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.
Oceanfront Condo - Steps to the beach, amazing views, perfect for whale watching
Oceanfront 1 bedroom, 1 bath, completely renovated condo. Magnificent ocean views, steps to the ocean. Perfect whale watching location from your lanai. Quiet, central Maui location. Easy access to Paia, Lahaina, Kihei, Wailea/Makena. Sugar Beach is 5 minute walk from...
Hale Hui Kai 208 - Ocean View Luxury Condo on the best beach on Maui, Split AC!
Hale Hui Kai is one of Maui's hidden gems sitting directly on the sand on Keawakapu (Kay-Ah-Vah-Kah-Poo) Beach; arguably one of the best beaches on Maui. Hale Hui Kai 208 sits just a few steps from the beach and away from the road offering peaceful views of lush...
Secluded, spacious new geodesic home on the Big Island, Hawaii.
This stunning geodesic luxury 2,000 sq feet home complete with a full range of amenities, rests on 2 private acres enveloped by the lush beauty of the rainforest. Immerse yourself in the serenity of the tropical gardens, where the melodious coquis will gently lull you...
Charming & Updated Maui Banyan 2 Bath
Discover Maui at Maui Banyan H109 apartment, a charming 1-bedroom, 2-bath condo steps from Kamaole Beach Park II. Conveniently on the first floor, it hosts up to 4 guests. Relax on the lanai amidst lush greenery, stroll to the nearby beach for breathtaking views. Stay...
Hana Homestead by the Beach
Hana Homestead is our eco friendly home in the heart of Hana town. The spectacular ocean views, large decks, hot tub and inferred sauna sd well as the modern rustic elegance of this unique home is just the beginning. A three minute stroll will bring you to Hana Bay, and...
BIG ISLAND BLUE MAKAI, Oceanfront 2BR in Puako! Beautiful sunsets in paradise
Blue Makai has a sense of spaciousness on the property with a large yard and shoreline access. Trees just above the water’s edge offer shade for enjoying the sights and sounds, balmy breezes and breathtaking views of the Pacific Ocean. The spaciousness extends indoors...
3 Bed 3 Bath Suite in Sunny Poipu with Modern Stainless Kitchen AC, Pool & Gym
Our Moku Hale, or “Island Home,” is peacefully nestled on the Kiahuna Golf Course with stunning views from each private lanai; the front lanai has a picturesque view of the lush mountains and golf course, while the large back lanai has an expansive view of palm trees...
Family sized condo minutes walk from beach and golf course in Ko Olina Kai.
HOA rules (for ALL residential condos in Ko Olina, not just ours!) restrict rentals to 1x/30 days and Hawaii State Laws requires stays of 30 days or longer.This comfortable and spacious villa can accommodate 6 guests in a gated community with its own private pool. it is...
@ Marbella Lane - 2 master suites | MT+Ocean Views
Summary:Make beautiful memories in this spacious 4 BR home with 2 master suites, located in a gated community with 24 hours security. It is within the greater Waianae area, right in the heart of the Makaha Valley. On the Leeward side of Hawaii where the Ocean Trade...
Welcome back to Maui, Gorgeous Ground Floor 2bed2bath, wrap around lanai K139
Aloha and welcome to Maui,Gorgeous large 2 BR/2BA condo on the first floor* Very convenient* steps to the pool* Konea 139**Beautiful tile floors**We have a collection of beautiful Honua Kai condos in both towers. We have several one bedroom, 2 bedroom and 3 bedroom...
Spacious remodeled town home, beach access,quiet prime location in Princeville
Private town home set in the in quiet prime location. Beach access is private with fabulous views and easy walking . truly the best beach access in Princeville area. Close to all favorite beaches.The bonus is we are 2 minutes from Princeville town center (grocery, shop...
AS SEEN ON HGTV BEACH HUNTERS! Oceanfront, Amazing Whale Watching and Snorkeling
Welcome to Koni Kai, Hawaiian translation: Passionate Sea. Koni Kai is a beautifully designed, very comfortable oceanfront home. Considerable time and effort has been spent to ensure Koni Kai is equipped with everything one might want/need while on vacation. Koni Kai is...
KONA REEF D-36 AMAZING TOP FLOOR DIRECT OCEANFRONT PENTHOUSE, AIR CONDITIONING!
