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.
South Kihei Condo; Steps to Beach!!
Aloha!Enjoy this awesome 2nd floor unit, steps to the beach, shopping and dining, with a partial ocean view from the living room and lanai.The property has 1 pool, barbecue grills located directly outside the unit just downstairs, and beautiful landscaping throughout....
Wyndham Kona Hawaiian Resort
Please note, that some holiday weeks require a seven-night stay, please confirm with an agent. Prime weeks and holiday weeks have higher rates, your agent will send you an initial quote based on the dates you have chosen.Thank you for choosing Dash Realty Group of...
Tropical & Elegant- Sleeps 8- Ocean/Waterfall Views
Ala Hale is a luxurious island retreat with stunning views of the ocean & majestic mountain views. Located on the Makai Golf Course at the 6th hole, within the prestigious resort community of Princeville, Ala Hale's large private pool and spacious lanai's let you...
Newest 2 BR at Maui Eldorado, prime Ocean View
Enjoy your next family getaway in centrally located Kaanapali beach resort area with spacious 1440 square feet plus double length lanais. Ideal for a family up to 6 person, this accommodation offers premium ocean and golf course views and amenities such as shared pool,...
Best 2 Bedroom Condo in Kihei - Paradise Awaits All Year
ALOHA and welcome to our home at Luana Kai. Our unit is set apart from any other by the love we've put into it and the care we've taken to maintain it. Our deluxe condo has tile floors throughout and stainless steel appliances for your use. Although we don't have air...
Charming 1-bedroom condo in downtown Kailua-Kona just 2 blocks from the beach
Welcome to your perfect island getaway in Kailua-Kona! This beautifully updated condo is just 2 blocks from the beach and 1 block from the vibrant restaurants and shops along Ali'i Drive, putting you right in the heart of it all. Inside, you'll find brand new...
OCEANFRONT-HOME FULLY EQUIPPED-FOR FUN AND SLEEPS 10!
Centrally located fully equipped oceanfront beach home. This is Hawaii at its best!Our home is fully stocked for fun with board games, body/surf/paddle boards, beach toys. We also provide free beach towels, chairs, umbrella, cooler. FREE airport shuttle, fast wifi, A/C...
Wailea Ekolu Village 1007 - 2 Bedroom Ocean View Condo
Experience the beauty of Maui at Wailea Ekolu 1007, a stunning two-bedroom, two-bathroom ocean view condo designed for relaxation and comfort. Located along the picturesque Wailea Blue Golf Course, this ground floor vacation rental offers breathtaking views of the lush...
Pam and Glyn's Maui Banyan Retreat in Sunny Kihei. Check Out Our Reviews
PLEASE NOTE: YOU ARE RENTING FROM A PRIVATE OWNER. ALL ACCESS INFORMATION WILL BE SENT TO YOU DIRECTLY FROM THE OWNERS. OUR ONLY ASSOCIATION WITH THE MAUI BANYAN RESERVATION DESK IS FOR THEM TO ISSUE PARKING PASSES AND POOL CODES, THEY DO NOT HAVE ACCESS TO OUR CONDO....
Newly Remodeled, Beautiful Oceanfront Studio!
DISCOUNTED for September, October, November & December 2025Beautiful, newly renovated (Jan 2022) studio just 30' from the ocean. The shower was just renovated Dec 2023.Aloha and welcome to The Maui House 207! When you enter our tropical Hawaiian home you will be...
Wai'nani Waterfall House HEATED Salt Water Pool /Hot Tub BEACH GEAR Games VIEWS!
Welcome to the Wai'nani Waterfall house located in sunny Poipu on the south shore of Kauai. This home has all you and your Ohana are needing for the perfect island getaway. Set in the heart of Kiahuna Plantation Golf course, this new home was designed with families in...
Kaanapali Alii | 171
Welcome to Kaanapali Alii 171, a luxury vacation rental that offers a spacious and inviting atmosphere for families and friends. This stunning residence features a large open floor plan, perfect for entertaining and enjoying indoor-outdoor living. The great room...
Tranquil Keauhou Resort Condo with Ocean View & Resort Amenities
Escape to paradise at Keauhou Resort Condo 139, a charming 1-bedroom retreat in Kailua-Kona, Hawaii. This beautifully updated condo offers a peaceful getaway with no neighbors above or below, ensuring privacy and tranquility. The inviting living room features high open...
