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.
Beachfront + Oceanfront Molokai Condo
Invitation to ParadiseWelcome. Enter and experience the Aloha Spirit you have come to the Islands to experience. Come listen to the Pacific Ocean speak to you. Come feel the sea breeze delight your senses. Come taste the air of Hawaiiana. Our sanctuary at Kepuhi invites...
Koana Breeze-Breathtaking Sunset & Ocean Views, Hot Tub Living at its finest!
This spectacular 2500 square-foot plantation-style home is perched on a hillside with breathtaking ocean views of Keauhou and Kailua Bays. Enjoy year-round outside dining with fabulous views of gorgeous Kona sunsets on the lanai, and enjoy drinks in the hot tub. We call...
Kanaloa At Kona | Enjoy Peace in Paradise!
Summary:Imagine having the privacy of your own little piece of paradise — that’s exactly what you’ll find in this uniquely located condo. Maximum occupancy is strictly enforced in accordance with local ordinances. Situated at the end of the building with stunning ocean...
Royal Kahana 510, Direct Oceanfront 2B/2.5B, Spectacular Views, AC, Sleeps 6!
Indulge in luxury in this newly renovated condo, offering 1,287 sq ft of living space and breathtaking wrap-around lanais. Located in a premier beachfront spot between Kaanapali and Kapalua. The expansive living and dining area, seating up to six, showcases panoramic...
Ailana Hale: Charming Princeville Home w/ Mountain Views & Spacious Backyard
Ailana Hale: A Serene Retreat in Princeville, HIExperience the relaxed rhythm of North Shore living at Ailana Hale, a newly rejuvenated 3-bedroom, 3-bath vacation home in Princeville. Offering 2,900 square feet of indoor space and surrounded by lush tropical...
Hale He'e - Octocondo at Alii Drive
Welcome to Hale He’e, a perfect little slice of Hawaiian beauty. Enjoy the best of what Hawaii has to offer in our completely updated condo at Kona Makai - an oceanfront complex complete with tennis courts, pool, spa and exercise room.This rarely available 798 sqft, 2...
Clean Comfortable Condo that is Steps to the Beach, Affordable w/Free Parking
Our second-floor unit is spacious with vaulted ceilings and an air-condition unit in the living area. The condo is a one bedroom that is equipped with all you need to enjoy a relaxing vacation in a tropical setting. We have free Wi-Fi , 2 wall hung LCD TV's, a 60" LCD...
KKSR#183 DIRECT OCEANFRONT REMODELED TOWNHOME. RIGHT ON WATER!
Gorgeous Direct Oceanfront Remodeled Townhome, truly stunning! Townhome#183 is very special, featuring all one could want in their Vacation Rental. It has two bedrooms & two bathrooms and is configured to accommodate up to 6 guests with a King bed in the ocean-facing...
Emmalani Court #221 - offered by Na Pali Properties, Inc.
Emmalani Court is a 42-unit, two-level luxury condominium complex located on a bluff over the ocean in beautiful Princeville, on Kauai’s north shore. Unit 221 is at the quiet end of the complex - the closest two bedroom to the ocean - and offers nearly 1500 square feet...
Colorful condo by the beach with a washer/dryer, lanai, & on-site pool
Paniolo Hale S3Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Tucked away on the beautiful west end of Moloka'i, this sunlit and colorful condo is sure to delight you and your...
Ocean Views In Paradise
THIS IS A NO SMOKING/NO DRUGS UNIT/PROPERTYCLEANING FEE covers disinfecting and cleaning, laundering etc of unit before AND after. Should you assist (at time of checkout) with tossing all your excess food and bringing your bedding and towels to me, I will refund $50 of...
Newly Remodeled Oceanview 1BD/2 Bath at Popular Kamaole Sands
Welcome to Nani Kai which means 'beautiful ocean' in Hawaiian. We are located at the most popular and sought after condominium complex on Maui, Kamaole Sands. What makes Kamaole Sands Maui's best and most popular resort-like condominium complex are the amenities which...
Great Value ~ First Floor ~ Heated Pool, Grills
A Budget Friendly Tropical Vacation Awaits You... Enjoy the New Living Room Furniture & New Granite Counters in the Fully Equipped Kitchen. There is a Bluetooth Speaker and Flat Screen TV. Eclectic décor, expertly clean and family friendly. This PRIVATE end unit offers...
