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.
Maui Sunset A310 - 1BR, 2BA Oceanview King Bed
A310 is a beautiful 1 bedroom, 2 bath oceanview condo at Maui Sunset Resort which is the perfect vacation home. The resort is oceanfront and has a large swimming pool, hot tub, a shuffleboard court, putting green, and gorgeous gardens and grounds. There are also gas BBQ...
Experience historic charm near Kailua Pier
Aloha, welcome to our amazing ground floor, garden view condo, in the heart of Kona town close to EVERYTHING! We have finished up with a complete remodel last year. It is all fresh and new just for you to enjoy. We live on island and would like to share are little...
Hale Keleka: 4 BR Hawaiian Plantation-Style Home in Poipu
Breezy, Hawaiian plantation-style getaways are yours at Hale Keleka, a 4-bedroom, 4-bath property in Poipu/Koloa that includes a 3-bedroom main house and a separate 1-bedroom Ohana (guest house). Bring your group of 12 and enjoy a roomy, open-concept floor plan,...
3bd 3ba Oceanview Condo w Office and AC and WIFI and Garage ACAA1
TA: 025-066-2912-01TMK: 750180080137This cleaning Fee includes a $100 Reservation Fee and $75 Damage Protection Fee.**Alii Cove unit provides spectacular sunset views! This particular unit is very quiet and has an ocean view from the main lanai and upper lanai. The...
Private Oceanview Top Floor Nihi Kai Villa Koloa!
Unbeatable location, unforgettable views—welcome to your South Shore escape! This spacious 2BR/2BA condo at Nihi Kai Villas offers sweeping views of Kauai’s south coastline all the way to Niʻihau, with breathtaking sunsets right from your lanai. Just steps from...
Direct Oceanfront Summer/Fall Special Rates was 275 NOW 175
From your PRIVATE LANAI you have UNOBSTRUCTED, DIRECT OCEANRONT VIEWS OF NEIGHBOR ISLANDS * GORGOUS SUNSETS * TURTLES * RAINBOWS * DOLPHINS * and last but not least WHALES during the winter season!ABOUT THE CONDO...This OCEANFRONT one bedroom unit is nicely decorated...
The Flying Honu is located in the heart of Kona Town
The Flying Honu is located in the heart of Kona three blocks from the Ironman starting line. Built on the fragrant pathway from the mountain to the sea (Mauka to Makai ) it is a great example of Hawaiian single wall construction. Open floor plan with large windows to...
Ocean View, Top Floor Unit - Updated Beach Chic Beauty! AC Units, Wifi & Pool
***Professionally Cleaned Condo, No-Contact Check-In/Check Out*** Beach chic, calm and serene, completely remodeled/custom ocean view condo at Maui Sunset. This tropical oceanfront complex has long been revered for the immaculate and beautifully landscaped grounds that...
In Town, Ocean View, Steps Away From The Beach, Shops, Restaurants And Bars!
This one bedroom, one bath which is ideal for the single traveler or couple. It has a King Bed, and a full bathroom with a brand new walk-in shower. Full kitchen with all items you might need. There is also a washer and dryer for your use inside the unit. Free parking...
Top floor end unit great ocean view
This renovated two bedroom unit has everything going for it. Each bedroom has its own bathroom, and king bed along with a separate entrance and separate lanai. We have a flat screen television in each bedroom along with one in the living room. The fully equipped kitchen...
Updated Ocean View 2br/2ba Oceanfront Condo with Sand Beach
Peaceful and quiet with spectacular unobstructed views of the sandy beach, ocean, palm trees and the Islands of Lanai and Molokai. This 2 bedroom, 2 bathroom condo is fully furnished in a light and airy Hawaiian style and is under new housekeeping management! Bathrooms...
203 - Gorgeous Remodeled Oceanfront unit with A/C!
* Awesome condo with air conditioning in a great location! * This ocean front condo has been fully remodeled! * 60 feet from the ocean - Watch the whales (in season) from your private lanai * 100 feet from one of the finest beaches in Maui - Wonderful snorkeling and...
