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.
Waipouli Beach Resort Exquisite Crown Jewel!
Waipouli Beach Resort Exquisite Crown Jewel! Newest Listing! Central ACThe Ultimate Vacation Experience staying in this Exquisite Penthouse Premier Ocean View Extra Large* Luxury Condo, the Best of the Best - centrally located for THE premier view of the ocean at #1...
Kuhio Shores 415 Top Floor Oceanfront Condo with new central a/c
Mini split Air Conditioning system installed to make your Kuhio Shores 415 cooling experience perfect. Open windows, trade winds, fans to hear the soothing sounds of the ocean. And now if none of the above works you have use of a quiet, efficient air conditioning system...
Makena Surf C207 Beachfront Resort - 2 Bedroom Oceanfront Condo
Welcome to Makena Surf C207, a vacation rental nestled in paradise. This spacious suite offers a serene escape, featuring two large lanais surrounded by the sweet scent of Plumeria. Unwind after a day at the beach by relaxing with friends and family, engage in a...
Ocean View Family Condo Across From Lyman’s Cove~Air Conditioning~Calif King Bed
Royal Kahili A402Beautiful OCEAN VIEW and pool view from our fourth story condo! Top floor, no overhead neighbors! Elevator works as of 8/10/2023!You will need to ascend/descend 4-5 steps to access our condo. Enjoy our refreshing pool and spa, surrounded by gorgeous...
Wailea Beach Villas PH306 - 2 Bedroom Ocean View Penthouse
Settle into your very own slice of Maui paradise with a stay in Wailea Beach Villas PH306. This exquisite two bedroom, two bathroom penthouse with exceptional ocean and island views are sure to inspire the luxury, comfort and serenity you deserve. Thoughtfully designed...
Summer sale! Waikoloa Colony Villas! Quiet redone end unit. Great views, 90 golf
Experience paradise at its finest in our beautiful, upscale villa overlooking Waikoloa Beach Golf fairway with breathtaking views of elegant palms and distant volcanoes. Hale Pele #601, was remodeled to perfection with gorgeous tile floors and a designer master bath....
Ocean Front Beachside Beauty. Two Free Rounds of Golf*
*SPECIAL - 2 Free Rounds of Golf at the King Kamehameha Golf Club, Maui's Premiere Private Club. On Stays of 5 nights or more. Looking for a great Honeymoon, Anniversary or Vacation of a Lifetime. Our 1 bedroom condo is just the right place for you! King Bed with luxury...
Steps to Kahana Beach from this fully remodeled condo - Listing Special 40% OFF
Welcome to Maui Makai Condo!This lovely 1 bedroom, 1 bathroom condo is situated in the hotel zone and just a stone's throw away from Kahana Beach in West Maui (conveniently nestled between Ka'anapali and Kapalua).Following extensive renovations, we've tailored this...
Spectacular, Oceanfront 3 bedroom + den, AC, pool, sleeps 7.
Puamana 160-2 offers a spectacular opportunity to enjoy oceanfront living at its best. Relax on your spacious lanai just 40 feet from the water’s edge, grilling, dining, and watching the ever-changing ocean vistas, surfers dancing on the waves, whales in season,...
Laule'a 11: Mauna Lani Luxury Retreat with Private Pool & Spa
Welcome to Laule'a at the Mauna Lani Resort #11, your luxury island retreat. This vacation home affords you an immersive Hawaiian getaway experience. As you step inside, your breath will be stolen by the stunning golf course vistas and the majestic Mauna Kea mountain...
Read Our Reviews and See Why Our Guests Love to Stay with Us.
It is not easy to find a great place to stay while vacationing in Maui, there are so many possibilities to choose from. The good news is that you have just found one of the best. What we offer you is a beautiful condo in a great condo complex, with the perfect location...
Magnificent....Marvelous....Open Dates...Wonderful Waves!
Magnificent.....Marvelous...that's what you will say upon entering this 2 bedroom/2 bath oceanfront air conditioned home away from home. You will be greeted by comfort and impeccable decor and comfortable furnishings....a walk-in shower in the master bathroom! If you...
4th floor Oceanfront Gem
We are welcoming guests back to Lahaina Roads, our property and apartment have been updated over the past two years and we are excited to greet our guests with heartfelt Aloha!We have worked very hard to provide you with a ‘home away from home’ atmosphere! After an...
