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.
Kauai -Anahola Beach Front
NA PAINA is a spacious 2-story cedar house nestled in ironwood trees right on the sandy beach at Anahola Bay. This classic old-school beach house has two decks and spectacular ocean views. Anahola is a secluded bay, located in a small residential community and has a...
Chic Condo Near Waikiki Beach - Free 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...
Charming condo with amazing ocean vistas, full kitchen, W/D & sunrise-view lanai
Sealodge at Princeville J3Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'It’s all about the spectacular views at this cozy and relaxed single-level Princeville condo! Begin your...
Stunning Estate Property In Gated Community Steps From The Ocean
Welcome to our 5 star rated vacation home. We call our home Forever Sunsets because with just a short walk to the water in our gated community you can watch the sunset every night. You are also a short 600 yard walk to Magic Sands Beach, the most popular sandy beach in...
Beaches, Beaches, Beaches! West Molokai. Remote and Private. Hawaii's best.
Kepuhi Beach Resort Condo. Corner ground floor 1 BR. Living and Bedroom both face the awesome blue ocean view which is backdrop to the 11 acre green grounds full of mesmerizing swaying palm trees. 800' to water’s edge on Kepuhi Beach. Short 1/2 mi. walk to famed...
SPECIAL DEALS Honua Kai 8th Flr Remodeled Suite in Paradise ONE-OF-A-KIND
🌴 West Maui is Open – and Honua Kai is Resort-Zoned. 🌴Book with confidence knowing you’re safe from the recent legislation impacting other short-term rentals.🍍 Welcome to Konea 830 at Honua Kai – A Modern Mountain-View Retreat 🍍 Step into The Beach House-Styled Suite, a...
Pipeline Beachfront House - Sleeps 12 Guests
Minimum 30-day consecutive rental required. Please contact the Host for availability. Located right on the beach where dreams are made for many professional surfers every winter. This three-story house has four bedrooms and four and a half baths. Enjoy amazing ocean...
Breathtaking 3rd-floor 3bd oceanfront condo
Stunning oceanfront views with Molokai and Lanai as your backdrop. Noelani 302 is a spacious 3-bedroom, 2.5 bath condo that is perfect for families and groups. It offers a fully equipped kitchen including dining space inside and outside on the private lanai. This unit...
Private ground floor villa with bbq and golf course view.
Waikoloa Beach Villas K2, is excited to be on the vacation rental market. Updated design with new appliances gives this first class home the edge and excitement to enjoy your vacation in paradise. 2 bedroom, 2 bathroom with full size kitchen to provide you with the...
Maui Sunset A307 Fabulous Oceanfront Complex Featuring Magnificent Sunset Views
Recently renovated in July of 2024, featuring new cabinets, vanities, countertops, appliances, fixtures, doors and painted throughout. Spend your vacation on the beach, at the beautiful Maui Sunset complex, where our lovely, one bedroom condo is located. Take a relaxing...
Paradise Retreat, POOL, Hot Tub and AC with ECO energy!
Paradise Retreat is your own private resort on Hawai'i’s Big Island. Relax and enjoy the swimming pool and hot tub in our private, fully enclosed back yard. Lounge poolside in the sun-soaked chaise chairs or stay cool on the covered lanai. In the evenings, enjoy starry...
Bamboo Valley Inn 2BR/1BA Permitted
Maui County Bed and Breakfast Permit #BBPH 20090014,TA-200-805-1712-02 Make sure you check as most rentals do not have permits from Maui County to operate and may be shut down. If you are looking for peaceful Hawaii away from the crowded resorts and neighborhoods, look...
Ocean Front with stunning views! Includes beach gear! Halii Kai 15H
This vacation rental is professionally managed by ResorticaHawaiiNew Furnishings and new paint in 2025!Halii Kai 15HPlease scroll down for detailed informationBedding Configuration:Master Bedroom: King BedGuest Bedroom: Queen BedGuest Bedroom: 2 Twin BedsLiving Room: ...
Vacation In Paradise At Makaha Area in a Legal NUC
Come to Paradise on Earth at the Hawaiian Princess located in the dry, sunny Makaha Area in West Oahu. The condo is on a secluded 1/3 mile pristine white sand beach overlooking the gorgeous Turtle Cove. Celebrate a special occasion, romantic getaway or just come to...
