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.
Villas of Kamalii #27, Stylish Luxury Princeville Condo, Mountain Views, A/C
Welcome to your dream vacation home at Villas of Kamali'i #27, a luxurious tri-level townhome nestled within a private and gated community on the stunning island of Kauai. This newly updated and elegant air-conditioned villa is in an upscale gated community in...
"Surf's Up!" at Islander on the Beach 327 a Oceanfront Studio
Surf's Up! – Oceanfront Studio Retreat at Islander on the Beach 327Welcome to Surf's Up!, a newly refreshed top-floor oceanfront studio at Islander on the Beach. Here, the gentle sound of the waves and sweeping ocean views create the perfect backdrop for your island...
Aqua Aloha Surf Waikiki Studio
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...
Located on Kauai's magnificent north shore.
Watson Home in Hanalei on Kauai's magnificent north shore. This two-level home offers partial ocean views from large picture windows in the spacious living area. The wrap-around lanai provides beautiful views of the large back yard and lush, tropical surroundings.Just...
Direct Ocean Front, Renovated1 Bdrm Condo with Sweeping Views of the East Shore
This charming ocean front condo is unit # 226 at the Kaha Lani Resort, which is located on Kauai 's beautiful east shore, the famous 'Royal Coconut Coast'. From the lanai of this island home, you can view the endless stretch of shoreline looking both northward and...
Beautiful 1bd, views of koi pond and ocean views
Papakea D207 is a 1-bedroom, 1-bathroom condo that sleeps 4 guests. This condo offers a fully equipped and beautifully remodeled kitchen, featuring custom cabinets, granite countertops, recessed lighting, and stainless-steel appliances. Stay cool with window A/C in the...
272-2 Oceanfront Magic
Experience Oceanfront Bliss at Puamana, MauiWelcome to your perfect Maui getaway, a modern and beautifully updated oceanfront townhome in the serene Puamana community. Offering unobstructed views of the Pacific Ocean, this home invites you to immerse yourself in the...
Maui Resort Rentals: Honua Kai Hokulani 933 - Exceptional 9th Floor Ocean View Studio!
Newly launched in April of 2021, this incredible studio suite affords sweeping 9th-floor views of the Pacific Ocean and enjoys a commanding vantage point above the adjacent resort wings that compromise the views from floors 8 and below. Nestled in the Hokulani interior...
OCEAN VIEWS-BUILDING 10-STUNNING REMODEL-AC-WELL EQUIPPED-METICULOUS CLEANING
Book with confidence, this stunning 1 bedroom, 2 bathroom condo at Kamaole Sands has been completely remodeled. Everything in the condo is new and finished with high end materials. This condo is managed by PMI Maui, a local Real Estate Brokerage that specializes in...
Kahala 414 - Private Two-Bedroom Condo in Poipu Kai
KAHALA 414 AT KOLOA KAI VACATION RENTALSSpacious Two-Bedroom Ground-Floor Retreat in Poipu Kai ResortWelcome to Kahala 414, a relaxing and well-appointed two-bedroom, two-bathroom condo located in the heart of the beautiful Poipu Kai Resort. This ground-floor retreat...
Luxurious 3BR Retreat in Poipu Kai Resort with Pool, Elevator, & Beach Access
Kauai’s Luxury Tropical Retreat in the heart of Poipu Kai Resort!Located on the beautiful island of Kauai, this 3-bedroom, 3-bath unit offers the highest level of luxury in the Poipu Kai Resort area. These amazing accommodations feature 2 King primary suites and an...
Hotel Moloka’i 1 Bedroom Condo
Yea! Our WiFi has just been upgraded, September 2022, in our remodeled, privately owned unit. Our oceanside condo is located in the only hotel on the island, Hotel Moloka’i, and is within a 2 mile walking distance from Kaunakakai town.There is no keeping track of...
Top Floor Condo Close to Beaches
For those who want to escape and relax in one of the most luxurious, truly upscale accommodations on Kauai's incredibly beautiful north shore, Plantations at Princeville is the place.Everything in the professionally designed interior is upgraded - and absolutely...
