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.
Breathtaking, FRONT ROW seat to the azure Pacific
Maui's best kept oceanfront secret, this adorable one bedroom, one bathroom unit is sure to please! Bluish hues throughout the condo bring an instant calming effect as you enjoy the comforts of home. This condo is breezy and relaxing. Your fully equipped, upgraded and...
Hawaiian plantation-style home - fenced yard, ideal for families.
On Kauai's north shore in the charming town of Hanalei, this Hawaiian plantation-style home is very comfortable and has a fenced yard that is ideal for families. Its location across the street from a beach access path makes it a very short walk to the beach at...
KBM Resorts | FREE CAR | Honua Kai Konea | 2-Bedroom Condo with Huge Lanai, Easy Pool & Beach Access! HKK-113
XL lanai ground floor villa, spacious 2-bedroom, great for families! best pool & beach access! beach gear provided, L'Occitane amenities** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6...
Kona Sea Ridge L-4 - Townhome in the heart of Kona
Kona Sea Ridge is a quiet gated community nestled in between Alii Drive and Kuakini Highway. Located right in town and close to Historic Kailua Village, the complex is protected from the hustle and bustle and noise of daily traffic. Kona Sea Ridge unit L-4 is located...
Stunning home with multiple lanais, private gym, lush green space & fruit trees
Ke Kai OlinaOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Nestled in the heart of Princeville, Hawaii, this stunning 6-bedroom house is a true tropical paradise. Surrounded by lush...
Across The Street From The Best White Sand Beach In The Area!
This upgraded condo is the largest in the complex with a wrap around lanai with a beautiful garden/Mountain View with 3 sliders going out to the lanai from the dining room, living room and master bedroom. Recently upgraded with granite countertops in the kitchen and...
Ko Olina Beach Villas 706: 2BR Villa w/ Panoramic Ocean View
Welcome to Ko Olina Beach Villas B706 by Gather, a magnificent beachfront villa located in the prestigious Ko Olina Resort Beach Tower. This exquisite seventh floor two-bedroom, two-bathroom vacation rental, with space for up to four guests, offers an unparalleled...
𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢 Beach Fun at Waiohai Club +Resort Amenities. 2-Bedroom
Welcome to 𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢! 🌺 Escape to Paradise: Your Dream Vacation Awaits at Marriott Waiohai Beach Club 🌺An Additional Savings from $500-$1000 (approx) can be provided on certain 7-Night stays for 𝐅𝐢𝐧𝐝𝐢𝐧𝐠...
Ocean View Poipu Beach Condo (A/C) 804
Commanding View of the Sunny Poipu Oceanscape, where luxury & lush surroundings await you at our Poipu Beach Condo!Spectacular Ocean View, 2-story, non-smoking condominium, has over 1200 interior sq. ft. as well as 3 private lanais. It's perfect for one family, or 2...
Tastefully upgraded. One of the only resort units with a full size laundry team.
Enjoy your home away from home in our consistently updated unit at the Maui Hill Resort, located in Kihei. A quick walk to beach and a short drive to either Wailea or the amenities of Kihei. Very spacious, our unit has many updated features, including an expansive lanai...
DIRECT BEACHFRONT Condo at Sugar Beach Resort
Unit 115 comfortably sleeps 4 - King size bed in bedroom and queen hide abed in living room. TV is located in the living room . Fully furnished unit including beach towels and beach chairs. Views of Haleakala and West Maui Mountains from your lanai - amazing sunsets...
Watch sunsets from this Oceanfront Condo beside the beach!!
Beautiful unobstructed view of the ocean and Kamaole I Beach! Watch whales, turtles and the sunset every day on the lanai with your favorite beverages and pupus (appetizers). Calving whales and the graceful Hihimanu (Hawaiian spotted eagle) rays have also been observed...
2 king bed, 2 bath in-suite washer & dryer. Amazing view!
This professionally decorated two-king-bed, two-bath condo is everything you could hope for and more in a vacation retreat. Recent renovations completed kitchen upgrades in 2020. The last two years also saw the addition of new furniture and finishes. The oceanfront...
