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.
KBM Resorts | FREE CAR | Mahana | Oceanfront | Stunning 2-Bedroom Condo! MAH-419
Oceanfront 2-bedroom villa at Mahana Resort with panoramic views of Lanai and Molokai, floor-to-ceiling windows, a furnished lanai, and elegant interiors-perfect for whale watching and sunsets.** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii...
H-G-T-V type Renovation, Million Dollar view starting at only $210/night!
This unit was renovated by an HGTV interior designer and is virtually identical to another unit that was featured on the HGTV show House Hunters that aired in November 2013. Unit 109 offers the most luxurious accommodations for the best value. Unobstructed ocean view,...
Ku'u Lei Villa: Condo w/ AC, Shared Pool & Spa
Welcome to your Hawaiian home away from home, Ku’u Lei Villa, on the fourth tee of the Princeville Makai Golf Club. With beautiful golf course and mountain views, this spacious three-bedroom, three-bath townhome sleeps six guests comfortably and even welcomes a small...
Cliffside Home w/Gorgeous Ocean Views and Tropical Garden. Paradise Bluff
Paradise Bluff is a beautiful home perched on the cliffs of the small seaside town of Laupahoehoe. Relax, take a deep breath, and enjoy the Aloha spirit and traditions of the Big Island of Hawaii. Located on the spectacular Hamakua Coast between Hilo and Waimea,...
All New! Beachy Chic Remodel, Ocean front with AC
All new! Fully Air conditioned and decorated with a warm beachy chic vibe! Top floor, direct oceanfront.The spacious bedroom offers a new king bed. The living room has AC, new full size sleeper sofa, Smart TV, Free wifi New kitchen is fully equipped. Steps to the...
Amazing Direct Ocean Waterfront - 1bd/1ba Condo in Kahana Maui!
Come visit our spacious top floor corner oceanfront condo with fantastic views of Molokai and Lanai. You can watch spectacular sunsets and enjoy whale and turtle watching from your private lanai. Conveniently located between Kaanapali and Kapalua, the condo is ideal for...
Waipouli Beach Resort - Ground Floor #E103, 2 King Masters Suites
Aloha~Why should you stay in our ground floor unit? Pride of Ownership Shows! We have decorated our 1300 square foot unit with high end amenities~ Our unit shows like a model. Our unit features dual master suites opposite sides of the living room. The kitchen is simply...
Ocean Front-Ocean View Condo Free Parking & Beach Gear
Great condo, awesome view and it includes free parking ($29/night value) and the best selection of free beach gear in Waikiki. One of the best ocean view apartments in Waikiki, ideally located and the best equipped, with everything you will need to have a wonderful...
Hawaiian Bungalow Steps to the Beach 1BR 1BA Ocean View with AC
Welcome to Hale Makani Aloha, a gorgeous 1 bedroom and 1 bath condo located conveniently just steps away from the longest stretch of sandy beach on the Island of Maui. Given our excellent location in the heart of Maui and just 10 miles from the Kahului Airport, you will...
Lanikai Hillside Cozy Cottage with Spectacular Ocean View with Mokulua Islands.
This beautiful hillside cottage with stunning ocean view offers the perfect getaway for a couple, small family, or up to four vacationers . Ideal for Military personnel transferring to or from O'ahu who need a month or several months rental. Bedroom has partitioned...
Spectacular Diamond Head and Ocean Views! Free Valet Parking, Wi-Fi, Pool!
Waikiki Beach Tower #3602 – 2470 Kalakaua Ave.This spacious, centrally air-conditioned two-bedroom, two-bath condo (1025 square feet plus large lanai with table and chairs) has one of the most breathtaking panoramic ocean views in Waikiki, plus an unobstructed Diamond...
Papakea L106 60%Off Last Minute April & May Deals Ground Floor OceanFront Condo
The Stice Team — Powered by Gather Vacations. Maui Born and Raised Professionals. Your Local Experts in Crafting Unforgettable Stays.Welcome to Papakea L-106. This ground-floor, oceanfront two-bedroom, two-bath condo comfortably sleeps up to eight and is located in...
