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.
Tropical haven with pool, hot tub, grills & window AC - walk to beach
Maui Kamaole I112Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Walk just minutes to shimmering beaches from this condo, ideally in the Maui Kamaole complex. Enjoy views of the...
Ilikai 1418 2 Bed Room Luxury Remodel Ocean / Lagoon Views
OCEAN / LAGOON VIEWS! STEPS TO WAIKIKI BEACH. 2 bedroom, 2 bathrooms, two 120 sq. ft lanais, 1,000 interior sq. ft. Kg bed, 2 double beds, Qn sofa bed. Walking distance to parks, shopping mall, restaurants, shops, buses, rental cars, parks.The Ilikai Suites are located...
Pili Mai 10F - Vacation Rental in Poipu
Pili Mai 10FOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Ideal for a family beach vacation, this sunny and inviting, golf course-adjacent condo offers everything you need for the...
Family Condo!!! Close to BLACK ROCK 2BR/1BA Ocean View - K 112 ground floor
The perfect family friendly Maui beach condo. Come as couple, or bring the family, even the extended family!!Primary bedroom sleeps two, while the back bedroom has two twin-over-full bunkbeds that can sleep all the kids.Large banquette dining area can accommodate 8 so...
Spacious, stylish oceanfront studio
Noelani 118 is a Studio condo located on the ground-floor featuring amenities such as panoramic ocean views, an oceanfront lanai, and air conditioning. The condo can accommodate up to 3 guests with a queen-size bed and a queen sleeper sofa in the living room. The...
Wailua Bay View 215 Oceanfront condo
Welcome to this delightful condo in Kapaʻa. This cozy space features 1 bedroom with a comfortable king bed and air conditioning in the bedroom, perfect for a relaxing stay. Enjoy the convenience of WiFi, a hair dryer, and a washing machine during your visit. The...
🌺 IMMACULATE 3-BEDROOM 2-BATH UNIT IN KO OLINA KAI! 🏖️
IMMACULATE CONDO IN KO OLINA KAI! 🌺 🏡 This beautiful property features 3 bedrooms and 2 bathrooms, a full kitchen, Spacious living and dining areas and, of course, a nice lanai (balcony) so you can enjoy your morning coffee or watch a beautiful Hawaiian Sunset! 🌅...
29th Corner 1 BR Great Panoramic Ocean View!! Pacific Monarch
Enjoy the lovely Hawaiian breeze in this high-floor 1-bedroom unit. Within walking distance to Waikiki's finest destinations." The Pacific Monarch building is centrally located in Waikiki, with a great variety of entertainment and dining options nearly at its doorsteps....
Maui Kamaole F-204 | Large Private Balcony!
Welcome to Maui Kamaole F-204, your well-equipped and well-located address on the western shore of the beautiful island of Maui. This two-bedroom, two-bath spacious second floor condo is located in the first-class Maui Kamaole resort, which is situated on 23 acres of...
Maui Kamaole J214: Remodeled 2 bedroom condo with Ocean views, sleeps 6
Stunning remodel completed at the end of 2018 in this two-bedroom ocean-view condo at Maui Kamaole. This beautiful remodel can be most enjoyed in the kitchen and two full bathrooms. The furnishings in this condo are a mixture of tropical and modern and create a feeling...
Fully modernized 11th floor studio at The Palms
Situated just below the penthouse, this fully furnished, newly renovated studio features a preferred layout with 2 queen sized beds and open lanai.Fully modernized 10th floor studio at The Palms Hotel on the West side of Waikiki - Close to Fort DeRussey, Ala Moana...
Superior, remodeled, Oceanfront two bedroom 2.5 bath low rise, AC, pool.
Aloha, and welcome to this picture-perfect Puamana home. #43-2 is an ideal oceanfront location inside the beautiful protected Puamana grounds, unharmed by the Lahaina fire. This home has just recently been updated and features numerous improvements. Brand new, cool &...
Stunning Oceanview Studio, Remodeled Whaler 714, AC Steps to Kaanapali Beach
Welcome to Whaler 714, your ideal Kaanapali Maui vacation retreat. Perfect for the solo traveler, couple, friends, or small family, this beautifully upgraded ocean view studio on the 7th floor offers stunning views of Kaanapali Beach and unforgettable sunset beach...