Hale Aina ~ Home of the Land
Spacious 1-Bedroom, 2-Bath Plus Loft at Ku'ilima Estates – Short distance to The Ritz-Carlton at Turtle BayExperience island living at its finest in this contemporary, art-filled 1-bedroom, 2-bathroom loft unit at Ku'ilima Estates, located just minutes from the...
Luxurious 2BR Beachfront Waipouli Resort, AC, Wifi, Steps to Beach
Waipouli Beach Resort #B301, Named Hawaii's #1 Resort** Waipouli, Kaua'i , East Shore of Kaua'i. Accommodates up to 6 guests, including children and infants.Conveniently located on the Coconut Coast, Wailua, walk to shops, restaurants, beaches and more! This central...
Poipu Sands at Poipu Kai #514 By Parrish Kauai Oceanfront Views
Our luxurious Kauai vacation rentals at Poipu Sands offer spacious layouts, large covered lanais, a private heated resort swimming pool, community gas BBQs, on-site tennis courts, and more.Centrally located in Poipu, adjacent to the Grand Hyatt Resort & Spa as well as...
Luxurious Maui Living at Palms 203
Experience luxurious Maui living at its finest in this exquisitely remodeled 2-bedroom, 2-bathroom condo at the prestigious Palms at Wailea. This stunning vacation retreat seamlessly blends modern, chic design with island comfort, featuring a bright, open-concept living...
Unobstructed Diamond Head and Ocean Views!
Waikiki Banyan #3511-T1 – 201 Ohua Ave.Unobstructed panoramic views of Diamond Head, the Pacific Ocean, and the Gold Coast from this 35th floor unit! Modern and contemporary, this air-conditioned condo has tasteful Hawaiian touches, 533 sq.ft. plus lanai with table...
Turtle Bay Hale Lani - Kuilima Estates East
This beautiful, modern 1 bedroom w/loft bath and a half. Upgraded unit has new kitchen cabinets & appliances, ceramic tile floors and granite countertops. The extended living room has a large flat-screen TV, internet and WIFI, TV in master bedroom as well. Window a/c in...
GORGEOUS OCEANFRONT CONDO W/AMAZING VIEWS - Waipouli A204
A204 is a prime Royal Oceanfront unit with gorgeous ocean views from every window. Sleep to the sounds of the waves right out your bedroom window. Prepare meals in the state of the art kitchen, featuring a large Sub-Zero refrigerator, Wolf glass cooktop, GE Profile...
Chic Waikoloa Condo w/ Lanai + Complex Pools!
Island breezes and sun-soaked palm trees set the scene at this stylish Waikoloa condo. The 2-bedroom, 2-bathroom vacation rental has everything needed and beyond for a memorable trip, including a furnished lanai, open layout, full kitchen, and access to complex...
Waikomo Stream Villas 530, AC, 2 bed/2 bath, Club Access
WAIKOMO STREAMS 530 AT KOLOA KAI VACATION RENTALSA Tranquil Retreat in PoipuImmerse yourself in the natural beauty of Poipu at Waikomo Stream Villas 530. This third-floor condo overlooks lush greenery, vibrant flowers, and the serene Waikomo Stream, offering a peaceful...
Ocean View Upgraded Waikiki Banyan
Summary:Unit Summary:Waikiki Banyan (Tower 1) 34th Floor offers unobstructed Diamond Head and Ocean views! Also overlooking Kapiolani Park. This is a clean and comfortable furnished unit.Tower 1 and the views from the 34th floor makes this one of the best and preferred...
Romantic Beachfront Getaway
Your beachfront escape awaits... This is the perfect spot for your romantic getaway! Right on the beach, you'll enjoy days in the sun, romantic meals dining on the private garden lanai with views of the azure Pacific and nights falling asleep in the luxurious canopy bed...
Hot Deal! Turtle Bay Villas 307 by Gather: Beachfront w/ Shared Pool, Spa, AC
Please note: Access to resort amenities is not included, however, the condo complex has its own pool, grills and is just steps to the beach!Experience the ultimate Hawaiian getaway at Turtle Bay Villas by Gather. Whether you are looking for a romantic couples getaway or...
Hale La'i: Dreamy Kona Oceanview Estate with Pool, Spa & AC
Aloha & Welcome to Hale La’i - House of Peace and TranquilityFor years, visitors from around the world have traveled in search of a tropical destination offering a relaxing transcendent experience. Our family has found that here, on the Big Island of Hawaii. We have...
