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.
Maui Kamaole Kihei Resort I Beaches, Pools, Tennis
Prime South Kihei location across the road from Kamaole Beach lll and a 15 minute walk or 5 minute drive to Keawakapu Beach. Set on a 23 acres, Maui Kamaole is a lush, tropical resort with two swimming pools + spas, and two tennis courts.J201 is a large, upgraded condo...
Ma'alaea Surf Unit E5-2BD Beachfront Condo, AC, Wi-Fi, Pool, TV, Kitchen
Ma'alaea Surf, Unit E5, the most glorious and romantic sunset views at is why the architect who designed Ma'alaea Surf chose this unit for his home. Steps away from the wonderful walking beach and pool. This fully equipped unit features flat screen tv, cable, Wi-Fi,...
Oceanfront Resort steps to pool/beach via your lanai, 4 Beautiful Pools
Our unit is a privately owned hotel room located in the Outrigger Kauai Beach Resort and Spa.Beautiful first floor unit with excellent views of the resort and pools. Comfortable king bed with chaise lounge. Walk right out your lanai and you will be at the pools and...
Gorgeous Diamond Head Penthouse Studio Stunning views, Private Balcony.
Legally permitted vacation rental - 2947 Kalakaua Ave, Penthouse 5Stunning style with incredible Ocean & Diamond Head views.The care and attention to detail our owners put in, bringing their pride and joy on Hawaii's Gold Coast to fruition shows in every corner of this...
Tropical-view escape with pools, hot tub, tennis, AC, W/D - beaches await
Maui Kamaole D209Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Luxury and privacy meet at this Kihei Condo, located in the condo resort known as Maui Kamaole®, and just minutes...
Maui Banyan #Q-104: 2 Br in S Kihei, Walk to Beach, Shops and Dining
Located in building Q at the Maui Banyan, this two-bedroom condo has many upgrades and remodels. The Master bedroom has a queen bed and a full bathroom ensuite. The second bedroom has two full beds. There is a full bathroom just outside the second bedroom. The living...
Westside Magic Garden 3bed 2 bath house
Welcome to our charming vacation house located on the beautiful west side of Oahu, Hawaii! Our cozy rental is the perfect spot for travelers seeking a mix of adventure and relaxation, as we are conveniently located near some of the island's most stunning beaches, hiking...
Luxurious Makai Villa with Pool and Ocean Views
Aloha and welcome to our custom pool in Kailua-Kona! We have tastefully decorated this casual luxury home for your enjoyment. The large pool and lanai are set up for entertaining during sunny warm days or star-filled nights. This home has space for a large family or...
Sept.-Nov. Special $350 nt! BEAUTIFUL NEWLY RENOVATED OCEANFRONT
CONDO had A FULL RENOVATION,WITH BEAUTIFUL UPGRADES AND ALL NEW FURNISHINGS. The condo is a 1700 sq ft. ocean front, fifth floor, two bedroom, two bathroom condominium with AC that offers stunning views of Hawaiian sunsets, whales, sea turtles, and the islands of...
Hale `Ohana ~ Family Home - Kuilima Estates East
Welcome to Hale 'Ohana ~ The Family Home, your idyllic retreat nestled in the heart of Kahuku on Oahu's East Side. This cozy, thoughtfully designed 1-bedroom, 1-bathroom vacation rental offers a perfect blend of comfort and convenience, ideal for families or small...
Serene 5-acre tropical hideaway with lanai and circular wood-burning fireplace
Hale Hapu'uOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Nestled on five acres of rainforest, Hale Hapu'u is a serene two-bedroom, three-bath hideaway home in Volcano Village. This...
Charming 1br Top Floor Condo in Poipu, AC, Athletic Club, Beach Access
Welcome to Sunny Poipu Beach! This charming top floor Kiahuna Plantation condo was freshly remodeled with you in mind! Relax on your private lanai overlooking the garden while being steps to the sand. Surf spots, long walks and lifeguarded beach are at your fingertips....
