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.
Deluxe Island Retreat-Newly Remodeled - SUMMER SPECIAL
Paradise awaits you at this lovely seaside condo...….Relax amidst the lush tropical landscape that welcomes you to Ali'i Kai Condominiums. This ground-level unit opens up to an expansive tropical jungle on the “Mauka” (mountain) side, and to partial ocean views on...
Maui Banyan fave! Ocean View, Renovated, Steps to the Beach, King Bed, Split AC
We would like to welcome you to Maui Banyan H-308, a spacious 1-bedroom, 2-bathroom, tastefully furnished vacation rental condominium with private lanai and a sweeping ocean view.For long stays, (28+ nights), a long stay discount of 15% will be automatically reflected...
Unobstructed 180-degree Western Views just steps from Maui's Best Beaches.
KIHEI AND SOUTH MAUI ARE OPEN TO VISITORS AND WERE NOT AFFECTED BY RECENT WILDFIRES. For volunteer opportunities during your stay, go to: gohawaii.com/malamaWith whale-watching, sunsets, and swaying palm trees in between, this top-floor, one-bedroom unit has one of the...
Konea 312 at Honua Kai Resort ~ Stylish & Modern Upgrades, Light & Bright Condo
1 Bedroom + Den With Stylish Upgrades & Garden View ~ Hosted By Maui WestsideThis fully upgraded 1 bedroom plus den condo at the Honua Kai Resort boasts breathtaking views of the West Maui Mountains. With 915 sq. ft. of living space that has been renovated with designer...
Upscale Penthouse with Ocean Views & 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, UPDATED, 4th Floor, 1BR Cali King, Non-Smoking, SHARP!
2024 NEWS AND BEYOND: POOL CLOSURE NOTICE (ONE WEEK IN SEPTEMBER): The ENTIRE POOL AND DECK AREA will be CLOSED for TWO WEEKS beginning on the SECOND MONDAY of EVERY SEPTEMBER. Travelers, please make a note of this for future stays with us!Hello 1st time Guests and...
Upgraded unit with Panoramic Ocean and Mountain Views
With stunning views of the Pacific ocean, West Maui mountains, and Haleakala, this deluxe 2-bedroom unit is beautifully decorated, spacious and comfortably furnished. Upgraded with quartz countertops throughout and free ultra high speed internet (400 mbps with 2G and 5G...
KIHEI KAI NANI condo #203- Great Location , Steps to KAMAOLE BEACH II
The Kihei Kai Nani Resort is a popular, long established, South Maui vacation destination located in a fine area. Our Deluxe 1-bedroom condo has a beach and ocean view. The interior is 621 sq.ft. and the lanai is an additional 100 sq. ft. We are located near the very...
NSF 207 BeachFront Condo w Ocean Views BeachFront 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...
BEAUTIFUL HOUSE WITH 7/AC,BED ROOMS AND OCEAN VIEW
Location: Hauula, North Oahu, Oahu, Hawaii, USA (LOCATED TWO MILES EAST OF THE POLYNESIAN CULTURAL CENTRE) Accommodations: House, 7 air-condition Bedrooms + Convertible bed(s), 3 full Baths (Sleeps 9-18)Keywords: 7/AC Bed Rooms HouseFIVE STAR EXPERIENCE FOR A FRACTION...
Oceanfront, two-bedroom, recent full remodel, gorgeous sunsets every night
Hale Kai O Kihei CondoNewly remodeled, beautiful and comfortable, steps from the sandy beach. Drift to sleep at night to the soothing sounds of the waves.The beautifully furnished condo, featuring kitchen, bath, air conditioning, telephone, free WiFi, smart TV, and a...
Awesome Ocean Views From Ground Floor, A/C, Recent Remodel, WI-FI
Our ground floor one bedroom (with Cal King bed) air conditioned condo offers luxury at an affordable price.Our unit is fully equipped with everything you will need to have a relaxing and memorable vacation. Remodeled kitchen with granite countertops, custom tiled bath,...
