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.
Removed Trees=stunning ocean sunsets,@Wailea Beaches, Green, and Foodie Kitchen!
To enjoy our GORGEOUS OCEAN VIEW, from our upscale, VERY GREEN, very sound proof, 2 Bedroom, 1 and 1/2 Bath Condo, just a 4 minute walk to the nicest Beach on Maui, Keawakapu. Just book it here! Take a nap or read a book looking out on lawn, woods, and ocean as the...
Kamaole Sands -Inner Court-Extra Large Lanai-Ocean & Garden Views
Aloha!Quick note: --We also own 2 other Maui Condos & Sunriver Oregon Vacation Properties, see below for VRBO #'sWe invite you to escape to our newest place in paradise. We now have something for everyone at Kamaole Sands. We also own a 1 Bdrm/2 Bath condo at Kamaole...
HOL 104 Poolside Condo at OceanFront Resort
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...
Prime ground-floor location with many extras
Papakea B102 is a 1-bedroom, 1-bathroom condo featuring amenities such as a washer/dryer, 1 window air-conditioning and more! The condo can accommodate up to 4 guests with a California King-size bed in the bedroom and a queen sleeper sofa in the living space. The...
Magnificant Condo in Paradise. New mini split air condioners. Unit A208
Welcome to the sunny side of Maui! Our 2 bedroom, 2 bath condo is exceptionally large, approximately 1050 sq. ft. with a terrific Kehei location. Restaurants, shops, and beaches are easily walked to within a matter of minutes. Haleakala Shores is a smaller condo complex...
Kaanapali Alii | 384
The phrase “modern elegance” comes to mind when describing platinum-rated Kaanapali Alii 384. An abundance of clean white walls, white tiled floors, and cream-colored furnishings partnered with dramatic dark wood accent pieces, cabinets, and doors set a minimalist...
Dreamy Puako Beach House on White Sand Beach with AC!
Absolutely stunning 3 bedroom/2 bath beach house. Hale Laʻi Laʻi ~ Home of tranquility and contentment. Recently remodeled to create a feeling of contemporary elegance and relaxation with total beach vibes. Everything has been upgraded with soft modern finishes...
A/C - Blue Ocean - Mountain & Waterfall Views
This air conditioned island gem is set atop the Jungle Valley. Sit back and take in the stunning Mountains, Waterfalls and partial Ocean Views. Take a stroll and sit on the nearby grassy bluff to watch migrating whales when in season. Experience the symphony of tropical...
Maui Resort Rentals: Honua Kai Konea 543 - Expansive 5th Floor 2BR w/ Fantastic Ocean Views
Konea 543 is a gorgeous oversized 1315 sq ft 2 bedroom OCEAN VIEW villa with 3 KING BEDS that affords а perfect opportunity for a GROUP OF 8 to gather and celebrate or just have a relaxing time! Its 5th-floor location offers beautiful ocean and pool views. This prime...
Spacious Home In Kahala That's Centrally Located w/AC, Pool, Lanai 5BR/4Bath
Upscale neighborhood of Kahala that is walking distance to Kahala Mall. It's about a One mile drive to the nearest beach, Kahala Hotel, Waialae Country club. 6-minute drive to the world famous Waikiki Beach, Diamond Head hiking, Rainbow's plate lunch, Leonard’s...
Private Country Cottage
Cottage is located on the back side of a one acre manicured property. It is private from the main house the landscaping keeps you from seeing the house when sitting on the back lanai where the BBQ and sitting area is located. There is one off the road parking stall for...
Princeville Queens Bath House - 100 Steps to Trailhead
Our house was designed to be the ultimate family vacation house. It has a 29' pool and exotic tropical hot tub with waterfall ! You'll love the fully opening sliding glass lanai doors, bringing the island style open feeling from the great room to the outdoor lanai -...
🏖️Spectacular Ocean Views | Beautiful Landscaping | Private | vrKCV
vrKCV - Puuwai Alii Place, Professionally Managed by Kona Coast VacationsPu'uwai Villa is on a landscaped half-acre on a private road with plenty of off-street parking.Private, very quiet, one of only six homes on the private road. A large open space forest borders the...
