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.
Turtle Bay Fairway Condo - Kuilima Estates East
Welcome to your North Shore paradise! Step into our fully remodeled Turtle bay condo, boasting breathtaking views of the 18th hole through wall-to-wall windows. Outside, Indulge in luxury with 2 private pools, tennis and pickleball courts, and 5+ miles of pristine...
Vacation in Style and Comfort at the 'NEW' Eldorado - 2BR - Building B
2 BEDROOM 1 BATHROOMThis 2 bedroom Maui Eldorado Resort condominium located on the main floor of Building B has been completely upgraded and renovated. It features:• Large, sleek fully-equipped kitchen with a large 6’ x 3’ island with 4 bar stool chairs, granite...
Hualalai Haliipua Villa 104
Haliipua Villas are the newest generation of multi-family villas at Hualalai offering an array of designer finishes throughout the home. Special features include luxurious mahogany finishes, island-inspired ceiling treatments, enhanced lighting systems, built-in lanai...
❤️PiH❤️ HAWAII ROMA ★ Hilton Pool & Waterslide Passes ★ Golf Course, Sunset Views ★
Brought to you by Paradise in Hawaii Luxury HomesWelcome to Hawaii Roma at KaMilo, a part of our Hawaiian Luxury Collection and a wonderful 4 bedroom home.We pride ourselves on providing some of the most sought after homes on the Kohala Coast and are thrilled to add...
Plumeria Room on a Lush Farm on Maui's North Shore
A cozy room offering a king-size bed and a queen size bed. Guests can enjoy a small refrigerator, microwave, electric kettle, coffee pot, desk, private bathroom with shower, large closet, and a small outdoor sitting area. As guests of Hale Akua Garden Farm & Eco-Retreat...
Resort Townhome, Close to Shops, Restaurants & Beach
Aloha and Welcome to Leilani at the Beach Villas in Waikoloa Beach ResortYour perfect Hawaiian vacation begins here. From lush, palms and lava rock swimming pools to a private kitchen and breezy lanais scented with tropical flowers, Leilani offers an effortless escape...
Coconut Plantation 1078-1: Bright 3BR Beach Home Steps from Ko Olina Attractions
Welcome to Coconut Plantation 1078-1, a spacious 3-bedroom, 3-bath townhome in the heart of Ko Olina Resort on Oahu’s sunny leeward coast. Offered exclusively as a monthly rental, this 1,548-square-foot retreat combines comfort, convenience, and the laid-back elegance...
🌺Paradise awaits you...Come experience our "Ohana Beach Condo" 🌺
Our Maui Paradise awaits you! Be our guest at our "Ohana Beach Condos " VRBO #1628652... Our newly updated unit is on the southwest side of Maui, located next door to Wailea in sunny Kihei. This Maui resort is a complex of three beautifully landscaped buildings. Our one...
Incredible Views Milowai 1 Bed 1 Bath Condo
A peaceful retreat where you can hear the ocean waves from your king size bed. Sunrise and sunset views from your lanai. Located on the 3rd floor with elevator access. Milowai complex has a heated pool with BBQ`s and a small library for guests use. There is a 5-mile...
Beautiful Ocean & Mountain View Condominium
Relax on our second story lanai and enjoy views of the blue Pacific, majestic mountains, and cascading waterfalls. Watch the sunset with your family from your lanai, or walk 50 feet to the end of the cliff for more views and the sounds of the ocean. Wake up in the...
Maui 🌺 Private Home in Wailea Kihei with 3 bed 2 bath Best Beaches on Maui
Our Eco Friendly home is conveniently located near Maui’s most beautiful beaches. Minutes away from Wailea Beach, Keawakapu Beach, Kamaole Beach III and the famous Big Beach. Also, sitting at the base of Haleakala you will have opportunities to adventure to incredible...
ULTRA LUXURY OCEANFRONT 2Bd/ 2Ba Fully Renovated!
This sixth floor, oceanfront, luxury unit opens up onto your very own private patio with stunning, FULL ocean views. Complete with lounge chairs and outdoor seating, just steps from the turquoise waters of the Pacific Ocean, your paradise awaits.Relax in your king sized...