Kona Reef, F5 - Remodeled, Stunning Ocean View, AC!
* PERFECT LOCATION * BEAUTIFUL OCEANFRONT VIEWS *Leave your worries behind as you step into this exquisite beach-front sanctuary just minutes from downtown Kona. With breathtaking ocean views and an unbeatable location, this fully-remodeled, modern condo is the perfect...
Ocean-View Condo - Shared Pool & Hot Tub - Internet, Washer & Dryer, Water-View
Kihei Ali'i Kai D204Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Maui perfection awaits at this thoughtfully updated vacation rental! This dreamy retreat has been recently...
Ocean Front Beautiful Bottom Floor Condo B117, 1 minute walk to beach
Beautiful Ground floor condo is great for kids and older people, Like having a huge yard right off your lanai. 300 feet to ocean and 17 feet to pool. Fully stocked condo. Queen Bed in master, and two twin beds in spare bedroom. No elevators to deal with. Home away from...
Hau'oli Place - Happy little tiki cottage in Volcano
Our cozy little "Happy Place", is right across from Volcano Village with its restaurants and Sunday Farmers Market, & 5 minutes from Volcanoes National Park. Perfect home away from home for exploring eastern Hawai’i!THE SPACEOur little Volcano Village is the perfect...
Summer Discounts for Fairway Villas at Waikoloa !!!
Enjoy your stay at this Hawaiian plantation style villa across the lake from the King's Shops and a short walk to the scenic Anaeho'omalu Bay. The villa is located on the 14th hole of the world class Beach Course in the heart of the Waikoloa Resort. Get ready to unlock...
Hale Ohia Seaside Charmer Near Iconic Big Island Beaches!
This is a solar powered 3 bedroom house in Kawaihae located a scenic 30 minute drive to the north of the Kona Airport. Unlike many Hawaiian rental properties, this home is centrally located near pristine beaches, places to eat and shop, and to area towns and areas of...
Hotel Zoned, Legal STV Rental in Beautiful So Kihei. Just Steps to the Beach!
Recently remodeled, come to Maui and enjoy this stylish and clean Hotel Style Room in the Tropical Setting of the Maui Banyan Resort. This unit is located on the second floor with a small lanai that is great for watching sunset or enjoying your morning coffee. There is...
Kona Plaza#302: Third Floor, Ocean View in Heart of Kona Town, Ac & Elevators
Knutson & Associates Property Management is proud to be representing Kona Plaza#302.Its amazing location puts you right in immediate walking distance to restaurants, beaches, shopping & entertainment right in the heart of Kailua Village.This third floor unit of Kona...
Partial Ocean King Studio with Kitchenette, AC, and Free WIFI!
The Royal Garden is located at 440 Olohana St., walking distance to everything. Take a short stroll to Luxury Row on the Waikiki "Strip", and the Ala Moana Shopping Center or Hawaii Convention center is in walking distance. Feel at home with split AC, cable TV, and FREE...
Charming Kaloko Mountain Cottage with hot tub - private,secluded and cozy!!
Wonderful, private and cozy cottage up in the forest of Kaloko Mauka ( directly above Kona town!). Situated on 5 acres and 2700 foot elevation, this stand alone cottage is surrounded by beautiful ohia trees and is at least 300 feet from the main residence. The owners...
"Sunrise Hale" at Islander on the Beach 329. A Oceanfront View Studio with AC
Sunrise Hale – Oceanfront Studio Bliss at Islander on the Beach 329Welcome to Sunrise Hale, a newly introduced, top-floor oceanfront studio at Islander on the Beach. With a bright coastal vibe and unobstructed views of the Pacific, this charming retreat invites you to...
Upscale Executive Retreat--Newly Renovated and Air Conditioning!
This newly renovated upscale condo is stunning! All new bathrooms, kitchen, flooring, and furnishings. Condo is very clean and comfortable and gets a great breeze, and we also have AC. We are located on the ocean facing section of the complex. Your comfort and...
DIRECT BEACHFRONT 3BR 2BA! INCREDIBLE VIEWS! Sleeps up to 12! AC!
