Hawaii Vacation Rentals – Island Condos, Beachfront Homes & Luxury Villas
Welcome to your guide for Hawaii vacation rentals, where tropical luxury meets everyday comfort. From sunrise-facing lanais on Maui to private bungalows near the lush valleys of Kauai, each rental is handpicked for quality, location, and local charm.
Why Book a Vacation Rental in Hawaii?
Unlike traditional hotels, vacation rentals provide full kitchens, private lanais, and dedicated living space—ideal for families, couples, or long stays. Many homes are steps from the beach, offer high-speed Wi-Fi, and include perks like pools, BBQ areas, or resort access.
Popular Vacation Rental Locations
- Waikiki, Oahu – High-rise condos near beaches, shops & nightlife
- Kihei, Maui – Walkable, affordable, and family-friendly
- Princeville, Kauai – Scenic cliffs, golf, and luxury condos
- Kailua-Kona, Big Island – Oceanfront escapes with sunset views
Rental Types Available
- Beachfront Condos with resort amenities
- Private Beach Homes with full kitchens
- Luxury Villas with pools & panoramic views
- Studios & Bungalows for solo travelers or couples
What Makes To-Hawaii.com Rentals Stand Out?
- Verified properties across all major Hawaiian islands
- Detailed descriptions, amenities, and photo galleries
- Helpful internal links to top Hawaii activities and Hawaii rental cars
- Flexible booking options, from weekend getaways to long-term stays
Plan Your Dream Island Escape
Explore the beauty of the islands with confidence. Whether you're whale watching on Maui, snorkeling on Oahu, or enjoying a peaceful sunrise on Lanai, our vacation rentals offer the perfect base for unforgettable memories. Start planning your Hawaiian adventure today.
Prime views on top row villa-5 stars-crisp cold AC-Discounted Rates-Book Now
Welcome to "Hale Kailani,” which translates to “home of the heavenly sea.”Hale Kailani is one of the premier villas in the exclusive Kapalua Golf Villas. Our villa boasts stunning views of the Pacific Ocean. Sitting just off one of Kapaluas' two championship golf...
Spectacular Oceanfront Condo at Hideaways Beach, Bali Hai Views, AC all rooms
Experience spectacular ocean views and dazzling sunsets, in your private luxury vacation residence. This condo is on the second level six steps down with ocean and mountain views. A/C in all rooms, both bedrooms and the open concept kitchen living room area. Our...
The Premier Waikoloa Stay at Halii Kai
Hali'i Kai is one of the most sought out places to stay while visiting the Kohala Coast on Big Island. It features meticulous well kept grounds, beautiful and comfortable living spaces along with a luxurious amenity center, the Ocean Club. The Ocean Club features its...
Gorgeous condo #203 View of Honokeana Cove
Unit 203 is a 2nd floor, Northwest facing unit that enjoys shade year round on the lanai that directly overlooks the cove with turtles, the heated pool, and a spectacular view of the island of Molokai in the distance as well as Humpback whales December thru April. The...
Exclusive Beachfront Home in Private Gated Community
Welcome to Hale 4 U! Step through the front door and be captivated by breathtaking panoramic views of one of the most unique coastlines in the Hawaiian Islands. Nestled within an exclusive gated community with access to a private bay, this beachfront retreat offers 5...
Enjoy breathtaking ocean views and a genuine taste of island living.
Discover the magic of Belle Vue Kona B&B, a hidden gem perched in a one-of-a-kind location overlooking the historic Kealakekua Bay. Here, you’ll enjoy breathtaking views of the Pacific Ocean and the panoramic beauty of the South Kona coastline. Set on a lush four-acre...
Maui Resort Rentals: Honua Kai Konea 737 - Stunning 7th Floor Ocean View Studio!
Boasting one of the absolute best vantage points of any studio on offer at Honua Kai, this outstanding ocean-view suite will impress from the moment you enter. From its optimal orientation toward the ocean to its ideal 7th-floor vantage point, your group will enjoy...
OCEAN FRONT PRIVATE RESIDENCE AT KEAUHOU BAY WITH POOL & PRIVATE DOCK
Enjoy everything Hawaii has to offer in a very private three-acre estate on the shore of historic Keauhou Bay, six miles south of Kailua Kona on the Big Island of Hawaii. Called “Hale Kai” (house by the sea), you will be surrounded by lawns and lush tropical gardens...
SALE April-May! Top Floor Maui Vista with Ocean View, AC, 5min Walk to Beach
Welcome to your dream tropical paradise! Bask in the glory of gorgeous sunsets right from your own living room or lanai. Centrally located in the heart of Kihei, this 2bd/2ba top floor, 2-story loft condo is across the street from Charley Young/Kamaole 1 beach and...
