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.
Newly Renovated, Modern Beach 70’s Surfer Vibes
Welcome to the beautiful Kahakai Cliffside - Located on the stunning North Shore of Kauai. Completely renovated in 2023 with dual-zone air conditioning, Kahakai Cliffside sets a new bar for modern-beach 70’s surfer vibes with high-end flourishes throughout. This...
Prime Location, Budget Friendly Kahalu'u Bay Getaway
You'll love the location and the views from the lanai. You can enjoy sunrises and sunsets, depending on the time of year, as well as water views year round. Situated steps (160 m to be exact) from Kahalu'u Bay, which has one of the best snorkelling beaches in Hawaii on...
Lovely Private Kailua Cottage
Welcome to our newly renovated 1-bedroom spacious and private cottage that is super centrally located in the heart of Kailua. Our cottage is situated on a beautifully landscaped property which will lead you to a lusciously landscaped garden with outdoor dining & BBQ....
Beautiful Mauna Lani Home with access to the Private Beach Club.
This spacious Hale Honu townhouse has an open floor plan providing 2174 sf. of luxurious living (plus over 400 square feet of covered outdoor lanai). It features 3 ensuite bedrooms and a guest half bath. Villages 619 has mahogany trims and doors, upgraded countertops in...
Ocean Tower Waikoloa Village by Hilton - 2 Bedroom Penthouse (sleeps 8)
Ocean Tower Waikoloa Village by Hilton Grand Vacations Club - 2 Bedroom Penthouse (Sleeps 8)**all photos are stock images and do not guarantee the view shown****PLEASE READ ENTIRE DESCRIPTION BEFORE REQUESTING RESERVATION**Book our Fabulous Condo & let The Vacation...
Stunning Ocean View Penthouse Unit! Quam Properties Hawaii
Kaanapali Shores 905 one-bedroom penthouse featuring amenities such as a magnificent ocean view, comfortable seating area, and a private lanai. The condo can accommodate up to 4 guests with a king-size bed in the bedroom a queen sleeper sofa and a twin sleeper sofa in...
Kona Oceanfront-Gorgeous, Quiet, Sleeps 6
Summary:Discover paradise at our stunning oceanfront retreat! Nestled amidst swaying palms and lush tropical greenery, this three-bedroom, three-bathroom sanctuary offers a serene getaway for up to six guests. Wake up to the soothing sound of waves crashing and soak in...
Maui's Ultimate Luxury Estate – Ka'anapali Beachfront Paradise
Boasting an epic location on one of only six beachfront residential parcels in all of Kaanapali, this breathtaking 9BR/9.5BA estate represents the pinnacle of Maui vacationing. Guests will enjoy the space and solitude of this luxurious private home, nestled steps from...
Luxurious & Spacious Ocean Vistas
Summary:Beautifully remodeled in early 2023. This elegant 2-bedroom, 2-bath condo features upscale touches with magnificent ocean views. Located steps from Wailea, all of Maui is within reach. We offer a fully stocked kitchen for those who want to cook. Enjoy the...
Top floor, direct oceanfront views, & remodeled Kaleialoha gem.
Welcome to Kaleialoha 413. This top floor, direct oceanfront condo features panoramic ocean & island views. This condo has a remodeled kitchen & bathroom, AC in living area, 2 Flat screen TVs, new king bed with luxury bedding and more! Close to shops, dining, farmer's...
Kihei Akahi C310-Owner Managed-Complete Renovation-Modern Luxury-A/C throughout
Kihei Akahi C310 is a fantastic 1 bedroom, 1 bath condo. It has an ocean and Haleakala view from the lanai (balcony). It was completely renovated in 2022, with new furniture, new appliances - new everything! It has been modernized with Mitsubishi split A/C units in both...
Kope Cottage -1 BR -1B-Endless Views
The Cottage sleeps 3 people in 600 sq ft. It is a true one bedroom and not a studio. It has 1 full size bed and 1 queen size bed. It also has a queen-size pull-out sleeper bed as outlined above. There is also a modern washer/dryer in the Kitchen area.In the cottage, it...
