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.
Explore Kauai & Relax in Luxury - Pool - Grills
Adventure & Luxury Awaits You - Explore the Island of Kauai: Swim, Snorkel, Hike, Surf or Read Under a Shade Tree. Then return to this High-End Luxury Suite with a Resort Pool, Jacuzzi and BBQ grills just steps away. This well appointed suite is Ideal for Special...
Classic Kailua Beach House – Oceanfront Bliss in Windward Oahu
This property is professionally managed by Private Homes Hawaii, LLC and is licensed as a short term vacation rental, 1990/NUC-1780 and is compliant with Hawaii State Legislation (HB2078) for vacation rental accommodations, TA-179-906-2528-01. TMK.Island living at its...
Beautiful - Palms at Wailea 1802
Located in the Kihei/Wailea area, in the world-famous Wailea Resort community, The Palms at Wailea complex boasts a beautiful pool, hot tub and is conveniently located close to the Shops of Wailea, luxury hotels, stylish boutiques, great restaurants, tennis, the Wailea...
Beautiful penthouse suite with stunning ocean view, pool, hot tub & beach access
Sugar Beach Resort PH05Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Treat yourself to the unmatched beauty of Maalaea Bay from Sugar Beach Penthouse 5. You'll be situated mere...
COZY CONDO, JUST STEPS FROM THE OCEAN, LOW DENSITY PROPERTY!
MAUI SANDS SEASIDE IS A SMALL COMPLEX WITH LESS DENSITY FOR THOSE WHO WISH TO PRACTICE SOCIAL DISTANCING OR JUST PREFER TO BE AWAY FROM LARGE CROWDS IN GENERAL. THIS IS A GREAT LOCATION FOR A FAMILY VACATION OR FOR A COUPLE'S RETREAT. THIS IS THE PERFECT LOCATION TO...
❤️PiH❤️ Seashell Villa ★ Bikes ★Free Hilton Resort Passes ★Free Private Beach Club
Brought to you by Paradise in Hawaii Luxury Homes.Welcome to the newest home in our Hawaiian Luxury Collection. Seashell Villa is a wonderful almost new exquisite 3 bedroom home in the gated Kulalani community with high end finishes with pool and recreation center...
Oceanfront Condo with 180-degree penthouse views
Sealodge G9Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Perched atop the oceanfront cliffs in the community of Princeville, this unit offers unbelievable views from every room....
Kona Condo White Sands Village Beach View / Ocean View #215
Stay 70 yards from famous Magic Sands Beach (White Sands Beach). Its Time to come on over and Holo Holo (vacation) with us here in beautiful, sunny, HAWAII. Your unit is located on the Big Island's famous Alii Drive directly a cross the street from Magic Sands Beach...
Modern Ocean View Studio - Waikiki Paradise!
Thoughtfully appointed studio with modern decor. Fully renovated in February 2022! Includes FREE high speed Wi-Fi, cable TV, and various TV apps for streaming services.Check in and out at your convenience with a lock box. Check in after 3pm and check out before 11am....
Poipu Koloa - 2 br unit Ocean/Garden view in Kauai
We can book Ocean Front/OV/Garden view unit if they are available.Price from the system is for Garden View unit. If you like OV, please request it.This is timeshare resort, per policy, unit number floating. Don't know exact unit be assigned until check in, but the view...
Palm-lined condo with easy beach access, pools, hot tubs, & tennis courts
Tropical Oasis at Poipu Kai 514Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Say aloha to your next favorite vacation when you book a stay at this newly remodeled first-floor Poipu...
Private Waterfront House AC & Fast Wi-Fi 30 Day
This house is all about being right on the water. A seawall provides protection from waves at high tide. A North Shore Beach House with the comforts of a nice home ideal for long term stays. Local pickle ball played right down the street. 30 Day Minimum ContractIncluded...
Spectacular Views 1 BR / 1 BA condo in Poipu
A lovely condo overlooking the blue Pacific. Fully equipped and furnished by the owners with much attention to detail. The fully equipped kitchen is both lovely and very convenient for preparing meals and snacks. You will want to visit the local Sunshine Markets for...
