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.
View whales from modern Top floor Oceanfront condo. Maalaea, Haleakala sunrise!!
Recently remodeled. New everything! New flooring throughout. New Beautiful Hawaiian Bedroom King set with a firm Beauty-rest mattress bed with custom closets. New A/C. This place is great for honeymooners with the ocean making waves every night.To get your attention...
NEW! Sunset Hideaway w/ Beach Access, Pools, Tennis & A/C!
Experience breathtaking views of Hanalei Bay and Bali Hai from this delightful two bedroom condo, ideally located in the serene area of Hanalei Bay Resort.This second-floor condo showcases distinctive island-themed decor, air conditioning, a fully equipped kitchen, an...
Wilikoki - Beachfront Vintage Home on Hanalei Bay
TVNCU-1105 - TA# 168-945-4592-01Enjoy watching the surf, sunsets and a view of Hanalei Pier from the deck of this great family-friendly oceanfront location. This is a special heritage Hanalei home, steeped in history, reflecting a taste of Hanalei's past. Wilikoki is a...
Beautifully updated ground floor condo. Just steps from the beach and pool!
Walk to beautiful beaches, soak up the Maui sunshine, and come home to the comfort of your own lanai/patio when you escape to this well-appointed condo in Kihei. Open the sliding glass doors to let in the cool ocean breeze, prepare island-inspired breakfast in the fully...
★Jump Start the road to Hana at Haleakala Cottage-PRIVATE HOT TUB +ACESS TO POOL
Welcome to Haleakala Cottage at Huelo Point Lookout, your ideal starting point for a Hawaiian adventure, especially if you're planning to explore the iconic Road to Hana. Our cozy cottage on Maui's unspoiled north shore is surrounded by lush gardens and organic...
Hanalei Plantation Villa: Secluded, Pool, Hot Tub, AC & Ocean Views
Nestled into the idyllic north shore of Kauai, this 4,000-square foot custom villa was designed by Hawaii's renowned architect Mark Eyler. The architecture and interior design blend Hawaiian, Balinese, and Asian elements with a contemporary style, offering unparalleled...
A Modern Mix Waikiki Edition: 1 Br w/ Free Parking
***Amenities recreational deck renovations has begun. The renovation timeline is currently set from April 2025 - for the next 12-14 months (April - June 2026). Pool, hot tubs, grills, etc. will not be available during this time. Price has been adjusted due to...
Sunset Oceanside Condo
Don't waste your trip to Hawaii on an average rental. Treat yourself to this Ocean view Condo with a pool. A private lanai overlooks the Kahalu'u Beach Park, you'll delight in morning coffee with ocean sounds and surf watching. Then relax in the evening with sunsets and...
Stunning Ocean Views - Hualalai Resort- 18th Fairway - Prime Location - Golf Cart Included
Magnificent Garden Level Villa located on the #18 hole of the Hualalai Jack Nicklaus Signature Course. Enjoy white water views and spectacular sunsets from this highly desirable location at Hualalai Resort. Listen to the ocean and whale watch during the winter months...
Puamana Retreat by Gather: Oceanfront 3BR w/ Lanai & Resort Amenities in Lahaina
Welcome to Puamana Retreat by GatherDiscover the ultimate oceanfront retreat in this beachfront townhouse, where breathtaking views and endless adventure come together in perfect harmony. Situated on the channel between Maui and Lanai, this property offers unmatched...
Beautiful South Maui Top Floor Condo with Ocean & Mountain views!
Aloha & E Komo Mai to our South Kihei Town condo!This spacious 2 Bedroom Ocean View corner condo is located on the top 4th floor of the B building in the Kihei Ali'i Kai complex. This condo is walking distance to many fantastic shops, restaurants and other amenities....
Quiet and Beautiful Place for a Hawaiian Getaway!
A quiet and beautiful setting for a wonderful Hawaiian getaway. Our condo was built in 2000 and is one of the newest in the Maui Kamaole complex We recently updated all the furniture in the unit including new chairs and a new pull out couch. The condo is quietly nestled...
Mahana 717 - Central AC, Oceanfront, Two-Island Views!
