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.
Affordable Luxury @ $300-370 a Night - Golfer's Paradise!
The Golf Villas at Mauna Lani places you in the midst of this legendary and hallowed land. Imagine gently greeting the day from your lanai - 100% Kona coffee in hand - and gazing out as the early sun rises over Mauna Kea, the tallest mountain in the Hawaiian Islands....
Haupu Hale at Poipu: Luxury Home w/ Golf Course View
Haupu Hale at Poipu offers a luxurious escape in Koloa, Hawaii, where gentle trade winds and the rustle of palm leaves create a serene island retreat. Spanning 2,843 square feet, this beautifully crafted home features four spacious bedrooms and three bathrooms,...
Makena Surf E302 Beachfront Resort - 2 Bedroom Oceanfront Condo
Welcome to Makena Surf E302, an exquisite ocean view vacation condo that perfectly blends antique charm with modern luxury. Spanning 1,038 sq. ft., this stunning third-floor suite features two beautifully appointed bedrooms, ensuring ample space for relaxation. As you...
Don`t miss out on This Amazing Home for your vacation.
This 3 Bedroom, 2 bath, one level (upstairs) home is about 3 miles south of downtown Kona and just up the hill from some of Kona’s most famous beaches and surf spots. The home is located in a safe neighborhood, perched upon the hill where you can see the ocean and hear...
Ko Olina Beach Villas B107: Luxurious Beachfront 3-Bedroom Villa
Welcome to Ko Olina Beach Villa B107 by Gather, a luxurious 3-bedroom, 3-bath beachfront retreat offering 1,478 square feet of stylish living space and the perfect balance of island charm and modern comfort. Located on the ground floor with direct pool access and...
Kona Oceanfront Penthouse Condo: Remodeled, AC, Crashing Waves, Sunsets, Turtles
This desirable air-conditioned oceanfront penthouse unit (with elevator) features spacious open beam ceilings and is only 30 feet from the gentle surf lapping directly below the lanai, where surfers launch into the spectacular blue waves of Banyans Beach, one of Kona’s...
Maui Sunset B123 Beachfront, Ocean View, Ground Floor Families! Pool! 3 Bedrooms
- Tastefully appointed, ground-floor, oceanfront condo. - Breathtaking, unobstructed sunset views!- Manicured park grounds directly accessed from the unit's lanai.- Tropical landscaping and outdoor pool with an activity desk for booking tours.- 3 bedrooms with sleeping...
You'll Love The Ocean Views! 5 Star Hospitality! Hoʻokipa at Wailea Ekolu.
ALOHA!Start your day with coffee and beautiful ocean views from the lanai, and finish the day watching amazing sunsets!Immerse yourself in the warmth of Aloha at Our Maui Condos - Ho'okipa at Wailea Ekolu Village. Discover the true meaning of Hoʻokipa, which means...
Luxury condo at Golf Villas J23, upgraded appliances, soaking tub and BBQ
Relax in paradise at this luxury Golf Villas condo at Mauna Lani. This three-bedroom, two-bath home, has everything one needs on a Hawaiian vacation. Enjoy the grill outside, beach gear in the garage, and stunning golf views from the lanai.Enjoy the open layout of the...
Ocean views and built-in desk in a bright condo
Nani Kai Hale 404 is a 1 bedroom, 2 bathroom condo featuring amenities such as an ocean view, a private lanai, and air-conditioning. Located on the 4th floor, this unit can accommodate up to 4 guests with a King-size bed in the bedroom and a Queen sleeper sofa in the...
Oceanfront Lae Nani #533, A/C throughout Condo!!
Once you enter, you will be greeted by a breath-taking view of the ocean. Our 3rd floor walk up unit is breezy with trade winds and relaxing with soothing ocean sounds. For your comfort, there is AC throughout the condo for those hot summer days. The lush tropical...
Pili Mai 3B: Luxury Condo w/hot tub & pool, near beaches, golf & dining!
Set within Poipu’s sunny south shore, Pili Mai 3B is a rare four-bedroom townhome offering mountain views, a generous 1,850 square feet of living space, and access to resort-style amenities. Overlooking the Kiahuna Golf Course and minutes from Poipu Beach, this upscale...
