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.
One Bedroom Condo Across Kamaole Beach Park III
Welcome to Hale Kamaole! Nestled in South Maui, you’re just steps away from the beautiful Kamaole Beach Park III & a short drive to the Shops at Wailea. Enjoy breathtaking sunsets from your private lanai or the beach.The property features two pools, tennis courts &...
Oceanfront Center, Westin Ka'anapali, 2 bedroom, 2 bathrooms, 3/8-3/15/2025!
This 2-bedroom unit in Lahaina is perfect for your escape to paradise. This is a timeshare but is also a hotel that is managed by Marriott. Check prices with the hotel to see what a bargain this price is for our oceanfront center units. Oceanfront studios run $900+ per...
Charming NEW apartment with AC and WiFi in serene Kailua.
Brand new charming studio rental located on the owner's property in beautiful Kailua, Hawaii. Perfectly situated just moments away from stunning beaches, lush landscapes, and quaint town. This cozy retreat offers a unique blend of comfort, convenience, and island charm....
216 Waikiki Grand Hotel · 216 Waikiki Grand Hotel
Located at the Waikiki Grand Hotel & just 20ft from the world famous Hula's Bar & Lei Stand. Enjoy our comfortable studio suite, with Queen size bed, Bathtub /Shower combo and kitchenette area which includes a Microwave, minifridge, Coffee maker & Toaster. The beach...
A Marbled Suite near Waikiki, Ala Moana, McCullynn
Fully A/Ced apartment, marble floors, granite counter tops, queen size bed in each room, TV in living room, and a in-unit washer/dryer.Located in between Waikiki, Ala Moana, and UH Manoa, this is the ideal starting and ending point for every day.Less than 15 minutes...
2 Spacious Units with Private Lanais, Outdoor Swimming Pool!
Our spacious suites with private lanais offer breathtaking views of the pristine shoreline, courtyard, or garden, providing the perfect backdrop for relaxation and adventure. Stay connected with high-speed internet, unwind in our unique whale-shaped outdoor swimming...
Royal Kuhio 1708 - Spacious Corner Unit w/ Ocean City Views in Heart of Waikiki
Heart of Waikiki - Royal Kuhio (17th Floor)Address: 2240 Kuhio Ave., #1708, Honolulu, HI 968151 Bed | 1 Bath | Sleeps 4Beds: 2 Queen-size beds + 1 Queen sofa bedSize: 436 sq ft + 80 sq ft lanaiView: Partial ocean and mountain viewsKitchen: Fully equipped with oven,...
7 Nights in a 1-bedroom villa with an OCEAN VIEW April 19-26, 2025
Stroll the white sand Ka’anapali Beach, sharing the sunsets with the isles of Lana’i and Moloka’i in view. Dine in the finest restaurants or grill your own fresh fish and steaks near the pool. Take a short walk along the boardwalk to Dukes, ride to the top of...
Luxury 2-Bedroom Condo right on Waikiki beach walk. Has 2 balconies.
This luxury condo is right in the heart of the Waikiki beach & shops. The beach is a 1 minute walk away! We love the fact that it is right across the street from Ruth Chris Steak house and the Yard House, and 1 block away from the Hard Rock cafe. There is a shopping...
Kaanapali Alii | 342
Kaanapali Alii 342 is a luxurious vacation rental nestled in the heart of Maui's popular beach retreat of Kaanapali. This spacious condo offers partial ocean views from its private lanai.The interior of this well-appointed condo features a tastefully decorated living...
Ewa Beach Apartment w/ Beach Gear ~ 1 Mi to Ocean!
Embrace the island lifestyle at this 2-bedroom, 1-bath vacation rental in Ewa Beach! Just 1 mile from Puʻuloa Beach Park, this cozy apartment puts you near the surf, sand, and much more. When you're not splashing around in the turquoise ocean waters, book a tee time at...
Kolea 15C is a two bedroom penthouse with a nice open ocean view!
Enjoy unparalleled living in this spacious two-master bedroom penthouse condo, featuring stunning ocean views and panoramic mountain vistas, along with an extended floor plan that provides ample space and privacy for two couples or families.Once inside, you will be...