TCNC # 1161 All Cedar Home - Breathtaking Hanalei Bay and Mountain Views
TVNC # 1161 Waterfall laced mountains and Hanalei Bay views through a tropical prism. These will be your first impressions and lasting memories of this welcoming home. The Hanalei Vista House is an all cedar home built 15 feet off the ground to enhance the spectacular...
Naia Hale, Spacious A/C home for a relaxing visit
Spacious A/C two-story home, perfect for families and friends to spend quality time together. Have a wonderful family reunion here, come during the holidays for a relaxing visit with loved ones, or celebrate a special occasion at this elegant home. You will create...
BEACH HOUSE on Scenic Makaha Beach with Free High Speed WIFI and Onsite Parking
Working from home? Why??? When you can work from Paradise.Now accepting 30-day reservations. You will find it less crowded, a little unexpected, and truly delightful. The vibe here is RETRO and CHILL, so let the good times roll. Please message us for details as we do...
Pacific Ocean views & newly renovated kitchen
For the same price as a hotel room (i.e. 1 bedroom), you get a home that fits 6 people with beautiful scenic ocean views & a newly renovated kitchen! This bright & airy 3 bedroom, 2 bath home features a large outdoor deck that fits the entire family overlooking the...
Weneki's Island Paradise; Oceanfront complex, Updated, Wi-Fi, Unit 103
Weneki's Island Paradise is an oceanfront complex, ground floor condo with a garden/pool view and just steps from access to the ocean. Located in Honokowai, just 5 minutes from Lahaina. It is a 1 bedroom without A/C, fully furnished with a Cal-King bed, 1 bath with...
🏖️Spacious Property! | Tranquil Location | Concierge Included | vrKCV
vrKCV - Mauna Lani Islands M3, Professionally Managed by Kona Coast VacationsYou and your family will love this townhome for your next Hawaii vacation. Mauna Lani Islands M3 comes fully furnished with all the comforts of home. Come experience resort living at its...
Pali Ke Kua #110 Paradise! Panoramic Ocean and Bali Hai Views!
This beautiful ground floor condo has undergone a COMPLETE REMODEL! The beautiful remodel features Quartzite counters. All new cabinets, Kitchen Aid stainless steel oven and dishwasher, along with a Café refrigerator. Beautiful new tile flooring, all new furniture, and...
Breathtaking Anini home with guesthouse & steps away from beach
Ka Hale Olu at Anini Beach TVNC#4218Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Find a true escape in the luxe comfort of this exclusive property steps away from Anini Beach and...
KAUA'I BEACH RESORT-BEACHFRONT, OCEAN VIEW, POOLSIDE VIEW FROM YOUR LANAI
I fell in love with this heavenly place so deeply , that I decided to buy an apartment here. Newly remodeled September 2025, textured and freshly painted Welcome to my charming Kaua'i home. From the walkway in front of my lanai, which overlooks the pools and has an...
Car Available! 180 degree Ocean Front Unobstructed View. Sleeps 8
OCEAN VIEWS! OCEAN frontage FAMILY GETAWAY!4 bedroom/4 full baths SLEEPS 8Live the true Hawaiian experience of peace, beauty and relaxation. Sleep with the gentle sound of the ocean and cool breeze. This ocean bluff condo offers it all! Why go to Kauai and not stay on...
150-3 Superior Oceanfront Gold Coast Location.
This beautifully appointed 3-bedroom, 2-bath oceanfront unit on Puamana’s “Gold Coast” remains a peaceful retreat amidst the recovery efforts following the Lahaina fire. Located in a tropical oasis at the south end of Lahaina, this luxurious townhome offers the...
Papaikou Escape < 3 Mi to Botanical Garden!
Bask in the paradise of the Big Island at this gorgeous Papaikou home! This 3-bedroom, 2-bath vacation rental features an updated interior, a spacious kitchen, and a location in proximity to captivating beaches and parks. Grab those surfboards and ride the waves of...
Quiet Condo on the Kona Country Club Golf Course
This spacious 1,200 SF 2-BR 2-Bath condo is in a quiet and relaxing spot at the south end of Ali'i Drive. Adjacent to the 8th teebox of the Kona Country Club, it's a beautiful setting whether you're a golfer or not. It sleeps 4 Adults max, and up to 6 total including...
