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.
PK L303 Kaanapali BeachFront 2BD w Ocean Views Pool AC
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 Tour, Pineapple Farm Tour, and All Day Electric Bike Rental. (W1)*One ticket per...
Fairways at Ko Olina 4A: Luxury Condo w/ Balcony Views & Resort Amenities
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 Fairways at Ko Olina 4A by Gather,...
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...
Iconic Diamond Head and Ocean View in Waikiki!
Aloha from Midway Vacations! Our team of local hospitality experts is dedicated to turning your Hawaiian getaway into a reality. When you stay at one of our properties, you can count on a professionally cleaned and meticulously maintained experience. We're even...
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...
8th Floor One Bedroom Condo
Enjoy staying at the Waikiki Park Heights in this spacious 537 square foot corner unit. Waikiki Park Heights is centrally located in Waikiki, just 2 small blocks from Waikiki Beach, and walking distance to all the shops and restaurants you can think of. For days of...
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...
Princeville Condo w/ Private Sauna ~ 2 Mi to Beach
Experience the perfect blend of oceanfront adventure, outdoor exploration, and tranquil relaxation when you stay at this 2-bedroom, 2-bath vacation rental. With a fully stocked kitchen, welcoming interior, and a central location surrounded by the area's top attractions,...
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
The Hualalai Resort will host the annual Chairman’s Club event from December 1–6, 2025. Please note that access to certain resort amenities may be limited or restricted during this time for residential rental guests. We recommend inquiring prior to booking if your...
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...
Oceanfront Kona Beach House
Very rare spot, one of the few single house by Alii dr. and just on the water.Drift away to paradise in this amazing 2-bedroom, 2-bath Kailua-Kona oceanfront home. The endless ocean views will keep you coming back year after year. Begin each day with a cup of Kona...
Aloha Chic Penthouse Vistas
Summary:Bright, modern, and spacious. Completely remodeled in September 2021. Thoughtfully designed to elevate your Maui experience. This one-bedroom, one-bathroom condo features luxurious touches throughout paired with beautiful ocean views. Located in sunny Kihei, all...
Quiet Hilo Cottage, Prime Location for Beaches, Snorkeling, and Surfing
Welcome to The Nene Hideaway! Nestled one block from Richardson Beach in Hilo, Hawaii, this delightful, two-story stylish cottage is the perfect retreat for guests seeking a serene beach getaway. This adorable, updated property with jungle views is ideal for couples,...
Spectacular Ocean View Front Row 2 Bedroom Condo! H-209
Aloha, we would like to welcome you to a beautiful ocean front condo designed by Peter Rusnak. Hawaiian decor with island style furnishings throughout the unit. You will experience Hawaii while relaxing in a luxury 2 bedroom condo. H209 is a quiet condo located in the...
Discounted! Partial ocean view condo with pool & just steps to beach.
WOW- discounted rates on the beach in N Kihei!! Stay with us while they continue the restoration efforts on the property from the Feb 2025 storm. The 4 oceanfront condos were damaged, but our condo and much of the common areas did not sustain any damage. In July, they...
Kauai Vacation Rental - Kuhio Shores 319–Oceanfront, Sunset Views, A/C!
Enjoy spectacular ocean views in one of Koloa’s most sought-after oceanfront condominiums. This south and west facing 2-bedroom, 2-bath corner condo has a unique view of Kauai's unsurpassed sunsets. Floor to ceiling windows, an elevated position on the third floor and...
#37 - Stunning Unit with Ocean View
This condo sits OCEANFRONT on the Sea Mountain Resort at Punalu'u Black Sand Beach. It is a spacious one-bedroom unit, fully furnished with laminate and ceramic tile floors throughout. The uniqueness of this Polynesian style condo with a modern flair is that it is a...
Wonderful luxury resort townhome, on golf course, near pool ~ Olu'Olu (MLF905)
Summary:Mauna Lani Fairway Luxury Town HomeSwim, Golf, Relax, Rejuvenate, Walk, Run, Snorkel, DiveThis vacation rental accommodates 6 persons.The Space:Please note, effective Jan 1st. 2026, Hawaii's Transient Accommodations Tax will increase from 10.25% to 11% for all...
