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.
Panoramic View of Black rock and beach
One bedroom, 2 bath beach front condo at The Whaler on Kaanapali Beach in Maui, sleeps 5. Beautifully appointed, on the 9th floor overlooking the Pacific Ocean this well maintained Maui beach condo features breathtaking ocean views, and every convenience in your...
Permitted Hawaiian Princess condo on beach with sea turtles and amazing sunsets
This mid-floor beachfront condo at the Hawaiian Princess comes complete with a spectacular sunset ocean view from the lanai. The condo has been remodeled with the best of everything. Amenities include a deluxe fully equipped kitchen with top-of-the-line stainless steel...
Oceanfront on Kauai starting at $140/night!
Our 1 bedroom oceanfront Kauai condo, unit 111, has been with VRBO for over 10 years and has been booked almost everyday with over 100, 5-star reviews. You will find yourself right on the ocean and far from the highway! Sit and relax on your private lanai while watching...
AIRY AND SPACIOUS STUDIO ON GROUND FLOOR
The Blue Room is a “hotel style” studio with a private bathroom and covered lanai. Included are a comfy queen bed, wireless, smart t.v., coffee maker and mini fridge. There are no cooking or laundry facilities. Close to restaurants, shops, resorts and beaches....
Kalanikai 306: Cozy Oceanview Unit w/ AC & Shared Pool in the heart of Kona Town
Stay in the heart of Kona town at Kalanikai 306, a recently remodeled 1-bedroom, 1-bath condo that blends cool comfort with a walk-everywhere location. From your top-floor lanai, enjoy tranquil views of the pool framed by palms, with the Pacific glimmering beyond. With...
Oceanview, private pool, 5 acres of avocados! Gorgeous coffee district jewel!
Pu'u Mahana Plantation is the perfect destination for vacations and celebrations. Our hosted property lies in the heart of the coffee district, a secluded tropical estate offering guests a tranquil setting, 7 acres of manicured avocado and citrus trees, and lush borders...
Hawaii Life Rental Presents Kihei Holiday 113
Aloha and welcome to Kihei Holiday 113, one of Maui’s most sought after locations for an Island getaway. This perfectly located unit is directly across the street from one of the most beautiful beaches in Kihei. Walk two minutes across the street and watch the...
Deluxe Two Bedroom Partial Ocean View Luana Kai Resort B307
Unit B307 with AC is a deluxe, two bedroom two bathroom. It has a partial ocean view and courtyard view with tiki torches at night. B307 has a full wall mirror in the living room. A mix of carpet and tile graces the floors. The furnishings are rattan and wood. The...
Waipuna Hale: Oceanfront Cottage w/Panoramic Views, Yard, & Private Beach Access
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 Waipuna Cottage, a charming...
Kona Alii 707 Stunning Top Floor Penthouse w/ Roof Top Deck, AC, & Elevators
Beautifully remodeled spacious 1 bedroom, 2 bath that includes AC in the living room, modernized kitchen, large lanai, and 7th story viewing sundeck where you can bask in the Hawaii sunshine or under the shade of the outdoor umbrella, enjoy sunsets, & stargaze at night!...
Plantation Hale Suites K5, King Bed, AC, Wifi, Near Shops and Beaches
No Resort Fees! Plantation Hale Suites Unit K5. Kauai Vacation Rental in the heart of Kapaa Town. The perfect Kauai vacation rental for the budget minded traveler. All vacation rental units have spacious bedrooms, are non-smoking, air conditioned, and fully furnished....
4 br Luxury Home in Kukuiula w Pool
Spectacular golf course views are just some of the highlights of the Pa'ina Makai vacation rental in the luxury Poipu community of Kukuiula. Pa'ina, meaning “to gather” in the Hawaiian language, is the perfect name for this home, which has many open living areas for...
Oceanfront condo with ocean views, balcony, pool
Nohonani 301Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Live the true meaning of "island life" at this gorgeous oceanfront condo. Boasting expansive water and mountain views from...
