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 Luxury Home with Beach Access and Private Pool - 5 bed/5 bath
Perfect for Families and Large Groups!Overlooking the dramatic Kona Coast, an oceanfront Oasis; sits Mele Kai — a luxurious island sanctuary welcoming guests in search of unforgettable memories and warm Hawaiian hospitality on Hawaii’s Big Island. Oceanfront suites...
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...
New Luxury Home in Nohea w/ Private Pool Spa and Two Ohanas
Step into refined island living with Abita Luxury Rentals at this 3,000 sq ft, 4-bedroom home built in 2023 in Nohea at Mauna Lani. Combining sophistication and comfort, this private retreat features a private pool and spa nestled among tropical landscaping along the...
F207 Spectacular Ocean Views - Beautifully Renovated Condo - 2 New Pools
We are pleased to announce that Makena Surf has completely renovated the South Pool! This beautiful new space is a welcome addition to the paradise we call Makena Surf!This beautiful Makena Surf condo provides the best that Maui has to offer. High end furnishings and...
Sandy Beach Front Property - Family Friendly - 4 min stroll to H2O - Ocean Views
Escape to paradise to our family friendly beach front property, Wailea Ekahi Villas unit 35B. 35B is a luxurious 2-bedroom, 3-bathroom 2 story condo (nobody above you!) and only a 4-minute walk down a gentle slope to Keawakapu Beach, a mile-long stretch of pristine...
Hilo Lagoon Retreat – 2BR w/View, A/C, Pool
Relax and Unwind at Hilo Lagoon CenterWelcome to your home away from home in the heart of Hilo! This spacious 2-bedroom, 2-bathroom condo offers comfort, convenience, and beautiful views of the peaceful waters at Wailoa River State Park.The spaceInside, you’ll...
🏖️New Listing! | Beautiful Townhome | Great Location | Concierge Included!
vrKCV - Kulalani at Mauna Lani 205 - Professionally managed by Kona Coast VacationsSecluded Kulalani Villa in the Mauna Lani ResortYour perfect vacation in a tranquil tropical oasis! Kulalani at Mauna Lani is a private gated community of quiet luxury townhomes,...
4BR Bali Inspired Luxury Home in Kukuiula
Hale Kahakai is a stunning four-bedroom luxury vacation rental in the highly desirable Kukuiula neighborhood in Poipu. Inspired by the villas in Bali, you'll admire every thoughtful detail put into this luxury home, from the latticework carved gates to vaulted ceilings...
Oceanfront Living at Luxurious Mermaid Manor in Kailua-Kona, Hawaii
Mermaid Manor – Oceanfront Island Home with Tidepools & Signature Indoor/Outdoor Mermaid ShowerWelcome to Mermaid Manor, your private oceanfront retreat in the heart of Kailua-Kona. This 2,500 sq. ft. island-style home features panoramic ocean views, three...
Kauai Oceanfront Condo Princeville, Pali Ke Kua 218, Best views, End unit
Beautiful Princeville Pali Ke Kua condo perched on a cliff overlooking Bali Hai, with unobstructed views of the ocean, sunsets, waterfalls, and rainbows. Turtles can be seen swimming in the cove below. December through April whales can be seen on their journey to and...
Direct Beachfront Spectacular Ocean Views Fully Renovated!!
Imagine the thrill of expansive direct ocean views from every room and the covered lanai! Kihei Kai 9 is the only true beachfront penthouse or top floor condominium in boutique Kihei Kai. Drift to sleep serenaded by lapping waves.This fully remodeled one bedroom pampers...
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...
Ekahi 38-A Luxury and Grace Located in Sunny South Maui
The Quiet Luxury and Attention to Detail Will Give You the Sense That You Have Arrived Home. Our Unit is Air-conditioned With a Master Bedroom / Bath Suite That Includes a New Serta King Mattresss With 1000 Count Prima Linens, Fluffy Bath Towls for the Bath and a...
Kaanapali Alii | 322
Welcome to Kaanapali Alii 322, your luxury vacation rental in Maui, where understated elegance meets the beauty of tropical paradise. This stunning residence offers refreshing views of lush gardens, creating a serene backdrop for your Hawaiian getaway. The elegantly...
