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 Resort Rentals: Hokulani 505 – 5th Floor, Closest 2BR Column to the Beach, Superb Ocean Views!
Hokulani 505 boasts an incredible 5th-floor interior courtyard location in the closest two-bedroom column to the ocean at the entire resort. Due to its premier vantage point, Hokulani 505 is one of the few two-bedroom suites at Honua Kai offering ocean views that extend...
🏖️Well-Equipped | Close to Beaches | AC | vrKCV🏖️
vrKCV - Waikoloa Colony Villas 2306, Professionally Managed by Kona Coast VacationsWelcome to Your Big Island Escape!Step into a world of “aloha” on Hawaii's Kohala Coast, where our villa offers a truly immersive Hawaiian experience. From the handcrafted art and natural...
2026 Available Westin Nanea Award winning beach! Breathtaking Sunsets! 1/3-1/10
If you know your dates I can book as soon as the booking window opens - time stamp guarantees best views! Priced to rent! This is a one bedroom unit. If you are interested in other dates, please inquire for sister property Westin Ka'anapali Ocean Resort Villas North and...
Pet Friendly Guesthouse + Parking
LOCATION:Our Property Is Within Walking Distance To Ala Wai Canal Walking Trail, Waikiki Beach/Waikiki International Marketplace, Diamond Head Hiking Trail, Safeway Grocery Store, Restaurants, Starbucks, Jamba Juice, Honolulu Zoo, Close to Kapiolani Community College,...
On top of the Ocean Hideaway - Mermaid's Palace on Maui
Welcome to Kaimana at Pohailani Maui! Enjoy amazing ocean views, sunsets, wildlife watching, and neighbor island views of Molokai and Lanai from this well provisioned condo located on West Maui. We are located so close to the ocean you could throw a stone into the...
🌺Paradise awaits you...Come experience our "Ohana Beach Condo" 🌺
Our Maui Paradise awaits you! Be our guest at our "Ohana Beach Condos " VRBO #1628652... Our newly updated unit is on the southwest side of Maui, located next door to Wailea in sunny Kihei. This Maui resort is a complex of three beautifully landscaped buildings. Our one...
Turtle Bay Resort Oceanfront Villa - 3 Bedroom
Summary:This is the most luxurious stay you can get on the North Shore of Oahu! Our amazing Ocean Villa is one of the only two villas located in the whole Complex that allows you to have Ocean Views from ALL BEDROOMS. Unlike most houses… Our Villa was built only in 2005...
Beautiful Pacific Shores Condo 2BR, 2BA Full A/C & ready for your Maui visit!
This VRBO listing is a fully renovated and very well furnished and equipped condo located in the Pacific Shores complex in the heart of South Kihei, Maui. It is just steps away from wonderful beaches, restaurants, and shopping.The unit includes two bedrooms (each with...
Tranquil private home 5 minutes to Hawai'i Volcanoes National Park
Mauna Nani is a very quiet, secluded home surrounded by ohia trees that is close to all there is to see in Volcano. 3 bedroom 2 bathroom vacation house that truly feels like home. From the tranquil garden, to the pineapple patches and bananas, this is a great place to...
Oceanfront Top Floor Loft-Central AC, Sleep to the Sound of Waves! L-405
Sleep to ocean waves and wake to whales breaching just 25 feet from your lanai. This top-floor penthouse at Papakea is decked in original Hawaiian art and thoughtful upgrades — quartz counters, French-door oven, and a full kitchen built for real cooking. With three...
Posh Oceanview Condo w/Resort Pool & Spa, AC & Spacious Lanai - Park Lane Palm
This fourth-floor luxury suite blends island sophistication with modern comfort in the heart of Oahu's coveted Kaka'ako neighborhood. With ocean and Great Lawn views, a spacious lanai, and curated resort amenities, Park Lane Palm Resort is designed for both relaxation...
