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 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...
Luxury Estate with Panoramic Honolulu views. Steam room, Sauna, Spa, Heated Pool
The ultimate contemporary estate to de-stress, unwind and recharge your well-being. Luxury hotel and spa experience without the crowd and traffic. It can accommodate multiple families and corporate retreats, providing private and shared spaces, allowing guests to come...
Maui Resort Rentals: Kaanapali Ali'i 362 - Elegantly Remodeled 6th Floor 2BR w/ Ocean AND Mountain Views!
This incredible listing was recently remodeled and boasts gorgeous views of both the tranquil blue Pacific Ocean AND the lush West Maui Mountains.The elegant remodel was completed in 2017 and only the finest materials were used. From top to bottom, no expense was spared...
Maui Wailea Escape 2 Bedroom, 2.5 Bath Condo #23A - View, Pools, Walk to Beach
Sun, fun and the Hawaiian Island lifestyle is waiting for you! Our townhouse is located in the beautiful beach front property of Ekahi Village. Explore the winding pathways through Ekahi's lush gardens spanning over 34 acres. Take a stroll down the hillside and you'll...
Kona Plaza 301, Ocean Views and Renovated
Kona Plaza 301! Your Ideal Hawaiian Getaway! Welcome to Kona Plaza 301, where modern comfort meets tropical paradise! This beautifully updated condo features brand new floors and is designed to provide you with a relaxing retreat during your stay in the heart of...
🐬Georgeous 5-STAR Wailea Retreat!🏝Tranquil Corner unit, Top tier Upgrades🌈
Wailea Grand Champions Villas -- Condo #188Aloha!You are coming to Maui for your Dream vacation---Why not stay in a Tranquil, spacious condo full of High-end amenities while enjoying the island? We welcome you to share our well-loved Maui paradise in stunning Wailea!...
Cleaning fee waived!! 5 mins to the Beach/ OCEAN+Mt View. Centrally located
For limited time only 5% monthly discount.Early check in 10:00am and late check out 3:00pm at no additional charge. Breathtaking ocean and diamond head view right from the 32nd floor, features a spacious 1100 square feet with central AC and an open concept living area...
Studio Suite at Waikiki Marina Resort at the Ilikai
Come enjoy this beautiful Waikiki resort! Now reopened!COVID Update: Enhanced cleaning measures are in effect. Some amenities are open with access limitations.• Must provide resort with negative covid tests taken within 72 hours of arrival (for all people staying...
100% OCEAN VIEWS FROM ALL ROOMS, Cancellation June Special!!, Hokulani #525
**Book any stay for 7 nights or more and receive 10% off at instant booking**We offer an owner-managed luxury condo with a personal touch. Avoid the hassles typically associated with third-party property managers. Walk from the front door to one of the world's best...
New! Poipu Kapili, Sweeping Ocean & Fully Updated w/ Newly Installed Central AC
Just renovated! Enjoy ocean waves and sweeping views of the Pacific in this stunning Hawaiian style townhome in Poipu Beach, Kauai. Creature comforts: Newly Installed central air for a good nights sleep; do not lie awake to the sound of portable ACs that are at the...
BBQ Grill on the lanai and Beach Gear Included! Waikoloa Beach Villas G1
This vacation rental is professionally managed by ResorticaHawaiiWaikoloa Beach Villas G1Please scroll down for detailed informationBedding Configuration:Master Bedroom: King BedGuest Bedroom Upstairs: One Queen BedGuest Bedroom Downstairs: One Queen BedAmenities:Beach...
Tropical & inviting home w/spa, torches, waterfalls & ocean view
Hale Wailele (Waterfall House) is a beautiful, spacious home with floor to ceiling windows in the great room looking out onto fountains in the pool with an incredible ocean view beyond the palm trees and torches. The architecture of the home makes it unique and inviting...
Gorgeous Beachfront Condo in Wailea with Private Lanai
*Please note Ekahi Village is a non-smoking community. Smoking is not permitted anywhere on property including patio/lanai, and all communal outdoor areas. Located in beautiful Wailea, the complex is just steps from Keawakapu Beach and walking distance to great...