Tropical Elegance: Tropical Elegance, Acacia Bar, Jetted Tub & Majestic Views
Welcome to Tropical Elegance by Gather in Princeville, HI! Nestled in the heart of paradise, this 1738-square-foot townhome showcases a fusion of meticulous design and Hawaiian vibes. Designed for those who value quality, it’s the perfect blend of style, function, and...
New Listing! Ekahi 26B-*Reduced Fall Rates* | Ground-Floor Garden Oasis
New Listing! Ground-Floor Garden Oasis | 1BR/2BA Wailea Ekahi Condo | Walk to Keawakapu Beach & PoolsDiscover the perfect blend of island charm and modern comfort at Wailea Ekahi 26B. This remodeled, ground-floor condo offers a spacious 1-bedroom, 2-bathroom layout...
OAHU Resort Getaway, Beach Close, Guard Gated, Pools, Spas, Tennis, Pickle Ball!
Beautiful quiet getaway, approximately 40 minutes west of Honolulu Airport by bus or car. 1.2 miles up the hill from the famous Makaha Beach. This local area is quiet, and peaceful (except for chickens, peacocks and other local birds). Makaha Valley Plantation resort...
Maui Resort Rentals: Honua Kai – 4 Total Bedrooms, 9th Floor Stunning Deluxe Ocean and West Maui Mountain Views!
This exceptional 4BR deluxe ocean view offering that pairs two neighboring 9th-floor residences for over 2300 sq ft of combined interior living area. The suites boast spacious floor plans, luxurious finishes, and breathtaking views of the Pacific Ocean and lush West...
Kaanapali Alii | 1104
Welcome to Kaanapali Alii 1104! This two-bedroom, two-bath residence sleeps up to six guests and boasts ocean views from the lanai, living room, dining room, and primary bedroom. Entertain family and friends in comfort and style in this spacious and updated...
Cozy gateway with amazing view, close to everything. Perfect Maui stay.
Discover this welcoming 1-bedroom gem in Napili / Lahaina. This cozy condo is equipped with all the essentials for a comfortable stay, including WiFi, AC, washing machine, dryer, BBQ area, Swimming pool with lounge chairs. Guests can relax in the beautiful living space...
Relax to the Sound of Waves in This Oceanfront Studio with Beach Access
Your oceanfront tropical oasis awaits on beautiful Maui!This listing is for a room within a hotel.✦ Your room is 450 sq. ft, equipped with complimentary toiletries, TV.✦ Daily cleaning services included in the nightly price.There are a few additional details to know...
Spend Thanksgiving Week 2025 at Marriott Vacation Club - Lagoons. 2br/2b suite.n
This brilliant hotel suite in Lihue offers 2 lovely bedrooms with king beds, 2 bathrooms (hair drier , linens soaps) with a bathtub and shower, and a cozy living room with a sofa bed. Guests can enjoy amenities including outdoor pools, fitness room, outdoor grills,...
Lau'eki Estate at Hualalai Resort - Sweeping Ocean and Golf Course Views ** 2 Golf Carts**
A Sanctuary of Luxury – Lau‘eki Estates at Hualalai ResortDiscover refined Hawaiian living at its finest in this exceptional estate, nestled within the exclusive Lau‘eki Estates at the world-renowned Hualalai Resort. A perfect harmony of tranquility,...
215 Waikiki Grand Hotel · 215 Waikiki Grand Hotel
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 of the most popular bars at this end of...
Ocean View Escape, Walk to Waikiki Beach + Parking
Aloha from Midway Vacations! Our team of local hospitality experts is dedicated to turning your Hawaiian getaway into a reality. When you stay at one of our properties, you can count on a professionally cleaned and meticulously maintained experience. We're even...
Nohie Lanikai by Gather: 4BR Beachside Retreat w/ Lanai & Private Yard
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Welcome to Nohie Lanikai by Gather – A...
Shark's Cove Ocean View Deck near Pipeline 2BR
The property is in the heart of North Shore, across from Shark's Cove and the start of the bike path to Log Cabins, Pipeline, and Rocky Point. Just a few minutes bike ride to Sunset Beach or a short walk to Waimea Bay.
