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.
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...
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...
Oceanfront Resort, 4 pools, 75 foot waterslide, restaurants on site
Our unit is a privately owned hotel room located in the Outrigger Kauai Beach Resort and Spa.This is a serine second floor unit with 2 Queen beds and a view of the park and partial ocean view from the balcony. New flooring was just installed in the unit!!The Outrigger...
Ilikai 1118 Ocean / Lagoon / King Bed, Sofa Bed
STUNNING OCEAN / LAGOON VIEWS! STEPS TO WAIKIKI BEACH. Memorable Meals and fireworks from the Lanai. Walking distance to shopping mall, restaurants, shops, buses, rental cars, parks & Waikiki night life.The iconic Ilikai Suites are located at the gateway to...
Ocean and Diamond Views from the Balcony
Legally permitted rental - 134 Kapahulu Ave #911** For your health and safety, we utilize additional Sterilization procedures between reservations.This unit features breathtaking views of Diamond Head, Kapiolani Park and Kuhio Beach. Enjoy Sunrise and Sunsets, movies on...
Hale Kamaole 141 Ground floor condo, easy access to best beach on Maui!
This one bedroom condo with Garden View, is located near pool in upper complex and has beautiful Hawaiian decor throughout the living room and bedroom. The kitchen has spacious counter tops with new wooden kitchen cabinets. Our living room has a great TV with sofa...
Hilo Hibiscus Vacation Home 3 bedrooms
Consider this house your home away from home while you visit Hilo. This fabulous property boasts 3 bedrooms, each with its own unique charm.Start your vacation at this centrally located home, surrounded by shopping centers, restaurants, parks, and beaches! If you are...
Turtle Bay Condo in Kahuku - Kuilima Estates East
Cozy, spacious 1 bedroom+ loft and 2 bathroom upstairs condo. Air conditioning in the bedroom only but great breeze from lanai and beautiful view of golf course. Free WiFi. Tucked away in quiet location close to pool. Two bathrooms, one on the main floor with tub and...
Spacious 1 BR/1 BA Keauhou Gardens condo at Kona Coast Resort
Keauhou Gardens 11-101 is a spacious one bedroom/one bath unit located in the Keauhou Gardens section of the Kona Coast Resort situated on 21 acres of beautifully landscaped tropical Gardens.Keauhou Gardens 11-101 is a privately owned unit with access to all the...
Corner studio with mountain/bay views, lanai, AC, 2 pools & 8 tennis courts
Hanalei Bay Resort 4206Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Hanalei Bay Resort 4206 is a coveted corner studio, offering gorgeous views of the resort's tropical grounds...
Maui Sunset A105 ~ 1 BR, 2 BA Ground Floor Condo!
One bedroom, two bath partial ocean view ground floor condo. Close to the putting green. Located next to Waipuilani Beach, which is a long sand and coral beach protected by reef and suitable for swimming, long walks, whale watching and beautiful Maui sunsets. This area...
🏄New Top Hawaii Oceanfront 2BR/2BR with White Sand Beach🌊 - Kona Bali Kai 206
Breath in that Beautiful Ocean Sprayfilled Air at this Oceanfront 2nd Floor Amazing Condo with Lanai Boasting Stunning Sunsets & Vews of the Kona Coast. Excellent proximity to Kona Town, golf, Ali'i drive beaches. Whales, surfers, spinner dolphins and sea turtles all...
King Bed Suite at The Bamboo Hotel a central Waikiki Oasis
Legally permitted rental - 2425 Kuhio Ave. #709** For your health and safety, we utilize additional Sterilization procedures between reservations.This studio suite is complete with a 2 burner cook-top, microwave, some kitchen prep tools, a coffeemaker, beach towels,...
Kihei Akahi Condo w/ Free WiFi, Private W/D-Waves Await
Kihei Akahi C501Our 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...
Shores at Waikoloa Unit 307: 1 Br condo in the Sandalwood Tower, Sleeps 4
Located on the west coast of Hawaii Island (The Big Island) known for its many golf resorts, Shores at Waikoloa is a gated condominium resort community nestled between two Waikoloa golf courses. A stress-free alternative to mega-resorts-Shores at Waikoloa offers a...
Maui Vista 3201: Your ideal retreat! Steps from beaches, dining, and The Cove!
Remodeled in 2024! Maui Vista 3201 is one of the best locations in Kihei! This 1 bedroom, 1 bath condo is the perfect retreat for your Maui getaway with beaches, dining, shopping, and golf all within minutes. It's just a block away from a favorite local surf spot, The...
Beautiful Beachfront ocean view Maui Condo
This beautful resort is located in South Kihei, next to the Hawaiian Islands Humpback Whale National Marine Sanctuary and ancient Royal Hawaiian Fish Pond of Kalepolepo. This vacation rental condo offer amazing views of the Pacific Ocean, West Maui Mountains,...
BEAUTIFUL & WELL LOCATED at AQUA PALMS - WAIKIKI
Legally permitted rental - 1850 Ala Moana Blvd #815** For your health and safety, we utilize additional Sterilization procedures between reservations.Beautifully remodeled hotel room comfortably accommodates four adults and is located steps from Waikiki Beach and the...
Light & Airy 8th Floor Ocean View Condo with Lanai and FREE Parking!
Waikiki Banyan Tower 1 Suite 802Light Airy 8th Floor Ocean View Condo with Lanai and FREE Parking!The pool and all associated amenities will be closed starting April 7, 2025, for an estimated duration of 10 to 14 months to accommodate the Recreation Deck renovation...
Palms at Wailea 1302! Top floor condo with Amazing Garden and Ocean Views!
Top floor condo, #1302 overlooks the lush, landscaped grounds of Palms at Wailea out to a beautiful view of the Pacific Ocean. Watch whales breaching in Winter months and enjoy glorious sunsets year-round.Plenty of windows and glass doors throughout make this home a...
Compact Studio with Balcony next to Hula's Bar & Lei Stand
Legally permitted rental - 134 Kapahulu Ave.The Waikiki Grand has been a longtime favorite for many guests returning year after year. This newly renovated Studio is just a few feet from Hula's Bar & Lei stand.Enjoy step free access from your front door straight into one...
On the oceanfront in sunny Kihei, large private ocean view lanai
Just fantastic location and awesome views of the pool, ocean, palms in the tropical oasis of Maui Sunset. Super popular, wonderful location just easy access to pool, grounds, and amenities of the Maui Sunset. Large private condominium apartment at the resort condominium...
Whaler on Kaanapali Beach Vacation Rental: 6th Floor; Tower 2; 1/1 Ocean View
Ocean views on Kaanapali Beach from the South tower facing Black Rock. In addition to the TV in the living room there is also a TV in the bedroom. A true gem of the West side, The Whaler on Kaanapali Beach is a Maui vacation opportunity that you can't miss. With an...
Close to Beach, Gorgeous views & Pool - Sleeps 4 Adults & 2 kids
Located on the 23rd Floor of the The Pacific Monarch Condotel - The 1 bedroom property with kitchen has stunning views of Waikiki, Plus the Ocean, Diamond Head & mountain range.The Bedroom offers a Queen bed with Smart TV, dresser, closet & ceiling fan.The main living...