Ocean Front Luxury Condo - Relaxing Comfort
Kuhio Shores 104 is on the ground floor of this amazing ocean front property. It is very special, perfect for Honeymoon, anniversaries, birthday celebrations, and is also a place where you can completely relax! We are also close to all of the South Shore sites and...
Available 5/6 to 23…..Relax at Maui Eldorado Beach Cabana, Snorkel at Black Rock
Welcome to West Maui! You’ll love this spotless tropical Maui Eldorado Resort condo in heart of the beautiful, world famous Kaanapali Beach. This updated studio has everything you’ll need for a wonderful vacation on Maui! Maui Eldorado is conveniently located...
Lodge at Kaloko - Kona Cloud Forest Estate with Pool & Hot Tub
🌴 The Lodge at Kaloko – Luxury Estate in KonaPrivate 5BR villa | Pool | Hot tub | Ocean views | Near Kua BayWelcome to The Lodge at Kaloko, a luxury gated estate in the lush Kona Cloud Forest — just 15 minutes from Manini‘owali Beach (Kua Bay), downtown Kona,...
Coconut Coast Oceanview
Enjoy convenience and simplicity from this peaceful and centrally-located retreat. Watch the sunrise over the Pacific from your private lanai , walk to lots of restaurants and shopping at the nearby Coconut Marketplace as well as Longs Drugs, Safeway, Starbucks and...
Hale Lo'i Cottage: Luxury + Convenience in Poipu
This bright, spacious, brand-new 1-bedroom, 1-bath cottage has everything you could possibly need for a flawless vacation—and luxurious perks galore, including an outdoor lava-rock shower. Located in a quiet, upscale neighborhood, this charming tropical hideaway is...
Hale Makau – Luxury Poipu Vacation Home
Welcome to Hale Makau by Gather, a luxurious retreat set within an exclusive 10-lot gated community in Poipu. This stunning five-bedroom, five-and-a-half-bathroom home offers the perfect surroundings for your large group to experience a peaceful, secluded Kauai getaway....
Paradise found-Ocean Front 2 Bdr/Bth/Lanais-Primary bedroom faces ocean FULL A/C
Newly refurnished 2-Bedroom 2-Bath. Can sleep 6 with queen size Aerobed (included). Full size washer and dryer in unit. **Air Conditioning installed in all rooms**.Lae Nani is by far the nicest condominium community on Papaloa Road, which runs from the north side of the...
Enjoy Stunning Views And Outdoor Living At This Elegant Villa
Welcome to Fairways 605 at the Mauna Lani resort. Fairways is a gated community, with lush grounds, a tropical style pool and hot tub. This luxurious townhouse is located in a prime location within the Fairways property and is positioned for ultimate privacy and a 180...
Comfortable and cozy condo
Welcome to our slice of Hawaii paradise! This fully updated and remodeled unit offers a taste of luxury in every corner. From the tiled entrance, kitchen, and bathrooms to the hardwood floors that grace the remaining spaces, you'll find comfort and style throughout.Sink...
New! Top Floor! Spacious Oceanfront Condo with Amazing Lanai and A/C!
Elegantly updated and spacious 2-bedroom 2-bathroom condo that's a wonderful choice for your Kona trip with friends or family!The clean interior design, the open layout, and the cozy high end furnishings are sure to make for a luxurious stay.Enjoy the large covered...
Kihei Paradise! 1bed/2baths, 5 mins to beach
*** Note: this property is currently a very successful STR. Starting from April, the management will be changed. This is the reason you don't see any review yet. It's Guest's favorite choice.***Charming 1BR home in South Kihei, across Kamaole Beach Park II. King bed,...
Luxurious 4BR/4BA Presidential Suite AC Near Beach
Welcome to BlueTideVillas! Welcome to Poipu's newest luxury resort-style villas! This is a VERY spacious (2750+ total square feet), top floor villa featuring 4 bedrooms and 3 1/2 bathrooms, with three private lanai's to sit on and enjoy your favorite tropical drink....