Updated home with pool, patio, deck, WiFi, washer/dryer, & gas grill
Keauhou Surf & Racquet 3-201Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Nestled in the resort-style gated Keauhou-Kona Surf & Racquet Club community, this condo has been...
Stargazing Mountainside Cottage by Pristine Beaches
This beautiful, breezy, and quiet cottage in the stunning Makaha Valley offers a wonderful opportunity for you to immerse in Hawaii's peaceful nature. Surrounded by gorgeous ridges and valley, you will enjoy amazing views all around. The backyard patio is perfect for...
Tropical Gem Near 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...
Kahana Manor 502 Remodeled 2 bedroom 2 bath Oceanview
Book with us and come to Maui to explore everything we have to offer!Portable ACs installed in both bedrooms (not pictured).This remodeled 2-bedroom 2 bath Kahana Manor condominium has everything you need to relax in Maui. The granite and stainless-steel kitchen is...
Ocean View Room, Spectacular Beachfront Resort, 4 pools, Restaurants on site
Our unit is a privately owned hotel room located in the Outrigger Kauai Beach Resort and Spa.Beautiful fifth floor unit with amazing views of the ocean and pools. Comfortable King bed and Chaise Lounge.The Outrigger Kauai Beach Resort and Spa is a beautiful Hawaiian...
🏖️Concierge Included | Ground Floor with Ocean Views | vrKCV
vrKCV - Sea Village 2106, Professionally Managed by Kona Coast VacationsRelaxed Ocean-View Escape Near Downtown Kailua-KonaPerfect for couples and families, this bright and breezy two-bedroom, two-bath condo offers a comfortable home base on the beautiful Big Island....
KR506-Ocean View - Beachfront Resort - Great Winter Whale Watching!
Located on the fifth floor, Kealia unit 506 offers a spacious and relaxing retreat. The master bedroom boasts a king-size bed as well as a lofted day bed in the alcove, providing ample sleeping space. Step out onto the private lanai to take in stunning ocean views and...
Oceanfront 2Bd 2Ba Sunset Suite in South Maui
Unbeatable Location, Unmatched Views – Your Dream Vacation Awaits!Get ready to experience the vacation of a lifetime in this renovated 2-bedroom, 2-bath oceanview condo at Kamaole Nalu. With jaw-dropping views of the sparkling Pacific, this gem is the perfect blend of...
Sea Breeze Retreat at Turtle Bay - Kuilima Estates West
Aloha and welcome to our Sea Breeze retreat, a 2-bedroom, 2.5-bath condo at Turtle Bay! Step outside the living room onto a beautifully manicured lawn overlooking the Fazio Golf Course. This gated condo offers the perfect blend of relaxation and convenience, just a...
Fully Remodeled, Affordable Quality 3-4 mins walk to Waikiki Beach
Legally permitted short-term vacation rentalBamboo Waikiki2425 Kuhio Ave 502Honolulu HI 96815Our Brand New Fully updated Suite at Bamboo Waikiki Hotel in the heart of Waikiki is delightful & just 3-4 mins walk from Waikiki Beach.With all new floors, furniture &...
Kihei Retreat w/ Kamaole Sands Resort Amenities!
Stay at this 2-bedroom, 2-bathroom vacation rental, and get ready to experience R&R like never before. The condo boasts at-home essentials and ample resort amenities to ensure an unforgettable stay. Along with swimming and surfing, you can also experience great...
Molokai Shores 217
Molokai Shores unit #217: Upon entry, notice the open layout that leads your gaze to the sliding glass door offering views of the Hawaiian blue sky and palm trees just outside your second-floor retreat. Handsome hardwood-like flooring and a charming island décor...
Ilikai Marina 1792 Ocean / Sunset / Fireworks Views King Bed, Sofa Bed
UNOBSTRUCTED SUNSET/OCEAN VIEWS! STEPS TO WAIKIKI BEACH. Walk to parks, shopping mall, restaurants, shops, buses, rental cars & Waikiki night life. Parking available. No smoking room. Clean and fresh high floor.UNOBSTRUCTED SUNSET/OCEAN VIEWS! STEPS TO WAIKIKI BEACH....