Akahai at Poipu Beach By Parrish Kauai - elite home private pool & central AC!
Tucked back in one of Poipu Beach’s newest vacation rental neighborhoods, Akahai offers an exquisite and distinguished private luxury Kauai vacation rental unmatched by many. This exquisite three bedroom home offers a modern and open floorplan with designer touches,...
Ocean Front Pool, Private and Newly Renovated Top Corner Unit
Welcome to our condo in Hawaii, we like to give everyone a well deserved and affordable vacation. This is a very private and newly renovated, top floor corner unit centrally located in Kailua-Kona, Big Island Hawaii. 350 days of sunny weather in a year with some of the...
KBVC3 · Tropical 1 Bedroom with 2 Full Bath at Resort
Welcome to `Wahi Maluhia`! Peace to replenish your soul at this beautiful, simple Tropical Condo. Walk to the beach, enjoy the pools and spas, play some tennis and take advantage of grounds of adjacent Resort and picturesque oceanfront setting. Free parking affords you...
Waikoloa Beach Villas M2 - Ground Floor Villa, Fairway Views, Close to Beach!
Discover the spirit of Aloha! Our beautiful 2 bedroom 2 bath ground floor villa located in Waikoloa Beach villas in the Waikoloa Beach Resort. SPECIAL - 3 night minimum for this listing till December 31st.Tucked away next to one of the Aloha states largest and most...
Remodeled condo in the heart of Hilo with pool, lanai & walkable location
Waiakea Villas 4-124Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Find yourself in the heart of Hilo at this centrally located condo, newly and beautifully remodeled with every...
RK 104 BeachFront West Maui Studio w Pool and AC
Royal Kahana 104 Spacious Oceanfront Studio with Pool in West Maui 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...
Charming studio with killer ocean views, balcony & outdoor pool
Kapa'a Sands 11Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Ever dreamed of spending time in a cute little Hawaiian bungalow overlooking the ocean? This is it! Kapa’a Sands is...
DISCOUNTED RATES! 213 Beautiful oceanfront 1 bed/bath, 2nd floor condo
Gene and I live in Portland, Oregon. We first came to the Kulakane for our honeymoon in 1987 and that makes this our honeymoon home. We loved Hawaii and returned often, to The Kulakane and to other properties and islands. We kept coming back to the Kulakane as our...
Ocean-View Comfort at Kihei Garden Estates C204
Welcome to this top-floor loft-style condo offering breathtaking ocean (from the lanai) and garden views in the peaceful South Maui neighborhood. This beautifully upgraded two-bedroom, two-bath unit is perfect for anyone seeking a relaxing Maui getaway. Enjoy the charm...
Pali Ke Kua 244, Overlooks the Pacific Ocean.
This two-bedroom condo is located in the resort community of Princeville which overlooks the Pacific Ocean. The vaulted ceiling in the living area lends a spacious and airy feel to this nicely appointed condo. You can take in the gorgeous ocean views from the living...
Magnificent Waikiki Mountain Views! Free Parking, Wi-Fi, Pool & More!
Waikiki Sunset #2503 – 229 Paoakalani Ave.Enjoy the lush greenery of the Ko'olau Mountains and exquisite Hawaiian trade winds from your private lanai! This cozy rental features central A/C, a full kitchen, and free Wi-Fi—perfect for couples and small families!The...
Perfect Ocean View! Ilikai 1 Bedroom Harbor View, Minutes to the Beach!
1 Bedroom Yacht Harbor View on the 18th Floor! NEWS FLASH! This condo was completely gutted & renovated with brand new stainless steel appliances and furniture! Nothing was spared when completing this upgrade, it checks off all the marks for everything you'll need to...
Maui Resort Rentals: Honua Kai Hokulani 822 – Expansive 2BR Corner Suite w/ Gorgeous Mountain Views!
One of the absolute best values available at Honua Kai, Hokulani 822 is a luxurious 2BR/2BA suite offering panoramic views of the lush West Maui Mountains from its fantastic 8th-floor corner location. You can even catch glimpses of the tranquil blue Pacific in the...
