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.
New Listing! My Perfect Stays
Kaanapali Shores 732 is a Studio condo with central air conditioning that can accommodate up to 4 guests. Located on the seventh floor, you will find an open-concept layout and tropical-inspired decor with a sense of island serenity. When it's time to rest, unwind on...
Mahana 1117 - Direct Oceanfront - Special Rates!
Mahana 1117 - DIRECT oceanfront in Kaanapali. Located on the 11th floor of the The Mahana at Kaanapali, the full panorama from your lanai captures breathtaking views of neighbor islands - and is a perfect spot for those famed Maui sunsets. Mahana 1117 features: • Fully...
Great Location - Snorkel, Surf & Sunsets!
Beach Villas at Kahalu’u is right across the street from the best snorkeling beach on the Big Island! See green turtles and reef fish! The ground floor condo has 2 bedrooms, one with a king bed, the other with twin beds, and 2 bathrooms, each connecting. There is a...
Oceanview Retreat in Puamana – Steps from the Beach & Surf
Nestled just a 30-second walk from the beach and three popular surf breaks, this beautifully remodeled 3-bedroom, 3-bathroom townhome in Puamana offers the perfect blend of modern comfort and laid-back island living. Located on the safe side of Puamana, untouched by the...
13th Floor Waikiki Shore - Ocean-front / King Bed / AC
Welcome to Waikiki Shore – Your Perfect Oceanfront Escape!Located in the heart of Waikiki, this stunning 1-bedroom, 1-bathroom condo offers unbeatable ocean views and direct access to the world-famous Waikiki Beach. With modern amenities, a prime location, and a...
Beautiful Pali Ke Kua Garden/Mountain View Condo w/AC & Beach access!
Your Kauai adventure begins at this terrific 2-bedroom condo. Absolutely the best location in the heart of Princeville...can you say paradise!This condo is beautifully decorated with high end furnishings to help you relax while you take in commanding garden and...
Paia Family Cottage - Walk to everything in Paia Town
Walk to everything in Paia Town. Paia Family Cottage is well equipped, with comfortable indoor, and sweet outdoor living spaces for everyone. There is AC in all bedrooms and living room. And a yard where kids can play, with views out over the green sugar cane fields....
Fantastic Hana Bay Oceanfront Location! 5-Minute Walk to Hana town & beaches!
AUTHENTIC HAWAIIAN BEACH HOUSE ON HANA BAYManini Cottage captures the relaxed comfort and charm of a true Hawaiian beach house in a rare and secluded oceanfront setting. Perched at the edge of Hana Bay, this one-bedroom, one-bath cottage features open-concept living, a...
Luxury Ko Olina Oceanfront Villa O1105 w/ Stunning Ocean Views near Golf Course
Welcome to the luxurious beachfront retreat of Ko Olina Beach Villas O1105, a spacious 3-bedroom villa set within the exclusive Ko Olina Resort in Kapolei. Sweeping ocean views, an open-concept layout, and direct access to lagoon pathways create an effortless blend of...
*Affordable Island Getaway with private yard *
We're situated in a prime residential neighborhood, just 2 blocks away from Kailua Beach Park Entrance and Kalapawai Market, as well as downtown Kailua. You'll find an abundance of shops and restaurants, plus two of the world's most beautiful beaches, Kailua and Lanikai...
The Blue Tide House: Steps to Maui beaches + nearby eats
Experience the best of Kihei, Maui from The Blue Tide House, located within the popular Kihei Kai Nani condos! Located on the first floor near the pool. Just steps across the street from the island's beautiful beaches, you can easily enjoy the sun, sand, and surf. A...
Ocean Front Dream Suite- Spectacular Views! 2Bedrooms/2Bath Steps to Amenities!
Wake up to unforgettable views and the soothing sounds of the ocean waves a few steps away! Build your book of Maui memories and support the economic recovery of Maui, owners and their teams! This is where you will find relaxation and inspiration for adventure! This...
Liko Lehua Cottage in Volcano - Hot Tub & Fireplace - Mauna Loa Estates
Liko Lehua Cottage - Your Hawaiian Forest Retreat!Escape to the enchanting Liko Lehua Cottage, a hidden gem just six minutes from the awe-inspiring Hawaii Volcanoes National Park. Nestled in the lush, serene Hapu'u forest of Mauna Loa Estates, this newly reimagined...
