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.
Oceanfront Napili Shores ~AC~Ocean View
Escape to this fantastic condo in picturesque Lahaina. This cozy retreat features 1 bedroom with a comfortable king bed and an additional living space with a queen bed and a twin bed. Guests can enjoy amenities like WiFi, AC, and a hair dryer. With a convenient location...
Romanna’s Golden Ray Oceanfront Condo, Maui Resort
Welcome to your slice of paradise at Maui Sunset, where you can enjoy partial ocean and stunning garden views from the living room and lanai! Experience the convenience of direct access to the pool, BBQs, and sandy beach, all just steps from your lanai. The beautifully...
3BR Paradise with Direct Ocean Views – Westin Nanea Villas
Indulge in sweeping ocean views with this exceptional three-bedroom, three-bathroom oceanfront villa at Westin Nanea Ocean Villas, perched upon the pristine North Beach of Ka‘anapali. Boasting approximately 1,760 sq ft of indoor living space, this villa is designed to...
Large 3/2 House in Kailua-Kona with ALL New Furnishings and Yard Above Airport
Kona Coastview SubdivisionAs you step inside, you'll discover a spacious layout boasting three cozy bedrooms, each brand new furnishing master bedroom with a comfortable queen-sized bed set and ample closet space for all your belongings. Master bathroom with tub/shower....
Lodge at Kukui'ula Bungalow 3 - 3 Bedroom Bungalow - Platinum
This three-bedroom bungalow at The Lodge at Kukui'ula on Kaua'i offers luxurious accommodations and exclusive access to the award-winning private club facilities and amenities of The Club at Kukui'ula, including the 18-hole Tom Weiskopf designed golf course, sprawling...
Kaanapali Alii Unit 1112
Welcome to Kaanapali Alii Unit 1112, a luxury vacation rental nestled in Maui's exclusive Kaanapali Alii Resort. This stunning 1,544 sq. ft. condominium offers a breathtaking high-up view of the Pacific Ocean and neighboring islands Lanai and Molokai. Ideal for a...
Kapalua Bay Villas | 3 Free Rental Cars | KBM Resorts | Panoramic Ocean Views | 3 Units, 4 Bedrooms | KBV ML-2083
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
The Famous Peacock House
The Famous Peacock House – Spacious & Whimsical Big Island RetreatWelcome to The Famous Peacock House, a vibrant and whimsical Hawaiian getaway designed for families and friends to create unforgettable memories together. With space for large groups, thoughtful...
700ft to Waikiki Beach • 1BR Condo • King Bed • Rooftop Pool
Stay just 700 ft from Waikīkī Beach in this newly remodeled 1BR condo with a king bed, balcony, and access to a rooftop pool, hot tub, sauna, and BBQ area. Perfectly located in the heart of Waikīkī, you’re only steps from the Duke’s Statue, top restaurants,...
Boutique Hotel Waikiki FREE parking
Excellent Location, free parkingEnjoy a comfortable stay in this independently owned hotel room featuring a king-size bed, along with a twin-size pull-out for a third guest if needed, full bathroom, central AC, and a flat screen TV. The room includes a mini fridge,...
Modern Princeville Retreat – Hanalei Bay Rental with Private Pool
This beautiful brand new home is overlooking Hanalei Bay & the beautiful tree canopy of Princeville. With a 10 min walk to the 1 Hotel beach, a short walk to Princeville Center and a quick drive to Hanalei Town, it is the ideal central north shore location. Featuring...
Waikiki Gem-Mins to Beach, Lanai w/City View, King Bed&Surf Lessons in Building!
Wake up steps from Waikiki Beach in this bright city-view studio at Kuhio Village Tower 2 — perfectly located just 2 minutes from the Duke Kahanamoku Statue and Kuhio Beach.Sip your morning coffee on the lanai and watch Waikiki come alive, then head downstairs for...
Step Out into Waikiki: Homely Hotel Perfect for Family Retreat | Outdoor Pool
Unwind in a spacious suite with private lanai, deep soaking tub, free WiFi, and plush bedding. Enjoy continental breakfast with Kona coffee, then stroll to Waikiki Beach or nearby shops. After exploring, relax by koi ponds or dip in the pool. Perfect for couples,...