Completely remodeled 2 bedroom King bed AC Kauhale Makai on the top flood
• Oceanfront• Central A/C • King bed and queen bed• Remolded March 2023• Beach access from condo complexWelcome to our home at Kauhale Makai 612. Our home was fully and immaculately remodeled in March of 2023. Our beautiful and pristine two-bedroom condo sits on the top...
2 Bed Maui Retreat with 5 miles of beach!
Kanai A Nalu, what a gorgeous beach front condo! It's a great remodel with tile flooring throughout, island-style furniture, and a stunning kitchen with a full-size front load W/D! All the comforts and conveniences of home, but it's in paradise! With 2 bedrooms, one...
Awesome Oceanfront Condo, Great Views, Steps to the Beach, KR#207
Enjoy the gorgeous ocean views while sitting on the lanai and soaking in the beauty all around. This condo sits right on Sugar Beach, with 6 miles of white sand beach right in front of our condo. Great for beach walks, playing in the ocean, or enjoy the shade trees in...
Holua Kai#8 w/ Private Pool, Ocean & Golf Views, Community Pool & Spa
Holua Kai #8 invites you to unwind in style within the private gated community of Kona Country Club Ocean Course. This elegant single-level home blends open, light-filled interiors with a private heated pool and lanai framed by lush golf course greens and distant...
Beautiful Plantation at Princeville
Lovingly maintained home! Bright and airy, ground level condo with attached one-car garage in a desirable community in Princeville on the North Shore of Kauai. This unit is the essence of aloha and comfort. Brand new linens, new boogey boards & cooler chest. The...
Kilauea Ocean Bluff Estate – Luxury 2-Bedroom Home with Secluded Beach Access
Escape to this enchanting 12-acre estate with panoramic ocean, mountain, and river views. The main residence, guest bungalows, and bathhouse form a connected compound amid lush gardens. The great room with Teak sliding doors opens to the garden and ocean view. Custom...
Anini Vista Drive Estate - Kauai North Shore Gem
A grand estate centered on a magnificent lagoon-style saltwater pool with two waterfalls, a grotto, hot tub and bridge, Anini Vista Drive Estate is a paradise in its own right. Inviting ocean views and expansive gardens surround the main house and guesthouse, which are...
Ikena Lani - Beautiful 5 BR House with Pool & Jacuzzi overlooking Kalihiwai Bay
Welcome to Ikena Lani, a luxurious modern custom home with breathtaking ocean views. Designed by award-winning firms, it offers a serene island retreat with hand-picked materials from Asia. The main house has 5 bedrooms, a spacious living room, kitchen, and media room....
Hanalei Plantation Road Home - Dream Retreat with Pool & Ocean Views
Escape to this beautiful Hanalei Plantation Road home, nestled in a prized neighborhood. Enjoy sweeping mountain and ocean views over Hanalei Bay. With 4 bedrooms, a gym, pool, and ample indoor/outdoor space, it's a dream retreat. Upstairs, find a bright living/dining...
Hanalei Bay Hale: Beachfront Vacation Rental with AC
This beachfront home on Hanalei Bay offers 3 bedrooms, 2 baths, and air conditioning throughout. Just steps from the sand and minutes from Hanalei town, it’s the perfect beachfront Hanalei location with views of Bali Hai. The Master Suite features a king bed and en...
Spring Special! Fantastic Beachfront Wailea Ekahi 2/2
Welcome to my sunny Wailea Ekahi Paradise! This unit is a remodeled, expanded and wonderfully furnished 2 bedroom 2 bathroom ground-floor condo (Unit 43A) is the perfect spot for a family or group vacation! Keawakapu Beach is just a short walk away through beautifully...
Kauai Exclusive - Kauai Prince Kuhio 104 - Newly renovated & steps to the water
Kaua'i Prince Kuhio 104 is a gorgeous, ground-level, one bedroom condo with ocean views. The owners spared no details in the remodel of this home! A stunning kitchen, new flooring and an inviting living room! From your private porch, enjoy the serene sounds of rolling...
Stunning Fairway Views, Home "E"-Clean-New-Gated, near Jbphh, Cage # Available.
Welcome to Hillside Perfection overlooking the fairways at Golf Ridge Homes!Discover your ideal fully furnished, 5 bedroom, air conditioned executive home located in central Honolulu. Perfect for leisure visitors, savvy business travelers or visiting construction crews...