2025 Mauna Kea resort privileges are $190/day for your entire group.2026 resort privilege fee will be $225/day2100 SF 3 bedroom & 3 bath condo. Ground floor. Large wrap around lanai. Two minute walk to the community pool & exercise facility.Two full master suites with...
Executive Gold Coast Oceanfront Suite: Diamond Head Views, Amazing Seaside Pool
Executive Gold Coast Oceanfront Suite offers refined island living with nearly 360-degree views of Waikiki’s Gold Coast, Diamond Head, and the blue Pacific. This two-bedroom, two-bathroom retreat at Coral Strand blends tropical elegance, modern convenience, and an...
Stunning oceanview property minutes from dolphins
Please check out our cottage on the same property for smaller groups: Vrbo 953957 This Unique property showcases a 153 foot ocean facing deck with luxurious indoor/outdoor Hawaiian style living. Everything is completely redone and modernized. You could be swimming in...
Kona coffee farm retreat, with full ocean views near Kailua Kona!
Escape to a lush and secluded mountain retreat Kona coffee farm, just minutes away from sun-kissed beaches, Kailua and Captain Cook. Enjoy picturesque sunsets and stargaze at night. Relax in peaceful moments surrounded by full ocean views, exotic flowers, coffee trees...
Beautiful Condo Across the Street from Beach w/ Ocean View and Great Snorkeling!
Kahalu'u Beach Park is a prime spot for snorkeling, surfing and relaxing on the sandy beach. The beach is literally right walk across the street. Enjoy amazing ocean views from your private lanai, a spectacular infinity pool, hot tub and bbq area. This meticulous 2...
Ocean View, Steps away from the pool
"COVID-19: Dear travelers. Even though we have always maintained an exceptionally clean property, you can rest assured that we are following the guidelines of the CDC and Expedia/VRBO for enhanced cleaning and disinfecting of short term rentals. Additionally, the State...
Lucky you! 2 Bedrooms, Large Lanai, Stunning Mountain Views, Pool, Parking, W / D
Whether you are coming to Waikiki on business or just to escape the stress of business with a vacation, you will find this 2 bedroom condo in a very desirable building your perfect tropical oasis. Designer -inspired décor echoes the peaceful colors seen in the expansive...
Beachy style, chic studio renovated to 5-star standard with partial ocean view. Centrally located at Marine Surf Waikiki on 21st floor. Just steps from the beach, world-class shopping, restaurants, and attractions. One block from Royal Hawaiian. Enjoy a sleek place to...
Right On the Water, Stunning Ocean views and Sunsets, AC, Elevator, Pool
Hale Kai a 2 bedroom condo at the oceans edge overlooking two amazing surf spots our condo is breathtaking for relaxing and listing to the ocean waves and watching the magnificent sunsets! Enjoy coffee in the morning while watching dolphins frolicking and seasonal...
Ho'olei Villa 17-1: Luxury Retreat with Breathtaking Ocean Views
This property is hotel zoned, and not being affected by the recent proposed legislation.Luxury at its finest! Ho'olei Villa 17-1! Mesmerizing ocean views and bright open floor plan welcome you. Enjoy the beautiful Maui sunsets on your expansive private lanai.One of the...
Stunning Ocean View - Steps from the beach - Kahala 623
Kahala 623 is a 1,000 square foot condo overlooking the immaculately kept Poipu Kai greenbelt with barbecues and walkways leading down to Brennecke's Beach. Imagine yourself sitting on the lanai, your favorite beverage in hand, a gentle trade wind flowing over you as...
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...
Exquisite Oceanview Villa with Resort Amenities in Gated Community
This property is hotel zoned, and not being affected by the recent proposed legislation.Located in highly desirable secluded area of neighborhood your villa welcomes you with spacious floor plan and sweeping ocean views. Marvel at the beautiful Maui sunsets from your...
Indulge in Luxurious poolside living: Ground Floor Condo in Waikoloa
Upgraded Ground-Floor Villa | Steps to Pool & BBQ | Walk to Shops & BeachWelcome to Waikoloa Beach Villas D2, a beautifully upgraded 2-bedroom, 2-bath ground-floor villa in a private gated community on the Big Island. Just steps from the resort-style pool, hot tub, and...
