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.
Ideal home away with pool, ocean views, & fast WiFi
Mahina Surf 103Our 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 good life here in Lahaina and make yourself at home in this island getaway perfect for a small...
Makahuena 10 minute Walk to Poipu Beach
Private, below ground level lanai allows for relaxation on comfortable furnishings. The condominium complex is oceanfront on a rocky coastline. Our premium upgraded unit will fit your party's needs with many fine upgrades and amenities. Two bedrooms and 2 full baths add...
Peek-a-boo Ocean View,1bd1bath AC Condo, closer to downtown Kailua village
Kona Shores#118 is a spectacular ground floor condo at an Oceanfront Condominium Complex. Kona Shores is just a mile to all restaurants, cafes and shopping within Kailua Village. From the oceanfront Pool and BBQ Area you will be able to enjoy the famous Kona Sunsets, as...
Poipu Kai B111: Lovely Gardenview Villa w/Shared Pool, Spa & AC, Near Beaches
Welcome to Villas at Poipu Kai B111 by Gather, a luxurious three-bedroom, three-bath retreat on Kauai’s sunny south shore. Located in the heart of Poipu, this beautifully designed villa offers 1,644 square feet of living space, refined island décor, and modern amenities...
Aloha Condos, Kanaloa at Kona, Condo 2906, Oceanfront, AC
Kanaloa at Kona 2906 is a luxury 1600 square foot oceanfront condo that is built on an ancient lava flow from the Hualalai shield volcano that last erupted over 200 years ago. It has a spectacular west-southwest ocean front facing view. There are 2 full master bedroom...
Luxury Beachfront Remodel ★ 180° Views ★ Epic Sunsets at Luana Kai D203
Luana Kai D203 by KNOWLES MAUILuana Kai D203 is a sophisticated 2 bedroom, 2 bath resort condo that sleeps up to four guests in a prime oceanfront location. Enjoy 1,150 square feet of luxury living space. Take in the spectacular panoramic ocean and outer island vistas...
Maui Resort Rentals: Wailea Elua 2204 − Luxuriously Remodeled 2BR w/ Stunning Ocean Views, New Listing!
Boasting stunning panoramic views of the Pacific Ocean that extend deep into the home's living, kitchen, and dining areas, Wailea Elua 2204 is a luxuriously renovated second-floor villa featuring some of the most spectacular vistas South Maui has to offer. Watch...
Beachfront Resort Gorgeous 2Bd2Ba Oceanview
"Escape to Maui's Warm Aloha and Enjoy Exceptional Savings on Last-Minute Getaways".Oceanfront condo on the third floor with beautiful ocean views! Gorgeous upgraded property. Quiet home listen to the sounds of the seaWelcome to our condo at Kanai A Nalu resort, your...
Step to beach New Quiet Kiahuna Plantation Remodeled 2 bedroom condo with A/C
Kiahuna plantation unit 222 in Building 35.You are very short walk away from a beach, actually 200 steps.On first floor. Poipu beach is very near.Welcome to Kiahuna Plantation on the sunny south shore of Kauai! This newly remodeled 2 bedroom 2 bathroom Kiahuna...
nGreat 1 bedroom with custom murphy bed in LR room, 61 reviews! HOTEL ZONED
Desirable Ground Floor Unit We highly recommend travelers insurance. You never know what can happen and need to cancel!Please send message to owner before entering your credit card, to be sure the unit is available. The Whaler Resort has two 12-story condominium towers...
ENJOY RESORT LIVING 2 Beds/2 Baths Ocean Views
This privately owned unit offers extra amenities you won’t find elsewhere, including a fully equipped kitchen stocked with spices, coffee, teas, cooking oils, and more.The spacious 2 bedroom / 2 bath apartment is located at the oceanfront Royal Sea Cliff Resort on the...
Makena Surf E103 Beachfront Resort - 2 Bedroom Oceanfront Condo
Makena Surf E103 is a stunning 1,510 square foot oceanfront vacation condo that epitomizes luxurious Hawaiian living. This first-floor residence offers an unparalleled indoor/outdoor experience with its innovative design featuring pocket doors that retract to seamlessly...
Shores of Maui 121 | Upgraded Condo, Pool + Lanai!
The very best of Hawaii awaits when you vacation at Shores of Maui 121. This ground floor one bedroom/one bath unit has tile floors throughout and is outfitted with lovely island-style furnishings, including a queen bed and quality sleeper sofa that comfortably allow...