Hidden Island Getaway
Hidden gem awaits your arrival. Newly renovated condo just minutes from one of Oahu’s many beautiful beaches, Makaha Beach. A welcoming family retreat 2 bedroom, 2 full bath, AC and full kitchen facility. Spacious living and dining providing ample space to plan your...
Waterfront Home near Beach. Peaceful Community w/ Swimming Pool and Boat Dock
Experience Oahu like a Kama'aina (local) in this 3 bedroom, 2 1/2 bath waterfront home. Safe community. Views from every room. Private lanai, BBQ grill, community pool, and boat dock. Walk to dining, shopping, bars, farmers market, hiking, beaches. 5 minutes drive to...
KKSR#197 Direct Oceanfront Air Conditioned Townhome, Extended Lanai & Yard
Welcome to this spectacular very popular oceanfront townhome in the heart of historic Keauhou! This 2-bed, 2-bath townhome offers the perfect blend of privacy and convenience sleeping a maximum of 4 guests.Townhome#197 is very unique, you'll notice an extended lanai,...
Spacious Townhome at Mauna Lani Resort - Close to Beach!
This newly renovated 2-bedroom condo at the Mauna Lani Resort is now available for your next vacation. This condominium/townhome is bright and airy and spans two floors with large windows to allow in the natural light. This popular floor plan features a second floor...
Lovely, spacious private estate, 300 ft to Sunset Beach TA#083767910401
30 DAY RENTAL*****A beautiful, peaceful, private north shore estate, 300 ft from sunset beach. The main house has 4 bedrooms and 4 bathrooms and sleeps 8 in beds. You may rent the cottage for an additional 2 people-check availability-it's called the plantation cottage;...
Kihei Kai Nani - 1BR Unit, Just Steps Away From Kamaole Beach!
This 1BR/1BR, 2nd floor corner/end unit features a beautiful garden view and a remodeled tropical interior. The extra windows in the living room and bedroom create openness, ventilation and light. The trade winds and the peaceful garden setting make it one of the best...
MV 1410 2BD Condo w Pool AC Ocean Views Across from Beach
Maui Vista 1410 NEW LISTING Ocean View 2 Bedroom Condo. Perfect Backdrop for Your Hawaiian Vacation FREE daily activities included with your stay value up to $554! Complimentary admission, every day of your stay*: Whale Watching (seasonal), Sunset Dinner Cruise,...
Luxury condo next to Disney Aulani Resort and Marriott's KoOlina Beach Club
Beach front condo on lagoon 2 at Ko Olina shoreline. Only steps away to white sandy beach where you are looking for and enjoy tropical trade winds. Very convenient to almost everything like eat-out, golfing, luau show and even shopping. The unit is large enough for 3...
⛱ Ocean Escape🌴 Your Perfect Spot! Ocean View, Upscale, Clean, Cozy, Prkg, WiFi
Welcome, 'E Komo Mai'CALENDAR IS ALWAYS CURRENT... Please check the availability and if it is full check out our other unit 'Mountain Retreat' VRBO listing https://www.vrbo.com/382565haAloha Hideaway offers a high quality unit at a reasonable price. The Views are...
Maui Family Owned/Managed - Keawakapu Beauty
A mere four minute walk from the lavish Keawakapu beaches will find you in the serenity of our peaceful condominium. Our quiet first floor unit has a partial ocean view where guests can enjoy the vibrant colors of a Maui sunset at the closing of the day on the patio....
Oceanview #202 at Hana Kai Maui - Lofted Studio Upper Floor, Panoramic View!
"Alau” – Unit 202 – is an upper-floor, lofted, ocean-view studio located in Hana Kai’s Mauka Building. The unit accommodates up to 4 guests with 1 queen bed on the main floor and another queen bed in the loft. *Note* SLEEPING IN THE LOFT JUNE THROUGH OCTOBER OS...