Escape to Maui – 10% discount for 7 night or longer stays; and also offering a 10% discount for those rare times we have a gap to fill, within 14 days or sooner. Be impulsive, book that last minute flight, go to Maui! This fully air conditioned, oceanfront 1BR/1BA...
🌺Sunrise & Sunsets Gorgeous Everyday! Next to Amenity Center! 🌺Club Member
Effective April 2024 to November 2024 the Mauna Kea will be enhancing their hotel. Full beach and amenity access still prevails. The Westin Hapuna Golf Course remains open, while the Mauna Kea course is getting a make-over.Welcome to Wai'ula'ula' at the Mauna Kea...
Wai'ula'ula A202 - Upcountry Residence
This upper-level, ‘upcountry’, oceanview residence offers a great room with sliding glass pocket doors for indoor/outdoor island living, a handsome kitchen outfitted with premium appliances and granite countertops, as well as a dining table for six. Additional...
Peaceful Condo w/ Amenities: Steps to Beach!
Turn back time with a blissful getaway at this lovely 1-bedroom, 1-bath vacation rental. Here in Maunaloa, you'll escape the crowds of more developed islands and enjoy secluded beaches, scenic trails, and breathtaking landscape views. By day, soak up the sun with a game...
Newly Renovated in 2024! E22 Waikoloa Beach Villas
Waikoloa Beach Villas E22. Newly Renovated in 2024!Please scroll down for detailed information:Bedding Configuration:Master Bedroom: King BedGuest Bedroom: King BedLiving Room: Sleeper SofaAmenities:Beach Equipment: All of our vacation rentals include beach towels for...
Hualalai Palm Villa 126A - Perfect location along the15th Fairway!
This well appointed Palm Villa rental, at the Four Seasons Resort Hualalai, overlooks the 15th Fairway of the beautiful Jack Nicklaus Signature golf course. Sweeping ocean views beyond the golf course combined with the Villa's casual elegance make this the ideal private...
New Luxury 5BR Princeville Estate with Pool
This Luxury Pool & Spa Estate has it all! Panoramic Views of Hanalei Bay, Lumahai Beach, Bali Hai, Mountains, Waterfalls, Rainbows, backing to hundreds of tropical acres and fruit trees! 5 Bedrooms, 5.5 Baths, Separate Living Room with 85" HDTV, Fully Equipped Gourmet...
Our home burned but NOT our VACATION RENTAL! It's our income! 1 month minimum.
You simply cannot beat the view! This unit has a great floor plan. Approx. 700 sq. ft living space and 96 sq. ft. covered lanai. The ideal place to relax or plan your excursions. Cozy, inviting, yet spacious you will feel like you found your 'Home in Paradise'!Greet the...
Kona Isle B3 No Stairs, Fully Remodeled, Beautifully Decorated: True Gem!
Kona Isle, Unit#B3 is a fantastic addition to Knutson & Associates Property Management! We're proud to represent this beautiful fully remodeled, ground floor unit.Enjoy notable features to include: No Stairs, AC Unit in the Living Room, Open Floor Plan!You'll notice...
Gorgeous 2 Bedroom on Golf Course with Ocean View!
Welcome to our home in paradise! Start or end your day on the large peaceful (newly renovated) lanai - complete with wet bar and wine fridge - with a view of the golf course, pool area, and peek-a-boo ocean views. During our visit this summer, we replaced the wetbar,...
N34 Fairway Villas at Waikoloa Beach Resort. Golf Discounts at Waikoloa Beach Re
Waikoloa Fairway Villas N34Please scroll down for detailed information Bedding Configuration:Main Bedroom: King BedGuest Bedroom : Two Twin BedsLoft: Queen BedWaikoloa Beach Resort Gold Membership Golf benefits (discounted tee fees at the Waikoloa Beach Resort Courses)...
Aloha Condos, Hanalei Bay Resort, Condo 6303, Ocean View, AC
A top floor luxury condo, with one king bedroom PLUS LOFT. The majestic 180 degree ocean to mountain views overlook Hanalei Bay, Bali Hai, and the surrounding mountains that hug the coastline. This privately owned condo has vaulted ceilings which provide lots of light...