Upscale 2BR/2BA Ocean View in Waikiki + 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...
NEW LISTING Private Home across from Keawakapu Beach Tennis Pickleball Court!
Keawakapu Retreat- " Alani" NEW LISTING ON VRBO, 4.9 Overall rating on other booking platforms!!! This recently remodeled home is nestled on over an acre property with four private homes. An estate from Old Hawaii-Days gone by. This three bedroom two bath home sits on a...
Wailea Ekahi 45B-Great Rates,Lovely New Kitchen, Large Lanai, Pool #3 w/BBQ
Unit 45B is located in Building 45 on the ground floor. This lovely one bedroom, two bathroom condo has a 400 square foot lanai with picturesque garden and ocean views and Quiet Pool 3 just steps away. Patio equipped with spacious patio seating & chaise lounge. This...
Spectacular Treetop Oceanfront View - Central A/C - Sleeps 6 - Turtles & Whales
Aloha, MAUI IS OPEN for tourists to visit!! The devastating wildfires in Lahaina are incredibly sad, but your condo is far away from them, and on the other side of the mountains. The Eastern side of Maui has hundreds of things to do, visit and see, without ever...
"Premier Oceanfront" at Lanikai 123 a Spacious 2 Bedroom | 2 Bathroom Condo
Lanikai 123 – Premier Oceanfront Living on Kauai's Coconut CoastEscape to Lanikai 123, a spacious second-floor oceanfront condo offering panoramic views of Wailua Bay, a beautifully updated kitchen, and inviting indoor-outdoor living. With two bedrooms and two...
2BR/2BA Close to Waikiki Beach with 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...
❤️PiH❤️ Makai Living ★ Bright and Modern ★ Close to Beach
Brought to you by Paradise in Hawaii Luxury Homes.Fresh and modern, Makai Living has it all. Makai means towards the ocean in Hawaiian. Makai Living at Fairways is a fully renovated modern two bedroom home within walking distance to the beach and ocean. It is located in...
Luxury Oceanview Waipouli Beach Resort & Spa
Your Sunrise Vacation Home™Enjoy your Kauai Vacation at the beautiful Oceanfront Waipouli Beach Resort & Spa. Located in one of the newest resorts on Kauai, H-402 is a 2 bedroom, 3 bathroom Oceanfront Penthouse Condo. You will enjoy relaxing sounds of waves hitting...
150K Reno-Ocean View* Across from Beach*PoolTennis
BRAND NEW 150K Renovation+BRAND NEW Hawaiian Styled Contemporary Decor. Ocean views+Breeze from the Lanai located in BLDG 5- Best in Kamaole Sands+directly across from the golden sand+crystal waters at Kamaole III..Walking distance to everything South Kihei...
Mauna Lani Terrace J103
Sophisticated, contemporary three bedroom condominium located at the point where the ancient fish ponds meet the Pacific. Enjoy the wide, unobstructed view from your lanai with your morning coffee and your sunset cocktail.Recently renovated, Mauna Lani Terrace J103...
Bright, modern home w/ocean views from the huge wraparound deck & private pool
Saltwater HaleOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'This beautiful home is perfect for the family getaway to the Garden Isle you've been looking for. You'll love taking in...
Tropical Romantic S. Kona Cottage with Incredible Oceanview
Makalani (Heavenly View) Cottage is a delightfully romantic cottage surrounded by a tropical garden in South Kona's coffee-belt with a breathtaking panoramic view of the Pacific Ocean. For the adventurous traveler seeking authentic Hawaiian beauty and serenity, you can...
Kiahuna - Ocean View - Ground Floor on Great Lawn with AC!
Aloha and welcome to your dream vacation destination in Kauai! Let me introduce you to our cozy beach bungalow, located in the sunny south shore of the island. You'll be staying in Building 27 and entering unit #175, an oceanview condo on the Kiahuna "Great Lawn." This...