Pua Oriana: A Polynesian Tropical Retreat
E komo mai — welcome to our hale. Welcome to the Pua Oriana – a mix of Hawaiian and Samoan language, ‘pua’ meaning flower, and ‘oriana’ means the flower that adorns a woman’s head. Enjoy the space and the grounds with 880 acres of pristine gardens, walking...
Regency 721 - A Peaceful And Private 3 bedroom Condo In Sunny Poipu
This 3 Bedroom, 3 Bath Condo features Hawaiian style furniture and décor, a wonderful granite kitchen with all the amenities of home. The master bathroom features a jetted tub and walk-in marble shower. The living area is complimented with a TV. Beautiful garden views...
500 feet to the 🌊, 1000 feet 🏝 and 🐢
The most incredible location, nestled among the trees and flowers, over an acre to overlook, and stunning sunsets, and the famous Poipu Beach is just steps away you’ll never want to leave our beautifully styled 1 bedroom, 1 bath condo. We have everything you’ll need...
Chic Kihei Beach Retreat with Ocean Views across from Charley Young Beach
Our 2 bed, 2 bath unit has been remodeled, including a three zone mini-split A/C system, quartz counter tops, tile floors, open concept kitchen, and custom tiled showers. New stainless steel appliances, including full-size fridge, dishwasher & microwave, large capacity...
Papakea J405: Luxurious Ocean View Penthouse, 2 Min Walk to Beach, Many Updates!
Experience the ultimate Maui getaway at our top-floor penthouse condo, offering breathtaking ocean views and a plethora of amenities to make your stay unforgettable. Located just a 2-minute walk from the beach, this exquisite three-bedroom condo is perfect for families...
604 - Luxury Oceanfront - top floor unit with A/C and a spectacular ocean view!
*NEW* unit 604 now has air-conditioning! This upgrade will provide a more comfortable and cool environment for our guests! This sixth (top) floor oceanfront condo at the Kihei Surfside Resort is located on the sought after ocean side of the elevator, and has a...
KAANAPALI. FULLY REMODELLED - BEST VALUE G203
G203 5 star studio located in the heart of Kaanapali at the Maui Eldorado Resort. Surrounded by palm and plumeria trees with expansive views of the main pool and a glimpse of the ocean. Perfect for the couple seeking an exquisite luxury and affordable Kaanapali condo...
Minimalist 1bd with magical views
Oceanfront Designer Condo with Huge Views and Central A/C! Lauloa 402 is a 1-bedroom, 1-bathroom condo that was recently renovated and located on the 4th floor. Unit 402 can accommodate up to 4 guests. This spacious, modern condo will provide you with all the comforts...
Turtle Bay Corner Condo Overlooking the Fairway - Kuilima Estates East
Enjoy the best of what the ‘fabled North Shore’ has to offer in this authentically designed Hawaiian-beach-themed unit, that sleeps up to four (4) adults, with Resort-style amenities at your doorstep, including snorkeling beach access, swimming pool, tennis courts,...
Kauhale Makai 411: 2 Br w/Stunning Panoramic Ocean Front Views Sleeps 4
Thank yourself with a stay in this newly remodeled condo at Kauhale Makai, the village by the sea. This remodel encompasses the stay-at-home charm of Hawaii with the added luxury of fresh and clean. Bask in the sun and AC while taking in the breathtaking view of the...
A/C, Townhouse ideally located, Nihilani 25A
This beautifully furnished three-bedroom, two-story townhouse is ideally located near the pool and BBQ area, with space between you and your neighbors. With nearly 1900 square feet of living space, there is plenty of room for everyone to be together as well as have...
Tropical Gardens,4 Bdr, Large Yard, Pool, 5 min Walk to Beach,Koi Pond, Kailua
Stay in comfort as long as you wish. 30 day minimum lease, shorter stud are of longer stays are welcome. Contact Us for Details and RatesHawaii Tax ID # available upon requestHale Pulelehua “The Butterfly House” has an open spacious Kailua feeling inside and out....
Loft Oceanfront Paradise with Pickleball!
About this space Aloha! Welcome to our remodeled 3-bed, 3-bath condo with ocean and Molokai views from the wrap-around lanai. Watch sea turtles, relax by the new pool, or head to nearby pickleball courts just minutes away. The space - Freshly renovated resort: new pool,...