Kahala Breeze: Modern Tropical Home with Pool & Private Yard
Kahala Breeze by Gather is a refined island retreat in Honolulu’s prestigious Kahala neighborhood, offering relaxed luxury just minutes from beaches, shopping, and dining. This spacious four-bedroom residence features a private pool, tropical landscaping, and seamless...
Aloha Villas # 4, Luxury Oceanfront Townhouse, Steps to Beach
Summary:"Eha" - Aloha Villa #4 presents an exclusive seaside escape in Maui, blending luxurious comfort with breathtaking ocean views for an idyllic vacation.The Space:Imagine this: stepping off the plane and into paradise at Aloha Villas, a beachfront complex in South...
Spacious, Private Villa Ideal For Extended Or Multiple Family Rendezvous
This stunning 10,000 square foot, slate and mahogany floored, 7-bedroom open air Villa is your own private paradise. Enter the expansive foyer through the beautiful etched glass double doors to step down into the 2 1/2 story living room capped with a traditional...
Aloha Villas 3, Oceanfront Townhouse, Steps to The Beach, Great Location
Summary:"Ekolu" - Aloha Villa #3 offers a unique blend of tranquility and luxury, set against Maui's breathtaking beachfront backdrop. Perfect for your island retreat!The Space:Imagine stepping into your luxurious Hawaiian home away from home at Ekolu Villa. Nestled...
Ali'i Kai 1-202 · Beautiful Mountain View Condo in Princeville
Recently remodeled 2-bedroom, 2 bath condo close to many amazing beaches. This unit features great mountain views and you can even peek at the ocean from the dining area to check out the swell. Close to restaurants, spas, shops, golf, and tennis this is the perfect...
Kukuiula Cottage #27 By Parrish Kauai
This handsomely designed and decorated Kauai cottage offers the details of early plantation days yet with the modern conveniences of central air conditioning, as well as everything else one needs to indulge themselves on a luxury Kauai vacation. Enjoy the lush garden...
Kona Awesome Tropical PoolCottage/AC/GreatLocation
E komo mai ! Our guests highly recommend the mail in VAULT Covid test. You mail it UPS and your results are emailed to you within 72 h. https://www.vaulthealth.com/covidWe look forward to welcoming you to our home and our newly established Ohana/ Studio in a beautiful...
Cozy Hideaway in the Ohia Rainforest Located Below Volcano National Park
Entire house 2 bedroom full kitchen 1.5 bath washer&dryer and a screened in lanai on 2 acres of ohia forest with fruit trees private and quiet with lock box for entrance....some of the things that I provide is lot of clean towels a full kitchen with fridge stove...
High on a hill overlooking Ekahi with Great Ocean Views!
Situated high on the hill overlooking Ekahi Village, our Ekahi 46D condominium offers great views of the ocean from the living room, kitchen and lanai.The vaulted ceilings in this 2nd level condo enhance its open and airy feeling and nicely displays the Hawaiian wall...
Blue Hawaii: Luxurious Oceanview Home with Pool, AC & BBQ Lanai
Blue Hawaii by Gather delivers a grand island escape in Kona’s sought-after Keauhou Estates. With 3,200 square feet of interior space, an expansive solar-heated infinity pool, and multiple private sleeping suites, this home was designed for large groups to relax,...
Luxe Tropical Retreat w/ Private Pool, Spa, AC, Golf Cart Included
Set within the prestigious KaMilo community at Mauna Lani Resort, this beautifully designed split-level residence offers more than 2,400 square feet of refined indoor-outdoor living. With a private pool and jacuzzi, lush tropical landscaping, and elegant interiors...