Hale Malu: Gorgeous 5 BR Kauna'oa Home, 10-Minute Walk to Beaches!
Brand new and gorgeous private estate at the only community that is walking distance to the two best beaches on the Big Island, Mauna Kea and Hapuna! This home has a prime location atop a bluff in the luxurious Kauna'oa community. Built with open space and privacy in...
Peaceful 3 Bedroom Home with Fabulous Views
This is a minimum 31 day rental listingPerfect for extended vacation or traveling worker; traveling nurses or doctorsWell appointed, well maintained, privateBeautiful home in desirable, safe neighborhoodClose to beaches, shopping, town, golf, tennis and pickleball, as...
Wyndham Mauna Loa Village | 1BR King Bed Suite
Summary:If sunset cocktails, pools, and plenty of tennis sound like your style, you’ve found your spot. Located in Kailua-Kona next to a country club, this tranquil oasis sits away from town traffic and crowds while offering convenient access to the island’s many...
Stylized Captain's House
This Stylized Captain's House is located minutes away from family friendly scenic Kealakekua Bay beaches, the national park Pu'uhonua O Honaunau, & the island's best snorkeling spot "Two Step".An ideal setting for tropical adventures of all kind, offering spacious...
Mauna Lani Point G101
Welcome to your luxurious retreat at Mauna Lani Point G101, a stunning short-term rental nestled in the heart of Kamuela, Hawaii. This elegant 1-bedroom, 1-half-bathroom condo offers a perfect blend of comfort and style, ideal for your next getaway. Step inside to...
Kaanapali Alii Unit 1113
Welcome to the Kaanapali Alii Unit 1113, a luxurious vacation rental nestled in Maui’s exclusive Kaanapali Alii Resort. This stunning 1,723 sq. ft. condo offers a breathtaking ocean view, perfect for a relaxing and rejuvenating getaway. Step inside to find a...
Experience Oceanfront Bliss at Sugar Beach Resort 530
One of the best features to this tropical getaway is waking up to the sound of waves. Enjoy stunning views of Molokini, Kaho‘olawe, and the West Maui Mountains from your private lanai at Sugar Beach Resort 530. Just 60 feet from the ocean, this one-bedroom condo...
Scenic Kauai Stay Near Allerton Garden + Free Pool Access + Kitchen
Experience oceanfront serenity with stunning views, spacious rooms, a full kitchen, a private balcony, and in-room laundry—ideal for couples and families. Snorkel nearby, hike the Mahaulepu Trail, or spot turtles at Poipu Beach. Relax in our large outdoor pool....
Hale Makana: Portlock Luxury Home with Pool & Ocean Views
Set along Oahu’s exclusive Portlock coastline, Hale Makana is a refined single-level oceanfront estate that celebrates effortless island living. With postcard-worthy views of Diamond Head and the deep blue Pacific, this five-bedroom, seven-bath retreat blends...
Maui Ka’anapali Villas #137: Studio garden view condo at Beach Front Resort on N
Maui Ka’anapali Villas #137: Studio garden view condo at Beach Front Resort on N. Kaanapali Beach.This newly remodeled condominium is located on the ground floor, giving quick and easy access to the pool. This luxurious studio is furnished with a king-sized bed and a...
Modern Beach Apartment North Shore Home
Your Waialua adventure begins at this fantastic 1-bedroom apartment. The space features a queen bed, AC, a washing machine, and WiFi. The bathroom includes a shower and a hair dryer for your convenience. Nestled in a serene setting, this tremendous property is the...
Ke Alaula Hale 7 – Private & Secluded | Onsite Staff & Daily Housekeeping
This centrally-located 3-bedroom, 3.5 bathroom private home is a short 6-minute golf cart ride from the heart of the Four Seasons Resort. Designed for convenience and uncomplicated family living for up to 6 guests, this property offers a vaulted, wood-beamed great room...
