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.
Ocean-view hideaway with pools, hot tub, tennis & grill - beaches await
Maui Kamaole G102Our 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...
Hale Kamaole Condo w/Private Washer/Dryer & Shared Outdoor Pool- Small Dogs OK
Hale Kamaole 106Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Hale Kamaole is a South Maui condominium complex located across the street from Kamaole Beach Park III, one of the...
The Watermark (WM1102) Luxury 11th-floor 2 BDR, balcony, AC, remote work
This luxury 11th-floor two-bedroom apartment with balcony, parking will surely become your sweet home away from home allowing you to conveniently work from Hawaii. You will be in close proximity to Waikiki Beach and Ala Moana Center.Upon arrival, you will step into a...
Island Sands Resort Condo w/ Free WiFi, Ocean View-Near Everything
Island Sands Resort 107Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'The Island Sands Resort on Maui is located oceanfront in Maalaea, just a short four miles to Kihei and a scenic...
Spring Specials! Sweeping Ocean and Golf Course Views!
This is a wonderfully, updated condo in Waikoloa Village with sweeing ocean views! Don't miss out on staying here and enjoying quiet sunsets on the lanai overlooking the Trent Jones golf course with 180 views of the coastline. This complex offers the best views in...
Outstanding Oceanfront Views - Mahana 1017
Outstanding ocean front views on North Ka'anapali beach. Located in the Lanai Tower, enjoy heavenly sunsets from your living room AND bedroom. This condo has been totally remodeled and is tastefully decorated with an island style theme. The kitchen has granite counter...
Gorgeous 2bd condo - walk to the beach
Ocean Views | Walk to Beach 2 Bedrooms • 2 Bathrooms • Sleeps 6 • 3 BedsWelcome to paradise at Kihei Akahi D502! This updated 5th-floor corner unit in sunny South Maui offers breathtaking ocean views, a private lanai, location just steps from Kamaole Beach Parks...
Oceanfront condo with shared pool, hot tub, beach access & private balcony
Kona Bali Kai #351Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'The Big Island is just waiting to make your next vacation one for the books here at Kona Bali Kai #351. Sitting...
Waikomo Streams 203: Luxiuous 1BR Condo w/ Pool
Strolling the grounds of Waikomo Streams Villas in Po‘ipū is like walking through a tropical paradise. A bamboo forest, brightly colored flowers, and a waterfall spilling into a serene pond where multi-colored koi swim are all waiting to be discovered on the property...
Ground Floor Garden Studio - Kaanapali Villas B143
Maui Kaanapali Villas #B143 on the ground floor: Convenient ground floor garden view studio condo at the beautiful Maui Kaanapali Villas on Kaanapali Beach. Located in an excellent location in the Banyan Building with no stairs and the ability to walk right out your...
Maui Vista Condo w/ Pool & Tennis Courts - Walk to Beach & Local Restaurants
Maui Vista 2116Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Discover island bliss at Maui Vista! Nestled across the street from the ocean, you can stroll to the soft sand at...
Kauhale Makai 512: Stunning views of the Pacific Ocean and Mountains
Enjoy a stunning view of the Pacific Ocean and the West Maui Mountains from this two (2) bedroom Condo. This unit has a queen bed in the master bedroom, two twin beds in the second bedroom and a pull-out sofa bed in the living room, allowing this unit to accommodate up...
Sugar Beach Resort 334: You will Feel like you're Sitting on the Water
Sit on your lanai and enjoy the Ocean Front views that will make you feel like you are sitting on the water. This third-floor condo has one bedroom and one bathroom. The bedroom has a king bed and the living room has a pull-out sofa bed, allowing this unit to...
Kona Bali Kai studio w/pool, spa, & WiFi - steps to Banyan Surf Beach
Kona Bali Kai #234Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'As part of the exclusive Kona Bali Kai Resort, this updated studio features a private balcony. Take a dip in the...
Kihei Akahi C-607 | Ocean Views, Two Pools, Tennis
Unwind in paradise with this homey condo on the sixth floor. With its comfortable furnishings, community pool, an ideal location, you’re sure to have the vacation of a lifetime!Warm, wooden floors lead you into the bright and spacious living area of Kihei Akahi C-607....
Ocean-view condo on top floor with lagoon pool, hot tub, AC, W/D, great location
Maui Kamaole A214Our 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...
Gardenia Studio #5
This beautifully renovated studio is located in the heart of Hilo town and is ready to welcome guests who will appreciate its transformed space. It features a bright and well-equipped environment that is both calming and inviting. The studio includes a new queen...
Tropical Maui Garden View Condo in Ocean Front Location just North of Kaanapali
Welcome to Maui Sands #6E. Just steps from the ocean with garden views in Honokowai. This second floor condo is on the corner of the building where you can find a peek-a-boo view of the ocean. There are stairs to the entrance, but no elevators. A window air conditioning...
