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.
Private Penthouse Getaway At Waikoloa Beach Resort 5 minutes from A-Bay Beach
Beach Access, A-Bay Beach, a 5 minute drive. Our beautiful luxurious two-bedroom, two-bath penthouse condo located in a private gated community. Enjoy your vacation in a tropical paradise at the Waikoloa Beach Villas. From our third floor, enjoy beautiful mountain and...
Beautiful Top Floor Waikiki Studio! Walk to Beach!
Summary:Experience the best of both worlds with this beautifully appointed 18th-floor studio in the serene Ilikai Marina, an oceanfront building on the quieter side of Waikiki. Just a short stroll to the soft sands of Waikiki Beach, you can soak up the sun, feel the...
Poipu Crater 20 - A/C, Close to Beaches
POIPU CRATER 20 AT KOLOA KAI VACATION RENTALSA Unique Hawaiian Retreat Inside a Tropical CraterWelcome to Poipu Crater 20, a charming and secluded two-bedroom condo nestled within a dormant volcanic crater. Surrounded by lush tropical gardens and vibrant birdlife, this...
Direct Ocean Front - Renovation Complete - EVERYTHING inside is NEW!
Welcome to "Poipu Palms #103". We just finished the process of completing an "extreme" renovation on this condo. This was not just a "redecorating", but a complete tear down and rebuild. (Please forgive the snapshots). We will be posting professional pictures in the...
5-STAR KONA COAST RESORT 2 bedr/2 bath Top Floor, AC, GORGEOUS Unit#10-301!
Kona Coast Resort #10-301 is one of the best ocean view 2 bedroom, 2 bath condos, with all of the amazing amenities of a 5-Star Resort! Enjoy two Swimming Pools, one “family” pool with an on-site Restaurant/bar, and nightly live music plus one quiet pool, three...
Poipu Kai 3 Bedroom with Pool and Spa steps to Shipwreck Beach
Brand New Listing Located in the upscale Poipu Kai neighborhood this new home embodies pure enjoyment and relaxation. The layout of this three bedroom single level home offers all the room and privacy for a trip of a lifetime. The large pool and spa will keep you...
Waikoloa Beach 2bdrm/2ba remodeled condo close to the beach.
Enjoy our remodeled 2 bedroom condo conveniently located close to the resort pool and Pavilion. This condo is well equipped and used exclusively for guests. It is a corner unit located on the ground floor with easy access from the reserved parking space. Also, we are...
Oceanfront Tranquility at Hale Maluhia, Kona Coast
Beautiful oceanfront property featuring a private gated home with two additional separate king Bedroom Suites, each with private entrances. Enjoy unobstructed ocean views of the Pacific Ocean, Kona Coast, and Kahalu'u Beach with stunning sunsets. This property includes...
Maui Resort Rentals: Honua Kai - 4 Total Bedrooms, 8th Floor "Penthouse" Ocean AND West Maui Mountain Views, Deluxe Corner Floor Plan!
This premier eighth-floor offering pairs one of our most sought-after two-bedroom "penthouse" suites with two neighboring one-bedroom suites to create the perfect place for your group to gather, reconnect, and celebrate. Enjoy unparalleled views of the blue Pacific...
* * June 1 to June 5 Deal! * * OCEANFRONT NEWLY RENOVATED CONDO "AMAZING VIEWS"
June 1 to June 5th special $150 per night!!! FREE HI SPEED WIRELESS INTERNET CONNECTIONFREE LONG DISTANCE CALLING TO USA AND CANADAOcean front condo has been recently remodeled100 feet from one of the finest beaches in MauiWonderful snorkeling and water sports at your...
Best View in Town, A205 come check out the View
Lokelani A205. Enjoy breathtaking, unobstructed views of neighboring islands Molokai and Lanai. The surf is just 30 feet away from two private balconies – the perfect vantage point for whale and sea turtle watching, as well as our legendary Hawaiian sunsets. Enjoy the...
Tranquility on West Moloka'i
Kick back and relax in this calm, stylish space. This one bedroom, one bathroom condo is located in the Kanaini Kai development on West Molokai. Featuring a spacious floor plan with a full kitchen and an amazing lanai with views of the ocean and Papohaku Beach (longest...
