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.
Luxury Ko Olina Beach Rental Panoramic Ocean View 3BR 3BA 8th floor 2 parking
Imagine yourself in a world-class Oahu, Hawaii oceanfront resort in Ko Olina beach rental bliss with exotic woods, natural stone and an expansive lanai. Imagine as you lie down on a bed of total luxury. You sink down into silky softness that cuddles you as you are swept...
🏖️NEW LISTING | Brand New Renovation! | Professionally Managed | vrKCV
vrKCV - Mauna Lani Fairways 1601, Professionally Managed by Kona Coast VacationsFeel the Aloha Spirit and relax in tropical paradise at Sandy Feet Retreat! Newly renovated in the summer of 2022, enjoy the modern Hawaiian vibe in this two-bedroom, two-bathroom townhome...
~ This Is Wailea Living ~
This is Wailea Living!Nestled in a private and secluded enclave between the Wailea Blue Course and the Wailea Tennis Club, the Wailea Grand Champions Villas are where travelers can golf, play tennis, be pampered at the Wailea Grand Spa, whale watch or turtle spot, or...
Happy Place Bungalow, 2-Minutes to the Beach! TVNC #4339
Hanalei Happy Place Bungalow Permitted Vacation Rental Property - TVNC#4339Transient vacation rental is located in the tsunami evacuation zoneCharming bungalow studio with jungle views close to the beach!Nestled between the verdant mountains and golden beaches of...
Hanalei Bay Villas #22 - a 2br / 2.5BA, mountain and golf course view condo
Hanalei Bay Villas #22 is a spacious two bedroom, two and a half bath, two story stand-alone condominium. With an additional queen size sleeper sofa, this unit sleeps six comfortably. Beach access is available past the 1 Hotel Hanalei Bay next door. Views include the...
Come spend some time at Our Kohala Ranch House!
From our covered lanai you have expansive views of the ocean, the sprawling Kohala ranchland and Haleakala on neighboring Maui. There really is no better way to start your day!And what you do with the rest of your day is completely up to you: Feeling a bit lazy? Relax...
Halii Kai 12H - 3 Bedroom Deluxe Ocean View Hali Kai Vacation Rental
Sit back, relax and enjoy the best view of the Waikoloa Beach Resort! The view from this villa is nothing short of breathtaking. From this villa you overlook the signature hole of the golf course and onto the blue waters of the Pacific Ocean. The view from this villa is...
Maui Resort Rentals: Honua Kai Hokulani 1034 – Expansive Top Floor Corner 2BR w/ Gorgeous Mountain Views!
Perched high above the palms on the top floor of the Honua Kai Resort, this exquisite 2-bedroom, 2-bathroom corner penthouse showcases stunning views of the lush West Maui Mountains, complemented by peekaboo glimpses of the sparkling blue Pacific.With nearly 1,300...
Ko Olina Beach Villas B103: Spacious Elegance & Oceanfront Views
Ko Olina Beach Villas B103 by Gather is the perfect ground-floor beachfront villa offering a breathtaking oceanfront getaway in the heart of Ko Olina. This three-bedroom, three-bath villa is the perfect blend of luxury and comfort, designed to provide an unforgettable...
Front Row Eclectic Updated Oceanview S Kihei 1 bedroom 1 bathroom condonn
Welcome to Maui Vista 1312. This eclectic updated partial oceanview 1 bedroom condo is located in the heart of South Kihei. This condo can accommodate 4 people & has everything needed to feel at home. Cross the street & end up at Charley Young beach which connects to...
Hale Laule'a - North Shore Oahu Estate. Walk to Sunset Beach!
**In compliance with Hawaii vacation rental laws, this property is held for your exclusive use for a period of 30 days or greater regardless of your actual length of stay. Please inquire for details or questions regarding pricing and availability. Total pricing for the...
Ocean View Studio at HBR, A/C Included
Don't miss this very special condo hotel room at the beautiful Hanalei Bay Resort! This unit sits in a unique private location with breathtaking views of Hanalei Bay, mountains, waterfalls and Bali Hai. It is one of the ONLY units at the resort with NO stairs, yet...
