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.
Best Location Across Best Beach! New AC throughout
*AFTER LISTENING TO OUR GUESTS REVIEWS, WE HAVE UPGRADED THE AC IN THE CONDO. THERE IS NOW AIR CONDITIONING THROUGHOUT AS OF NOVEMBER 2024*Experience the timeless elegance of traditional Hawaiian decor, enhanced by the modern comforts of this beautifully appointed unit...
Tropical island condo with pool, hot tub, beach access, grills, & private lanai
Plantation Hale D10Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Indulge in a dreamy island retreat at this Plantation Hale condo. A pristine property, Plantation Hale offers...
Located minutes away from Historic Holualoa village and Kailua-Kona and beaches.
On half acre of lush tropical setting, minutes away from the historic Holualoa village, (driving) home of the best coffee in the world, also 10 minutes away, (driving) from Kailua-Kona and beaches. This room has its own private bathroom and a kitchenette with a...
KR105- South Maui Condo Garden-Level - Lanai with Ocean & Mountain Views
Kealia 105 offers a charming garden-level condo with a picturesque view of Ma'alaea Bay and the West Maui Mountains. The adjacent park's dappled light creates a serene ambiance, providing front-row seats to the breathtaking beauty of Hawaii. During winter, guests can...
Exclusive Golf Course Front Kuilima West by Beach w/Parking & Great Amenities
Book with confidence! This property is professionally managed by Ali'i Beach Rentals, an award-winning property management company.Indulge in the ultimate luxury vacation experience at this exquisite rental nestled within the exclusive Kuilima Estates West community at...
Two Bedroom Ocean View Deluxe Luana Kai C303
C303 with AC,is a deluxe, 2 bedroom, 2 bathroom, partial ocean view condo, with a king size bed upstairs and 2 twin beds downstairs. Great views over the pool area to the ocean, Maalaea Bay and the West Maui mountains. The floors are tiled except the bedrooms which...
Lemon Tree Lanai
This tranquil oasis amidst old-growth ‘ōhi‘a forest sits conveniently halfway between Hilo and Volcano and just minutes from the highway. Relax in the embrace of the Lemon Tree Lanai, a detached unit featuring a long, sunlit, screened lanai with seating area,...
Discover Maui Parkshore 408: beach access, stunning sunsets, and cozy comfort!
Maui Parkshore 408 offers one of the best locations in Kihei with beach access directly across the street! Dining, shopping, and golf all within minutes! Enjoy a gorgeous Maui sunset from your private lanai. The expansive floor to ceiling sliding glass doors allow for...
Welcome to Gorgeous Hideout - Kuilima Estates East
Discover the beauty and tranquility of Kuilima Estates East, nestled on the 17th green of the iconic Turtle Bay Fazio golf course. This beautifully appointed 1-bedroom, 1-bathroom unit spans 658 square feet, offering a perfect blend of comfort and convenience for up to...
Ground-floor condo with ocean views, private lanai, grill, pool, & hot tub
Pali Ke Kua 136Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Experience the tropical splendor and serene beauty of Bali Hai at this comfortable, ground-level condo. This...
Kihei Alii Kai A 302 - HUGE lanai! Kamaole Beach is steps away
Ocean Views of Kamaole Beach Park from this spacious lanai! Perfect for your morning coffee and the newspaper or an afternoon relaxer watching sunset. Central location makes trips to the beach or shopping/dining a breeze! The third floor location is easily accessed by...
Nani Kai Hale #407: One bedroom, two bathroom with ocean views , sleep 4
Located on the 4th floor, this unit sits on the beautiful and romantic white sand Sugar Beach. With renovations throughout and a Cal-King bed and TV in the bedroom, this unit is extremely comfortable. There is even a pull out queen sleeper sofa in the living room to...
Maui Resort Rentals: Luana Garden Villas 9B – Modern 3BR Villa at Kaanapali’s Newest Luxury Residences!
This luxurious 3Bedroom/3Bath residence is conveniently set within Enclave Two of the Luana Garden Villas. Villa 9B's north facing orientation offers a Shady respite from West Maui's legendary endless sun and its designation within our "Grounded" collection at the Luana...