Kaanapali Alii | 373
Kaanapali Alii 373 is a luxurious ocean view vacation rental located in the heart of Maui's renowned Kaanapali Beach. This spacious condo over 1,700 square feet offers breathtaking views of the Pacific Ocean and the islands of Lanai and Molokai from its private lanai,...
Coastal Chic Condo with Ocean View & Full Kitchen
Step into a bright and airy beautiful condo, where modern elegance meets coastal charm. Expansive windows invite natural light to flood the open living space, offering breathtaking views of the marina and the sparkling Pacific Ocean. From your private balcony, enjoy the...
COMPLETE REMODEL! BRAND NEW EVERYTHING!!! AC and POOL!
**FAMILY FRIENDLY**If you are looking for a modern, luxurious retreat in Wailea with BRAND NEW EVERYTHING, look no further! This unit was completely gutted to the studs and every item was purchased brand new. Guests can enjoy:— Modern, deluxe kitchen with all new...
Beautifully renovated studio, shared pool and bbq, walk to beach
Prince Kuhio # 234Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome to your luxurious island retreat in the heart of Poipu, Kauai! This beautifully renovated studio condo...
★Jump Start The Road to Hana at Ocean Lookout! Private Hot Tub+Pool Access + AC
Escape to Ocean Lookout, a stunning private home located on Maui's dramatic North Shore, and discover the real Maui while jumpstarting your journey to the Road to Hana. With its breathtaking whitewater ocean, cliff, and Haleakala summit views, Ocean Lookout is the...
Beach Front 180 Degree View Of The Ocean - Gorgeous
Serene beachfront estate located in a quiet cul-de-sac on the beautiful North Shore of Oahu. Three bedrooms, two bathrooms inside main home and one half bath and shower outdoors. Kitchen is modern and kitchen table looks out onto a breathtaking view, as does the living...
Unobstructed view of Molokai from our Lanai. Watch the Whales!
Recently remodeled and continuously updated two bedroom condo located on the second level with no one above you! Master bedroom with ensuite bathroom is on the main level. It is a peaceful bedroom with a king size bed, ample closet space and a flat screen televison. The...
Elegant & Peaceful, Minutes Away From The Beach & Airport!
Tucked away in a friendly family neighborhood, this island jewel will provide you with a relaxing place to come home to after a satisfying day of Big Island adventures. Key Features Include:* 1,600 ft. elevation - while the coastline radiates the warmth of the day, you...
Perfect Hanlei Location! Walk to beach/town. Newly Remodeled w/AC TVNCU-4237
This newly remodeled beach house is very comfortable and in a great location. It's a couple minute walk to the beach or town. The house revolves around a great room of kitchen, living room and dining room. It's ideal for eating, drinking and hanging out after a day at...
Luxury Oceanfront Mahana Kaanapali. WHALE WATCH FROM LIVING ROOM SWIVEL CHAIRS!
"We literally watched the whales and turtles from the living room chairs. We have stayed all over Maui over the past 20 years and this was by far the most enchanting" -Anna 2025"Our selection was based on the closeness to the water, views from the bedroom and living...
Lae Nani 535 - Spectacular Beach Front - Quiet and Private with Bedroom AC & WD
Welcome to our beach front home on the Island of Kauai! Lae Nani is a beautiful resort located on the east side of Kauai, just south of Kapaa. Our location gives you easy access to the North Shore (Napali Coast) and South Shore (Poipu, Waimea Canyon) and there are lots...
Exclusive area. SW Infinity Pool, Putting Green, Private yard, Ocean Views
The Villa itself is absolutely gorgeous with everything one could possibly ask for in luxury and amenities. Twice featured in West Hawaii Today for its outstanding qualities, you will find your own private sanctuary, Collessie by the Sea, nestled in an exclusive...