Kuilima Estates West - remodeled 2 bedroom ( 2nd bedroom is large loft)
***WE ARE ON OAHU, AND CONTINUE TO WELCOME VISITORS***Fully remodeled 2 bedroom ( 2nd bedroom is large loft) beautiful condo with 2 full bathrooms. We are in Kuilima Estates West, which is next to , but not a part of, the Turtle Bay resort. We have 3 pools for your use....
OWL NEST: serene stream side retreat for 2 or 3
The Owl Nest: Family friendly. Be immersed in nature at our peaceful, cozy stream side retreat. Located next to the Waipio Lookout, our Hamakua Coast rain forest property is the perfect place for two adults with one child stays. Hear the rush of our waterfall and...
Spectacular Oceanfront Sunset and Whale Views!
Come stay on one of the most popular beaches in Hawaii! Mana Kai Resort is situated on Keawakapu beach and faces South, perfectly blocking the North winds and creating an ideal grassy space below to enjoy the afternoon sun. Morning strolls on this serene stretch of...
Ocean Views Bound to Take Your Breath Away AIR CONDITIONED Condo!
Puu Poa 110 a spacious luxury ground floor unit in Pu'u Po'a - #110 offers immediate access to an acre of lawn, the heated ocean view swimming pool, and tennis / pickleball court.A recent guest's comments: 'We loved every minute here. Condo is beautiful, location is...
Kai Lani-Beautiful Ocean View Condo In Paradise
2 bedroom, 2 bath spacious ocean view condo. Beautifully furnished with vaulted ceilings and ceiling fans. Lovely views of the ocean and green area. Kitchen has granite counter tops and stainless steel appliance also includes stainless steel washer and dryer. 55” 3D...
Waterfront retreat w/ a furnished balcony, incredible view, & a shared pool
Kona Bali Kai #205Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Paradise awaits at this two-bedroom, oceanfront, Kailua-Kona condo. Offering a variety of desirable amenities,...
Renovated 2 BR West Maui Condo (with AC), Ocean View, Sandy Beach
Welcome to paradise…aloha styleCome enjoy paradise in this renovated two-bedroom, two and 1/2 bath condominium with recently added AC in West Maui, Hawaii. With a panoramic view of the ocean, Kahana Sunset Unit E6, is just steps away from a private sandy beach. The...
Coral Hale 5br 3ba Luxury Home, AC, Private Hot Tub, Mountain Views, Beach Gear, Large Kitchen
Whether you are looking for a peaceful escape to recharge or a home base while you explore Kaua'i, this home is an exceptional option. With inspiring spaces for gathering, sharing a meal, and relaxing, interesting architectural details, and lush, tropical surroundings,...
Seaside Studio - Oceanview A/C & WI-FI - 1 minute from Beach
Oceanview - Air-Conditioned , spacious 450 sq.ft. Studio with a private covered lanai with a table and chairs for 2. Come & stay in our beautiful Seaside Studio Suite, full bath - 100 steps to Poipu Beach Park! If you want a location convenient to surfing or basking in...
Peaceful Island Bliss Will Be Yours
We invite you to be our guests in our remodeled and upgraded condo studio. ** Hawaii Tax I.D. TA 146881126401 & GE 146881126401**.We are located on the western shores of Maui in the beautiful laid back city of Kihei where you can enjoy the beautiful sea breezes flowing...
🏖️Concierge Included | Ground Floor - No Stairs | vrKCV
vrKCV - Vista Waikoloa C105, Professionally Managed by Kona Coast Vacations Vista Waikoloa C105: Luxurious Ground Floor Lanai with No Stairs!Welcome to Vista Waikoloa C105, an elegantly updated 2-bedroom, 2-bathroom vacation rental designed for an unforgettable Hawaiian...
Includes access to the Mauna Lani Beach Club. Villages at Mauna Lani 622
This vacation rental is professionally managed by ResorticaHawaiiVillages at Mauna Lani 622. Includes Mauna Lani Beach Club PassPlease scroll down for detailed informationBedding Configuration:Master Bedroom: King BedGuest Bedroom: Two Queen BedsGuest Bedroom: Two Full...