Mesmerizing oceanfront condo with expansive views
Valley Isle 1109 is a 1-bedroom, 1-bathroom condo on the 11th floor featuring amenities such as panoramic ocean views, a private washer/dryer, and 1 ceiling fan. This condo does not have air conditioning. Valley Isle 1109 can accommodate up to 4 guests with a queen-size...
Ideal Makai Golf Course location, 2 primary suites plus loft, ocean view & AC
Hale On'tarioOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'High on a cliff in Princeville, a prime neighborhood in the heart of Kauai’s North Shore, Hale On'tariō is perfectly...
Private, quiet, ocean view home. 5 minutes from the beach!
Tiny home with ocean view and loaded with character and amenities! Quiet, serene, high ceilings, AC and more! 5 minutes from the beach, and gorgeous 2nd floor lanai (patio) overlooking the neighborhood.
GC 163 Spacious Wailea 2BD w AC Pool Close to Beach
FREE daily activities included with your stay value up to $956! Complimentary admission, every day of your stay*: Lu’au, Golf, Whale Watching (seasonal), Sunset Dinner Cruise, Molokini Snorkel Trip, Alpaca Farm Tour, Pineapple Farm Tour, and Tea Farm Tour. (S3)*One...
Maui Resort Rentals: Honua Kai Konea 345 - Large 2BR w/ Great Interior Courtyard Location
Konea 345 is a luxurious two-bedroom suite offering lush interior courtyard views as well as partial views of the ocean through the palm canopy. Guests will enjoy its fantastic location located in the closest two-bedroom column to the ocean in the desirable south facing...
Sugar Beach Resort #305
Beach Front Sugar Beach Resort. 3rd Floor, Ocean View Unit. Beautifully updated unit with sweeping ocean views. Enjoy all of the amenities in a clean, well-kept property. The entire complex sits ocean front, there are no roads to cross to get you onto the beach! 305 is...
Hibiscus Beach Cottage, Steps to Beach, Beautiful Mountain Views, TVNC#5067
"Hibiscus Hula Beach Cottage". Kauai Vacation Rental, Anahola, Kaua`i, Hawaii. TAT ID#: TA-092-402-4832-01, TVNC#: 5067. On-island manager, Garden Island Properties LLC.Step back into the 1950's and re-visit old Hawaii with this Anahola vacation rental beach cottage...
Beautiful ground floor unit at Kiahuna plantation with A/C.
Aloha and welcome to paradise at Kiahuna Plantation Unit 86, a stunningly remodeled one-bedroom, one-bath condo on Kauai’s sunny south shore in Poipu Beach. Nestled in the northeastern corner of this 35-acre resort, this ground-floor retreat boasts zero-step...
Upgraded Top-Floor Condo - Gorgeous Ocean Views!
E301 is the ultimate getaway for any couple with a spacious 1-bedroom and 2-full bathrooms in the exclusive Mauna Lani Terrace. Overlooking the Hawaiian fishponds, nothing obstructs your beautiful ocean and sunset views from the large covered lanai. The entire condo has...
Maui Dream Getaway! Breathtaking 180°Ocean&Mtn Views, 5⭐️Location,walk everywhere
Introducing "The Hokulani" - A Captivating Ocean View Penthouse at Papakea Resort in north Kaanapali.Experience the ultimate Maui getaway at this fourth-story penthouse nestled in the breathtaking Papakea Resort. With its unrivaled ocean views, spacious two-bedroom,...
Maui Resort Rentals: Honua Kai Konea 824 - Spacious 8th Floor 1BR w/ Partial Ocean and West Maui Mountain Views!
Konea 824 is a luxurious 8th-floor one-bedroom suite that offers partial ocean views along with views of The West Maui Mountains and Maui's neighbor island Molokai. The 824 experience is enhanced with one of the largest one-bedroom floor plans at the resort. To fully...
>> MauiPenthouses 4 Bd 4 Ba Ocean/Beach Front Spectacular MILLION Dollar Views<<
The Ultimate Maui Vacation Rental. Spectacular Ocean / Beach Front Maui Penthouses with Four Bedrooms & Four Bathrooms. Now Air Conditioning! We now have Daikin AC systems in each Bedroom, and Living room.These are two incredible side by side Maui Penthouses (the...