Exotic garden cottage at amazing volcanic fissure
Escape to our cozy and romantic gem nestled in the heart of paradise. Our garden cottage is a stunning specimen of natural beauty located between magnificent Volcano National Park and the historic town of Hilo. Provides easy access to both attractions.The stunning...
Ocean Front Beach House located only steps from the water!
E Komo Mai!At Nalu Hale (surf house) we welcome you to emerse yourself in surf culture. Wake up to the waves crashing on the shore of Kahalu'u Bay and never miss a sunset. Whether you like to surf, sup or snorkel, Nalu Hale puts you just steps from your next ocean...
Luxury Waikiki condo - 28th floor! Stunning views, convenient location, parking
Allure is one of the most luxurious private condominiums in Waikiki. The grounds, pool, and other amenities rival the resort hotels, but you get even more space, privacy and freedom. This property is ideal for couples or families seeking to feel at home in Waikiki for...
Hilo's Finest 2 bd Condo - Pool, A/C, Views!
Enjoy a stylish experience at this centrally-located condo. Far exceeds any Hilo Hotel. 2brm with living room with super comfortable couch and loveseat. FULLY air conditioned. The view is spectacular. 24/7 security building. Free assigned parking. Wifi with 3 smart...
Alaula by AvantStay | Gated Security Home w Valley, Ocean Views!
Welcome to Alaula, located in the gated community of Makaha Valley! Boasting stunning views of the Waianae mountain range and the Pacific Ocean, this city escape offers you picturesque sunsets and peaceful mornings amongst Hawaii's natural beauty.The backyard is large...
Panoramic Ocean View Condo on Golf Course close to Beaches
Our townhouse in the Wailea Ekolu Place located on the Wailea Blue Golf Course. It has a spectacular view and large lanais to enjoy a panoramic views and Maui sunsets. It has 2 bedrooms, 2 full + 1 half bath townhouse. Our master bedroom has a king sized bed and ensuite...
Fully Remodeled Hanalei Bay Villa #34 w/ Amazing Views!
Hanalei Bay Villas are located on a bluff with incredible mountain and ocean views and just a short walk away from the new 1 Hanalei Bay Hotel. Villa #34 has been completely remodeled and designed in cool neutral tones with a clean modern vibe. All new, high end...
Stunning tropical retreat near the beach with pool, views & spacious lanai
Ho'oka'ana HaleOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Live the luxe life at the top of Alii Heights! Surrounded by colorful blooms and palm trees, find yourself waking up...
Maui Resort Rentals: Honua Kai Konea 609/13 - 4 Total Bedrooms, 6th Floor Deluxe Ocean Views!
This pairing combines two of the best 2BR suites on offer at Honua Kai. Each suite provides its own spacious, oversized lanai overlooking the pristine pools within the Konea Towers' lush interior courtyard and boasting stunning views of the turquoise-hued...
Cool retreat at the entrance to Lanikai-Very Close to Beach-3 Primary Bedrooms
Live your best life! An opportunity for beach living in this renovated and updated luxury rental with views of Kailua Beach and Kailua Beach Park - it's brilliant turquoise blue ocean, sandy beach, large grassy areas and tall ironwood trees. Fine craftsmanship abounds...
This Is Your Home away from Home! Well equipped condo and breathtaking Views!
Your vacation of a lifetime starts with sprawling ocean, beach and mountain views. The cool northwest exposure #407 allows for views of sublime sunsets, beach activity on Kamaole I and the whirling windmills of the West Maui mountains. The lanai patio is the perfect...
Magic Sands Ocean Front Condo. Kailua-Kona
This studio is oceanfront with stunning views. The popular Magic Sands beach is right next door. Bar and restaurant downstairs and bike rentals across the street. Close to Kailua-Kona town and other popular beaches including the famous snorkel beach Kahalu'u.This unit...
A Plush Two-level Condo with Ocean and Golf Course Views From its Lanais
DescriptionKanaloa at Kona is in Keauhou on the water between Heeia Bay and the Keauhou Kona Golf Course. This resort boasts three swimming pools, including one that is absolutely oceanfront. There are also three hot tubs, two tennis courts, and a game room. Enjoy...