The Best of Kamilo, Mauna Lani - Largest Model Home, Guest House, Pool, Spa!
Kamilo 331 is a resort home offering 4 luxurious bedrooms and a private solar heated pool and waterfall spa. Kamilo 331 is one of the few Hoku B floor plan models, the largest and highest-priced home available in the Kamilo community. This single-level family home...
Oceanfront stunning corner condo
You'll enjoy Papakea Resort A101-A102's amazing oceanfront location and the beauty of Maui from virtually every room! This lovely and unique 2-unit corner property was converted into one large 2-bedroom, 2-bathroom condo with over 1,300 square feet and a split air...
Wailea Ekolu 703 / Beautiful Ground Floor, Expansive Lanai, Ocean Views & Aircon
Indoor outdoor living with Fantastic Ocean views from this spacious 2 bed/ 2 bath ground floor private condo! Enjoy early morning walks or a relaxing dip in the pool. This unit has been completely remodeled from top to bottom, all new windows and double pane sliding...
Hard To Beat Oceanview 2Br/2Ba - Newly Renovated - Saltwater Pools & Pickleball!
CANCELLATION IS POSSIBLE!! See standard cancellation terms outlined in our Rental Agreement. We are also willing to work with our guests to make their vacation possible, especially with Covid issues and potential travel restrictions.You’re invited to stay in our Kihei...
TOP FLOOR CORNER PRIVATE STUDIO, AFFORDABLE WAILEA, WALK TO BEACH
Last minute DISCOUNTED RATES We appreciate your support as a small, self managed Maui family owned rental instead of renting from a large mainland management company. Enjoy sunny South Maui in our lovely studio top floor condo at the award-winning Grand Champions...
Two-Story Private Home at Kamilo - Grill Deck, Pool & Sunset Views!
Beautiful private home with a heated pool, spa and 2,400 square ft. of interior living space in a prime resort location. This 2-story dream home overlooks the famous Mauna Lani golf fairways and features vaulted ceilings, exotic hardwood floors, emerald granite counter...
🏖️Ocean Front | Central AC | Private Pool | Concierge Included | vrKCV
vrKCV - Holua Kai 21, Professionally Managed by Kona Coast VacationsThis stunning oceanfront home is situated in Kona on the Big Island, offering breathtaking, unobstructed 180-degree ocean views and the best of island living. Overlooking the second, third, and fourth...
*A/C* Elegant Single Story ~ Plantation Home
Absolutely Beautiful Inside & Out... Plus New Air Conditioning :) This Tropical Plantation Home offers 4 Bedrooms. It is Elegant & Richly Appointed with Rare Solid Hawaiian Koa Wood Flooring and a Spacious Floor Plan. The Sliding Glass Doors Surround the Living Room and...
Tropical Luxury Villa: Indoor-Outdoor Living, Gourmet Kitchen & Spa Bathrooms!
Special Luxury Promotion Book 7 Nights and Enjoy the 8th Night FreeIndulge in the ultimate getaway at our luxury residence and extend your stay on us. Reserve seven consecutive nights and receive the eighth night completely free, the perfect way to elevate your vacation...
Spacious Wailea Townhouse + Ocean Views! Ekahi 48A
Welcome to Wailea Ekahi 48A, offering the largest floor plan with gorgeous ocean view! This beautiful 2 bedroom/2.5 bath is the perfect retreat for couples or families. The first level of this spacious condo features a sunken living room complete with convertible queen...
Maui Resort Rentals: Groundfloor Interior Honua Kai Konea 143, Huge Lawn Area, Steps to Pools/Beach/B.B.Q.s!
Enjoy one of the most convenient ground floor locations at Honua Kai in the highly sought interior courtyard of the Konea Tower. Konea 143 offers a spacious 1315 square feet of living space and convenient interior ground floor access to the pools, beach, and BBQs. The...
Breathtaking Oceanfront Condo Kauai Vacation Rental
PU'U POA 305 is a beautiful two bedroom condo with unobstructed views of the ocean. Every morning you can drink your coffee and have breakfast watching the surfers catch the ever changing waves at the point by the St Regis Hotel. On many days in the winter and spring...