MauiTime at Wailea Ekahi, easy walk to beach, dining, shopping, 4 pools plus...
ALERT: Beginning Jan 1, 2026 the State of Hawaii Transient Accommodation Tax (TAT) goes to 11% from 10.25%It’s great to be alive in 2025!So many rumors surrounding Maui Vacation Rentals. The truth is Maui is open and ready for your business with the spirit of Aloha!In...
"Beach Vibes in Poipu" Remodeled, Ocean view , AC, and Washer Dryer - Rare Find
Experience island living at its finest at our beautifully remodeled ground-floor condo in the heart of sunny Poipu, Kauai! Located in the highly desirable Kiahuna Plantation Resort, Unit #146 (Building 22) offers an unbeatable blend of modern comfort and charm—just a...
Maui Kamaole H-101 | Oceanfront + Ground-Floor
You’ll enjoy the best of Maui when you stay at Maui Kamaole H-101, a garden-level condo within a low-rise complex. There’s no better way to experience the natural beauty of the island than to stay in a home that opens directly onto beautifully landscaped gardens....
❤️PiH❤️ HOUSE OF JOY★ Private Heated Pool & Spa ★ Free 2025 Hilton Resort Passes
Brought to you by Paradise in Hawaii Luxury HomesWelcome to House of Joy, part of our Hawaiian Luxury Collection. House of Joy at KaMilo is a wonderful home that sleeps 12 with a stunning backyard oasis including private pool and spa with stunning views of the golf...
Calming condo with balcony, patio, kitchen, gas grill & pool - snowbird-friendly
Kalanikai #112Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Your next tropical getaway awaits in this lovely condo! Located in the heart of Kailua-Kona, you're only a stone's throw...
Beach Gear Included! Waikoloa Beach Villas I22
**Complimentary Late Check Out up to 7:00pm for stays of 5 nights or more between October 1-December 19, 2025 (stay must be complete by December 19th) based on availability at the time of booking. Valid for new bookings made September 24 or after. Please message us...
Maui Resort Rentals: The Whaler 124 - Luxurious Ground Floor Corner 1BR/2BA w/ Wrap-Around Balcony, Partial Ocean and West Maui Mountain Views, Large Adjacent Lawn Area
Enjoy convenient easy access to the beach, pool, and BBQs from this luxurious 1 bedroom / 2 bathroom ground floor corner suite. Suite 124 even offers partial Pacific Ocean and West Maui Mountain views from its expansive wrap-around balcony and large adjacent lawn...
Kihei Akahi D204 - 1BR/1BA Unit With Ocean View, Steps Away From Kamaole Beach!
Book your piece of Paradise in South Kihei. Step into the elevator up to the 2nd floor and walk straight into this unique 1BR/1BA unit with a partial ocean view. The Kihei Akahi is located across the street from Kamaole Beach II & III.Kihei Akahi! This beautiful...
GORGEOUS OCEANFRONT GROUND FLOOR UNIT—PARADISE FOUND
Non-Smoking Deluxe Unit - Sleeps 4 adultsTRAVEL TO HAWAII - Beginning March 26, 2022, there will be no COVID-related requirements for arriving domestic passengers. Travelers arriving in Hawaii directly from international airports must still comply with U.S. federal...
Ground level beach chic condo directly across from the beach! Pool & BBQ!
Recently Refreshed Condo and New Listing! ***Professionally Cleaned Condo, No-Contact Check-In/Check Out*** Literally just Steps from the beach, Kihei Holiday 119 is a beautifully remodeled 2 bedroom 1 bathroom condo fronting the gorgeous sandy beaches of North Kihei....
~~OceanFRONT complex~~on the BEACH~~Luxury Remodel~~
-Sugar Beach Resort #407 has been taken down to the studs (if there were such a thing in a concrete complex but you get my drift).This is the true "Sand in toes" experience--no walking across the street to get to the ocean. Sugar Beach Resort is an OCEANFRONT complex....
Direct Oceanfront Penthouse - Makahuena 3202
About this spaceDirect Oceanfront Penthouse - All you see is WATER! NOW FULLY AIR-CONDITIONEDThe spaceImagine sitting on your lanai, overhanging the lava cliffs of the southernmost point of Kauai where you can see the sunrise and the sunset in the same day! There is...
