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.
Mauna Lani Beach Club Pass included! 701 Fairways at Mauna Lani
Fairways at Mauna Lani #701: Exclusive Hawaiian ParadiseDiscover pure luxury in one of the most desirable locations in the prestigious Fairways at Mauna Lani. Unit #701 stands apart with its coveted west-facing orientation, treating you to breathtaking sunset views that...
Luxurious, Spacious, High-end Beachfront Vacation Villa Free Parking
Dreaming of a memorable yet affordable Hawaiian vacation? Our Villa is calling you! It is located on the sunny Western shore of Oahu, and was built as a paradise for family-oriented beach lovers. It is landscaped with beautiful palm trees, koi ponds, a sandy-bottom...
Kihei D-202-Oceanview Condo! Right Next to Dining and Shops
*Panoramic Ocean and Sunset Views*So Very Close to Dining, Shopping and Beaches*Large, Fully Equipped 1 bed, 1 bath CondoExperience the perfect Maui getaway in our stunning 1 bedroom, 1 bathroom condo at Kihei Alii Kai D202. Boasting breathtaking ocean views and...
Real Ocean Front! Private and well maintained! Excellent reviews!
Imagine being on a lava point jutting into the surf surrounded by beautiful views! You can relax on the 3rd floor private Lanai (balcony) and drift off to sleep to the sound of the waves. Or you can drink your favorite beverage and watch dolphins and whales in the...
🏖️AC | Captivating Sunsets | Magnificent Ocean View | Private Pool |vrKCV
vrKCV - Keauhou Estates Hale Ohana lea 11, Professionally Managed by Kona Coast VacationsStart Your Hawaiian Adventure at Hale Ohana Le'aImmerse yourself in the beauty and tranquility of Hale Ohana Le'a (House of Family Joy), a custom-designed Hawaiian retreat located...
Poipu Beach House with AC by Brennecke's Beach
With Brennecke's Beach and Poipu Beach within view and just a short walk away, this two-bedroom, two-bath beach house on Kauai's sunny south shore is a great place to call home when visiting the beautiful Garden Island. Enjoy tropical surroundings, ocean and sunset...
Beautiful 2 BR. Kiahuna plantation condo partial ocean view upgraded with A/C
Kiahuna plantation unit 95 in Building 16.You are very short walk away from a beach, actually 200 steps.On ground floor. Poipu beach is very near.Welcome to Kiahuna Plantation on the sunny south shore of Kauai!. This newly remodeled 2 bedroom, 2 bathroom Kiahuna...
Poipu Kapili 54 - Air Conditioned OCEANFRONT Townhome - Can't beat our views
Located in one of the finest resorts on Kauai, with only 60 units on five beautifully-landscaped acres of Poipu Kapili, this is the perfect home for your family vacation or couples' retreat. The entire home is airconditioned, but also is equipped with screened doors if...
Serene Kauai South Shore Retreat, Full A/C, Walk to Beaches
The moment you step out to the private lanai and take a deep breath, the mind is instantly reset by birds chirping in the trees and the tropical foliage all around. You will appreciate the quiet and secluded vibe, yet with easy access to beaches, shops, restaurants....
Surf Hale, Elegant and Luxurious Surf Retreat
Escape to the breathtaking beauty of Princeville, Kauai, and immerse yourself in the ultimate experience that is Surf Hale. Welcome to our luxurious four-bedroom, 2 1/2 bath vacation rental, where paradise meets comfort and adventure awaits at every turn.Nestled within...
Hale Ohia – Private Gated Luxury Estate with Panoramic Ocean Views
Kauai's Premiere Vacation Rental - "Hale Ohia" This private and gated custom estate is like no other. Four suites with private baths lends this home to have constant ocean views. The exceptional out door living area - "Pai Pai" has 2 large drop down TV's for watching...
Holualoa Studio Cottage - GIANT OCEAN VIEW! Cool, private, near town
We are located on the west side of the Big Island of Hawaii, directly above Kailua-Kona, on the side of Mt Hualalai, in Holualoa, with an awesome ocean and coastline view! Please read our reviews because the view from the cottage lanai is better than we can describe in...
