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.
Kihei Beach Cottage - 1 Block to the Beach!
This cozy 2-bedroom, 1-bathroom cottage is just one block from the beach, offering a peaceful and private retreat. Perfect for a relaxing vacation or remote workers, traveling healthcare professionals, snowbirds or those in transition to longer-term accommodation. The...
🏖️Ground Floor | Private Corner Unit | Includes Concierge | vrKCV
vrKCV - The Shores at Waikoloa 102, Professionally Managed by Kona Coast VacationsThe Shores in Waikoloa Beach Resort, Unit #102Welcome to Your Dream VacationWelcome to your dream vacation at The Shores in the Waikoloa Beach Resort! Nestled in the exclusive Sandalwood...
KPL 58 Spacious 2BD Plantation Home Near Beach
Kaanapali Plantation 58 Spacious 2Bedroom Condo, a Minute Drive from Kahekili Beach 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...
Breathtaking Studio Ocean Views! Pool! Beach!
Summary:🌺 Experience the Ultimate Hawaiian Retreat! 🌺Escape to paradise in this beautifully renovated high-floor unit offering breathtaking panoramic views of the Pacific Ocean, Diamond Head, and the vibrant Waikiki skyline. Whether you're here to relax 🌊 or...
Pali Ke Kua: Paradise awaits. Enjoy Stunning Ocean Views, beach access, & AC!
Absolutely the best location in Princeville...can you say Paradise! Stunning Ocean views!The condo is beautifully decorated with high end furnishings to help you relax as you take in the outrageous views and crashing surf below. This spacious condo includes a full...
KBM Resorts | FREE CAR | The Whaler | Ocean view | 1-Bedroom, Recently Updated & Gorgeous views! WH1-1211
Serene 1-bedroom, 2-bath condo at The Whaler featuring ocean views, gourmet kitchen, king bed, pool, hot tub, and fitness center-ideal Hawaiian retreat.** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and...
Spacious & Private Home with AC & Hot Tub
This beautiful Princeville home, known as Paradiso Hale, can be found on a quiet cul-de-sac in the resort community of Princeville on the North Shore of Kaua'i. Surrounded by palm trees and colorful tropical landscaping, you'll find plenty of privacy to this pristine...
Spacious Waterfront with Gorgeous View & Pool
Waterfront home with a million dollar view of Kaneohe Bay! Enjoy fresh tradewinds on your covered decks, and the comfort of a/c inside. This custom home has spacious living areas on two levels with fast WIFI indoors AND out! 5 bedrooms, 2 living rooms, flat screen in...
KBM Resorts | FREE CAR | The Whaler | Stunning Beachfront Studio! WH1-615
Oceanfront studio at Whaler Resort with lanai, king bed, full kitchen, A/C, & resort amenities. Walk to dining, shopping, & Black Rock beach. Includes car rental for 6+ night stays in 2025!*Special Offer- Book any KBM rental home in Hawaii for 6 nights or more with an...
Beautiful Marina Sunset Views, Located In The Ilikai Hotel!
This condo is located on the 9th floor of the Ilikai Hotel. You'll have amazing views of the Ala Wai Yacht Harbor and Ala Moana Beach Park, with stunning sunset view. KITCHEN- Refrigerator- Cooktop/Oven- Microwave- Dishwasher- Dinnerware, Glassware, Silverware,...
Gorgeous Lanikai Villa with Access to Secluded White Sand Beach
This gorgeous 5 bedroom, 4.5 bathroom, gated oceanfront villa was built in 1918 and has just been fully remodeled with an open, contemporary beach house feel while still honoring the original architecture of the home. In the renovation we revealed beautiful arches...
🏖️Top Floor | Mountain, Lake & Golf Course Views! | Concierge Included
vrKCV - Waikoloa Beach Villas N32, Professionally Managed by Kona Coast VacationsWelcome to Your Waikoloa Paradise!Location, location, location! Nestled in the heart of Waikoloa Beach Resort, this top-floor villa offers unparalleled access to some of the best spots in...
Sunny and Soothing Oceanfront Vistas
Summary:Completely remodeled sophisticated oceanfront 1 bedroom, 1 bath condo, with fabulous views from the fourth floor is located in the sunny and vibrant beach town of Kihei. Beach chairs, umbrellas, boogie boards, floating noodles, luxury beach towels and a cooler...