🏖️100 feet to the Beach! | Spacious Private Home with Pool | vrKCV
vrKCV - Keiki Beach 6 at Kona Bay EstatesKeiki Beach Hale - A Premier Island Retreat in Kona Bay EstatesNestled just 100 feet from the beach in the exclusive Kona Bay Estates, Keiki Beach Hale offers an unparalleled vacation experience. This luxurious 5,000 square foot...
Maui Resort Rentals: Honua Kai Konea 632 – Upgraded 6th Floor Corner 2BR, Partial Ocean AND West Maui Mountain Views
Konea 632 is a luxurious 2BR/2BA suite boasting an impressive 6th-floor corner location. It offers the best of both worlds with sweeping views of the majestic West Maui Mountains as well as partial views of the Pacific Ocean and Maui's neighbor island Molokai from the...
Absolutely Oceanfront - Free Parking - Full Kitchen- full disability access.
Direct ocean-facing view not out the side of a building or looking over another balcony. On a high floor above the street noises and restaurants below.Great Location at the beginning of Waikiki and away from congested areas.Walking distance to beaches, restaurants, and...
Beautiful ocean views located minutes away from Waipio Valley
Beautiful ocean views in a rural setting just minutes away from Waipio Valley (Valley of the Kings). On the property is a fruit orchard with multiple kinds o f tropical fruits which our guest are welcome to help themselves to anything that is ripe and ready to be...
. Designer Remodeled. All Ground fl, Lovey tropical flower gardens.n
PARADISE DREAM WORLD. MAUI KAMAOLE- - Professionally decorated by a noted San Francisco designer. You will feel the relaxing atmosphere of "Magical Hawaii" with the New and lovley interior with 22 acres of lush tropical flower gardens .This is the last phase of Kihei's...
Renovated 2nd-floor condo with ocean/garden views, lanai, on-site hot tub & pool
Sugar Beach Resort 203Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome to Sugar Beach Resort #203! This attractive and newly renovated oceanfront condo has access to a...
Maui Resort Rentals: Honua Kai Hokulani 732 - 7th Floor 1BR w/ Expansive West Maui Mountain Views!
Hokulani 732 is a luxurious 7th-floor one-bedroom suite that offers expansive vistas of The West Maui Mountains with their frequent afternoon rainbows. The suite is ideally suited for small families and couples who are looking for luxurious and spacious accommodations...
Maui Sunset BR, 2BA Condo B-307 - New King Bed
Maui Sunset is the perfect vacation home on Maui. Your island days can be filled with recreation and fun. Swim in Maui Sunset's beautiful pool with a shallow end for small children or just relax on a chaise lounge by the pool or in the jet spa. This lovely resort also...
🌴Kona Alii #710 Wonderful top floor penthouse in the heart of Kona🌴
Ocean view penthouse overlooks downtown Kailua-Kona Stay right in the heart of Kailua-Kona a stone's throw from the ocean, restaurants andgift shops. This beautifully remodeled penthouse includes a high end kitchen, a large lanai anda private sundeck that overlook the...
High Floor with GREAT Ocean Views! A/C, Washer/Dryer, FREE Parking and Wi-Fi!
Waikiki Skytower #2804 – 2410 Cleghorn St.(30-Night Minimum. ALL MONTHLY RESERVATIONS ARE SUBJECT TO APPROVAL.)Enjoy magnificent Pacific Ocean views from this contemporary, updated high-floor, one-bedroom condo (585sf plus 90sf lanai with table & chairs)! With only 4...
Fairway Villas | Lanai Overlook
Summary:Come stay at this golf course front, tropical villa at the Waikoloa Beach Resort! Spend your days relaxing by the pool, golfing, kayaking, snorkeling, or going on glass-bottom boat tours! The Kings' Shops are within a short distance, where you can find delicious...
Spectacular Views from 7th Floor Oceanfront Whaler Condo Unit 751
Enjoy this elegant and luxurious seventh story condo (Unit 751) as your home on the beach. It’s right on the water’s edge in Maui's premier vacation area 'Kaanapali Beach.' Relax on your wrap-around lanai as you enjoy unobstructed views of the beach, ocean, neighboring...
Ocean-Front jewel & amazing views, here the ocean is your backyard.
