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.
Hale Holokai at KAANAPALI VISTA~LUXURY Golf Course Ocean View Home 6 bedroom 3 bathroom~
This is a legally permitted vacation rental according to the County of Maui ordinances.Luxury 6-Bedroom Retreat with Private Pool & Lanai – Steps from Kaʻanapali BeachE komo mai (welcome) to your Hawaiian sanctuary, a luxurious 6-bedroom retreat in the heart of the...
Stunning Views! Luxury Penthouse Kahana Villa E705
Summary:Enjoy your stay in Maui worry-free! Our short-term rental property is unaffected by any proposed legislation that may impact other accommodations. Book with confidence and experience the beauty of our island without any risk of cancellation.Stunning views that...
Kaanapali Alii | 2101
Discover the epitome of a luxury vacation rental in Maui with Kaanapali Alii 2101. Nestled on the stunning western shores of Maui, this 1,500-square-foot condo offers a blend of elegance, comfort, and breathtaking ocean views. Located within the prestigious Kaanapali...
Tropical Wailea Retreat
We invite you to come and stay at our spacious suite where you can enjoy the exclusive Wailea lifestyle. Relax & restore in this serene space surrounded by tropical palms!This bright and airy 1 bed/2 bath, corner end unit is a modern Hawaiian retreat. The suite features...
Breathtaking ocean views!! Steps to the beach!! Recently remodeled!!
Our Hale Kai O Kihei (‘ha-lay-ky o ‘kee-hay) condo offers breathtaking ocean views. On the private lanai, you can enjoy the tranquil sounds of the ocean and view the amazing year-round sunsets. There are also miles of sandy, un-crowded beach directly in front of the...
KAUAI'S Plantation-style Paradise for 2! Peaceful North Shore Cottage 5-STAR!
**THIS RENTAL IS EXCLUSIVE TO VRBO - DO NOT RENT OFF CRAIG'S LIST OR ANY OTHER WEB SITE**If you are looking for the ultimate Kauai experience, then look no further! Located on the North Shore, the most desirable area of Kauai, known for its tropical lushness, sandy...
KLVR welcomes you to Honua Kai Luana upper level 5C Oceanfront Resort, POOL view
Kaanapali Luxury Vacation Rentals (KLVR) Welcomes you to the Beautiful Luana Garden Villa at Honua Kai Resort*5CLuana Garden Villas is the final phase of Honua Kai Resort and Spa, located on the stunning Kaanapali Beach on Maui’s western shores, and steps from...
★ - Rainbow Lookout! Private Hot Tub + Pool Access + New Central Conditioning
Rainbow Honeymoon Lookout at Huelo Point Lookout is the perfect starting point for adventurers embarking on the famous Road to Hana, making it a great jumping-off point for exploring Maui's stunning natural attractions. This hidden gem on Maui's North Shore is an ideal...
Marine Surf Waikiki Studio
Location, location, location! Our elegantly appointed studio is a block from Waikiki Beach, and at the center of shopping, restaurants, and nightlife. We offer FREE parking, high speed WiFi, and a well-equipped kitchen with essentials for cooking. The lanai offers a...
Spacious Ocean View Home. Steps From White Sand Beach. Private pool & spa.
Our home is perfect for a family vacation, romantic getaway or couples retreat!Enjoy our spacious home in the exclusive resort of community of Pauoa Beach. One of 46 homes in the private enclave with access to the private Pauoa Beach Club amenities: * Family friendly...
Affordable, Luxury Resort condo w/ AC @ Kam III Beach
Aloha from Maui.Our beautiful, spacious, Resort Condo is located at Kamaole III Beach Park...one of Maui's finest swimming and snorkeling beaches! The unit is fully equipped with everything you need for a great stay, including a full kitchen, washer/dryer, beach gear,...
Kepharts' Ocean-view Hale: A Home Away from Home
This five-bedroom/three-bath home sits on five acres of land in the Kohala Estates. We specifically designed and built the house as a family vacation gathering spot. Its high ceilings and 760 square feet of windows make it particularly light and airy. Tradewinds and 13...
*TOP FLOOR REMODELED OV 1BR * A204
E Komo Mai “welcome” to Maui Eldorado A204! This newly remodeled tropical condo is located in the heart of Kaanapali, one of the world's most well-known destination resorts with Kaanapali north golf course frontage views and ocean view from your private patio....
