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.
Kaanapali Royal Q202 Modern 2BD Condo on Kaanapali Golf Near Beach w Pool AC
Welcome to Kaanapali Royal Q-202 by Gather, a spacious two-bedroom, two-bathroom condo ideally located within the Kaanapali Resort on Maui’s stunning west coast. With serene garden and partial ocean views overlooking the Kaanapali Royal Golf Course, this peaceful...
~~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...
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...
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...
🏖️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...
Ocean View Guest home at Cool Elevation! - 10 mins from Airport & Town
Welcome to the first step of your relaxing Hawaiian vacation. At Ka Hale 'O Maluhia ("The House of Peace")! In this guest house, you will enjoy the feeling of hospitality and relaxation. At an elevation of 1,512 ft., you and your 'ohana will delight in the warmth of the...
Wailea Sunset Condo -Wailea Ekolu Village #607- Spring & Summer Get Away Special
Welcome to our piece of paradise. Why stay in a resort hotel like the Four Seasons or the Grand Wailea when you can save 75% of the cost and not have to purchase every meal in a resort hotel? You'll have a full kitchen and a gas BBQ nearby to save on meal costs, the...
Gorgeous 1BR/2BA - Great Views & Reviews
Hawaii Tax ID (TA/GE) and TMK:TA-173-216-3584-01/GE-173-216-3584-01/TMK 4-4-3-008-001-0117-000Our luxury condo is a 1BR/2BA with resort, pool and ocean views that sleeps 4 comfortably. The spacious condo is fully furnished and has AC. It's located in the Waipouli Beach...
🏖️Amazing Ocean & Sunset Views | Pool | Gated Community |vrKCV
vrKCV - Keauhou Estates Serenity 10, Professionally Managed by Kona Coast VacationsExperience Island Living with Stunning Ocean ViewsWelcome to Keauhou Estates #10, a 2,212-square-foot, 3-bedroom, 3-bathroom home nestled in the prestigious gated community of Keauhou...
🏖️Beautiful View | Concierge Included | Close to the Pool | vrKCV
vrKCV - The Shores at Waikoloa 124, Professionally Managed by Kona Coast VacationsWelcome to Your Island Retreat:Nestled in a picturesque and tranquil setting within The Shores at Waikoloa Beach Resort, our island home offers a perfect blend of peace and convenience....
Luxury Ilikai Condo, 2/2, sleep 7, Direct Ocean Front, Fireworks every Friday!
2 Bedroom, 2 Bath Condo With 2 balconies with ocean views from every room!New Luxury Renovations completed September 2020!!!This luxury beach-themed condo offers dramatic ocean and lagoon views that can be enjoyed from every room. Spectacular sunsets! Enjoy fireworks...
Updated and spacious top floor beachfront 2 bedroom 2 bathroom ocean view condon
Welcome to Hale Mahina B402. This top floor updated beachfront 2 bedroom, 2 bath condo has stunning views as soon as you walk in. This condo features a remodeled kitchen, fresh paint, new linens, & everything needed to feel at home. Hale Mahina is a very special...
Oceanfront Kihei Maui Condo. Ground Floor 1 BR/1 Bath. Sunsets!
When you stay at HKOK #113 your vacation will provide you a clean, comfortable no stress oceanfront condo with warm breezes and amazing sunsets that is affordable to boot! The owner does not like air conditioning but the ocean breezes and fans provide a natural...
❤️PiH❤️ BLUE SUNSET ★ Steps to A-Bay Beach ★ Resort Pool & Waterslide Pass
Brought to you by Paradise in Hawaii Luxury HomesWelcome to Blue Sunset, part of our Hawaiian Luxury Collection. Blue Sunset is in the front row of the Kolea community at the Waikoloa Beach Resort. This gated community is situated on more than 30 acres and boasts...
Includes Beach Gear! 2404 Waikoloa Colony Villas
Waikoloa Colony Villas 2404This vacation rental is professionally managed by ResorticaHawaiiPlease scroll down for detailed informationBedding Configuration:Master Bedroom: King BedGuest Bedroom: One Queen BedAdditional Bedding: Sleeper Sofa in the Living...
Cute 1 bedroom ground floor unit available for short and long term rentals
Available for both short and long term rentals, this large one bedroom, one bath unit has a private lanai set on the beautifully manicured, tropical grounds of Hale Kamaole Resort where the setting and large units have led it to be known as one of the best values on...