2 Bedroom/2 Bath Luxury Oceanfront Resort Vistas
Summary:Fully remodeled and professionally decorated in April 2023 with all new furnishings. This elegant 2-bedroom, 2-bath condo features luxurious touches paired with oceanfront serenity. Located in sunny Kihei at Menehune Shores resort, all of Maui is within reach....
Pohailani #113 - Vacation West Maui - Gorgeous Studio with AC
This studio is perfect for travelers who want to be close to the ocean and enjoy all the amenities of a vacation rental. Just a short walk from local restaurants and coffee shops, making it easy to grab a bite to eat or a coffee on the go. This property features on-site...
Kahana Manor #603 - Vacation West Maui - Oceanview Near Beaches and Restaurants
Rest peacefully on our incredibly comfortable beds and wake up refreshed, ready to embark on another incredible day in Maui!This charming condo features:2 bedrooms and 2 bathrooms, accommodating up to 6 guestsSituated in an amazing location in Northwest Maui, with close...
Pele's Paradise- Absolute Oceanfront Paradise with Air Conditioning!
Peaceful oceanfront paradise! Absolute oceanfront paradise on lava cliffs centrally-located between Hilo, Volcano's National Park and Pahoa. See whales (in season November-March), sea turtles and spinner dolphins right from your backyard! Fully remodeled with tasteful...
Unrivaled S Kihei Maui location! Walk to it all!
This home away from home contains everything you will need for a memorable getaway— including beach chairs, cooler, umbrella, beach towels; fully stocked kitchen including NEW dishwasher and refreshed cabinets and lighting; beach vibe abounds in the living/dining room...
Hula House - Beachfront North Shore Oahu
REMAINDER OF 2025 SPECIALS!BASE RENT REDUCTIONS FOR OCTOBER AND NOVEMBER FROM $15240 TO $14000DECEMBER FROM $21000 TO $19000.This spacious modern ocean front homes is beachfront luxury on the north shore. Unobstructed views of the ocean welcome the guests from both...
Beautiful Mountain Views & Steps to Waikiki Beach
Aloha from Midway Vacations, your local experts in paradise! Enjoy spotless, well-kept homes, island hospitality, and 24/7 support for a worry-free Hawaiian escape.Experience the charm of this corner unit with lanai on the 29th floor of the Waikiki Banyan, ideally...
Ocean view, fully remodeled, 2nd floor, few steps away from the best beaches
**Welcome to Your Perfect Maui Getaway!**Nestled on the second floor with breathtaking views, our recently remodeled rental unit offers a seamless blend of modern comfort and coastal tranquility. Enjoy stunning vistas from the lanai, overlooking a beautiful green belt...
Aqua Aloha Surf Waikiki 1007 Deluxe Studio with Lanai and Partial City Views
Aqua Aloha Surf Waikiki #1007, Deluxe Studio with Lanai and Partial City Views located just 2 Blocks to Waikiki Beach, (1) Queen bed, (1) Queens Sofa Sleeper, Sleeps 4 360 St FtAqua Aloha Surf Waikiki offers a range of accommodations that are perfect for couples and...
Short walk to two beaches in Poipu Kai Resort, Mt. view from Lanai- Makanui #712
Welcome to paradise in this two bedroom, two bath, no stairs ground floor condo that lives like a house. Your favorite part just might be the massive lanai that spans the length of the unit and provides ample room to sunbathe, curl up with a book, or dine in tropical...
Ocean View Family Condo Across From Lyman’s Cove~Air Conditioning~Calif King Bed
There may be scaffolding and a tarp on the exterior of the building for painting beginning 12/1/25. Royal Kahili A402Beautiful OCEAN VIEW and pool view from our fourth story condo! Top floor, no overhead neighbors!Elevator works as of 8/10/2023!You will need to...
Huge Ocean Views - Poipu - A/C - Pool - W/D - Fun
Experience exceptional Ocean views and sunsets from this extraordinary lanai. You can see dolphins, whales(seasonal), and natures beautiful colors while you're eating or relaxing. World class and family friendly beaches are just a short stroll away. Poipu is on Kauai's...