Welcome to The Seashore Oasis, a Magnificent Oceanfront Top Floor Condo - Come Enjoy Paradise! Condo is newly redecorated in a stunning matching volcano and beautiful sunset theme! From our direct oceanfront top floor condo, you can enjoy the close-up sights and sounds...
Enchanting oceanfront condo with pool, lanai, and washer/dryer - golfing nearby
Kona Riviera Villa #104Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Aloha and welcome to a perfect Hawaiian getaway on The Big Island! When you're not playing along the white...
THE BEST KEPT Secret ON MAUI!!! Little PEACE OF Paradise
OUR LITTLE PIECE OF PARADISE-NO ELEVATORS OR SHARED SPACE SO VERY SAFEThis beautiful one bedroom, one bath condo is like home away from home. The warm tropical décor immediately puts you in the 'Maui Mood'. It is located in the heart of Kihei, away from traffic noise,...
Island Oasis Near Kaanapali Beach & Black Rock
A slice of paradise awaits at this West Maui vacation rental in Maui Eldorado Resort! This 2-bedroom, 2-bath Kaanapali condo has an authentic Hawaiian theme with easy access to Ka’anapali Beach and Black Rock, making it the perfect place to create unforgettable...
Includes Beach Gear. Bay Club 622 Waikoloa
This vacation rental is professionally managed by ResorticaHawaiiBay Club at Waikoloa 622Please scroll down for detailed informationBedding Configuration:Master Bedroom: King BedGuest Bedroom: King BedAmenities:Beach Equipment: All of our vacation rentals include beach...
Gorgeous full ocean view! Short walk to beach! FREE Parking & Wi-Fi! Sleeps 6
Waikiki Park Heights #2101 – 2440 Kuhio Ave.(30-Night Minimum. ALL MONTHLY RESERVATIONS ARE SUBJECT TO APPROVAL.)Soak in the gorgeous full ocean view from this stunning 3-bedroom/1-bath condo in the heart of Waikiki! Located an easy 5–10-minute stroll from the best...
Royal Mauian Oceanfront, Fabulous View!nMay Specials!
After a long trip to get to Maui, it is wonderful to walk into the condo and be wowed by the view. You are right on the ocean. On the 2nd floor, you are looking directly at the water. I think everyone heads to the lanai immediately. Unpacking can wait. You can enjoy the...
Beautiful, newly remodeled ground floor unit at Kiahuna Plantation
This condominium has one of the best locations at Kiahuna Plantation in beautiful Koloa, Kauai. It is a ground floor unit with no stairs. It is considered to be a “garden paradise” view. It overlooks the twin bridges with fabulous landscaping. Birds of paradise,...
Kona Bubbles: Pristine Luxury 4 bedroom Home with Amazing Pool & Oceanviews!
'Kona Bubbles' is a gorgeous home in gated Meilani View Estates with ocean views just above Kailua Kona. Recently finished in 2016, this custom built 4 bed, 4.5 bath home offers almost 3000 sq. ft. of roomy interior space including a detached guest suite/ garage combo &...
Penthouse oceanfront views of the jewel blue Pacific, whales, stunning sunsets
Sixth floor, 2bedroom / 2 bath oceanfront unit with extra large lanai with patio dining table, 4 chairs and two loungers, well equipped gourmet kitchen with skylight. Comfortable, deluxe furnishings throughout the unit with HD Cable flat screens in the living room and...
Just another day in Paradise!
The Palms at Wailea #1305 is a beautiful 2 bedroom 2 bath air conditioned condo located on Maui's sunny, southwest shore. From the lanai, you have a spectacular ocean view to the west, the impressive Haleakala volcano to the east with and incredible, colorful gardens...
Davidson Point Beach House: 4BR Oceanfront Kekaha Estate
TVRNC-1099E Komo Mai, Welcome to Davidson Point Beach House!Experience the peace and tranquility of this oceanfront estate size lot offering privacy and a front row seat to the surfers at Davidson's Surf Break. Enjoy views of the island of Ni'ihau in the distance and...
CROWN JEWEL PENTHOUSE D406! UNFORGETABLE OCEAN VIEWS!
UNIT D406: THE CROWN JEWEL PENTHOUSE AT WAIPOULI BEACH RESORTIf location and view are important to you while spending your vacation time at Waipouli Beach Resort, it doesn’t get any better than this….Unit D406 is a Top Floor Penthouse perched in the CENTER of the...
