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.
🌴Hotel Room w/in beautiful Oceanfront Condo.🌸
You will enjoy easy access to everything from this centrally located place. This 3rd floor room is a part of Kauai Kailani Condo's with an ocean view from your room. Enjoy the coastal breeze or use the air conditioner. The room is equipped with a microwave, mini-fridge,...
Newly Remodeled 3 Bed/2 Bath Ocean and Mountain Views
Our condo, (unit 402) is family owned and operated and new to the rental pool. This beautiful and spacious 3 bedroom beach front condo offers stunning ocean and sweeping white water views from the living room, kitchen and master bedroom. In October 2019 the condo was...
*OCEANFRONT *EXCLUSIVELY UPGRADED 1 BED 1 BATH
The Royal Mauian 208 is a stunning fully remodeled and oceanfront condo. This one bedroom apartment is bright and airy equipped with spacious living area offering a queen sleeper sofa as an additional sleeping arrangement. You will enjoy magnificent, OCEANFRONT views...
❤️Best Views on Maui! Perfect for Honeymooners!!❤️
*** NO RESORT FEES OR PARKING FEES! ****** Our condo is Unit 1013, located in The Lanai Building at The Mahana. We recently had our roof replaced in the summer of 2024, so there will be no construction work in our building this year. This year’s roof replacement...
Waipouli Beach Resort Gorgeous Luxury Ocean View & Pool View AC!
Gorgeous Oceanview 2 Bedroom, 3 Bathroom Condo at First Class Waipouli Beachfront Resort & Spa on Beautiful Kauai.There is Central AC in this condo as well as a full-size washer and dryer for laundry!This exceptionally, well decorated 2 Bedroom, 3 Bath third floor Condo...
Enjoy a Piece of Paradise with Ocean View, Whale Watching, Snorkeling and More!
Check with the State of Hawaii for the latests rules and requirements prior to your trip. ************************************************* We know you will enjoy your stay here! Maui Kamaole A115 is well-appointed and fully-equipped ground floor condo located in one of...
Magic Sands Oceanfront! Sleeps 18, 6-bedroom house in charming Kailua-Kona!
Stay comfortably in Kailua-Kona at this delightful 6-bedroom house; across the street from one of the Big Island's top destinations-Magic Sands Beach! With 4 king beds, 1 bunk bed, 2 queen beds, and 2 sofa beds, there's plenty of space for all guests. Cool off in the...
PERFECT LOCATION BEACH FRONTnINQUIRE special discounts reduced rates for march
Experience Haleiwa like a local in this delightful 1-bedroom apartment. Relax in the cozy living room or unwind in the jetted bathtub after a day of exploring. The bedroom features a comfortable king bed for a brilliant night's sleep. With amenities like a washing...
Paradise at Alaeloa - Swim with the Turtles!
Welcome to Alaeloa where you will instantly feel at peace. Total relaxation and privacy are a given. Your island home is part of a gated low-key community that Sunset Magazine has referred to as the "Pebble Beach of The Pacific". The home has just gone through a remodel...
3 x Ocean View 2 Double Beds at Outrigger Kona Resort and Spa
Your adventure to the Kona Coast starts at this oceanfront Big Island property, just steps away from the sun, sand, and surf. Guests will enjoy spectacular dining options, including a waterfront restaurant and poolside bar. The on-site spa and fitness center offer a...
HALE HALE'AI OCEANFRONT AIR CONDITIONED SPECTACULAR with POOL
Exceptional Oceanfront Vacation rental. The home has been totally renovated, everything including furnishings are top of the line, Central Spit AIR CONDITIONED , with private POOL. Here is Hawaii Island at its best. Sit on your lanai and watch the waves, whales in the...
Aloha Paradise! Remodeled Condo with New A/C & Full Ocean View!
This freshly updated, single-level condo has everything you'll need to stay comfortably in the heart of Kailua-Kona and enjoy the Island’s many activities. It features all-new air conditioning throughout the condo, a modern chef's kitchen with dishwasher and plenty of...
OCEANFRONT, Stunning Corner Unit in Boutique Complex, Spacious, Pool, A/C!
Right-on-the-ocean, newly renovated, upscale and spacious condo in a gated boutique complex. Top floor (second floor) large 700 sq foot corner unit with nobody above you. Unbelievable views from the lanai and living room. Windows everywhere that will make you feel like...
