.

2 bedroom
1 bathroom
Sleeps 4

from $189

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Luxury Penthouse at Puu Poa with Ocean Views

Luxury Penthouse at Puu Poa with Ocean Views

Enter through elegant teak and carved-glass doors into the first of two lanais, offering breathtaking views of the majestic Pacific Ocean. PUU POA 406 welcomes you with a tropical decor that has been recently refreshed, featuring a spacious and beautifully furnished family room that beckons relaxation.

2 bedroom
2 bathroom
Sleeps 4

from $650

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Beautiful Maui Condo Near Beach with Pool & Views

Beautiful Maui Condo Near Beach with Pool & Views

Welcome to your perfect Maui vacation at Pacific Shores! This beautifully refurbished condo is located south of central Kihei, just north of Wailea, offering easy access to some of the island's best beaches, shopping, and dining options.

The condo features 2 bedrooms and 2 bathrooms, comfortably sleeping 4-5 guests.

3 bedroom
2 bathroom
Sleeps 5

from $282

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Maui Kamaole B102 Luxury Kihei Condo with Views

Maui Kamaole B102 Luxury Kihei Condo with Views

Maui Kamaole B102 offers a perfect blend of luxury and privacy in a beautifully landscaped Kihei setting. This spacious condo is located within the renowned Maui Kamaole resort, just minutes from the sun-kissed Kamaole beaches, including Kamaole Beach Park III across South Kihei Road, renowned for swimming, snorkeling, and sunbathing.

2 bedroom
2 bathroom
Sleeps 4

from $356

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Beachfront Condo at Kamaole Sands 7-102 in Kihei

Beachfront Condo at Kamaole Sands 7-102 in Kihei

Experience the ultimate Maui vacation at Kamaole Sands 7-102, a beautifully appointed ground-floor condo located just across from the renowned Kamaole III Beach in Kihei. This inviting 1-bedroom, 2-bath residence is ideal for families or couples seeking a tropical escape.

2 bedroom
2 bathroom
Sleeps 4

from $298

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