Affordable Partial Ocean View South Maui Condo- Only 3 Minute Walk to the Beach
This affordable partial ocean view 1 bedroom and 1 bath condo is located in the beautiful South Maui town of Kihei. The condo is 12 miles from the airport. This tropical furnished condo with fresh paint is located on the 3rd floor in building 2 has a living room/dining...
TROPICAL MAUI!!! Visit and stay in Comfort and Style...1b/2b
Maui Banyan complex and condo are located just a short walk to the Kamaole Beach Park II. This is one of South Maui's best Life Guarded Beaches.The unit is fully furnished with all the comforts of your own personal home. Also includes amenities you will enjoy during...
Ilikai 1927 Ocean / Sunset / Marina Views 2 Double Beds, Sofa Bed
STUNNING OCEAN & SUNSET VIEWS! STEPS TO WAIKIKI BEACH. Sunset views. Walking distance to shopping mall, restaurants, shops, buses, rental cars, parks & Waikiki night life.The iconic Ilikai Suites are located at the gateway to Waikiki. Remodeled, Tastefully Furnished &...
Kihei Bay Surf 144 Tropical Hawaiian Style Condo, Beachy Theme New Split A/C
Kihei Bay Surf Studio #144 is a beautifully remodeled studio with a new split system A/C that can sleep up to 3 with a queen bed and a queen Tommy Bahama sofa bed. The unit is conveniently located on the lower level, and the lanai overlooks the pool area. This tiled...
If you're looking for your get-away spot, look no further.
***NEWS ALERT!*** This condo was gutted, fully renovated and tastefully decorated with brand new stainless steel appliances, furniture, roller shades, painting, the works!! This condo is located on the 6th floor of the Ilikai Hotel. Live in luxury with this spacious 500...
Puu Poa 204
Puu Poa 204Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Wake up in paradise when you stay at this spacious oceanfront condo. When you're not having a beach day, enjoy alfresco...
Honolulu Vacation Rental: Walk to Waikiki Beach!
Discover your Hawaiian paradise with a stay at this 1-bedroom, 1-bathroom vacation rental condo in beautiful Honolulu! Located only moments away from Waikiki Beach, this cozy retreat offers a private balcony with ocean views, access to tennis courts, and more! While...
Third-Floor Beach Condo w/ an Ocean View, Free WiFi, Washer/Dryer, & Shared Pool
Nohonani 306Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Get a taste of the tropics both inside and out at this darling, third-floor condo. Save a little money and prepare...
A Rainforest Eco-Lodge on the Hamakua Coast
Immerse yourself in the magic of the Kikala Waterfall Lodge, where cascading waterfalls and the enchanting Mauna Kea Cloudforest Bioreserve create a one-of-a-kind escape. Wake to the soothing sounds of waterfalls just steps from your door and explore lush botanical...
Amazing Pacific views from 2bd Top Floor condo
Paki Maui 405 is a 2-bedroom, 2-bathroom oceanfront condo located on the top/4th floor with wonderful unobstructed ocean views from your lanai and floor-to-ceiling double sliding glass doors, bringing natural light into the condo. The condo has a split AC conditioning...
KBR #208 - 1 Bedroom/1 Bath Serene Ocean Front unit on Stunning Sugar Beach!
This beachfront one-bedroom / one-bath condo in North Kihei, Maui offers a serene and beautiful retreat on Sugar Beach. The unit features quality finishes such as granite countertops, tile flooring, and lovely furniture. Central A/C, a spacious bedroom with a king bed,...
OCEANFRONT remodeled Napili Shores A106 - STEPS FROM BEACH!
Welcome to Napili Shores A106, a beautifully remodeled ground-floor studio offering uninterrupted ocean views, refined comfort, and immediate access to the pristine sands of Napili Bay Beach. Perfectly situated as the first unit in the building, this residence offers a...