Maka Nui Estate: Private Family Resort Style Home
Maka Nui Estate: Luxurious Oceanfront Paradise in Captain Cook, Hawaii.Aloha and Welcome to Maka Nui where big views meet unforgettable moments!Perched on a dramatic cliffside at 1,000 feet elevation, Maka Nui Estate, meaning Big View, offers sweeping vistas of...
NEW! Luxury Plantation Home on Kiahuna Golf Course
About this spaceThis gorgeous Hawaiian Plantation Style home designed by a local architect, resides on the 8th fairway of Kiahuna Golf Course with views of Haupu Mountain.Spectacular Gourmet Kitchen , chefs will enjoy !Poipu features many beaches to indulge in surfing ,...
Wailea Elua 803 - Ocean Views, Modern Renovation, Central AC, Wi-Fi, BBQ Grill
Every detail was addressed in the complete and total renovation of this single-level luxury condo at Wailea Elua Village. Upon entering Wailea Elua Village unit 803, you are immediately greeted with panoramic ocean views from the open living area, and the unit is...
Marriott Ko Olina Beach Club: 1bd full kitchen
This is a Marriott Vacation Club property. Multiple rooms can be booked for same dates. If your dates aren’t available in same room layout and view for entire stay it may be available if you are okay with moving rooms within the resort. Room tax is extra at approx...
North Shore Garden Hideaway
This is a newly renovated 2 bedroom apartment on a large gated lot in a very secluded neighborhood on the North Shore. It is a 3 minute drive from the property to the famous world class beaches and surfing. The apartment has 2 bedrooms, full kitchen and large bathroom...
Mana Kai 310 - Beautiful Ocean Front Condo at the Mana Kai
Welcome to Mana Kai 310 ... Where you can have your toes on the beach in 60 seconds. Your captivating relaxed Hawaiian vacation starts here! The ocean is your front door!This 767 foot spacious condo has two king beds plus a sofa bed and two full bathrooms. It...
*UNINTERRUPTED 180° OCEANFRONT AND PRISTINE Remodel
** PLEASE NOTE THE FOLLOWING DATES: -Sugar Beach Resort pool will be closed from SEPT 8th - SEPT 24th for annual maintenance-Sugar Beach Resort BBQ area will be closed starting July 1st, for 3-4 weeksThe impressive Sugar Beach Resort is a beachfront high-rise luxury...
Four Bedroom Oceanfront Condo with Amazing Sunsets!
Welcome to our Kona Beach Home at Hale Kai O’Kona! A Spectacular Ocean front home located on the incredible Western Shores of the beautiful Big Island. Our Vacation home has been completely remodeled from top to bottom. It is close to everything (Town, shops, beach,...
Oceanfront 1-BR Condo in Waianae w/ Sunset Views
Escape to this oceanfront 1-bedroom condo at Hawaiian Princess Makaha in Waianae. Ideal for couples seeking a romantic Hawaiian getaway, the unit features breathtaking views of the Pacific, modern amenities, and direct beach access. Relax on your private lanai or...
Relaxing home away from home- honeymoon friendly
The view of the ocean and coastal pasture makes guests exclaim "wow" as they enter the dutch doors of this cozy cottage. This is a place to relax. You can watch the whales play and hear them sing at night. The cows lazily graze through the pasture below with the Big...
Luxurious spacious zen oasis: pool, AC, beach gear, bikes, kid equipment
A heartfelt welcome to our Casa Aloha, our 4-bedroom, 2.5-bath oasis, our happy place. We set up our upscale spacious, tranquil, sun-lit 4-bedroom condo (3 full-size bedrooms + a converted den with doors, windows, a sleeper sofa, and a fold-away bed) with 3 expansive...
Right on the BEACH!! Luxury Penthouse 100% Oceanfront, On the Beach Sleeps 2
Aloha & Welcome~ ~Sit on your private Lanai & watch the Whales during whale season...'Totally OCEANFRONT Penthouse Suite. Planning your honeymoon? Anniversary or that special event in your life? Then you have found the perfect place on the 12th floor. The Mahana is...