Direct Beachfront!! Incredible Views!! A/C!!! In Resort zoned Hotel with on-site restaurant!!Beautiful condo right on the beach with fantastic ocean views! With over 2,000 square feet (including two lanai's) this 3 bedroom 2 bath condo is one of the nicest and largest...
HO'OLEI #93-2-BEAUTIFULLY APPOINTED VILLA-SLEEPS 8-METICULOUS CLEANING
Book With Confidence This Luxurious 3 Bedroom, 3.5 Bathroom (2426 sq. ft) Villa That Provides Everything That You Need To Have A Great Vacation. The House Offers Tremendous Vacation Experience With It's Amenities, Location, And Level Of Finishes. It Is Managed By PMI...
Mauna Lani Palm Villas D2 Corner Unit with Views of Historic Lava Fields
Experience an unforgettable Big Island retreat that stands apart from the rest at this beautiful condo in Mauna Lani Palm Villas Resort! From the tranquil setting to the luxury finishes, this wonderfully positioned corner condo offers a special glimpse of Hawaii's...
TRULY BEACHFRONT House + 2 cottages for extra guests or privacy
30 Day Rentals Available. High Speed Internet. Remote Work in Paradise!Popular beachfront rental well known as the LAIE BEACH RETREAT or LAIEBEACHRETREATSandy BEACHFRONT North Shore retreat located on the Hukilau Beach of Laie Bay! Our beautiful home is well known as...
Luxury Suite w/ Ocean View in Waikiki + 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...
Newly Renovated Modern Cottage: Walk into Historic Wailuku Town!
Brand new, freshly renovated, permitted & legal. Private entry & parking in front of entry. If you were looking for a great deal in Central Maui, you’re in luck as the rates offered for those who book now are very competitive to welcome you to get away to one of the...
Oceanfront 2 BR/2BA in Beautiful Sea Village.
Stunning oceanfront views from the lanai, the sounds of the surf on the rocks, and the spirit of Aloha welcomes you to our home in Hawaii.Sea Village is a beautiful oceanfront complex with well maintained gardens, swimming pool, hot tub, gas barbeques, parking, and...
This newly listed condo boasts 3 spacious bedrooms and 2 luxurious bathrooms.
Welcome to our newly listed vacation rental in the prestigious Halii Kai community! This stunning condo offers the perfect blend of luxury and relaxation, with 3 spacious bedrooms and 2 luxurious bathrooms. The meticulously maintained ground-floor location provides easy...
Stylish Condo w/Central A/C, Shared Hot Tub, Pool, Free WiFi - near Poipu Beach
Pili Mai 12IOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Turn the key and step into the lap of luxury at this brand new, two-story condo in the plush Pili Mai community....
Spectacular Oceanfront Views
Remodeled floors, kitchen and bathroom!(To see our reviews for our other units in this building, search on this site for 1070628 and 1893280)1 bed (Cal King), 1 bath, beachfront condo, Free Wi-FiYou Can Not Get Closer to the Ocean on Maui!This romantic getaway is quiet...
Oasis at Turtle Bay Condo on the North Shore - Kuilima Estates West
This homey one bedroom (cal king bed) with upstairs loft (with one queen and one twin bed)/two bathroom Turtle Bay condo offers the perfect true Hawai'i get-away for up to five! It's close to the public beach at the Turtle Bay hotel, sitting on the 1st hole of PGA Fazio...
Absolute Luxury on the Ocean
SPECTACULAR RENOVATION. First time offered to rental guests. Totally renovated ocean front unit at Paniolo Hale. This unit is on a PRIME OCEAN FRONT location. Watch the surfers from your front row seat on the lanai with monk seals sleeping on the beach, and migrating...
Kahana Outrigger Oceanfront Property 3 BR/3 BA Unit #2A1
Home away from home is the only good description of our "condo" in Kahana. Fantastic sunsets, outstanding views in all directions, romantic moonlit nights, and whale watching (in season) are all to be expected at our Kahana Outrigger vacation condominium.The unit has...