Two-story ocean view home with a furnished patio & deck, washer/dryer, & AC
Ka Hale me Ka ike 30 Night MinimumOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Take in the amazing view from both inside and out at this four-bedroom, family-friendly retreat here...
A Beautiful View Beach House at Kahalu'u Bay! Snorkeling & Surfing ~ Steps Away!
This is a very special property within a treasure of history, located across the street from Kahalu'u Bay & Beach Park on the mauka side of Ali'i Drive. Known for world class snorkeling with beautiful coral reefs, bright fish, sea turtles & a super fun ~ surf break....
Updated condo with furnished lanai & washer/dryer plus pool & tennis
Hale Kamaole 144Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'This ground-floor getaway is a bright and spacious oasis located just steps from the ocean! Enjoy evenings watching...
KBR 3302 · Simple but Idyllic Oceanfront Resort w King Bed
Hotel Room at the Kauai Beach Resort located in Full Service Oceanfront Resort just 5 minutes from the Airport. This is a third floor unit with a sliding door to a lanai overlooking the Luxury Pool Area and direct access to the ocean. The Pool area includes several...
Amazing waikiki Beach condo 2Bed2Bath+free Parking
Listing descriptionAloha, thanks for checking in our property.A newly remodeled 2 bedrooms and 2 full baths (2023). There are 4 double and 2 single beds, full kitchen with kitchenette. It's spacious, almost 1,000 sq. ft. with a patio. It is on the top floor (17) of the...
Ocean-View Maui Sunset B217 • Modern 2BR • Sleeps 7 • Walk to Beach
Spacious 2 bedroom, beachfront condo, recently renovated and beautifully decorated for a fresh, clean, beachy feel. Enter this luxurious open floorplan to hardwood flooring throughout and stunning ocean views from the living room AND kitchen. Huge wall of windows with...
Aloha Condos, Keauhou Resort, Condo 108, Ocean View, AC
Experience perfection at Keauhou Resort Condo 108! This immaculate, renovated condo offers stunning ocean views, breathtaking sunsets, and stellar stargazing from your private lanai. Enjoy top-notch amenities, a fully equipped kitchen, reverse osmosis drinking water,...
Maui Resort Rentals: Honua Kai Hokulani 650 – 6th Floor Oceanfront 3BR King Kamehameha Suite. 5800+ Sq. Ft. of Indoor/Outdoor Living Area!
We are proud to present this jaw-dropping 3BR/3.5BA oceanfront King Kamehameha Suite representing the pinnacle of resort accommodations on Maui. From the moment you enter this oceanfront paradise, you will be struck by its stunning 6th-floor location boasting...
Surfer's paradise on Oahu's North Shore - Split ACs
Aloha & Welcome to our stunning condo located at the Kuilima Condos at Turtle Bay, on the North Shore of Oahu. Our condo is the perfect destination for those seeking a luxurious and relaxing vacation in paradise with two Split AC units that keeps the place cool...
KBM Resorts | FREE CAR | Islands at Mauna Lani | Newly renovated ground floor 2-Bedroom Condo IML-E4
** 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...
Family Retreat Resort Condo- Full Kitchen, AC, Laundry- Walk to Beach and Shops
Cozy 1BR Condo in the Heart of Kihei – Walk to Beach!Escape to sunny Kihei, where this charming one-bedroom condo puts you just a short walk from Kamaole Beach Parks 2 & 3—perfect for sunbathing, swimming, and catching breathtaking sunsets. With beach gear provided...
Steps to beach! Gorgeous renovated partial ocean view condo at Waikiki Shore!
Waikiki Shore #515 – 2161 Kalia Rd.NEW TO OUR INVENTORY! Waikiki Shore is the only condo in Waikiki where you can step directly from the building onto the sands of Waikiki Beach! This exquisitely remodeled (2023) 5th-floor beachfront studio is a favorite with return...
Updated Kauhale Makai unit 610 1 bedroom top floor, king bed, AC
• Oceanfront• Central A/C unit• King bed• Remolded May2023• Beach access from condo complexWelcome to our home at Kauhale Makai 610. Our home was updated in May of 2023. Our beautiful and pristine one-bedroom condo sits on the top (sixth floor) of the complex. The...