RARE SINGLE LEVEL 2 BEDROOM-SPECTACULAR OCEAN VIEWS-AC-METICULOUS CLEANING
Book with confidence, this beautiful over sized, 2 bedroom, 2 bathroom condo that has stunning ocean views. This condo is managed by PMI Maui, a local Real Estate Brokerage that specializes in vacation rentals. We are located within a mile of the resort and available...
5 Minutes to the Beach! Oahu Ocean View + Family retreat
☆ A luxury-style escape without the resort price ☆ Private 9-seat hot tub for relaxing soaks under the stars☆ Pool & Spa: Brand new Ocean-view community pool in a quiet, gated neighborhood☆ Outdoor Bar and grill in private backyard and 10-seat dining table for...
New Waikiki Boutique Condo 1.5 blocks to the sands of Waikiki Beach!
This boutique condo is just 1½ blocks to the pristine sands of Waikiki Beach! Newly renovated studio with a fully equipped kitchenette, and beautiful mountain/city views from the private lanai. The ideal location and beach themed decor make this vacation retreat one...
The best value for your vacation! Pool and BBQ!
Why stay in a small hotel room when you can have a 1600sft house just for you and your family! 4 Bedrooms can easily sleep 8 people, awesome entertainment area with BBQ, Pool, Outside furniture, parking for 3 cars, A/C in every room. 15 minutes to a surf beach or...
Paradise found! 3-bedroom home with large lanai two blocks from the ocean
Your Pāhoa adventure begins at this 3-bedroom house with air conditioned bedrooms and downstairs studio. With two bedrooms upstairs (king in primary bedroom with en suite bathroom and a guest room with a queen bed and separate bathroom) and a studio downstairs (king...
Ocean View Golf Paradise | KGV 24-T4 | Maui Luxury
*Absolutely Stunning Ocean and Sunset Views*Huge View Lanai With Loungers and Dining Seats*Updated and Well Maintained Large CondoExperience Maui luxury at its finest in ocean-view Kapalua Golf Villa 24T4, where panoramic Pacific vistas greet you from every room. This...
Great Location In Wakiki, Walking Distance To Beach, Shopping, Dining!
Experience island living in this beautifully furnished 2-bedroom, 2-bathroom condo with breathtaking ocean and city views from your private lanai. Located on the 23rd floor, this unit is fully furnished and thoughtfully equipped, you'll enjoy a complete kitchen with...
Kona Coast Original Beach Boys 9.5 acre Estate, Pool and Amazing Ocean Views
Kona recalls the Beach Boys playing their pop hits by the pool. The band left but the good vibrations linger. Situated on 9.5 gated acres, gated for with an amazing Hawaiian plantation-style home with separate sleeping quarters and a guest house. Pool hot tub, gas...
Beautiful, Modern, & Spacious: Updated Island Townhome Great for Large Groups
If you're looking for a place to unwind in style while you're on island, Puamana 6B has everything you'll need! This attractive, contemporary retreat features two spacious and comfortable bedrooms, each with their own private lanai, as well as a third double bed in the...
Ground-Floor Ocean View W/Lanai–Kaha Lani #105
Castle Kaha Lani Resort #105 on the ground floor: Set on the ground floor with ocean views, this one-bedroom/one-and-a-half-bathroom condo features bright and airy interiors with oversized windows. Calm earth tones, ornate finishes, and pops of tropical-colored patterns...
Oceanview Serenity Meets Modern Comfort: Discover Wailea Ekolu #402
Wailea Ekolu #402 – Your Serene Wailea EscapeEscape to paradise at Wailea Ekolu #402, where stunning ocean views, serene surroundings, and the spirit of aloha combine to create the ultimate Maui getaway. Nestled above Wailea’s world-famous beaches and golf courses,...
Charming Home in Mountain View
Newly remodeled home on a two acre property will provide you a real taste of big island living. Peaceful and relaxing environment. Fresh mountain air. Magnificent native foliage. Comfortable cool climate.Explore the island by kayaking in Hilo Bay. Complimentary rental...
koolkondo Ohana House with Pool by the beach
Welcome to koolkondo where you will experience luxury vacation rentals at its finest. Our stylish boutique hotel style condos and homes have it all. You will absolutely enjoy your home away from home with VIP concierge style services in modern island luxury!Aloha and...