Spring/Summer Fill in Special 249/nt Updated Designer Condo w/ Ocean Views
Welcome to Grand Champions 79! Located in the lush Wailea resort area, this 1 bedroom/two bath villa has been completely updated with new furnishings, a plush new King sized mattress and a fresh paint job. Once you step inside the professionally designed bottom floor...
Kamaole Sands 2-406 - Luxurious Renovation - Penthouse Ocean Views - Split AC
Undoubtedly one of the premiere units at the highly rated Kamaole Sands Resort, this newly remodeled luxury condo, Kamaole Sands 2-406, features every imaginable upgrade. AC in the living room, views of the ocean fronting Kamaole III Beach, and elegant, comfortable...
Oceanfront in Punaluu, sleep to the sound of waves!
This is the most perfect white sandy beach and welcoming turquoise water on the North Shore and perhaps the whole island of Oahu, where you can snorkel all day protected by the reef. You can float for hours, stand up paddle or kayak. Lounge chairs are provided in the...
Private and Sweet Wailea 1 BD+2 BA Grand Champions Villa
New Furniture! New personal amenities! new soft goods! Unit #54, building 6. An impeccable 1 Bedroom + 2 Bathroom paradise condominium at the Wailea Grand Champion Villas. Wailea Grand Champions Golf Villas is in the heart of the Wailea Resort Community in sunny South...
Location Location Location! Kapalua Ridge Villa 812 - Quam Properties
Welcome to Kapalua Ridge Villa 812, where Hawaiian charm meets modern comfort. This spacious and beautifully appointed condo offers sweeping ocean views from every room and lanai, making it a perfect retreat for your Maui getaway. This two-bedroom condo features...
Villas By The Cove, Villa 1 · Go for an Ocean Swim From a Fun Beach Villa
Villa 1 at Villas By The Cove is an ocean view 1 bedroom Villa Suite located just steps from two of South Maui's most popular white sand beaches. Newly remodeled, and conveniently located, this 600 sq. ft. single story 1 bedroom villa offers ocean views, privacy and...
OCEAN VIEW CONDO|QUIET COMPLEX|WIFI&AC
Kona manager Isle Complex,74 units,library and meeting room with WIFI and on-site manager.This second story condo is second from the end,near ocean front. The lanai gives the visitor a wonderful view not only of the ocean and palm trees but the beautiful garden area and...
Once-In-A-Lifetime Ocean Views From All Rooms! Aloha Galore! Discount for 7-nts!
Aloha and E Komo Mai (welcome)!Our Hale Makai ('Ocean house') is a spectacular home at a great value. A rare corner unit with gorgeous 180 degree ocean views from all rooms and the wrap-around lanai, we invite you to come here, relax and enjoy the aloha that our...
Treetop Studio 2nd floor, corner unit
This studio offers private lanai and kitchenette with sink, full size fridge and microwave. King size bed, and remodeled bathroom with walk-in shower. This is a corner unit and is quiet with no roads nearby. * Ideal for those who want to have breakfast and/or lunch at...
Kauai's North Shore Home Near to Hanalei
Say Aloha to your home away from home on Kauai’s breathtaking north shore! Creating the perfect balance between luxury and comfort, this four bedroom four bathroom custom built home will fulfill all of your Hawaii vacation dreams. Beautifully landscaped flora and fauna...
Includes Hilton Waikoloa Pool Pass for stays for 2025. Waikoloa Beach Villas E4
This vacation rental is professionally managed by ResorticaHawaiWaikoloa Beach Villas E4Please scroll down for detailed informationBedding Configuration:Master Bedroom: King BedGuest Bedroom Upstairs: One Full Size Bed and One Twin BedGuest Bedroom Downstairs: One Queen...
Modern remodeled 2bdrm/1bath Condo/Free Parking on Property/Sleeps 6/Great Views
The best things about this condo: Stunning views from the 14th floor lanai (Mountain and Valley/Ala Wai Canal/Manoa Rainbows), convenient free parking on premises, save money by eating in, clean with modern decor, and within walking distance to all that Waikiki has to...
Private Infinity Edge pool with 180 Degree Unobstructed Ocean View!
Hale Napo’o La is a 3 Bedroom 2 Bath, 1740 sq ft Private home that comfortably accommodates up to six guests. This single level home is located in the beautiful Sunset Ridge area of Waikoloa Village, just minutes away from the local grocery store, restaurants, and golf...