Spectacular Oceanfront View at Hanalei Bay Resort 9101,2,3 - 6 min walk to beach
One of two full oceanfront views of Hanalei Bay with private lanais and grass lawn looking over the breathtaking views of Hanalei Bay and Bali Hai. Enjoy an amazing sunrise breakfast and cup of coffee as you overlook the bay as the sun wakes up the sparkling Pacific...
Stunning Oceanfront Property! Spectacular Ocean Views!
This exceptional oceanfront Penthouse is located on the sunny, south shore of Hawaii's Garden Island in Poipu. This beautifully remodeled, luxurious condo is just 30 feet from the ocean's edge. It offers 180-degree ocean, coastline and mountain views from the lanai,...
Newly remodeled gem in Hawaiian Shores
Spacious Custom built newly remodeled 3bd 2ba home with 2,144+ sqft of living space that has been beautifully remodeled/renovated for enjoying Island living.This home features vaulted ceilings, natural light with French Doors opening on to your spacious front...
Summary:Escape to paradise in this spacious 3-bedroom, 3-bathroom townhouse in Kailua-Kona! Enjoy stunning ocean views and sunsets from your private lanai. This fully-equipped condo in a quiet, gated community offers all the comforts of home, including a BBQ grill and...
Kona Reef D24 - Direct Ocean Front Condo - Private Lanai - Next to Honl's Beach.
Welcome to our beautifully decorated ocean front condo in paradise - Kona Reef D-24. Our condo is our home away from home, so we respectfully request a maximum of 2 adult guests and no children under 18. Whether this is your first trip to Kailua-Kona or you are a...
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....
Enjoy Grand 2BR, 2 Baths, Executive Condo Near Beach and Everything Else
Discover Luxury Living in Honolulu Near the Beach and Everything ElseWelcome to a stunning 2-bedroom, 2-bathroom, fully furnished rental perched on the 15th floor of Yacht Harbor Towers in picturesque Ala Moana, nestled between Waikiki and Kakaako. This spacious 1500...
Downstairs master bedroom has A/C, kitchenette, and a private entranceBig screen smart tvs in all three downstairs bedroomsLarge upstairs 2nd master bedroomFully stocked kitchen, including DeLonghi espresso machine, Instant Pot, Vitamix blender (for the BEST smoothies),...
Private Oceanfront w pool, hot tub, sunsets and Turtles
Front row center for Humpback whales (Dec-April) - from the lanai or from our kayaks ! Enjoy our beautiful, tastefully decorated Oceanfront 3 bedroom home (BBKM 2019/0003), accommodating up to 6 adults and 2 additional children. Kihei is the sunniest part of Maui and...
4 Bdrm Luxury Golf Course Home with A/C
Welcome to Molokama. Walking distance to a white sand beach through Hanalei Bay Resort in Princeville, Kauai. The home overlooks the Robert Trent Jones designed Makai Golf Course. The 4-bed, 3-bath home sleeps 8 comfortably. 4 bikes, beach gear, outdoor shower. Master...
Luxury Kapalua Ridge Villa Featuring Sparkling Ocean, Island and Coastal Views!
Property Highlights • Five minute walk from three world-class beaches, including Kapalua® Bay, rated the "Best Beach in the World" by Dr. Beach, and “Best Beach in the US,” by Conde Nast • Large lanai for optimal outdoor living space • Better-than-Gold custom remodel...
Brought to you by Paradise in Hawaii Luxury HomesWelcome to Flora Paradise Villa, a part of our Hawaiian Luxury Collection. Flora Paradise Villa at KaMilo is a gorgeous 3 bedroom, 3 bathroom home, with two master suites. This beautiful home has been professionally...
Enjoy one week of elegant luxury in my two bedroom unit right across from Kahana Beach. Check-in days are Wednesdays, Fridays and Saturdays. Amenities include pool, tennis courts, and air conditioning. Test the waters of nearby beaches famed for swimming, body surfing...
This vacation home is your destination if you desire privacy, have a family or want a laid-back vacation. This luxury home is ideal for large family gatherings. The house is located on a secluded one-acre, tropically landscaped lot in a quiet, quality Hawaii...