STUNNING OCEANFRONT TOP FLOOR CONDO
Aloha and welcome to Kahana Reef #409. With an elevator and stairway right next to the private hallway that leads to our condo it makes it extremely accessible for all. Larger then most condos at the Reef it has 661 square feet. Bedroom is spacious with a Ca king size...
Ko'Olina, a Luxurious and Private House on the Golf Course and Across the Beach
We invite you to experience Paradise at the Ko Olina Resort on the Island of Oahu. This rare and beautifully appointed Executve home is located in a Gated Community right on the Golf Course! The Championship KoOlina Golf Course surrounds the property. A short ten minute...
Oceanfront Penthouse, As Close As You Can Stay To Ocean, Stunning Views, A/C!
Banyan Tree Penthouse Condo 402 is a spacious, ocean front condo with an ocean view that will leave you breathless. Located on the quiet 4th floor, penthouse level yet so close to the water that you can actually look down and see tropical fish like the yellow tang! Sea...
Kahala Beachfront Estate – Private Resort-Style Living
For discounted rates on Main house only, please inquire. 7 Night Minimum over any major holiday except Christmas. 10- 12 Night Minimum over the Christmas/New Years Holiday Season at $8,400 per night.Spacious beachfront estate is situated on lush tropical grounds,...
Custom cottage feels bright & airy yet cozy and private in this country setting.
Cottage Cottage feels open and airy with high open beam ceilings in the living room and kitchen. Lots of windows let the trade winds in. Chill upstairs on the catwalk in a comfy recliner or outside on one of the 2 decks or on the relaxing dbl hammock outside. Short Walk...
Aloha Condos, Kanaloa at Kona, Condo 3103, Oceanfront, AC
Kanaloa at Kona Condo 3103 is a wonderful place to stay in Hawaii. Located next to the ocean, it offers stunning views and is fully furnished with everything needed, including a well-equipped kitchen, beach gear, and amenities like pools. Guests praise its cleanliness,...
Hapuna Beach Residence B27 at Mauna Kea Resort
This marvelous, oceanfront, newly-constructed, second level studio offers floor-to-ceiling sliding window walls that create indoor/outdoor living space, a luxe chefs' kitchen outfitted with professional-grade Wolf, Sub-Zero and Miele appliances, wine storage and...
Oceanfront Serenity at Maʻalaea Banyans Unit 315
Step into your own oceanfront escape at Maʻalaea Banyans 315 — a beautifully maintained 1-bedroom, 1-bathroom vacation rental with stunning, unobstructed views of the Pacific Ocean. Wake up to the sound of gentle waves and enjoy morning coffee or sunset cocktails...
Emmalani Court 422 - Renovated Princeville Vacation Rental with Pool
Emmalani court is a small, quiet complex in Princeville, near the Princeville Resort. After visiting the 4 main islands in Hawaii, we decided on the North shore for it's lush setting and laid back vibe. There is truly no other place like it in the world. We have been...
Hale Terra 3br 2.5ba Beautiful Nihilani Condo, Central AC, Pool, Hot Tub
Escape to Hale Terra, a modern surf shack nestled in the heart of Princeville. This luxurious, beautifully furnished, 2-story Nihilani townhome offers a tranquil retreat just steps from the pool and BBQ area.Our 3-bedroom, 2.5-bathroom townhome features hardwood floors,...
Spectacular Oceanfront Corner Unit Condo at Kuhio Shores
Closest complex to the water in Poipu, this corner unit in Kuhio Shores is situated on the third floor. Repeat guests come year after year to enjoy our air conditioned oceanfront condo. Whether it's to be lulled to sleep by the sound of the waves, relaxing on the lanai...
Oceanview Remodeled Across from Kamaole 3 Beach
Hosted by VacaMauiWelcome to your perfect Hawaiian getaway at Haleakala Shores! This beautifully remodeled condo, located directly across the street from the pristine white sands of Kamaole Beach Park 3, offers an unbeatable location for swimming, snorkeling, and boogie...