BEAUTIFUL*Partial Ocean View by TOP Swimming Beach
Relax on the king bed in the master bedroom after a long day of snorkeling, hiking or sunbathing on the beach. Ceiling fans keep you cool at night and the TVs in the bedroom and living room keep you entertained after the sun goes down. This bedroom is roomy and...
16P - Permitted penthouse end unit at the Hawaiian Princess - best view on Oahu
Hawaiian Princess 1 bedroom, 1 1/2 bath end unit penthouse. There is no better ocean/beach view on the westside of the island than from the lanai of this 16th floor condo. This condo sits right on the beach. 850 square feet inside the condo, and 400 square feet of lanai...
Kihei Beach 606 - Direct Ocean Front, Breathtaking Top Floor Views, Central AC!
Enjoy unparalleled ocean views from this top floor unit, Kihei Beach Condominium 606. Beautifully remodeled, beach front, and overlooking Maui's longest golden sand beach. Start and end each Maui day with panoramic views that take in the Pacific far beyond the visible...
Beachfront, Stay right on the Beach @ Hale Pau Hana Canada, we love you!
Stay right on the beach and enjoy being on the beach 24hrs a day. Wet sand views from our lanai, the sound of the waves coming ashore is always with you. You never leave the beach when you stay with us. Spectacular beach and ocean views that will make your friends more...
Ocean View 2-bedroom condo with pool and AC in wonderful Kihei
Newly renovated! Appliances, hardwood and tile floor, light fixtures, granite countertop, furniture... all brand new! Within walking distance of downtown Kihei, this gem of a condo is still far enough away that you can relax in peace and quiet with the beach across the...
Maui's Best OCEANFRONT Condo!!! See whales, turtles & sunrises from our lanai!
Aloha and Mahalo for visiting our condo. The Maalaea community is Maui's best kept secret. Our 2nd floor oceanfront condo has been completely updated and modernized for your enjoyment. Upon opening the door you will be greeted with an amazing view of the ocean and feel...
Ocean Pool Hale 3br 2ba Cozy Princeville Home with Private Pool, Hot tub and Ocean Views, Beach Gear
Welcome to the Ocean Pool Hale, an cozy Hawaiian escape in the heart of lush Kauai. This three-bedroom, two-bathroom single-level home is nestled in peaceful Princeville, a community known for its magnificent scenery and world-class golfing. This lovely home features...
Stunning Oceanfront Condo #512: Updated Luxury & Breathtaking Sunset Views!
Stunning, Front Row Ocean and Sunset Views! Updated and all new furnishings in late 2023. Clean, crisp and comfortable, this home has everything you will need to make your Maui vacation one that you will never forget. Fully equipped kitchen, plush beds and many other...
Top Floor Mana Kai, "Ali'i Level", Incredible Views, Fully Air Conditioned
Thank you for your interest in our Top Floor, Ali'i Level, Mana Kai condo. The direct ocean view from our condo as well as the fantastic location on the beach cannot be overstated! The Mana Kai is as good as it gets. Covid 19 Cleaning Info: We know that in order for our...
Maui Resort Rentals: Honua Kai Hokulani 729 - 7th Floor 3BR w/ Ocean Views from Every Room!
This 3BR deluxe oceanview residence offers breathtaking views of the Pacific Ocean and Maui's neighboring island Lanai from its stunning 7th-floor vantage point.The residence affords a perfect opportunity to gather, reconnect, and celebrate. There is ample room to...
Charming, Newly Updated Groundfloor Condo In Beachfront Complex!
***Professionally Cleaned Condo, No-Contact Check-In/Check Out*** Welcome to Kauhale Makai 126, a MODERN, newly renovated oceanfront condo fully equipped with everything you need to feel right at home on vacation. We invite you to stay and enjoy the peaceful and...
My Oceanfront Hawaii Vacation Rental Kailua Kona
My Hawaii Vacation Rental, "Kona Luana", is located 1/2 mile from downtown Kailua-Kona with the nearest sandy beach 2 blocks away. Kona Luana is a unique 3 story condominium. Unit 1 is on the first floor and is not a rental. Unit 2 and Unit 3 are on the 2nd and 3rd...
