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.
Pili Mai 14D, 3 Bdrm, 3 Bath, AC, main floor
Luxury Condo. Main floor, one level condo. 3 bedroom, 3 Bath, Sleeps 8. Central A/C. Granite countertops, bamboo and travertine flooring, stainless steel appliances. Surrounded by the Kiahuna Golf Course, with views of the mountains. Central Poipu location. Walking...
Elegant Giant Oceanfront Estate - steps to Magic Beach with pool, sub zero
Gorgeous and high end 4 bedroom plus bonus (sleeping) loft, located in prime gated community, sleeps 12. Very large landscaped yard, fantastic ocean view, central A/C, plunge pool, top appliances (sub zero) granite kitchen beautiful bedrooms, fabulous artwork and only a...
Top Floor, On Golf Course, Large Lanai with Views!
Welcome to your peaceful Waikoloa retreat - a relaxing top-floor condo w/ golf course views & resort-style amenities:• Sleeps 4 | 2 bedrooms | 3 beds | 2 baths• Community amenities includes: Heated saltwater pool, hot tub, fitness center• Private lanai w/ outdoor...
FABULOUS OCEAN VIEW, 6th FLOOR CONDO, “149-5 STAR REVIEWS”
Located at the Honua Kai Resort in the Konea Tower. Our studio has a fabulous 6th floor ocean view on Kaanapali Beach. This spacious 6th floor studio is an elegant place for a total Maui experience. Our studio/condo features:• luxurious king bed and a sofa queen...
Prime Oceanfront Kona Reef Vacation Condo - D Building
Location, Location, Location - Oceanfront - D Building.Direct View through Towering Palms into Kailua Bay.Watch the Dolphins, Whales, Parasailers, Surfers and Beautiful Hawaiian Sunsets from your Oceanfront Lanai.Listen to the soothing sounds of the ocean and feel the...
Luxurious home on resort grounds with lanai, grill, pools, hot tub - near beach
Mauna Lani Maluhia #420Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Luxury plus paradise equals this gorgeous home, tucked onto lush grounds at the KaMilo at Mauna Lani resort...
LUXURIOUS ~ 1 bdrm • 2 bath • Sleeps 4 ~ BEAUTIFULLY DECORATED OCEAN FRONT CONDO
Paradise inside and out! The elegant B314 is an elevator ride up to the third floor of the Maui Sunset, where you'll enjoy breathtaking ocean views right outside your window. The warm Hawaiian shore nestles directly against the Maui Sunset greenbelt, with beautiful...
Maui Oceanfront Condo, Mana Kai 811, Amazing Views, on Sandy Beach
Here it is - the Hawaiian Ali'i oceanfront getaway that puts a check mark next to everything on your vacation wish list. Looking for luxury? Want to hear the ocean waves from your condo? Breathtaking views of the coastline and islands? A mile of the best sandy beach on...
KoOlina Luxury Vacation in Paradise!
We invite you to experience Paradise at the KoOlina Resort on the Island of Oahu. This beautifully appointed townhome is located in the Coconut Plantation on the 10th tee of the Championship KoOlina Golf Club. We are just steps from the Ocean Pool which features a sand...
3 BR 2.5 Bath Home on Incredible Anini Beach
Located on Kauai's verdant North Shore, Anini is a haven for the traveler who wants to experience the unspoiled natural beauty of Hawaii. Protected by a large outer reef, the quiet waters of Anini are perfect for swimming, snorkeling, fishing, kayaking, windsurfing, and...
Turtle Bay Villas 206
Please Note: Access to resort amenities is not included, however, the condo complex has its own pool, grills and is just steps to the beach!Prepare to settle into island time a little easier with the unparalleled accommodations and amenities that await you at Turtle Bay...
Kolea 9B offers a nice tropical view and easy access to the Kolea Beach Club!
Kolea 9B has been newly redecorated and offers a beautiful tropical view of the ocean, mountains and palm trees. It has easy access to the Kolea Beach Club. From the moment you walk into this two bedroom extended floor plan villa you will notice the openness and views...
Kolea - Stay with Us and Save! the Best Rates in Kolea!
Call for our Introductory Special Pricing This Luxury Property… This unit is a luxurious, new, airy, light-filled 3-BR, 2 BA ground floor end-unit villa with sophisticated tropical Asian decor, lots of windows, and all the high-tech amenities a person could possibly...