Awesome Diamond/Ocean View Condo! Corner Unit!
Awesome Diamond/Ocean View Condo! Corner Unit!Location! Only 1 block from the world famous Waikiki Beach. Easy walk to restaurants, shops, kapiolani park. Conveniently located near bus lines. This unit is in Tower-I.You will enjoy:- Great Amenities: Pool, hot tub,...
Ocean View and Completely Remodeled! Just steps away from Sugar Beach! Kihei Kai Unit #3
Condo #03 is a partial ocean view located on the lower level just steps away from the pool, lawn area, barbecue grills and sandy beach. The furnished lanai has a partial ocean view for you to enjoy. This condo will sleep 4 comfortably with a Queen Size Bed and a sleeper...
Beachfront Property w/Sand Access at Waikiki Shore Condo with Full Kitchen
Book with confidence! This property is professionally managed by Ali'i Beach Rentals, an award-winning property management company.The Waikiki Shore located on 2161 Kalia Road, 6th Floor. (NO PARKING and NO POOL)*This property is new to our inventory, but we assure you...
Sugar Beach Resort Condo w/ Private W/D, Shared Pool/Hot tub-Near Everything
Sugar Beach Resort 222Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Join the many guests who return each year to Maui's Sugar Beach Resort to enjoy the spectacular views from this...
Updated ground-floor condo with partial ocean views, heated pool, & hot tub
Vista Waikoloa #A-105Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Upgraded comfort and tropical resort-style living are yours at this luxe island retreat. Complete with a...
HM A202 OceanFront Condo on Sandy Beach w Pool
FREE daily activities included with your stay value up to $570! Complimentary admission, every day of your stay*: Whale Watch (seasonal), Dinner Sunset Sail, Snorkel Sail, Alpaca Farm Tour, Pineapple Farm Tour, and All Day Electric Bike Rental. (W1)*One ticket per...
@Marbella Lane - Paradise Gem w/breathtaking views
Summary:Discover tranquility in this charming house of 4 bedrooms within a secure gated community, nestled in the captivating Makaha Valley. Ideal for family or friends, indulge in relaxation and forge lasting memories amid breathtaking ocean and mountain vistas....
Walk to Magic Sands Large Home w/ Private Pool, Hot Tub, Terrace & 2 W/Ds
Kona Kanewa HomeOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'You need never leave this four-bedroom home to have a memorable vacation in Kailua-Kona, as you'll have your very own...
Spacious Downtown Executive Retreat | Free Parking
Chic Downtown 1-Bedroom with Free Parking at Aston Executive CentreExperience the best of downtown Honolulu in this updated 1-bedroom unit, located on the 12th floor of the Aston Executive Centre. Enjoy stunning city views through floor-to-ceiling windows while taking...
Ocean-Lagoon Views PH at Ilikai Hotel by the Beach w/Spectacular Amenities
Book with confidence! This property is professionally managed by Ali'i Beach Rentals, an award-winning property management company.ILIKAI NOTICE — July 9, 2025Starting July, 2025, spalling repairs and full exterior painting of the building begins. Please be advised...
Oceanview -KUL302 - West Maui Stunning -Upgraded and quaint 1 bedroom/1 bath.
** Discounted Rates through Summer 2025!! **You'll love vacationing in unit #302, a great-priced one-bedroom, the one-bathroom ground-floor condo that has been tastefully updated with granite in the kitchen and bathroom. Enjoy the convenience of the ocean and pool view...
Comfortable Townhome in Waikoloa Resort - Walk to Shops!
Two-story townhome located in a prime location on the golf fairways at Waikoloa Resort, close to the best shopping, restaurants and beaches in South Kohala. This charming three bedroom property has a spacious living room with high ceilings, a full kitchen and a lanai...
2 Bedroom Stunner! Upper floor! Right on Ocean! Book Winter #211
ALOHA AND WELCOME TO HALE KAI # 211 Located on the beautiful island of Maui just 150 feet from the beautiful Pacific ocean, Hale Kai # 211 can be your home away from home. Our condo offers ample space, (988 sq. ft.), privacy and a prime location. With two bathrooms, two...