Princeville Beaches AC Lux Home 4BR 3.5Ba at Queen's Bath + Mountain Views
*****The Heavenly Arch "Ka Piʻo Lani" House – A Luxurious Princeville Retreat** Indulge in refined island living at this **spacious 2,850 sq. ft. villa**, designed for comfort, privacy, and effortless tropical elegance. **Sophisticated Design & Comfort** - **Three...
Maui Resort Rentals: Honua Kai Hokulani 1034 – Expansive Top Floor Corner 2BR w/ Gorgeous Mountain Views!
Perched high above the palms on the top floor of the Honua Kai Resort, Hokulani 1034 is an exceptional corner penthouse that captures sweeping, unobstructed views of the lush West Maui Mountains, complemented by peekaboo glimpses of the sparkling blue Pacific. Due to...
New! 2 bedroom with access to Mauna Lani Beach Club
Aloha and Welcome to Kulalani in Mauna Lani Resort, your home-away from home on the Big Island of Hawaii. Kulalani shares a two-acre world class amenity center with the neighboring KaMilo complex that offers a large lagoon pool, a lap pool, two hot tubs, exercise...
Ma'alaea Surf Unit B2-1 BR Ground Floor Beachfront Condo, AC, Wifi, Pool, TV
Ma'alaea Surf, Unit B2, is a stunning, conveniently located ground floor unit, just steps away from the pool and ocean. This luxurious unit features a fully furnished kitchen, large master suite with king size bed and a queen size sofa bed in the living room. Enjoy the...
D3, BREATHTAKING views from ALL windows!! Private End Unit on Corner of Bluff!
Spectacular, awesome, and stunning are just some of the comments made by guests to describe the views from this totally private corner unit. D3 at Sealodge is located in the building closest to the corner edge of the bluff so you get both ocean and inlet views. With no...
Ocean View Studio at HBR, A/C Included
Don't miss this very special condo hotel room at the beautiful Hanalei Bay Resort! This unit sits in a unique private location with breathtaking views of Hanalei Bay, mountains, waterfalls and Bali Hai. It is one of the ONLY units at the resort with NO stairs, yet...
🏖️1 Bdrm PLUS bonus room | Great Ocean View | vrKCV
vrKCV - Kona Pacific A306, Professionally Managed by Kona Coast VacationsWelcome to Kona Pacific A306Experience island living at Kona Pacific A306, a 1-bedroom plus bonus room, 2-bathroom condo with a very nice ocean view. Located in the heart of Kona, this beautifully...
Stunning Ocean /Mountain Views in Luxury Million$ Homes w/ Ping Pong, Air Hockey
Feel the warmth of the Ohana spirit as you gather with family and friends in this stunning and yet affordable 4-bedroom, 2.5-bathroom paradise, nestled in the prestigious Mauna Olu Estates—“Cottages of Mauna Olu.” With breathtaking 360-degree views that stretch from the...
5 Bedroom Open Plan with Ocean Views, Queens Bath, Bali Hai, and Golf Course
https://www.youtube.com/watch?v=t2empvqbOT4Whale Hale is a spacious 5 bedroom, 4.5 bath home proudly perched on the bluff above Queens Bath in Princeville, Kauai' where you can see and hear the ocean. From the grand entry staircase to the family friendly living rooms...
Diamond Head Beach - Large Studio - Queen Bed, Balcony, Ocean View, Ocean Access
Privately owned Studio on 8th Floor with large Private Balcony, comfy Queen bed, Ocean and Mountain Views, Kitchenette, Fast Wifi, Elevator, Oceanside Shower, Non-smoking.Aloha!This charming, newly remodelled studio condo in the "Diamond Head Beach Hotel" is perfectly...
KKSR#6201 OCEAN VIEW, 2ND FLOOR, CORNER UNIT, INCREDIBLE UNIT!
Welcome to the Listing Page of Keauhou Kona Surf & Racquet Club #6-201!This spectacular 2nd floor, highly desirable corner unit has an impressive 1,188 interior square feet featuring 2 bedrooms & 2 bathrooms. The property is uniquely positioned in the development and...
Prince Kuhio, Sunny South Shore Condo is steps away from the beach
3rd floor unit, done with a soft tropical touch. Adjacent to historic Prince Kuhio Park, with good ocean views, it's a walk across the street to ocean for snorkeling and surfing. Common sights include Sea Turtles, endangered Monk Seals, and Seasonal Whales. Nicely...
