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.
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...
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,...
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
This four bedroom resort home offers privacy and captivating views in a truly peaceful tropical setting. Exquisitely finished, beautifully furnished and set within Champion Ridge at the Mauna Lani Resort, it offers a convenient location with many fabulous amenities only...
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, Princeville ***25% Discounted Rate has been applied through January due to construction in nearby unit.*** Construction is scheduled Monday-Friday from 8am-4pm.Ideally located above the edge of the striking ocean bluffs of Princeville, Pali Ke Kua #222...
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...
Waipouli Beach Resort B104 Ground floor ocean & pool view, 2 bed 3 bath sleeps 8
Location, location!! Ocean and pool views from every room!! One of the best locations in the resort. Ground floor lets the kids play on the grass in front of your condo. 30ft from the pool entrance and 150ft from the restaurant, 30 seconds to the beach. It doesn't get...
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...
Lae Nani 432. Your Enchanting Accommodation in Paradise Awaits!!
Lae Nani 432 is 2-bedroom, 2-bathroom air-conditioned condo and is a perfect tropical getaway for up to 4 guests. This third-floor penthouse condo is located on lush, well-manicured grounds with a heated pool adjacent to the ocean as well as a beach and a protected swim...
Embrace the soothing trade winds & let the ocean breeze carry your worries away
We look forward to welcoming you to the Big Island of Hawaii. The Ocean View Tropical Ranch provides a private vacation retreat with all the comforts of home for visitors and travelers to the Big Island of Hawaii seeking an alternative to the 'resort' atmosphere, where...
Direct OCEANFRONT, Custom Polynesian Design, See WHALES & DOLPHINS, Sunbathing
Welcome to @haleromantik!On the Big Island of Hawaii, we are located at sea level in the last fishing village of quiet, rural Milolii on an ancient lava flow, with lava coastline.Located 33 miles south from Kailua-Kona, we are just a short 63 miles to Volcano National...
Absolute Oceanfront in Hilo! Read our Reviews!
When we moved to Hawai'i in 1989 our journey started in Volcano Village outside of the National Park. In 2000 we moved our karma and love for the 'aina (land) to Honoli'i. When you visit our home we hope you engender the same feelings we have: peace, serenity and the...
Bowman's Big Island Guest House, Lava Tree State Park, Night Market, Beach
The Big Island Guest House is a private two-bedroom home including:-bedroom with a new queen bed-second bedroom with a queen bed-full bathroom-modern kitchen-large covered lanai (deck or porch) with a bbq-beautiful gazebo with tiki torches-covered parkingOur...
Hale Kale: Direct Oceanfront Masterpiece, Modern Spectacular One of a Kind Home
Escape to the tropical beauty of Hawaii's Big Island and immerse yourself in the tranquility of 185 front feet of oceanside paradise as you settle into this 3 bedroom 2 bath classic Hawaiiana home recently (and completely) remodeled still retaining its 1950s style...
House of Paddles, POOL, Ocean close in Keaau, Hawaii, near Hilo
Located in the Kaloli Point sun belt on the East side of the Big Island of Hawai, House of Paddles is within earshot of the Pacific Ocean’s crashing waves. This private tropical oasis is a two-minute walk from the spectacular Puna coastline to watch sea turtles and...
Hale Lani ~ Heavenly Home
Welcome to Hale Lani ~ Heavenly Home, nestled in the serene coastal town of Kahuku. This charming vacation rental offers a perfect blend of comfort and luxury, ideal for families or small groups seeking a tranquil escape. Step inside to discover a thoughtfully designed...
Romantic Cabin on a gated aquaponics farm centrally located for exploring.
The cabin is a very satisfying living space. High ceiling with loft bedroom high end Serta queen sized bed. A fully functional kitchen is also included. It's a very romantic and cozy space especially for couples. You get acces anywhere in the 2 acre property.We are very...
Tradewind Bungalow, in Kailua on Oahu
Attractive, ground floor, 2 bedroom 1 bathroom unit with a separate living room and private entry. Located on the island of O’ahu, you'll find comfort and relaxation here while on vacation. A 6-8 minute walk to the world famous Kailua Beach. The exciting night life of...
