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.
Stunning Luxury Estate 🌺 Superb Private Lanai & Breathtaking Sunsets! 🌅 Keauhou Luxury Estate
Experience island lifestyle in one of Kona's most desirable gated communities: Keauhou Estates.Amazing home with 3 bedroom with 3 and 1/2 baths. Beautiful great room, dinning room and gourmet kitchen overlook the pool to the ocean beyond. Imagine a beverage and sunset...
Hawaiian Luxury at Mauna Lani Point J105n1-bedroom 1.5 Bath @ Mauna Lani Resort
Get ready to relax in this fabulous 1-bedroom condo in Mauna Lani. This terrific property features a king bed, and a day/child bed, along with 1.5 bathrooms. The primary bathroom has a large walk in shower and a Japanese soaking tub. The living room offers an additional...
Spacious 3 Bed 2.5 Bath House in Kahakai Estates
Please note, effective Jan 1st. 2026, Hawaii's Transient Accommodations Tax will increase from 10.25% to 11% for all stays with an arrival in 2026 forward. We may need to collect the tax difference to secure and finalize your booking. We will contact you to confirm the...
2 Bed 2 Bath Surfing & Snorkeling in Kahaluu Bay
Aloha! Come and stay at the Hale Hamoa created for everyone with everything we love about Hawaii. Only 1 minute walk to one of the best snorkel beaches on Kona Side and the Surf school next door. The condo comes with all the essentials you need for an awesome vacation...
Beachfront Spectacular Ocean views , steps to white sand Beach & walk bike Path
Listen to the sound of the waves from this beautifully furnished corner unit and admire the views up and down the coast from the spacious lanai. Upgraded with granite countertops and travertine floors in kitchen and bathrooms. Unit 219 is very private with unobstructed...
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: •...
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...
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 Ko Olina Beach Villa O1105 by Gather, a luxurious 3-bedroom, 2.5-bathroom retreat nestled in the heart of the stunning Ko Olina Resort in Kapolei, HI. This villa is designed for up to 6 guests and offers an exceptional blend of modern comfort and breathtaking...
*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...
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...
🌴Alii Villas 109 Newly remodeled. Easy access to pool and parking 🌴
Monthly rates available until October 1st This newly remodeled ground floor one bedroom condo is perfect for your island getaway. Comfortably furnished and well equipped, just bring your suitcase Short walk to your parking space and pool area.Perfect for visitors with...
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...
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...
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...
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....
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
Welcome to your dream vacation rental at Kaanapali Alii! This luxurious two-bedroom paradise is the perfect destination for your Hawaiian getaway. Nestled in the heart of Maui's renowned Kaanapali Beach, this spacious rental offers a blend of comfort, convenience, and...
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...
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
FREE daily activities included with your stay value up to $570! Complimentary admission, every day of your stay*: Whale Watch (seasonal), Dinner Sunset Sail, Snorkel Sail, Alpaca Farm Tour, Pineapple Farm Tour, and All Day Electric Bike Rental. (W1)*One ticket per...
- Luxury Vacationing Modern Condo - Spring Specials -299 USD-
***The pool has just been renovated and 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 VIEWS...
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...
Panoramic Ocean & Mountain Views -
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
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...
Beautiful Condo with Great Calif King Bed, Great location & all new appliances
Ocean/Mountain/Garden/Views, Great Calif King Bed Aloha! Welcome to our beautiful, fully renovated vacation condo.PLEASE NOTE THAT ALL BARBEQUES HAVE BEEN REMOVED FROM EKAHI AND THEY ARE ILLEGAL ON ALL CONDOMINIUM BALCONIES AND LANAIS. WE WILL BE CHANGING OUR LANAI...
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 luxurious California King bed, complemented by 1 window A/C unit for added comfort. Additional sleeping arrangements include a...
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! Availability 1/9/27 through 3/6/27Can also be rented weekly. All weekly rental reservations must begin on a Saturday and depart on a Saturday.This 1700...
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...
New Listing! Tropical-themed 7th floor studio
Kaanapali Shores 721 is a Studio condo with central air conditioning that can accommodate up to 2 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
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Welcome to Mau Loa Hale, a private...
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...
Spectacular Panoramic Ocean Views - Private Ohana
Live like a local at the Ocean Blue Ohana. You'll have the entire private first floor of this amazing Hawaiian pole home on a half acre property in South Maui. As you enter the space, you will be drawn to the sweeping panoramic ocean views. You are sky-high, perched 500...
Aloha Condos, Kanaloa at Kona, Condo 3703, Oceanfront, AC
1700 Square feet of breezy vaulted-ceiling living space, with new tile floor and paint throughout. Refinished koa wood cabinetry in all new kitchen. Ceiling fans in all major rooms and lanai (5). Powerful whole house ventilating system reduces demand for AC. High...
Waikiki Shore Beach Front Studio
Large beach front studio (460 sq, ft,) located at the Waikiki Shore, the only condo building in Waikiki that is directly on Waikiki Beach. This unit is located in a building that is within the designated Resort Zone, and therefore eligible for short term vacation...
Waikoloa Village Golf Course Fairway 2-bedroom condo with Central AC-WiFi, Views
Waikoloa Fairways -From the Summit of Mauna Kea to the Kohala Coast Line, Welcome to Paradise! Central Air Conditioning! Aloha! E Komo Mai! This gorgeous condominium offers everything you need for your Big Island getaway. Located in the highly sought after community of...
Renovated 03/23! Direct Oceanfront Condo with 2 Master Suites!
*Available for booking! Thankfully, our condo is not located in the wildfire affected area*Enjoy stunning views in this newly renovated oceanfront condo located on Kahana Beach! This spacious 1,040 sqft condo located at Valley Isle Resort has been completely renovated...