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.
Marriott's Ko Olina Beach Club - Luxury 2 Bedroom Villa
Marriott’s Ko Olina Beach Club is situated on the beautiful Western shore of Oahu, where waterfalls and fountains welcome you as you drive under the port- cochere. Just 30 minutes from Honolulu, this beach front oasis is secluded and peaceful. Surrounded by seven...
Hale Ohana: Kailua Retreat w/hot tub, Tropical Pool, Walk to Beach
Set along Kailuana Loop on Oahu’s beautiful windward coastline, Hale Ohana by Gather offers a spacious, family-friendly retreat designed for easy island living. With nearly 3,000 square feet of indoor-outdoor space, a private pool and hot tub, and a dedicated guest wing...
Oceanview House near Best Beaches on Big Island, Massage Chair!
This house, called Hale ‘Uhane, (House of the Higher Self), is located in beautiful Kawaihae Village, near Hapuna Beach. The 3-bedroom hale boasts a very short drive to a variety of world famous and award-winning beaches. Along with the best beaches in Hawaii, there are...
Beautiful, Family Friendly 2 Br 2Ba Across Street From Beach.
Beautiful 2 bedroom 3 bed unit offers a quiet getaway and island view. Newly updated furniture and decor. Each building has a pool, tennis courts and barbecues. Quick stroll across the street to Beautiful Charley Young Beach. Great Shopping and dining options are a...
House close to beach, North Shore, Oahu
Located on the countryside of Oahu between the ocean & the mountains, you will be in the perfect spot to experience what Oahu has to offer.Close to world famous North Shore, Turtle Bay Resort, popular surf breaks, snorkeling spots, sea turtles, & much more!Only 2 min....
Ainamalu 11 – My Favorite Island in the Sun: Waikoloa 3BR Retreat with Lap Pool
vrKCV - Ainamalu 11 - My Favorite Island in the Sun, Professionally Managed by Kona Coast VacationsWelcome to My Favorite Island in the Sun!Escape to this expansive, single-level 3-bedroom oasis, ideal for families, friends, and athletes alike. “My Favorite Island in...
Alii Kai 2 BR Condo - Hawaiiana Style Walkout Unit
Sit back and relax in this 2 bedroom/2 bath desirable Alii Kai walk out, end unit condo. Situated ideally to feel like your own private oasis with no obstructions of your oceanfront view. Enjoy breathtaking ocean views from every bedroom, the kitchen and living room!...
Executive Balinese Vacation Home in Hawaii Kai
Find serenity,luxurious style, at Hale Maluhia. This Oahu vacation rental, whose Hawaiian name translates to "house of tranquility," is a beautifully contemporary resort close to some of the island's best beaches and east oahu coastline. Invite up to eight friends or...
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...
Beautiful Penthouse Condo w/ Direct Ocean Views - Sleeps 8!
Aloha! This condo has everything you'll need for an amazing Hawaiian vacation! We selected this condo because we love the layout and the ability to comfortably sleep 8 people. Also, the grounds at the Papakea Resort are immaculately maintained and have something for...
Beautiful, large studio with Mountain views from deck, beach access & A/C
This is a large studio, "The Mountain Suite" resides within a triplex building on the edge of a cliff over Anini beach on the North shore of Kauai! Complete with kitchenette, separate bathroom, partial ocean views and The Napali coast. This is a great place for a couple...
Ilikai Hotel & Luxury Suites JRCV-2: Luxury Studio w/City Views
**PROPERTY PROJECT**Ilikai Hotel Spalling and Exterior Painting ProjectAn exterior painting and spalling repair project to enhance the building’s structural integrity and appearance with minimal disruption will commence on August 18, 2025. Work Schedule: 9 AM – 5 PM,...
"Sea World" at Your Feet + Casual Elegance + Absolute Privacy = Whales Play
Wonderful experiences await your arrival at Whales Play, a secluded and tranquil retreat. Take in the panoramic views while lounging on the upper lanai, watching whales and dolphins at play. Savor a lingering sunset and then be dazzled by the starriest night sky from...