6BR/6BA Luxury Villa w Pool, A/C, Walk to Beach!
Perfect for large families, wedding groups, or multigenerational getaways, this setup offers two side-by-side first-floor villas in Po‘ipu’s newest luxury complex—just a 5-minute walk to top-rated beaches and the Grand Hyatt. With 6 bedrooms, 6 full bathrooms, 2...
LUXURY VILLA - 3BR/3BA with Pool & A/C - Short Walk to Beaches
Welcome to Sugar Sands Villas!Luxurious and spacious (1600+ sqft) 3 bedroom 3 full bathroom villa with central A/C (rare in Poipu), fully-stocked gourmet kitchen and folding glass doors that open to a private lanai with lush views of the Po'ipu Greenbelt. Walk to...
🏖️Easy Walk to Village | Air-Conditioning | Ocean View | WIFI | vrKCV
vrKCV - Kona Pacific D622, Professionally Managed by Kona Coast VacationsWelcome to Our Home on the Big IslandAloha and welcome to our home on the Big Island, a place of wonder, diversity, friendship, and beauty. As our guests, please relax and enjoy everything that our...
Wailea Elua Village 910 - 1 Bedroom Garden View Condo
Wailea Elua Village 910 is a stunning one-bedroom, one-bathroom vacation rental located in the exclusive Wailea community on Maui. This beautifully remodeled condo offers a luxurious retreat a short stroll to one of the best snorkeling beaches on Maui. Located on the...
Stunning Kona home with salt water pool will take your breath away
Floor to ceiling window walls retract completely to let you take in the view of the serene Pacific, and enjoy true indoor-outdoor living. Relax by the salt-water pool surrounded by tropical plants and flowers. Pick fresh papayas, citrus and passionfruit (lilikoi) from...
Foster Tower Waikiki Beach Condo
Foster Tower is located steps away from beautiful Waikiki Beach. This is a one-bedroom unit in a highly desirable building and location. Enjoy beautiful ocean views and immediate access to the beach for surfing, swimming, and snorkeling, hundreds of restaurants, the...
🏖️Luxury Island Oasis | Spectacular Ocean Views & Pool | vrKCV
vrKCV - Aloha Place, Professionally Managed by Kona Coast VacationsAloha Place – Luxurious 3-Bedroom, 3-Bathroom Home with Spectacular Ocean ViewsExperience the ultimate in luxury and tranquility at Aloha Place, a Bali-inspired retreat perched in the serene upper Kona...
Marriott's Ko Olina Beach Club 2 BR Oceanview Villa
Just half an hour from Honolulu, Ko Olina Beach Club is nestled among the lush grounds of Ko Olina Resort & Marina, a picturesque 640-acre community built along a pristine stretch of the Oahu coastline. Situated in the stunning southwest region of Kapolei with...
Beautiful "Beachfront" House on the Beach at Sunset Beach Paradise on the Beach
A Truly Luxury Beachfront House Located on World Famous Sunset Beach on Oahu's North Shore. Named 'Paradise on the Beach' at Sunset Beach by many guests this premier Direct Beachfront two-story, two large bedrooms, three full baths, executive style house affords the...
Ko Olina Beach Villas B901: Luxe 3BR Penthouse w/ Beachfront Views
Welcome to Ko Olina Beach Villas B901 by Gather, a luxurious penthouse in the heart of the Ko Olina Resort. This exclusive ninth-floor beachfront vacation rental offers breathtaking ocean and pool views, providing an unparalleled experience for those seeking a tranquil...
Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui
The Hamoa Bay Bungalow is HANA MAU'Is most charming vacation hide-away. Balinese inspired, private, with partial ocean views, secluded and romantic. Just beyond sleepy Hana Town... this property is tucked in amongst lush ferns, banana trees, bamboo, colorful heliconias,...
Direct Ocean Front Property Wailea Ekahi 16A 2 Bed 2 Full Bath Ocean Views 5star
Wailea Ekahi Villas Unit 16A: 2 Bed, 2 Full Bath, Sleeps 6 (We have over 50 five-star reviews!)Book our unit with confidence! Wailea Ekahi 16A is the perfect getaway for young families or couples seeking a quiet, luxurious escape on an ocean front property in the heart...