Brand New! Luxurious Sky Ala Moana 2 Bed 2 Bath
Summary:*30 DAY MINIMUM* Discover the lively heart of Honolulu and enjoy leisurely walks along the beach with this 2 bed and 2 bathroom apartment on the 16th floor of Sky Ala Moana. Get a charming view of the city and take advantage of the convenience of being close to...
Kaanapali Stunner - Spectacular Ocean Views
Updated 2025 - New Furniture and flooring. New pictures soon.As owners, we are committed to providing a high quality safe and clean vacation experience for both first time and loyal guests of Whaler 559. This unit is highly upgraded with loads of extra amenities and...
Rare Beauty and Luxury at Kealakekua Bay
Your hosts Tammy and Joe are committed to providing a 5-star experience. The home is maintained in immaculate condition with the highest levels of spotless cleaning before you check in. The property is very private with secure gated access. Parking at the guest house...
Oceanfront Beachfront Escape Hale Kai 1Bed
Discover charm and comfort in our ground floor vacation rental, nestled by the pool and oceanfront. Immerse yourself in stunning sunsets just steps from the water. This cozy unit boasts a fully equipped kitchen, a luxurious king-size Tempur-Pedic bed, and a sofa sleeper...
Oceanfront Cottage in Scenic 'Old Hawaii' - Off-Grid, solar-powered property
The Original Rainbow Dreams Cottage - with a spectacular oceanfront view - is the only vacation rental so close to the ocean on the scenic Old Red Road (Rural Route 137) in the small village of Opihikao. The cottage is Off-Grid with limited (ATT) only cell service....
Oceanview King Studio | Maui Banyan, Walk to Beach
Aloha from Midway Vacations, your local experts in paradise! Enjoy spotless, well-kept homes, island hospitality, and 24/7 support for a worry-free Hawaiian escape.Enjoy your Maui getaway in this top-floor Maui Banyan studio featuring ocean views from your private...
Three bed three bath luxurious townhome in gated Princeville community
3 Bedrooms, 3 Baths, Sleeps 6VILLAS ON THE PRINCE #2 is a luxurious 3 bedroom, 3 full bath townhome in one of only 3 gated communities in Princeville on Kauai’s beautiful north shore. Newly renovated, it is one of the only units offering A/C upstairs as well as in each...
Maui Kamaole B101 - Gorgeous designer condo! Modern luxury and great rates!
Condo was fully renovated, new cabinets, tile floor, granite countertops, stainless appliances and new A/Cs. The Master Bedroom boasts a California King bed, ensuite bathroom, and private courtyard. The modern kitchen is very well stocked and you will enjoy the Weber...
LUXURY VILLA, 3 Private Suites, Pool/Spa, Gym, Central A/C, Beach
This exquisite Villa has it all! Located in The Villas at Poipu Kai boutique development. With 1900 s.f. living area, this three bedroom three bath view unit features an expansive covered lanai, private elevator access, central air, central vacuum, washer/dryer, and...
5-Star Reviews! All Remodeled! Split Air! Quiet Building 5! Ocean/Garden View!
We are a 2-3 minute walk to beautiful Kamaole Beach III. Our building is located in quiet building 5 on the 2nd floor. Our unit is close to the elevator but far enough away to not hear it. Additionally, there is a beautiful ocean view from our lanai!The remodel of our...
Gorgeous Oceanfront! - Sweeping Views & Steps to the Beach
Welcome to our oceanfront home away from home! You'll find views straight out to the ocean and the wild coastlines of Kapalua. The villa is perched above the sweeping white sands of Oneloa Beach and is steps away from three other world-renowned beaches. Our...
Maui Kamaole One Beachfront Condo at Charley Young Beach
Discover your perfect Maui beachfront getaway at Kamaole One #9, this beautiful 2-bedroom, 2-bath oceanfront vacation rental located directly on Charley Young Beach, the north end of the world-famous Kamaole I Beach Park in sunny South Kihei.This rare oceanfront condo...
Luxurious, 2 bedroom / 2 bath, FULL Ocean View Wailea Condo
Situated on 18 acres of perfectly manicured tropical foliage, bordering the award winning Wailea Blue Golf Course, Ekolu Village is an exclusive and desirable complex that is exceptionally quiet and free of any traffic noise. This property is located in less than a 5...
