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.
Absolutely Stunning Oceanfront Condo!
It’s private and quiet. This is your perfect Hawaiian getaway! Wake up with this stunning view of the Pacific and fall asleep serenaded by the melody of the ocean. While you bask in the sun, enjoy the company of many sea creatures (turtles, dolphins, and whales). All...
New Years Week 12-28 to 1-4-26 Westin Kaanapali Ocean Villas 2 br island view
PRICE REDUCED to $850/night -- basically the cost for one, small, standard resort hotel room nearby! This two-bedroom, island-view unit is available (as of now) for seven nights, checking in on Sunday 12/28/25 and checking out on Sunday 1/4/26. Why not spend two holiday...
2021 Toyota Tacoma with a Rooftop Tent and all the camping gear!
2021 Toyota Tacoma TRD Sport with a Pop up tent! Our camper truck comes with all the amenities! Travel around the lush island of Maui and stay in a different part of the island every night!! Book your adventure today!! We provide everything you need from bedding &...
Excellent for couples or families. Right on the Golf Course.
Our villa provides 2 Bedrooms and 2.5 Baths, totaling over 1400 square feet plus 2 Lanais. It is perfect for families or couples vacationing together. The well-appointed kitchen has beautiful maple cabinetry and granite countertops. Eighteen-foot vaulted ceilings in the...
RELAXING, Away-from-it-All home on the water with small Natural Pool
Hale Pali (Cliff House) is a spectacular (non-smoking) OCEANFRONT home overlooking the blue Pacific. We heartily agree with our guests who have enthusiastically stated: 'there is nothing that compares to actually being on the water' - what better way to enjoy the sound...
Kaanapali Alii | 296
Kaanapali Alii 2962 Bedrooms | 2 Bathrooms | Sleeps 8 | Mountain View________________________________________Discover the perfect Hawaiian escape at Kaanapali Alii 296, a stunning two-bedroom mountain view condo on the ninth floor that offers a blend of luxury and...
Kukui'ula Villa 8: Oceanview Condo w/AC/Private Lanai, Walk to Shops/Restaurants
Escape to Kukui'ula Villa #8 by Gather and settle into a refined island retreat in the heart of Poipu. This second-level villa blends chic contemporary design with sweeping ocean, garden, and mountain views, offering 1,484 square feet of bright, breezy living space....
Oceanfront Property - 60 feet from the ocean. Beautiful views, free WiFi
***Facility Fees will be waived at the Papakea Resort, beginning July 1st!***Note: The owners own a second unit on the same floor, L-205, so the two can be booked together for larger groups and families. Welcome to Papakea! Located between the Kaanapali and Kapalua...
Stunning Ocean Front Studio! Mahana 803!
STUNNING VIEWS OCEAN FRONT STUDIO MAHANA 803! NORTH KAANAPALI BEACH, A/CWelcome to Mahana 803! Located on the eighth-floor, this oceanfront studio sleeps 2 and features stunning panoramic views of the ocean, beach and outer islands. Living area highlights include tile...
Cozy 1-bedroom with AC and WiFi in enjoyable Kailua-Kona
Welcome to Hale Kai Hideaways, Bungalow A. Vacation at this cute apartment centrally located in the heart of Kona. Alii Garden's open-air marketplace is a five-minute walk, where you will find Shaka's tacos, local coffee & tons of souvenirs. Turtles Beach, a local...
Ocean Front! Includes Waikoloa Golf Membership Benefits. Halii Kai 13A
This vacation rental is professionally managed by ResorticaHawaiiHalii Kai 13A. Includes Waikoloa Gold Golf Membership DiscountsPlease scroll down for detailed informationBedding Configuration:Master Bedroom: King BedGuest Bedroom: King Bed and 1 Twin Fold Out Chair...
Wai'ula'ula M101 - Ground-Level Oceanview Residence
This corner, ground-level, oceanview residence offers a great room with sliding glass pocket doors for indoor/outdoor island living, a chefs' kitchen outfitted with Sub-Zero, Fisher & Paykel and Wolf appliances/gas range, dual master suites with California king beds....
Steps Away From Poipu Beach * A/C * Newly Remodeled * Family Friendly
Remodeled bright, beautiful, breezy top floor, corner unit in Building 23 on Kiahuna Plantation. Located 100 yards from Top 5 Rated Poipu Beach. Fabulous expansive views of gardens, twin bridges and lagoon. A new cal king bed in the master and a new queen sleeper sofa...