Maui Resort Rentals: Marriott's Maui Ocean Club 2 BR Island View Villa – New Napili Tower
2 Bedroom Island View Villa at Marriott's Maui Ocean Club – New Napili Tower! With its premier location, luxurious accommodatiWith its premier location, luxurious accommodations, and sprawling tropical grounds, Marriott Maui Ocean Club is a perennial Maui favorite,...
Coastal Elegance Across from the Beach
Ekahi 20b is a 1 bedroom / 2 bath, tastefully decorated condo in the LOWER VILLAGE of the Ekahi complex, at the bottom of the hill and closest to the beach. In fact, it's only a 2 minute walk to the world renowned Keawakapu Beach so you can maximize your time there for...
Includes Beach Gear! Top Floor, Golf Course Views! Waikoloa Beach Villas I33
This vacation rental is professionally managed by ResorticaHawaiiWaikoloa Beach Villas I33Please Note: The elevator at Building I is out of order. Parts have been ordered. Repair date is currently pending. Please scroll down for detailed informationBedding...
HiltonPass/Discount Golf/Waikoloa Beach Villas J4
Seasoned Host of 18 years with over 185 five star reviews.*Hilton Waikoloa Pool Pass for stays in 2025! J4 Waikoloa Beach VillasWe extend our Gold Golf Membership benefits at Waikoloa Beach Resort Golf to guest renting our villa.Our villa (J4) is one of the FEW larger...
Oceanfront Penthouse Vistas
Summary:Completely remodeled penthouse 1bedroom 1 bathroom oceanfront condo on the top floor!Located in the sunny and vibrant beach town of Kihei. Beach chairs, umbrellas, luxury beach towels and a cooler are provided to enjoy your day at the beach! We strive to achieve...
Emmalani Oasis - Luxe Designer Home with stunning Mountain Views
Welcome to Emmalani Oasis, a beautiful, professionally designed, luxurious home located in the prestigious community of Princeville. Centrally located, Emmalani Oasis is close to the Princeville Park, Shops, Restaurants, Princeville Shopping Center and a quick drive to...
Stunning Sea to Summit View - Spectacular Remodel Just Completed
Wailea Ekahi Unit 41C is a beautiful vacation condominium in the prestigious area of Wailea, known as the ''sunny side'' of Maui.Full renovation completed in Dec 2023! Our spacious, contemporary condo has two master suites and is perfect for families of four or two...
Mala Hale: Elegant Gardenview Home w/Spa, AC, & Serene Lanai w/BBQ - Mala Hale
Nestled in the heart of Princeville on Kauai’s North Shore, Mala Hale is a spacious three-bedroom retreat designed for relaxation, connection, and a true sense of island life. With vaulted ceilings, lush garden and mountain views, and inviting outdoor living spaces,...
Exceptionally Remodeled Oceanfront, Sunsets, A/C, King bed Hale Kai O Kihei
• Oceanfront• Split A/C units• King bed• Remolded Oct 2021• Beach access from condo complexFully remodeled in September 2021, this bright, beautiful one bedroom, one bathroom oceanfront property in Hale Kai O Kihei 210 welcomes you! This second floor condo is...
Keokis Kona Oceanfront Rental
Aloha! This is Casa De Emdeko's premiere unit. It has been remodeled down to the studs. Everything is brand new and sparkling. Plus this is the only unit that literally is perched on the edge of the Ocean Front Salt Water Pool! No other unit has views like this one....
Spring Discount + Free Night in Hawaiian Luxury above Mauna Kea & Hapuna Beach!
Location: Waimea (Kamuela), HawaiiNestled on the scenic Kohala Mountain Ranch Road, Red 'Ohana offers a serene escape on the 'sunny side' of Waimea/Kamuela, perched above Mauna Kea and Hapuna Beach.Enjoy the quaint charm of Waimea, with its gentle breezes and milder...
Boldly Oceanfront. Stylishly Maui. Royal Mauian 2-Bedroom Retreat
*This is a NEW listing and it's gorgeous! This is not your average beach condo! This stunning 2-bedroom, 2-bath unit at the Royal Mauian is oceanfront living with purpose; fully renovated, thoughtfully designed, and infused with island energy throughout.The decor is...