Ocean Views - G201 - Steps From The Beach!
Brought to you by Abita Luxury Rentals.Now with Mauna Lani Sports Club and Mauna Lani Beach Club Access!Enjoy stunning ocean and Maui views from this second-floor, one-bedroom, two-bath condo in the exclusive Mauna Lani Terrace (C floor plan). Thoughtfully upgraded and...
14D Panoramic ocean view, beautiful sunset every night. Best in Ekahi!
Wailea Ekahi #14D is an Ocean View condominium in Wailea Ekahi's acclaimed Lower Village. There are amazing panoramic ocean views from this condominium home! You will feel like you are on top of the world as you look out from the second floor onto the Greenbelt and over...
KKSR#7303 Remodeled Top Floor Unit With Loft, Golf Course Views
Welcome to Keauhou Kona Surf & Racquet Club #7-303!This Gorgeous top floor unit truly is special, a lot of custom features one can enjoy. This spacious premium unit has an impressive 1,384 interior square feet, featuring 3 bedrooms & 2 bathrooms. The property has...
Modern 2BR/2BA w-A/C, Sleeps 6, Walk to Beach, Spacious, Prime B Bldg Location
Absolute Serenity awaits you in Maui, Hawaii. This air-conditioned, two-story, fully-equipped condo, sleeps six and has plenty of space for your family, plus hotel-style amenities that include access to two swimming pools, hot tubs, and tennis courts. Our recently...
BREATHTAKING GOLF COURSE VIEWS, HOME "B", MODERN-CLEAN-NEW, UNWIND IN PARADISE!
Welcome to Hillside Perfection on the Greens at Golf Ridge Homes!Discover your ideal fully furnished, 5 bedroom, 4.5 bath, 2 car enclosed garage, air conditioned executive home located in central Honolulu. Perfect for savvy business travelers and visiting construction...
Oceanfront luxury steps from the beach with pool, hot tub, balcony & central AC
Waipouli Beach Resort H202Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Say hello to Waipouli Beach Resort H202, your very own sliver of island paradise in the heart of all the...
Nestled in Unbeatable Location, offering a rare Combination of Comfort & Beauty
Nestled in an unbeatable location adjacent to the world-renowned 1 Hotel Hanalei Bay, Hanalei Bay Villa #1 offers a rare combination of comfort, convenience, and natural beauty. The sunset proximity to our Villa is highly sought after, some saying the sunsets are the...
Beachfront Unobstructed Ocean View, 3rd Floor End Unit, AC, Wi-Fi, Streaming TVs
ALOHA. Come vacation in our beautiful, newly remodeled 2BR/2BA beachfront home. Enjoy the breathtaking views of Kaho’olawe Island, Molokini Crater, the West Maui Mountains and of course the pristine Pacific Ocean and its shoreline. Sugar Beach is the longest sandy...
Your Tropical Kona Retreat - Breezy Condo Steps from Beach
The perfect blend of comfort and convenience. Shaded by palm trees and on the second floor, the light breeze keeps the temperature perfect. The one bedroom/one bathroom unit features a fully stocked kitchen, private lanai with garden view, and a dedicated parking spot....
Luxurious Kolea Penthouse with direct access to Anaehoʻomalu Beach.
Located in the acclaimed Kolea community, one of the most sought-after oceanfront developments on the island, Hale Mermaid penthouse is a spacious 2 bedroom, 2 bath luxury penthouse with partial views of Anaeho’omalu Bay. It is an 'end-unit' which allows light and...
6 mins from Nat'l Park! Enjoy the sound of rain & birds in a peaceful retreat.
Hawaii State Tax ID: 148-388-6592-01. Hawai'i County IDs: STVR 19-345557, NUC 19-293Aloha! E komo mai. Welcome to Fern Cottage. Located across from Volcano Village, and just minutes from Hawaii Volcanoes National Park, we invite you to make our fully permitted house...
Tropical Paradise Retreat in Princeville! Full Kitchen, Swimming Pool!
Hanalei Bay Resort is a 22-acre piece of tropical paradise overlooking the stunning Hanalei Bay on the North Shore of Kauai. Vacationers enjoy a private beach, a state-of-the-art pool area, and an onsite bar and restaurant. Spacious one and two-bedroom condos feature...