Ground-floor getaway w/ a furnished patio, shared pools, grills, & shuffleboard
Plantation Hale E7Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'This ground-floor home is in the perfect spot for the ultimate Kapa'a vacation. Inside this comfortable condo,...
Charming home w/ wood stove - 10 minutes to Hawaii Volcanoes Nat'l Park
Kahu 'lo - Guardian HawkOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Your next volcano adventure awaits at this Big Island home, beautifully situated on a property filled with...
Ocean & Lagoon Views
Luxury Oceanfront Condo in Waikiki – Stunning Views & Prime LocationExperience the beauty of Waikiki Beach from this exceptional oceanfront two-bedroom, two-bath condominium at the renowned Ilikai, famously featured in the original Hawaii Five-O series. Wake up to...
Two comfy Queen beds at The palms Waikiki - Pool & Lanai
Legally permitted rental - 1850 Ala Moana Blvd #321** For your health and safety, we utilize additional Sterilization procedures between reservations.A super comfortable remodeled unit, this 2x Queen bed Studio suite at The Palms is the perfect place to call home for up...
Ilikai Hotel 909 2-Bedroom Suite in Lovely Waikiki
Scenic 2-Bedroom Ilikai Hotel Suite in the Heart of WaikikiWelcome to the Ilikai Hotel 909 2-Bedroom Suite, a spacious and inviting accommodation in the heart of lovely Waikiki. This well-appointed suite features two good-sized bedrooms with en-suite bathrooms at...
Oceanview -KUL207 - West Maui - Spacious Remodeled Condo in Quiet Oceanfront
** Discounted Rates through Summer 2025!! **Unit #207 is an absolutely stunning vacation rental, adorned with luxurious features that will make any guest's stay unforgettable. As soon as you step foot into the unit, you are greeted by exquisite travertine tile, which is...
Pono Kai Resort Condo w/Free WiFi, Shared Pool, Shared Grill-Close to Beaches
Pono Kai Resort J101Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Pono Kai Resort is the perfect choice for rest and rejuvenation. Well-known for its family-friendly environment...
Second-floor, oceanfront condo with high-speed WiFi, balcony, & pool
Mahina Surf 225Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Step through the door, drop your luggage, and relax at this delightful, second-story condo offering spectacular ocean...
Queen bed plus Sofa bed Balcony Studio & Pool
Pool & BBQ area included!Offering a recent upgrades, this gem Studio suite at The Palms will have you and the family returning year after year.A very comfortable Queen size bed for you and an easy to set up Pullout Sofa bed for 2 additional guests.Fresh white cotton...
Low rise, tropical oasis, corner, spacious lanai and kitchen, AC and pool.
This charming corner townhome is located in the heart of Puamana. It features a spacious kitchen, Berber carpeting, glass block accents, an expansive kitchen garden window, and tropical decor. The home’s corner position allowed for new kitchen designs and additional...
HOL 120 Oceanfront 2BR Cabana Unit Direct Beach Access AC Poolside BBQ
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...
Kona Nates Ocean View Escape
Welcome to my Ocean View Escape! Located in the heart of Kona, you will have an unobstructed view of the West Hawaii sunset every night! From the kitchen you can even see the sunrise over the mountains every morning. Located in Downtown Kona, you can walk to all of the...
Shores at Waikoloa Unit 301: 1 Br condo in the Sandalwood Tower Sleeps 4
This resort features many great amenities for its guests to enjoy. There is a swimming pool and hot tub on the property where you can enjoy the cool water in the Big Island weather. The resort also has a tennis court and fitness center for those days you want to do it...
Peaceful Island Beach Escape on the North Shore of Kauai!
Relax in paradise at Pali Ke Kua, a peaceful retreat nestled in the heart of Princeville on Kauai’s lush North Shore. Enjoy sweeping views of the Hanalei mountains from your private lanai, or take the private, paved path down to the secluded Hideaways Beach—one of...
Wavecrest Resort C316
Wavecrest C316Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'This is a beautiful two-bedroom, one-and-a-half-bath, ocean view condo, located on the third floor of the C complex at...
Cliffs at Princeville #1208B, Ocean-Bluff Resort, Room w/Lanai
The Cliffs Resort at Princeville Unit 1208-B, Private Room on the beautiful North Shore.The Cliffs Resort, Princeville is located on 22 lush acres of tropical gardens perched above the blue Pacific Ocean on Kauai's beautiful North Shore. Accommodates up to 2 guests,...
The "Hula’s Hideaway" just 20ft to the Bar!
Legally permitted rental ✈Waikiki Grand Hotel134 Kapahulu Ave #216⚕⚕For your health and safety, we utilize additional Sterilization procedures between reservations.Located at the Waikiki Grand Hotel & just 20ft from the world famous Hula's Bar & Lei Stand. Enjoy...
