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.
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...
New Listing! Ekahi 26B-Spacious & Family Friendly | Ground-Floor Garden Oasis
Ground-Floor Garden Oasis | 1BR/2BA Wailea Ekahi Condo | Walk to Keawakapu Beach & PoolsDiscover the perfect blend of island charm and modern comfort at Wailea Ekahi 26B. This remodeled, ground-floor condo offers a spacious 1-bedroom, 2-bathroom layout surrounded by...
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 I33Bedding Configuration:Master Bedroom: King BedGuest Bedroom: King BedAdditional Bedding: Sleeper Sofa in the Living RoomAmenties:Beach Equipment: All of our vacation rentals...
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 2026! 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 luxurious...
Keokis Kona Oceanfront Rental
If your dream of Kona is coffee at sunrise, waves in stereo, and sunsets so close they warm your cheeks—this is the place. Keoki’s Kona Casa sits right up front at Casa de Emdeko on Aliʻi Drive, with an L-shaped lanai essentially hovering above the oceanfront saltwater...
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...
Keaau Apartment on Beautiful Acre w/ Pool & Deck!
Spectacular outdoor adventures await when you stay at the ‘Hale Ho'okipa,’ a peaceful vacation rental in Keaau. Complete with an outdoor pool, deck, and 1-acre yard, this apartment offers an authentic Hawaiian experience far from resorts. Explore Kaumana Caves, take in...
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. Come and explore our Island of Hawaii, from Mauna Kea snow-capped mountain to Hawaii Volcanoes National Park where you...
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...
Lanikai Seashore by Gather: Oceanfront Home w/ Mokulua Views, AC & Lush Yard
Lanikai Seashore at 1270 Mokulua Drive is a stunning beachfront sanctuary in Kailua, HI, where you can experience the vivid beauty of Lanikai Beach just beyond your backyard. This luxurious 2,100 square-foot retreat artfully blends comfort and style, featuring exquisite...
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,...
DELUX family friendly accomodations in charming Princeville.
Get ready to relax in this terrific 2-bedroom condo in Princeville. This serene retreat offers a king bed, a twin bed, and two bathrooms with master bath with a jetted bathtub. Enjoy the additional living space with a cozy sofa bed. Take advantage of the fitness room,...
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
Mahana 708 at The Mahana at Ka'anapali Beach, Lahaina, MauiLooking 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,...
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, Firepit on 1+ acre!
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...
licensed NUC no 90/TVU-0326 Serenity Beachfront Cottage
Charming beachfront cottage right on Kailua Beach! licensed NUC no 90/TVU-0326 Serenity Beachfront Cottage. This delightful 2 bedroom/1 bath vacation rental cottage puts you right in the middle of world renowned Kailua Beach. Enjoy ocean views from your living room....
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...
Ho'olei Villa 17-1: Luxury Retreat with Breathtaking Ocean Views
This property is hotel zoned, and not being affected by the recent proposed legislation.Luxury at its finest! Ho'olei Villa 17-1! Mesmerizing ocean views and bright open floor plan welcome you. Enjoy the beautiful Maui sunsets on your expansive private lanai.One of the...
Waipouli Beach Resort E301 2 Bdm, 3 Bath - Beautiful Sleeping Giant Mtn View
Waipouli Beach Resort E301 2 Bdm, 3 Bath - Beautiful Sleeping Giant Mtn View and Peek Oceanview!SLEEPS UP TO 7! This Luxury Condo Offers Guests a Gorgeous View of Sleeping Giant Mountain and peek ocean view from the lanai. This Condo is a 2 Bedroom, 3 Bathroom Condo at...
Hale Malulani - Luxury Oceanfront Puako Villa with Pool, Hot Tub & Pickleball!
Immerse yourself in the unparalleled luxury and breathtaking beauty of Hale Malulani, an exquisite oasis nestled in the serene shores of Puako, now gracing the rental market once again, following a meticulous and extensive renovation. This exquisite property proudly...
Penthouse Waipouli Beach Resort E404 - Beautiful Ocean & Pool View
Penthouse - Ocean & Pool View 1 bedroom "Jewel" - ACExperience your vacation in this Beautiful Ocean and Pool View, a 1 bedroom, 2 bath condo "Jewel" in this Oceanfront Resort & Spa. From the moment you walk into the living room and master bedroom you will know you made...