Hale Laki – Stunning Resort Condo, Walk to Beach!
Summary:Waikoloa is a picturesque resort area on the Big Island’s western coast, blending natural beauty with modern amenities and making it a sought-after destination for visitors and locals alike.The Space:Perhaps its most defining feature is the stunning coastline,...
Absolutely Stunning Oceanfront Condo!
It’s private and quiet. This is your perfect Hawaiian getaway! Wake up with this stunning view of the Pacific and fall asleep serenaded by the melody of the ocean. While you bask in the sun, enjoy the company of many sea creatures (turtles, dolphins, and whales). All...
2021 Toyota Tacoma with a Rooftop Tent and all the camping gear!
2021 Toyota Tacoma TRD Sport with a Pop up tent! Our camper truck comes with all the amenities! Travel around the lush island of Maui and stay in a different part of the island every night!! Book your adventure today!! We provide everything you need from bedding &...
Excellent for couples or families. Right on the Golf Course.
Our villa provides 2 Bedrooms and 2.5 Baths, totaling over 1400 square feet plus 2 Lanais. It is perfect for families or couples vacationing together. The well-appointed kitchen has beautiful maple cabinetry and granite countertops. Eighteen-foot vaulted ceilings in the...
RELAXING, Away-from-it-All home on the water with small Natural Pool
Hale Pali (Cliff House) is a spectacular (non-smoking) OCEANFRONT home overlooking the blue Pacific. We heartily agree with our guests who have enthusiastically stated: 'there is nothing that compares to actually being on the water' - what better way to enjoy the sound...
Kaanapali Alii | 296
Welcome to Kaanapali Alii 296, your luxury vacation rental in the heart of Maui. This stunning two-bedroom condo offers a perfect blend of comfort and elegance, making it an ideal short-term rental for families and friends alike. Spanning 1,807 square feet, this...
Kukui'ula Villa 8: Oceanview Condo w/AC/Private Lanai, Walk to Shops/Restaurants
Welcome to Kukui’ ula Villa #8 by Elite Pacific, offering a unique charm of Kauai in this luxury Poipu vacation rental condo with expansive ocean views and chic island contemporary décor. Ideally situated within walking distance of the Shops at Kukuiula, Kukui'ula...
Oceanfront Property - 60 feet from the ocean. Beautiful views, free WiFi
***Facility Fees will be waived at the Papakea Resort, beginning July 1st!***Note: The owners own a second unit on the same floor, L-205, so the two can be booked together for larger groups and families. Welcome to Papakea! Located between the Kaanapali and Kapalua...
Stunning Ocean Front Studio! Mahana 803!
STUNNING VIEWS OCEAN FRONT STUDIO MAHANA 803! NORTH KAANAPALI BEACH, A/CWelcome to Mahana 803! Located on the eighth-floor, this oceanfront studio sleeps 2 and features stunning panoramic views of the ocean, beach and outer islands. Living area highlights include tile...
Pili Mai Family Condo 6G, 2 Bedroom, 2 Bath, Plus Loft with Queen Murphy Bed
Two Bedrooms, 1 King bed, 1 queen bed, 1 queen murphy bed, and 1 queen sofa sleeper, 2 bathrooms, nicely upgraded, washer and dryer in unit, lanai, golf course view, great complex amenities.If Sunny Poipu is your vacation choice, 6G at Pili Mai is a great option with 2...
Cozy 1-bedroom with AC and WiFi in enjoyable Kailua-Kona
Welcome to Hale Kai Hideaways, Bungalow A. Vacation at this cute apartment centrally located in the heart of Kona. Alii Garden's open-air marketplace is a five-minute walk, where you will find Shaka's tacos, local coffee & tons of souvenirs. Turtles Beach, a local...
Ocean Front! Includes Waikoloa Golf Membership Benefits. Halii Kai 13A
This vacation rental is professionally managed by ResorticaHawaiiHalii Kai 13A. Includes Waikoloa Gold Golf Membership DiscountsPlease scroll down for detailed informationBedding Configuration:Master Bedroom: King BedGuest Bedroom: King Bed and 1 Twin Fold Out Chair...