Keauhou Punahele A104 - Cozy Island Themed 2 Bed 2 Bath
Say aloha to your own slice of paradise in this beautiful island-inspired 2-bedroom, 2-bath condo at the Keauhou Punahele complex. Overlooking the lush greens of Kona Country Club and the sparkling Pacific beyond, this peaceful retreat combines comfort, privacy, and the...
🏖️Direct Ocean Front | WIFI | Concierge Included | vrKCV
vrKCV - Sea Village 4106, Professionally Managed by Kona Coast VacationsDiscover Oceanfront Comfort and ConvenienceStep into the charm of this budget-friendly, uniquely styled oceanfront condo, offering a cozy haven for your Hawaiian getaway. Located on the ground...
Beautiful Mauna Lani Golf Villa! Club Access, Gated, Sleeps 4, AC, Pool, SpaPool
Paradise on the Kohala Coast! Welcome to the exclusive and pristine Mauna Lani Golf Villas located in the Mauna Lani Resort. This condominium offers expansive views over Mauna Lani's golf course. Enjoy breathtaking sunsets from your private patio as you settle into the...
Maui Resort Rentals: The Whaler 724 - Corner 1BR/2BA w/ Wrap-Around Balcony, Gorgeous Partial Ocean and West Maui Mountain Views!
From its desirable 7th-floor corner floor plan, Whaler 724 delivers gorgeous views of the turquoise-hued Pacific, Maui's neighbor island Molokai, and the lush West Maui Mountains. During the winter months, this spacious 1BR/2BA suite enjoys an excellent vantage point...
Private Condo w/ Amazing Sunset View, Shared Pools/Hot Tub - Walk to Beaches
Manualoha 504Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Tropical Tranquility in Poipu — A/C Throughout, Garden Oasis, Steps to the BeachEscape to your own lush Hawaiian hideaway...
KAS 4413 Remodeled 2BD Beach Retreat Across Beach w Pool AC
Kamaole Sands 4413 Remodeled Coastal Style 2 Bedroom, 2 Bathroom Beach Retreat Across the Street from Kamaole III Beach Park in Kihei! FREE daily activities included with your stay value up to $554! Complimentary admission, every day of your stay*: Whale Watching...
Top floor one bedroom with King bed, On the Ocean
Sweeping views from top floor, King bed condo A514Rare and fantastic location and awesome views of the ocean, palms in the tropical oasis of Maui Sunset. The best location in a 1 bedroom at Maui Sunset.Premium renovations top off the experience, although you'll spend...
Grand Champions 87 ocean-view condo with pool, hot tub & washer/dryer
Wailea Grand Champions 87Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Newly and beautifully remodeled from top to bottom, this golf-course-front condo in the heart of Wailea will...
Hale Kamaole Condo w/Private Washer/Dryer, Shared Pool, Free WiFi
Hale Kamaole 110Our 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...
Molokai Shores 205
It’s all about the view in this 570 sq. ft. home edging landscaped lawns and the Pacific. A private lanai offers incredible views for sharing meals prepped in the open-style kitchen. Other comforts include hardwood floors, breakfast bar, cable TV, and ceiling fans....
Tropical condo with pools, lanai & BBQ
Welcome to your peaceful Waikoloa retreat - where island breezes, palm-lined paths & ocean views set the rhythm for relaxation:- Sleeps 2 | 1 bedroom | 1 bed | 1 bath- 2 shared pools & hot tub- Private lanai w/ ocean & garden views- Chef’s kitchen & dining area- BBQ...
Oceanfront Condo-Paradise
Kona Reef is a luxury resort in Kailua-Kona just two blocks from town and next door to the beach. The unit sleeps 4 comfortably with a king bed for the Master bedroom and a new queen sleeper sofa in the living room. The pool, hot tub and BBQ area overlook the ocean. It...
Rear Ocean View 2 Bedroom Single Level Condo at Kamaole Sands 9-305
ook with us and come to Maui to explore everything we have to offer!Now with newly remodeled bathrooms!A rare single level 2 bedroom/2 bath unit with beautiful ocean views at the Kamaole Sands Resort. Enjoy our new and quiet split Air Conditioner in both bedrooms and...