Kailua Condo / Townhouse on Oahu 7 day per 30 day period
”Aloha and Welcome Home" message me on availability as it can only be rented once in a 30 day period. Ordinance 19-18 does not require a renter to physically occupy a rental property for any minimum length of time. Remodeled 2x bedroom 2x bathroom condo / townhouse. It...
May Last Minute Special! Amazing Ka'anapali location-Ocean Views-Cold AC
‘Anuenue Hideaway’ at Maui Eldorado Kaanapali – Unit K2041 Bedroom | 2 Bathrooms | Ocean Views | Steps from Ka’anapali Beach | Great Pools and Hot TubWelcome to Anuenue Hideaway — your private escape in the heart of Ka’anapali Beach Resort. This beautifully appointed...
Kona Palms#201:Oceanfront with great views, AC, elevator and wraparound lanai
Gorgeous views from this spacious and updated 1041 square foot condo with 2 bedrooms, 2 bathrooms and Sleeps 5 to 6! Picture yourself relaxing in this absolutely beautiful condo, enjoying the ocean views, while watching surfers and the magically blue waters of the...
Lush Private Tropical Estate, Epic Views w/ Salt Water Pool & Spa
Nestled on an acre of private and quiet lush tropical grounds with heated pool and hot tub, Heart of Hualalai is your dream home, away from home, in Kona coffee country.Heart of Hualalai is a peaceful space where natural beauty and serenity meet mindful architectural...
Islander on the Beach ONE-BEDROOM unit #308, Top floor, incredible Ocean Views
NO RESORT FEE, FREE WIFI in the condo and FREE DEDICATED PARKING.Unique Top floor One-Bedroom unit #308 is one of the only two truly one-bedroom units available in the Islander on the Beach resort. It features a separate bedroom with a California King bed; living room...
North Shore Getaway w/ Ocean Views steps to Beaches and Surf
This beautiful getaway features a secure gated driveway accessed by remote in which you will enter. Drive up left side of Garage to recessed home where you will access a set of stairs only accessed by you and your guests. This entry leads to an open floor plan Private...
Spacious 3BR/2.5BA Townhome in Quiet Ko Olina - Pool, Beaches & Golf Nearby
Enjoy our comfy 3-bedroom, 2.5-bath townhouse in the quiet Hillside Villas community at Ko Olina. Our home is minutes away from world-class beaches, golf, and restaurants. Our place offers comfort and convenience for your tropical getaway. Nestled in a quiet,...
Fantastic Hana Bay Oceanfront Location! 5-Minute Walk to Hana town & beaches!
AUTHENTIC HAWAIIAN BEACH HOUSE ON HANA BAYManini Cottage captures the relaxed comfort and charm of a true Hawaiian beach house in a rare and secluded oceanfront setting. Perched at the edge of Hana Bay, this one-bedroom, one-bath cottage features open-concept living, a...
SEArider TWO at Turtle Bay (1 bedroom / 1 bath) - Kuilima Estates East
Our number one priority at SEArider is to provide our guests with a luxury Hawaiian experience. This unit has been completely renovated with our main focus being quality and comfort. Nestled in the condominiums that surround Turtle Bay, TWO has a luxurious but minimal...
Maui Resort Rentals: Honua Kai Hokulani 415 - Upgraded 2BR Ocean View Suite w/ Deluxe Corner Floor Plan!
Widely regarded as the premier two-bedroom floor plan at Honua Kai, this oversized two-bedroom boasts a 1325 sq. ft. interior with direct ocean views from the kitchen, dining room, and living area, as well as the 315 sq. ft. wraparound lanai (balcony). The Hokulani...
Oceanfront Cottage 5A
You can't beat the views and privacy from 5A!Perfectly situated on the lot, with picture-perfect views of sunsets, Kaiaka rock, and Oahu. Your cottage has a new kitchen (January 2023) and offers amazing natural light and sense of space from 3 walls of windows/doors and...
Private Corner Unit with Spectacular Ocean Front Views
Aloha! Come and enjoy Hale Ho’ola. Our “House of Healing”, situated atop a bluff overlooking the beautiful blue Pacific is a corner unit so private, that it feels like you are the only ones there! Surrounded by the beautiful sights and sounds of the ocean along with the...