Our jewel condo is a 5 Star rated by our amazing guests for our spectacular oceanfront ground-level condo. Only 15 feet away from stepping into the ocean, and the unobstructed 180% ocean views of Molokai & Lanai islands with memorable sunsets & whale watching in season...
Waikiki Fully Furnished w/pool - walk to beach!
Waikiki Fully Furnished Ready-to-rent Condo.Centrally located in the heart of Waikiki, Honolulu. Minutes away from the prime strip of Waikiki Beach, Waikiki Market, Waikiki International Market place, Honolulu Zoo, Kapiolani Park, Waikiki Shell, shops, restaurants, bus...
Pili Mai 15H - Central A/C, Pools, Gym
Summary:Modern 2-bedroom, 2.5-bath ground-floor condo at Pili Mai with central A/C and a spacious lanai opening to a grassy area. Enjoy resort-style pools, on-site fitness center, BBQs, and easy access to dining and golf. Just minutes from Poipu Beach—ideal for couples...
Maui Resort Rentals: Honua Kai Hokulani 815 - Top Floor Deluxe 2BR, Expansive Corner Floor Plan, Stunning Ocean Views!
As one of the finest two-bedroom suites available to rent at the entire Honua Kai Resort, Hokulani 815 boasts an exceptional 8th-floor penthouse corner vantage point and is among a class of the most sought-after 2 bedroom floor plans at Honua Kai.What distinguishes this...
Maui Resort Rentals: Honua Kai Konea 1032 – 10th Floor "Penthouse" 2BR w/ Mountain & Partial Ocean Views
Konea 1032 is a remarkable two-bedroom, two-bath suite boasting an impressive 10th-floor "penthouse" corner location. It offers the best of both worlds with views of the tranquil blue Pacific Ocean as well as the majestic West Maui Mountains. Oversized picture windows...
1202A Cliffs RESORT, 159.00 5/2-5/7 Super Blow Out Sale with 10 Star Reviews!
*Our NEWLY Remodeled Modern Timeless Studio* at The Cliffs Resort in Princeville-Kauai, the north side of the island, where Majestic Views are endless in every direction, is for travelers that will spend most of their time outdoors and come home to relax... We are close...
SPECTACULAR OCEAN VIEW! A/C, Wi-Fi, Pool, FREE Valet Parking, Steps to Beach!
Waikiki Beach Tower #2001 – 2470 Kalakaua Ave.If you'd like to be directly across the street from the best swimming and surfing beach in Waikiki, then this two-bedroom, two-bath Waikiki Beach Tower condo with 1150 sq.ft. interior living space (and a large 160 sq.ft....
Come explore the peace & beauty of Maui. Across from Charley Young Beach!
DREAMING OF HAWAII? We invite you to stay at our family-owned Maui Vista condo (Building One, unit 124) in sunny, South Maui. This one bedroom, one bathroom 1st floor condo is across the street from Kamaole I beach, aka Charley Young Beach, one of the best beaches on...
Private OCEAN FRONT Estate ON Turtle COVE, Napili. MOST Spectacular Location
THE MOST MAGICAL PLACE ON MAUI! SNORKEL WITH TURTLES, WATCH SURFERS FROM YOUR LANAI AND ENJOY EXQUISITE DIRECT OCEANFRONT DINING, TRULY A TROPICAL PARADISE!!Jacuzzi, Pool Table, Dry Sauna .....Papaua Paradise offers you 5 bedrooms in this 4,000 square feet home on the...
Ocean views just steps to the beach
Kahana Reef 208 is a 1-bedroom, 1-bathroom condo that comes equipped with a modern split A/C system in the living room and pool/ocean views. There are elevators at this property. Unit 208 can accommodate up to 4 guests. The master bedroom is thoughtfully designed with...
Beach Bungalow, Walking Distance to Everything
Our completely remodeled tropical retreat is located in the highly desirable area of South Kihei, which is renowned for its beautiful beaches and proximity to restaurants and shops. This ground floor condo opens up to a lanai with a tropical garden view – the perfect...
Dolphin House: 4 BR Poipu Luxury Home with Heated Swimming Pool & Fitness Access
Introducing the Dolphin House, our private 3,700 sq ft 4 bedroom, 3 full bath, 2 half bath home for 8 guests, located on a large corner lot in an upscale quiet Poipu Beach neighborhood, Kiahuna Golf Village, and featuring a beautifully landscaped private yard complete...