Ocean front in Napili perfect for whale watching
Napili Point B41 is a 1 bedroom, 1 bathroom condo featuring amenities such as oceanfront views, a washer/dryer, and air-conditioning. Located on the ground floor, this condo can accommodate up to 4 guests with a King bed in the bedroom and Queen sleeper sofa bed in the...
OCEANFRONT PROP - STEPS FROM THE OCEAN! Kihei Sands Beachfront Condos - A10
Forget snowflakes - Maui's whale season offers a show like no other! Watch humpbacks breach & splash from your lanai, then relax in the warmth of the island with our NEW SEASONAL RATES that make this winter your best yet!You'll love staying in our one-bedroom Condo A10...
PENTHOUSE ACROSS FROM OCEAN
ENJOY THIS BEAUTIFULLY RENOVATED PENTHOUSE ON THE 7TH FLOOR with 2 bedrooms, 2 baths, split zone AC and gorgeous furnishings and fixtures. Kona Alii has a secure foyer with 2 elevators, assigned covered parking, and a great location right in town. The downstairs Primary...
Kulalani 804: Mauna Lani Resort Townhome w/ AC, Shared Community Pools & Jacuzzi
Your Hawaiian getaway begins at Kulalani at Mauna Lani 804, a spacious two-level villa tucked within the celebrated Mauna Lani Resort. With serene garden and golf course views, high-end interiors, and access to exclusive resort amenities, this retreat is designed for...
Charming Country Home Pa Hau'oli Home
You will enjoy this cool and comfortable country cottage that is situated on over an acre of beautifully landscaped and very private yard. It sleeps up to 6 people. The main house has 1 bedroom and a large loft where the kitchen and living room area is. There is a large...
Special Rate! Enjoy Tropical Views across from the Beach
Beautifully Designed Condo! Enjoy Tropical Views! Centrally located in Kihei just 1 block from local surf spot,The Cove. Many World-famous beaches also just moments away include; Kamaole Beach I, II and III and Kalama Park.Enjoy stunning tropical views from your private...
Kamaka Cottage at Volcano- A Rainforest Hideaway
Nestled in the quaint rainforest town of Volcano, this charming cottage rental sits on three acres of Ohia forest and is just 2.5 miles from the entrance of Hawai‘i Volcanoes National Park. It features a retro-modern design and an open floor plan.The Kamaka Cottage is...
The Best Ocean View in Waikoloa Village!!
One Bedroom (immaculate) Condo with breathtaking views of the Pacific Ocean, Maui and Kohala Mountain.Welcome to “Kailana” (Sea and Sun roughly translated from the Hawaiian), our beautifully maintained and tastefully furnished very private happy place, that sits...
Amazing Views of the Bay and Ocean, Steps to Beach
Welcome to our stunning 3-bedroom vacation home in Captain Cook! Nestled just a 2-minute walk from the serene Kealakekua Bay, this property offers the perfect escape for your island getaway. Golfers will appreciate the easy access to the Kona Country Club, just a...
Hale Pola'i - House of Peaceful Night - Licensed with Maui County STPH2014-0006
Attention, the State of Hawaii Transient Accommodation Taxes has been recently increased to 11% for all 2026 reservations. Confirmed reservations will see an invoice adjustment when the new tax law is signed by the Governor.Spacious two story home on 2 acres land...
Just steps to the beach Napili Shores Resort
Experience Serenity at Napili Shores ResortGlimpse of the ocean from the lanai of this 1-bedroom, 1-bath condo (F249) on the second floor of Napili Shores Resort.New sofa beds, both queen and twin in the living have Posturepedic mattresses. The bedroom has a queen...
504 - Beautiful Remodeled Oceanfront Stunning Ocean View WITH A/C!
This fifth floor condo at the Kihei Surfside Resort with A/C 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 progressively remodeled, most recently new porcelain flooring in...
Prime Oceanfront Two Bedroom Two Bathroom Condo with views of Shipwreck Beach
Located in the heart of Poipu Kai, Poipu Sands Condo #524 is a modern two-bedroom and two-bath tropical vacation rental with unobstructed views of Shipwreck Beach. With this kind of view, guests enjoy spending time on the palatial enclosed lanai, complete with lounge...