AlohaCation - Oceanfront Work and Family Time
Work from Paradise or Enjoy Family Time by the BeachImagine waking up to breathtaking ocean views, working remotely with the sound of waves in the background, or spending quality time with your little ones on a peaceful, safe beach. Our oceanfront apartment blends...
Includes Hilton Waikoloa Pool Pass for stays in 2025! Includes Golf Package.Wai
This vacation rental is professionally managed by ResorticaHawaiiWaikoloa Beach Villas E23Please scroll down for detailed informationHilton Pool Pass: Valid for stays through December 31, 2025. Maximum 6 persons per pass (children under the age of 5 are not counted...
Modern Renovated Maui Kamaole Condo Near Main Pool, Beach Across Street
***Summer Discounts now available for July and August 2025! 15% off plus an extra 5% for weekly rentals and 10% for monthly! Quote calculates the lower rates!***This 1050+ square foot 2BR/2BA condo is in the highly desired Maui Kamaole complex, one of the newer condo...
❤️🏖BEAUTIFUL LARGEST 1BD, OCEAN VIEW ONE OF THE CLOSEST TO OCEAN 120 REVIEWS❤️
🏖 LARGEST ONE BEDROOM WITH OUTSTANDING REVIEWS. UPDATED! Newly Painted interior and lanai. COMPARE OUR FLOOR PLATE TO SEE OUR LOCATION COMPARED TO OTHERS ON VRBO.🌺 You are renting directly from the owners. We would love to have you stay with us. As our guest, you...
Ocean Views/Private Swimming Pool. Mauna Kea High Bluffs Home
This vacation rental is professionally managed by ResorticaHawaiiMauna Kea High Bluffs #9. Stunning Private Home with swimming pool and ocean views. Mauna Kea Resort Amenity Program add on optionPlease scroll down for detailed informationPLEASE NOTE: There is ongoing...
New Remodeled Kuaui Escape! 1/1 condo in charming Kapaʻa with WiFi, AC
Welcome to our charming one-bedroom condo by the beach in the heart of Kapaa next door to Coconut Marketplace. This newly remodeled one-bedroom offers a fully equipped kitchen,a furnished lanai,a king-size bed, and a sofa sleeper that can accommodate up to four guests....
Hale Honu - 5 Star Oceanfront Home Overlooking Turtle Cove!
Perched above historic Koloa Landing, also known as Hanaka’ape Bay, Hale Honu boasts dominant bay and ocean views. Just off your private lanai is some of the best snorkeling and scuba diving the island has to offer. Giant sea turtles can be seen below swimming and...
BEAUTIFUL CONDO WITH AWESOME SUNSET VIEWS
Beautiful two bedroom two bath luxury condo. Kitchen with granite counter tops and all stainless steel appliances. Bathrooms with granite counter tops and beautifully tiled bath/showers. This condo is located in Maui Kamaole One of Kihei best first class resort...
nPrivate, Walk to Beach, Golf, Shopping and Restaurants!
Located in Waikoloa Beach Resort at Vista Waikoloa.. Beach, Golf, Snorkeling, Seasonal Whale Watching, Shopping, Restauants, all minutes away!Our beautiful ground-floor condo, on the sunny/dry side of the island, is located in the luxurious resort of Waikoloa Beach. We...
Kahala Oceanside – Coastal Sanctuary with Panoramic Views
Kahala Oceanside is a private paradise retreat that comfortably sleeps 14. This luxurious ocean front hideaway on the South Shore of Oahu, known for its spectacular sunsets, is just minutes away from fine eateries, world-famous hikes, and the endless attractions of...
Professionally designed and remodeled in 2021! 2 master bedrooms, spacious plan
2024: (2) New sofabeds!2021: Professionally designed and newly remodeled! No expense has been spared to make this a comfort. All brand new furniture, updated kitchen and baths, luxury bedding and mattresses, new W/D.2 master bedrooms with ensuite bathrooms separated by...
❤️PiH❤️ DREAMS COME TRUE ★ Private Pool and Spa ★ Golf Course View
Brought to you by Paradise in Hawaii Luxury Homes.Dreams Come True is a stunning home in the KaMilo community overlooking Mauna Lani North Course.We pride ourselves on providing some of the most sought after homes on the Kohala Coast. We have partnered with the owners...
