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 Fairways 603: Luxe 2BR Home w/ Modern Comforts, Jacuzzi & Lanai Views
Escape to comfort at Mauna Lani Fairways 603, an elegant retreat in Hawaii’s lush Mauna Lani Resort, where recent updates and thoughtful details create the ultimate island sanctuary. With two bedrooms, two and a half bathrooms, and space for up to six guests, this...
Come & stay with us at the beautiful & peaceful Bird's Nest
The Bird's Nest is located in a peaceful neighborhood that is surrounded by lush greenery and bird songs can be heard throughout the day & tree frogs at night. The house sits high above the ground which makes it feel as if you are staying in a tree house. The road in...
Recently Fully Renovated-Oceanfront, Top floor, Million Dollar View, Sleeps - 2
Our newly renovated condo #310, is on the top floor. Enjoy the 3rd floor with NO noise above you, directly over beautiful Wailua beach. "Fall asleep to the sounds of the crashing waves" The condo is located on the quieter end of the building, away from Main Street. From...
Spectacular View, Direct Oceanfront Kona, Top Floor
ALOHA, WE INVITE YOU TO RELAX AT SEA VILLAGEOur lovely top floor condo is perfect for you! Sit back and take in the spectacular view from the lanai as you watch dolphins and whales (in season) during the day and beautiful sunsets in the evening! Lose yourself in the...
DIRECT OCEAN FRONT 2Bd/2Bath Whaler on Kaanapali Beach
Discover our beautifully spacious 2 bedroom, 2 bath Direct Ocean Front condo at The Whaler #1102. This particular home is a rare and sought after condominium, located on the north corner of Tower I. It’s 11th floor location offers an unobstructed northern view from...
Pipeline Beach*Studio Large*AC*wifi*Free Pk*Steps To White Sand Beach*30nite min
The studio has a TV with cable, internet connection, air conditioner, a full kitchen with an oven and stove, a refrigerator, microwave, toaster, blender, coffee maker, plates, pans, and other eating utensils. The studio is very clean, very comfortable with soft sheets....
Beautiful Condo Across the Street from Beach w/ Ocean View and Great Snorkeling!
Kahalu'u Beach Park is a prime spot for snorkeling, surfing and relaxing on the sandy beach. The beach is literally right walk across the street. Enjoy amazing ocean views from your private lanai, a spectacular infinity pool, hot tub and bbq area. This meticulous 2...
LUXURY F205 - VIEWS INCLUDES GOLF DISCOUNTn 2 Bdrm 2.5 Bath 5 MIN walk to BEACH
This luxurious and completely remodeled 2nd Floor unit offers GOLFERS STAYING IN THIS UNIT GREAT DISCOUNTS FOR GOLFING with our Gold Membership @ WAIKOLOA BEACH, KINGS & LAKES COURSES. ALMOST ½ OFF!!Our complex has a large HEATED, SALINE outdoor lap POOL and 2 Hot...
3BR/3BA Villa: Central A/C! Short Walk To Beach!
Welcome to BlueTideVillas! This unit not only boasts among the BEST reviews in all of Kauai but is also newly upgraded to enhance your stay from April, 2024, onwards.Nestled in the heart of Poipu, this VERY spacious (1830+ square feet) villa is a newly remodeled and...
OCEAN FRONT 2bd/rm Townhome New Remodel Ocean and Sunset Views AC Pickleball!
Aloha, we would love to have you as our guests! It is a pleasure to know you are interested in our Ocean front 2 bedroom/ 2 bath townhouse. We have had a tremendous amount of positive reviews, but decided to update the property to provide an even better guest...
Kumulani B4 Best Ocean Views in Complex, Amenity Pkg Optional.
Surround yourself with the luxury, elegance, and all the amenities of two of the world's finest resorts - The Mauna Kea and The Westin Hapuna Beach Resorts.This 2 BR 2 bath second floor luxury condominium is located in The Uplands of the Mauna Kea Resort and is accessed...
Updated End-Unit Oasis, 3 Bd + Loft & 2 Ba, Pool, Walk to Beach, AC Coming Soon
Welcome to our private tropical oasis! This newly updated 1,478 sq. ft. end-unit offers the perfect retreat. Surrounded by lush tropical plants, you’ll enjoy privacy and tranquility, with no neighbors above or below you. The home features massive wood beams and large...