Oceanfront Views Above Dukes - Wrap Around Lanai - Outdoor Kitchen 🌺 Honua Kai H351
🌊 Oceanfront Views Above Dukes - Enjoy Evening Music - Wrap Around Lanai - Outdoor Kitchen 🌺Discover your dream escape at Honua Kai Resort & Spa, where unparalleled oceanfront views, lush surroundings, and refined luxury come together. Positioned right in front of...
20% off on regular rate! Ocean View Penthouse/ Free Parking.. walk to the beach
** On-site Parking and High Speed Wifi****** 30 Day Minimum Stay. Visit us at www.topofbigsurf.comEnjoy 25% off your monthly stay at this peaceful, fully furnished 1-bedroom condo!Your Peaceful, Stylish Home Base in Waikiki – Ideal for Remote Work + Long-Term...
HOKULANI 436-CORNER UNIT 2BD/2BA w/OCEAN & MOUNTAIN VIEWS,505SQFT LANAI BALCONY
Unique and Large 2BD/2BA large corner unit on 4TH floor - Unit 436 in Hokulani building 1,745 Total Sqft - 1,240 living space + 505sqft lanai (much larger than the typical Honua Kai lanai)Family Friendly: Kids and grownup beach toys, Kids & Grownup DVD's, Kids and...
Modern Oasis w/Hot Tub, 5 min walk to Anini Beach
A stylish reimagining of our ever-popular Coconut Hut. This perfectly positioned gem sits in a secluded park-like paradise within a 5-minute walk to the idyllic Anini beach. With new construction, the house contains hardwood floors, whole house water filtration, AC in...
Kawela Kai on the Beach
Beautiful Home on 1/2 acre Property with own private driveway. Large manicured Lawn faces Swimming Lagoon directly in front of Property. Year round sunsets can be enjoyed from the Deck and yard. Old style barbecue with picnic tables is located right next to the beach....
Oceanview Mauna Kea Luxury Villa - Private Pool & Spa - In-home Chefs Available
Aloha, picture yourself in paradise! Less than 30 minutes from the Kona airport, this beautiful three bedroom Villa provides the perfect location to enjoy all that the Big Island has to offer. Located in prestigious Wai'ula'ula, just minutes from one of the most...
Villages at the Mauna Lani Resort 🌺 Walk to Mauna Lani Restaurants & Shops
Welcome to the Villages at the Mauna Lani Resort!"Originally the ancestral beach front home of Hawaiian royalty, the 3,200-acre Mauna Lani Resort now offers an exquisite blend of sophisticated luxury and Hawaiian-style hospitality. Mauna Lani Resort is just 25 minutes...
Updated condo with furnished lanai & washer/dryer plus pool & tennis
Hale Kamaole 144Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'This ground-floor getaway is a bright and spacious oasis located just steps from the ocean! Enjoy evenings watching...
Hale La'au Hawanawana: Luxury 3BR Estate in Princeville
Hale La’au Hawanawana (Whispering Tree House), built in 2024!Escape to an exquisite modern oasis in the heart of Princeville, where luxury meets the lush beauty of Kauai’s North Shore. Nestled on a ½-acre of beautifully manicured land with a year-round running...
New listing discount! Beachfront 2 BR 1BA apt.
Located in central Kihei, this 2 BR 1 BA beachfront unit has all the comforts of home, including a fully stocked kitchen with a stove, oven, refrigerator, and more, perfect for whipping up delicious meals. Enjoy dinning indoor or step outside onto the balcony and dine...
Spectacular Floor-To-Ceiling Ocean View, Ground Floor For Direct Ocean Access!!!
On Kauai's sunny south shore. Floor to ceiling windows on the lanai, for the full width of the condo facing spectacular ocean views and sounds, on the side of Kuhio Shores where the giant sea turtles hang-out, with the lanai facing the trade-winds for constant comfort....
Two homes on the ocean with a private saltwater pool.
The Cliff House is has two detached structures each with its own full kitchens. The private saltwater pool is on the ocean-side with a large shaded patio. Perfect for large families, co-workers and/or friends to gather in one place but have separate, private living...
On the Ocean at Kealakekua Bay. Where the Dolphins Play.
'Okika Lani sits at the south end of Kealakekua Bay on a private road with spectacular views of the Pacific Ocean, the Captain Cook Monument, and crescent shaped, white sand Ke'ei Beach. Enter the gate at 'Okika Lani and walk into an inner courtyard of Bamboo Palms,...