Beautiful Secluded Hanalei Home One Block to Beach at Magnificent Hanalei Bay
TVRNC Permit #1020The Hibiscus is a beautiful 3BR 2BA Hawaiian-style home just one block from the stunning two-mile crescent beach at world-renowned Hanalei Bay.The furnishings, amenities, and setting make it a wonderful vacation home from which to enjoy the wonders of...
Luxurious, Remodeled Mauna Lani Villages Townhome! VIP Beach Pass Included!
BEST KEPT SECRET IN MAUNA LANI - Mauna Lani Villages 329 is a modern, highly renovated three bedroom townhome located right in the middle of the exclusive Mauna Lani Resort, where guests are able to access private beach clubs, secluded oceanfront trails and restaurants...
Beach Glam @ Turtle Bay - Kuilima Estates West
We are all looking for a quiet, restful, safe place to de-stress and forget the troubles of the world. As a Hawaii born and raised local, there are few places that can rival this task than the North Shore on Oahu. With 24 hr security, free parking, and the Turtle Bay...
Hale Kai #116 Oceanfront Condo, just steps to the beach, pool and BBQ!
Fully remodeled first floor direct oceanfront condo, just steps from the pool, beach, and BBQ. The Hale Kai has a small quiet feel, that has guests returning year after year, "Hale Kai", your home by the sea. Experience amazing views of Molokai and Lanai and enjoy...
Luxury Beachfront Home in Haena
Makana Akua is approximately 1,700 square feet with over 1,000 square feet of decks. Beachfront near Tunnels Beach and Tunnels Reef in Haena, it is truly a tropical rainforest. This home offers two master suites with private granite bathrooms, king beds, and individual...
New Luxury 5BR Princeville Estate with Pool
This Luxury Pool & Spa Estate has it all! Panoramic Views of Hanalei Bay, Lumahai Beach, Bali Hai, Mountains, Waterfalls, Rainbows, backing to hundreds of tropical acres and fruit trees! 5 Bedrooms, 5.5 Baths, Separate Living Room with 85" HDTV, Fully Equipped Gourmet...
Perfect family home with A/C! Amazing location, a short walk to Poipu beaches!
This private ranch-style home is located in the Lanai Villas section of Poipu Kai Resort. What makes this house special is the enclosed tropical backyard with a gate that leads out to a secluded greenbelt path for a short walk to Grand Hyatt, Shipwreck Beach and the...
Beachfront Haena home with A/C - Near Tunnels Beach
This modern beachfront home was recently fully renovated. Hale Ekahi (One) is one of two properties on this beachfront lot. Ekahi offers modern beach furnishings to fill this luxurious beachfront home. The home has 3 bedrooms, 2.5 bathrooms, a fully equipped gourmet...
4 Bedroom with Private Pool and Spa in Waikoloa Beach
Welcome to Ainamalu Breeze, where mainland cares and day-to-day worries are carried away to provide you the sanctuary you have desired. When you enter our exquisite property, you leave the mundane tasks of travel and are released into a world of luxury. Upon entering...
Relaxing garden setting with ocean view A210
Watch the life of Maui unfold from the morning till evening from your private 114 sq foot private view deck. Premium condo suite located near the pool area. Second floor means easy access to tropical gardens and the ocean beyond. Quiet location features large private...
*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. It’s...
In the Action! Ground floor steps to ocean view pool
Located near the pool area, easy access to BBQ's, pool and beach. Watch the life of Maui unfold from the morning till evening from your private 114 sq foot private patio. Condo has a dedicated free wi-fi internet router providing high speed internet for those who wish...
Maui Sunset A111, ground floor paradise
Watch the life of Maui unfold from the morning till evening from your private 114 sq foot private view deck. Maui Sunset A111, ground floor paradiseGround floor means easy access to tropical gardens and the ocean beyond. Quiet location features large private view deck...
Cant get any closer to the OCEAN!