Maui Resort Rentals - Exclusive Hyatt Residence Club 1BR Oceanfront Upper Floor Viilla
Exquisite 1 Bedroom Villa With Jaw-Dropping Oceanfront Views at Kaanapali's Newest, Most Exclusive Resort! Proudly perched upon Ka'anapali, one of the world's most beautiful beaches, is the Hyatt Residence Club Ka'anapali. Within the lush borders of this sprawling...
🏖️Stunning Ocean Views | Discount of Golf | Complete Remodel | vrKCV
vrKCV - Halii Kai 11D, Professionally Managed by Kona Coast VacationsWelcome to Your Island Retreat at Hali'i Kai 11DDiscover the perfect combination of modern elegance and Hawaiian charm at Hali'i Kai 11D. Nestled in an unbeatable location overlooking the Kings Golf...
Haleiwa Oceanfront Cottage - Charming 1BR Retreat
Discover the delightful onebedroom getaway nestled right within Haleiwa. Nestled just a 22-minute drive from the renowned Banzai Pipeline and 24 minutes from the stunning Turtle Bay Beach, this cozy retreat offers the perfect base for your Hawaiian adventure. ocean...
10th floor Oceanview studio @ Royal Kahana Resort
Welcome to Royal Kahana 1004. This 10th floor studio offers ocean & surrounding island views. Tastefully decorated with classic tropical decor. This studio features a king size bed & a twin sleeper sofa, accommodating 3 guests. The updated kitchen & bathroom features...
Hilton Lagoon Tower, 2 Bedroom Premier
2 Bedroom Premier (2BX)Size 1,025 sqft Accommodates 6 guestsRoom DescriptionThis spacious two-bedroom, two-bathroom ocean front view suite with lanai located on the 3rd - 23rd floors, features a primary bedroom with king-size bed, 55-inch flat panel HDTV, and bathroom...
OCEANFRONT CONDO - INCREDIBLE VIEWS! Kihei Sands Beachfront Condos-B9
Pack your favorite flip-flops & get ready for a winter filled with sun, sand, & whale tails. Maui is calling, and it's never been more inviting with our NEW LOWERED Winter rates starting November to March 2026!Are you craving PANORAMIC views from your condo & private...
Kilauea Lakeside Estate - Secluded Luxury Retreat on Private 4-Acre Peninsula
This totally private resort has been described as the best private Kauai retreat in the Hawaiian islands. Located in a wildlife refuge on its own private lake on the island of Kauai, Kilauea Lakeside Estate is a beautifully secluded Hawaiian retreat, simply perfect for...
Alaula by AvantStay | Gated Security Home w Valley, Ocean Views!
★ Recognized as one of our best. This home was a finalist in the 2025 AvantStay Awards, our annual celebration of top-tier stays.Welcome to Alaula, located in the gated community of Makaha Valley! Boasting stunning views of the Waianae mountain range and the Pacific...
North Shore Oasis, Hot Tub, across street from beach. Inquire for dates/prices.
Aloha and welcome to your retreat along the North Shore's 7 mile miracle. Right across the street from white sand beach and famous surf spots. Please contact us prior to booking at (808) 754-6453 or request booking or quote through VRBO. We can negociate the rate based...
PK L303 Kaanapali BeachFront 2BD w Ocean Views Pool AC
Papakea L303 Paradise Awaits at This Oceanfront Condo Reflecting The Island Lifestyle FREE daily activities included with your stay value up to $570! Complimentary admission, every day of your stay*: Whale Watch (seasonal), Dinner Sunset Sail, Snorkel Sail, Alpaca Farm...
Fairways at Ko Olina 4A: Luxury Condo w/ Balcony Views & Resort Amenities
Fairways at Ko Olina 4A is your serene island retreat, nestled in a quiet corner of the Resort at Ko Olina. This upgraded two-bedroom, two-bath condo offers garden views, modern comforts, and resort-style amenities, all just steps from sandy lagoons and world-class...
Aloha Condos, Na Hale O Keauhou, Townhome M-4, Ocean View, AC
Enjoy Panoramic Ocean Views from your private lanais. Sunset views 365 days a year. Your only decision, whether to use the upstairs lanai with chaise lounge and cosy sitting area perfect for morning coffee or wine and cheese at sunset, or the downstairs lanai with...