Sugar Beach 206 Highly Upgraded Condo Home with Amazing Ocean Views
Book with us and come to Maui to explore everything we have to offer!Welcome to your remodeled air-conditioned condo beach home. Enjoy the upgraded kitchen, bathroom, and living room. The lanai will allow you to take in the amazing views of the Pacific Ocean as you...
Hale Kai | Ko Olina | Villa w/ Ocean Views!
Summary:Welcome to Hale Kai 2 in Ko Olina! Immerse yourself in this coastal getaway, where colorful landscaping and shimmering lagoon pools await. Maximum occupancy strictly enforced in accordance with local ordinances.The Space:Whether you're unwinding in the steamy...
Entire 3bedrooms Apt. w/ Balcony & Ocean Sunset View, Great Location
Welcome to MaiLan Hale, Located in the heart of historic Kailua-Kona Village, This is a completely fenced-in, private 3-bedroom, 1 bathroom unit, accessed by a gate-code for the fence and key-code for the rental unit. Take in the fresh Hawaiian air, enjoy the warm Kona...
Kahala at Poipu Kai
1 bedroom, 1 bath condo with beautiful ocean views. Fully furnished kitchen. Washer and dryer, air conditioning in the bedroom. Master suite with king sized bed. Family room boasts vaulted ceilings. Bonus sleeping area in the loft above the family room. Swim in the...
Whale and Turtle Watch 25% off Sale into 2025 with Fantastic Oceanfront Views.
Unit C-22 at Napili Point Resort is a top floor, 2 bedroom, 2 bath oceanfront condo offering fantastic unobstructed ocean views of the West Maui ocean and the islands of Molokai and Lana'i. Currently running 2025 Regular Season Sale of up to 25% off ($375 night) except...
Maui Kaanapali Villas 292 60%Off April & May Deals at Remodel OceanFront Retreat
The Stice Team — Powered by Gather Vacations. Maui Born and Raised Professionals. Your Local Experts in Crafting Unforgettable Stays.Welcome to Maui Kaanapali Villas 292, a beautifully remodeled top-floor condo where up to six guests can enjoy the perfect balance of...
Remodeled 1bd villa with ocean views
Kapalua Bay Villa 29G4 is a newly remodeled 1-bedroom, 1-bathroom villa that can accommodate up to 4 guests comfortably with privacy as well as panoramic views. The private lanai is the perfect spot to wind down with a beverage and take in those surreal Maui sunsets....
Home near the beaches w/ washer/dryer, central AC, shared pool, hot tub, tennis
Hale PoluOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Set in one of the best locations in all of Poipu, and with access to the Poipu Kai Association tennis courts, heated pool,...
🏖️Private Pool | Central AC | Concerige Included | Resort Access | vrKCV🏖️
vrKCV - Wai'ula'ula 334 at Mauna Kea, Professionally Managed by Kona Coast VacationsExperience Luxury at Wai'ula'ula Villa 334Aloha and welcome to your villa in paradise! Nestled in the exclusive gated community of Wai'ula'ula at Mauna Kea, Villa 334 offers breathtaking...
Kona Isle E-24 Direct Ocean front coner unit 2nd Floor,Sleeps 4, Spectacular
E-24 at the Kona Isle is a high in demand Direct Oceanfront Corner End Unit on the 2nd Floor of Building E. This gorgeous condominium has jaw dropping ocean & sunset views from your Lanai. Enjoy amazing ocean breezes that flow through this property on a consistent...
Pineapple Cottage surrounded by coffee plantations
This cozy Holualoa studio offers comfortable accommodations, up-to-date amenities, and a private deck that overlooks the small Kona Coffee farm that resides on the property! While relaxing, relish the lush gardens, sounds of the local wildlife, and ocean views. When...
Pacific Monarch Top Floor Condo with Ocean, Diamond Head and Mountain Views!
Step into your own slice of paradise in this beautifully appointed 23rd-floor retreat at Pacific Monarch. Designed for those who crave both luxury and the relaxed spirit of island living, this one-bedroom escape offers a serene atmosphere with stunning views of...