Edge of Cliff Luxury Penthouse over Largest Coral Reef in Hawaii - Beach Access & AC
Very large penthouse with 2, 000+ square feet of living space under roof, vaulted ceilings and the most incredible views over the largest coral reef in the State of Hawaii. Ocean views available throughout the condo's living area and into the huge master bedroom suite....
Golf Course Serenity at Turtle Bay, near beach
Escape to our serene, ground-floor condo nestled along the scenic Turtle Bay Golf Course. With captivating views and a prime location near Turtle Bay Resort, beaches, and dining, it`s the perfect retreat for couples, adventurers, and business travelers alike.Split...
Hale Hihimanu - newly renovated house and guest cottage with AC
Hale Hihimanu - a newly renovated house and guest cottage with AC throughout. Located on a private driveway with just two neighbors, this property offers unprecedented privacy for a home in the resort community of Princeville. The beauty and elegance of this property...
Luxury Villa: Hilton Pool Passes, Renovated, Private Beach Club, Sunset Views
Enjoy staying at the best location at Golf Villas, featuring ultimate privacy with breathtaking sunset views and unlimited access to a private beach club and unlimited access to the Hilton Pool for 6 people. Our well-appointed and recently renovated villa is located in...
Kaanapali Alii | 265
Kaanapali Alii 2652 Bedrooms | 2 Bathrooms | Sleeps 6 | Ocean View________________________________________Welcome to Kaanapali Alii 265, your dream vacation rental in the heart of Maui’s renowned Ka'anapali Beach. This luxurious two-bedroom paradise combines modern...
🏖️Walk to Keiki Beach! Spectacular Oceanfront | Unbeatable Views & Location | vrKCV
vrKCV - Kona Bay Estates 23, Professionally Managed by Kona Coast VacationsSpectacular Oceanfront Retreat with Unparalleled Views!Indulge in the ultimate island lifestyle from this oceanfront home, where breathtaking views of the Pacific Ocean greet you daily. Imagine...
Welcome to 3 Luana Garden Villas 1A,1C& 1D Oceanfront resort Partial ocean Views
Kaanapali Luxury Vacation Rentals welcomes you to our beautiful Luana Garden Villas at the Honua Kai Resort.This listing is for “three” separate neighboring villas, which is perfect for a multi-family vacation. Luana Garden Villas is the final phase of Honua Kai Resort...
Highest Guest Rating at Mana Kai, Best Ocean Views, Luxury Amenities, Ocean End
THE TOP-RATED, 5-STAR LUXURY VACATION RENTAL CONDO AT MANA KAI WITH DIRECT OCEAN VIEWS ON KEAWAKAPU BEACH:This is the one! Mana Kai Unit 402 is a newly remodeled luxury condo with direct beach and ocean views available at the Mana Kai Maui Resort. This premier condo is...
Private Luxury Estate w/Pool, Jacuzzi, AC & Ocean Views: Ohana Le'ale'a
Step into the beauty of island life at Ohana le'ale'a, a newly built 3-bedroom, 3.5-bath luxury estate in Kona that blends expansive indoor-outdoor living with sweeping Pacific views. With 3,180 square feet of refined design, a private pool and spa, and a game room...
KV E609 Remodeled 2Bedroom Condo w Pool AC Near Beach
Kahana Villa E609 Bright Blue Ocean Views from Remodeled Island Style 2Bedroom Condo in Kahana Across Street From Beach! Island Living with Conveniences of Home FREE daily activities included with your stay value up to $570! Complimentary admission, every day of your...
- Luxury Vacationing Modern Condo - Spring Specials -299 USD-
***The pool has just been renovated and it is gorgeous*** DESIGNED BY A NYC ARTIST. THIS BEAUTIFUL CONDOMINIUM IS BORDERING KIHEI AND WAILEA IN SOUTH MAUI, HAWAII. IT IS LOCATED AT THE GORGEOUS MAUI HILL RESORT BY ASTON. THE PROPERTY HAS BEAUTIFUL GARDENS, SWEEPING...
Oceanfront HK-B7 - Maui Condo on the Beautiful Serene Beach of Ma’alaea Bay
Experience the ideal beachfront getaway at Hono Kai B-7, a charming condo nestled in the serene beauty of Maui. This idyllic retreat offers stunning ocean views from the living room, bedroom, and lanai, providing a picturesque backdrop for your vacation. The...