Luxury 3BDRM w/4beds + 2Bath + Partial Ocean View + Parking, 2min from the Beach
Legal vacation rental at a fabulous location!2 bedroom 2 bath home located across from ‘Alohilani Resort, one block from the Waikiki Strip (Kalakaua Ave) and the beach! Located in the heart of Waikiki, yet tucked away on a quiet and quaint street. There are endless...
n180 Degree Oceanfront Condo with Amazing Sunsets Night after Night
Our condo is literally 50 yards from the calming waves of the Pacific Ocean! 180 degree oceanfront views from your second floor lanai. Beautiful front lawn with pool and swaying palm trees stretching in front of a 58 unit, 3 story condo building. Comfortably furnished,...
Oceanfront Studio · Oceanfront Studio. See whales, turtles & dolphins!
Summary:Welcome to this private air conditioned Oceanfront Studio located between Hilo, Hawaii Volcanoes National Park, and black sand beaches! Just 35 minutes from Hilo international Airport, Rainbow Falls, and more! This is an affordable way for singles or couples to...
HAWAII Hilo Town~Private GATED Botanical GARDEN COTTAGE w Koi Pond
The Paradise Cottage at Anthurium Hale located in Hilo Town is an upscale, very private, free-standing cottage, "tiny house" with mountain and garden views, exclusive gated garden entry overlooking your own koi pond.Enjoy an intimate floral enhanced setting that...
Ma'alaea Surf Unit C1 Beachfront Condo, 2BR Ground Floor, AC, Wifi, Kitchen
Ma'alaea Surf, Unit C1 is deluxe in every sense. C1 is a conveniently located ground floor unit, just steps from the small pool. This unit is splendidly furnished. It features, air conditioning, complimentary Wifi, TV, fully furnished kitchen, complimentary parking,...
Kahana Village #42 Beach Front Luxury
Aloha, as quoted from Maui Revealed: The Ultimate Guide Book, "the ocean view building with units 37 - 42 would probably be classified as beachfront at most resorts." Enjoy the large comfortable lanai that looks over the ocean with beautiful view of Molokai. This...
Oceanfront Kealakekua Bay Retreat w/ Breathtaking Views from Every Room
Manini Beach Breath TakerOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Located in Kealakekua Bay, a protected marine sanctuary and an ideal spot for snorkeling, diving, and...
Kamaole Sands Building 10 Best Sunsets on the Island!
If you are looking for a low pressure vacation. This is the place. Right across from Kamaole Beach III the nicest family beach on the island.It's all about location. Building 10 is the closest to the beach and has the best views. 1 Bedroom-Queen Bed-brand new mattress....
Lae Nani 215. A Convenient Location, Beautifully Decorated Ground Floor Air Conditioned Condo.
Tropical gardens take you to our great pool and then to the beach. Brand new split system AC!! Parking next to your condo, no stairs to climb. Physically challenged persons will love the location. Two full beds in this one bedroom condo. One in the private bedroom and...
Luxurious Oceanfront Penthouse Condo Air Conditioned. Sleeps 4
Steps away from Kona Magic Sands BeachComfort- No hot humid nights- New modern Air conditioning from the roof top, controls one in the kitchen and one in the bedroom. It is open design ,the bedroom is not totally separate from the kitchenThis luxurious, absolute...
Coconut Plantation in Ko Olina. Special Pricing April through May 2024!!
Experience Ko Olina by staying in this resort style townhome, on the South-West coast of Oahu. The translation of Ko Olina is, “Place of Joy,” and was considered a quiet retreat for the ancient Ali’i, or Hawaiian royalty. Eventually the land was bought and the...
Kona Plaza#218 2nd Floor Unit in Heart Of Kona Town: AC & Elevators!
Experience the best of Kailua-Kona from the comfort of Kona Plaza #218! This beautifully remodeled gem is in the heart of Kona Town, offering a central location with immediate walking access to restaurants, the ocean, pristine beaches, boutique shopping, and local...
Oceanfront 3rd Floor Unit at Maalaea Kai Complex
Enjoy the beautiful seascapes, surrounding islands and lovely Hawaiian skies above meticulous, palm-lined grounds. Winter whale season from approx end of Nov to mid Apr. Catch the occasional view of resident turtles from the lanai. The peace within may entice you to...