Beautiful oceanfront condo 🏖 As oceanfront as you can get 🐳 Royal Sea Cliff 209
This 2,110 square foot luxury condo located at the Royal Sea Cliffs offers a one-of-a-kind 932 square foot lanai offering a panoramic ocean view! The lanai is equipped with outdoor dining, a queen-sized sunbed, and loungers offering many options to be out enjoying the...
Holy Kamaole! Beachfront Kihei!
** If this unit is already booked, check out our unit next door https://www.vrbo.com/9432451haLocation, Location, Location. Imagine fixing a meal while enjoying the sunset, or maybe watching the whales from our perfect beach front location on Kamaole One beach. This...
Hoolei Uni 31-2 Ocean view- ideal Wailea location walking to beaches and shops
Dramatic ocean views, this spacious town home is approximately 2500 sq ft of interior footage and 596 sq ft of lanai space. The Hoolei community is located directly across the street from the Four Seasons and the Grand Wailea Resort. Unit 31-2 has the a great location...
Hilo's Finest 2 bd Condo - Pool, A/C, Views!
Enjoy a stylish experience at this centrally-located condo. Far exceeds any Hilo Hotel. 2brm with living room with super comfortable couch and loveseat. FULLY air conditioned. The view is spectacular. 24/7 security building. Free assigned parking. Wifi with 3 smart...
WBH D225 Aloha Ola – Ocean and Pool View
Summary:This family-friendly beachfront, second floor 1-bedroom/1-bath air-conditioned Condo Suite comes with a comfortable king-size bed and living room couch that pulls out to a queen size sofa-sleeper allowing the unit to sleep up to 4 people. Just steps from the...
Maui Parkshore Condo with Kamaole Beach Views
Welcome to your comfortable 2-bedroom ocean view condo in South Kihei, the perfect Maui retreat for your dream vacation. The condo's location is just across the street from Kamaole Beach Park III, a popular family beach, making it easy to enjoy the sun, sand, and surf....
Hale Lani ~ Big Island Charmer with Panoramic Ocean Views ~ Near Best Beaches
This solar powered single family home is located on the coast in the foothills of hawaii island’s oldest volcano, Kohala mountain, with views of the coastline and ocean. This beautifully appointed home is conveniently located in the historic neighborhood of Kawaihae...
Blue Kauai Hale - Peaceful Multi-Level Home in Princeville
Relax with the whole family at this peaceful oasis. Blue Kauai Hale is the perfect base camp from which to explore and adventure on Kauai, then return home to soak in the hot tub and create more memories over a gourmet meal.Recently remodeled throughout with 4 bedrooms...
SLEEP NUMBER BED! #759 1bdrm-A Guest Favorite-Ocean/Beach View w/ XBOX & ROKU!
**********Watch our Beautiful Video: It's picture #3 (the daytime table)**************NOTE: We are in TOWER 2 - No exterior painting is being done on our Tower (we were last year). Only Tower 1 is being painted during Fall of 2024- Early 2025. Stay with us and not deal...
Beautiful Ocean View! Newly renovated kitchen and 2 Air Conditioners
Our 2 bedroom condo is located on the 3rd floor at the Kihei Akahi and just steps away from one of the most beautiful beaches on Maui - Kamaole II Beach. Newly renovated kitchen. We installed not one but two split Air Conditioners! One split AC is located in the Living...
SEArider ONE at Turtle Bay (2 bedroom / 2 bath) - Kuilima Estates East
~ You just found your Base Camp to explore the North Shore of Oahu ~Our condo has just been completely remodeled and redecorated with two brand new bathrooms as of September 2021. We are situated alongside the Palmer Golf Course and are a short 5-10 minute walk to the...
Free parking marinesurf Comfort central Waikiki
Aloha our unit have free reserve parking ,5-10 minutes walk to the beach , heart of Waikiki, International market, DFS , Royal Hawaiian shopping center. You stay in a very convenient and comfortable place .
Wailea Beach Villas | PH104
Marvel at the sophisticated style and décor of Wailea Beach Villas Penthouse 104, where a touch of Bali influence seamlessly merges with rustic undertones to create an unforgettable ambiance. The interior design captivates with elements like a textured wall-mounted...
Ocean View, Beach Front, Dream Vacation Villa, at Kahalu’u Snorkel & Surf Beach.