New A/C in 1bd condo featuring tropical views
Papakea E209 is a 1-bedroom, 1-bathroom condo on the second floor with a newly installed split air conditioning system. The condo can accommodate up to 4 guests with the addition of a queen-size sofa bed in the living area. The condo offers dining for 4 and a fully...
505 – Lovely Oceanfront 1/1.5 unit – great ocean view with A/C!
Unit 505 is a fifth floor condo at the Kihei Surfside Resort is on the sought after ocean side of the elevator. It has a spectacular view from the kitchen, living room, dining area and lanai. It has been consistently upgraded by its long term owners. Overall, the unit...
Location, Location, Location
I comply with all Hawaii tax regulations. Hawaii Tax ID#: TA-158-127-3088-01Serenity......This peaceful retreat offers meticulous attention to detail and modern amenities on one acre of oceanfront property facing Mokoli'i Island (familiarly known as Chinaman's Hat) in...
Maui Resort Rentals: Honua Kai Konea 645 - Upgraded 6th Floor Interior 2BR w/ Incredible Ocean Views!
Konea 645 is a luxurious two-bedroom oceanview suite that affords a perfect opportunity to gather, reconnect, and celebrate. This premier location sits high above the palm trees in the closest column to the ocean of south facing two-bedroom suites in the desirable Konea...
Incredible View! Great Location! Awesome High Rise Condo!
This remodeled 27th floor 1 BR condo offers a spectacular panoramic view that spans from Diamond Head to Waikiki Beach to the city lights of Honolulu. It is located in the Waikiki Sunset Resort, which is less than a block and a half to the beach, a 5 minute walk. The...
Wailea Elua Village 2502 - 2 Bedroom Ocean View Condo
Wailea Elua 2502 is a beautifully renovated vacation rental located in the prestigious Wailea region of Maui. This spacious two-bedroom, two-bathroom condo offers stunning ocean views and a serene atmosphere, making it an ideal Hawaiian getaway. The spacious condo spans...
Kona Reef Resort - Absolute Oceanfront Condominium
This fully-furnished oceanfront condominium, is located 23 feet from the water on Alii Drive in Kailua-Kona. We are on the third level of a four level complex, A23. Listen to the ocean waves or catch a beautiful sunset while dining on your private lanai. Enjoy a great...
Hale Haku Home- Unbelievable Ocean Views!
This home has been a vacation rental on VRBO with a 5 star rating for over 7 years. New owner but still has an amazing property manager!Experience paradise in this true Hawaiian styled home with sweeping views of the Pacific Ocean, lush landscaping and amenities. Enjoy...
Cozy Condo With Ocean View |Great Pool | Walk to Punalu'u Beach
Aloha and welcome to your Hawaiian escapeIf you're craving true serenity, come discover Kaʻū—the Big Island’s largest district and its most peaceful. With the smallest population and the richest sense of “Old Hawaii,†Kaʻū invites you to unplug, unwind, and reconnect...
🏖️2 Bdrm PLUS Loft | AC & WIFI | Concierge Included | vrKCV
vrKCV - Fairway Villas Waikoloa G33, Professionally Managed by Kona Coast VacationsWelcome to Fairway Villas Waikoloa G33! Immerse yourself in the spirit of aloha in this beautifully appointed two-bedroom, two-bathroom loft condo with a Hawaiiana theme, nestled within...
Hale Ilikai - Luxury Oceanfront Home on Poipu Coastline
One of the finest oceanfront Kauai vacation homes set on the edge of the spectacular Poipu coastline, this home has ocean and coastline views, central air conditioning, an oceanfront Jacuzzi spa, five bedroom suites and much more. Offering the perfect setting for a...
Two bedroom getaway near Poipu Beach only a 12 min walk With air in bedrooms,
Nestled in the heart of Poipu, this charming 2-bedroom vacation home offers the perfect escape for your Hawaiian getaway. Imagine yourself relaxing by the sparkling outdoor pool, soaking up the sun on the beach loungers, or exploring the nearby Poipu Beach, just a...
Hanalei Dream House - Bikes & A/C included
Just across the street from the iconic Hanalei Bay with its ocean sunset and mountain waterfall views, this large family home is perfect for your Kauai vacation!From the generous lanai complete with gas grill, you’ll be awed by the majestic scenery and tropical...