Completely Renovated 3-bedroom Oceanfront at Menehune Shores with A/C The view doesn't get any better than this!! Pack your suit...Menehune 518 has everything else you'll need to enjoy your Maui vacation! This beautifully renovated upscale unit is located in South Kihei...
Panoramic Breathtaking Ocean-Sunset-Bali Hai Views, A/C + Surf Crashing Below!
2026 Discounted Rates!**Book 7 consecutive nights or more through April 30, 2026 and receive 10% off your nightly rate**Welcome to Hale `Ikena Kai ("home of mystical ocean") at Pali Ke Kua, a unique home vacation experience on Kauai’s stunning North Shore! This intimate...
Fab Ocean View, largest 1 Bedroom Premium Villa!
Ignite your senses with warm, sunny beach days and dazzling sunsets! Ocean View, Beautiful 1 Bedroom, 1 Bath Premium largest size villa at 900 sq ft, sleeps 4. Parking $35 per day.Full Resort Access. On one of the world's most beautiful beaches!The Westin Kā‘anapali...
Beachfront Platinum Condo, updated. Gorgeous Ocean & Crater Views. Makena Surf.
Building B is the premier beachfront building at Makena Surf, set among lush tropical gardens. From our condo (B202), gaze endlessly at the ocean, watch the whales breach (seasonal), experience magical sun sets, step onto the beach to swim or snorkel with the turtles or...
Beautiful 2 Bedroom / 2 Bath / Sleeps 6
The beautiful home is located on the east side of Oahu in Hawaii Kai. Located near beaches such as the famous Hanauma Bay, restaurants, shopping centers,hiking trails, scenic lookouts and water sports. The home offers 2 bedrooms (2 queen beds), 1 sofa bed and 2...
Edge of Cliff Luxury Penthouse over Largest Coral Reef in Hawaii - Beach Access & AC
Very large penthouse with 2, 000+ square feet of living space under roof, vaulted ceilings and the most incredible views over the largest coral reef in the State of Hawaii. Ocean views available throughout the condo's living area and into the huge master bedroom suite....
Romantic, Luxury Condo with Spectacular Ocean Views
1 BR, 2 BA condo. Close to beach, golf, tennis, restaurants, and shopping.Aloha. We are excited to be the owners of this very special condo. We have been coming to Maui for over 25 years, and we love the magic that this island has had in our relationship. With this...
❤️PiH❤️ The Oasis at Kulalani ★ Tons of Extras ★ Near Pools ★ Bikes ★
Brought to you by Paradise in Hawaii Luxury Homes.Welcome to 'The Oasis at Kulalani' on the Big Island of Hawaii.Welcome to the newest home in our Hawaiian Luxury Collection. 'The Oasis at Kulalani' is a wonderful almost new exquisite 3 bedroom home in the gated...
❤️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...
Lokomaika'i Kailua: Elegant Vacation Home with Pool & AC
On Oahu’s sun-kissed Windward side, Lokomaika’i Kailua (meaning “Gracious Kailua”) invites you to slow down, open the sliding glass walls, and let the island breeze transform everyday living into something magical. This single-level home blends open-concept interiors,...
Nalu Bliss- Amazing 2BR Waterfront Location on Alii Dr Close to Town and Beaches
Updated 2 BR 2nd floor Condo in small 16 unit development overlooking the pacific with amazing sunset views!! We purchased the condo in June, and it was a very active VRBO with a 4.8 rating and more than 40 reviews!! We have made a number of upgrades since purchasing...
Kauai Exclusive - Lae Nani 121 - Oceanfront - Steps to the beach
Enjoy an amazing 180-degree view of the ocean overlooking Wailua Bay, a wonderful sandy beach and beautiful green mountains in the background. Your stay here puts you just steps away from the water and on one of the few swimmable beaches on the East side. This unique...
Live da HI life with views of the ocean and steps to the beach
Ho'onanea is a 5star experience on Maui's South Shore.Take the convenient elevator to this third-floor residence with partial lanai views of both Haleakala and the ocean. Start each day with a cup of Maui coffee and sunrise on the lanai and end with a beautiful sunset,...