WOW!! CORNER UNIT- Ocean View located in the heart of Kaanapali H108
Enjoy ocean and Kaanapali Golf course views at this prime ground floor location at the Maui El Dorado, Unit H108. Double length lanai extends from spacious living room to master bedroom opening up to a large grassy area. This 1700 sq ft luxury Maui vacation rental has...
Waikoloa Beach Villas E33 - Luxury Private Top Floor Villa and BBQ on Lanai!!
This beautiful 2 bedroom, 2 bath villa has everything you need for a great vacation on The Big Island of Hawaii. Master bedroom has a king bed and on suite bath. Guest bedroom has 2 full size beds. NEWLY remodeled guest bathroom with a walk-in shower. Kitchen is fully...
Beachfront Paradise with A/C - Sugar Beach Resort #227 - Stunning Ocean Views!
Welcome to Sugar Beach Resort #227– Your Beachfront ParadiseExperience the serene beauty of North Kihei at Sugar Beach Resort, a picturesque beachfront condominium resort offering breathtaking Pacific Ocean views. Two six-story buildings, equipped with elevators,...
Maui Sunset B222 Upgraded 2 BR Oceanfront Condo Large lanai
Maui Sunset is the perfect vacation home on Maui. Your island days can be filled with recreation and fun. Swim in Maui Sunset¹s beautiful pool with a shallow end for small children or enjoy relaxing in the jet spa. This lovely resort also offers:Swimming pool, hot spa...
3BR, 3BA Kailua-Kona Condo. Best location. Beautiful ocean & golf course views!
This Keauhou Punahele Condo is in the best location in Kona. This lush tropical property is set in the Keauhou Bay area and features everything you want and need. A-303 is a remodeled upscale condo overlooking the 8th hole of the Kona Country Club Ocean Course in the...
Lae Nani 338 Oceanview with AC a "Coconut Coast Beauty"
"Coconut Coast Beauty" at Lae Nani 338 With ACOceanview Third Floor Lae Nani Condo | 1 Bedroom | 1.5 Bathroom A restful coastal vibe awaits in Lae Nani 338. This newly remodeled condo with AC sits on lush tropical grounds just steps from the ocean. With ocean views from...
Renovated Adjoining Waikiki Studios w/2 Full Baths, Kitchen and Ocean View
The condo is centrally located within walking distance to the beach, shopping and restaurants. Walk to the beach, convention center, mall, shops, restaurants, and other Waikiki attractions from this spacious and newly renovated condo. The condo consists of two adjoining...
Beautifully appointed ground-floor Kaanapali condo
Kaanapali Shores 104 is a ground-floor, 2-bedroom, 2-bathroom condo with central air conditioning that can accommodate up to 6 guests. Ocean views abound and the beach is only 50 steps from your lanai. Inside, an open-concept layout and Hawaiian-inspired decor with a...
SALE Mon - Fri! nOceanfront Sea Breeze Studio with Fantastic View and Location
Welcome to our ocean view studio! Our relaxing, bright and cheery studio condo offers you a comfortable king size bed and fully equipped kitchen for those days you may want to cook in. Wake up to the ocean breeze, the sound of waves and the gorgeous Maui sun. Our large...
Delightful Oceanfront Island Gem w/ Views, Shared Pool, Beach Access, Free WiFi
Wailea Ekahi Village 5COur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Are you ready for those dreamy island sunsets, Pina Coladas, and sun-kissed skin? Well, this wonderful retreat...
Direct Oceanfront Condo! Sea Turtles & Beautiful Sunsets from the Lanai
If you’re seeking the tropical getaway of a lifetime, look no further than this amazing oceanfront Kailua-Kona vacation rental condo, complete with mesmerizing sunset views over the Pacific! With 1 bedroom, 1 bathroom this unit is the perfect size for a couple out for...
Aloha Condos, Kona Coast Resort, Condo 5-102, Fairway Front, AC
Welcome to our "piece of paradise!" Our extremely comfortable unit is located in the quietest building in the Kona Coast Resort and looks out on to the 16th Fairway of Kona Country Club. Our updated 1 bedroom/1 bath condo is very spacious with 1453 square feet and the...