Single-level, dog-friendly home with a full kitchen, washer/dryer, patio
Puni Mauka | 31- Day MinimumOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Located less than three miles from the ocean, and just a few miles from the heart of town, this secluded,...
Wailea Ekolu Village 1607 - 1 Bedroom Garden View Condo
Wailea Ekolu 1607 is a stunning one-bedroom, two-bathroom vacation rental that offers an exceptional escape in beautiful Wailea. This beautifully appointed condo features calming views of the lush landscapes of the Wailea Blue Golf Course, providing a serene backdrop...
Wailea Grand Champions 104 - 1 Bedroom Golf Course View Condo - PLATINUM
Villa 104 at Wailea Grand Champions Villas is a beautiful Maui vacation rental that offers an exceptional blend of style, comfort, and convenience. This modern and hip condo boasts stunning golf course views and thoughtfully curated interior design elements that create...
Waikoloa Colony Villas 301 - Waikoloa Golf Kings Membership till April 2025!
Welcome to our brand-new vacation rental home. We have a 2 bedroom 2 bath end unit at the Waikoloa Colony Villas located in the Waikoloa Beach Resort. Once you enter the villa, you will be in our great room with brand new furniture, large flat screen tv, one-of-a-kind...
Exclusive, Dream Family Vacation Retreat.
The Royal Palms Estate is perfect for multi-generational families, friends, and groups of fewer than 12 people. Unfortunately, we can not have large weddings or parties. The Royal Palms has 13 Acres Of Exotic Fruit Trees, Tropical Foliage, And Palms. There is 9500...
Ocean View Escape, Walk to Waikiki Beach + 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...
Grand Champions 105 I Spacious Wailea 3bd
Hawaii Life Vacations proudly presents Grand Champions #105, a beautifully updated 3-bedroom condo located in a serene corner of Grand Champions Villas in Wailea. Nestled against the 8th hole of the Blue Course, this spacious retreat offers stunning mountain views from...
Beautiful Beaches ⛱ and Sunshine 🌞 Top Floor Ocean View 😎
Waikoloa boasts sunny days while the views from the lanai never cease to amaze! As you enjoy your morning coffee or evening cocktail from your (381 square feet ) large lanai, you will have great views of the Anaeho'omalu Bay (A-Bay) and Hualalai Mountain (another...
Kauna‘oa 4BR Oceanview Villa with Pool, Spa & Mauna Kea Resort Access
Summary:Experience elevated island living in this luxurious 4-bedroom, 3.5-bath duplex home, located within the prestigious Kauna'oa at Mauna Kea Resort. Just a short walk to the pristine Kauna'oa Bay, this stunning residence offers an exquisite blend of indoor-outdoor...
The Perfect Relaxation & Beach Destination
Our lovely Nihilani Home is situated ideally in the center of the complex, far away from the noise of Ka Haku Road and just steps to the swimming pool and barbecues. And good news, there is now wireless at the pool! This 2,200 SF, 2 story home has undergone a...
Lanikai Ocean Front Duplex Bungalow Private ocean steps. Contact for rates/avail
Location Location Location! Our Lanikai ocean front location exactly in front of the twin Mokulua Islands provides endless hours of outstanding views from the ocean front yard, the living room, dining room, and side deck. A perfect place to work remotely, as you have an...
Peaceful Paradise
New modern studio located between the east and north shore of Kauai. Close to Anahola bay you may hear the calming sound of the ocean at night. Fronting the property is the heavenly Kalalea mountain. The Studio includes A/C, 75 inch flat screen TV, Internet , cable,...
Kailua Oceanfront Villa with Heated Pool & Spa - availability Sept, Oct & Nov
Relax in the beautiful three-bedroom seaside villa in Kailua, where soothing sea waves and soft breezes carry you off. Indulge in the outdoor pool, where you can soak up the sun and relax and end a day of hiking or golf with a massage in the oceanside hot tub. Stay...
Luxury Beachfront & Oceanfront Condo with Panoramic Views • Legal Rental
Looking for the Best Hawaii vacation rental in Maui? Enjoy amazing Maui beachfront views of the Pacific from this spacious, beautifully furnished 7th floor one-bedroom condo at the Mahana on Ka'anapali Beach, rated by TripAdvisor at #1 in the USA and #4 world in...