Our Kauai Island Gem - Check out our Spring Specials!
Welcome to our Island gem, Our unit is conveniently located at the Cliffs in the heart of Princeville on the Garden Island of Kauai. The Cliffs is a 22 acre beautifully manicured resort property, high on the bluff overlooking the ocean. The Cliffs units offer a quiet,...
Maui Resort Rentals: Honua Kai Konea 210 – Large 1BR w/ West Maui Mountain Views
Konea 210 is a large one-bedroom suite that offers epic sunrise and frequent rainbow views along with expansive vistas of the West Maui Mountains. The suite is ideally suited for families and couples, who will relish in this suite's abundant living space. To fully enjoy...
Charming Waikoloa Village Townhome: Swim & Explore
Feel the sand between your toes and plunge into the salty waters of the Pacific Ocean when you book this 3-bedroom, 2.5-bathroom vacation rental! Make use of all the community amenities and get competitive on the tennis courts or dive into the outdoor pool. Explore the...
Kam Sands -Innercourt- Ocean views- large lanai & very private third floor end
We have remodeled our condo (unit 6301) at Kamaole Sands to the highest standard . It is a home away from home with every convenience for our guests. A gourmet kitchen fully equipped for a gourmet chef. Granite counters with all new appliances and cabinets. Best of the...
BEACHFRONT RESORT on INCREDIBLE Sugar Beach! Kihei Sands Condos - A13
Dreaming of a warm Winter Getaway with breathtaking ocean views? Now's your chance. Our NEW LOWERED RATES make it easier to unwind, recharge, and witness whales! Our lovely Condo A13 is sunny south Kihei Maui was completely remodeled in May 2022. The new Mitsubishi A/C...
The Emerald Lotus ~ Heated Pool ~ Jacuzzi ~ Golf
Step into paradise at the Emerald Lotus, a three-bedroom haven where tropical breezes and unobstructed golf course views welcome you. Revel in incredible mountain views and a prime location above sea level, ensuring a constant flow of refreshing trade winds throughout...
Crew Rest Maui - 2BR/2BA, Oceanfront, Superior Views, A/C throughout!
**There are many rumors surrounding vacation rentals on Maui. It's true that there is a proposed ban on some short-term rentals. That bill has not yet become law, and even if it does, it would not go into effect for our property until 2031. In the meantime, Maui is open...
Turtle Rock - Ocean Front Cottage with pool
Direct Ocean Front Home completely remodeled inside and out overlooking spectacular Kahalu’u Bay with views of surfers, dolphins, whales and sunsets. This one of a kind property features two Cottages with separate Master Suites. Amenities include two bathrooms, sun...
Half Moon Hana: Beautiful 3BR Oceanview Princeville Home
Located in one of the premier resort communities in the world, this charming, newly-remodeled home provides gorgeous ocean, mountain, and golf course views. Half Moon Hana sits close to the sixth tee of the renowned Makai Golf Course and features living spaces with high...
Ocean View Condo in the Heart of Kihei!
The Kihei Akahi complex in Kihei Maui is a beautiful community that offers a range of one-bedroom condos.This condo features a comfortable and stylish living space, perfect for individuals or couples who are looking for a relaxing vacation in paradise.Inside the condo,...
KLVR welcomes you to Luana Villa 13D, Oceanfront Resort, short walk to the beach
Kaanapali Luxury Vacation Rentals welcomes you to our beautiful upper level Luana Villa at the Honua Kai Resort.New luxurious private villa steps away from world famous Kaanapali beachThis luxurious villa is located within a private garden enclave at the spectacular,...
KBM Resorts | FREE CAR | Honua Kai Hokulani | Ocean view | Studio Condo, Gorgeous Studio! HKH-423
Oceanfront studio in the Hokulani Building with sweeping views, king bed, sleeper sofa, luxury kitchen, and soaking tub. Enjoy indoor-outdoor living from the spacious lanai in this Maui retreat.*Special Offer: Book any KBM rental home in Hawaii for 6 nights or more with...
Spectacular Ocean Front, Garden Level, Corner Unit, Stunning Views for 4 in Kona
Due to last minute Christmas cancellation I'm offering a 10% discount from 12/20-12/27!!!!!This oceanfront condo located in a gated community allows you to enjoy the sounds of waves crashing on the rocks, whale and spinners dolphins watching. Unbelievable sunsets from...
