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.
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,...
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...
Wailea Ekahi Village 22F - 2 Bedroom Ocean View Condo
Wailea Ekahi 22F is located in an ideal location, closest on property (a short walk) to Keawakapu Beach and the Wailea Ekahi beachfront swimming pool and recently remodeled beach pavilion. Whip up some happy hour drinks and snacks in your vacation rental and then stroll...
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,...
Poipu Kapili 50-Ocean & Pool View One Bedroom - Newly Installed AC
Poipu Kapili is home to ideal oceanfront condos. The location of Poipu Kapili Condo #50 is in the midst of the impeccably maintained luxury 52 villa complex.Upon entering Unit 50 you will feel yourself immediately relax with Island interior, high ceilings trimmed in...
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....
Oceanfront Condo Halii Kai 14D
Take advantage of this spectacular panoramic oceanfront view of the coastline when you book this vacation rental condo. Experience a real treat when you book between mid-December through early May and get a chance to see the friendly whales frolicking just off our...
❤️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...
GORGEOUS OCEANFRONT GROUND FLOOR UNIT—PARADISE FOUND
Non-Smoking Deluxe Unit - Sleeps 4 adultsLocated on Maalaea Bay, Kanai A Nalu is called “Maui’s best kept secret.” Quiet, romantic and tropical, it’s located at the north end of Maalaea Bay in South Maui. A spectacular setting for your Hawaiian vacation. Enjoy...
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....
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...
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...