Luxury Laie Beachfront Estate w/ Private Pool, Spacious Living & Ocean Access
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Welcome to Laie Beachfront Estate by Gather, a...
Kaanapali Alii | 371
Kaanapali 371 is a stunning ocean view condo on the seventh floor that enjoys fantastic views of the lagoon-style property pool and also the waves crashing on Kaanapali Beach. Tropical decor highlighted by bright watercolor paintings of bird or paradise, ginger, and...
Waikiki Sunset 3110
See my other properties #3156864 and #3197017 and #3512192 for more 5-star reviews and to book multiple condos for large groups.Located on a high floor of the Waikiki Sunset with sweeping ocean, coastline, and park views this condo offers enough beds to sleeps 6. 1...
Exquisite Oceanview and Mountainview Home with Private Pool!
This is the vacation you will always remember! Welcome to 'PARADISE POIPU', our little slice of Heaven in Kauai. Indulge your senses in this newly built, 1800 square foot home on Kauai’s SUNNY south shore. If you’re one who has an appreciation for the finer things...
MAUI OCEAN Beach FRONT AMAZING VIEWS Summer special 275 nightly
Our beautiful condo is located on the world famous Kaanapali Beach and shores. You can't get any closer to the ocean then the MAUI KAI Resort, the Bldg. Is just feet away with the best snorkeling right outside the front door. As you relax on the lanai, it's easy to...
Luxury Hawaiian Style Condo with A/C, Nihilani 16A
Nihilani 16A is a beautifully decorated 2-bedroom, 2-bath, air conditioned plantation style condo. Set in a lush, garden setting, this spacious, one-story, 1,400-square-foot home is a destination where you can retreat into the relaxed Hawaiian lifestyle in comfort and...
Diamond Head Surf House: Gold Coast Oceanfront Home w/AC & Gorgeous Views
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Completely immerse yourself into the island...
Steps to Kamaole beaches/Upgraded kitchen & baths/2 Pools/Tennis/Close to Wailea
This second floor 2 bedroom/2 bath peek-a-boo ocean view condo is your perfect Maui vacation retreat just across the street from beautiful Kamaole III beach park! Maui Kamaole is one of the lowest density projects in South Kihei and features beautiful landscaping, 2...
Spacious 5-Bedroom Oceanview House in Holualoa
Welcome to your high end private Hawaiian escape! Set on 158 lush acres in Holualoa, this serene estate offers ocean views, cool breezes, and forest trails. Perfect for families or groups, the spacious home features indoor/outdoor living, a full kitchen, cozy bedrooms,...
Hyatt Residence Club, Ka'anapali Beach, Oceanfront Resort, Beautiful Villas
Please choose a Friday through Sunday for check-in and enjoy a seven-night stay.Rates are set for Garden/Island View. Ocean view/oceanfront may be available depending on your travel dates. Thank you for choosing Dash Realty Group of Windermere, Florida. We are a...
Mermaid’s Lookout WOW the views! Ocean Front, full lanai, heated pool & AC.
Welcome to Mermaid's Lookout! This 2-bedroom efficiency home in Hawaiian Paradise Park is perfect for your escape to paradise. With 1 king and 1 split adjustable king, a deep soaking tub with two shower heads, and all the essentials like AC and WiFi, this stunning...
One-Bedroom Villa in Ocean Front Resort, all amenities and services.
The quoted base rent is in Canadian Dollars, including resort fees. Currently, the currency exchange rate is $1.0 USD = $1.4 CAD! Oceanview can be guaranteed for advanced booking of 8-12 months before the arrival date.This one-bedroom Villa (840 s.f.) in a huge...
Ma'alaea Surf Unit E4-2 BR Ground Floor Beachfront Condo, AC, Wifi, Pool, TV
Ma'alaea Surf, Unit E4, is conveniently located on the ground floor, just steps away from the large pool. It was completely remodeled recently. This unit is well furnished, features a full kitchen and a second bedroom and bath. This condo features everything including...
Oceanfront Luxury 1 BR Condominium - Perfect Honeymoon Spot!
Escape to our charming 1-bedroom condo in the heart of Wailuku(Ma'alaea Village), Maui. Nestled just a short walk from the stunning West Maui Mountains, you'll be surrounded by breathtaking natural beauty. Take a leisurely 13-minute stroll to the vibrant Maalaea Harbor,...
❤️PiH❤️ Pineapple Hale ★ Elegant Private ★ Bikes ★Free Hilton Pool & Waterslide Passes
Brought to you by Paradise in Hawaii Luxury Homes.Welcome to Pineapple Hale at KaMilo is a wonderful 4 bedroom home, part of our Hawaiian Luxury Collection.Pineapple Hale at KaMilo, with updated furnishings (2024) and decor provides a perfect setting for your Hawaii...