Maui Stunning Beachfront Luxury Ground Floor with A/C. *Nani Kai Hale 101*
Stunning luxury, ground floor condo directly on Sugar Beach, one of Maui's best beaches. The unit was completely remodeled floor to ceiling in 2017 and includes 2 bedrooms (2 king beds in each bedroom) each with en-suite bathrooms, a full luxury kitchen, living area...
Turtle Bay Hideaway - Kuilima Estates East
Our Turtle Bay Hideaway is the perfect place for your Hawaiian getaway! Enjoy 5 miles+ of secluded beaches, 2 private swimming pools, 2 private tennis courts, 2 PGA golf courses, horseback riding, surfing, snorkeling, diving, fishing, activity rentals and fine dining...
VIEWS VIEWS VIEWS with AC! Large Beautiful on Golf Course
** Please note there is ongoing construction within the complex** Emmalani Court Unit #110 is the only 3 bedroom condo with AC on the cliff in Princeville! You will notice the absolutely amazing views as soon as you walk in. This peaceful location allows ocean views...
Gorgeous House Next Door to 1Hotel Hanalei Bay - Awesome Views Unit #10
*Please review the current quarantine requirements on Kauai at: https://www.kauai.gov/covid-19 before booking.Hanalei Bay Villas #10 - Look no further - 'Paradise Found' So whether you are honeymooning or just looking for a very well deserved vacation you are always...
🏖️Ocean & Golf Course Views | 2 Bdrm with Loft | AC | vrKCV
vrKCV - Country Club Villas 334, Professionally Managed by Kona Coast VacationsWelcome to Country Club Villas #334 – Oceanview Golf Course Condo with Spectacular Sunsets! Experience the magic of island living at Country Club Villas #334, a beautifully remodeled...
Kailua-Kona Luxury Vacation Home – Ultra Private Oceanfront Gated Estate
This oceanfront residence is a gated estate situated in a private neighborhood off of Kailua-Kona’s scenic Ali’i Drive, just 5 minutes from town. Recently remodeled, this home reflects a true sense of place with Hawaii-style architecture, expansive indoor-outdoor living...
New! Maui Eldorado J121, Amazing Ocean View, #1 Kaanapali Beach, Prime Location
Amazing ocean view! Our beautifully remodeled studio suite is located right in the heart of Kaanapali and is center to an incredible ocean view surrounded by lush tropical grounds. Feel the Aloha of the island as you gaze at the ocean and watch yet another stunning...
Kolea 10B ~ The Heart of Kolea with Unforgettable Ocean Views
Welcome to Kolea 10B – $100 Lava Lava Beach Gift Card Emailed to you on Arrival!Location, View, Perfection… Stay at one of the most desirable vacation rentals in Waikoloa Beach Resort with breathtaking ocean views on the Kohala Coast. Kolea 10B offers one of the best...
❤️PiH❤️ Sea to Sky ★ Newly Updated★ FREE Mauna Lani Tennis, Pickleball, Lap Pool incl
Brought to you by Paradise in Hawaii Luxury Homes.Welcome to Sea to Sky, a part of our Hawaiian Luxury Collection. Sea to Sky, at the Mauna Lani Villages is a wonderful 3 bedroom home with luxurious high end finishes in a premier resort community. This is one of a very...
❤️PiH❤️ PARADISE AWAITS ★ Private Pool & Spa ★ Guest Cottage
Brought to you by Paradise in Hawaii Luxury Homes.Welcome to Paradise Awaits, a part of our Hawaiian Luxury Collection. Paradise Awaits at KaMilo is a wonderful, large, single-level 4 bedroom home that includes three bedrooms in the main house, each with a large primary...
Diamond Head Surf House: Gold Coast Oceanfront Home w/AC & Gorgeous Views
Completely immerse yourself in oceanfront island living at the stunning three-level retreat known as the HLH Team, a spacious 3BR luxury home positioned along Oahu’s coveted Gold Coast between Diamond Head and Waikiki. This monthly rental delivers panoramic shoreline...