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 Air Conditioned 3BR Kauai Resort Condo
Spacious 3 bedroom Regency condominium in the Poipu Kai resort- minutes walking distance from beautiful Poipu (10), Shipwrecks/Keoneloa (12) and Brennecke's (7) beaches on Kauai's sunny south shore. Double corner unit (windows on 3 sides) with vaulted ceilings in living...
Stunning Oceanfront, 2BR/2BA, Gorgeous Ocean & Mt. Views, Premium A/C
Stunning 2 bedroom 2 bathroom Condominium in Menehune Shores.From the moment you walk into this condo you will feel a sense of serenity and calm as you experience the panoramic ocean views and listen to the gentle surf rolling on the shore. You are only 50 steps to the...
Ideal island escape with beach access, shared pool, lush gardens, WiFi & lanai
Salt & Palms at Plantation Hale E3Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Feel right at home in your very own island retreat mere steps from crashing waves and soft sand here...
Wailea Ekolu 1605 60%Off May & June Deals at Relaxing Peaceful Condo
The Stice Team — Powered by Gather Vacations. Maui Born and Raised Professionals. Your Local Experts in Crafting Unforgettable Stays.Welcome to Wailea Ekolu 1605, a ground-floor two-bedroom, two-bath sanctuary tucked into the lush tropical tapestry of Wailea, South...
BEAUTIFUL NEW Beach-chic condo with AC 1 mile from Paia & Steps to Mama's Beach
Ku'au Plaza is a very small, friendly, quiet 30 unit condo complex; the only one of it's kind on Maui's north shore. Our fully remodeled, Beach Chic style condo is ideally nestled next to Mama's Beach & tide pools and the famous Mama's Fish House, only a mile from hip...
Bamboo Suite - Beachfront Ground Floor Condo - Lae Nani 316
Aloha! This great condo is ground-floor, oceanfront, two-bedroom, two-bath — overlooks beautiful Wailua Bay on the Garden Isle of Kauai. From the lanai you look across the broad green lawn with its palm trees and tropical plantings to a natural sandy swimming...
Hawaii Dream Escape: 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...
Hilton Waikoloa Pool Pass for stays thru 2025. Waikoloa Beach Villas M33
This vacation rental is professionally managed by ResorticaHawaiiWaikoloa Beach Villas M33Please scroll down for detailed informationBedding Configuration:Master Bedroom: King BedGuest Bedroom: Two Full Size BedsAdditional Bedding: Sleeper Sofa in the Living RoomHilton...
#03 Kawela Kai 501:Updated NorthShore Beach Front-Relax & Unwind
LEGAL LICENSED SHORT-TERM RENTAL! CERTIFICATE:1990/NUC-2059 LICENSE# 90/TVU-0004 TAX MAP KEY: 1-5-7-005:007 This home is NOT affected by the new Honolulu County ban on vacation homes. Make sure when booking your vacation home the property that you are reserving has a...
Central location, Steps to the Beach, & Convenience Shops, restaurants.
We are proud to offer you a clean and modern condo in the heart of Kauai. It's convenient location will allow you to enjoy all that the island has to offer. Our unit is part of Plantation Hale suites which features 3 outdoor pools and spas, BBQ areas, and a full...
Beautiful ground floor unit!
This spacious one bedroom condo sleeps four people comfortably. Step off your private lanai (patio) onto plush green grass for a short few steps to a beautiful heated swimming pool, surrounded by colorful tropical foliage. Then, take a few more steps through more...
Experience the beauty of Polynesian Shores #124
A LITTLE ABOUT THIS CONDO...."Welcome to Polynesian Shores #124, your haven of relaxation and rejuvenation. This cozy condo sleeps four, with a queen bed in the bedroom and a sofa bed in the living room, offering comfort for all. Whip up delicious meals in the full...
Perfect Location In Waikiki, Near Beach, Shopping, and Dining!
If you're looking for your get-away spot, look no further. This condo located within the Ilikai Hotel on the 4th floor is perfect for your vacation on Oahu. Wake up to the beautiful ocean view or relax on your spacious and private lanai at watch the surfers riding the...