Royal Kahana Maui Partial Ocean View 2 Bedroom
Partial Ocean View 2 Bedroom 2 Bath- Lanai with 84-254 square feet- Open kitchen layout includes dishwasher, stove, oven, refrigerator, microwave, coffeemaker, toaster, coffee starter kit, blender, tea kettle and complimentary tea- Master bedroom with 1 king bed or 1...
DELUX family friendly accomodations in charming Princeville.
Get ready to relax in this terrific 2-bedroom condo in Princeville. This serene retreat offers a king bed, a twin bed, and two bathrooms with master bath with a jetted bathtub. Enjoy the additional living space with a cozy sofa bed. Take advantage of the fitness room,...
Westin Nanea 2 Bedroom Villa
Experience the spirit of Hawaii at our Lahaina beach resort!Travel well in Hawaii at our Maui Oceanfront resort designed with your well-being in mind. The Westin Nanea Ocean Villas, Kaanapali, is a vacation ownership beach resort located in Lahaina, once the royal...
Oceanfront Retreat! Near Waihee Coastal Dunes and Wetlands Preserve, Pool
Our spacious suites with private lanais offer breathtaking views of the pristine shoreline, courtyard, or garden, providing the perfect backdrop for relaxation and adventure. Stay connected with high-speed internet, unwind in our unique whale-shaped outdoor swimming...
Extraordinary - Kona Sea Ridge Condo Big Island
About this spaceLuxury comfort with stunning views. A perfect island getaway, centrally located to explore the Island.The spaceTropical gated community 1 mile from central Kona Town. Fully remodeled unit with high end modern furnishings. Designed for those with...
Relaxing dog-friendly home near beaches, private W/D and shared pool
Manawa Ho'omaha | 31-Day MinimumOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Escape to paradise with this charming house that has everything you need for a wonderful month-long...
Wailea Ekahi Village | 12B
Wailea Ekahi Village 12B is a beautiful vacation rental that underwent a complete update in March 2021. Interior designers may want to take notes! This gorgeous ocean view studio is ideal for couples looking for a cozy retreat or solo travelers looking for the perfect...
Sands of Kahana fantastic two bedroom villa
Concierge Realty is proud to present luxury villas at Sands of Kahana.**Reservations are available in weekly (7 night) increments with arrivals and departures on Fridays, Saturdays, and Sundays only.Please note: Please be aware that air conditioning is not available in...
Please inquire about 2025 booking requests
Please inquire about 2025 bookings in the Ocean Front Deluxe Unit. Best view at the Westin KOR and directly facing/across from the ocean. Please inquire with any questions.RESERVATIONS AVAILABLE IN SEVEN NIGHT INCREMENTS ONLY WITH CHECK-INS ON FRIDAYS, SATURDAYS or...
Beachfront Room w/ Expansive Ocean Views, Full Private Lanai, & Special Gift
With an exclusive location on the 10th floor and above, each room provides a full private lanai with expansive views of Waikiki Beach and the Pacific. Guests also receive a special gift of Hawaii-made treats personally picked by the hotel’s general manager. Air...
Royal Kahana Maui 310 Oceanfront 2 BD/2.5 BA
- 3rd floor condo with wrap around 254 square feet balcony- Updated open kitchen with granite counters, kitchen island includes stove, oven, refrigerator, microwave, coffeemaker, toaster, coffee starter kit, blender, tea kettle and complimentary tea- Tiled entry,...
Honua Kai Luana Garden Villa 3A 3 Bedroom 3 Bath
Unit #3A Luana Garden Villa 3 Bedroom 3 Bath Garden Villa- Open kitchen concept – Bosch appliances to include induction cooktop, wall oven, counter-depth French Door refrigerator with two freezer drawers, quartz countertops with full height ceramic tile backsplash,...
Wailea Point 3 Bedroom/3+ Bath Oceanview Condominium #2503
Yes, you can enjoy a holiday and vacation stay at Wailea Point, the iconic red roofs on Maui's wonderful southern shore; and at a rate lower than a suite at the Wailea hotels. 2503 just may be the 'best location in the whole property'; with an expansive outdoor lanai...