Pacific Shores B309: Ocean Views & Comfort in Maui
Experience paradise at Pacific Shores B309, where breathtaking ocean and sunset views meet comfort and convenience on the stunning island of Maui. This 2-bedroom, 2-bathroom condo features plush queen beds in both bedrooms, with ceiling fans and screened windows that...
3 bedrooms 3 baths • Oceans views • Steps to beach
A combined rental for 2 adjacent, beautiful ocean & sunset view condos. One is a 2 br 2 bath double lanai unit and the other is a 1 br 1 bath unit. The combined space is 3 bedrooms 3 baths sleeping up to 10! You will have an ocean view triple wide lanai, 2 living rooms...
NEW 2 bedroom hosted Tranquil Island Getaway
Enjoy up country Hilo at it's finest with a new, private home in a gated community. Our 1500' elevation makes a perfect cool, peaceful evening respite after a day of beach going, hiking at Volcano National Park and enjoying Hilo's dining and entertainment. The property...
1 BR / 2 BA Oceanfront Mauna Lani Terrace Condo
The Mauna Lani Terrace is a premier oceanfront property located within the 5-star Mauna Lani Resort on the Kohala Coast of the Big Island. Adjacent to the Mauna Lani Bay Hotel on the only beachfront condominium site in the Mauna Lani Resort, the Terrace is a short...
Sweet & Cozy in Honolulu Free WIFI & AC
Discover this enchanting 1-bedroom gem in Honolulu. This tranquil apartment features 1 queen bed, WiFi, AC, a hair dryer, a washing machine, and an iron. The bathroom comes equipped with a hair dryer for your convenience. Immerse yourself in the peaceful ambiance of...
Hale Mele 2 Panoramic Golf Course Views, Pool/Hot Tub, Golf Cart & E-bikes
Welcome to Hale Mele 2 — A Private Island Retreat of Elegance and ComfortDiscover the ultimate Hawaiian escape at Hale Mele 2, an elegant 5,100-square-foot, two-story luxury residence nestled within the prestigious Champion Ridge gated community on the Big Island’s...
Hale Mahina: Gorgeous Remodeled Pupukea Home with Private Hot Tub & Ocean Views
Enjoy the Flexibility of a Monthly Stay!This property is available for monthly rentals, offering you the comfort and convenience of an extended getaway. Whether you stay for a few weeks or the full month, you'll enjoy a consistent, all-inclusive monthly rate—no need...
Puako's Ocean Edge Modern Estate - Architectural Masterpiece in Puako
Welcome to Puako’s Ocean Edge Modern Estate, an architectural tour de force on Puako’s oceanfront. Spanning 4,085 sq ft of refined interiors and 3,415 sq ft of shaded lanais, this four-bedroom, five-and-a-half-bath retreat fuses world-class design with unrivaled...
The hidden gem of Poipu.
Waikomo Stream Villas is the best kept secret in the Poipu area. An idyllic garden oasis tucked away on Kauai's sunny side, offering a premier location. Discover the finest beaches, shopping, and diverse dining options within walking distance. Convenient access to...
Hali'i Kai 19D - Newer Luxury Condo at Waikoloa Beach Resort
Hali'i Kai is just minutes away from beautiful sandy beaches, world class golf, shopping, restaurants and a host of vacation amenities. One of the wonderful features of Hali'i Kai is it's oceanfront pool area - The Ocean Club. The Club has a magnificent multi layered...
Paia Bay House: 4BR Oceanfront Retreat on Maui's North Shore
Attention, the State of Hawaii Transient Accommodation Taxes has been recently increased to 11% for all 2026 reservations. Confirmed reservations will see an invoice adjustment when the new tax law is signed by the Governor.Oceanfront property in the heart of Paia town,...
Waipouli Beach Resort Exquisite Oceanview Overlooking the Fantasy Pool
Waipouli Beach Resort Exquisite Oceanview Overlooking the Fantasy Pool and Tropical Gardens - Newest Listing! Your Dream Vacation on Beautiful Kauai in this Exquisite Exceptionally Well Decorated Luxury Oceanview Condo overlooking the Fantasy Pool at the World Renown...
