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.
VACATION DATES: OCTOBER 18-25, 2025: 2BR/2BATH VILLA KAANAPALI
ENJOY AN OHANA HAWAII EXPERIENCE AT A VALUE PRICE. EXPERIENCE PERSONAL CUSTOMER SERVICE FROM AN OWNER OF THIS VILLA TIMESHARE.OFFERING OUR 2 BEDROOM / 2 BATHROOM UPPER FLOOR OCEANFRONT VILLA AT $600 DAILY RENTAL PRICE. GUARANTEED UPPER OCEANFRONT VILLA ON FLOORS 9-...
Downtown condo with pool, tennis, & mountain view - walk to beach
Waikiki Sunset 1605Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome to your newly renovated 1-bedroom, 1-bath condo at the Waikiki Sunset in Honolulu, HI. This apartment...
(4102/03) 2Br Ground Floor Hanalei Bay Resort, Ocean View, Pool, Tennis
Welcome to Hanalei Bay Resort unit 4102/4103. A ground floor unit with stunning views of Hanalei Bay and the surrounding Bali Hai Mountains. This beautiful unit has 2 bedrooms, one with a King size bed and large en-suite bathroom with a shower to rinse off after a day...
Banzai Surf Escape -w/ AC, Epic beach by the house!
Banzai Surf Escape has all of your basic needs so that you can best spend your time relaxing near the ocean and enjoying all of the local spots. The open floor plan allows you to breath and relax during your stay. Enjoy air conditioning after a hot day at the beach and...
Pili Mai Family Fun Condo, AC, Game Room, 2 Bedroom, 2.5 Bath, Sleeps 6
FAMILY FUN at Pili Mai, 2br + Game room (bumper pool, poker table, classic video game console, board games, piano, masks and snorkels, beach chairs, croquet, and small yard for the kids to play) 2.5 bath, sleeps 6, no stairs, back yard lawn. Condo is located near the...
Spacious Lanai Retreat: Kapalua Maui's Golf Villa with Breathtaking Views 14T 1-2
This is a legally permitted vacation rental according to the County of Maui ordinances.Spacious Lanai Retreat: Kapalua Maui's Golf Villa with Breathtaking ViewsImmerse yourself in the epitome of luxury with our recently refurbished 1-bedroom, 2-bathroom condo, nestled...
Epic Forest View, A/C, Fruit Trees, Beach 5m drive
Experience this forest retreat complete with a cozy queen bed, AIR CONDITIONING, vaulted ceilings, convenient kitchenette, half bath, and an outdoor hot/cold shower. Relax on the expansive deck facing breathtaking panoramic views of the untouched jungle. Immerse...
Wavecrest Oceanfront Rental
TA-061-740-4416-01GE-061-740-4416-01This recently remodeled ground floor oceanfront condo with spectacular ocean views on the lush and undeveloped east end of the " friendly" island of Molokai , is one of the most picturesque locations. Enjoy the amenities of the...
Epic Maui Adventure On a Shoestring Budget
Come Explore Maui in this powerful, automatic, 2017 Jeep Wrangler Unlimited. Kenji comes fully stocked with all the camping gear you need, at no extra cost. We even throw in a pop up tent for sleeping outside. Heads up: All drivers must:* Pay our $15 per day insurance...
Artevilla at Pauoa Beach - Luxury Estate with Private Pool & Club Perks
Welcome to Artevilla at Pauoa Beach, the best of modern living in a classic Hawaiian setting.Nestled adjacent to the renowned Fairmont Orchid 5-star Hotel and Mauna Lani, Auberge Resorts Collection, Artevilla is a lavish two-story villa offering unrivaled luxury....
Luxury Oceanfront Air-Conditioned 2 bedroom Condo Rental- 35 Feet from the Water
Open the door to our beautiful second home in Kauai and know you are in paradise. There is nothing between you and the vast blue ocean, just 35 feet away, which is framed by a wall to wall expanse of floor to ceiling windows. The soothing sounds of the ocean fill the...
REMODELED 2 BED/2 BATH CONDO ACROSS FROM KAM3 BEACH W/ OCEAN VIEW
Maui Parkshore at 2653 South Kihei Road is located in the heart of South Kihei just a step away from some of the best beaches Maui has to offer. Its convenient location is also a walking distance to many restaurants, cafes, tourist gift shops, and a health food store!...