Hawaii Life Rental Presents Emmalani 423
***Please see construction disclosure at the bottom of the listing.Located within the beautiful Emmalani Court complex on Kauai’s North shore, here you will find yourself surrounded by lush tropical foliage, nearby to breathtaking ocean vistas, world-famous golf Makai...
Hale Manulele near Hanalei
Enjoy our private home in a family friendly, quiet neighborhood on the North Shore of Kaua'i, where the trade winds breeze across the lanai and through the family size house , where bird songs fill the air, and the cloud shows, mountain views with waterfalls, rainbows,...
OCEANFRONT TWO BEDROOM CONDO at SEA VILLAGE with A/C in ALL ROOMS!
Imagine - warm tropical climate, views and sounds of the ocean just out your door, panoramic views, and the perfect accommodations - is there anyway else to experience Hawaii? This two-bedroom, two-bath condominium gives you all of that and more! Comfortable set up with...
Fully Renovated Studio in the Heart of Waikiki – A/C, Wi-Fi, FREE Parking!
Marine Surf #2207 – 364 Seaside Ave.Beautifully furnished contemporary 22nd-floor studio in the heart of Waikiki, fully renovated in January 2025, complete with resort-style kitchenette, comfortable Queen size bed, A/C, free high-speed Wi-Fi, and 1 free onsite parking...
Luxury Nohea Home with Pool & 2 Adjoining Ohanas
Abita Luxury Rentals welcomes you to escape to paradise at this 3,000 sq ft, 4-bedroom luxury retreat in Nohea at Mauna Lani. Thoughtfully designed for comfort and style, this home features a private backyard with a pool and spa, surrounded by lush greenery for a...
Recently Remodeled, Modern, Nice Condo in a Great Location
One bedroom, one bath condo with a great walk in shower. Nice kitchen to save money and prepare your meals. Large tv, fast wireless internet, full size in unit washer and dryer, and a free parking stall. Nice lanai to enjoy your morning coffee, and ac in the unit....
Gorgeous Kapalua Home with Views
This gorgeous Maui home is a two story end unit with expansive ocean views from lanais on each level! Located in the renowned Kapalua resort area on the northern coast of Maui, you are not only close to the beach (less than a 5 minute walk, to be exact), but within...
Aloha Charm on Maui's North Shore - Right by Mama's Beach.
2 rows off the sandy beach in a quiet north shore neighborhood. This property is perfect for family and friends or a couple. 'A breezy and charming home, Maui Winds invites rest and relaxation and offers exciting activities for top-notch athletes ready to windsurf,...
Gorgeous Gated Retreat Near Ocean w Pool & Deck!
Enjoy a blissful vacation at the Heavenly Hawaiian Paradise Beach House. This 3BR/2BA retreat is perfect for groups up to 10, offering welcoming spaces both indoor and outdoor to dine and relax in the beautiful Hawaiian weather. Spacious outdoor deck with swimming pool,...
STUNNING FAIRWAY VIEWS, HOME "E"-CLEAN-NEW-GATED, NEAR JBPHH, CAGE # AVAILABLE.
Welcome to Hillside Perfection overlooking the fairways at Golf Ridge Homes!Discover your ideal fully furnished, 5 bedroom, air conditioned executive home located in central Honolulu. Perfect for leisure visitors, savvy business travelers or visiting construction crews...
Luxury 1BD in ONE ALA MOANA with Beautiful View and Room with Free Parking!!
One of the most luxury condominium in Hawaii. You can experience the best vacation ever in One Ala Moana!!The minute you go inside, you will be astonished the amount of light coming through huge ceiling to floor windows overviewing the city and the mountains. The fully...
Tropical Acreage + Fruit Trees + Beach ~5m drive!
Welcome to "Pua Pono House," on Oahu's captivating North Shore, where country living meets relaxation, away from the hustle and bustle of Honolulu and touristy hotels. Nestled on a lush one-acre estate, our retreat offers a serene and secluded oasis. Centrally located...