TOP FLOOR-STUNNING OCEAN VIEWS-WELL EQUIPPED-ALL NEW FURNISHINGS
Book with confidence, this remodeled top floor unit at The Royal Mauian with stunning ocean views. This 2 bedroom, 2 bathroom condo offers an exceptional vacation experience and is fully equipped with everything that you need to have a great vacation. It has been...
Beachfront Paradise North Shore, 4BD, King Beds, AC, Parking.
Escape to paradise in a newly remodeled beach bungalow with panoramic ocean views. Step directly onto the beach from the back lanai. During summer months, enjoy your own private beach right upfront or walk a few steps to a larger beautiful semi - private beach. The home...
Hanalei Bay Oceanfront Spacious Home
Come to the charming town of Hanalei and experience the Jones House, a spacious oceanfront home on spectacular Hanalei Bay. Steps away from the beach with breathtaking views of Hanalei Bay, the Jones House is sure to delight. Swim, surf, sunbathe, and stroll along the...
Hale Hiwa Hiwa By Parrish Kauai - AC & privacy at Wainani village
Hale Hiwa Hiwa or our "Beloved Home" at Wainani is the perfect place to spend a relaxing and pampered vacation on Kauai. Located in a cul-de-sac on Kiahuna Plantation Drive you are centrally located in Poipu and close to shopping, dining and Poipu Beach.Enjoy the...
Regency 111 Defines Comfort & Spaciousness. Lovely Furniture & Furnishings
*Completely refurbished corner unit with high ceilings and over 1300 square feet of living space with new and comfortable furniture.*Master bedroom has a King SLEEP NUMBER bed which allows you to adjust the firmness of the mattress.*Twin beds in the second bedroom allow...
Oceanfront Home w/ Pool, Gazebo Access in Papaikou
Patio w/ Water View | Gas Grill | 3 Mi to Honoli'i Beach Park Seeking a relaxing Hawaii escape surrounded by nature? Look no further than this Papaikou vacation rental! With on-site pool access, scenic ocean views, and a prime location near beaches and hiking trails,...
K L V R presents Beautiful Ground floor Villa 1A at Honua Kai Resort,
Kaanapali Luxury Vacation Rentals welcomes you to our beautiful garden level Luana Villa at the Honua Kai Resort.This new, luxurious villa is located within a private garden enclave at the spectacular, beach front, Honua Kai resort. This villa boasts 2047 sq. ft. of...
Luxury Condo Waikoloa Beach Resort, Gold Member Golf Package included.
This beautiful luxury 2 bedroom, 2 bath condo comes with amazing golf & pool benefits and is located in the Waikoloa Beach Villas at the Waikoloa Beach Resort. The space: Our beautiful newly remodeled luxury 2 bedroom, 2 bath condo comes with amazing golf & pool...
NEW - Lauhala - Hawaiian Villa with private hot tub
Proudly presenting this spacious home, new to the market and freshly renovated with everything needed for your vacation! It is a secure property, fully fenced with dual automated gates, circular driveway and ample parking. The floor plan is open, kitchen is fully...
Lovely 2nd Floor Unit On Golf Course, Easy walk to Beach, Restaurants, Shopping
Located on the beautiful Waikoloa Beach Course, 1st fairway and green with the Petroglyph Trail and Mauna Kea as the backdrop, the second floor unit has two bedrooms with king size beds and options for separate twin beds, an open lanai and generous living space for your...
West Maui Ocean front Condo, Lahaina
Thank you for your interest in our condo. Our condo is outside the fire of 2023 perimeter, but clean-up is still going on and Lahaina Town is closed. Our unit has a King bed, WIRELESS INTERNET and views. Do you need anything else to have a great vacation? Hale Ono Loa,...
Kailua Beach Hideaway TA-189-305-8560-01
Beachfront! The White Sand of Kailua Beach at Your Door!This 4 bedroom, 4 bath, en suite home is the Perfect Tropical Haven.Tucked away and private, this home embodies the true island lifestyle.Walk or jog the long stretch of beach or lounge by the pool, with...
Ocean view home on beautiful Sugar/Kihei Beach - PERMIT #STKM 2015/0003
Come and vacation in your own beachside Hawaiian beach home! It is AFFORDABLE AND COVID-19 CLEANED are the keywords for this tropical beach house. Situated on a half-acre, our "feel like home", yet cost-effective 3 BR, 2-1/2 bath beach home with granite counter tops,...