Luxury Kolea Golf & Hilton Pass, Partial Ocean View, 2 Min to Beach & Clubhouse
Villa Makai at Kolea, an ocean and beach front resort located on Anaeho’omalu Bay (A Bay), is the perfect spot for a refreshing get-away or the ultimate location for your home-away-from-home! Just a few minutes' walk from A-Bay, the only white sandy beach at Waikoloa...
Great View, 3 Pools, A/C, Walking Distance to Beaches! Kapalua Bay Villa #38G3
* NEW PROMO: Stay 5 or more nights from August 1st - October 25, get 1 FREE! Welcome to Kapalua Bay Villa 38G3, a beautifully renovated 1-bedroom, 1.5-bathroom ocean-view villa that offers the perfect blend of refined luxury and island serenity. Located in the...
Across From Kamaole 2 Beach, This Concrete Resort Is Maintained Well
Very important, Kihei Kai Nani is HOTEL ZONED, and not affected by ongoing Maui Transient accommodation issues, ours is a one-bedroom condo, on the top corner (2nd floor) of building #3, which is the second floor of a concrete building. The unit has a full kitchen and...
Welcome to Luana Garden Villas 3B & 3D
Crafted for multi-family vacations or larger gatherings, this listing offers two distinct Villas at the illustrious Luana Garden Villas — nestled on the captivating Kaanapali Beach on Maui’s western coast. Together, the upper and garden level villas are a haven of...
Villa Hui Hou: Luxe O'ahu Villa Private Oasis! Gourmet Kitchen & Media Room
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.Discover the allure of Kailua at Villa Hui Hou...
KHV 17 Spacious 2BD West Maui Condo with Ocean Views and Spectacular Sunsets
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...
Ko Olina Beach Villas 410: 4th Floor Ocean Front, Gourmet Kitchen, Private Lanai
Step into the world of luxury at Ko Olina Beach Villas B410 by Gather. Located on the fourth floor, this two-bedroom, two-bathroom oceanfront villa offers breathtaking panoramic views and elegant finishes. Perfect for up to four guests, it’s the ideal Hawaiian retreat...
Kona Coffee Mountain Getaway, in Holualoa
Completely renovated 2nd story home. Everything is brand new! New beds, new appliances, new cabinets and flooring! The house is 2 bedroom, 1 bath with shower and tub. Both bedrooms have a Cal king size bed. Living room with dining area, WiFi and TV, a full kitchen and...
AMAZING OCEAN VIEW Popular White Sands Village Steps To The Beach!!!
Hale Lihi LaniOcean View Vacation Rental at White Sands Village. We are located 4 miles south of charming Kailua-Kona Village and directly across from Kona's spectacular Magic Sands Beach. You will enjoy beautiful ocean views and dreamy sunsets from our large covered...
Kaanapali Royal B201: Your Dream Hawaiian Retreat
🌴 Escape to Paradise: Your Dream Vacation Awaits at Kaanapali Royal B201 🌺Imagine waking up in the heart of Kaanapali (Kāʻanapali), where the gentle sounds of swaying palm trees (nā niu) and the scent of tropical flowers (nā pua) welcome...
🏖️Concierge Included| No Stairs | Ocean View | vrKCV
vrKCV - Country Club Villas 230, Professionally Managed by Kona Coast VacationsDiscover the essence of island living at Unit 230 of the Country Club Villas in Kona, Hawaii. This charming 2-bedroom, 2-bathroom retreat offers an idyllic getaway in the desirable Keauhou...
MOST STUNNING Oceanfront Views, A/c, Washer/Dryer, Kitchen, Elevator, Beach 0.5m
2 Bedrooms, 2 Baths, Sleeps 6THIS CONDO HAS THE MOST STUNNING OCEAN & COVE VIEWS, BARRING NONE!!! THE WAVES CRASH RIGHT IN FRONT OF THE PATIO INTO THE MAGNIFICENT COVE BELOW. The occasional spray is the cherry on the top. The unit is fully air-conditioned.The living and...
Maui Resort Rentals: Honua Kai Hokulani 246 - 2BR w/ Partial Ocean AND Lush West Maui Mountain Views!