RARE 2 BEDROOM WITH NO STAIRS-OCEAN VIEWS-2 LANAI’S-METICULOUS CLEANING
Book with confidence, this nicely remodeled, 2 bedroom, 2 bathroom (1088 sq. ft) condo. This condo is managed by PMI Maui, a local Real Estate Brokerage that specializes in vacation rentals. We are located within a mile of the resort and available 24/7. This condo...
Fabulous Ulua Beach & Lush Grounds Await: Wailea Elua 807, Groundfloor Gem!
Wailea Elua #807 – Ground-Floor Serenity with Ocean Breezes and Refined ComfortWelcome to Wailea Elua #807, a beautifully appointed ground-floor, 1-bedroom, 1-bathroom condo designed for peaceful and private escapes in one of Maui’s most exclusive beachfront...
POPULAR ON OCEAN COMPLEX - GREAT AMENITIES AND LOCATION!!!
E komo mai (Welcome)!!!🤙 Kona Isle is known for the beautiful grounds and Lava rock Beach front property. It is managed extremely well and the best part is along the Ocean, with BBQ's, Picnic tables, Lounge chairs, Chairs, Saltwater pool and the Ocean splashing right...
North Shore Beachfront Condominium 30 day rental period
Haleiwa Surf condominium located just a few feet from the beach to enjoy drinks, meals and sunsets on your own spacious balcony.This Condominium is 'tropical' style with modern amenities including cable TV and fast internet connection. .The beach is ideal for...
New Listing! Adorable Renovated 2 BR in Poipu
Newly Renovated Coastal 2-Bedroom with Ocean Views at MakahuenaThe perfect home base for your Kaua'I vacation, this freshly renovated 2-bedroom coastal retreat at Makahuena featuring ocean views from your private lanai.Sleeping Arrangements (Sleeps 6):• Primary...
West Maui, Kahana Sunset, Ocean View with AC, Private Beach
Kahana Sunset is quite special since it has its own spacious white sandy beach in Keone Nui Bay. Sitting on our west facing beach you have picturesque views of Molokai and Lanai islands.Since this is a small complex, it is ideal for family vacations and there is...
Hale Mikana - Gorgeous Ocean Views, Pool and AC!
This gorgeous home has a large private pool and views of Kauai's serene ocean and mountains. Just steps from one of the worlds most beautiful golf courses, this homes location makes for the perfect tranquil vacation. Hale Mikana includes air conditioning in every...
Beautiful spacious 2 bedroom townhome at Mauna Lani! With A/C and WIFI!
Make memories and enjoy the perks of this quiet gated community at The Fairways at Mauna Lani. This spacious townhome has all the amenities and is located north of the Kona International Airport, on the sunny Kohala Coast. This townhome is nestled in the prestigious...
Waikiki Landmark Resort and Condos - Breathtaking 2 Bed/2 Bath, Free Parking
Treat yourself to a Honolulu getaway you won’t forget! Book a stay at this 1-bedroom, 1-bath vacation rental and enjoy resort amenities like rooftop pools, a hot tub, a worldclass fitness center, and more! The condo boasts floor-to-ceiling windows in both bedrooms...
🏖️4 Main Suites | | AC & Private Pool | Ocean View | vrKCV
vrKCV - Keauhou Estates Hale Ohana lea 8, Professionally Managed by Kona Coast VacationsWelcome to Halele'a, the House of Joy—a breathtaking Hawaiian retreat nestled within the private, gated community of Keauhou Estates. Designed to seamlessly blend luxury and...
Whaler 1273: Spectacular Penthouse Panoramic Ocean & Golf Course Views
Oceanfront 2 bedroom 2 bathroom for Whale WatchingThe ultimate in luxury, one of the few truly beachfront condominiums located right on Maui's famous Ka'anapali Beach. This spectacular oceanfront condo features two bedrooms, two bathrooms and breath taking views of...
Ocean Front Complex, Watch dolphins, boats, from lanai
Kona Makai is an ocean front complex with pool, hot tub, tennis courts, 5 BBQ's, gated entry at night. Beautiful landscaping, plenty of parking, a clean and quiet complex, you only hear the sound of the ocean, not the traffic. When the ocean is flat there is good...
Updated Condo in Oceanfront Resort w/ AC & Shared Pool, Water slide, Spas
Waipouli Beach Resort D207Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome to this beautiful, second-floor condo in Waipouli Beach Resort - an oceanfront complex with heated...