Pali Ke Kua 207: Renovated Oceanview Condo w/ Peloton, Shared Pool & Spa
Welcome to Pali Ke Kua 207, a two-level vacation condo in Princeville on Kauai’s North Shore. With two bedrooms, two baths, and space for up to five guests, this updated retreat blends modern comfort with Hawaiian-inspired style. Sweeping views of the ocean and...
Once you’re here - you wont want to leave! Exquisitely appointed. Views galore
Walls of glass sliders disapear creating indoor/outdoor living. Huge covered patio plus sunbathing deck around the 15' x 30' private pool just remodeled. Located in prestigious Bayview Estates gated community of fine homes 5 minutes to beach, shops, and restaurants....
Be at the center of action while enjoying a beautifully upgraded studio with top quality finishes
Be in the center of all the action while enjoying a beautifully remodeled studio with top quality appliances, and large bathroom with double-headed natural stone shower. The view of the ocean is impressive with two lanais. You also get FREE parking & high speed Wi-Fi....
Gorgeous Renovated Oceanfront Condo - AC & Free WIFI/Parking/Cable
Located on Kona's main strip, Alii drive, this unit gives you a million dollar view in a luxurious, well-appointed setting. Take in the magic of the island, all from your oceanfront lanai. Watch sea turtles sun bathe in the tidal pool below or look out for whales and...
Polo Beach 808! Unique opportunity one-bedroom, top floor home.
Unique opportunity to stay in a one-bedroom, top floor home at one of the most desired properties on Maui. Polo Beach #808 will be your favorite place to stay when visiting the island. Top floor, corner unit with EXQUISITE VIEWS of the Pacific Ocean, Molokini,...
Kaanapali Alii | 482
Kaanapali Alii 482 is a premier vacation rental nestled within the prestigious beach vacation destination of Kaanapali. This luxurious condo offers a perfect blend of comfort, style, and breathtaking views, making it an ideal retreat for anyone looking to experience the...
Ali'i Point #12: Oceanfront Getaway w/ Hot Tub, AC, Lanai & Shared Pool
Set along the lava rock shoreline of Kailua-Kona’s Aliʻi Drive, Aliʻi Point #12 is a private oceanfront sanctuary within an exclusive gated enclave of just 16 homes. With 3,199 square feet of interior space and a sprawling 1,500-square-foot lanai overlooking tide...
🌴Luxurious Oceanfront Home on Golf Course – Paradise Awaits🌴
Set right on the golf course and ocean, this coastal style residence provides an idyllic setting for your ultimate Hawaii vacation. The 3 bed, 2.5 bath, 1,887 sq. ft. home rests along Kona Country Club's ocean course, where waves collide with the rugged coast and...
Sweet Rustic Cottage ~ Ocean View ~ Short walk to beach
A Classic Kauai Cottage on Acres of Beautiful Grounds. Away from developments and the public. More Island Artsy Than Corporate. Two ceiling fan's in living room and one ceiling fan in bedroom. One floor fan. Nice, natural breeze normally.Watch the sunrise off the ocean...
Stunning Ocean View at Kapalua Bay Villas
Kapalua translates to "arms embracing the sea" in Hawaiian. Enjoy one of the most special places on Maui at this 1-bedroom 1-bath Kapalua Bay Villa. Enjoy expansive views & the fresh island breeze from this second level unit with large bay windows & two patios. At the...
KONA CLOUD FOREST GUEST HOUSE~3 Bedrooms~
This two-story 3 bedroom home is nestled among the native forestry on the slopes of Hualalai with both mountain and ocean views. Just seven miles and a 15 minute drive to the heart of Kona town and and 14 minute drive from Kona International Airport. Nearby is Pa’ina...
Large 2 Floor Condo - Wifi/Central Air & Pool Across From Beach - Lots of Extras
The perfect place to enjoy your vacation in paradise! Centrally located and just 20 minutes from the airport, we are 1 of 54 condos in 5 buildings on 5.6 acres of beautifully manicured lawns and lush tropical gardens. This is a bright and airy, non-smoking, second...
Oceanview 1 bedroom Kihei gem, perfect location, walk to everything
Welcome to Kihei Surf 402. This ocean view centrally located 1 bedroom Kihei condo can accommodate 4 people & has everything needed to feel at home. Cross the street to get to Cove Park & Kalama Park, a favorite for surfing and walking around. This condo is steps away...