Luxurious oceanfront, walking distance to cafes, restaurants, and shopping!
Nothing beats the view from the Lanai in this Sandy Paradise. Imagine spotting turtles and waves before you even leave the place! You'll do it while enjoying the luxury of a hotel and coziness of home!You are centrally located in South Kihei, with access to many beaches...
Lovely 1BR Ocean View Condo, Near Beach + Free Parking!
Aloha from Midway Vacations! Our team of local hospitality experts is dedicated to turning your Hawaiian getaway into a reality. When you stay at one of our properties, you can count on a professionally cleaned and meticulously maintained experience. We're even...
Oceanfront Condo Near Kona's Banyan Surf
This Beautiful 1 bedroom, 1 bath Condo is just an elevator ride and steps from the oceanfront park where you can BBQ or watch the Surfers and sea turtles, or just lay out on the lounge chairs. If you don't like the Salt water you go in the Complex's Pool instead. During...
MRR Presents Kaanapali Ali'i 496 - Elegantly Remodeled 9th Floor 2BR w/ Epic Direct Ocean Views of Lanai, Molokai & Beyond!
This elegant 2BR residence boasts over 1800 sq ft and a stunning 9th-floor location in what is widely considered one of the best interior courtyard columns at the entire resort. Enjoy direct breathtaking Pacific Ocean views from Lanai to Molokai and beyond, as well as...
Modern Jungle Cottage
Located 5 minute drive to the ocean, 30 minutes from Hilo airport. Cottage is ideal for a couples, however if you have a family and wish to stay, we can provide air mattresses for the kids for up to two more people. Queen size bed in unit, WIFI, 32 inch TV, Private 6...
Maluhia: Luxurious Kailua Home w/Pool Oasis, A/C, Near Beaches and Shopping!
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Let the tranquil atmosphere of Maluhia by...
![[New] Ocean+Sunset View Retreat | Steps to Beach](https://media.vrbo.com/lodging/112000000/111830000/111821800/111821720/7615d25c.jpg?impolicy=ccrop&w=1000&h=666&q=medium)
[New] Ocean+Sunset View Retreat | Steps to Beach
New Listing Special!Welcome to your Big Island oasis at Puako Beach—just steps from world-class snorkeling, surf, and unforgettable sunsets. Enjoy ocean views, the soothing sound of waves, and a spacious lanai perfect for relaxing or dining al fresco. Expertly managed...
Hale Kamaole Condo w/ A/C, Shared Outdoor Pool - Beach Lovers Dream
Hale Kamaole 234Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Hale Kamaole is a South Maui condominium complex located across the street from Kamaole Beach Park III, one of the...
BBQ Grill on the lanai. Waikoloa Beach Villas H1
This vacation rental is professionally managed by ResorticaHawaiiWaikoloa Beach Villas H1Please scroll down for detailed informationBedding Configuration:Master Bedroom: King BedGuest Bedroom Upstairs: One Queen BedGuest Bedroom Downstairs: Two Twin BedsSleeper Sofa:...
East Hawaii - Ocean, Mountains & Waterfalls
It’s your time to visit the magnificent Big Island of Hawaii with its ocean, mountains, waterfalls, beaches, and endless activities. The Umauma Experience Makani Ea Home is your own piece of paradise waiting for you and your family! It’s a cute 2 bedroom with an...
Breathtaking Mountain Views, drive to Hanalei Town
Located in the stunning Villas of Kamalii complex, this beautifully-appointed three-bedroom, three-bath townhouse-style condo serves as an excellent setting for your tropical getaway. Ideally located in Princeville on the north-side of Kauai, here you will have...
Kapaa Shore Ocean & Pool View Condo
Kapaa Shore - Beachfront Resort on Kauai!Kapaa Shore Resort Unit 117 on the 'Coconut Coast' Kapaa, Kauai Vacation Rental with **Pool Heated**Your Dream Vacation! 'Oceanview' Unit B117 at Kapaa Shores offering a stunning oceanview with watercolor sunrises, whale watching...
