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.
Stunning oceanfront view with private lanai
Kulakane 212 is a stunning oceanfront condo that features spectacular ocean views! This beautiful 1-bedroom, 1-bathroom condo is on the 2nd floor and can accommodate up to 4 guests . Please note this resort does not have elevators. Enjoy Maui's blue waters with a cup of...
★Jump Start The Road to Hana at The Lookout House! Private Hot Tub + Pool Access
The Lookout House at Huelo Point Lookout in Maui is the perfect home base for exploring the island. The location of the house off the Hana Highway makes it a great starting point for your Road to Hana adventure. The famous scenic drive to Hana is a must-do activity for...
Right on the water in West Maui.
Looking for a getaway that is right on the water with a full ocean view on the west side of Maui? This condominium has a full kitchen with stainless steel appliances including a dishwasher to create your own meals and save money on your vacation. Features a king size...
Stunning! Fully Air-Conditioned Penthouse Level Ocean Front 1 Bedroom - #609
Simply Exquisite! The photos say it all!This fully air-conditioned penthouse level unit is sure to make your stay in Paradise a romantic and memorable one! Recently remodelled and expertly finished by the best tradesmen, it boasts travertine marble flooring throughout,...
Romantic Cottage, Stunning Ocean Views, Whales are jumping!
James Cottage is a historic home that has been completely restored for our guests to enjoy. Located with in The Historic Puakea Ranch, your bungalow was once home to the paniolos who lived and worked at Puakea 100 years ago. Ocean views, light filled, airy and...
1 Bed/2 Bath Condo with Sensational Ocean View
Welcome to paradise at Maui Kamaole's J115. The breathtaking view from our condo will entice you to stay here. You'll want to return because it's a clean, quiet, well-appointed, well-equipped retreat with plenty of extras. You'll love the gentle trade winds that sneak...
Luxury Mahana 1bd/2ba-Beautiful Remodel- Incredible Views-Free Parking/WiFi
Mahana 715 is a 1BD/2BA condo featuring the best direct beachfront location, panoramic Pacific Ocean views, year round sunsets, and seasonal whale watching at its finest. The Mahana is one of a kind with its close proximity to the water and there is truly nothing like...
Pili Mai 10 I: Luxury Resort-Style Condo, Pool+Spa
Elegant design meets luxurious comfort in this beautifully bright, airy 3BR/2.5 BA townhome in the acclaimed Pili Mai at Poipu vacation-resort complex. Inside and out, the artistically color-coordinated furnishings are a rhapsody in oceanic blues—indigo, cobalt,...
Waikiki Shore 1302
Waikiki Shore #1302 – 2161 Kalia Rd.(ALL ONLINE RESERVATIONS CONSIDERED REQUESTS SUBJECT TO APPROVAL.)You'll enjoy spectacular ocean and Diamond Head views from both sides of this luxurious 2-bedroom, 2-bath condo on one of the uppermost, ocean-facing floors of the...
Magnificent Golf Course and Ocean Views -Hualalai Resort -18th Green- Golf Cart included
Magnificent Garden Level Golf Villa 1101 enjoys golf course and water views from this highly desirable location at Hualalai Resort. From sunrise to sunset unwind on the spacious lanai- gazing at the verdant green golf course, with the beautiful blue ocean and sandy...
Beautiful Wailea Ekolu Townhouse- Spectacular View- Your Perfect Maui Get-Away
Welcome to Happy Everything!10 Wailea Ekolu Complex!A premier, fully re-modeled, well appointed and comfortable 2-story townhouse situated on hole 10 of the famous Wailea Blue Golf Course at beautiful Wailea, Maui. Comfortably sleeps 6. Spectacular views of the Ocean...
Maui Resort Rentals: Kaanapali Alii 3114 – Luxuriously Upgraded 3BR Oceanview Penthouse!
This upgraded residence boasts gorgeous Pacific Ocean and lush West Maui Mountain views from its prime top-floor vantage point right at Kaanapali Point. Guests will enjoy views of the gorgeous turquoise-hued ocean from nearly every area of the home, including right from...