Private Lanai with the Best View in Town!
**Nohonani 405 – Your Oceanfront Sanctuary**Welcome to Nohonani 405, a stunning 2-bedroom, 1.5-bath unit on the fourth floor, featuring vaulted ceilings and breathtaking ocean views. Enjoy panoramic vistas from the kitchen, dining areas, living room, and master...
Pane Makai Poipu Beach House - Steps to the Beach!
Less than a minute's walk to the beach, Pane Makai is spacious, air conditioned, and can sleep up to 16 people! Located in sunny Poipu, Pane Makai and is the perfect gathering place for groups, large families, friends, and loved ones. This 6,000 square foot home is...
Maui Rainbows And Waves! ~Gorgeous Oceanfront! ~ 2 Bdrm ~Corner Unit with A/C
****TEMPORARILY CLOSED DUE TO THE DEVASTATING LAHAINA FIRE...WE HOPE TO BE BACK ****. APOLOGIES FOR THE CAPITAL LETTERS BUT IT'S VERY IMPORTANT THAT WE AS OWNERS ARE UP FRONT AND HONEST REGARDING THE CURRENT CONDITIONS OF LAHAINA TOWN...WE ARE A FEW BLESSED THAT OUR...
5 STAR CONDO, OCEANVIEW, FAMILY FRIENDLY
MAUI FIRE UPDATE: Papakea Resort services (electricity, water, cable, internet) are fully operational. All recreational areas are open and returned to regular operations. Maui is OPEN and welcomes respectful, caring, and compassionate tourism.PROPERTY DESCRIPTION:This 2...
"New" Luxury property. Walking distance to The One Hotel and Beach
This three-bedroom, three-bathroom condo is located in the heart of the Princeville resort community on Kauai. The spacious condo is air-conditioned and has great lighting, making it a comfortable and inviting space to relax in. The modern kitchen features granite...
Maui Sunset Vacation Rentals B510
From on the fifth 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. Large private condominium apartment at the resort condominium complex on the beach in sunny...
Oceanfront, newly renovated. As low as $220/night.
You will find yourself right on the ocean and far from the highway! Sit and relax on your private lanai while watching the waves roll into Wailua beach. The view is truly spectacular. Many guests have shared stories of watching whales breach on the ocean surface for...
Upscale and Elegant Vistas
Summary:Spacious and elegant condo in the much sought after Wailea area. Fantastic unobstructed ocean and sunset views. Completely remodeled in September of 2021, no expense was spared to create our ocean view oasis. This one-bedroom, two-bathroom condo features...
Ground floor unit w/ golf and ocean views, three pools and tennis on site
Country Club Villas 102Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome to this beautiful ground floor vacation rental which lets you drop your bags at the door, walk onto the...
Puamana 272-3 presents a unique opportunity to experience oceanfront.
Puamana 272-3 presents a unique opportunity to experience oceanfront living at its finest. Relax on your spacious lanai, just 50 feet from the water’s edge. Here, you can grill, dine, enjoy the ever-changing ocean views, watch surfers riding the waves, observe...
KS 404 Remodeled OceanFront 2Bedroom Condo w AC Pool
Kaanapali Shores 404 Recently Remodeled 2BD/2BA Ocean Front Condo at Kaanapali Shores KAANAPALI SHORES IS A HOTEL ZONED LEGAL VACATION RENTAL PROPERTY FREE daily activities included with your stay value up to $570! Complimentary admission, every day of your stay*: Whale...
🌺🌺 UNIQUE VILLA with Indonesian Flair! BEACHFRONT RESORT 🏖️🏖️
***August 2025 - Villa refreshed with new smart TV in living room, linens, towels, cushions, rug, guest bedroom furniture, and new furniture set to relax in the lanai.Relax...Escape from the hustle and bustle of the city and other crowded hotels. World class Ko Olina...
Sugar Beach PH32 Ocean Front Views steps from 5 miles of Beach
Book with us and come to Maui to explore everything we have to offer!This beautiful just remodeled unit at Sugar Beach is located on the top floor overlooking the south Maui bay. With views for miles from the balcony, you'll be able to see sunsets, whales, and miles of...