Alii Cove F-1 - Beautifully appointed townhouse located in downtown Kona
Alii Cove F-1 has reduced its nightly rates for the summer and fall! Come check out this roomy 3/3 townhome at the best prices since before COVID! Perfect size for families and entertaining!Alii Cove F-1 is a beautifully appointed end-unit townhouse. The spacious...
Beachfront Home + Cottage at Center of Hanalei Bay!
Welcome to our stunning, historic Hawaiian plantation home and cottage—nestled beachfront on over 1/3 acre at Hanalei Bay’s famous Pine Trees Park. A surfer’s dream in winter and a calm, swimmable bay in summer, this family-friendly, single-level compound includes...
Relaxing oceanfront studio on the beach
Enjoy panoramic, unobstructed views of the neighboring islands of Lanai and Molokai, while watching whales (seasonal) breach out of the water, sea turtles and fish swimming by and enjoy breath taking beautiful sunsets!Experience the time of your life in this spacious,...
Surfers Paradise!
AMAZING COUNTRY RETREAT ON THE COVETED NORTH SHORE!! Enjoy creating memories with your family and friends at our favorite place in the world. Surf, hike, swim, snorkel, take in the rays!!! This private estate offers ocean views just up the hill from world renowned...
Waipio Valley and Ocean View
Enjoy this breathtaking fully equipped home over looking Waipio Valley up close in this 4 bedroom, 2 bath and outside shower home with incredible views. There are plenty of rooms and views for a family or group of friends to experience the lush and tropical...
Shells At Poipu, lovely home, short walk to beach
Just a short walk to the beach, this lovely home is also a short walk to the resort community's swimming pool and tennis courts. Your beautiful home-away-from-home welcomes you to relax and enjoy a wonderful visit to the "Garden Island" of Kauai. Perfect for families...
3 minute walk to the beach! Close to restaurants/shops. Updated, clean with A/C
Our beautiful updated condo in the Maui Vista complex is conveniently located on the ground floor of Building 1, which gives direct access to the beautiful garden, heated pool and walkway to Charley Young Beach. It is well furnished and includes a well stocked kitchen,...
Hale Kai Lily - Waterfront Hawaiian Getaway
This single-level waterfront, home is thoughtfully curated & designed. New AC in every room. Featuring a full kitchen, living room, and lanai as well as 4 bedrooms and 3 bathrooms. The property is fully furnished and boasts captivating marina views from all common areas...
Diamond Head Luxury Home w/Pool, AC, Lanai and close to Waikiki, Hale Le'ahi
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 your dream tropical vacation begin when...
Hilton Waikoloa Pool Pass Included for 2025. Waikoloa Beach Villas C1
This vacation rental is professionally managed by ResorticaHawaiiWaikoloa Beach Villas C1Please scroll down for detailed informationPLEASE NOTE: Waikoloa Beach Villas C1 is listed for sale. Guests may be asked to accommodate showings/inspections with 48 hours notice....
Ekahi Ocean View Escape and close to beach (21F)
Hawaii Tax ID: TA-200-429-5680-01TMK: 210080600026We invite you to stay in one of Ekahi's premier ocean view units; with a 3 minute walk to the top rated Keawakapu Beach. Your home away from home is also close to private amenities including 4 pools (2 very close to the...
Hale Hanai - near Kealakekua Bay - Proximity to ocean without oceanfront price
"Pathway of the Gods" is the meaning of the name given by ancient Hawaiians to Kealakekua Bay. Five hundred feet from the bay, nestled among the palm trees and fragrant plumeria blossoms is the site of your next vacation. Let us "Big Isle" you!Hale Hanai is a...
Gorgeous Remodel, BEST location! KAKC206
This is a brand new unit; light, bright with beautiful breezes! Fantastic location in the complex. Close to everything you want/need in Kihei! Gorgeous sunset views. Come be our guest and enjoy the comforts of being in Paradise!!Aloha and welcome to PARADISE!!! This...