Napili Shores E-243 - Upgraded, steps to ocean and pools. Napili Bay - ideal location for vacation
E Komo Mai - Welcome to Napili! Attention to detail in this One Bedroom / One Bath Fully Renovated Condominium with air conditioning. Napili Shores Resort is adjacent to the gorgeous sandy beach of Napili Bay. Not only are the accommodations ideal, you are just steps...
Kihei Beach #404- Serenity by the Shoren
Kihei Beach #404 – One-Bedroom Beachfront Condo with Two BathroomsWelcome to Kihei Beach #404, a one-bedroom, two-bathroom beachfront condo offering panoramic views of the Pacific Ocean and Maui’s neighboring islands. Located in a six-story beachfront property with...
Top Floor! Direct Ocean View! Vaulted Ceilings! Winter Spec! #218
ALOHA AND WELCOME TO HALE KAI # 218 Located right on the ocean on the beautiful island of Maui, our condo can be your _home by the sea_. Comfortably decorated with tropical Hawaiian furniture and artwork, our unit will provide you with all the comforts of home,...
Hilton Pool Pass for 2025 and Golf Discounts. Waikoloa Beach Villas C4
This vacation rental is professionally managed by ResorticaHawaiiWaikoloa Beach Villas C4Please scroll down for detailed informationBedding Configuration:Master Bedroom: King BedGuest Bedroom Upstairs: One Queen BedGuest Bedroom Downstairs: One Queen BedAdditional...
Kahana Village #28 Beach Front Deluxe
Located out on the point at the Kahana Village Resort, our 2 Bedroom 2 Bath condo is 1200 sq feet, completely remodeled and very well appointed. We are just steps from the waters edge and enjoy sunset views in between the island of Lanai & Molokai. Our fully equipped...
Ocean View Escape: Steps to Beach & Free Parking!
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...
Pali Ke Kua 12, Upgraded Hawaiiana Princeville Condo with A/C
Welcome to Pali Ke Kua #12, PrincevillePali Ke Kua #12 is a 2 bedroom/2 bath condo, located in a park-like setting on the tropical grounds of the Pali Ke Kua complex in the residential and prestigious resort community of Princeville.Open the sliding glass doors in the...
Absolute Amazing View, One level, 2 Lanai’s,New bed types King,Queen,Twin Qsofa
Guests are sure to enjoy a memorable vacation in this fully furnished, 2 bedroom/2 bath condo. The master bedroom has a King size bed. The 2nd bedroom is furnished with a Queen size bed and a Twin size bed. There is a Queen pull out sofa sleeper bed in the living room....
Aloha Condos, Na Hale O Keauhou, Townhome J-2, Ocean View, AC
Enjoy expansive ocean and golf course views from both upper and lower lanais and famous Kona sunsets right in front the upper lanai. Designer furnishings, Pacific Rim antiques and tropical décor. Original local artist works. The fully equipped gourmet kitchen will...
Hale Makai at Diamond Head – Oceanfront Estate
We want to inform our valued guests that there is ongoing construction next door to Hale Makai at Diamond Head. This construction is expected to last into 2026. We apologize for any inconvenience and appreciate your understanding in this matter.This Diamond Head...
Peaceful & Elegant Treetop Hideaway in Volcano Village
Set on a quiet street in historic Volcano Village, Hiʻiaka Guesthouse is a private, romantic pied-à-terre on the second floor of a beautiful 2-story custom home. Surrounded by old-growth ʻōhiʻa forest, and overlooking a lush and peaceful garden, the guesthouse...
Kona Ocean View: Beautifully Furnished, Amazing View, White Sands Beach
Great location within the White Sands complex--front building, top floor. Partial ocean view. Steps away from Magic Sands Beach, close to the best snorkeling in the area, and convenient to downtown Kona and area attractions. White Sands complex has all you need with...
Palms 306 Ocean Views, 5 Star Reviews: Remodeled
AMAZING 2 BEDROOM 2 BATH CONDO IN POPULAR PALMS AT WAILEA. SLEEPS UP TO 6 PERSONS. Largest 2 bedroom in areaThis is the largest (1299 sq ft ) two-bedroom ‘C’ plan, built in The famous Palms at Wailea. with vaulted ceilings with huge picture window looking out over...