Gorgeous Kapalua Oceanfront with Stunning Views
Wake up to the sound of waves and breathtaking views of Molokai across the channel from this beautifully appointed oceanfront villa. Perfectly situated on the dramatic cliffs of Kapalua, this ground-floor condo (1500+ sq. ft.) offers front-row access to Maui’s most...
Escape to Paradise at Beautiful Maui Kam In South Maui!
Our Hearts go out to the people, families, friends and loved ones of West Maui. Maui Travelers, please consider giving extra patronage to the small businesses, restaurants and services that are open throughout Maui that employ so many who are affected with personal...
5 Bed 3 Bath Home in Poipu Kai
Hale Aouli is a beautiful newly renovated five-bedroom and three-bathroom custom home located in beautiful Lanai Villas in the Poipu Kai Resort. From the home, you will find walking paths to Poipu's finest beaches, restaurants, tennis courts, pool,...
"Sea Gem" a Oceanfront Condo at Lae Nani 515
"Sea Gem" A Oceanfront Ground Floor 2 Bedroom | 2 Bathroom at Lae NaniPanoramic views at Lae Nani of Wailua Bay await in this sunny condo located along the island's east shore. Situated just steps from the shoreline, the sights and sounds of the waves are palpable from...
Seaview Maui – Family Vacation Home in Upcountry Maui
Maui County Rental permit - STPH 2014/0004TA-097-868-8000-01 / GE-097-868-8000-01TMK-270031100000Welcome to Seaview! This is a unique family style vacation home, offering space for up to ten family members or friends to vacation together, with considerable privacy....
Waterfront condo with shared pools, private beach, balcony, W/D, and AC
Casa De Emdeko A317Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Perched on the top floor, this stunning 2-bedroom, 2-bathroom condo in Kailua-Kona offers sweeping ocean and...
Stunning ocean view! 2/2 in the heart of Wailea
Beautiful, spacious, modern 2/2 condo located in the heart of the Wailea Resort area with gorgeous, far-reaching ocean and island views, and surrounded by brilliant, lush, flowery grounds. Super-close to dining, golf, shopping, and only a short stroll to award-winning...
Wai'ula'ula 330 - Upcountry Oceanview Residence
This discerning, upcountry, oceanview residence offers a great room with sliding glass pocket doors that invite indoor/outdoor island living; a chefs' kitchen outfitted with slab granite countertops and premium stainless steel appliances (including a wine refrigerator);...
Breathtaking View on Beautiful Sandy Beach Oceanfront
This Oceanfront Condo has an amazing view. It has a gorgeous Great Room and a beautiful fully equipped kitchen. With the roar of the ocean just a few yards away, you will not want to leave the Lanai after relaxing on the Tropitone furniture.This Condo has a beautiful...
Luxurious Ground Floor, Perfect Family Spot, Private Lanai, 1 Min to Pool/Beach
Hokulani 142, Honau Kai Resort, is a fabulous ground floor unit with a beautiful private lanai and garden area. Our lanai extends out to an open grass area which many of our guests use to relax, play games, or enjoy the quiet surroundings. There are no elevators exiting...
Hale Makani Nui: Sea-View Hilltop Villa Near Beaches
This lovely hilltop villa, Hale Makani Nui, or House of Strong Wind, is delightfully elevated, in every sense of the word. Its picturesque placement at the crown of a gently sloping lot gives an enchanting estate-like feel to the entire property, while also providing...
Includes Beach Gear! Spacious lanai with resort views. #2 Shores at Waikoloa
This vacation rental is professionally managed by ResorticaHawaiiShores at Waikoloa Villa 2Please scroll down for detailed informationBedding Configuration:Master Bedroom: King BedGuest Bedroom: 2 Queen BedsAmenities:Beach Equipment: All of our vacation rentals...
Whaler on Kaanapali Beach Oceanfrnt 2 Bdrm April openings! Whales Whales Whales!
Breathtaking views of Black Rock, Molokai, and Lanai - Whaler 552 is a beautiful 2 bedroom, 2 bathroom suite located oceanfront at The Whaler on Kaanapali Beach. Enjoy year-round sunset views and seasonal humpback whale watching right from your own lanai! Just steps...