May Last Minute Special! Amazing Ka'anapali location-Ocean Views-Cold AC
‘Anuenue Hideaway’ at Maui Eldorado – Unit K2041 Bedroom | 2 Bathrooms | Ocean Views | Steps from Ka’anapali Beach | Great PoolsWelcome to Anuenue Hideaway — your private escape in the heart of Ka’anapali Beach Resort. This beautifully appointed 1-bedroom,...
Wai'ula'ula C101 - Exceptional Oceanview Residence
This exceptional corner, ground-level, oceanview residence offers a great room with sliding glass pocket doors for indoor/outdoor island living, a chefs' kitchen outfitted with stainless steel gas range/appliances, a master suite and secondary suite with Tempur-Pedic...
🌴 Gorgeous Oceanfront Luxury Retreat 🌊 Pool, black sand beach, AC and billiards
We are THE perfect luxury listing on the east side of the Big Island! A quick distance to black sand beaches, waterfalls, the volcano and charming Hilo town. ALOHA! Welcome to Hale Kakahi or Hawaiian for “unique, outstanding, one-of-a-kind house” -a perfect name for...
Beautiful Private Cottage
Spectacular private entire home 2 bedroom cottage, brand new construction in 2017, located on the "sunny side" of Kamuela/Waimea town. 12 minutes from world renown white sand beaches and resorts of Kohala's Gold coast. Also closely located within minutes from...
Chic & Elegant Oceanfront Vistas
Summary:Welcome to Paradise! Our completely remodeled studio condo at Kauhale Makai Village by the Sea awaits. Completely renovated and outfitted in December 2021. Experience our waterfront condo with fabulous ocean views located in sunny Kihei. Beach chairs, umbrellas,...
Hale Naia By Parrish Kauai - oceanfront views
Enjoy the best of island life at one of Poipu’s finest Kauai oceanfront rentals. The 2 bedroom, 2 bathroom coastline gem is in a prime location for family or friends who love to live by the water. Its design takes full advantage of the million dollar setting with...
Beach House - Steps from Beach. 3 bedroom/3 bath. Private yard, pool, hot tub
Welcome to the Poipu Beach House. IG @poipubeachhouse. A beautiful 1920s-era plantation home steps from Poipu Beach. This home is a historical gem that takes you back to old Hawaii with original wood floors, lava rock footings, and 100+ year old dry-stacked lava rock...
Gorgeous Oceanfront H101 Condo-Best Location at Resort!
If you are looking for the absolute best location at Waipouli Beach Resort in Kauai...look no further. This one-of-a-kind ground level beachfront/oceanfront vacation condo is the most sought after property at Waipouli Beach resort! Step off the private lanai of Unit...
Best Hilo Beach Park House. 3,600 sq. ft. Sleeps 16. New at Richardson's Park.
Newly constructed with 5 bedrooms and 5 baths for privacy and comfort. Giant front decks overlooking Richardson's Beach park and large upstairs living room for family time. Vacation Rental Highlights:• Large 3,600 sq. ft. house, 5 bedrooms, 5 baths. Sleeps 16 with day...
Kaanapali Alii | 284
Welcome to Kaanapali Alii 284, a stunning 8th-floor condo that perfectly balances comfort and style, making it an ideal retreat for families and friends. One of the standout features of this residence is the additional sleeping room with sliding privacy doors, providing...
RARE, GATED, PRIVATE BEACHFRONT HOME! PRIVATE POOL, 6 BEDS 6 BATHS
WE ARE A LICENSED MAUI COUNTY VACATION RENTALHAWAII TAX ID #W 24149416-01STRH PERMIT APPROVAL STKM20150004 TMK 390090050000LEGAL VACATION RENTALVERY RARE FIND BEACHFRONT/OCEANFRONT. Beautiful, Custom 6 bedrooms, 6 full bathrooms on Private Gated Road in the heart of...
Spacious 4-bedroom house plus bunk room with WiFi and AC in charming Kailua-Kona
Introducing Akela Ka Hale Kai, affectionately known as Lucky 42 at Kona Bay Estates.Experience unmatched relaxation with our special spring rate beginning at $1649 per night (N++). Delve into a serene seaside retreat, where every aspect is designed with your utmost...