Beautiful Ekahi13F! Spectacular views, easy access to pools and the beach!
Our privately-owned, 1 bedroom 2 bath, second level condo has been renovated and updated with custom built-ins and new electronics, appliances and AC units. It is situated on the upper floor of building 13, on the quiet green belt leading down to the main pool and...
Lae Nani 514 is Closest to the Beach. Walk Out Your Door a Few Steps, You are at the Ocean!
Summary:Closest to the beach, walk out your door, a few steps you are at the water.The Space:Feels like home but ON THE BEACH !!! Listen to the sounds of the surf and enjoy sunrise AND sunsets from the lanai.This ground floor condo has easy beach access, while being set...
Oceanfront home on one of the most popular beaches in Kauai!
Centrally located fully equipped oceanfront beach cottage. This is Hawaii at its best!Our home is fully stocked for fun with board games, body boards, beach toys. We also provide free beach towels, chairs, umbrella, cooler. FREE airport shuttle, wifi, A/C each room,...
Hale Kahakai | Ko Olina | Beach Villa w/ Pool!
Summary:Welcome to Hale Kahakai in Ko Olina! Nestled between exotic gardens and shimmering koi ponds, this charming paradise beckons vacationers looking for a secluded tropical escape. Maximum occupancy strictly enforced in accordance with local ordinances.The...
Sale!! Gorgeous 3BR 2BA Villa in Wailea, With Ocean and Sunset Views
Location and views are everything when it comes to this home. Only a short walk to some of the most beautiful beaches in the world. Nestled in the heart of Wailea, most would consider to be the most beautiful and prestigious area of Maui. This RARE 3 bedroom villa has...
Captain's Quarters Cottage on Kamuela's Nob Hill
Enjoy the cool setting of Kamuela. Located in the famed hub of Parker Ranch the beloved central point of verdant cattle country rich in Island history. Located on one of the hillsides above Kamuela town, this Cozy Chateau style cottage sits near the top of the hill...
Includes Hilton Pool Pass for thru June 2025. Waikoloa Colony Villas 2705
This vacation rental is professionally managed by ResorticaHawaiiWaikoloa Colony Villas 2705Please scroll down for detailed informationPLEASE NOTE: There is ongoing construction in the adjacent resort area nearby Building 27. Work generally occurs 7:30am-3pm...
Elegant 1937 Home Steps Away from Black Sand Beaches
LAST MINUTE opening - December 31, 2025 to January 3, 2026. Early check-in and late check-out available. 10% discount off quote.Hale Keaukaha is a majestic and elegant 1937 home perfectly situated across from Hilo’s Richardson’s Beach Park, a wonderful small black sand...
Maui Resort Rentals: Honua Kai Konea 415 - 4th Floor Studio w/ Gorgeous Ocean Views!
Peace and tranquility await your arrival at Konea 415. One of the absolute best studios on offer at Honua Kai, this luxurious gem provides gorgeous ocean views from its 4th-floor vantage point as well as shelter from the prevailing trade winds. Its peaceful location in...
Luana 3C - Luxurious 3BR/3BA Villa with Private BBQ & Lanai at Honua Kai Resort
Indulge in island luxury at Luana Garden Villas, the newest addition to the stunning Honua Kai Resort. Get ready to be amazed by these spacious 3 bedroom villas nestled in 3 private enclaves, featuring large lanai's, private outdoor kitchens, and a personal garage for...
Ocean Views! Newly Remodeled in 2023! Kumulani D2.
This vacation rental is professionally managed by ResorticaHawaiiKumulani D2. Ocean Views!Bedding Configuration:Master Bedroom: King BedGuest Bedroom: Queen BedDen: Fold Out Queen Murphy BedMauna Kea Amenity Program: see all details belowPLEASE NOTE: The Mauna Kea Hotel...
Amazing ocean and sunset views! Near beaches. gorgeous pool & spa. It’s the one!
Beautiful ocean and sunset views! Enjoy this relaxing condo in a private gated community. This 2 bedroom, 2 bath condo has everything you may need or want: a fully equipped kitchen, resort style beds and bedding, and very comfortable furniture in the living area and on...