Honua Kai H825 Luxurious Kaanapali Beach 3BD Condo with Beautiful Ocean Views
The Stice Team — Powered by Gather Vacations. Maui Born and Raised Professionals. Your Local Experts in Crafting Unforgettable Stays.Welcome to Honua Kai Hokulani 825, an eighth-floor 3-bedroom, 3-bath penthouse style residence that sleeps up to 10 guests and frames...
Villa On The Ocean - One Of Largest Condos On Alii Drive. Directly Oceanfront.
This is an absolute Oceanfront Villa. Watch the dolphins while you have breakfast.This wonderful Villa offers oceanfront amenities including the fragrance of the ocean spray and warm tropical breezes truly distinctive to Hawaii!Welcome to this two bedroom, two and...
Stunning, spacious home with VIP access to private Mauna Lani Beach Club!
AMAZING PROPERTY!! VERY PRIVATE & VERY SPACIOUS HOME, INCLUDES VIP PASS TO PRIVATE BEACH CLUB.This Phase One Maile plan with its direct west facing view and end of cul-de-sac location is a gem. Immaculately maintained with many developer and custom upgrades. The custom...
1 bedroom ocean view condo on Kaanapali beachfront -- Recently renovated!
This 5th floor condominium (elevator bank nearby) offers ocean views from the master bedroom, living/dining room, and lanai, this spacious 1 bedroom unit offers you the opportunity to fully enjoy the spectacular Kaanapali Shores ocean front resort. The unit offers a...
Discovery Bay-Resolution Ocean View Condo
Oceanview 1 Bedroom, 1 Bathroom Sleeps Up to 4 Condo DescriptionLooking to travel to the island for business or extended vacation? This large newly renovated 1 bedroom unit has everything you need that will make you feel at home while reminding you that you are on a...
Private1BR @Waikiki Max 6! near Ala Moana Center!
【Basic Info】This is a 1BR room in Waikiki!!You can stay with you friends, partner, family. You can spend your time with a reasonable price.This condominium is located west area in Waikiki.You can walk to Hilton village lagoon and beach and Kahanamoku beach in...
Pono Pearl Villas | Beach Access + AC In Every Room
Just a short walk from the beach, this spacious home is ideal for family reunions, retreats, or groups looking for space, privacy, and easy shoreline access. This listing represents one of several similarly appointed homes in the Windward area. All units share the same...
5 Star Luxury Beach Villa ~ Mountain, lake and golf views. BBQ on the lanai!
Indulge In Quality And Comfort In Our Tropical Condo For Your Island Get Away, Perfect For Unwinding After A Day Of Exploring. We Are Directly Across From One Of Two Lagoon Style Pools And BBQ Areas And Right On The 8th Fairway Of The Beautiful Waikoloa Beach Golf...
Paia beach house with huge ocean view and only one minute walk to Kuau beach
Maui County Rental permit - STPH 2018/0003 (this is a legal, permitted Maui vacation rental)TA-066-523-9552-02 / GE-066-523-9552-02 TMK-260090240001It's a Beach House! A place to relax, unwind, listen to the breeze through the palm trees, absorb the ocean views. Start...
Steps to Beach. Stunning View. Lovely 2BR Condo near Wailea
Enjoy paradise at one of Maui's premier beaches. Our air-conditioned retreat features a clean and bright interior, offering stunning views from the main living area. Enjoy cooking in a well-equipped kitchen and relax with beach chairs, umbrellas, and boogie boards...
Panoramic Ocean View B&B on Kohala Coast-Holiday/Winter/Summer Rate 285.
This lovely private Big Island bed and breakfast, just four miles from Hawaii's most beautiful white-sand beaches, continues to be one of the most sought-after locations. Free parking on property, includes daily breakfast and AC. The consistently sunny skies,...
Monthly Discovery Bay 2810 Studio Ocean / Sunset / Marina Views King Bed, Sofa Bed
PANORAMIC Ocean VIEWS, 5 Minute Walk to Beach, High Floor, Remodeled, Furnished and Fully Appointed. No smoking room. Parking, Pool, Utilities, WIFI, BBQ, Gym, Security, Washer/Dryer Included. 1 Month Minimum / contact Agent.Sweeping Ocean Views from High Rise, Tasteful...
Waipouli Beach Resort Courtyard View 2 BD 3 BA
This well-appointed two-bedroom condo overlooks a beautifully landscaped courtyard, creating a soothing atmosphere. Perfect for a Kauai getaway, it offers plenty of space to unwind and enjoy island life.Courtyard View 2 Bedroom 3 Bathroom• Kitchen features granite...