Ocean View Studio #264 - May 11-19, 2025 - Special
January 23 - January 28, 2026 $295 + tax p/n5 nights required** No Host Fee EVER **Located on pristine Kaanapali Beach, the Whaler is truly a spot of absolute paradise; no other description can suffice. The Whaler offers some of the best amenities, sounds, and views in...
Mauka Sunrise, Walk to Hau‘ula Beach & Trails, A/C
Welcome to our tranquil three-bedroom vacation retreat nestled in the heart of nature's paradise. Each bedroom boasts a comfortable queen bed, ensuring a restful night's sleep for everyone. The master bedroom features a convenient in-suite full bathroom with a...
Wailea Beach Villas E-302 on Wailea Beach
Modern living, in one of the best locations at Wailea Beach Villas, with outer island and sunset views that are unmatched. Centrally located in the complex, and only steps away to both pools on property as well as the white sand beach and Wailea Beach path, leading you...
Discount Week Rates! Elua Premier 2-Bedroom Front-Row... Oceanfront Unit!
Ulua Beach Premier 2-Bedroom Oceanfront Unit...Unobstructed Ocean Views!Welcome to Wailea Ulua #1002! This recently renovated luxury beachfront 2 bedroom/2 bath residence is located in the heart of Wailea on Maui Sunny South Shore. Within steps of the unit you are on...
Lulani House Beachfront Vacation Home in Haleiwa
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...
Cute and quaint little cottage on a homestead.
This quaint country cottage in Anahola sits on acreage surrounded by fruit trees and tropical foliage. If you are looking for an authentic local experience, this is it. Far from resort vibes, Banana Hideaway is as real Kaua'i as you can get. Wake up to incredible...
Alihi Lani 3 is a Luxury Condo with Amazing Views in a Prime Location.
You will love this Beautiful Ocean View! The fully equipped kitchen has everything you will need. There is plenty of beach gear for your Kauai outdoor adventures. Meticulously manicured landscaping and tropical flowers abound. For additional sleeping there is a queen...
Deluxe Top Floor Unit w/Ocean View-Maui Vista 2408
Premium upgrades, superior furnishings & charming decor make this condo a comfortable place to settle while on Maui. This vacation condo is so much more than just a place to sleep and cook, it will be your home away from home. Have breakfast on the lanai, take in the...
WOW!!! Great Winter Special Minutes from the Beach. NEW AC for your Perfect Stay
Top to bottom fully renovated 2 bdr 2 bath 1244 sq ft condominium in Maui Kamaole. Largest floor plan in the complex.Enjoy ocean views and the quiet location of our unit located in the D Cluster of Maui Kamaole. Tastefully decorated with all the amenities including...
'The Aloha Spirit ' Relaxing Retreat
We have remodeled our spacious one bedroom condo with amenities to be our home away from home. We invite you to make it yours while you enjoy the finest beaches and sunny weather of Kihei. Keep in touch with free wireless internet.Perfect for two people featuring a...
Now with optional car add-on
Car is a 2022 Tucson compact SUV, Special rate of $30 a day for cottage guests. After you book the cottage, Jordan's email will be shown and you can contact him for the details. You'll pick up the car in the parking across from baggage claim. No lines or paperwork...
Spectacular Views of Hanalei Bay and Bali Hai
Kauai’s Most Breathtaking Views at Hanalei Bay ResortWelcome to your Kauai paradise. Unit 9202 is located in the renowned Bamboo building which features the most stunning views of Hanalei Bay and Bali Hai. This large fully air conditioned 900 square foot, one bedroom...
Maui Resort Rentals: Luana Garden Villas 12C – Modern 3BR Villa at Kaanapali’s Newest Luxury Residences!
This luxurious brand-new 3Bedroom/3Bath residence is conveniently set within Enclave Two of the Luana Garden Villas. Its southern orientation offers a bright inviting setting for you and your ohana (family) and its designation within our "Elevated" collection at Luana...
Regency Villas 120 by Destination Kauai - Hale Maluhia Maikai, Central AC, Luxury Designer Condo
E komo mai, welcome to Hale Maluhia Maika'i!Hale Maluhia Maikai is a luxurious greenbelt property in Regency Villas at Poipu Kai with central air conditioning on the sunny south shore of Kauai. Spacious and bright with two stories and an open loft with vaulted ceilings....