Kaikea Modern 1Ba Lanikai Cottage: Stylish & Private - 5 Min from Lanikai Beach
Welcome to Kaikea - a tropical oasis nestled just a short walk away from the pristine white sand and turquoise waters of Lanikai Beach, offering an unparalleled experience of luxury and relaxation. Comprised of one separate structure - newly built in 2018. Featuring...
Poolside Lanai Villa l Parking, Sunset View
Summary:F211 | TA-018-220-0320-02Walk to Kauai’s top beaches from Villa F211, surrounded by lush tropical landscaping in the heart of Poipu. Relax in the resort-style pool or waterfall hot tub, stay active at the fitness center or tennis courts, and return to your...
Maui Resort Rentals: Luana Garden Villas 14C – Modern 3BR Villa at Kaanapali’s Newest Luxury Residences!
This luxurious brand-new 3 Bedroom/3 Bath residence is conveniently set within Enclave Three of the Luana Garden Villas. Villa 14C's north-facing orientation offers a Shady respite from West Maui's legendary endless sun and its designation within our "Elevated"...
Hawaii Décor W/Kitchen, Lanai, WiFi–Kamaole Sands
Kamaole Sands unit #6204: When guests enter this condo they will recognize the stylish hardwood floors that flow throughout the entire space. The open-concept layout and design were curated with style and comfort in mind so that guests will find plenty of spots to kick...
Luxe Private Princeville Retreat Near Hanalei Bay!
Delight in the very best of Kauai from the comfort & convenience of this spacious private retreat! Perfectly situated in the heart of Princeville just minutes to Hanalei Bay, enjoy relaxing on Anini Beach, a round of golf at Makai Golf Club & luxury resorts simply a...
Resort-Style Home on Keauhou Bay: Great for Groups
'Hokukano Bay House' | Featured on 'Temptation Island' Season 1 | Watercraft Provided | Multiple Lanais | Family-Friendly Pool AreaWith indoor/outdoor views of the ebbing tide, a backyard oasis that invites introspection and adventure, and a 6,667-square-foot interior,...
Wailea Grand Champions | 152
Relax on your private lanai at Grand Champions #152, perched upon the second-floor, and enjoy views of manicured fairways, putting greens, and tee boxes as golfers tackle the Wailea Golf Course. This vacation rental is ideally situated to showcase Maui’s natural...
Laidback Island Living Close to Beach & Shopping
Welcome to Larae’s Place! This cozy 3BR/1BA home comfortably accommodates up to 7 guests. Located minutes from local beaches, shopping, and the airport, it`s perfect for exploring Hilo. Relax in the outdoor dining area and enjoy all the essentials needed for a...
Luxury Home in Nohea with Private Pool & Spa
Step into island living with Abita Luxury Rentals at this nearly 3,000 sq ft, 3-bedroom, 4.5-bath home in Nohea at Mauna Lani, built in 2021. Designed with comfort and sophistication, this private retreat offers a pool, spa, and lush tropical surroundings. Perfect for...
Breathtaking Oceanfront 5 bedroom - Puamana 150-1
Aloha! Welcome to your Maui Oceanfront Dream home, Puamana 150-1, nestled in a secure, serene setting that withstood the Lahaina Fire.Thankfully, a tropical haven of 130 properties, including this home on the south shore of Puamana, were spared from the Lahaina Fire....
Absolute Oceanfront at Keauhou-Kona Surf & Racquet Club 5-204
*** Please note the pool will be closed 4/15/2024-5/3/2024 for replastering ***LOCATION: Oceanfront Kona Coast/Kailua-Kona, Big Island of Hawaii, USA. 25 minutes south of the Kona International Airport, within walking distance of shopping, restaurants, movie theater,...
Stunning Koa Resort 3bd Villa with private Jet Spa
Discover our spacious corner townhouse villa at Koa Resort, opposite Keaka, Kalepolepo & Waipuilani Beach Parks. Adjacent to the Humpback Whale National Marine Sanctuary Visitor Center, it's a nature lover's paradise. With room for 8 guests, it's ideal for family...
Live On the Ocean and Sleep to Surf Sounds in Idyllic Poipu. Trade Winds & AC.n
Our comfortable, third-floor, south shore condo is right ON the ocean so you will SEE --and HEAR-- the sound of the surf as soon as you open your front door. The condo, with stylish, contemporary furniture, boasts a comfortable California king bed. Relax "at home" and...