Best Island location between beaches & Waimea. GH
This charming and spacious Garden Hale Apartment is situated on a lush two acres on the sunny side of Waimea (Kamuela)Our peaceful retreat is the perfect location for exploring the numerous points of interest on the Big Island and a private getaway to relax and...
Private Guest Home / Stunning Location / Walk To Poipu Beach/ New AC and W/D
Welcome to Hololani! In the Hawaiian language, it means 'gone to heaven' which is how you will feel when you spend your Kauai vacation here in this cozy hideaway. Fabulous Poipu Beach 1 king bedroom unit on ground floor of newer home. Access to 2 lanais and private...
Hale Kamaole 318 Third floor condo, easy access to best beach on Maui!
Hale Kamaole #318 is a spacious 2 bedroom, 2 bath partial ocean view unit on the third floor. It boasts a fully-equipped kitchen, washer and dryer, free Wifi, and phone service with long distance calling to the US mainland and Canada. There are ceiling fans throughout,...
Banyan Bungalow is nestled in the jungle and surrounded by a gorgeous landscape.
Treat yourself to a gorgeous natural setting with a magical banyan tree while still being close to amenities. Nestled in the jungle and surrounded by greenery, our comfortable bungalow offers a queen bed, small kitchen, private entry, large lanai, and fun outdoor...
Kamilo 321: 3 BR Mauna Lani Resort Home with Private Pool
Kamilo 321 is the most spectacular of the homes built at Kamilo. The beautiful model home of the Hoku A floor plan offers 2,100 sq. ft of interior living space and 550 sq. ft. of covered outdoor lanai space with every upgrade imagined by the developer. This single-story...
K L V R Welcomes you to K325, Great Ocean Views from all bedrooms & living room,
Aloha and welcome to Maui! Konea #325 is among the very finest 3 bedroom condos in the entire resort. This Third floor condo offers sweeping majestic views over the manicured resort grounds and pools to Ka'anapali Beach. The magnificent vistas extend over the beach and...
Maui Resort Rentals: Honua Kai Konea 614 - Large 6th Floor 1BR w/ West Maui Mountain Views!
Konea 614 is a luxurious one-bedroom mountain view suite that enjoys expansive vistas of the West Maui Mountains. The suite is ideally suited to take advantage of some of the most beautiful sunrises anywhere. Coupled with frequent afternoon rainbows, you will cherish...
❤️PiH❤️ ELEGANT ESCAPE ★ Heated Private Pool & Spa ★ Detached Ohana Suite ★
Brought to you by Paradise in Hawaii Luxury HomesWelcome to Elegant Escape at the Residences of Laule'a at Mauna Lani, part of our Hawaiian Luxury Collection. Elegant Escape has private pool and spa with stunning ocean, golf and Mauna Kea views. Enjoy sunsets on the...
Sunset vista condo with WiFi, central ac, lanai, w/d, onsite pool/spa
Pili Mai 15KOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Immerse yourself in tropical reverie at this stunning Poipu condo. Located in the Pili Mai community, you'll be...
Wailea Ekahi 51F Oceanview - Walk to Beach
Our spacious Wailea Ekahi 1 bedroom, 2 bath condominium is fully appointed and includes phone, radio, high speed wi-fi internet connection, color TVs with DVD and cable, private laundry center and personal touches for your enjoyment and convenience.There is a fully...
OCEANFRONT, remodeled, 2bd/2ba Penthouse - Sands of Kahana 281
Oceanfront Sands of Kahana Resort- beautiful, remodeled oceanfront view - 2 bedroom, 2 bathroom Penthouse with 2 additional sleeper sofasOceanfront pool and second poolRestaurant and BBQ areasFitness CenterTennisACWalking distance to restaurants and storesMagnificent...
Beautiful Ocean View/Steps to beach/Washer & Dryer in unit
There are only a select few units at Kiahuna Plantation that offer the location, convenience and a full panoramic ocean view like Kiahuna 17 beach house. We are located in building 4.Make your next vacation a lasting memory of brilliant sunsets, manicured lawns, and...
Hale Mana Kai Poipu, Kauai
Aloha! Hale Mana Kai is warm and welcoming, designed so you can relax and enjoy the beauty of our island.The large Master Suite with ocean view, is furnished with a king size bed, cable television, desk, comfy chairs, walk in closet, double sink, open shower and large...