Hale Alaula, Elegant Hawaiian Home at exclusive Sunset Drive
Hale Alaula, Princeville Welcome to Hale Alaula, a stunning high-end plantation style home located on golf course greens in Sunset Drive, Princeville. Alaula, meaning "Sunset Glow" in Hawaiian, is just that. Hale Alaula is situated in the exclusive Sunset Drive...
WOW!! - WHALER's BEST STUDIO - Posh Remodel-10th Fl.- PANORAMIC Ocean Views!!!!
Unit 1064 is the ABSOLUTE nicest studio at The Whaler !!! Unit 1064 has been completely remodeled and professionally decorated just a few years ago... Unit 1064 has EXPANSIVE & PANORAMIC views of the OCEAN, the island of Molokai, the Kaanapali beach Boardwalk, Blackrock...
Spacious Beachfront 1 BR + Loft (sleeps up to 5)
When the developer built this 18 unit condominium in 1973, he saved this unit for his family. One look will tell you why. It is the largest unit in the complex and is wonderfully spacious and open. Decorated in seaside colors, our unit provides a roomy, calm...
Kehena Black Sand Beach House: 2 BR Eco-Retreat with Ocean View & Swim Spa
The ultimate Hawaii eco-retreat. Timeless design for indoor-outdoor relaxation, dining and sleeping. Experience ocean views and crashing waves from wide-open bifold doors. Walk nextdoor to Kehena black sand beach, or drive the Red Road to the state's only hot springs at...
Aloha Condos, Na Hale O Keauhou, Townhome L-6, Ocean View, AC
Welcome to Aloha!! Listen to the crashing surf from gorgeous Na Hale O Keauhou L-6. Spacious 2-story luxury air-conditioned Townhome with Panoramic Ocean Views. This wonderful remodeled and upgraded unit features 3 Bedrooms, 3 Baths, well-appointed kitchen and full...
Oceanfront Puu Poa Condo 311 AC thruout best Bali Hai View & Sunsets Princeville
Our Oceanfront, Mountain and Sunset view is THE most famous on all of Kaua'i!!!Newly renovated with A/C throughout unit. 4 split Mitsubishi units: one in each bedroom , one in kitchen/dining area and one in living room/atrium area.If you are looking for the most...
Ohana Retreat - The Real Hawaiian Experience
Experience the Beauty of Hawaii at Ohana RetreatOhana Retreat is the ultimate getaway for large families looking to embrace the breathtaking beauty of Hawaii. Our spacious island-style home features eight luxurious bedroom suites, each complete with a private bath, wet...
Experience Tropical Tranquility: Luxury Studio Home in Hilo!
Experience convenient and comfortable living staying at our studio in our newly built duplex home. Located centrally in Hilo. You will be just 3 miles from Hilo airport, Liliuokalani Park and Garden, Carlsmith Beach Park, and many other popular attractions and...
Hololani Resort #A104 - Vacation West Maui - Oceanfront at Kahana
Hololani Resort A104 is a stunning resort condominium featuring spacious and elegant designs, offering panoramic views of the Pacific Ocean and the nearby islands of Molokai and Lanai. The condo comes equipped with all the modern amenities you need for a comfortable and...
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....
FREE Auberge/Mauna Lani Fitness Club Access @ this nearby Palm Villas Condo
E KOMO MAI TO THE PALM VILLASThis 2BR/2Bath ground-floor Palm Villas unit is private and secluded, surrounded by 6 acres of lush landscaping. Through Oct. 4, 2026 you will have full access to the Auberge/Mauna Lani Fitness Center, located across the street. Play tennis...
180 Degree Ocean View in Wailea! WE204
Welcome to Wailea Ekolu Village, unit 204! This is a top floor, FRONT LINE, two bed, two bath condo with a 180 degree ocean view! Overlooking the Wailea Blue Golf Course course, this unit boasts dramatic ocean views! The interior has been extensively remodeled and...
Kauai Oasis - Luxury 6 BR Kukui'ula Estate with Infinity Pool
Magnificent, spectacular, and amazing describe Kauai Oasis, a brand-new 2024 Kukuiʻula retreat. This luxurious home offers sweeping views of the ocean, Kukuiʻula golf course, Hā‘upu mountains, sunrise, and full moonrise. Watch the Milky Way and meteor showers from...