Ocean View Close to Airport & Beaches
Conveniently located just minutes from the airport & white sandy beaches and 10-15 minutes to the heart of Kona town, this vacation home has everything you need for a truly memorable stay in paradise! This rental is the upstairs unit of a two unit home with its own...
Park Lane Ala Moana 7501
Welcome to Park Lane, an exquisite residential resort community conveniently located in the heart of Honolulu (direct elevator access to the world-class Ala Moana Shopping Center and across the street from Ala Moana Beach Park). The elegantly designed 3 bedroom, 3.5...
Bright Haiku Studio: Patio + Rainforest View
Welcome to the 'The Kahili!’ Surrounded by the lush rainforest, this 1-bath studio provides the perfect backdrop for your next tropical retreat! Complete with a private patio, well-equipped kitchen, and a rainfall showerhead, this newly built vacation rental has...
This beautiful beachfront Hanalei Bay home is located steps from the sand
This beautiful beachfront Hanalei Bay home is located steps from the sand on Kauai's majestic north shore. It offers panoramic views of an iconic beach and its surrounding mountains within a quick walk to the Hanalei Pier for surfing and swimming and the Hanalei River...
Ground floor Condo with private golfside lanai, and views of golfcourse
The Golf Villas at Mauna Lani E3Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Promotion Announcement: Complete your reservation and leave a review between May 1 and December 31 to...
Luxury 3BR Kona Dreams w/ Ocean Views, Private Pool, Central AC & Prime Location
Welcome to Kona Dreams by Gather, a charming three-bedroom, two-and-a-half-bathroom home in the heart of Kailua-Kona, Hawaii. This family-friendly retreat promises an unforgettable getaway, offering breathtaking ocean vistas and a private oasis in an upscale...
New - Hawaiian Tin Shack
Escape to paradise at the Hawaiian Tin Shack, a cozy-luxe retreat in the Big Island jungle. Just 40 minutes from Volcanoes National Park and 20 minutes to Hilo, this 3-bedroom, 2-bathroom home sleeps 8 and features a private hot tub, fully stocked kitchen, and a...
Plantation Cottage: Lavish Fairway Oasis w/ Pool/Spa, AC, and Gorgeous Sunsets!
Island living at its finest! Experience charming plantation-style living in this gorgeous Poipu home located on the first hole of the Kiahuna Golf Course. Enjoy all the Robert Trent Jones, Jr. community has to offer - Shopping, golf, and beach amenities boast around...
Princeville Private 3 bed 2 bath w/AC
This private end of road cul-de-sac home has everything you need! It’s steps away from Princeville’s community center with fine dining, night life, shops, treats, and groceries. While central, this home is a personal hideaway with a private back yard backed up to...
New! Sans Souci 1004 1B/1B/1P Stunning unit w/ Ocean front view
Sans Souci, located on the southeastern coast of Oahu, Hawaii, is a captivating coastal paradise on Kaimana Beach, near Colony surf condominium, Zoo, Waikiki Beach. Enjoy pristine sandy shores, crystal-clear waters, and lush greenery for sunbathing, swimming, and...
Best Deal! Boogie Boards, Snorkel Gear, Baby Gear, Golf! Its all in the deal!
Call for our Introductory Special Pricing! New! Luxury 2BR, 2 BA ground floor villa with sophisticated tropical décor and direct beach access!Kolea, located just 30 minutes north of Kona-Kailua at Waikoloa Beach Resort between the Hilton Waikoloa Hotel and the Marriott...
Seahorse Luxury Suite at Seaspray Ocean View
A private oasis across from the desirable Kahaluʻu Beach Park. This two bedroom luxury suite is bright & airy with a private lanai & your own KOI pond. A private guest only pool deck includes a barbecue and dining area for outside entertainment. The living room is a...
First Class Luxury Beach Front Resort Condominium
Located in the World-Famous Ko Olina Resort and Marina on the 2nd of four lagoons, you’ll enjoy the mile and a half walkway along the four lagoons as you pass the newest 4 Seasons in Hawaii, the Disney Aulani Hotel & Spa, the Marriot Ko Olina Beach Club and us, The Ko...