4 Star Oceanfront Property, Kauai Beach Resort, 4 Pools, Restaurants on Site
Our unit is a privately owned hotel room located in the Outrigger Kauai Beach Resort and Spa.This is a beautiful second floor unit with a view of the park and ocean behind it. Comfortable king bed with chaise lounge and balcony.The Outrigger Kauai Beach Resort and Spa...
Charming Studio in Waikiki - 2 Full size Beds, Free Wi-Fi
You get a great view from the 22nd floor which allows you to observe all three of the main Waikiki sights at once: the ocean, Diamond Head and the Ala Wai Canal!All year round you can enjoy the cooling breezes from the canal and the ocean.Located next to the Ala Wai...
Oceanview Maui Condo - Steps from Kamaole Beach!
Escape to paradise at this charming 2-bedroom, 2-bathroom condo in the highly sought-after Maui Kamaole complex in South Kihei. Located just across the street from the beautiful Kamaole Beach III, this second-floor unit offers stunning ocean views, perfect for catching...
Top Floor! Vaulted Ceilings! Direct Ocean Views! Come to Maui! #217
ALOHA AND WELCOME TO HALE KAI # 217MAUI MAGICImagine walking through your new oasis, and having one of the most outstanding views of the ocean. The ocean is so hypnotic, that nothing else seems to exist but you and the moment you are in. You could sit for hours...
Great Partial Ocean View! Full Kitchen, Free Parking, Pool! Heart of Waikiki!
Royal Kuhio #2408 – 2240 Kuhio Ave.(30-Night Minimum. ALL MONTHLY RESERVATIONS ARE SUBJECT TO APPROVAL.)NEW TO OUR INVENTORY! Partial ocean view unit on the 24th floor of Royal Kuhio, right in the heart of Waikiki! This 1-bedroom, 1-bath condo features 538 sqft of...
Kahala Cottage by Gather: Cottage w/ Private Pool, A/C, Walk to Beach and Shops
Kahala Cottage – A Tranquil Retreat in HonoluluWelcome to Kahala Cottage by Gather, your home-away-from-home in the exclusive Kahala neighborhood on O‘ahu’s south shore. Offered as a monthly rental, this two-bedroom, two-bath island retreat blends laid-back Hawaiian...
Kauai Tree House - Nestled Along a Stream & Secluded, Tropical Surroundings.
This incredibly special home situated on nearly half an acre, perched among the trees, and with over 200 feet of frontage along the Wainiha River allows for privacy and serenity during your stay while providing all the amenities you’ll need. It is located just west of...
Aloha Condos, Ilikai Marina, Condo 992, Oceanfront, AC
Ilikai Marina Condo 992 offers stunning marina and ocean views, a well-stocked kitchen, and a convenient location near Waikiki’s quieter end. Guests appreciated the cleanliness, comfortable accommodations, and proximity to Hilton Hawaiian Village. The overall experience...
🏖️Updated Top Floor | Ocean View | Desired Ocean Front Complex | vrKCV
vrKCV - Kona Isle C32, Professionally Managed by Kona Coast Vacations.Experience Tropical Paradise at Kona IsleWelcome to Kona Isle, an oceanfront haven where tropical charm meets modern comfort. This beautifully designed condominium unit is perfect for a relaxing and...
Escape to Serenity – Oceanview 1 Bedroom 2 Bath at Wailea Ekahi 48-E, Sleeps 4
Unwind in this gorgeous second-floor, 1-bedroom, 2-bathroom corner unit with breathtaking ocean views and lush tropical gardens right from your private lanai. "Serenity" offers the perfect blend of comfort and elegance, with bright natural light, vaulted ceilings, and...
2nd Floor w/Ocean Views + Lanai - Kanaloa 2103
Castle Kanaloa at Kona Resort #2103 - Kona living doesn’t get any better than this! Whether you’re treating yourself to a casual retreat or a romantic getaway, you’ve found the perfect place to spend your vacation. The lanai is furnished and also has a wet bar, which is...