Charming Oceanfront retreat- Steps from the Beach, 2BR/2BA Polo Beach Club 308
For those looking for a peaceful, comfortable home base on Maui with true beachfront access. Just steps away, you can enjoy wonderful swimming and snorkeling- no roads to cross, no long walks. From our lanai, you might spot whales in the winter, turtles passing by, and...
Kiahuna Plantation Luxury
STOP! You can go to our owners' website by clicking below on 'CLICK HERE' under links to more information.Why does our unit create such a high rental following? The reasons we keep hearing from past renters...1) Just steps from Poipu's best beach (60+/-, but who's...
Hulili Tropical Fruit Farm- With over 200 five star reviews!
*If your dates aren't available, please check out our new listing #1355789 or our new Treehouse listing #4108089*Opened for guests in 2010, the original HULILI FARM COTTAGE (pronounced who-lee-lee) has welcomed so many wonderful guests that it became time to enable more...
Hale Leilani: Kukui'ula Plantation Villa with Ocean View & Pool
Luxuriously appointed, supremely spacious, and overflowing with tropical charm, this stunning new plantation-inspired home in Kukui'ula is superlative in every way. The entire property—poetically christened Hale Leilani—embodies the most appealing aspects of a...
Ground floor Ocean and pool view at Maalaea Bay
Hono Kai A5 is a ground-floor, 1-bedroom, 1-bathroom condo featuring ocean and pool views, easy access to the property from your lanai, and 1 window A/C unit in the bedroom. Unit A5 can accommodate up to 4 guests. The bedroom is furnished with a king-size bed in the...
2-bedroom cottage, steps from the ocean, AC, parking
Located steps from the ocean, this oceanfront property is the second house on the property in Ewa Beach. This quaint 2-bedroom cottage offers a tremendous escape for guests. With a cozy queen bed, a comfy twin bed, a king bed, and a sofa bed, you'll feel right at home....
Admired Poipu beach house in a perfect location, now a vacation home!
Stay in this beautifully designed vintage Hawaiian style home 350 feet from the Brennecke's Beach side of Poipu Beach park, in the heart of Poipu. Spacious lanais and outdoor living gives everything Kauai has to offer, as well having your private gate leading to the...
Tropical Paradise Getaway Ocean & Lush Tropical Views Pool, BBQ & WI-FI Inn on the Park 1503
Tropical Paradise Getaway Ocean & Lush Tropical Views Pool, BBQ & WI-FI Inn on the Park 1503Enjoy relaxing lanai Ocean, Diamond Head & Tropical views Peaking above the Waikiki Skyline. Clean completely remodeled & newly furnished air conditioned studio suite...
"Happy Daze" at Kapa'a Sands 24 – Unwind on the Stunning Coconut Coast!
Tranquil Shores – Oceanview Escape at Kapaa Sands 24Welcome to Tranquil Shores, a charming 2-bedroom, 1-bath oceanview condo at Kapaa Sands, where peaceful island vibes meet the rhythm of the sea. Nestled along Kauai's Coconut Coast, this multi-level retreat is just...
This Tropical Bungalow features Air Conditioning and Tempurpedic King Bed
Our Home is available and away from the current Kilauea eruption zone. Enjoy your stay here.Between the Scenic Route and the ocean. Good ocean views in an agricultural setting. All NEW furniture and incidentals. Terrific landscaping. Gated with a 2 car enclosed garage....
OCEANFRONT CONDO with STYLE, COMFORT, & AMAZING VIEWS of OCEAN & HALEAKALA
Ocean Views from the Lanai, are so awesome, you may never want to leave the condo! Everyday brings a one-of -a kind Sunrise over Haleakala. Everyday, turtles feed among the gentle waves of our private beach, which is steps away. During whale season watch the Humpback...
ALOHA - Poipu Beach Vacation Condo
Aloha! This charming, cottage-style condo is located at the 35-acre Kiahuna Resort next to Poipu Beach, Kauai's beautiful South Shore. The Resort is beautifully landscaped with rolling lawns, Koi ponds, the famous Moir Gardens, and has its very own world class sandy...