Hokulani 246 is an opulent two bedroom partial ocean view suite offering views of the Pacific Ocean and the awe-inspiring West Maui Mountains. As the second two bedroom back from the front you will find that this suite is well situated to enjoy what Maui is known for,...
Luxe Tropical Retreat w/ Private Pool, Spa, AC, Golf Cart Included
This newly constructed split-level home features an open floor plan, only the finest finishes, and its own pool and jacuzzi, along with access to the KaMilo pools, fitness center, and other recreational facilities. Luxuriously appointed, it creates a peaceful atmosphere...
3BR/3BA Penthouse: Central A/C! Short Walk 2Beach!
Welcome to BlueTideVillas! This is a VERY spacious (1650+ square feet), top floor (2nd & 3rd), corner Penthouse, 3BR/3BA with two private lanai's to sit on and enjoy your favorite tropical drink. This is one of the most demanded units in all of Poipu due to its central...
Puako Oceanfront Paradise
Enjoy your personal piece of paradise while staying at this private oceanfront oasis in Puako. Relax in the hammock on a lush yard while listening to the waves. Enjoy prime snorkeling or diving just steps away from the yard. Cool off or exercise in the lap pool. Unwind...
Poipu Crater 20 - A/C, Close to Beaches, Shopping, Golf and Restaurants
POIPU CRATER 20 AT KOLOA KAI VACATION RENTALSA Unique Hawaiian Retreat Inside a Tropical CraterWelcome to Poipu Crater 20, a charming and secluded two-bedroom condo nestled within a dormant volcanic crater. Surrounded by lush tropical gardens and vibrant birdlife, this...
New Aloha Ilikai 1Free Parking<br>(1777 Ala Moana BLVD)
ALOHA! Fully Renovated in June of 2025 / 1 free parking(There is a top-quality water purifier inside the unit, so there is no need to buy bottled water.)Perfect for couples, families, solo travelers, or business stayWe offer the ultimate Waikiki experience, combining...
Modern Oceanfront Condo with Stunning Views, Perfect for Any Getaway #705
Spectacular Maui condo! This bright and beautifully, modern condo is perfect for honeymooning couples, anniversary stays, family getaways, and those just looking to escape to their own tropical retreat. Mana Kai Resort is a favorite oceanfront community among travelers...
Renovated Steps to the Beach Cottage in Ewa Beach Serene Home w/Full Kitchen
This property requires a minimum 30-day rental. Book with confidence—professionally managed by Ali'i Beach Rentals, an award-winning property management company.Ewa Beach House is located at 91-293 Ewa Beach Road.A Hawaiian beach house away from home ensures...
Secluded Ocean View Sleeps 14 EASTER PRICING Book 10 nights for the price of 7
Looking for the perfect tropical retreat? MAUI TURTLE COVE is your ideal vacation home! Enjoy Maui in a beautiful 5 bedroom home with mature tropical landscaping and beautiful ocean views, including breathtaking Molokai Island! Just a short 3-minute walk down a private...
Papala Place at Kahakai Estates by Gather: Luxe Poolside Oasis
This private four-bedroom retreat within the gated Kahakai Estates blends elegance, space, and island charm. With partial ocean views, lush gardens, and a resort-style pool area, Papala Place offers a serene escape just minutes from Kailua Kona’s beaches, shopping,...
Ocean Front Studio , perfect for a romantic getaway ....
Unit 321 is in the Konea Tower of Honua Kai.The Ocean View Suite on the 3rd floor overlooks the Adult ( quiet) pool and steps away from Dukes Restaurant and Bar You have full access to the resort and your key gives you access to the fully equipped Gym that is also in...
Luxurious Poipu condo - Walk to multiple beaches - Central AC - Wifi - Pools
Welcome to your slice of paradise in Poipu!Nestled in the prestigious Regency @ Poipu Kai Resort, our newly furnished, air-conditioned, 5-bedroom luxury condo offers an oasis of comfort and elegance on the beautiful island of Kauai. Perched on the 2nd and 3rd floors,...
PARADISE RV .You won't forget your time in this romantic, memorable place.
Experience the magic of Maui on your terms! Our camper vans provide you the freedom to explore hidden beaches, wake up to sunrise on Haleakala. Tailor your Hawaiian adventure. Enjoy Maui beautiful!!!!
Available and legal for stays less than 30 days.