Kauai Exclusive - Poipu Makani Lani - Private Home w/ Pool, Spa & AC
Named "Heavenly Breezes" for a reason, Poipu Makani Lani is a 4-bedroom, 3.5-bathroom custom home that is perfectly perched on the Kiahuna Golf Course's first hole. This modern single-level home offers three luxury master suites and a guest suite creating ultimate...
🌺Lush Oceanfront Penthouse with Pool, Hot Tub, Mountain Sunrises, Ocean Sunsets
🌺Lush Oceanfront Penthouse with Pool, Hot Tub, Mountain Sunrises, Ocean SunsetsDiscounts for Extended Stays. Digital Nomads Welcome!Clean & Green Sleep Suite Beyond Luxury to Vibrance Thank you so much for considering A502 Maui Sunset for your Time, Energy and Money....
House of the Turtle (CR 18) at Champion Ridge: Pool, Spa, AC & Stunning Views
Tranquility and luxury await in this single-level residence with spectacular Kohala Mountain views in the desirable gated Champion Ridge community. Situated in the heart of Mauna Lani, for convenient access to the finest beaches, golf, restaurants, and shopping, this...
Island Style Condo With Private Pathway To Hideaway Beach
This Pali Ke Kua townhouse condo is located in the town of Princeville on the lush North Shore of Kauai. The North Shore is known for its beautiful tranquil beaches and majestic mountain peaks. The world famous Na Pali Coast is located here on the North Shore. You will...
Pali Ke Kua #118: Ocean views from every room and gorgeous Bali Hai sunset!
1 bedroom, 1 bathroom corner unit offering a cozy bamboo motif that resonates with old Hawaii and when times were simple. The idyllic getaway from the fast-paced crowds, and ultra-modern world of hotel rooms. Ocean views from every room. Curl up on the lanai with a good...
KONA ISLE C38: TOP FLOOR CORNER REMODELED W/AC & INCREDIBLE OCEAN VIEWS.
Looking for the best of the best at Kona Isle? Kona Isle#C38 is arguably one of the best units in the entire development. Top Floor West Corner of Building C, you've got INCREDIBLE OCEAN VIEWS! This unit is fully remodeled from Top to Bottom, and has absolutely nearly...
Completely upgraded, Beach Tower 3 Bedroom. Last minute discounts 4/19-5/21/25.
100's of reviews available. Contact host. This elegant villa is located on the 4th floor of the Beach Tower just one back from direct oceanfront. Close to the waters edge at Lagoon 2, it boasts an ideal location nestled above the lagoon pool/BBQ/beach bar area and...
Enjoy Paradise at Our Mauna Lani Villa
Our townhome is located in the exclusive Mauna Lani Resort that is anchored by the Mauna Lani Auberge and Fairmont Orchid hotels. Being our guest gives you parking and lounge chair access at the Mauna Lani Beach Club which is a short 2 mile drive away. The walk to the...
Fully Renovated Corner Unit a Block to Waikiki Beach!
Ni'ihau Apartments #505 – 247 Beach WalkLocation, location, location! Ni'ihau is a hidden gem found within the hustle and bustle of Waikiki just a block away from world-famous Waikiki Beach where surfers and paddlers spend their days! Recently renovated (2019) from...
Oceanfront * Air Conditioned * Top Floor * Large Lanai * Updated!
As Owners who live here five months of the year we pride ourselves in providing all the amenities one could possibly want to make your visit enjoyable, including air conditioning throughout. We have often been told that staying in our condo is like being on a cruise...
Can't get any closer to the Ocean#2
Menehune 512 is a little gem in Paradise. Full brand-new remodel just completed. This one bedroom one bath sleeps 4 with the queen size hide-a-bed. With a fully stocked kitchen its better than home
Beautiful Condo -Stunning Ocean Viewsn
Welcome to B-304! Our condo has undergone recent renovations, kitchen equipped with new cabinets, granite countertops and all new stainless steel appliances. The bathroom has a walk-in rock and tile shower. Our condo comfortably sleeps 4. We have a queen size murphy bed...