Kaluako'i Resort Cottage 1A Beachfront Rental - Molokai, Hawaii
Experience spectacular sunsets, white sand beaches, and gentle breezes as you put the cares of this crazy world aside. Relax and step back into the tranquility and natural beauty of this island, rich in the history and culture of old Hawaiian moods and customs. It is...
Fall Special! Hale Palila Volcano A-Frame Cottage with Hot Tub
Nestled on a golf course, this Volcano (Big Island, Hawaii) this large Hale Palila A-frame cottage is 5 minutes’ drive from the entrance to Hawaii Volcanoes National Park. There is a Queen bed in the loft area, and 2 sofa beds in the living room area to sleep up to 6...
Kailani #314, Top Floor, Walk to Kapaa Town and Beach
Kauai Kailani #314, Kapaa, Hawaii. Kauai vacation rental conveniently located in Kapaa Town on Kauai’s Royal Coconut Coast. This cute boutique condo is walking distance to shops, restaurants, coffee shops and more! Accommodates up to 4 guests, including children and...
15th Floor - Heart of Waikiki with Balcony Sleeps 4
Legally permitted rental - 444 Kanekapolei St #1507** For your health and safety, we utilize additional Sterilization procedures between reservations.Our studio has a air-conditioning, kitchenette area with fridge, counter-top hotplate for cooking, microwave,...
Ocean & Diamondhead View 1 bedroom at the Waikiki Sunset
Welcome and Aloha!This 20th floor unit of the Waikiki Sunset is fully furnished with one king size bed in the bedroom, one queen size sofa bed in the living room, and kitchen counter with four dining chairs.The full size kitchen has everything you’ll need to feel...
Best Deal Luxury Resort in Town Sleep 4 romantic, fun and relaxed
Note: if the requested dates are not available, I also have three other rooms on the property, VRBO #579874, #666626, and #595354, vrbo#460973, #492665.The Kauai Beach Resort - a gorgeous boutique is located along three miles of secluded beach in Lihue, Hawaii. Lihue...
Ilikai 1434 2 Bed Room Ocean/Lagoon Views Extended Lanai - Qn Bed + 2 Full
OCEAN / LAGOON VIEWS! STEPS TO WAIKIKI BEACH. 2 bedroom, 2 bathrooms, 120 sq. ft lanai, 1,000 interior sq. ft. Queen bed, 2 double beds. Walking distance to parks, shopping mall, restaurants, shops, buses, rental cars, parks.The Ilikai Suites are located at the gateway...
Great Ocean View 1 Bedroom, Full Kitchen,
** Waikiki Banyan pool deck closure. Starting April 1st and lasting about 10 months, the pool deck including swimming pool, hot tub and other pool deck amenities will be closed for a major remodel. Our nightly rates have been adjusted to reflect this closure ** One...
Well Updated, Sleeps 4, One Block to Beach
Legally permitted rental - 2425 Kuhio Ave. #308** For your health and safety, we utilize additional Sterilization procedures between reservations.The Bamboo Hotel is one of only three Waikiki hotels designated as a New York Times Pick. Called 'A hidden gem' on a New...
Rich & Dana's Ocean Front Condo With Spectacular Sunsets
Our condo is located in Bldg 25, #2253 on 'Malibu Row', as the owners call it...because everyone wants to live with unobstructed blue and white water views and sunsets from our lanais. Listen to the beach's surf surrounding the famous Kaliaka Rock (where Dole Pineapple...
Only 100 steps to Poipu Beach with A/C!
Only 200 steps to Poipu Beach and Brennecke's Beach Restaurant. This two bedroom is fully furnished with 2 queen beds, air conditioning in the bedrooms, TV in every room, FREE Wi-Fi, and fully stocked kitchen. This is the perfect vacation rental for singles, couples or...
Top-floor condo with mountain views, washer/dryer, 2 pools & 8 tennis courts
Hanalei Bay Resort 2301Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Hanalei Bay Resort 2301 is an air-conditioned, top-floor condo in a three-story building in Princeville, where...
Golf course-front, ground-floor condo w/private lanai, shared hot tub, pool, A/C
Waikoloa Fairways C119Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Paradise and endless sunshine await at this incredible and family-friendly condo! Bring your clubs and try out...
Huge, private lanai with panoramic view of Diamondhead
Located in a quiet neighborhood three blocks from Waikiki Beach. Decorated in tropical, Hawaiian decor, this unique condominium offers a complete kitchen as well as a 1000-square-foot, private lanai with an extraordinary view of Diamond Head crater. Relax by the heated...
AKH C616 Kihei Condo w Pool Ocean Views Across Beach
FREE daily activities included with your stay value up to $554! Complimentary admission, every day of your stay*: Whale Watching (seasonal), Sunset Dinner Cruise, Molokini Snorkel Trip, Alpaca Farm Tour, Pineapple Farm Tour, and Tea Farm Tour. (S1)*One ticket per...