Maui Resort Rentals: Honua Kai - 4 Total Bedrooms, Stunning 3rd Floor Ocean Views!
This unique offering combines two neighboring 3rd-floor two-bedroom suites to create an exceptional 4-bedroom package that is perfect for large families or groups. Located only one stack back from oceanfront, Konea 303 provides stunning views of the blue Pacific Ocean...
PERFECT Maui Getaway! Wailea Ekolu Luxury Ocean View Top Floor Condo
Welcome to ocean view luxury in the heart of Wailea; welcome to your perfect Maui getaway. This 2 bedroom, 2 bathroom renovated condo in the Wailea Ekolu neighborhood gives you all the amenities of home, combined with all the luxury of a resort, and all within a 15...
Resort getaway with views of Hanalei Bay, pools & tennis
Hanalei Bay Resort 4204/5Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Hanalei Bay Resort 4204/5 is an air-conditioned condo, featuring two bedrooms, two bathrooms, kitchen, living...
Secluded home with spectacular ocean and sunset views
Kihei's Hidden Gem (B&B permit #BBKM20210002)offers an ideal setting for your family or group to experience a memorable Hawaiian getaway. This brand new south Maui vacation rental boasts ocean, mountain, and sunset views, a private pool, central air conditioning, and a...
Oceanview 1 Bedroom at Lawai Beach Resort, modern and updated!
Our newly updated ocean view condo on the 2nd floor of Lawai Beach Resort is ready for you!Recently updated with chevron flooring, new bathroom vanity, refreshed kitchen cabinets (new appliances coming in October), all new furniture...we are ready to host you!Lawai...
It's Special - This Award Winning Designer Masterpiece is Phenomenal!
Kauai Haven is nestled within a classic Hawaiian style backdrop, resting on the edge of a bluff overlooking the spectacular Pacific Ocean. An award-winning designer, who is part of the Coastal Living Network of designers, has designed this exquisite condo that offers...
Ocean View. Hilton Waikoloa Pass for 2025. B305 Vista Waikoloa
Vista Waikoloa B305. Ocean Views!This vacation rental is professionally managed by ResorticaHawaiiPlease scroll down for detailed informationHilton Pool Pass: Valid for stays now through December 31, 2026. Maximum 6 persons per pass (children under the age of 5 are not...
Beautiful Condo in Kihei Alii Kai, steps from Kam 1 beach
Welcome to our bright and beautiful condo, ideally situated near the front of the complex—just steps away from the beach! Thoughtfully upgraded with new furniture in Summer 2022, this is the only condo we own, and we’ve equipped it with all the comforts needed for...
Stunningly Renovated! Ocean View! Elua 2305
This property is hotel zoned, and not being affected by the recent proposed legislation.Welcome to Elua 2305. Your ultimate Maui vacation awaits at this fabulous listing! Don’t miss this incredible opportunity to enjoy the very best that Maui has to offer.Say Aloha to...
Gorgeously Updated - Kihei Surfside #113 - Groundlevel Oceanfront Condo
Kihei Surfside #113 – Fully Renovated Ground-Floor Ocean View Condo with A/CEnjoy comfort, convenience, and coastal beauty at Kihei Surfside #113—an ocean view, ground-floor condo that underwent a complete renovation in May 2022. Located steps from the water’s...
Maui Resort Rentals: The Whaler 1061 - Upgraded 10th Floor Studio w/ Stunning Pacific Ocean and Mountain Views!
Perched high above the palm fronds, guests are treated to unobstructed views of the tranquil blue Pacific and the soft sands of world-renowned Kaanapali Beach from this luxurious 10th-floor studio suite. Fold away the floor-to-ceiling glass doors and step out onto your...
NEW LISTING!! Kapalua Ridge Villa #1722 with views that are simply spectacular!
With views that you thought were only made for dreams, this villa will surely take your breath away. Located in the world-class Kapalua Resort, the vistas this unit has to offer are truly jaw dropping. Your windows are filled with a panorama composed of the sparkling...
Molokai Shores Resort Condo
Set sail to Molokai and book an unforgettable stay at this Kaunakakai vacation rental. The 1-bedroom, 1-bathroom tropical condo, located in the Molokai Shores Resort community, boasts access to the year-round outdoor pool, shuffleboard, picnic areas, and 4 acres of...