Makahuena 1202. Partial Ocean View, 2 bed, 2 bath with AC. Poipu.
Located on the southern most point of Kauai, right between Poipu Beach State Park and Shipwreck Beach. Partial ocean view. Nicely remodeled 2 bedroom, 2 bath condo with Lanai. Master bedroom has a king bed, 2nd bedroom has 2 twin beds that can be moved together for a...
Beach-AC-Pool-Gym-Oceanview-Garden-two lanais-212, Spectacular View w/ W/D and AC
Relax! Condo on Kiahuna Beach! Updated Stone Countertops, cabinets, and open concept! This amazing oceanview Kiahuna condo with AC overlooking the garden/lagoon on the most beautiful resort grounds on the south shore has plenty of space for the whole family! The...
Hawaiian*Elegance*FULLY REMODELED OCEANVIEW 2 Bdrm
Indulge in the epitome of Hawaiian luxury within this impeccably renovated condominium. Immerse yourself in the tasteful Hawaiian decor that effortlessly transports you to paradise. The well-appointed interior boasts high-end furnishings and comprehensive amenities for...
Maui Resort Rentals: Honua Kai Hokulani 546 - Spacious 2BR w/ Partial Ocean & Mountain Views!
Perfectly positioned to provide guests with the ideal combination of Maui scenery, Hokulani 546 showcases gorgeous views of both the blue Pacific Ocean and the lush West Maui Mountains. With over 1100 sq ft of luxurious living interior, this spacious two-bedroom suite...
❤️PiH❤️ BIG ISLAND OASIS ★ Family Oasis★Free Hilton Passes ★ Bikes & Ping Pong★
Big Island Oasis brought to you by Paradise in Hawaii Luxury HomesWelcome to our 4 bedroom Big Island Oasis at KaMilo, on the Big Island of Hawaii\Big Island is such a wonderful place to spend with your friends and family, children and grandchildren. Vacations create...
99 Steps to the Sand - Ground Floor 3 Bedroom - Hokulani 104
This condo is zoned hotel and is in legal compliance with all Maui County ordinancesGround-Floor Oceanfront Suite and Wraparound Lanai at Honua KaiE komo mai (welcome) to Kai Hele Ku ("The Quickest Way to the Ocean"), where the warm embrace of Maui's kai (sea) and the...
Beautiful Pacific Shores Condo 2BR, 2BA Full A/C & ready for your Maui visit!
This VRBO listing is a fully renovated and very well furnished and equipped condo located in the Pacific Shores complex in the heart of South Kihei, Maui. It is just steps away from wonderful beaches, restaurants, and shopping.The unit includes two bedrooms (each with...
MARRIOTT WAIKOLOA OCEAN CLUB, Top Rated Resort On The Big Island!
Please choose a Friday, Saturday, or Sunday check-in and enjoy a seven or night stay. If you need larger accommodations, ask our agent about our two bedroom option. Thank you for your interest in booking with DashWeek/ Dash Realty Group, Windermere Florida. Dash Realty...
Ilikai 824
Top-of-the-line modern, high-end designer remodel. The direct ocean view will greet you as soon as you open the door! This studio unit boasts a unique feature of separation doors that create a one bedroom atmosphere. The open floor plan sweeps from the full size...
Ilikai 30-Day Rental in Waikiki
This rental is on the 19th floor of the Ilikai Hotel with direct lagoon and ocean views. This 1 bedroom apartment has been remodeled into a large 500 sq ft studio and is gorgeous! High-end materials were used throughout the apartment. We used beautiful flooring in the...
Luxurious Tropical Retreat Wailea Ekahi Unit - 31 D
Luxurious Tropical Retreat - Unit 31D is truly "one-of-kind"!Ideally located overlooking the lower Ekahi Village, Unit 31D provides our guests with the best of everything Maui has to offer: spectacular views, privacy and a short stroll to the beach and main pool.With...
Exquisite on Paradise*Fully Upgraded with Ocean Views!
This freshly renovated condo offers stunning ocean views and a large, airy lanai with comfortable outdoor seating. Pack up the cooler and head to the beach or lounge by the pool and soak up the serenity that is Kauhale Makai.This roomy condo is just steps from the...