Maui's BEST- DIRECT Oceanfront!! Longest Sandy Beach on Maui!!
Welcome to Sugar Beach #228. I invite you to enjoy one of the world's finest beaches - Sugar Beach, with its 5 miles of golden soft sand, warm water and beautiful sunsets. This direct oceanfront condominium has been completely updated with all of the high end finishes...
Loko Kai Nani - Stunning Lagoon Views, Pool, A/C
Welcome to Loko Kai Nani, the Beautiful Lagoon! Look no further. For the Ultimate Big Island Experience. Beats any Hilo Hotel by a mile (IMHO) Fully Air Conditioned, 24 hour security, Everything is Brand New.First time offered, fully renovated with brand new...
Private Hawaiian Estate with Pickleball Court - Old Hawaii Retreat
Old Hawaii at its best! Enjoy the updated traditional home nestled within a fully enclosed and private one-acre tropical estate! Chase the keiki (kids) or grandkids on the spacious lawns, or just enjoy the many tropical trees and plants—coconut, banana, mango, ulu...
New Listing- Hale Aka'ula, house of the red sunset
Three bedroom two bath home in the lush sanctuary know as Kohanaiki, this comfortable home is your perfect Hawaiian retreat. Large living room and chef's kitchen are perfect for family gatherings with plenty of windows to enjoy the ocean and sunset views.Tropical...
Amazing views from this ground floor, corner unit steps from the beach!
Enjoy a piece of heaven from this ground floor corner unit with granite counter tops, tile flooring, washer and dryer, and a fully furnished kitchen with everything you need to cook gourmet meals. The condo sleeps 4 comfortably. The master bedroom has a king size bed...
Wailea Beach Villas | PH307
In Wailea Beach Villas PH307 you can immerse yourself in luxe tropical comforts blended with blue ocean views. This delightful Maui ocean view vacation residence will cultivate long lasting memories and leave you feeling rejuvenated upon departure. Centrally located on...
Spacious 2 Bedroom 2 Bathroom City View Condo at the Ilikai Hotel
Experience the beauty of Waikiki with Happy Vacations, a short-term vacation rental company! Our team is excited to offer you a modern condo at the renowned Ilikai. You'll love the open floor plan with lots of natural lighting, a spacious balcony, AC, and thoughtfully...
The Grand Islander, a Hilton Grand Vacations Club - 2 Bedroom Premier - Ocean View
*** Sanitation/Cleaning Update ***We understand that our guests’ expectations for hotel cleaning and disinfecting have changed. That’s why we’ve taken additional measures beyond our industry-leading cleaning standards by partnering with RB, maker of Lysol &...
Luxury Newly Remodeled 3 Bedroom Condo 20 ft from Beach
Come enjoy a stunning and spacious 3-bedroom condo villa at Kahana Village in West Maui, newly renovated and literally 20 feet from the beach, with two walls of glass and an amazing corner ocean view as well as a huge ocean front lanai.This beautiful private beach house...
𝐅𝐢𝐧𝐝𝐢𝐧𝐠𝐌𝐞𝐢𝐥𝐢 GorgeousBeachfront KoOlina Resort+Amenities.STUDIOsuite
Resort is a beachfront location. Resort has Ocean/Beach views from public area. Condo is within Beachfront Resort. VRBO Rates are Defaulted to Mountain View 2-Bedroom Villa CategoryAll units are assigned by Management onsite for all owners, guests and guests of owners...
Just Across The Street From The Ocean And Beach. 2 Bed 2 Bath Great Location
This condo has 2 bedrooms 2 Full Bath with a open floor plan in the Living room, Dinning room and Kitchen. You are looking at a lovely and functionally designed 2bd/2ba condominium situated on the third floor of a building. An elevator is provided.The SpaceAre you sick...
Mauna Lani Point | C203
Mauna Lani Point C203 offers a spacious 1,129 square foot open floor plan vacation rental designed to maximize breathtaking ocean views. From the living room, kitchen, dining area, lanai, and bedroom, you can admire the expansive blue Pacific Ocean, ancient lava rock...