Waipouli Beach D-303 2 Heavenly Cal King Beds We Pay Resort Fee's - Best Reviews
This unit is MOUNTAIN VIEW VIEW VIEW!Special* Book Now & We Pay Your Daily Resort Fee's!Covid-19 UPDATE: IF there is a mandatory quarantine in effect on the day of your arrival, I will refund you 100% if you request to cancel, and if the VRBO cancellation policy you see...
🏖️Close to Beaches & Restaurants | Spacious Townhome | Concierge Incl
vrKCV - Mauna Lani Village 606, Professionally Managed by Kona Coast VacationsWelcome to Your Slice of Paradise at Mauna Lani VillagesWhether you're planning a family vacation, a couples' retreat, or a relaxing trip with friends, this inviting 3-bedroom, 3.5-bath home...
Waikiki Shore 2 Bedroom Condo
Welcome to our 2 bedroom Waikiki Shore Condo. This exclusive Waikiki Shore Condominium is located directly on Waikiki Beach, and is the only privately owned condominium building on Waikiki Beach, and sharing this world famous beach frontage along with some of the finest...
Ocean View Sky Ala Moana Condo w/Amazing Amenities Near Restaurants & Shops
This property requires a minimum 30-day rental. Book with confidence—professionally managed by Ali'i Beach Rentals, an award-winning property management company.Welcome to The Sky Ala Moana, the newest pinnacle of luxury in Honolulu. This exquisite property,...
Poipu Luxury Farmhouse: NEW Estate with Access to Pool & Pickleball
Welcome to our Luxury Farmhouse, perfect for large groups or families. Just a half mile from the beach, this property features 5 bedrooms, 4 baths, 2 family rooms, and 1.5 kitchens. Enjoy open shared spaces, private lanais, well-equipped kitchens, spacious baths, A/C...
🤙 APRIL+May Request SPECIAL 🏝️ at the upgraded LIVE ALOHA SUITE
Receive a discount from the listed price by contacting me through VRBO! THE LIVE ALOHA SUITE is a tastefully designed condo by Stannard Architects, of an international design firm, Olson Sundberg. It is a reflection of the tropics, well appointed, fresh, clean and...
Calming Coastal Vistas
Summary:Renovated oceanfront 1 bedroom, 1 bath condo with fantastic ocean views. Located in the sunny and vibrant beach town of Kihei. Beach chairs, umbrellas, luxury beach towels and a cooler are all provided to enjoy your day at the beach! We strive to achieve a...
Special Low Rates-Boutique Ocean Front Living- Cold AC- 5 stars-Romantic
Escape to Paradise at Surf Hale – Luxury Maui Vacation Rental in Kahana. Partake in this stunning luxury oceanfront rental in Maui, perched just 10 feet from the water’s edge on the second floor. Freshly remodeled, this romantic getaway in Kahana offers breathtaking...
Privacy In Paradise - Top Rated Vacation Home in West Maui
Discover the best in hospitality: Your five-star retreat awaits!Kalapana is truly “Privacy in Paradise” as the home is surrounded by 1.5 acres of lush tropical gardens and fruit trees, in the beautiful neighborhood of Launiupoko, Lahaina. This luxury home is fully...
Beautiful Lae Nani - Oceanfront 2 bedroom 2 bath condo with AC
For your comfort, new split air conditioners have been installed in the living room/dining area and both bedrooms. This recently remodeled and updated resort style condo with majestic ocean views is located on the bay on the Coconut Coast of the island of Kauai and is...
Private Oceanfront Top Floor Condo - Kona Reef D34
NEW OWNERS! NEW UPDATES AND IMPROVEMENTS! Welcome to our private and comfortable ocean front condo in paradise - Kona Reef D-34. As soon as you arrive to our very private top floor ocean front condo located on the romantic coastline of the Island of Hawaii you will...
One of Our Best, Now Thru Summer- 6th NIGHT FREE, (Ask Dave How) ~ Platinum Maui Vacations
Welcome to Hale I Ke Kai - which translates in Hawaiian to 'Home Towards The Sea'.From the moment you enter, you will be mesmerized by the breathtaking ocean views from every room of villa 'Hale I Ke Kai'. This impressive villa stands out from the rest with its 180°...