Gorgeous*Peaceful*Condo* Steps to beautiful beach
****Outstanding Condo located in the best part of Kihei! King Bed and free Wi-Fi + cable - Great Price for all of the amenities of Home + Great Location**** You are invited to stay in this beautiful, romantic condo in South Kihei, right next to the ocean. You will not...
Maui Resort Rentals: Honua Kai Konea 444 – Extra Large Upgraded 1BR w/ Gorgeous Partial Ocean Views!
One of Honua Kai's premier one-bedroom suites, Konea 444 is an expansive one-bedroom suite that offers vistas of the tranquil blue Pacific Ocean and views of Maui's neighboring island of Lanai. You will have plenty of space to relax in the 780 sq. ft. upgraded interior...
Pali Ke Kua 112 ..Freshly renovated-endless views of the blue sea
Just the two of you. Off to leave the world behind somewhere on the edge of an endless blue sea. The view must be magnificent, an uncrowded beach within walking distance is a basic requirement, the living space will be clean and attractive - and, of course, you must be...
Exquisite Oceanview - Kihei Surfside #310 - Your Gateway to Maui Bliss!
Kihei Surfside #310 – Breathtaking Ocean Views with Island Comfort and Split-Duct ACStep into the serene beauty of Maui with a stay at Kihei Surfside #310. This 1-bedroom, 1.5-bathroom condo offers stunning oceanfront views from the third floor and a comfortable...
Huge House, Heated Pool, AC, Steps to Kailua Beach
Inquire about short stays, we accommodate them where possible. Spacious, resort-style residence located within 100 yards of Kailua Beach. Featuring a private courtyard and pool, this indoor/outdoor floor plan is ideal for family gatherings. The extensive renovation...
Wailua Riverside Cottage - TVNC #1293 AC and Kayaks!
Wailua Riverside Tree Top Cottage! TVNC #1293*As featured on TV Sonoran Living LiveThis is a perfect place to experience the real Kauai in a residential setting next to the Wailua River and a block from Wailua Beach.TVNC #1293*On Island Contact 24/7: Candace MackWailua...
Charming West Maui condo in tranquil oceanfront resort
Papakea D309 is a 1-bedroom, 1-bathroom condo featuring amenities such as an ocean view, a washer/dryer, and air-conditioning. Located on the third floor, this condo can comfortably accommodate up to 4 guests with a Queen bed in the bedroom and a Queen sleeper sofa in...
Recently Upgraded - Garden & Ocean View Condo
A perfect place to make your home away from home! This 2-bedroom single story garden and partial ocean view condo has an open layout. Enjoy the amazing views. A very short walk right onto a well-manicured lawn, beautiful blooming trees, few steps to the pool, BBQ, few...
Ocean Front Pool Club. Includes Beach Gear! Halii Kai 24H
This vacation rental is professionally managed by ResorticaHawaiiHalii Kai 24H. Stunning 3 bedrooms. Ocean Front Pool ClubPlease scroll down for detailed informationBedding Configuration:Master Bedroom: King BedGuest Bedroom: Queen BedGuest Bedroom: Two Twin...
Kamaole Sands 6-303 - Courtyard and Ocean Views from Renovated 3rd Floor Condo
Step into your dream vacation at Kamaole Sands 6-303, located on the third floor in preferred Building 6! You will feel at home the minute you walk into this 1-bedroom 2-bath condo, which features a beautifully updated kitchen and bathrooms. Granite counters and tile...
Striking Fairway Views, Luxury, Serenity, Pvt Beach Pass
This Fairways Villa is professionally decorated and has an elevated, unobstructed view of the golf course with spectacular sunsets. The home stands on a perfect angle to the trade winds, allowing you to use the front and back screen doors and windows for a wonderful,...
Premier Luxury 3 bedroom Villa at Hualalai Resort with Golf Course Views!
Turn moments into memories at this private villa located inside the gated community of the iconic Four Seasons at Hualalai Resort. Experience world-class golf, spa, restaurants, and more. Waiulu Villa, 133C is a three-bedroom, 3-and-a-half-bathroom luxury ground floor...