Ocean view 1-bedroom condo at Maui Kaanapali Villas 292
Maui Kaanapali Villas 292 Remodeled Oceanview Getaway on North Kaanapali Beach Steps to the Beach, Pool and Hot TubWelcome to your Maui Retreat: Spend your next Maui vacation at this beautifully remodeled ocean-view condo located just steps from North Kaanapali Beach....
Honua Kai | 2 Free Rental Cars | KBM Resorts | Family Friendly | 2 Units, 3 Bedrooms | HK ML-1436
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
Kiahuna Plantation Resort 162 Ocean View 1 Bedroom
Soak in beautiful ocean views from this 2nd floor private one-bedroom retreat on Kauai’s most famous beach. Cozy, charming, and well-located, it’s everything you need for a relaxing island stay. Unit 162 Ocean View 1 Bedroom 1 Bath• Fully equipped kitchen includes...
Napili Bay Beach-Spacious 3Br Condo
Spacious 3BR Townhome – Steps to Napili Bay, Pool, Hot Tub & More!Welcome to your home away from home on Maui! Just steps from three stunning beaches—Napili Bay, Honokeana Cove, and Kapalua Bay—our spacious 3-bedroom, 2-bath townhome is perfect for families and...
Sunlit Island Escape in Kailua
Welcome to your island getaway! Nestled in the heart of Kailua, this bright and inviting home is perfectly located just minutes from Kailua Beach, where you can soak up the sun, enjoy crystal-clear waters, or try your hand at paddleboarding.This property combines modern...
KHV 36 Beautifully Remodeled Direct Oceanfront 3BD Kahana Condo, Steps to the Beach and Pool!
Kahana Village 36 NEW LISTING Spectacular 3Bedroom Beachfront Condo in Kahana with Amazing Ocean Views, and Privacy! Welcome to your dream getaway at Kahana Village—an oceanfront oasis nestled on the scenic shores of West Maui. This ground-floor condo boasts 1,566...
Maui Resort Rentals: Maui Kaanapali Villas 606 - 2BR Deluxe Oceanview Penthouse w/ Built-In BBQ & Panoramic Ocean Views!
Maui Resort Rentals is proud to present this jaw-dropping 6th-floor Deluxe Oceanview Penthouse Suite at Maui Kaanapali Villas—newly launched on 3/10/25 to start taking bookings beginning March 22nd, 2025!Never before available for vacation rental, Maui Kaanapali...
Charming studio at The Waikiki Grand in Waikiki with AC & Pool
Located in Honolulu, this fabulous studio is a dream. With a cozy living area featuring a Queen bed & futon up to 3 guests can relax in style. The bathroom offers a Shower / bathtub combo and hair dryer for added convenience. Our place is equipped for both long or short...
Spacious Ground Floor Maui Retreat, Grand Champion
Summary:🌴 Prime Location – 5-min stroll to Charley Young Beach🏊 Resort-Style Living – Pool, hot tub, BBQ & tennis courts🛏️ Ultimate Comfort – King bed + memory foam sofa bed🍹 Private Lanai – Sip cocktails with lush garden views🍽️ Chef’s...
Kaanapali Alii 3101
Welcome to your dream vacation in Maui! The Kaanapali Alii 3101 is a luxurious, family-friendly vacation rental that promises an unforgettable stay. Nestled in the exclusive Kaanapali Alii Resort, this stunning condominium offers breathtaking ocean views, refined...
Fabulous Poipu 7 bedrooms for 16! Amazing pool! New Listing
New Listing!! The Listing is made up of two separate townhomes just steps apart!This fabulous property located in wonderful proximity to Brenneckes, Poipu, and Kiahuna Beach!Surrounded by a championship golf course, the property enjoys a prime spot on Kauai’s sunny...
2 Bed 2 Bath 2 Parking at Cove Waikiki
Spacious 2 bed 2 bath 2 parking, end unit. A perfect home away from home that you will instantly fall in love with, and never want to leave! It sleeps 4, with one queen bed in the primary and two twin beds in the second bedroom. There is an AC unit in each room, free...