Summer sale! Fairways at Mauna Lani: Deluxe Island Getaway
10% discount for bookings 7 nights or more.The deluxe 2 bedroom town home will delight you and the island of Hawaii will not disappoint. Golf course view, private patio, 2 coaster bikes, resort pool and on-site gym. Enjoy the beautiful walking/running trails and the...
Relaxing Hawaiian Suite for a Exiting Getaway in the Upcountry of Maui!
The Makani suite is named after the wonderful trade winds we receive here on Maui! Enjoy the breeze in the front lanai rocking chairs while sipping your cup of coffee. Though this is our economy suite it is spacious and has all the comforts and amenities. Designed in a...
"The Happy Seal" Oceanfront House, watch seals sunbath from our deck while BBQ
[A legal rental of minimum 30 days]This is the story of a little beach house doing its part in preserving a sanctuary on this stretch of sand for the endangered Hawaiian monk seals. For many years the beach in front of the house was known as the home of a famously...
Pure comfort in Paradise!
Location is everything with this property. Not only is the beach right across the street, you are also a short walking distance from restaurants and shops of every kind. This unit is away from the street completely remodeled from top to bottom in 2020 and on the second...
Wailea Beach Villas PH210 - 2 Bedroom Garden View Penthouse
Experience the beauty of Maui in the luxurious Penthouse 210 at Wailea Beach Villas, a stunning retreat featuring two bedrooms and two bathrooms designed with tropical island elegance. This vacation rental welcomes families with its spacious layout, offering stylish...
MODERN HAWAII ⛳️ Luxe Remodel, Closest 3BR Kapalua Golf Villa to Beach & 4th Tee!
Modern Luxury at Kapalua Golf Villas – Your Ultimate Maui RetreatWelcome to Modern Hawaii at Kapalua Golf Villas, a rare three-bedroom, three-bathroom retreat offering over 2,000 sq. ft. of beautifully remodeled living space. Nestled in the front row of the...
koolkondo 2597 Halalu Guest house
Welcome to your dream escape in Poipu Beach Estates! This beautifully upgraded one bedroom guest house is tucked away in a serene, palm-fringed setting that offers ultimate privacy and space to unwind in paradise.The Guest house features one king bed and one queen sofa...
Pili Mai Family Condo 5C, 3 Bedroom 3 Bath, Mountain View, Cool Lanai,
Pili Mai is the south shore's newest development and adjacent to Poipu's ocean view Kiahuna Champion Golf Course. Your dream vacation is waiting at this second story, 3 bedroom, 3 bath spacious condo. The lanai gives plenty of outdoor space to enjoy outdoor living for...
Aloha Waikiki Condo 2Beds, 2Baths, Free Parking.
Aloha, thanks for checking in our listing. A Newly remodeled penthouse 2 bedrooms and 2 full baths. There are 4 queen beds and 1 single beds, full kitchen with kitchenette. It's spacious 1,000 sq. ft. with 2 patio and 3 Air-Con. It’s on 17 top floor with beautiful...
Hale Nana Kohola – Puako Oceanfront Vacation Home
Hale Nana Kohola (Whale Watch House) Located in the heart of Puako, offers a tropical retreat that showcases the best of Hawaii and is perfect for a romantic getaway or a family vacation. Escape to the sunny Kohala Coast on the Island of Hawaii. Hawaii's perfect...
Maui's BEST AC Beachfront – Panoramic Ocean Views! No Cleaning/ Parking Fees
Free Parking | Free WiFi | No Resort FeesWelcome to your dream Maui getaway! Our stunning beachfront corner unit condo on Kahana Beach offers breathtaking panoramic ocean views with floor-to-ceiling windows and doors, filling your space with endless blue horizons. Relax...
ICC 41 Remodeled 3BD Kaanapali Cottage w Heated Pool
International Colony Club 41 Spacious and Beautifully Remodeled Kaanapali Cottage, Rare 3Bedroom, 2Bathroom, Walk to the Beach! FREE daily activities included with your stay value up to $570! Complimentary admission, every day of your stay*: Whale Watch (seasonal),...