Enjoy a Hawaiian vacation in Paradise Stay at World Famous Mauna Lani Resort
"The Fairways at Mauna Lani", is a private gated community of luxury homes on the Kohala Coast located inside the world-renown Mauna Lani Resort. The Mauna Lani Resort, also home to The Fairmont Orchid and the Mauna Lani, Auberge Resorts Collection Hotel are located 25...
Beautiful Condo in Exclusive Hali'i Kai Oceanfront Community
Enjoy upgraded resort living at Hali'i Kai 19H, a 3-bedroom ground-floor condo in a highly desired oceanfront community. The condo was fully renovated in 2020 and now offers new wood flooring, a new BBQ grill, new bedding and black-out drapes in the bedrooms. Guests...
OCEANFRONT, PENHOUSE Maui Kai 1005- Views of Lanai and Molokai!
Welcome to your luxury oceanfront escape at the Maui Kai Penthouse, located directly on North Kaanapali Beach. This top-floor, 1-bedroom, 1-bathroom suite offers unmatched panoramic views of Lanai, Molokai, and the Pacific from its private lanai — the perfect setting...
Kaanapali Alii Beachfront Resort,2B/2B No Resort Fees, Sleeps 4-6, max 4 adults.
The Kaanapali Alii has long been considered the most premiere luxury oceanfront resort on Maui located directly on the famous white sand Kaanapali Beach. Situated between the Maui Marriott and the Westin Maui Hotel, our 10th floor unit offers visitor privacy, yet is...
Stunning Views W/Lanai and Kitchen–Poipu Shores
Castle Po'ipū Shores 302A: Welcome to this amazing 3rd floor condominium with two bedrooms and two bathrooms. You’ll love the modern look of this unit, featuring granite kitchen and bathroom countertops, large ceramic floors, large wicker furniture, and stone...
Private Wing of Historic Home < 5 Mi to the Ocean!
Say 'aloha' to the Big Island from the comfort of this 1-bedroom, 1-bath home! Situated in Captain Cook, just a stone's throw from the Captain Cook Monument Trail and Napo'opo'o Park, this historic house is ideal for experiencing the best of Hawaii. Enjoy proximity to...
Elua Village Contemporary 2bd+2ba Oceanview
New and Fresh! Lots of new features in Wailea Elua Village 2001. We have been busy with major upgrades! New carpet and paint, new beds, new sliding glass lanai doors, new TVs and much more! An elegant kitchen and an expansive lanai are both available for your enjoyment....
Kuhio Shores 306: Vacation On Kauai Oceanfront
One of the best ocean views in Poipu at an unbeatable price. Across the street from Prince Kuhio Park, this unit overlooks one of Kauai's many great surf breaks (PK's). This beautiful third floor 900 sq ft. 1 bedroom 1 bath condo sits just 70 ft off of the waters...
Oceanfront condo with lanai, full water view, hot tub & pool
Kona Bali Kai #418Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Come in from the sun and enjoy the cool ceiling fans inside this tropical condo. A full view of the Pacific sets...
Cute Beachfront Condo w/ Lanai & Resort Pools
Whether you’re a romantic couple that’s seeking sunnier shores or a small family excited to make memories around Maui’s beaches, stores, and unique sights, this 1-bedroom, 1-bath Lahaina vacation rental comes with a central location to help you carry out your...
Sandy Beach House - Oceanfront with Private Pool & Sandy Beach
Picked by Islands Magazine as one of the top villas in the world, this spectacular home from our Kauai oceanfront rentals enjoys a private oceanfront location on a secluded beach. Sandy Beach House is bright, airy and the ocean is visible from almost every room in the...
Charming Historic Hilo House – Minutes to Beach!
Hula your way to Hawaiian paradise when you book this fully restored 1960's vacation rental house! This 3-bedroom, 2-bath Hilo home features a covered lanai and peek-a-boo ocean views from the yard. The University of Hawaii campus is a mere 1 block away while downtown...
Tropical Masterpiece in the Heart of Lanikai
Guests to our Well-appointed, Multi-story Home Enjoy a Quiet Location in a Coveted Beach Community. Down Our Private Lane You’ll Find a Large Tropical Lot Hidden Only 400 Feet from World-renowned Lanikai Beach.Three Bedrooms (Master Bedroom King, Second Bedroom Queen...