Lavish Premier Beachfront Townhouse W/ Unrivaled Views Wailea Elua 1305
Wailea Elua #1305 – Premier Oceanfront Townhouse for Elevated Maui LivingWelcome to Wailea Elua #1305, a luxury 3-bedroom, 3-bathroom oceanfront townhouse designed for travelers seeking the finest in comfort, privacy, and sophistication. Meticulously remodeled and...
Hale Waima Lani - Luxury Oceanfront Estate in Puako
Modern luxury and old Hawaii charm meet and beckon from one of the largest oceanfront lots in Puako. With 350+ feet of beachfront access and ocean views from every room, this unique and meticulously maintained home is a vacation dream—the main hale with a luxury...
Walk to Kalapaki Beach: Condo w/ Ocean & Mtn View!
Banyan Harbor | Saltwater Pool Access | Near Shopping & DiningSay hello to a prime location with 24-hour security and an easy drive to the North and South shores at this Lihue vacation rental. This single-level unit features 2 bedrooms, each with a private full...
Ocean Front Beach House located only steps from the water!
E Komo Mai!At Nalu Hale (surf house) we welcome you to emerse yourself in surf culture. Wake up to the waves crashing on the shore of Kahalu'u Bay and never miss a sunset. Whether you like to surf, sup or snorkel, Nalu Hale puts you just steps from your next ocean...
Stunning Beachfront - Hale Kai O Kihei 112
Welcome to your perfect escape in Kihei! This bright and beautifully updated oceanfront ground-floor one-bedroom condo is just steps away from the beach, offering breathtaking views and modern comforts. Ideal for couples or small families, this inviting retreat features...
Fairway Villas-2 Bed/2 Bath Lots of updates! Close to golf, shopping, and ocean
Welcome to our family’s piece of paradise. We’ve been travelling to Hawaii for twenty years, and our condo is the fulfillment of a dream to call the Big Island our second home. Our goal is to provide you with that same sense of aloha.Our 2BR/2 BA condo has a king in...
PINEAPPLE HILL KAPALUA-SILVERSWORD-4 BEDROOM-4.5 BATHS-PANORAMIC OCEAN VIEWS
Nestled in the luxurious KAPALUA RESORT, this custom home is located in the prestigious gated community of Pineapple Hill. The 4-bedroom, 4.5 bath residence, encompassing over 3500 square feet, has 1 Master Suite, 3 Bedroom Suites (2nd Floor) and 2 smaller rooms that...
**Fairways Mauna Lani #1606 - Luxurious 2-Bedroom Retreat: 2 King beds, Remodele
**Fairways Mauna Lani #1606 - Luxurious 2-Bedroom Retreat: 2 King beds, Remodeled with Spa-Like Bathrooms, Steps from the Pool!**Please scroll down for detailed informationWelcome to your dream getaway! This beautifully remodeled 2-bedroom, 2-bathroom townhome is...
Ko Olina Beach Villa Ocean View 3BR/3BA - B907
Penthouse Beach Tower 9th Fl (B907) - Steps from the Ocean. Escape to a Hawaiian Paradise at the Beach Villas Palekaiko on Oahu! Sleeps up to 8.The Palekiko welcomes you to paradise from the moment you walk in the door with all you need to relax and rejuvenate during...
Hualalai Palm Villa 140C
NOTE: New photos coming soon. This property is under complete renovation for Fall of 2025!The spacious floor plan includes a downstairs primary bedroom suite and luxury spa-like bath. Just off the master is a large living room that opens to the downstairs lanai, leading...
Remodeled ground floor Kihei condo, walk to some of the best beaches
Welcome to Kihei Akahi C103. This beautifully remodeled ground floor condo is the perfect place to make your Maui memories. This condo is fully equipped to accommodate 4 guests, & has beach gear for your use. There is AC in the living room only, and ceiling fans...
Ground-Floor Retreat W/Ocean Views-Kiahuna 2166
Kiahuna Plantation unit 2166: This modern tropical one-bedroom ocean view unit on the ground floor is a rare find and provides the utmost comfort with cool flooring and decorative carpeting, two cooling ceiling fans, and floor-to-ceiling windows allowing for plenty of...