1BR, 2BA! Enjoy fairway, & partial ocean views from your private lanai!
Renovated 1 Bedroom 2 Bathroom! Kick back and relax on your own private lanai and take in wonderful garden, fairway, and partial ocean views. Feel the wonderful trade winds and take in the aroma of the beautiful Plumeria trees and Hawaiian foliage. This spacious...
AMAZING VIEWS!! LARGE BEAUTIFUL HOME WITH PRIVATE POOL OVERLOOKING THE OCEAN!
Beautiful, spacious 2 story home with Private Pool and deck to relax!!! Sleeps 12, this home has one of the most breathtaking views from the large Lanai, with the ocean a stone's throw away to watch whales, dolphins & amazing sunsets! . This vacation home is built for...
Beachfront, Sweeping Ocean Views, A/C, FREE Parking and Wi-Fi, Washlet!
Waikiki Shore #1208 – 2161 Kalia Rd.You'll fall in love with the spectacular ocean view from this beautifully renovated one-bedroom condo (820 sqft) right on the beach in Waikiki! Just imagine stepping right from the building onto world famous Waikiki Beach! Then, after...
Stunning Oceanfront Condo
My condo is finally open beginning Oct 15, 2020. Enjoy Endless Ocean views and views of the neighboring island of Molokai from this Ocean Front Condo. There are many renovations and upgrades throughout this unit. The kitchen has been remodeled with beautiful new...
Beautiful Ground floor condo near pool
Our unit, C111, has large folding glass doors which open to extend the 1600-square foot luxury villa to the lanai, where you can enjoy beautiful tropical views of the pool and gardens of the resort, lounge outdoors from the comfort of the living room. The Villa is...
Champion Ridge Home: Luxe w/ Private Pool,Spa,AC & Ocean/Mountain View
Set within the prestigious Champion Ridge enclave at Mauna Lani Resort, Champion Ridge Home by Gather is a luxurious single-level retreat designed for seamless indoor/outdoor living. With four ensuite bedrooms, elegant island architecture, and an expansive half-acre of...
Beautiful Palms at Wailea Condo!
Escape to paradise at The Palms at Wailea Hotel & Resort! Our Mediterranean-style condo rental is nestled on a hillside, offering breathtaking views from the 2 porches! This unit accommodates up to 4 guests, complete with access to a community pool, hot tub, and...
Kihei Maui Beach house - On the water
Update: The Maui county council had approved the ban on short term condo rentals, effective 12/31/2030. There may have been some concern that this would cover rental properties like ours. It does not. Hopefully this provides some clarity if you have been following this...
Oceanfront studio-Fully renovated! 016-552-7552-01
Picture falling asleep to the sound of the surf and waking to a view of the island of Molokai from the comfort of your king sized bed. The spacious lanai provides the perfect spot for a romantic dinner or a sunset cocktail. Unlike many Maui condos, our unit is fully...
Spacious Home with Pool near Queens Bath
Centrally located in Princeville, this house has all the amenities one could wish for a fantastic stay! This is a new home built in 2022, with thoughtful consideration of accommodating guests. Every single thing in the home is new, from the bedding to the dishware! We...
Artistic Top-Floor Tropical Penthouse – Steps to Maui’s Best Beach
If you're searching for a truly unique and comfortable Maui getaway, this artistic top-floor condo has it all! Recently remodeled and thoughtfully designed, this condo now features a brand-new kitchen and an advanced central split A/C system, providing climate control...
KBR #408 - 1 Bedroom/ 1 Bath Unobstructed Ocean Front unit on Sugar Beach!
Paradise awaits Kihei Beach Resort 408Look no further, beautiful custom upgrades throughout, oceanfront condo directly on Sugar Beach, the longest stretch of sand Maui has to offer and just steps from your door. Start your morning off relaxing on the lanai listening to...
LOOK! Spacious Home in the Heart of Hilo - Bonus Rec Room!
Welcome to Hale Ulu Kealoha - "The House of Growing Love"In the historic town of Hilo, Hawaii on the east side of the island where tourists mingle with locals and really experience the 'Spirit of Aloha', we welcome you to stay in our home to enjoy Hilo and surrounding...