Welcome to Ho'onani Pua Hale
Ho'onani Pua Hale offers accommodations in Waipahu, 9.4 miles from USS Bowfin Submarine Museum & Park and 10 miles from USS Arizona Memorial. This vacation home provides accommodations with a patio and free Wifi. Outdoor dining is also possible at the vacation home.This...
Kailua-Kona Condo Rental ~ 1/2 Mi to Golf Course!
Escape to paradise at this peaceful 2-bedroom, 3-bathroom Kailua-Kona vacation rental! Boasting a full kitchen, a cozy living area, and a loft with a view, this property has all the essentials for a family retreat or a getaway with friends. Relax on the balcony while...
Oceanfront Condo: Stunning Views, Pool, High-Speed Wi-Fi, Near Beach,Shops,cafes
Maui Oceanfront Retreat | Private Lanai, Steps to Beach & Stunning Ocean ViewsWelcome to your dream Maui escape! Wake up to breathtaking ocean views and enjoy your morning coffee on your private lanai, just steps from the soft sands and turquoise waters of one of...
Fairway Villa 2417
Fairway Villa #2417 – 2345 Ala Wai Blvd(30-Night Minimum. ALL MONTHLY RESERVATIONS ARE SUBJECT TO APPROVAL.)HIGH FLOOR! TOP TO BOTTOM RENOVATION! Your Home Away from Home! Enjoy this recently renovated two-bedroom, two-bath condo (723 sqft plus 151-sqft lanai) with...
Kona Ocean View Home - Downtown, Fruit Trees, Sunset views
Beautiful 2bedroom / 2bath home overlooking Kailua Bay in the heart of downtown Kona, HI. Conveniently located on the gentle slopes of Hualalai. Escape the heat with cool breezes in a tropical landscape setting. Nearby shopping, dining, and entertainment. Fully stocked...
3-bedroom house with AC, parking
Oceanfront property. 2 queen beds, 1 bunk bed, a cozy living room, one bathroom.Guests can enjoy a cup of coffee in the morning with Honolulu and Diamond Head views! Good location. Close to restaurants, attractions, and shops.Located just steps from the ocean and the...
The Whaler 823! ~ Luxurious 2bed/2bath 8th floor ocean view corner condo ~
Enjoy Ka'anapali Beach in this beautifully remodeled 2 bedroom/2 bath highly upgraded corner unit! It’s high level on the courtyard side of tower one has a wraparound lanai which allows for sweeping views of the ocean and the mountains! You won’t find upgrades like...
Maluhia Makai - Luxe Kukui'ula island retreat in Poʻipu; AC, private heated pool
This luxury home is 2200 ft.² of air-conditioned space that opens up to 1000 ft.² of an outdoor living lanai. The design of this home seamlessly marries the indoors & outdoors together to make a grand tropical outdoor experience. Pass through its custom entry wood...
Spring Sale! Oceanfront/Ocean view condo in S. Maui,Free A/C,Wifi,Parking,Pool!
Make your trip to Maui more memorable with a stay at our 5 star condo at Luana Kai. Luana Kai is a beautiful resort with immaculate grounds in a park like setting, ocean front in sunny Kihei with no busy roads to cross to get to the ocean. Just beauty and...
Modern Top Floor Mountain and Partial Ocean View Condo
Hawaii Tax ID: TA-192-602-7264-01TMK: 390180030095Bedding Configuration: Downstairs bedroom: 1 Queen BedUpstairs loft: 2 TwinsFull size sofa sleeperOur non-smoking condo can accommodate up to six people. The downstairs bedroom offers a queen size bed. The living room...
LUXURIOUS OCEANFRONT CORNER UNIT REMODELED WITH ISLANDS & BLACK ROCK VIEWS
**Please, before you book, be aware of reservations prior to your arrival and after your departure. During certain times of the year we cannot accept reservations that leave gaps (2 to 4 days) between bookings. Please contact us, if you have any questions as to when...
Uninterrupted Sunset, Ocean and Golf Course Views from our Lanai and Interior
Please be aware we only rent to a maximum of two guests at a time. The Mauna Kea Beach Resort has remodeled the main tower and the golf course. Phase 2 is the fitness center/spa/hotel wing on the grass through early third quarter 2025, The Hapuna Westin Resort golf...