Beachy Kona Getaway. Located within walking distance to the heart of Kona Town.
Welcome to our dreamy Kona getaway! This newly refurbished, luxury beachy retreat is designed for relaxation and convenience in the heart of Kailua Kona. Walking distance from Kona's best restaurants and bars, it provides easy access to Ali'i Drive and all it offers,...
Marriott's Waikoloa Ocean Club | One-Bedroom Villa
Summary:Experience the lush beauty of Hawaii's big island at Marriott's Waikoloa Ocean Club Resort. Located on the pristine sands of the Waikoloa Beach, this resort is what dreams are made of! Enjoy a day at the resort swimming in the pool, playing at the beach, booking...
PLEASE MESSAGE US, THE CALENDAR IS NOT UPDATED
A Stunning Estate On a Verdant Hillside is Simply Like No Other. This Home Is Located in the Famed Neighborhood Where Hawaii 5-0 was filmed.This Property is Secluded With a Soothing Contemporary Ambiance of Hawaii That Brings Comfort and Relaxation to All Visitors....
Kapalua Ridge Villa 2215 Ocean View 1 Bedroom
- 1st floor villa with two stories overlooking Oneloa beach- Stairs between parking and front door- Interior stairs to access Master bedroom- Tile in kitchen, bathrooms and dining room with bedroom carpeted- Granite counters and stainless steel appliances includes...
Waipouli Beach Resort Studio
Studio- Condo includes microwave, mini refrigerator and coffee maker- 1 king bed- 395 sqft/37 sqm- Maximum 2 persons including children and infants- Lanai/Balcony- Walk in shower- Central air conditioning- Flat panel 37-inch TV with standard cable- Wired high-speed...
🏖️Fully Air-Conditioned | Updated Top Floor Incl Loft | Ocean Views | vrKCV
vrKCV - Country Club Villas 327, Professionally Managed by Kona Coast VacationsCountry Club Villas 327 – Ocean & Golf Course Paradise in KeauhouExperience the beauty of island life at Country Club Villas 327! This newly renovated (2024) 2-bedroom plus loft condo is...
Wonderful 3 bedroom for 6 ocean view Kekaha home!
Listing provided by "The Vacation Rental Experts". Contact directly for more options!This very popular 3 bedroom, 2 bath direct ocean view Kekaha home, is just steps to the beach in front of the home, with famous Kekaha Beach park just 3 blocks away! Just 1 mile to the...
Hale Kai - Brand New Kukui'ula Luxury Home with Pool & Spa
Nestled in the exclusive Kukui'ula neighborhood in Poipu, this stunning, brand new luxury home offers the perfect blend of comfort, elegance, and island charm. With 4 bedrooms and 4.5 bathrooms, this meticulously designed residence comfortably accommodates up to 12...
Tranquil Panoramic Retreat: Embrace Romance in Peaceful Serenity
This cottage is solely for couples who are in need of relaxation and peace. It is a cozy two-bedroom one-bath cottage, conveniently located on the ground floor for easy accessibility to our BBQ area along with a lanai capturing breathtaking sunsets of our West-Central...
Bamboo Bliss: Ocean Views & Waterfalls Await!
**Escape to Thai Hale at Maui Eco Retreat – Your Haven of Bamboo Bliss and Ocean Views**Immerse yourself in the unparalleled tranquility of Maui Eco Retreat, where the rhythm of nature sets the pace for your rejuvenation. Thai Hale offers an idyllic retreat that...
❤ Spectacular Full Ocean View - Beachfront - Oceanfront - Hono Kai C3 ❤
There are spectacular unobstructed views of the ocean and Haleakala with floor to ceiling windows from inside the condo and on the lanai! You simply can't get closer to the beach or ocean! Perfect for whale watching! Steps away from the ocean, equipped with a fully...
*New* Hale Halai - Pool, AC, Close to Beach
Welcome to your spacious retreat! This expansive 5000 square foot home boasts an inviting open floor plan, perfect for bringing families, friends, or colleagues together for a memorable getaway. With 7 bedrooms, 5 bathrooms, and the comfort of air conditioning, everyone...