POIPU KAPILI 46 - FABULOUS OCEAN VIEWS - WHOLE UNIT AC - WALK TO BEACH/ SHOPPING
Poipu Kapili is a luxury, boutique oceanfront resort located in one of the most desirable locations on Kaua'i: Poipu. Walking in the door to Poipu Kapili 46, you will be drawn to the lanai overlooking the lush green grass, deep blue pool, and the spectacular Pacific...
Fully Remodeled Elegance in Wailea 2Bed 2Bath
Welcome to The Palms at Wailea, where we offer you exceptional experiences in a variety of realms that exceed your expectations. Nestled within the prestigious Wailea town, our villa complex exudes charm, luxury, and allure.Nestled within the exclusive town of Wailea,...
Waipouli Beach Resort Exquisite Oceanfront! Ground Level AC Pool
Oceanfront! Live the Dream! Ultra Luxury "Beachfront" Ground Floor Unit A104 at Waipouli Beach Resort & Spa offering stunning full oceanfront views from every room, with watercolor sunrises, whale watching and romantic dinners on the lanai with a 180 degree lush green...
Vacation Home in Ko Olina Resort by RedAwning
Ko Olina Kai is a peaceful gated community that offers all the tranquilprivacy you could desire! The interior is spacious and homey with 2 bedrooms,2 baths, a living room with an adjacent dining space, and a kitchen. Thisoutstanding villa offers sleeping accommodations...
ICC 20 Remodeled 2Bedroom Hawaiian Cottage w Pool AC
International Colony Club 20 Fully Remodeled Hawaiian Cottage- Walk to Beach & Steps to the Pool! 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,...
Exceptional Ocean Views - Renovated - Maui Kamaole #G-114, 1 Bd/2 Ba/ (Sleeps 2)
Welcome to your slice of paradise! Incredible ocean views, quiet, private and relaxing. The perfect place and location to call home during your stay in Maui. Note: Travelers to Hawaii will no longer be required to quarantine for 10 days provided they can provide a...
1 BR BEACHFRONT Luxury Condo at Kaanapali Beach: Escape the Crowds, Full A/C
The Mahana at Ka'anapali Beach Unit 818, Lahaina, MauiEscape the crowds of Maui resorts and enjoy private spectacular floor to ceiling views of the Pacific from this beautiful spacious 900 sq. ft. 8th 1 bedroom oceanfront luxury condo located on Kaanapali Beach, rated...
Direct Oceanfront View! Walk on Beaches - A/C
Watch the palm trees sway and whales breach from this beautifully renovated direct oceanfront unit just steps away from the white sand beach. Unobstructed panoramic views of the ocean and outer islands. Enjoy stunning year-round sunsets all from your living area and...
Lanai Building w/ AC! 100% Oceanfront -The Mahana 8th floor, 1BR/2BATHROOMS!
The Complete Maui Experience! The Mahana Resort - If you are familiar with West Maui, you will already know The Mahana is truly a premier property with spectacular oceanfront views. Just steps to the sandy Kaanapali beach, you will be led on a two and one half mile...
Tranquil Golf Course Townhome Ko Olina Kai Estates w/Great Amenities by Beach
This property requires a minimum 30-day rental. Book with confidence—professionally managed by Ali'i Beach Rentals, an award-winning property management company.Welcome to your luxurious retreat nestled within the exclusive Ko Olina Kai Golf Estates and Villas gated...
Fairway Villas Waikoloa G31-Top Floor Villa w/loft and 2025 Hilton Pool Pass!
Quite Top Floor End 2 BEDROOM 2 BATH Villa WITH A LOFT located in Fairway Villas Waikoloa in the Waikoloa Beach Resort on the Kohala coast of Hawaii island. NEW Luxury Vinyl Plank Flooring just installed and new photos coming soon. This top floor villa has enough room...
Waiulaula Villa Mauna Kea -Previous Model - Ocean, golf & mountain views!
Welcome to Wai'ula'ula' at the Mauna Kea Resort!Professionally decorated former model home with mahogany trim and stone upgrades, and now current newer updates and furnishings, offers breathtaking ocean, Maui, and Kohala Mountains views! Located overlooking the Westin...