Wailea Elua Village | 905
Wailea Elua 905 is a vacation rental situated in the picturesque beach locale of Maui. This spacious three-bedroom, two-bathroom condo offers a perfect blend of comfort and luxury, making it an ideal retreat for families or friends traveling together. This condo is...
Private Cottage In The Rain Forest TA065882726401
Cozy, private rain forest retreat cottage situated above Kona in the Kaloko Mauka Honua'ula Forest Reserve. Located on a 3-acre property, this cottage is set away in a lush forest of Ohia trees and Hapu'u tree ferns. Enjoy the sweet aroma of ginger surrounding this one...
Beautiful Maui Condo Steps from the Beach in Kihei!
Live like a local during your stay at Kihei Bay Vista unit D110!This ground floor unit features a large lanai overlooking the tropical green lawn, mere moments from the sparkling shore!Our private oasis provides you a home away from home with a king sized bed, full...
Palm Maui County permit STPH 20130018
Maui North Shore Oceanfront Cottage 2 bedroom oceanfront cottage, sleeps 4, one rental group at a time. Relax in this charming bungalow or under the palm trees. Enjoy the surf or the nearby swimming beach or watch the turtles swimming. Minutes from world famous Ho'okipa...
Contemporary Luxury condo minutes from Hanalei Bay & other stunning beaches.
**If you are effected by the devastating fires in Maui please let us know*****Security cameras are located outside above the front door and above the sliding door on the lower level lanai. Both cameras do not look into private spaces.**The North Shore of Kauai is one of...
Rocky Point Hale Luxury Oceanfront Vacation Home in Haleiwa
The Rocky Point Hale is a quintessential North Shore custom built luxury home located at the peak of the famous Rocky Point surf break. The home is situated in a private setting on the point out of view of ocean goers and public beach accesses, yet its location allows...
Quaint COTTAGE ~ Walk To Coffee shop, nearby Road to Hana & Haleakala
We invite you to stay in our quaint and nicely decorated Haiku Surf Cottage on the North shore of Maui. IMPORTANT!!! Beware of scammers advertising our home on CL. Only available to rent from Amy - the real owner. SUMMARY: Walk out the back gate to the coffee cafe or...
2 Bed 2 BA with Full Direct Views of Bali Hai and Hanalei Bay! This is Paradise!
From the moment you walk into 4221/4222 and see Bali Hai and Hanalei Bay directly in front of you, you will know you are in paradise. Enjoy the sunsets from the slate covered lanai and hear the waves of Hanalei Bay below. This 2 bedroom, 2 bath, recently remodeled condo...
Poipu Sands 116 - Ground-Floor Condo with Pool & Hot Tub Access, Steps from Stunning Beaches
POIPU SANDS 116 AT KOLOA KAI VACATION RENTALSA Tropical Retreat with Stunning Ocean ViewsWelcome to Poipu Sands 116, a spacious 1,353-square-foot ground-floor condo nestled on the sunny south shore of Kauai. Featuring breathtaking ocean views, easy access to Shipwreck...
Mango Sunsets: Gorgeous Oceanview Estate w/Private Pool, Spa & AC
We invite you to sit back, relax and experience the dazzling sunsets, tropical breezes and never ending ocean views from "Mango Sunsets", our private 3-acre Kohala Ranch estate where modern elegance meets traditional quality craftsmanship. This previous popular vacation...
Waikiki Banyan Upscale 1 BR
Aloha from Midway Vacations! Our team of local hospitality experts is dedicated to turning your Hawaiian getaway into a reality. When you stay at one of our properties, you can count on a professionally cleaned and meticulously maintained experience. We're even...
Kanaloa at Kona 3304: Delightful Oceanfront Condo w/ AC, Pool & Spa
Just a stone's throw from Heeia Bay, this private and spacious condo offers the ideal oceanfront setting for your Kona Resort getaway. Complete with huge ocean views, lovely Hawaiian décor, central air conditioning, wireless internet, cable, and a washer and dryer,...
Wow !! What a Great View!!--GREAT REVIEWS !
WOW !! What a GREAT view! We've heard this comment many times from vacation rental guests and friends visiting our Maui condo.Sweeping ocean views greet you as you enter, and are visible from nearly every room. The walk to the beach is less than 4 minutes. When you turn...