OCEAN VIEW 2 Bdrm condo with Secluded Beach - Kahana Sunset C7
Kahana Sunset OCEAN VIEW, newly remodeled 2 bedroom, 2 bath split level condo on secluded Keonenui Bay Beach.Heated Swimming PoolKiddie PoolBBQ AreaAir conditioningSecluded white sand beachTurtle SanctuaryFree parking and NO Resort Fees!This beautiful, 2-level,...
Sunshine by the sea!nA two-bedroom with a three-bedroom suite area.
Fabulous Oceanfront Condo at the Milowai, Ma'alaeaWelcome to Sunshine by the Sea—your luxurious 2-bedroom, that can converts into a 3-bedroom suite if needed for additional guests. One of the standout features of this fabulous condo is an end unit with double lanai,...
Kamaole Sands, bldg 9, remodeled, ground floor, across the street from the beach
Condo, 1 Bedroom, 2 Baths, (Sleeps 1-4)._______________________________________________NO CONSTRUCTION TAKING PLACE ON BLDG 9, UNTIL 2025. Our goal is to provide a clean, relaxing and enjoyable vacation for our guests. Your vacation is our business to make it...
Spacious luxury home with stunning mountain & garden views
The Palm House at PrincevilleOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Escape to paradise in this stunning five-bedroom, four-bath vacation home in Princeville, HI. With a...
Garden-level condo in oceanfront complex w/ shared pool & great views
Mahina Surf 109Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Enjoy sitting in the shade of your lanai, watching the waves come in from the ocean, and making plans for an afternoon...
Waiuli Beach Cottage ~ Oceanfront at Richardson Beach Hilo Swim & Snorkel
Charming beach cottage with commanding ocean view of the best beach on the east side of Hawaii! Waiuli (Richardsons Beach) is the best for swimming, surfing, and snorkeling. What's the best thing about it? It's right across the street! Grab a mask and snorkel (there's...
LOVE the Ocean and Mountain Views*Remodeled Studio
*Please be advised neighboring Unit D515 will be undergoing exciting updates from September 8 – November 10 2025, including a brand new split A/C system, updated flooring, modern kitchen finishes, and a fully remodeled bathroom with a new tub and shower.As a reminder...
Newly Renovated Lanikai, steps to Ocean A/C, kayak, Detached Private cottage
Enjoy a restful respite in this private cozy cottage with a beautiful private garden. The Lanikai Bungalow is a private separate cottage. It has one bedroom with beautiful relaxing living spaces, full kitchen and bathroom. The cottage has a gorgeous private lanai/patio...
Wavecrest Resort A206
Get away to the island of Moloka'i, the best kept secret of the Hawaiian Islands because it is the "Real Hawaii." Experience a real Hawaiian Island of 50 years ago! Our kitchen was recently remodeled! We are in building "A" of Wavecrest, right on the ocean. Time slows...
Prince Kuhio Condo - Steps to the beach!
Comfortable studio steps away from the beach!This condo is ideal for your stay on the South Side of Kauai. You can't beat the unobstructed ocean and garden views. The condo features a king bed, sleeper sofa, small dining table and chairs with additional seating and...
Cozy Maui 'Treehouse' with lovely views and amenities
Located in the heart of Kihei, white sand beaches are three blocks away. A mere two blocks away will get you to the movie theaters, restaurants, library, cocktail lounges, open air markets, in-line skate park, tennis courts and much much more. There is a public swimming...
Studio Apartment City View Unit 817
Summary:Visiting Waikiki? Why stay in a hotel when you can enjoy all the amenities of a resort at condo prices? Unit 817 at the Ilikai Hotel is your perfect home base for a memorable Waikiki vacation! We proudly donate 10% of the profit from this vacation rental to...
🏖️Serene Resort Living | Ground Floor | Private Beach Club Access | vrKCV
vrKCV - Golf Villas at Mauna Lani Q2, Professionally Managed by Kona Coast VacationsWelcome to The Golf Villas at Mauna Lani Q2, where lush surroundings and tranquil garden views set the stage for a relaxing island getaway. This ground-floor, 2-bedroom, 2-bathroom...