Villa Moana - Beachfront Perfection
Spacious Luxury Beachfront Private Villa - 8 BR - 3,850 Sq. Ft. - Newly Built. Right on the beach in Kihei. Hosted with aloha and professionalism. Locally owned and operated. If you need more or fewer bedrooms, please send us a note and we can offer a customized rate....
Wailea Ekahi 33c Ocean View Condo - 500 Feet from the Beach!
Welcome to this Wailea Ekahi Condo (Unit 33C -LINKS TO OUR PERSONAL WEBSITE ARE LOCATED BELOW). Our one bedroom, one bath ocean view unit is located within Wailea Ekahi Village, one of South Maui's premiere oceanfront resort developments. Situated on the central...
Magic Skies B&B Main Floor Living 2300 sq ft, 3 bed, 3 bath Panoramic Ocean View
Enjoy the entire 2,300 sq ft level to yourselves, with panoramic views, wrap around lanai, full chefs kitchen, laundry, open concept living, dining, 3 bedrooms, 4 beds, 3 full bathrooms, with access to hot tub, game room. With specialty wood work throughout hand crafted...
Hale Hina ~ Private, Peaceful, Perfection!
Welcome to Hale Hina - The Home of the Hawaiian Goddess of Sunrises, Sunsets, Coral Reefs, and the Moon! Our home is very special, and has many fabulous features and amenities, including the most important and maybe the most intangible one: Hale Hina is our vacation...
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...
Mauna Lani - Luxury 4 Bedroom Home - Sleeps 10
4 Bedrooms, 3.5 Baths (Sleeps 10)This 4 bedroom, 2100 square foot home, comfortably sleeps 10 and is located within the KaMilo community which is part of the world class resort of Mauna Lani! Mauna Lani is on the beautiful Kohala Coast on the Big Island of Hawaii. The...
Waipio's Enchanted and Private Hideaway Pool, Slide, Hot tub & Spectacular Views
Waipio Heaven – Cliffside Luxury Estate with Ocean Views, Pool, & OrchardLocation: Hamakua Coast, Big Island, Hawaii Bedrooms: 4 | Bathrooms: 4.5 | Sleeps:** 10 Minimum Stay: 5 nightsProperty Overview:Discover Waipio Heaven, a private, luxury 4-bedroom estate nestled...
Whitewater and Anini Reef Ocean Views fully airconditioned
This recently- and completely-remodeled, sun-lit and spacious 2-bedroom, 2-bath condo at The Point at Alii Kai (Unit 5-302) welcomes your group to an unforgettable vacation in Princeville, where you'll face jaw-dropping, direct Pacific Ocean views on Kauai’s North...
NEWLY REMODELED! Beautiful & Spacious- Two Story Wailea Ocean View 2BR/2.5BA
Aloha! We are back on the rental market after a lengthy remodel! Enjoy beautiful ocean views while relaxing in our very spacious 2 story, 2 bedroom/2.5 bath Condo/Townhouse! Our end unit, #1702, has 1500 sq ft of living area, plus 400 sq ft of lanai/patio area. Great...
Beautiful Pili Mai 3E Condo A/C, Across From Pool
Summary:Experience the enchanting allure of Kauai in our 2-story, 3-bedroom, 2.5-bath condominium nestled along the scenic Kiahuna Golf Course in Poipu. Enjoy the breath-taking mountain views that surround this meticulously designed space. Our air-conditioned condo,...
Kamaole Sands 1-307 - Prime Location, Stunning Renovation, Large Lanai, New AC
Kamaole Sands 1-307 is a stunning second home for the new owners. This premium unit features an end unit location with stunning ocean views across the perfectly manicured lawn of Kamaole Sands. Completely remodeled from top to bottom, this one bedroom, two-bathroom...
❤️PiH❤️ Wahi Malu ★ Near Pools ★Fantastic Lani ★ 3 Full Bath ★
Brought to you by Paradise in Hawaii Luxury Homes.Welcome to Wahi Malu, a part of our Hawaiian Luxury Collection. Wahi Malu at KaMilo is a gorgeous 3 bedroom/ 3 bath home.This beautiful home is one of the newest KaMilo homes and is only a short stroll to the pools,...