Aloha Spacious Villa w/ AC & Garden, Walk to Beach
Five minutes on foot from Poipu Beach, our 1550-square-foot, fully air-conditioned, two-bedroom, two-bathroom unit is situated on the ground floor amid verdant tropical landscaping. Savor a private lanai with a private barbecue and outdoor dining in addition to large...
Close to beach, sleeps 2, AC, quiet, private
According to local laws, we have a minimum rental period of 30 days. This one bedroom apartment sleeps 2 people. It has a King bed in the bedroom with a wall mounted flat screen TV, split AC, glass sliding doors that open to the large covered lanai and grassy back yard....
Waipouli Beach Resort! Luxury Mountain & Peek Ocean AC Pool
Waipouli Beach Resort! Luxury Mountain & Peek Ocean AC PoolBeautiful 2 Bedroom, 3 Bathroom Condo at #1 Rated 1st Class Waipouli Beachfront Resort & Spa on the beautiful island of Kauai. Located on the 2nd floor, this well decorated 2 Bedroom, 3 Bath Condo offers easy...
Private home located in tropical setting close to beaches and waterfalls
This charming house is the perfect place to relax with its quiet and breezy atmosphere. Its set on its own private 1/2 acre within minutes to the beach. Located just down the road from one of the worlds biggest waves Jaws and some of Maui's favorite restaurants and...
Air Conditioned condo nestled between Prince Kuhio Park and tropical gardens.
Aloha and welcome to our condo in sunny Poipu, Kauai. A one bedroom, second floor air conditioned condo nestled between Prince Kuhio Park and tropical gardens. The living room has great views of the gardens and the pool. You can hear the ocean waves from your bedroom at...
DISCOUNTED! 199.00+ a Night. Steps to Beach, Double Lanai, 3 TV's, Central Air
ENJOY OUR LOW NIGHTLY RATES FOR 2025!! Located in South Maui. Legally licensed since 2005, Tax ID #TA/GE-052-562-5344-01. When purchased, had a tax classification as a hotel/resort. Most people picture in their minds their dream vacation, directly on a beach in summer,...
Modern Kailua-Kona Condo: New King Bed, Full Kitchen!
This one-bedroom condo is a hidden gem in the heart of Kailua-Kona, conveniently located close to downtown Kona and Ali'i Drive. The unit features a brand-new king-size bed and modern amenities throughout the cozy space, along with one bathroom. A full kitchen, complete...
Fabulous Ocean Views from Front Row Condo!
Why come to Maui and not be able to see the ocean? Enjoy dining from my lanai looking right at the ocean! My one bedroom condo in the Ginger complex (G-104) is your paradise! Over 20' wide living room, 1039 sq. ft. 2 baths, large master bedroom with a king bedroom set....
*NEW Poipu 2BR Retreat|Pool|AC & Athletic Club
Discover luxury in the serene Poipu Beach Estates with our charming 2br/1ba cottage. Enjoy farmhouse-inspired design, full kitchen with KitchenAid appliances, and quartz countertops. Relax in A/C-cooled bedrooms or on the lanai. Exclusive access to Poipu Beach Athletic...
REMODELED-KAMAOLE SANDS-BEAUTIFUL OCEAN VIEWS-AC-METICULOUS CLEANING
Book with confidence, this newly remodeled 2 bedroom, 2 bathroom (1188 sq. ft) condo that is located at Kamaole Sands. 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...
Spacious ground floor unit. Includes beach gear! Vista Waikoloa D101
This vacation rental is professionally managed by ResorticaHawaii Vista Waikoloa D101. Please scroll down for detailed informationBedding Configuration:Master Bedroom: King BedGuest Bedroom: Two Full Size BedsLiving Room: Sleeper SofaAmenities:Beach Equipment: All of...
Includes beach gear. BBQ Grill on the lanai. Beach Villas J22
This vacation rental is professionally managed by ResorticaHawaiiWaikoloa Beach Villas J22Please scroll down for detailed informationBedding Configuration:Master Bedroom: King BedGuest Bedroom: Queen BedAmenities:Beach Equipment: All of our vacation rentals include...