Ocean View-Top Floor-A/C in All Rooms-Pacific Shores
We want you and your family to enjoy our two master bedroom, two full bathroom, completely remodeled, fully air-conditioned, top floor condo with beautiful diagonally placed tile throughout...No condo above us or to one side which means quiet time is REALLY quiet...
Plantation Hale Suites F7, Ground Floor, AC, Walk to Beach
Plantation Hale Suite F7 located in Kapa`a, Kaua'i, Hawaii on the Royal Coconut Coast. Walk to the beach, shops, restaurants, grocery stores, and more! Unit F7 is a relaxing location to view morning sunrises. Accommodates up to 4 guests, including children and...
Maui Resort Rentals: Honua Kai Hokulani 637 - Newly Upgraded 6th Floor Studio w/ Full Ocean Views!
This spacious ocean-view studio provides awe-inspiring views of the Pacific Ocean and Maui's neighbor island Lanai from its prime 6th-floor vantage point nestled in the Hokulani interior courtyard.Relax and reconnect in the ample living space fully appointed for your...
2nd-floor condo with amazing ocean views, private lanai, & updated interior
Hale Li'ili'i at Keawakapu #201Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Beautiful ocean views and sunset vistas abound at this private piece of Hawaiian paradise. Along with...
New Discounts thru 8/31: 2 bed, 2 bath, A/C, ocean view, secluded beach, pool
Come vacation at Kahana Sunset, a quiet, lushly landscaped, beautiful resort on secluded Keone Nui Bay. Swim from our beach, snorkel with turtles, enjoy spectacular sunsets, barbecue on our outdoor built-in gas grills—all without having to leave the complex! We are...
Islander on the Beach 246 Stunning Oceanfront!
Beautiful Direct Oceanfront Studio Condo - Steps to the Pool and Sandy Beach! Islander on the Beach Oceanfront 246! NEW Air Conditioner! No resort fee!Stunning Oceanfront Paradise! This Stunning Oceanfront Studio Condo at the Islander is located on the second floor....
Ground-Floor Gem Near the Beach with Lanai, WiFi, AC & On-Site Pool/Hot Tub
Pili Mai 2MOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Lush and manicured grounds, swaying palms, and views of the Kiahuna Golf Course and the neighboring mountains await at Pili...
Romance & Luxury in Paradise ~ Newly Appointed
ELEGANT Inside and TROPICAL Outside... Newly Renovated & Spectacular...! You have discovered one of the FINEST and Most BEAUTIFUL Condos in Princeville. Relax and Enjoy this HIGH END & Elegantly Appointed 2 Bedroom & 2 Bathroom Condo. This Ground Level ~ End Unit condo...
Ocean-view condo with balcony, AC, washer/dryer & pool - walk to the beach
Prince Kuhio 319Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Enjoy a relaxing Hawaiian escape at the Prince Kuhio condos of Kauai. Named in honor of the revered statesman and...
Waikoloa Beach Villas J32 - Luxury Penthouse Villa, Gold Golf Club Membership
This brand new upscale luxury condo is located in the privately gated new Waikoloa Beach Villas Complex, close to the activity center with two pools, fitness workout room and spa areas. Unit includes discounted GOLD GOLF KINGS' CLUB MEMBERSHIP - green fees at Waikoloa...
Oceanview 2 + 2 Fabulous Condo! Best Value Walk to Everything
The Shores of Maui overlooks the crystal clear Pacific Ocean on Maui's sunniest shore. This condo is the only one that has two private lanais! It is a one block walk to beautiful Charley Young Beach, one of Maui's finest swim beaches and directly across the street from...
Ground Floor Haven on a Lush Oceanfront Property - Wailea Elua 307 Awaits!
Wailea Elua #307 – Ground Floor Ocean View Comfort with Tropical EleganceWelcome to Wailea Elua #307, a newly remodeled ground-floor condo located in the oceanfront section of one of Wailea’s most exclusive communities. With expansive ocean and garden views, upscale...