Heartwarming 2-bedroom condo in Lahaina
Experience Lahaina like a local in this 2-bedroom condo. The space is excellent, with 1 king bed and 2 twin beds (along with Sofa Bed and Additional Bed in Primary Suite) to accommodate guests. This welcoming property offers a relaxing stay for all travelers. Our place...
Panoramic Ocean & Mountain Views --we have FULL AVAILABILITY please message us.
Let the Aloha spirit be with you during your Hawaii visit by staying along the famous Koolau Mountain range on the lush Windward Side of Oahu. With 3900 sq. ft. of space to relax and enjoy a panoramic view of the grand mountains and the peaceful ocean as a backdrop,...
Ho'olei Ocean View 21-6 Newly Listed, Renovation May 2025
Remodel completed June 2025! See the new photos just posted!The entire home has been repainted, almost all the furniture was replaced, a lot of new beautiful art was added, and all new hardwood French oak floors were installed in the bedrooms.. We also remodeled the...
Luxury Oasis Palm Villas at Mauna Lani - Golf/Beach/Shops/Restaurants
Luxury Oasis at Palm Villas in Mauna Lani Resort on the Big Island of HawaiiWelcome to your dream Hawaiian getaway at the Palm Villas located in the Mauna Lani Resort, where paradise meets perfection! Nestled within the prestigious Palm Villas community, our luxurious...
Breezy Pool Oasis 5BR AC Ocean Views 5min to Beach
Welcome to your tropical paradise getaway! This resort-like 5 bedroom home with swimming pool, hot tub, waterfalls, and stream is ideally located in a quiet cul-de-sac and offers the perfect blend of relaxation, comfort, and breathtaking ocean views. With Magic Sands...
Tropical-inspired decor with partial ocean view
Kuleana Resort 313 is a charming 1-bedroom, 1-bathroom condo that comfortably accommodates up to 4 guests. The spacious bedroom features a (new as of Dec 2025) California King firm hotel quality bed complemented by 1 window A/C unit for added comfort. Additional...
3 BR Oceanfront Villa: Marriott's Lahaina Tower; Jan 9 - Mar 6th, 2027
Spend up to 8 consecutive weeks in the same 6th floor oceanfront villa within Marriott Ocean Club Lahaina Tower! ONE WEEK JUST BECAME AVAILABLE!!!Availability 1/24/26 through 1/31/26Can also be rented weekly. All weekly rental reservations must begin on a Saturday and...
Hale Hahalua - Serenity and Ocean Views in Kona now with upgraded A/C in bedr.
Aloha! Welcome to Hale Hāhālua – the gateway for your dream vacation on the Big Island of Hawai’i. Located in the picturesque community of Keauhou (Kailua-Kona), right above Keauhou Bay, our condo offers you the perfect starting point for your adventures. In Hawaiian,...
Kona Coast, BEST Oceanview&Pool, Yoga/Meditation Space, Pickle Ball&Basket Ball
Welcome to Halani — Your Serene Sanctuary on the Big IslandEscape the busyness and crowds of the resort scene and discover Halani, meaning “heavenly breath”—a peaceful retreat perched above the South Kona coast, offering one of the most unparalleled ocean views on the...
New Listing! Tropical-themed 7th floor studio
Kaanapali Shores 721 is a Studio condo with central air conditioning that can accommodate up to 3 guests. Located on the seventh floor, you will find an open-concept layout and tropical-inspired decor with a sense of island serenity. When it's time to rest, unwind on...
Mau Loa Hale: Perfect Location 5 Acres Walk to Bch! Open concept! Breeze & Views
Welcome to Mau Loa Hale, a private island-style retreat on five acres between the Koʻolau Mountains and the Pacific. Here, dramatic ridgelines meet ocean breezes, creating a peaceful escape where you can spread out, recharge, and experience Oʻahu at a slower rhythm....
TRUE OCEANFRONT PARADISE! Royal Mauian #311
ALOHA!Welcome to Kihei, Maui and your oceanfront paradise! Our incredibly beautiful condo is near the center of the building and only steps away from the water. Watch whales, savor the sunset and enjoy the sound of the waves from the large lanai, the living room or even...