Maui Retreat Ekahi 50F, All YOU Need! 5% off for stays over a week!
The rest of JUNE $299 per night!Waiting for you to come and unwind. Just bring yourself, everything else is HERE! Towels, beach chairs, umbrella, boogie board, whatever you need!!!This beautiful second floor unit has an open, beautiful garden/mountain view. The vaulted...
Lei Aloha - A Private Retreat, Pool + Fairway views
Welcome to Lei Aloha, Princeville!This luxurious island home is a 4 bedroom, 4 bathroom home combination of elegance filled with an abundance of amenities. This hidden retreat located in the prestigious resort community of Princeville is one of its kind , and provides...
❤️PiH❤️ Hono Loa ★ Bikes/Beach Toys ★ Private Beach Club ★
Presented by Paradise in Hawaii Luxury HomesWelcome to Hono Loa at the Fairways in Mauna Lani!Hono Loa offers the ultimate backdrop for your Hawaiian getaway. Perfectly designed to accommodate up to 6 guests, it's an inviting, luxurious, and serene retreat for both...
Oceanfront Home with Pool ‘The Cove at Milolii'
Front row views of Kona sunsets Our two-story oceanfront home has views from every room and tropical breeze flowing from roof top cupola through every window and door. The main living area is upstairs with 4 bedrooms and 3 bathrooms, including two master suites one with...
Kona Penthouse 2 Bedroom: Relax and Unwind Aloha Style
Top-floor Kona retreat with stunning ocean views!This 2,000 sq. ft. unit features one king-size and one queen-size bed, hosting up to 4 guests. Perfectly located near downtown Kona's restaurants, shops, and farmers market, tucked in a family-friendly neighborhood. Fully...
Steps to the beach, come share our Maui dream.
Kihei Bay Surf is a cozy 2 story complex of 80 studio condos across the street from the beach. The complex is well kept and clean, with a great pool and jacuzzi area, complete with lounge chairs, 2 barbecues and tables, tennis court, laundry room, and plenty of parking....
Hale Koolau Estate - Private Retreat in Haena with Hot Tub & AC
Hale Koolau Estate (Main House + Treehouse), Haena Permitted Vacation Rental Property - Permit ID: TVNCU #1017 and TVNC #1018Transient vacation rental is located in the tsunami evacuation zoneOn the north shore of Kauai, Hale Koolau Estate sits behind wooden gates and...
OCEAN and POOL View, remodeled 2 bdrm condo with A/C - PAPAKEA K406
Stunning Ocean and pool view Papakea 2 bedroom / 2 bathNewly remodeled throughout & new furnishings2 beautiful swimming pools, 2 ocean side cabanas, jetted spaPool side BBQs3 tennis/pickle ball courts & 2 putting greensWalking distance to stores and restaurantsShuffle...
Maui Kaanapali Villas #A102: At the heart of the Maui Ka’anapali Villas Resort,
Maui Kaanapali Villas #A102: At the heart of the Maui Ka’anapali Villas Resort, a tropical retreat awaits. This ground-floor condo has two bedrooms with en-suites and a half bathroom. The primary bedroom is just off the living area and features a king bed. The second...
Hapuna Beach Residence A32 at Mauna Kea Resort
This extraordinary, oceanfront, family-friendly, third level masterpiece offers floor-to-ceiling sliding window walls that create indoor/outdoor living space, a magnificent chefs' kitchen outfitted with professional-grade Wolf, Sub-Zero and Miele appliances, wine...
Kona Reef A1: Ocean-view 2BR condo in Kailua-Kona, perfect for 4-6 guests.
Newly renovated 2-bedroom, 2-bath ocean / beachfront condo, AC throughout home. Short walk to Kona town bars & restaurants. Snorkel, swim, or surf right in front of the condo. Enjoy the parade of activities in the ocean and on shore from the comfort of the lanai couch....
Beautiful 2 Bedroom / 2 Bath / Sleeps 6
The beautiful home is located on the east side of Oahu in Hawaii Kai. Located near beaches such as the famous Hanauma Bay, restaurants, shopping centers,hiking trails, scenic lookouts and water sports. The home offers 2 bedrooms (2 queen beds), 1 sofa bed and 2...