Wai'ula'ula M101 - Ground-Level Oceanview Residence
This corner, ground-level, oceanview residence offers a great room with sliding glass pocket doors for indoor/outdoor island living, a chefs' kitchen outfitted with Sub-Zero, Fisher & Paykel and Wolf appliances/gas range, dual master suites with California king beds....
Steps Away From Poipu Beach * A/C * Newly Remodeled * Family Friendly
Remodeled bright, beautiful, breezy top floor, corner unit in Building 23 on Kiahuna Plantation. Located 100 yards from Top 5 Rated Poipu Beach. Fabulous expansive views of gardens, twin bridges and lagoon. A new cal king bed in the master and a new queen sleeper sofa...
Maui Retreat Ekahi 50F, All YOU Need! 5% off for stays over a week!
The rest of JUNE $299 per night!Waiting for you to come and unwind. Just bring yourself, everything else is HERE! Towels, beach chairs, umbrella, boogie board, whatever you need!!!This beautiful second floor unit has an open, beautiful garden/mountain view. The vaulted...
Hapuna Beach Luxury - Private Pool, Maid Service, Resort Access!
Introducing bespoke oceanfront living on one of the most pristine beaches in Hawaii! - C24 at the Hapuna Beach Residences is a luxurious 2-bedroom beachfront condominium with a private pool, adjacent to the Westin Hapuna Beach Hotel and within the Mauna Kea Resort....
Lei Aloha - A Private Retreat, Pool + Fairway Views
Welcome to Lei Aloha, Princeville!This luxurious island home is a 4 bedroom, 4 bathroom home combination of elegance filled with an abundance of amenities. This hidden retreat located in the prestigious resort community of Princeville is one of its kind , and provides...
❤️PiH❤️ Hono Loa ★ Bikes/Beach Toys ★ Private Beach Club ★
Presented by Paradise in Hawaii Luxury HomesWelcome to Hono Loa at the Fairways in Mauna Lani!Hono Loa offers the ultimate backdrop for your Hawaiian getaway. Perfectly designed to accommodate up to 6 guests, it's an inviting, luxurious, and serene retreat for both...
Oceanfront Home with Pool ‘The Cove at Milolii'
Front row views of Kona sunsets Our two-story oceanfront home has views from every room and tropical breeze flowing from roof top cupola through every window and door. The main living area is upstairs with 4 bedrooms and 3 bathrooms, including two master suites one with...
Kona Penthouse 2 Bedroom: Relax and Unwind Aloha Style
Top-floor Kona retreat with stunning ocean views!This 2,000 sq. ft. unit features one king-size and one queen-size bed, hosting up to 4 guests. Perfectly located near downtown Kona's restaurants, shops, and farmers market, tucked in a family-friendly neighborhood. Fully...
Steps to the beach, come share our Maui dream.
Kihei Bay Surf is a cozy 2 story complex of 80 studio condos across the street from the beach. The complex is well kept and clean, with a great pool and jacuzzi area, complete with lounge chairs, 2 barbecues and tables, tennis court, laundry room, and plenty of parking....
Hale Koolau Estate - Private Retreat in Haena with Hot Tub & AC
Hale Koolau Estate (Main House + Treehouse), Haena Permitted Vacation Rental Property - Permit ID: TVNCU #1017 and TVNC #1018Transient vacation rental is located in the tsunami evacuation zoneOn the north shore of Kauai, Hale Koolau Estate sits behind wooden gates and...
OCEAN and POOL View, remodeled 2 bdrm condo with A/C - PAPAKEA K406
Stunning Ocean and pool view Papakea 2 bedroom / 2 bathNewly remodeled throughout & new furnishings2 beautiful swimming pools, 2 ocean side cabanas, jetted spaPool side BBQs3 tennis/pickle ball courts & 2 putting greensWalking distance to stores and restaurantsShuffle...
Maui Kaanapali Villas #A102: At the heart of the Maui Ka’anapali Villas Resort,
Maui Kaanapali Villas #A102: At the heart of the Maui Ka’anapali Villas Resort, a tropical retreat awaits. This ground-floor condo has two bedrooms with en-suites and a half bathroom. The primary bedroom is just off the living area and features a king bed. The second...