Oceanfront Villa - 3 bedroom with amazing views! APRIL 18-25, 2025
-AMAZING VIEWS from the OCEANFRONT balcony!-Master bedroom with king-sized Westin Heavenly® Bed and HDTV-Master Westin Heavenly® Bath with large shower, vessel tub and double vanity-Guest bedrooms with king-sized Westin Heavenly® Bed and HDTV-Guest Westin Heavenly®...
Paulele Beach House - Charming "Old Hawaii" Home in Hanalei
Paulele is a beautiful Hawaiian-style home right on the closest beach road (Weke Rd.) on breathtaking Hanalei Bay! This tasteful and comfortable home has four bedrooms, five baths, a fully-equipped kitchen, and it comes with everything you’ll need for a wonderful...
Wailea Beach Villas E202 - 3 Bedroom Garden View Villa
Warm breezes and lush tropical gardens greet guests of Wailea Beach Villas E202 as the spacious and comfortably appointed interior blends seamlessly onto the private outdoor lanai. Contemporary neutral and earth-toned furnishings are complimented by splashes of color...
MRR Presents Kaanapali Ali'i 474 - Gorgeously Remodeled 3BR w/ Stunning 7th-Floor Direct Ocean Views!
This gorgeously remodeled 3BR residence boasts a spacious floor plan and direct ocean views from a stunning 7th-floor interior courtyard location. Enjoy over 1800 sq ft of interior living area, an expansive private balcony, and elegant upgrades throughout, including...
Stunning Oceanfront Sunset-Bali Hai Views with A/C + Hideaways Beach below
**2026 Discounted Rates****Book 7 nights or more anytime through June 6, 2026 and receive 10% off your nightly rate**Welcome to Hale Honu Aloha ("Home of Turtle Love") at Puu Poa - An updated spacious two-bedroom, two-bath condo on the ocean bluff of Princeville that...
April Cancellation Reserve ASAP ONLY 179/nt ! 135 Exceptional Reviews!
BEAUTIFUL Unit A308 is an oceanfront condo just steps to the beach! Ocean view offering large and clean accommodations. Enjoy the garden view and all the amenities of the highly acclaimed Maui Sunset resort, including 60 foot freshwater swimming pool beachside and l hot...
Spacious 4 bedroom Home, steps to Hukilau Beach, A/C, 30 Day
This beautiful 4 bedroom home is an easy 3 minute walk to Hukilau Beach.It's in a great location- one block from the beach, close to the LDS Temple , a 3 min drive to the Polynesian Cultural Center and BYU-H. The home has a fully equipped kitchen if you decide to cook...
Romantic Private Garden Cottage B&B Within Walking Distance to the Beach!
Aloha and welcome, We invite you to come and relax in our cottage with a tropical garden and private entrance, as well as a view of Haleakala Mountain. This is a beautiful, resort quality environmentally green built, private cottage. We are a legally licensed with the...
Luxury Zen Polynesian Penthouse & Gold Member Golf Privileges Option
Prepared to be Zenned, Aloha style!!! Penthouse accommodations starting at $260/night (with extended stay discounts available) and on Island coincerge available. State of Hawaii STVR ID #19-375711; and, GE/TA # 069-450-8032-01.Located just 20 minutes north from Kona...
Oceanfront, Top Floor, Two-Bedroom / Updated including split system AC!
Imagine - warm tropical climate, the sounds of the ocean waves washing ashore, palm trees swaying in the breeze, panoramic views, and the perfect accommodations - Is there any other way to experience Hawaii?!This two bedroom, two-bath condominium gives you all of that...
Nihilani 7A. Family Resort Style Living. Central A/C, Pool & Golf
Welcome to your dream vacation destination in Princeville, Kauai! Our two-story, three-bedroom condo offers the perfect blend of luxury, comfort, and convenience. Located minutes from the Makai Golf Course and Hanalei Bay, this property is a golfer's paradise and a...
Remodeled Oceanfront Studio with Incredible View
NEW KING SIZE BED and FULL REMODEL: New flooring, new appliances, new kitchen with granite counter tops, new bathroom with walk in shower, new bedding, and new couch. This sixth floor, spacious Condo is located only feet away from the famous white sands beach of...
Dlx Oceanview Maui Studio...Updated. AC!nSteps to Beaches! Sleeps 4.