Serenity in South Kihei – Maui Kamaole I215, Your Ideal Island Escape!
Maui Kamaole #I-215Welcome to Maui Kamaole #I-215, a fully remodeled 2-bedroom, 2-bathroom condo nestled in the quiet, tropical hillside of South Kihei. This stylish and spacious upper-level retreat is perfect for couples, families, or friends seeking comfort, privacy,...
Maui Resort Rentals: Honua Kai Konea 404 – Upgraded 2BR w/ Partial Ocean & Mountain Views!
Konea 404 is an upgraded two-bedroom suite that offers guests the best of both worlds. Enjoy beautiful partial ocean views, as well as stunning views of the West Maui Mountains, right from the comfort of your spacious lanai (balcony).As the very first two-bedroom back...
Plantation House by Destination Kauai - Poipu Beach Estates, Central A/C, 3BD
E Komo Mai, Welcome to “Plantation House In Poipu Beach Estates”Luxury Hawaiian living at its best! Enjoy cooking in a fully equipped gourmet kitchen with an open dining and living floor plan. This new and modern vacation home is uniquely decorated with style,...
Luxury Gated private acre , Beach front Rental,with pool,spa,sauna ,and more
TVNC #4224This one of a kind tropical gated oceanfront Luxury Estate offers the ultimate in beachfront island living and privacy on over an acre . With breathtaking ocean views and lush scent filled landscaping. The attention to detail is uncompromising inside and out....
Recent RENO! Fits 6, FREE parking
You & your family or friends will be close to everything at this centrally-located oasis in Waikiki. A couple minutes to the beach, surfing, the lagoon, boating & fishing, hiking, restaurants of every kind, shopping galore, everything Hawaii has to offer for a tropical...
Amazing Ocean Front at Sugar Beach Resort #519, High End Remodel, 1Bed/1Bath
Sugar Beach Resort is located north of downtown Kihei on beautiful Sugar Beach. Sugar Beach stretches for miles on Maui's Maalaea Bay. Stay in our Hawaiian condo and it will be a vacation you will never forget. Sugar Beach Resort is just a 15 minute drive from Maui's...
Renovated 1 Bedroom W/ Stunning Views, Parking, & Central Air
If you've been imagining the perfect place to enjoy your upcoming Waikiki getaway, look no further! Expansive Ocean and Park views, private lanai, central air conditioning, covered parking and rooftop pool and saunas check all the boxes and make this newly renovated,...
Kauai Exclusive - Pane Makai Turtle Suite - Steps to the Beach!
With ample room and durable bamboo decor, this plantation-style beach suite is perfect for large groups, wedding parties and family reunions. Comfortably sleeping 7, look no further for the perfect gathering place for friends and loved ones! This 3000 square foot suite...
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...
PACSA304 Newly Updated 2BD Condo w AC Near Kamaole Beach
Pacific Shores A304 2Bedroom Condo Across the Street From Kamaole Beach. Walking Distance to Restaurants, Shops, Beach Activities FREE daily activities included with your stay value up to $554! Complimentary admission, every day of your stay*: Whale Watching (seasonal),...
Princeville Palms Manor - Hanalei Bay
Locally-crafted Décor, Spacious Chambers, with Natural Wood Trim. Beautiful Two-Story Air-Conditioned Retreat …serenaded in the song of jungle birds!Meticulously thought-out kitchen, accessories, games and endless amenities. For our eco-conscious guests, we've...
Sunset View - Ocean Front - East Honolulu - Newly Upgraded
Enjoy the perpetually calm span of crystalline ocean and the gentle trade winds as you relax on the oceanfront lanai or sun deck of this beautiful home tucked onto Oahu's south shore. Launch a kayak or stand up paddle board from the private dock or relax on the large...
Maui Westside Presents - Eldorado H208
Welcome to Maui Eldorado H208!This beautiful Second floor 1440 sq ft 2 bedroom/2bath condo has been completely renovated and is ready for your perfect Maui vacation. Ocean views from the spacious lanai are perfect for watching the evening sunset as you sip your favorite...