Hawaii Sheffield House has been a legal bed and breakfast for over 35 years. We are available and legal for stays of less than 30 days. We provide a unique neighborhood stay in Kailua Hawaii that is just down the street from Kailua Beach.The Hawaii Sheffield House...
Gorgeous Estate on the Slopes of Diamond Head, 5 minute walk to great beach
Treat yourself to ultimate island luxury in this architecturally designed $5.5M home on 15,000 sq ft lot in one of the most desired locations on Oahu's south shore. Nestled on the slopes of Diamond Head just outside of Waikiki, this exquisite estate is a 5-MINUTE WALK...
Paradise Found! Top Floor, Beachfront, Oceanfront, Ocean View
Welcome to Paradise Found! Memories are made here!Come, relax, unwind, and enjoy the unforgettable breathtaking, panoramic ocean views from EVERY room in our beautiful top floor direct oceanfront, beachfront Kealia Resort Condominium nestled RIGHT ON Sugar Beach, just...
Beachfront 6 Bedrooms with Pool
Legal Vacation Rental: Permit Number STKM2020/0002HOLIDAY SEASON: There is a 7 night minimum during the period Dec 18-27. There is a 10 night minimum during the period Dec 27-Jan 10.Chill Out with friends or family in this spacious two-story Maui beach house which...
Stunning Two bedroon Corner Oceanview condo in Kihei
D301 is a uniquely located corner unit 2 bedroom, 2 bath full ocean view condo with AC. This condo is on the third floor so you are walking up stairs.Watch surfers, windsurfers, and kite boarders as well as Humpback Whales during the Whale season. Wake up to stunning...
Partial Ocean View 2 Double Beds at Outrigger Kona Resort and Spa
Your adventure to the Kona Coast starts at this oceanfront Big Island property, just steps away from the sun, sand, and surf. Guests will enjoy spectacular dining options, including a waterfront restaurant and poolside bar. The on-site spa and fitness center offer a...
Maui Resort Rentals: Polo Beach Club 608 – Luxurious 6th-Floor Oceanfront 2BR w/ Stunning Ocean Views!
We are proud to present this luxurious 2BR/2BA oceanfront residence at Polo Beach Club–newly launched on 10/25/24 to start taking reservations for check-ins on 1/6/25!Boasting a stunning Wailea oceanfront location and a lavish interior, this 2BR/2BA residence delivers...
Luxury 800 ft" 1 bedroom Suite, Full Large Kitchen, King size bed, Free Laundry
Built in 2022!This large luxury1-bedroom suite, the main part of the 4 beds, 3 baths single family house with its own private entrance, is located on a one-acre land harboring the most unique feature of Hawaii Paradise Park in Keaau and offers a real retreat from the...
Hanalei Bay Villas #36 - Ocean and Mountain View Condo
Hanalei Bay Villas #36 is a spacious three bedroom, two and a half bath, two story stand-alone condominium. Beach access is available past the newly renovated 1 Hotel Hanalei Bay next door. Views include the Hanalei Mountains and the open ocean. You enter the villa on...
Oceanfront Sugar Beach 525 Tropical Condo, on the Beach,
SOUTHWEST SUNSETS-Sitting on the lanai, you are facing beautiful southwest sunsets, view is the website pictureWHALES January through April breaching in your view, all the comforts of home in a warm, tropical location with our building 20 feet from the ocean. BEACH is...
Beachfront Platinum Condo, updated. Gorgeous Ocean & Crater Views. Makena Surf.
Building B is the premier beachfront building at Makena Surf, set among lush tropical gardens. From our condo (B202), gaze endlessly at the ocean, watch the whales breach (seasonal), experience magical sun sets, step onto the beach to swim or snorkel with the turtles or...
ILIKAI NEWLY RENOVATED OCEAN VIEW ONE FREE PARKING
Newly renovated stunning condo unit at the Ilikai hotel is fully equipped with everything you will need for the perfect stay. All new appliances, furniture, flat screen TV's, leather pull out sofa, modern design, bidets, AC, Xbox, Wifi and more. 2 bedrooms, 2 full...
Kaanapali Alii | 246
Kaanapali Alii 246 was designed for entertaining! As a corner unit, most of the living room and dining room are highlighted with wrap-around windows which offer constant views of the beautiful Maui landscape. The open floor plan seamlessly combines the kitchen, dining...