3BR condo with A/C, pool & 10min walk to the beach!
RENTAL CARS We also have rental cars available. Please check with us if a rental car is available for your dates. We just recently bought this beautifully decorated, spacious vacation home! Our luxurious 3 bedroom/2.5 bathroom condo is a perfect place to unwind, leave...
Oceanfront - Kanaloa at Kona - Newly Remodeled
OCEANFRONT CONDO - As Kona residents for 25 years, our desire is to share ALOHA. This is your opportunity to Experience Tropical Paradise, spectacular sunsets year-round, spouting whales in winter, and frolicking dolphins. This secluded and prestigious 18 acre Resort is...
Direct Oceanfront 2BD, Kaanapali/Kahana area, FANTASTIC! Home Away from Home!
Maui is outdoor living at its finest! Enjoy having breakfast lunch and dinner on your lanai staring at the ocean! Wake each morning to birds singing, swaying palm trees and the teal blue waters of the ocean.. there is no escaping the absolute OUTSTANDING view from this...
Oceanfront Oasis - Beachfront Condo in paradise at Sugar Beach Resort
Wake up each morning to the sights and sounds of the waves gently hitting the shore as you sit on the private lanai looking at the oceanfront view. Sugar Beach Resort is a beachfront property, no roads to cross to get to the beach, just walk out of your unit and head...
It's All About the View! Oceanfront, A/C, Elevator SPECIAL! 1/3 thru 1/5 Info ↓
2026 UPDATE: SPECIAL! The dates of 1/3 thru 1/5/26 (check-out on 1/6/26) been discounted due to late cancellation. The SPECIAL rate will be $196.00 + 18.712% + $185 one-time cleaning (approx. 30% discount). The standard nightly rate is $280.00 + 18.712% + $185.00...
Wailea Ekolu Village 1107 - 2 Bedroom Ocean View Condo
Wailea Ekolu 1107 is a charming ground-floor vacation rental that offers the perfect blend of convenience and stunning views of the ocean, mountains, and the island of Lana\'i. Guests can enjoy the soothing sounds of tropical birds without the disturbance of street...
Sweeping Ocean Views - Makena Surf Resort C-106 - Peaceful Ground Level Gem
Makena Surf C-106Nestled within the exclusive Makena community, Makena Surf Resort is a luxurious beachfront retreat offering spectacular views of the Pacific Ocean. This gated property features six carefully designed two- and three-story buildings, each strategically...
Hapuna Beach Residence B22 at Mauna Kea Resort
This spectacular, oceanfront, newly-constructed studio offers floor-to-ceiling sliding window walls that create indoor/outdoor living space, a luxe chefs' kitchen outfitted with professional-grade Wolf, Sub-Zero and Miele appliances, wine storage, plus a dining table...
Get Away to Paradise
COVID Free Quaint 3 bedroom 2 1/2 Bathroom condo located in Ko' olina Fairways. Perfect place to unwind and relax. Two story with 3 bedrooms and two full bathrooms upstairs and kitchen, living room dining room and half bath downstairs. All the comforts of home to...
Romantic 1 Bedroom Home at Anini Beach! - Sleeps 2
Retreat from the cares of the world in this tastefully furnished, one-bedroom, one-bath, oceanfront home.TVR #5082 Punana Aloha, which means 'Love Nest' in Hawaiian, is a one-bedroom, one-bath hideaway on incomparable Anini Beach. Constructed of natural cedar...
Pele's Paradise- Absolute Oceanfront Paradise with Air Conditioning!
Peaceful oceanfront paradise! Absolute oceanfront paradise on lava cliffs centrally-located between Hilo, Volcano's National Park and Pahoa. See whales (in season November-March), sea turtles and spinner dolphins right from your backyard! Fully remodeled with tasteful...
New Luxury Home in Nohea w/ Private Pool Spa and Two Ohanas
Step into refined island living with Abita Luxury Rentals at this 3,000 sq ft, 4-bedroom home built in 2023 in Nohea at Mauna Lani. Combining sophistication and comfort, this private retreat features a private pool and spa nestled among tropical landscaping along the...
Top Five Rated Vacation Rental In Pahoa, Come Relax with Us!!
Enjoy a stay in this Rainforest Hawaiian Home and experience the authentic island style living;feel the tropical breeze, inhale the fragrant scents in the air and take in the songs of the numerous tropical birds that will greet you. We invite you to experience our style...