Ocean, Sunset, Pool, King's Luxury experience
Summary:Tucked away on a quiet cul-de-sac, this villa offers expansive ocean and sunset views. Nested on a 1/2 acre lot, refreshing pool, central A/C. Features: Vaulted ceilings, 10ft ceilings, TV & high end cotton linen in each bedroom. Open floor plan with large,...
Pohailani Paradise, AC, Ocean Views, Sunsets
Wake up to breathtaking ocean views with Molokai and Lanai on the horizon. From the lanai, watch sailboats glide, sea turtles swim, and whales breach in the distance (during whale season). Golden beaches, swaying palms, and vibrant rainbows create a picture-perfect...
Kona Reef F14 Oceanfront Luxury, Full AC, King
We want you to have a wonderful stay at our condo; therefore, we’d like to let you know about some upcoming construction/maintenance work at the Kona Reef complex.Complex-Wide Work: Kona Reef complex will undergo concrete structure and resurfacing repairs from January...
Convenient Location in Waikoloa Beach Resort, Big Island, Hawai'i
• Unique, 8pm(!) check-out time eases red-eye flying• Very convenient Kohala Coast location• 12-minute drive to pristine Pacific Ocean beaches• 14-minute walk to A-Bay Beach 1.0 mile away• 5-minute walk to restaurants, grocery store, shops• Very clean,...
New Island-Inspired 2BD Oceanfront ~ Hololani B301
Welcome to Hololani B301, a stunning oceanfront retreat where comfort meets breathtaking views. This spacious two-bedroom, two-bathroom condo offers 1,066 sq. ft. of beautifully designed living space and easily accommodates up to six guests. This condo does not have air...
Ma'alaea Kai 110 - Spectacular Oceanfront PLUS Mountain View/Quiet Setting
Ease of access, pleasant tradewinds, quiet area and unmatched relaxation make this the ultimate in Maui locations. Ma'alaea Kai is a hidden gem that offers many amenities and views that travelers will treasure. Whether eating in or dining out, hiking the crater or...
Wailea Elua 1304 - Spectacular Oceanfront Condo with Panoramic Views
Wailea Elua #1304 – Oceanfront Comfort in the Heart of Wailea’s Resort CommunityWelcome to Wailea Elua #1304, a beautifully appointed 2-bedroom, 2-bathroom oceanfront condo offering the perfect blend of luxury and relaxation. Nestled in one of Wailea’s most...
Kihei Surfside #304: Spectacular Oceanfront Retreat with Unforgettable Views
Experience the perfect Maui escape at Kihei Surfside #304—an oceanfront retreat offering unforgettable views and coastal comfort. Just steps from Keawakapu Beach, this updated one-bedroom, one-and-a-half-bathroom condo captures the essence of island living with...
Lae Nani 312, Oceanfront, AC,Tropical Bliss, Steps to Beach and Town
Lae Nani Resort Kaua'i #312, Beautiful Oceanfront Unit on a Tropical Beachfront Oasis. This Kauai Vacation Rental is conveniently located in Kapaa Town within walking distance to shops, restaurants, and just steps to beautiful sandy beaches. Accommodates up to 4 guests,...
Ma'alaea Surf, Unit A4-2 BR Ground Floor Beachfront Condo, AC, Wi-Fi, Pool
Ma'alaea Surf, Unit A4 - Just steps from one of Maui’s longest white sand beaches, newly remodeled A4 has all the amenities of a luxury resort. Centrally located between the tourist's centers of Lahaina/Kapalua and Wailea/Makena, but once you’ve settled in your...
NEW! Village Manor D21, Distant Ocean Views, Walk to Kapaa Town and Beach
Village Manor Beach Side Apartment #D21. Waipouli, Kapa'a, Kaua`i Vacation Rental with distant ocean views and coconut grove views. Accommodates up to 4 guests, including children and infants.Second floor (top floor), walk up end unit apartment. Centrally located on...