Our luxurious condo is located in Kailua-Kona at Beach Villas at Kahalu’u (BVK). This is your home away from home with 2 bedrooms and 2 full bathrooms that each have walk in showers. Our welcoming condo features 1 king bed and 1 queen bed, which is perfect for a small...
South Kihei Top floor Ocean View & easy walk to the beach.
2 Bedroom, 2 Bath, Sleeps 4 (2 Queen Beds) This spectacular TOP floor unit features Split System air conditioning which allows for individual climate control in each room. The A/C accommodates year-round enjoyment of the fully equipped chef’s kitchen, completely...
FULL OCEAN VIEWS Poipu Beach House, LOVELY lanai and A/C
Aloha & welcome to our home - Hale Kika @ Poipu Kai resort. Hale Kika is an open concept beach house with great views from the main living area, 3 bedrooms and 2 1/2 bathrooms. Views from the house span from the Haupu Mountain to full ocean views. Our 2-storey home...
Halana Malie - Ocean Views, A/C, Beautifully Furnished Halana Maile Sleeps 8, 3200 sq. ft
HALANA MAILE AT KOLOA KAI VACATION RENTALSOcean-View Luxury Nestled on Kauai’s Crater RidgeWelcome to Halana Maile, a serene and luxurious retreat perched on the side of an ancient crater, offering breathtaking ocean views and easy access to Shipwreck’s Beach near...
Amazing view, Close to the beach, Wailea Ekahi Unit 20i
Condo 1 bedroom, 2 bath (sleeps 4)PRIME location on the front row in lower Wailea Ekahi, Wailea. Listen to the sound of the waves and enjoy the ocean views. Famous Keawakapu Beach is just steps away! Beautiful ocean views from every room. Enjoy the extra-large lanai...
PUN 202 Updated Oceanfront Condo at Punahoa Beach with Stunning Views
FREE daily activities included with your stay value up to $554! Complimentary admission, every day of your stay*: Whale Watching (seasonal), Sunset Dinner Cruise, Molokini Snorkel Trip, Alpaca Farm Tour, Pineapple Farm Tour, and Tea Farm Tour. (S1)*One ticket per...
Largest Lanais in Lahaina! Ocean & Sunset Views HK245
Pure Luxury on Maui's Westside! A true romantic escape or the family vacation of a lifetime. You can have it all at Honua Kai Resort and Spa! Our desired inner courtyard sanctuary in the Hokulani Tower offers amazing amenities which include: 2 primary bedrooms with king...
Tropical Oasis! Beaches, Shopping & Comfort Pacific Shores A212
Experience paradise at this beautifully updated 2-bedroom, 2-bathroom vacation rental at Pacific Shores in South Kihei. Overlooking a lush tropical courtyard, this serene retreat offers the perfect blend of comfort and Hawaiian charm. The fully equipped kitchen and...
Traditional Hawaiian House - Walk to Tunnels Beach
TVNCU #1146 - A gated entrance leads you through a 6 foot lava rock wall toward the rear, ground level peaceful house. Privately tucked away, on the Mauka (mountain) side of the road, behind a front house (where the housekeepers live), the rental house sits. Capture...
2 Bedroom Poipu Condo with Pool, Hot Tub walk to Beaches
Regency at Poipu Kai 911 is an air conditioned, ground floor suite located just steps to the pool. This 2-bedroom, 2-bath suite is great families and walking distance to the beach. This stunning condo has been upgraded throughout and is one of the few air-conditioned...
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 View, 1st Floor, Spectacular Remodel, AC every room, Inner Courtyard
Check out our over the top remodel in every room. Redesigned throughout. Private guest room. AC in every room. The best location in The Palms. 1st floor walk out , near pool Provide beach chairs, ice chest, beach towels, boogie boards and other beach items. Puzzles,...
Impressive 2 Bdrm+2 Ba Paradise Condominium at Wailea Grand Champion Villas
Treat yourself to an impeccable Front-Row 2 Bedroom + 2 Bathroom paradise condominium at the Wailea Grand Champion Villas. This is the finest that Wailea Grand Champion Golf Villas has to offer in a 2 bedroom + 2 bath category. Upgraded in every way with split A/C...