New Listing Hale Mahal - 3 AC bedroom newly renovated Princeville Home Sleeps 8
This gorgeous, fully furnished 3-bed, 2.5-bath home in Princeville features an ideal open-concept floor plan. With newly remodeled bathrooms and AC in all of the bedrooms, this home is your perfect home away from home. Enjoy movies and TV with a 90” 4KTV in the living...
KBM Resorts | FREE CAR | Honua Kai Konea | Mountain view | Gorgeos 1-Bedroom Condo with included Beach Gear! HKK-816
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
'PONO PLANTATION COTTAGE' SUMMER IN PARADISE-3 BEDROOM
Aloha and Welcome to our 'Pono Plantation Cottage' your private Maui getaway.***CHRISTMAS SEASON HAS A MINUMUM STAY OF 8 NIGHTS***Nestled hillside across from the beautiful Ka'anapali Ocean Resort. Relax in vintage Hawaiian comfort in our spacious 3 bedroom, 2 1/2...
Sweeping Ocean Views! Gorgeously Renovated Luxury Suite! Free Parking & Pool!
Waikiki Beach Tower #1903 – 2470 Kalakaua Ave.INCREDIBLE unobstructed ocean views! Bask in the luxuriousness of this spacious 2-bedroom, 2-bath suite, fully renovated from top to bottom (Dec 2017) with high-end touches including mahogany cabinets and intricately...
Panoramic Views, Upgraded 2 bed, 2.5 baths, AC
Special 10% discount is offered from Feb. 17 to Feb. 28 due to construction that will partially affect the lanai view!Breathtaking views of the ocean, coastline, lush green hills, and palms! With a picturesque ocean view, our top floor condo offers privacy, cooling...
Lani Kai - Beachfront on Hanalei Bay with Sauna, Hot Tub and Fire Pit
Nestled along the serene shores of Hanalei Bay, Lani Kai, translating to "Heavenly Ocean Home," welcomes guests to its newly refurbished splendor. This spacious four-bedroom, four-bathroom abode caters perfectly to large families or couples seeking ample room to relax...
Private | Oceanview | Spacious | Bright 3BR House
Welcome to Malulani Green Haven! This private 3bd/2ba home is located in a gated, quiet cul-de-sac neighborhood right in the heart of Kailua-Kona. You'll enjoy a spectacular panoramic ocean view from the backyard lanai and a view of Mauna Loa on the opposite side. The...
Spacious Condo Paradise at Kuilima West
***WE ARE ON OAHU, AND CONTINUE TO WELCOME TOURISM***Welcome to your spacious 2 bedroom, 2 full bath, PLUS loft comfortable deluxe condo on the North Shore of Oahu. We are in Kuilima Estates West, which is next to the Turtle Bay Resort. There are 3 pools , tennis...
Quaint studio in the heart of Kaanapali
E Komo Mai “welcome” to Maui Eldorado K211! This tropical Maui Eldorado condo is located in the heart of Kaanapali, one of the world's most well-known destination resorts. It's ideal for a romantic getaway, as well as the family looking for kid-friendly beaches and all...
PICTURESQUE LAGOON & OCEAN VIEWS
Beautiful views are seen from anywhere in this comfortably decorated condominium. Sliding glass doors give access to two spacious lanais where views of the Pacific Ocean, Duke Kahanamoku Lagoon, and Ala Wai Yacht Harbor. This amazing, 1000sq.ft, ocean-view condominium...
Ahe Lani By Parrish Kauai - charming cottage steps from Lawai Beach
"Heavenly Breeze" also know as Ahe Lani is a quaint 2 bedroom cottage located near two of the best beaches in Poipu. Lawai Beach is to your left and Baby Beach is to your right, so choose your direction and in 200 plus yards you will enjoy the sun and sand. This cozy...
Paia Surf Condo
Classic Paia surf condo located on the first floor of Kuau Plaza centrally located on Maui's north shore. Your private patio leads out to a large communal lawn and palm trees. Mama's hidden beach is only a two min walk, Ho'okipa a two minute drive, a 5 minute drive to...
KBM Resorts | FREE CAR | Mahana | Oceanfront | 2-Bedroom Condo with Beautiful Nightly Sunsets! MAH-611
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...