F207 Spectacular Ocean Views - Beautifully Renovated Condo - 2 New Pools
We are pleased to announce that Makena Surf has completely renovated the South Pool! This beautiful new space is a welcome addition to the paradise we call Makena Surf!This beautiful Makena Surf condo provides the best that Maui has to offer. High end furnishings and...
Sandy Beach Front Property - Family Friendly - 4 min stroll to H2O - Ocean Views
Escape to paradise to our family friendly beach front property, Wailea Ekahi Villas unit 35B. 35B is a luxurious 2-bedroom, 3-bathroom 2 story condo (nobody above you!) and only a 4-minute walk down a gentle slope to Keawakapu Beach, a mile-long stretch of pristine...
Hilo Lagoon Retreat – 2BR w/View, A/C, Pool
Relax and Unwind at Hilo Lagoon CenterWelcome to your home away from home in the heart of Hilo! This spacious 2-bedroom, 2-bathroom condo offers comfort, convenience, and beautiful views of the peaceful waters at Wailoa River State Park.The spaceInside, you’ll find:Two...
🏖️New Listing! | Beautiful Townhome | Great Location | Concierge Included!
vrKCV - Kulalani at Mauna Lani 205 - Professionally managed by Kona Coast VacationsSecluded Kulalani Villa in the Mauna Lani ResortYour perfect vacation in a tranquil tropical oasis! Kulalani at Mauna Lani is a private gated community of quiet luxury townhomes,...
4BR Bali Inspired Luxury Home in Kukuiula
Hale Kahakai is a stunning four-bedroom luxury vacation rental in the highly desirable Kukuiula neighborhood in Poipu. Inspired by the villas in Bali, you'll admire every thoughtful detail put into this luxury home, from the latticework carved gates to vaulted ceilings...
Oceanfront Living at Luxurious Mermaid Manor in Kailua-Kona, Hawaii
Mermaid Manor – Oceanfront Island Home with Tidepools & Signature Indoor/Outdoor Mermaid ShowerWelcome to Mermaid Manor, your private oceanfront retreat in the heart of Kailua-Kona. This 2,500 sq. ft. island-style home features panoramic ocean views, three ocean-facing...
Kauai Oceanfront Condo Princeville, Pali Ke Kua 218, Best views, End unit
Beautiful Princeville Pali Ke Kua condo perched on a cliff overlooking Bali Hai, with unobstructed views of the ocean, sunsets, waterfalls, and rainbows. Turtles can be seen swimming in the cove below. December through April whales can be seen on their journey to and...
Oceanfront Tranquility at Hale Maluhia, Kona Coast
Beautiful oceanfront property featuring a private gated home with two additional separate king Bedroom Suites, each with private entrances. Enjoy unobstructed ocean views of the Pacific Ocean, Kona Coast, and Kahalu'u Beach with stunning sunsets. This property includes...
Ekahi 38-A Luxury and Grace Located in Sunny South Maui
The Quiet Luxury and Attention to Detail Will Give You the Sense That You Have Arrived Home. Our Unit is Air-conditioned With a Master Bedroom / Bath Suite That Includes a New Serta King Mattresss With 1000 Count Prima Linens, Fluffy Bath Towls for the Bath and a...
Kaanapali Alii | 322
Kaanapali Alii 3222 Bedrooms | 2 Bathrooms | Sleeps 4 | Garden View________________________________________Welcome to Kaanapali Alii 322, a one-bedroom mountain view condo with a fully enclosed den that comfortably serves as a second bedroom. This stunning residence...
6BR/6BA Luxury Villa w Pool, A/C, Walk to Beach!
Perfect for large families, wedding groups, or multigenerational getaways, this setup offers two side-by-side first-floor villas in Po‘ipu’s newest luxury complex—just a 5-minute walk to top-rated beaches and the Grand Hyatt. With 6 bedrooms, 6 full bathrooms, 2 fully...
LUXURY VILLA - 3BR/3BA with Pool & A/C - Short Walk to Beaches
Welcome to Sugar Sands Villas!Luxurious and spacious (1600+ sqft) 3 bedroom 3 full bathroom villa with central A/C (rare in Poipu), fully-stocked gourmet kitchen and folding glass doors that open to a private lanai with lush views of the Po'ipu Greenbelt. Walk to...