Hale Ola Kai - a 3br/3ba home a block from the beach in Hanalei
TVNCU-1343 - TAT# 127-070-6176-01 - "Healthy House by the Sea"Hale Ola Kai is a three bedroom, three bath home located near world famous Hanalei Bay. The house is an elegant and modern remodeled home. The stunning interior is equipped with anything you need to make your...
Amazing Turtle Bay Condo - Kuilima Estates East
Look no further for your perfect escape to Hawaii! Nestled in the resort community of Turtle Bay, this newly updated 1 bedroom condo w/ a loft is outfitted with LUTRON Ketra lighting technology & LUTRON motorized shades and can easily sleep 4-5 guests the Kuilima...
HAWAIIAN DREAM TEMPLE - w/Private Hot Tub and Shared Pool - Permit#BBPH2012-0004
[PERMIT- BBPH2012-0004] [TMK (2) 2-7-029: 015-0000]Welcome to your ‘Hawaiian Dream Temple’ While we have been devastated by the recent wildfires in the town of Lahaina, the rest of our beautiful island is open to visitors, we welcome you anytime!This unique &...
Experience Authentic Hawaii on Oahu's West Side! 5 Minutes to the Beach!
ABOUT OUR CONDO: This is a beautiful 2 bedroom, 1 bath condo with vaulted ceilings and two separate lanais, a unique feature in the complex. Located on the third floor, the master bedroom lanai has a gorgeous view of the Makaha Valley mountain range, while the living...
🏖️Prestigious Mauna Lani Resort | Luxurious End Unit | vrKCV
vrKCV - Golf Villas at Mauna Lani L5, Professionally Managed by Kona Coast VacationsEscape to Tranquility at Golf Villas L5 - Your Perfect Island GetawayImmerse yourself in the serene ambiance of the Golf Villas at Mauna Lani Resort, where tranquility meets luxury....
1200 sqft Beach Front Penthouse just steps to Beach! Ocean Views from all rooms!
There are no other Top Floor rentals with this water front exposure in this building. An amazing way to spend your vacation! Professionally remodeled and decorated by a noted California Interior Designer. This penthouse has consistently been 'Highly Reviewed' on VRBO...
KK 310 Updated BeachFront 2BD w AC Pool
Kulakane 310 Unbelievable West Maui Sunsets from Direct Oceanfront Condo! 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,...
Maui Resort Rentals: Kaanapali Alii 3116 – Luxuriously Remodeled 2BR Oceanfront Royal Penthouse! The Crown Jewel of the Kaanapali Ali'i
Never before available for rental, this stunning oceanfront royal penthouse is one of the finest 2BR suites on offer at the acclaimed Kaanapali Ali'i. For a vacation rental experience in the heart of Kaanapali Beach, it simply does not get any better!Gorgeously...
Experience Oceanfront Grandeur: Royal Mauian #418 - Spectacular Views Await!
Royal Mauian #418 – Spacious Oceanfront Three-Bedroom RetreatRoyal Mauian #418 is a rare three-bedroom, two-bathroom condo designed for families or groups seeking both space and stunning views. With its prime oceanfront location, expansive lanai, and tasteful upgrades...
Kahana Reef 118: Completely remodeled one bdrm Ocean Front Kahana Condo
Completely remodeled Kahana Maui vacation condo with direct oceanfront views. Updates include new marble floors throughout (excluding bedroom), kitchen cabinets and appliances, imported Brazilian granite countertop, marble bathroom, carpeting in the bedroom and...
Hawaii Life Rental Presents Villas of Kamali'i 56
Beautiful end unit 3bedroom & 3 bathroom luxury condo in gated community in the middle of Princeville with gorgeous mountain and waterfall views from the large great room. The condo has been upgraded with teak and tile floors throughout and new vinyl floor planking in...
EL J218 Kaanapali Studio w Ocean Views Pool AC
Eldorado J218 Bright and Cozy Studio with Ocean View, Golf and Beach lovers delight! 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...
Kamaole Sands Condo w/ Shared Grill, A/C-Snorkel, Surf, Swim
Kamaole Sands 5-216Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Conveniently located across from Kamaole Beach III in the beautiful town of Kihei, this Kamaole Sands condo...