Poipu Kai Hale - Oceanfront Elegance at Makahuena Point
Welcome Poipu's Hidden Gem! This amazing home offers 3 bedrooms and 3 bathrooms on the ocean with incredible views of Poipu! Imagine your vacation experience in this gorgeous location with unparalleled and unobstructed 200°+ views. This spacious home consists of a...
New Listing- Impressive 3 Bd+2 Bath Vacation Home at Wailea Grand Champions
Bldg. 16 - Unit #153 - A front-row, ground floor, impeccable 3 Bedroom + 2 Bathroom paradise condominium at the Wailea Grand Champion Villas. This is a prime example of what Wailea Grand Champion Golf Villas has to offer in a 3 bdrm + 2 bath category. Upgraded...
2026 Available Westin Nanea Award winning beach! Breathtaking Sunsets! 1/3-1/10
Currently holding the dates 1/3-1/10/26 The Sentry marks the season-opening event of the 2025 FedExCup Season. The PGA TOUR’s Opening Drive at The Sentry and Sony Open in Hawaii welcomes players looking to get to a strong start in the race. Sentry is being played at...
Oceanfront Island Living at its Finest! Unbeatable Panoramic Ocean Views!
Waikiki Shore #1400 – 2161 Kalia Rd.TRUE direct beachfront unit overlooking the sandy Waikiki shoreline with breathtaking panoramic ocean views! Full kitchen, free Wi-Fi, free parking for 1 vehicle. This 1-bedroom condo's generous 1,188 sqft of interior living space...
Gorgeous Home on Landscaped Acre-2BR/2BA
Welcome to Pua Lani, a gated one acre estate two blocks from the ocean that features resort landscaping and large lawn areas that create a very private and serene setting for your stay. The two story home features 2 bedrooms and 2 baths along with a large high ceilinged...
Oceanfront Studio in Kahana - Pohailani 201
Ocean Front Studio in Kahana. Remodeled and ready for occupancy! This condo is so close to the ocean you can hear and smell the ocean. Whale watch or view the large sea turtles from our lanai. Sleep like a baby on our Westin Heavenly King bed. Got 2 more? We also have a...
Kaanapali Alii | 424
Experience the ultimate tropical escape at Kaanapali Alii 424. In this exquisite two-bedroom plus den ocean view rental at Kaanapali Alii, luxury meets serenity along Maui’s breathtaking coastline. This spacious retreat offers an unparalleled combination of comfort...
Combo Booking: Luana Garden Villas 14D, 15D & 18C at Honua Kai~sleeps 24 guests
Welcome to Luana Garden Villa, where paradise awaits you at Honua Kai Resort & Spa in Kaanapali, Maui. Our luxurious and spacious condos, Luana 14D, Luana 15D and Luana 18C, offer high-end amenities and stylish decor, ensuring comfort and luxury during your stay. Each...
Hilton Pool Pass thru June 2025. Waikoloa Colony Villas 1303
This vacation rental is professionally managed by ResorticaHawaiiGolf Views • 2 King Beds + Sleeper • Pool Access + Hilton Waikoloa Resort Pass🌺 Waikoloa Colony Villas 1303 | 2 Kings + Sleeper | Golf Views + Hilton Pool Pass thru December 31, 2025🌴 Steps from...
Hale Awa'puhi 1-C Oceanfront Luxury 2 BR w/ AC and Private Beach Access
Welcome to Hale Awa'puhi 1-C, an oceanfront gem among one of the most luxurious oceanfront condominiums on Kaua’i in a gated boutique 9-unit property on a private cove. Relish the panoramic ocean views and the soothing sound of surf while relaxing in this modern...
Kihei, Maui - Fully Renovated, A/C, Pool, Tennis, Beach
This condo has been completely remodeled floor to ceiling! - New tile, bathroom, kitchen, appliances, and new furniture & bedding throughout.Condo Includes:- Stackable washer and dryer with complimentary start-up detergent supply- A/C in the living room and bedroom-...
*Remodeled Oceanfront in Waikiki - Ilikai Marina
Welcome to our oceanfront home offering stunning ocean views and Hawaiian sunsets, all within walking distance to the beach. Whether you're seeking adventure, family fun, or relaxation, this is the perfect destination while visiting Oahu. On Friday nights, enjoy...