Aloha: Welcome to you own Deluxe Oceanview West Maui Studio ...featuring stunning Oceanviews! We are ideally located in West Maui, just north of Kaanapali resort. Our Deluxe Maui Condo rental features Central A/C to stay cool, In-suite Washer/Dryers, Color Cable TV and...
Newly Renovated, Modern Beach 70’s Surfer Vibes
Welcome to the beautiful Kahakai Cliffside - Located on the stunning North Shore of Kauai. Completely renovated in 2023 with dual-zone air conditioning, Kahakai Cliffside sets a new bar for modern-beach 70’s surfer vibes with high-end flourishes throughout. This...
OCEANFRONT RESORT in Koloa-Poipu with AMENITIES INCLUDING WIFI, walk to beach
ALOHA! This 2 bedroom, 2 bathroom condo is located in the beautiful resort called "The Point at Poipu", a family friendly resort.Gorgeous 2 BEDROOM, 2 BATHROOM (King in master and 2 Twins or we can request a Queen for the 2nd bedroom), OCEANFRONT RESORT, short walk to...
Pacific View: 5-Acre Gated West Maui Estate with Pool, Pickleball & Basketball
Pacific View is nestled in the majestic West Maui Mountains, a vast area of lush valleys and cliffs. This lovely 5-acre estate is uniquely situated to capture all of that beautiful West Maui offers.Pacific View is a gated villa offering a generous 4000+ square feet of...
Tropical designer retreat right on the water with ocean view, pool & AC
Puu Poa 101Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Spend your vacation enjoying the salty sea air and ocean views from the spacious lanai and nearly every room inside this...
NEW!! Charming 1-bedroom bungalow in amazing Kona
NEW! NEW! NEW!*professional photos coming soon**Our dream home! Ready to share with you. We have been waiting years to be in this complex! It’s the secret gem in Kona. We put our vision and dreams into a complete remodel September 2024. The kitchen with all new...
Golf Course View Retreat | Wailea Condo GC100 | Walk to Shops & Beaches
*For bookings with arrival dates during November 2025, we will donate money to the Maui Food Bank to feed a family of four this Thanksgiving*Welcome to Grand Champions #100, a meticulously updated 2-bedroom, 2-bathroom villa located in the heart of Wailea. Overlooking...
Brand New 2 Bedroom House
Experience local-style living in the cool, quiet, and tranquil Pupukea. This brand new house is a perfect place to relax.Enjoy a private entrance and free parking. 5 minutes from Waimea Bay and other famous surf spots.Family-friendly, ideal for 4 people with the option...
Spacious Oceanfront Penthouse w/ 180 Degree Views in Kailua-Kona!
Forget your worries in this spacious and serene space. Enjoy being on the ocean in this beautiful remodeled top floor condo unit . Superb coastline and 180 degree ocean views. Recently remodeled, air conditioned, 1,200 sq. ft. 2 bedroom/2 bath condo with bamboo floors....
Cozy Treasure Nestled on a Lush Oceanfront Property - Wailea Elua 1508
Wailea Elua #1508 – Partial Ocean Views & Comfort Near PoolSet within the prestigious Wailea Elua Village, Wailea Elua #1508 offers an ideal balance of peaceful luxury and island convenience. This spacious 2-bedroom, 2-bathroom condo features partial ocean views, a...
Chic Beachy Studio in Waikiki
Beachy style, chic studio renovated to 5-star standard with partial ocean view. Centrally located at Marine Surf Waikiki on 21st floor. Just steps from the beach, world-class shopping, restaurants, and attractions. One block from Royal Hawaiian. Enjoy a sleek place to...
Ultimate Oceanfront Condo with Stunning Views & AC
Unobstructed knockout views! Imagine yourself in this gorgeous location with amazing front row seats, 30 feet to the Pacific Ocean. Whales, turtles and dolphins swim by right out your door! See the stunning sunsets and views of the volcanic Poipu coast all year from...
Makaha Ocean View - 2 bedroom, 1 bath - family friendly
Hawaii License # 031-420-0064-01This property may not be rented for fewer than 30 consecutive days. Rental prices will not be reduced or adjusted based on the number of days the rental is actually used or occupied.ABOUT THIS CONDO: Meticulously clean! This is a...