Kauna'oa 22 Five Bedroom Residence
Step into the Hawaiian serenity of Kauna’oa 22, a luxurious five-bedroom, six-bathroom villa offering sweeping views of the Kauna’oa golf course and the ultimate in indoor-outdoor living. This elegant retreat features a grand vaulted ceiling and a spacious open-plan...
Napili Point A27 – Relax by the Sea Savoring Maui Sunsets
Napili Point A27 is a one-bedroom, one-bath oceanfront condo with air conditioning that can accommodate up to four guests. It is in the highly desirable neighborhood of West Maui. This condo features a unique entryway that doubles as a second patio. The location of this...
North Shore Rustic Country Lodge 2-Story Yurt By Beach Waialua Haleiwa Glamping
Escape to this Tropical North Shore Island Nature Rental Retreat! 2.5 blocks to the beach & famous surf breaks. Rental is a 2-Story Yurt with a generous 1500+ square foot open-concept floor plan. Sleeps up to 11 people. Features kitchen & full bathroom amenities. Close...
Ilikai Two Bedroom, Two Bath Ocean View 8th Floor Corner
Corner suite with 2 balconies, 2 bedrooms & 2 bathrooms at the Ilikai Resort, a luxury high end condo with incredible views of the ocean, sunsets, lagoon & marina. Great fireworks show views every Friday night at 7:45pm. Upgraded and beautifully furnished complete with...
Charming Ilikai Marina Studio, Great Location In Waikiki!
Construction Notice 10/20/25: Exterior spall working is currently scheduled for 11/3 - 12/17/25 and painting work is currently scheduled from 8/10 - 9/4/26. During this time, the lanai will be locked and not accessible to guests. For your safety, please do not attempt...
Napili Point | 2 Free Rental Cars | KBM Resorts | Ocean View 1-bedroom Villa At Napili Point Maui | 2 Units, 2 Bedrooms | NAP ML-1547
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
Maui Resort Rentals: Honua Kai - 6 Total Bedrooms, Stunning 3rd Floor Ocean Views!
This premier 6-bedroom offering combines three neighboring 3rd-floor two-bedroom suites to create the perfect place for your group to gather, reconnect, and celebrate. Konea 303 and 305 occupy a fantastic interior courtyard location directly next door to one another and...
Just What You Were Looking For! Short Drive to Honolulu Zoo and Kuhio Beach!
In the heart of Waikiki near amazing beaches and attractions!This listing is for a room within a hotel.✦ Your room is 226 sq. ft, equipped with complimentary toiletries, TV.✦ Daily cleaning services included in the nightly price.There are a few additional details to...
Private Oceanfront Ohana Retreat Near Hanalei!
Enjoy the very best of Kauai’s north shore from this beautifully remodeled cliffside getaway in the heart of Princeville! Perfectly situated just minutes from Hanalei Bay & some of the world's most iconic surf spots. Step outside to enjoy warm trade wind breezes,...
New Listing! Villa with an island charm interior
Welcome to Kapalua Ridge Villas 2712 – a bright and breezy 1-bedroom, 2-bathroom ground-floor villa that comfortably sleeps up to 6 guests. Step inside to discover an airy, open-concept living space with A/C, and large windows to showcase serene ocean and garden...
Paradise by the beach
This is a beautiful 5 bed, 3 bath home that sleeps 12. It is located just steps from famous Hukilau Beach, and within walking distance from BYU Hawaii. There is a washer and dryer, two living rooms, office room, and much more. Enjoy a sunrise stroll on the beach, spend...
Kaanapali Alii | 283
Welcome to Kaanapali Alii 283, a luxury vacation rental that promises an unforgettable stay in a tropical paradise. Nestled on the eighth floor of the Kaanapali Alii complex, this two-bedroom condo offers stunning ocean views from every window, immersing you in the...
4BR Mokulua Seaside w/ Private Studio, Steps to the Beach
Mokulua Seaside by Gather is a refined oceanside escape that brings together luxury, space, and the beauty of Lanikai. Just one house from the sand on Kailua’s coveted Mokulua Drive, this four-bedroom, four-bathroom retreat spans 3,316 square feet of interior living...