May Sale - Stunning End Unit with Amazing Lanai Views at the Beach Villas Resort
Escape to paradise in this beautifully designed high-floor villa at the exclusive Beach Villas Resort in Ko Olina. Boasting panoramic beach views and a refreshing ocean breeze, this spacious end unit is the perfect retreat for a relaxing Hawaiian getaway.Step inside and...
Beautiful Poipu AC, Walk to Beach, Pool and Tennis KP117
PROPERTY DESCRIPTIONWelcome to Sunny Poipu Beach! This newly remodeled Kiahuna Plantation leaves nothing to be desired! Relax on your private lanai overlooking the garden while being steps to the sand. Surf spots, long walks and lifeguarded beach are at your fingertips....
Remodeled 1bd, stunning sunsets & views
Nestled on the 3rd floor, Valley Isle 305 is a charming 1-bedroom, 1-bathroom condo that offers direct ocean views and ceiling fans throughout. This resort has elevators for easy access. Unit 305 can accommodate up to 4 guests. The master bedroom features a king-size...
NEW Listing: Special Rate - Mauna Kea Fairways South 22 - Dreamy Hawaiian Escape
Special New Listing Rate!Welcome to Mauna Kea Fairways South 22, where elegance meets contemporary comfort in a tranquil setting with breathtaking ocean views. Our *fully remodeled* 3,800sqft vacation rental is designed for peace and luxury, offering a haven for...
Hale Oka Nunu: Oceanfront Private, Spacious Paradise North Shore Home w/ Hot Tub
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Your dreams of staying oceanfront on...
Ocean Views ! Excellent Proximity to Hualalai Resort Amenities ! Includes Golf Cart
Located in the Award Winning Resort Community of Hualalai Four Seasons.Beautiful ocean views from this delightful two bedroom Garden Level Villa. Spacious Lanai with lounge seating extends seamlessly to a large lawn area. Enjoy the sounds of the ocean and glances of the...
Includes Hilton Waikoloa Pool Pass thru June 2025. Halii Kai 10G
This vacation rental is professionally managed by ResorticaHawaiiHalii Kai 10G. Ocean Views!Please scroll down for detailed informationBedding Configuration:Master Bedroom: King BedGuest Bedroom: Queen BedGuest Bedroom: Queen BedHilton Pool Pass: Valid for stays...
Best in American Living Award Winner! Resort Villa, Short Walk to Beach
BEST IN AMERICAN LIVING AWARD WINNER!Welcome to Laule'a 6 at Mauna Lani Resort. Located within a brand new project (2018) which boasts the best of luxury and convenience located at the world-class Mauna Lani Resort on the Big Island of Hawaii. This exclusive community...
Exceptional Oceanfront Luxury Condo - Fully updated, AC, Top Floor, Quiet
Absolute direct oceanfront top floor, two-bedroom condo located in the heart of Kailua-Kona, Hawaii.Step inside and take in stunning ocean views from your private balcony—welcome to paradise!AC in all spaces, fully updated with high-quality furnishings throughout.From...
Sunny Family Oasis ☀ Tree House, Trampoline, Games, Toys
Single family residence with front and back yard. Wonderful trade winds keep the house cool and fresh year round. Relax on either of the front or back lanais. The house is stocked with all the necessities for the best possible stay in Princeville, Kauai. You will have...
Wailea Beach Villas | PH210
Experience the beauty of Maui in the luxurious Penthouse 210 at Wailea Beach Villas, a stunning retreat featuring two bedrooms and two bathrooms designed with tropical island elegance. This vacation rental welcomes families with its spacious layout, offering stylish...
"Coconut Crest Cottage"
"Coconut Crest Cottage" is a perfect tropical getaway for families, small groups, or visitors to BYU-Hawai'i. Nestled in the heart of Oahu's North Shore within convenient proximity to the ocean and the iconic Kahuku Sugar Mill, featuring numerous food trucks. Turtle Bay...
Ocean View Condo at Foster Tower Across from Beach w/Great Amenities
This property requires a minimum 30-day rental. Book with confidence—professionally managed by Ali'i Beach Rentals, an award-winning property management company.Foster Tower located at 2500 Kalakaua Ave on the 14th floor.Welcome to The Foster, perfectly situated in...