Four Bedroom Luxury Home - Ka Milo at the Mauna Lani
Located in Ka Milo at the Mauna Lani Resort area, our luxury home boasts 4 bedrooms, 3.5 bathrooms, a full kitchen stocked with essential equipment, a laundry room with a washer and dryer set, and a lanai deck with an ocean view. It comfortably sleeps up to ten adults...
Spacious Kealakekua Bay Home with 4-bedroom bay home: Enjoy Quiet rejuvenation
Hale Maluhia La‘a' - Home of Sacred PeaceReview all 99% of our wonderful 5 Star reviews on our homePlease contact the owner with any questions, and about 6 month or longer rentals. 25% discount on 28 day stays.This is our beautiful 4-bdrm; 4th bdrm/Great Room home It's...
Nicely upgraded 2nd-floor 1bd ocean view condo
Papakea G204 is a 1-bedroom, 1-bathroom condo situated on the 2nd floor, and can accommodate up to 4 guests. Papakea Resort has elevators for easy access to your condo in paradise. This condo offers a fully equipped kitchen, perfect for dining in. The living room area...
Best location Long term rentals available
HI SPEED WI FI FIBER OPTIC INTERNET THAT RUNS @ 1GB SPEED.FREE FIBER OPTIC INTERNETOR DIRECT ETHERNET CONNECTION IF PREFERRED This perfect central location is ideal for exploring the entire Island. Aina Lani can be your home base for day trips anywhere and the best...
Home Of The Cherished Seacoast By Parrish Kauai- oceanfront & walk to Poipu Beac
Our Kauai cottages include this one across from the world famous Brennecke Beach and steps from sunny Poipu Beach. Hale Kahakai Punahele (The House of the Cherished Seacoast) is arguably located in one of the best beach locations in Poipu. With its incredible...
OCEANFRONT condo with spectacular views, close to all - Maui Kai 908
Discover your Maui sanctuary at this completely remodeled 1-bedroom, 1-bath oceanfront condo at the Maui Kai Resort, located directly on North Kaanapali Beach. With breathtaking 180° views of Lanai and Molokai, stylish interiors, and updated finishes throughout, this is...
West Maui, Oceanfront:April 2 - 11 on Special!
Beautiful MAUI condo with unrivaled views of the ocean, the islands of Lanai and Molokai! Imagine being in this Top Floor Unit directly on the ocean, as you enjoy your meals & those spectacular complimentary sunsets from the lanai. Nestled 10 minutes north of Lahaina,...
Hale Moana E21, Coconut Grove Views, Walk to Kapaa Town and Beach
Village Manor Apartment #E21. Waipouli, Kapa'a, Kaua'i Vacation Rental. Accommodates up to 4 guests, including children and infants.Hale Moana in Village Manor #E21 is a cozy, bright and airy second floor, two-bedroom, 1.5 bath, end unit with mountain views and distant...
White Sands Village#325: Incredible Wrap Around Lanai,Beachfront Complex, AC!
Penthouse Style Living, Spacious 1030 sq ft condo located in White Sands Village Kona's Premier Vacation Rental destination. Private, peaceful corner unit with 416 sq ft wrap around Lanai, top floor with 2 bedrooms & 2 bath nicely appointed, sleeps 6. Master has a...
Haena Beachfront With Stunning Panoramic Ocean Views TVNC # 5134
Anchorage Point offers a once-in-a-lifetime vacation experience, providing contemporary luxury in a secluded beachfront setting. Ideal for families, the home showcases breathtaking panoramic views of the Pacific from its living spaces and from both master suites. It is...
Unbelievable Ocean Views and lovely Kailua Bay.
The view is of the entire bay and harbor of Kailua-Kona. This is a remodeled 2 bed, 2 bath, washer/dryer, reserved parking on ocean condo. We have put in a built-in desk with WIFI connections should you need to work remotely. Our pool is salt water and heated in the...
View, Views, Views, Studio King Bed Views of Hanalei Bay, Lagoon pool from condo
Please note $45/day Resort fee and $50 check in fee not include in VRBO total and paid by guest upon check in arrival.#1303 has views from the highest point at Hanalei Bay Resort of Mt. Namolokama and its spectacular waterfalls, Hanalei Bay, lava rock pool and hot tub,...