Luxury Kapalua Golf Villa 14P1-2 w/ Golf Views, Lanai & Pools
Welcome to Kapalua Golf Villas 14P1-2, a serene two-bedroom, two-bath villa by Gather. Set within Maui’s prestigious Kapalua Resort, this ground-level retreat blends modern comfort with island ease. Accommodating up to six guests, it overlooks the emerald fairways of...
Poipu Oceanfront Dream Getaway at Kuhio Shores! 30 feet from the waters edge!!!
Hawaii Tax ID# TA-034-303-5904-01 and GE-034-303-5904-01New! Air Conditioning!Thirty feet from the waters edge, our spectacular oceanfront, ground floor, one bedroom, Poipu condo, has fantastic snorkeling, famous surf spots, and incredible sunsets. Everything you desire...
Lush Private Tropical Estate, Epic Views w/ Salt Water Pool & Spa
Nestled on an acre of private and quiet lush tropical grounds with heated pool and hot tub, Heart of Hualalai is your dream home, away from home, in Kona coffee country.Heart of Hualalai is a peaceful space where natural beauty and serenity meet mindful architectural...
Third-floor condo in town with ocean view, lanai & pool - walk everywhere
Kalanikai 321Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Wake up each morning to a gorgeous view of Kona Town, rustling palms, and the sparkling ocean horizon at this third-floor...
Close to Kahala Beach/Air Conditioning/Heated Pool/Clean/Quiet Neighborhood
Ask owner about available dates/rates. Elegantly remodeled in 2018, this one level, very clean, 4 bedroom & 3 bath home, has 2 master suites, a gourmet kitchen, air conditioning in every bedroom & high end finishes throughout this private oasis. Please inquire about...
Walk to Dtwn Hilo: Updated Getaway Near Hiking!
2 Mi to Beach | Community Pool & Laundry Facilities | Day Trip to Volcanoes Nat’l ParkEscape to your next Big Island base, just a mile from vibrant Downtown Hilo, lush waterfalls, and black sand beaches! This 2-bedroom, 1-bathroom vacation rental condo features...
Cozy Pineapple Studio 2 Blocks From The Ocean
This cozy and clean Pineapple Studio is located 2 blocks from the beach and Ali'i drive where all the best attractions are such as tasty restaurants, fun retail shops, bars, coffee and smoothie spots, fresh farmers markets, Magic Sands Beach, and much more. The...
🏖️Ocean Front Villa| Concierge Included | Central AC | vrKCV
vrKCV - Royal Sea Cliff 109, Professionally Managed by Kona Coast VacationsWelcome to Your Luxury Oceanfront Getaway!This stunning 1,900-square-foot villa is an oceanfront paradise, perfect for those seeking relaxation and adventure. Just steps from the ocean, this...
Ultimate Ocean View Villa • Pool • Pickleball • Game Room • Gym • Club Access
**December 21 - January 4 is now available at 20% Off!** The Kanini Estate is a recently constructed, beautifully furnished luxury villa in Waikoloa's premier oceanfront community of "Naupaka at Waikoloa." The Estate is located within walking distance of The Kings’...
Fleetwood Villa - Stunning Gated Home with Pool & Spa in Napili
Welcome to the former home of a legendary celebrity rockstar. The Fleetwood Villa exudes a zen-like ambience of calm alongside contemporary flair and function. Located in the Napili area of Maui, you will find a variety of beautiful beaches and restaurants within...
Breathtaking Ocean Views! Plan your getaway today!
Breathtaking Ocean Views! Plan your getaway today!2 bedroom 2 bath townhome in beautiful Mauna Lani PointRegarded as one of the most coveted locations in the ONLY oceanfront condominium community in Mauna Lani, you quickly appreciate the vantage point of being on the...
NEW PROMO! Ocean & Golf Views | AC | Lanai
Welcome to Living on Island Time — your private retreat on the Kona Country Club Golf Course with sweeping ocean and fairway views. Watch sunsets over the Pacific right from your lanai, just minutes from beaches, snorkeling, and Keauhou Bay adventures.🏝️ The...
Luxurious corner condo, totally updated Stunning views on wrap around lanai !!
This condo is our home away from home! This unit is personally managed by us to ensure you get the best possible service during your vacation. Please contact us if you have any questions not addressed in description. In compliance with the new laws in Hawaii, this unit...