SEABREEZE RETREAT-RECENTLY REMODELED-5 STAR REVIEWS
This beautifully decorated deluxe three bedroom condo is situated in the heart of Waikoloa Beach Resort. With no units above or below, the condo offers the most in privacy. It is newly professionally decorated in Ocean colors with granite and stainless steel appliances....
Upscale Kona home in peaceful setting, ready for family gatherings.
This beautiful new home is perfect for larger families. The home boasts a huge kitchen with new stainless steel appliances and granite countertops. Equipped with everything you need. There are 3 bedrooms with additional sleeping areas that collectively can sleep up to...
Big Island Private Home Rental
Guests walk in and we see wow on their faces...gourmet kitchen, ocean views, huge bedrooms. "perfect for a family reunion""cool at night was just right""close to the best beach in Hawaii""your own private estate""amazing sunset views"We are not a corporation. We are a...
Sugar Beach Resort 333: Ocean Front retreat with relaxing coastal décor.
Ocean Front retreat with a cool ocean breeze and coastal decor. You will feel relaxed from the moment you enter this one-bedroom ocean-front condo. The bedroom has a king bed, allowing this condo to accommodate up to two guests. The kitchen is fully equipped with...
New Listing! Exquisite Golf Course Sanctuary
Exquisite Golf Course Villa: A Private Island Sanctuary with access to Poipu Beach Athletic Club!Welcome to Wainani Villas, where refined elegance meets the serene beauty and beach living of Poipu Beach. Nestled alongside the prestigious Kiahuna Golf Course, this...
Waikoloa Golf Discounts. E2 Waikoloa Fairway Villas
Fairway Villas at Waikoloa E2Please scroll down for detailed informationPLEASE NOTE: Waikoloa Fairway Villas E2 is listed for sale. Guests may be asked to accommodate showings/inspections with 48 hours notice. Please reach out with any questions. 6/16/25This vacation...
𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢 Beachfront Maui Ocean Club Resort+Amenities. 2BR Villa
Welcome to 𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢🌴🌺 Ideally located in the heart of Kaanapali Beach along the famous Kaanapali Beachwalk. It is right next to Kaanapali Point and mere minutes from the shops and restaurants of Whaler’s...
Huge Home with Pool, Jacuzzi & Water Slide! Sleeps 18!
Affectionately named “The Pool House” by our 4 little ones, this house is above and beyond its typical name sake. This sprawling 3,000 sq.ft. home boasts 5 bedrooms and 5.5 bathrooms, with room to sleep at least 18 comfortably. A sleek modern kitchen, outdoor grill,...
Luxurious Oceanview Villa at Hualalai w/Resort Pool & AC - Ka'ulu 131C
Escape to 3BD Ka‘Ulu Villa (131C), an elegant two-story retreat set along the 4th fairway of the Jack Nicklaus–signature Championship Course at the world-renowned Hualalai Resort in Kailua Kona, Hawai‘i. With 2,414 square feet of refined interior living space and...
Stunning Ocean Views From Highly Upgraded 2 Bedroom Condo: Papakea K303
Looking for a dreamy Maui vacation with stunning ocean views? Look no further than Papakea K303 - a highly upgraded 2 bedroom condo that has everything you need and more! Located in the K building, only one building back from the ocean, this third-floor unit offers...
Mauna Loa Village Villa 2BR/2BA
Escape to a serene Big Island oasis at Club Wyndham Mauna Loa Village. Located right next door to the Kona Country Club, which features a championship golf course. This tantalizing Kailua-Kona resort is a quiet oasis tucked away from the town traffic and crowds, yet...
Pinnacle of *LUXURY*Spacious with Oversize Lanai
Come enjoy yourself at our Kamaole Sands true gem! Our gorgeous, completely remodeled condo is located on the first floor and is quiet, private and tranquil. You will love the fresh, open and airy floor-plan of this unit, tiled throughout and embellished with tasteful...
BEAUTIFUL 3/3 TOWNHOUSE WITH AC & MOUNTAIN VIEWS
At a generous 1,825 square feet of interior space, your 3 bedroom/3 bath home-away-from-home offers the popular split-level floor plan where each bedroom is on its own separate level. Upon entering Hale O’ Na Wailele you’ll find the first bedroom comes with a...