Maui Resort Rentals: Honua Kai Konea 407, Upgraded Interior Courtyard 2BR w/ Full Ocean Views
Konea 407 is a gorgeous oversized 1315 sq ft 2 bedroom OCEAN VIEW villa with 3 KING BEDS that affords а perfect opportunity for a GROUP OF 8 to gather and celebrate or just have a relaxing time! Its 4th-floor location offers beautiful ocean and pool views. This prime...
LOW MAY RATES Just across the street to the beach ! Read our EXCELLENT Reviews!
LOVELY and remodeled condo # 108 at Kihei Resort ! BRAND NEW KITCHEN REMODEL , New laminate FLOORS, New furniture, KING BED BRAND NEW, New Italian Queen sofa sleeper with foam mattress . Sleep well in your Luxrious Jade Euro Top Hybrid which is Individually Encased...
Villa Maluhia with AC, views!, watch baby albatross play in your front yard
Welcome to Villa Maluhia, a fully renovated 1br/1ba nestled in the serene beauty of Hawaii’s Garden Isle. Situated in the prestigious Kamahana Princeville community, this downstairs unit offers panoramic ocean views and golf course views at the end of a quiet road where...
Maui Resort Rentals: Honua Kai Hokulani 736 – 7th Floor Ocean & Mountain Views w/ King Size Balcony!
Hokulani 736 is a luxurious 7th-floor two-bedroom ocean view corner suite and one of the few offerings at Honua Kai that affords views of both scenes that Maui is famous for... the relaxing blue Pacific Ocean and the majestic West Maui Mountains.The generous 1240 sq ft...
Golf Villa with Ocean View! Reduced Rates & Green Fees!
Come and discover tropical paradise in this tastefully remodeled golf villa. Located on the sun-drenched Kohala Coast between two beautiful golf courses it provides spacious vacation accommodations with easy access to some of the Big Island's most notable...
🏖️Private | Golf Front Townhome| Concierge Included | vrKCV
vrKCV - Mauna Lani Fairways 1104, Professionally Managed by Kona Coast VacationsRelax and rejuvenate in this spacious, 1600 square foot, two-bedroom, 2-1/2 bath, two-story town-home. Located on the western perimeter of The Fairways within the Mauna Lani Resort complex,...
Ma'alaea Surf, Unit D5-1BR Ground Floor Beachfront Condo, AC, Wifi, Pool, TV
In the heart of paradise, Unit D5 at Ma’alaea Surf Resort awaits with its newly refurbished charm. Nestled just 5 steps away from the soft embrace of the white sandy beach, this ground floor haven of comfort and a touch of Hawaiian country style living, D5 envelops us...
KBM Resorts | FREE CAR Kapalua Golf Villa KGV-24P7, Ocean + Golf Views!
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
Kona Alii 403: Tropical Oceanfront Condo w/ AC & Pool in Downtown Kona
Welcome to Kona Alii 403, a beautifully remodeled oceanfront condo in the heart of historic Kailua Kona, HI. Offering 780 square feet of thoughtfully designed living space, this one-bedroom retreat perfectly combines modern comfort with the timeless beauty of the...
Wailea Beach Villas PH211 - 2 Bedroom Garden View Penthouse
Indulge in entertainment abound when vacationing in Wailea Beach Villas Penthouse 211. After you’ve spent an action-packed day at the beach or hiking one of Maui’s scenic trails, return to your vacation residence and discover some more relaxing entertainment options...
Amazing Ocean Views - Steps To Beach - Newly Remodeled
Our luxurious one bedroom, one bath, non-smoking condo has amazing ocean views, and breathtaking sunsets from the beach. We are located at Sugar Beach Resort, which is steps away from the white sandy beach, and incredible ocean access.As you relax on the private lanai,...
Escape to Tropical Bliss, Our Dreamy Oasis at the Plantation at Princeville
Nestled between mountains and sea on Kauai’s spectacular north shore, our family's air conditioned condo welcomes you. Savor the Polynesian elegance and comfort of this charming & spacious townhouse, where you’ll enjoy lush, tropical surroundings with garden views and a...