S&N Lux suite/Free Parking/King Bed/Kitchen/Wi-Fi
Experience luxury in our modern suite in Honolulu, Hawaii. Nestled amidst European-style gardens, our resort harmonizes with Oahu's tropical charm. Relax in the outdoor pool, stroll through the garden, stay fit in our gym, or unwind in the sauna. Explore Honolulu's...
Kukui'ula Villa 8: Oceanview Condo w/AC/Private Lanai, Walk to Shops/Restaurants
Escape to Kukui'ula Villa #8 by Gather and settle into a refined island retreat in the heart of Poipu. This second-level villa blends chic contemporary design with sweeping ocean, garden, and mountain views, offering 1,484 square feet of bright, breezy living space....
Discount ending soon! Ocean View - 1 Bedroom Villa - Marriott's Ko’Olina -
Unit sleeps 4 (website error says sleeps 6). Discover paradise in our stunning 1 Bedroom Villa at Marriott's Ko Olina Beach Club! Enjoy breathtaking ocean views from your private balcony while relishing the luxurious amenities and exclusive activities we offer.Our...
Tropical Garden Getaway
Prime location for a Paradise Big Island experience! Enjoy peaceful, relaxing nights in Seaview Estates at the Tropical Garden Getaway. This luxurious garden ohana unit on the first floor has a private entrance, deluxe queen bed in one room with morning views of a giant...
Oceanview Suites + Cottage + Addtl. Bed/Bath
Luxury Oceanview Estate – 2 Suites + Cottage + Additional Bedroom | Infinity Pool | Gym | High-Speed Wi-FiWe are a 3 Acre Luxury Vacation Rental Property with an Award Winning Coffee Farm comfortably nestled on the slopes of Hualalai overlooking Kailua-Kona.We offer...
Ekahi 27A: Priceless Ocean View from a Private Lanai
Private corner unit, 1 bedroom 1 bathroom with 2 private lanais. Ocean view. Have all your meals in our large private lanai. Watch breath taking sunsets without leaving home. Brand new wood floors around the entire condo. New air conditioner in living room and bedroom.
The Jungalow is a charming renovated bungalow minutes from Volcano National Park
The Jungalow is a charming bungalow nestled among native hapu'u tree ferns and ohi'a trees in the high rain forest. The Jungalow has been lovingly restored with attention to detail. Recent upgrades include new exterior and interior paint, new driveway and landscaping,...
Two homes on the ocean with a private saltwater pool.
The Cliff House is has two detached structures each with its own full kitchens. The private saltwater pool is on the ocean-side with a large shaded patio. Perfect for large families, co-workers and/or friends to gather in one place but have separate, private living...
Estate on Tropical Acre - Harmony in Paradise
Modern home, over 3,500 sq ft; a resort-quality property that can sleep up to 10 guests, on an amazingly lush, fully-landscaped acre. Large living room, exceptional kitchen and dining areas, four lovely bedrooms, a study has been equipped with children in mind, and...
Amazing 3 Bed Townhome with Private Beach Club
Luxurious vacationing at its best in this custom 3 Bed/3 Bath Townhome. Full air mattress can be set up in the office area to expand the number of guests to 8. A custom kitchen, outdoor grilling area, gorgeous bathrooms with washlet toilets, a dedicated office area,...
Luxury Villa! Views! 1/2 mile to beach! Huge lanai! Hilton Pass for entire stay!
Resort life awaits you in the Shores at Waikoloa in this beautiful condo overlooking the golf course—only half of a mile from the beach. Cooling cross breezes and central A/C provide year-round comfort. The spacious layout ensures privacy for each side of the condo. The...
Hale Ono Loa 114
Welcome to Hale Ono Loa 114. This 1 bed/ 1 bathroom ground floor, ocean view gem has everything needed to make amazing Maui memories. This unit can comfortably accommodate 4 people, offers a fully equipped kitchen, & outdoor dining area to enjoy your ocean view. Admire...
Bali-Inspired White Sand Beachfront House w/ Large Deck, GYM, & Lots of Toys!nn
Imagine walking out the back gate of your beachfront vacation home, entering a private path with tropical trees overhead and white sand beneath your toes. Then you see it, the turquoise blue water, waves, rays, and views of Three Tables Beach that you and your loved...