Keauhou Kona Surf & Racquet Club Townhouse #4
ABSOLUTE OCEANFRONT! AIR CONDITIONED! REMODELED!Nestled at the edge of a secluded cove and beach, the newly remodeled 'Waving Turtle' Oceanfront Townhome offers dramatic ocean views from its lanai, living room, kitchen, master bedroom and master bathroom. It offers...
Royal Kahana 1104 - Oceanview Studio - Free Activities - Oceanfront Complex!
Royal Kahana Studio 1104 Wake up each morning to views of the beautiful Pacific and the island of Molokai resting on the horizon. You will enjoy a breakfast filled with tropical fruit and fresh island coffee on your private lanai in this comfortable ocean view studio...
Cool Hawaii Vibe+Decor! Chic Kitchenett, Lanai, and AC, WiFi–Waikīkī Grand #301
Castle at Waikīkī Grand #301 is a studio vacation rental just steps from the best Waikīkī have to offer. With Waikīkī Beach, Kapiolani Park, the Honolulu Zoo, and Waikīkī's outstanding dining, shopping, and activities right outside your door, there’s no better...
Kona Makai 5305 Top Floor, Ocean View, 1 Bedroom + Loft & 2 Lanais! SPLIT AC!
Newly remodeled in 2023! Pictures reflect the current updates! Incredibly special & unique unit at Kona Makai, this top floor unit with a loft has SPLIT AIR CONDITIONING INSTALLED! Split AC in Loft Bedroom & Back Bedroom! Very rare offering, and such a high in demand...
Steps to Best Beaches.Renovated! Best Value in Paradise! Free Wifi,Long Distance
1Bed/1bath vacation condo with full kitchen, the unit is newly renovated. It is centrally located is South Kihei, a cozy beach town in sunny South Maui.Quiet end unit away from traffic with lots of privacy. It's fully equipped with cooking, cleaning and fun beach...
Beaches & Sunsets-Heart of Kihei
The Absolute Best Location in all of Kihei!!! Our condo's central location makes it the perfect place to explore the rest of the island. The best part of the location is that it is right across the street from a couple of beautiful secret beaches and coves, where you...
Sugar Beach Resort Condo w/ Free WiFi, A/C-Snorkel, Surf, Swim
Sugar Beach Resort 335Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Join the many guests who return each year to Maui's Sugar Beach Resort to enjoy the spectacular views from this...
Koa Resort 1D- Special location- private and quiet- Air conditioning!!!!
A beautiful tropical garden setting awaits you from this first floor location. The one bedroom one bath apartment is upgraded and updated . New Air Conditioning throughout the apartment! It has a spacious living/dining/kitchen area. The bedroom has a queen bed and there...
KBR #202 - 2 Bedroom /2 Bath Ocean Front Upgraded Condo in Sugar Beach!
Experience the ultimate beachfront getaway at Kihei Beach #202, a beautifully upgraded 2-bedroom unit located on the 2nd floor. With central A/C, stunning ocean views, and a newly renovated kitchen, this condo offers a serene and luxurious retreat. The master and guest...
Aloha Ku'ilima - Kuilima Estates West
Relax and Unwind at This North Shore Oasis – Just Minutes from The Ritz-Carlton, Turtle BayNestled in the highly sought-after Gold Coast of Ku'ilima Estates West, this spacious condo offers the perfect blend of comfort, location, and convenience. Ideally situated near...
REDUCED TO 199/NIGHT, REMODEL COMPLETE! Kiana and Kalia's Island Paradise!
WATCH AND LISTEN TO THE WAVES CRASH WHILE YOU TAKE IN THE RELAXING SALTY FRAGRANCE OF THE OCEAN. IS IT TIME TO GET LOST ON VACATION WHERE YOU CAN ENJOY RAINBOWS, MOUNTAINS, TURTLES, KOI FISH, LUSH LANDSCAPING AND VIEWS ACROSS TO MOLOKAI! MAUI IS NOT JUST A TROPICAL...
Kona Shores 203: Amazing location&fully equipped condo in Oceanfront complex!
This Top Floor condo situated immediately next to Alii Drive has everything you need to enjoy your time on the Big Island of Hawaii! The property features a full kitchen and a full bathroom. There is a Queen sized bed, plenty of seating in the living area, flat screen...