Pali Ke Kua #222 - Breathtaking Ocean Views!
Pali Ke Kua #222, PrincevilleIdeally located above the edge of the striking ocean bluffs of Princeville, Pali Ke Kua #222 has all of the features you could want in your island getaway with the benefit of stunning ocean views.You will be mesmerized by the amazing...
Garden Apartment w/ Hot Tub on Historic Homestead
This hidden gem, nestled amongst lush greenery in Paauilo Mauka, offers a peaceful refuge during your Big Island adventures. Our two-bedroom, garden apartment is situated on the ground level of the historic Main House at Keolamauloa Homestead. With a private entrance, a...
Exceptional Historic Home in South Kona
The very best place to gather as a family where social distancing is easy with your own gourmet kitchen and private pool! We have adopted expanded and more thorough cleaning procedures due to Covid 19.Experience Old Hawaii but with all the modern comforts you desire....
View, Value, Comfort, Clean, Gracious Host Available To Assist You In Planning
🌺 Enjoy the spirit of Aloha in this private setting with a fruit orchard and gorgeous ornamental and edible gardens accompanied by a magnificent view of the ocean and the nearby island of Maui. There are only two units on the property, therefore, you have privacy and...
BEAUTIFULLY REMODELED-GROUND FLOOR CONVENIENCE-AC-WELL EQUIPPED
Book with confidence, this newly updated 1 bedroom, 2 bathroom condo located at Maui Kamaole. This condo is managed by PMI Maui, a local Real Estate Brokerage that specializes in vacation rentals. We are located within a mile of the resort and available 24/7. This condo...
KRL B303 Relaxing 2BD on Golf Course w Pool AC
Kaanapali Royal B303 Escape to Maui! 2Bedroom Golf Course Condo with Pool-Close to the Beach FREE daily activities included with your stay value up to $570! Complimentary admission, every day of your stay*: Whale Watch (seasonal), Dinner Sunset Sail, Snorkel Sail,...
March 2025 & Beyond ~ Oceanfront Surfside #313
Thank you for taking a look at our VRBO Surfside #313 property. Luxury and comfort best describe this immaculate oceanfront Kihei Surfside unit, a wonderful and very popular 1-bedroom, one & one-half ( 1.5) bath unit on the third floor of the Surfside. The centerpiece...
Seaside Kona Condo/Top Fl, Sunsets, Private Lanai,Best Kona Location, Sleeps 2
Oceanfront, Surfside, top floor, corner, one bedroom condo for two with gorgeous ocean views and access to sandy Honl's Beach(popular sunbathing, surfing spot immediately next to Kona Reef Resort). Feel the ocean breezes with our extra side windows and extra privacy....
Honeymooner's Delight, Private Pool & Property,Ocean Views, close to beach.
Maui County Permit Number BBKM2014/0004, TA-113-220-6080-01We believe in the Malama Hawaii program where visitors are respected as Ohana "family" and they in turn respect the aina (place) and it's people as Ohana. The MauiJOY 1Bedroom/1Bathroom Guest Suite is very...
KONA ALII 306 OCEANFRONT CONDO, 1 BDRM 2 BTH, AMAZING VIEW IN THE HEART OF KONA
Breathtaking oceanfront view from the most desirable condo building in the heart of Kailua-Kona Village. Air conditioning new in August 2025. This third floor 1 bedroom 2 bath corner unit is beautiful in every detail. We bought this remodeled condo in 2017 and have...
HO'OLEI #24-3-BEAUTIFULLY APPOINTED VILLA-SLEEPS 10-METICULOUS CLEANING
Book With Confidence This Luxurious 3 Bedroom, 3.5 Bathroom (2619 sq. ft) Villa That Provides Everything That You Need To Have A Great Vacation. The House Offers Tremendous Vacation Experience With It's Amenities, Location, And Level Of Finishes. It Is Managed By PMI...
Pool View, remodeled, 5min walk to beach, King-bed. Ahuihou till we meet again
View of Pool, Ground Floor Condo, close to beach with AC in living room. Easy walk to some of Mauis BEST beaches. The pool area is located right out side our unit. Kitchen is stocked and has a gas stove and all the things you need to make Just about any meal. Cozy King...