Close to many of Maui's top 10 beaches
Views of the ocean and West Maui Mountains from this condo! This condo's proximity to the sand offers the best ocean views and a short walk to Kamaole III Beach.Maui Parkshore 407 does not have A/C, is a 2-bedroom, 2-bath condo on the 4th floor, and can accommodate up...
Beautiful Plumeria Cottage-Anini Beach Plantation Style Home
PLUMERIAPlumeria is situated at beautiful Anini Beach, at 3585 Anini Road, 300 yards from the ocean, in an upscale yet relaxed residential area with the largest reef in the Hawaiian Islands. Our SPECIAL PERMIT NUMBER IS 2011-23 AND OUR TVNC NUMBER IS 4234 Nearby...
Poipu Kapili 50-Ocean & Pool View One Bedroom - Newly Installed AC
Poipu Kapili is home to ideal oceanfront condos. The location of Poipu Kapili Condo #50 is in the midst of the impeccably maintained luxury 52 villa complex.Upon entering Unit 50 you will feel yourself immediately relax with Island interior, high ceilings trimmed in...
Beautifully remodeled ocean view condo Unit #303
Beautifully refurbished condo including all new flooring, new cabinets and granite counters, and new bathroom including new tile shower, cabinet, and granite counter. The work was completed in June 2020. New living room furniture March 2016. Sleeps four with California...
Ocean Dreams Begin at #125
A LITTLE ABOUT THIS CONDO....Welcome to Polynesian Shores #125, your gateway to paradise. The moment you step inside this inviting garden-floor condo, you'll feel the serene charm of Maui. This oceanfront one-bedroom, one-bath retreat comfortably accommodates up to four...
Puu Poa 112 2bd/2ba sleeps 5 A/C oceanfront pool tennis best Bali Hai view
Comfortably furnished with great attention to detail, this first-floor condo with stairs to entry, is truly fabulous. Near the edge of a bluff overlooking the beautiful Pacific Ocean, this condo also commands spectacular views Bali Hai, the north shore landmark made...
Aloha Condos, Keauhou Kona Surf and Racquet Club, Condo 1-306, Oceanfront
Best oceanfront location in Kona with sunset views year round. Watch whales right from your condo during the winter months and fall asleep to the soothing sounds of the ocean. 30 Seconds from Blender to OceanPrivate Top Floor Corner Condo with Best Ocean/Sunset Views !...
Just add Sun & Fun. A/C - Pool & BBQ nFree parking - Easy Stay in Kihei 🏖
It's where Beach days, Sunset swims, and Poolside BBQs are all part of the daily plan.- Highlights:* Renovated Full Kitchen* 25ft to BBQ, Pool & New Spa* Just Steps from the Oceanfront* New Cleaning Crew on Deck!* Comfortable Queen Beds * Living Room w/ large Comfy...
Fairway Villas-Waikoloa /Discount Golf /2nd Floor/ Lake-Fairway View /Large 2B2B
Fairway Villas Waikoloa Beach Resort K22 is the larger floor plan of the 2B2B condo. This is a beautiful, well appointed 2 bedroom, 2 bathroom condo located on the 2nd floor (elevator available) next to the resort amenities offered, including infinity edge pool, spa,...
Oceanfront Condo Halii Kai 14D
Take advantage of this spectacular panoramic oceanfront view of the coastline when you book this vacation rental condo. Experience a real treat when you book between mid-December through early May and get a chance to see the friendly whales frolicking just off our...
The Sand- Cozy condo in the heart of Kona
Studio condo in the middle of Kona with an oceanfront view. It has A/C. and is walking distance to all of the local restaurants, coffee shops, galleries, churches, and farmers market. Also, just a short walk to the beach.This 1st floor unit has a queen size bed , sofa...
"Seascape" Tranquil Luxury Ocean View 2 Bedroom | 2 Bathroom
Welcome to Seascape at Lanikai 232, a serene third-floor oceanview condo designed for comfort and connection. With central A/C, modern upgrades, and a spacious layout, this 2-bedroom, 2-bathroom retreat offers the perfect blend of island relaxation and convenience. Gaze...