Hapuna Beach Residence A32 at Mauna Kea Resort
This extraordinary, oceanfront, family-friendly, third level masterpiece offers floor-to-ceiling sliding window walls that create indoor/outdoor living space, a magnificent chefs' kitchen outfitted with professional-grade Wolf, Sub-Zero and Miele appliances, wine...
Beautiful 2 Bedroom / 2 Bath / Sleeps 6
The beautiful home is located on the east side of Oahu in Hawaii Kai. Located near beaches such as the famous Hanauma Bay, restaurants, shopping centers,hiking trails, scenic lookouts and water sports. The home offers 2 bedrooms (2 queen beds), 1 sofa bed and 2...
3BR condo with A/C, pool & 10min walk to the beach!
RENTAL CARS We also have rental cars available. Please check with us if a rental car is available for your dates. We just recently bought this beautifully decorated, spacious vacation home! Our luxurious 3 bedroom/2.5 bathroom condo is a perfect place to unwind, leave...
Oceanfront - Kanaloa at Kona - Newly Remodeled
OCEANFRONT CONDO - As Kona residents for 25 years, our desire is to share ALOHA. This is your opportunity to Experience Tropical Paradise, spectacular sunsets year-round, spouting whales in winter, and frolicking dolphins. This secluded and prestigious 18 acre Resort is...
Direct Oceanfront 2BD, Kaanapali/Kahana area, FANTASTIC! Home Away from Home!
Maui is outdoor living at its finest! Enjoy having breakfast lunch and dinner on your lanai staring at the ocean! Wake each morning to birds singing, swaying palm trees and the teal blue waters of the ocean.. there is no escaping the absolute OUTSTANDING view from this...
Oceanfront Oasis - Beachfront Condo in paradise at Sugar Beach Resort
Wake up each morning to the sights and sounds of the waves gently hitting the shore as you sit on the private lanai looking at the oceanfront view. Sugar Beach Resort is a beachfront property, no roads to cross to get to the beach, just walk out of your unit and head...
Honu House; Unit 209, Amazing views!! Watch the turtles & whales from lanai!
Honu House, unit 209 is a corner unit, in an oceanfront complex located in Honokowai, just minutes away from downtown Lahaina! This unit does NOT have A/C. Second floor condo with an ocean view and just steps from access to the ocean. The unit is freshly painted through...
It's All About the View! Oceanfront, A/C, Elevator
2026 UPDATE: SPECIAL! The dates of 1/6-1/31/26 have been discounted due to the closing of the pool area for renovations. The SPECIAL rate will be $178.00 + 18.712% + $185 one-time cleaning (approx. 30% discount). The standard nightly rate is $255.00 + 18.712% + $185.00...
Wailea Ekolu Village 1107 - 2 Bedroom Ocean View Condo
Wailea Ekolu 1107 is a charming ground-floor vacation rental that offers the perfect blend of convenience and stunning views of the ocean, mountains, and the island of Lana\'i. Guests can enjoy the soothing sounds of tropical birds without the disturbance of street...
Sweeping Ocean Views - Makena Surf Resort C-106 - Peaceful Ground Level Gem
Makena Surf C-106Nestled within the exclusive Makena community, Makena Surf Resort is a luxurious beachfront retreat offering spectacular views of the Pacific Ocean. This gated property features six carefully designed two- and three-story buildings, each strategically...
Hapuna Beach Residence B22 at Mauna Kea Resort
This spectacular, oceanfront, newly-constructed studio offers floor-to-ceiling sliding window walls that create indoor/outdoor living space, a luxe chefs' kitchen outfitted with professional-grade Wolf, Sub-Zero and Miele appliances, wine storage, plus a dining table...
Get Away to Paradise
COVID Free Quaint 3 bedroom 2 1/2 Bathroom condo located in Ko' olina Fairways. Perfect place to unwind and relax. Two story with 3 bedrooms and two full bathrooms upstairs and kitchen, living room dining room and half bath downstairs. All the comforts of home to...
Romantic 1 Bedroom Home at Anini Beach! - Sleeps 2
Retreat from the cares of the world in this tastefully furnished, one-bedroom, one-bath, oceanfront home.TVR #5082 Punana Aloha, which means 'Love Nest' in Hawaiian, is a one-bedroom, one-bath hideaway on incomparable Anini Beach. Constructed of natural cedar...