Comfortable condo, ocean views from both lanais
Kahana Sunset E4 is a ground floor, 2 bedroom, 2-bathroom condo that features ocean views and split A/C units located in both bedrooms and the living room. Unit that can accommodate up to 7 guests. The master bedroom has a king-size bed and its own TV with cable. Enjoy...
34th Floor Ala Moana Large Regal Suite - 2Br/3Ba, Book Now at Special Rate!
Here in our 34th floor 2 bedroom/3 bath Regal Suite at the Ala Moana Hotel condo, you will experience island-style comfort in one of Hawaii's most convenient locations. This unit is located very close to the beaches and the state's largest shopping mall, Ala Moana...
Beautifully Updated & Fully Air Conditioned - Prime Location w/ Huge Lanai
Mauna Kai 5A offers the perfect combination of comfort, style, and an unbeatable location on Kauai’s North Shore! This beautifully remodeled, fully air-conditioned townhome is ideal for those looking for a peaceful and relaxing getaway, without sacrificing convenience....
Gorgeous, remodeled 3 bed/2.5 bath Ka'anapali Plantation
Welcome to your private island sanctuary—a stunningly remodeled 3-bedroom, 2.5-bathroom villa set within the lush, gated grounds of Ka’anapali Plantation, one of West Maui’s most exclusive low-rise communities. Perfectly positioned between world-class golf courses,...
Kihei Akahi Condo w/ Shared Pool, A/C-Snorkel, Surf, Swim
Kihei Akahi C418Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Step across the street and enjoy Kamaole Beach Park II, one of Maui’s best swimming and stunning beaches. Revel in the...
Professionally designed new unit at Kiahuna plantation with A/C.
Kiahuna plantation unit 427 in bldg. 41.You are a very short walk away from a beach, actually 200 steps.On the middle floor. Poipu beach is very nearby.Welcome to Sunny Poipu and Kiahuna Plantation Beach! This newly remodeled A/C .Kiahuna Plantation leaves nothing to be...
Affordable total comfort Studio at 1 of Waikiki's Top Locations, Pool & Wifi
Located in Honolulu & with a beautiful Pool, this charming studio is a dream. With a cozy living room featuring a queen bed and sofa bed, guests can unwind after a day of exploring. The bathroom offer a relaxing bathtub /shower combo with hair dryer for added...
Great 2bd condo on iconic Sugar Beach
Kihei Sands B2 is a 2-bedroom, 2-bathroom condo located on the 2nd floor that offers a three-split air conditioning system - one in every room and can accommodate up to 6 guests. Access to the second floor is by stairs only; this low-rise complex does not have an...
Luxurious Wailea Condo | Ocean Glimpses & Modern Living Palms 604
Experience the perfect blend of luxury and comfort in this beautifully updated 2-bedroom, 2-bathroom condo at the prestigious Palms at Wailea. This spacious retreat features a modern open-concept living area, plush king beds in both bedrooms, and efficient ductless AC...
Luxury Ilikai 2-bedroom 2-bathroom Unit NO RESORT FEES! FREE WIFI
Best 2-bedroom, 2-bathroom city view Ilikai unit!Great deal for a world-famous Ilikai unit over 1000 s.f. with two lanais to enjoy some cool ocean breeze.It is tastefully furnished with all you need for a comfortable stay in paradise.The Master bedroom has a king bed,...
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...
Reduced Rates for a Private Getaway In Tropical Oceanview Princeville Villa
Welcome to Your Private Island Oasis | Hanalei Bay Villas, PrincevilleTucked in one of Princeville’s premier locations, this detached villa at Hanalei Bay Villas offers the perfect North Shore escape. Enjoy easy access to world-class beaches, scenic walking trails, and...
Studio apt. with A/C, Fridge, Semi-Private pool in the Center of kihei
This is a fourth floor studio apartment, with full bathroom, near the center of Kihei. Includes A/C, fridge, coffee-maker, microwave, as well as cable TV and wireless internet. We are walking distance to the grocery store, bars and restaurants, and the beach, as well as...