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.
Wailea Elua Village | 905
Wailea Elua 905 is a vacation rental situated in the picturesque beach locale of Maui. This spacious three-bedroom, two-bathroom condo offers a perfect blend of comfort and luxury, making it an ideal retreat for families or friends traveling together. This condo is...
Private Cottage In The Rain Forest TA065882726401
Cozy, private rain forest retreat cottage situated above Kona in the Kaloko Mauka Honua'ula Forest Reserve. Located on a 3-acre property, this cottage is set away in a lush forest of Ohia trees and Hapu'u tree ferns. Enjoy the sweet aroma of ginger surrounding this one...
Beautiful Maui Condo Steps from the Beach in Kihei!
Live like a local during your stay at Kihei Bay Vista unit D110!This ground floor unit features a large lanai overlooking the tropical green lawn, mere moments from the sparkling shore!Our private oasis provides you a home away from home with a king sized bed, full...
Palm Maui County permit STPH 20130018
Maui North Shore Oceanfront Cottage 2 bedroom oceanfront cottage, sleeps 4, one rental group at a time. Relax in this charming bungalow or under the palm trees. Enjoy the surf or the nearby swimming beach or watch the turtles swimming. Minutes from world famous Ho'okipa...
Contemporary Luxury condo minutes from Hanalei Bay & other stunning beaches.
**If you are effected by the devastating fires in Maui please let us know*****Security cameras are located outside above the front door and above the sliding door on the lower level lanai. Both cameras do not look into private spaces.**The North Shore of Kauai is one of...
Rocky Point Hale Luxury Oceanfront Vacation Home in Haleiwa
The Rocky Point Hale is a quintessential North Shore custom built luxury home located at the peak of the famous Rocky Point surf break. The home is situated in a private setting on the point out of view of ocean goers and public beach accesses, yet its location allows...
Quaint COTTAGE ~ Walk To Coffee shop, nearby Road to Hana & Haleakala
We invite you to stay in our quaint and nicely decorated Haiku Surf Cottage on the North shore of Maui. IMPORTANT!!! Beware of scammers advertising our home on CL. Only available to rent from Amy - the real owner. SUMMARY: Walk out the back gate to the coffee cafe or...
2 Bed 2 BA with Full Direct Views of Bali Hai and Hanalei Bay! This is Paradise!
From the moment you walk into 4221/4222 and see Bali Hai and Hanalei Bay directly in front of you, you will know you are in paradise. Enjoy the sunsets from the slate covered lanai and hear the waves of Hanalei Bay below. This 2 bedroom, 2 bath, recently remodeled condo...
Poipu Sands 116 - Ground-Floor Condo with Pool & Hot Tub Access, Steps from Stunning Beaches
POIPU SANDS 116 AT KOLOA KAI VACATION RENTALSA Tropical Retreat with Stunning Ocean ViewsWelcome to Poipu Sands 116, a spacious 1,353-square-foot ground-floor condo nestled on the sunny south shore of Kauai. Featuring breathtaking ocean views, easy access to Shipwreck...
Mango Sunsets: Gorgeous Oceanview Estate w/Private Pool, Spa & AC
We invite you to sit back, relax and experience the dazzling sunsets, tropical breezes and never ending ocean views from "Mango Sunsets", our private 3-acre Kohala Ranch estate where modern elegance meets traditional quality craftsmanship. This previous popular vacation...
Waikiki Banyan Upscale 1 BR
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...
Kanaloa at Kona 3304: Delightful Oceanfront Condo w/ AC, Pool & Spa
Just a stone's throw from Heeia Bay, this private and spacious condo offers the ideal oceanfront setting for your Kona Resort getaway. Complete with huge ocean views, lovely Hawaiian décor, central air conditioning, wireless internet, cable, and a washer and dryer,...
Wow !! What a Great View!!--GREAT REVIEWS !
WOW !! What a GREAT view! We've heard this comment many times from vacation rental guests and friends visiting our Maui condo.Sweeping ocean views greet you as you enter, and are visible from nearly every room. The walk to the beach is less than 4 minutes. When you turn...
Poipu Kai Hale - Oceanfront Elegance at Makahuena Point
Welcome Poipu's Hidden Gem! This amazing home offers 3 bedrooms and 3 bathrooms on the ocean with incredible views of Poipu! Imagine your vacation experience in this gorgeous location with unparalleled and unobstructed 200°+ views. This spacious home consists of a...
New Listing- Impressive 3 Bd+2 Bath Vacation Home at Wailea Grand Champions
Bldg. 16 - Unit #153 - A front-row, ground floor, impeccable 3 Bedroom + 2 Bathroom paradise condominium at the Wailea Grand Champion Villas. This is a prime example of what Wailea Grand Champion Golf Villas has to offer in a 3 bdrm + 2 bath category. Upgraded...
2026 Available Westin Nanea Award winning beach! Breathtaking Sunsets! 1/3-1/10
Currently holding the dates 1/3-1/10/26 The Sentry marks the season-opening event of the 2025 FedExCup Season. The PGA TOUR’s Opening Drive at The Sentry and Sony Open in Hawaii welcomes players looking to get to a strong start in the race. Sentry is being played at...
Oceanfront Island Living at its Finest! Unbeatable Panoramic Ocean Views!
Waikiki Shore #1400 – 2161 Kalia Rd.TRUE direct beachfront unit overlooking the sandy Waikiki shoreline with breathtaking panoramic ocean views! Full kitchen, free Wi-Fi, free parking for 1 vehicle. This 1-bedroom condo's generous 1,188 sqft of interior living space...
Gorgeous Home on Landscaped Acre-2BR/2BA
Welcome to Pua Lani, a gated one acre estate two blocks from the ocean that features resort landscaping and large lawn areas that create a very private and serene setting for your stay. The two story home features 2 bedrooms and 2 baths along with a large high ceilinged...
Oceanfront Studio in Kahana - Pohailani 201
Ocean Front Studio in Kahana. Remodeled and ready for occupancy! This condo is so close to the ocean you can hear and smell the ocean. Whale watch or view the large sea turtles from our lanai. Sleep like a baby on our Westin Heavenly King bed. Got 2 more? We also have a...
Kaanapali Alii | 424
Experience the ultimate tropical escape at Kaanapali Alii 424. In this exquisite two-bedroom plus den ocean view rental at Kaanapali Alii, luxury meets serenity along Maui’s breathtaking coastline. This spacious retreat offers an unparalleled combination of comfort...
Combo Booking: Luana Garden Villas 14D, 15D & 18C at Honua Kai~sleeps 24 guests
Welcome to Luana Garden Villa, where paradise awaits you at Honua Kai Resort & Spa in Kaanapali, Maui. Our luxurious and spacious condos, Luana 14D, Luana 15D and Luana 18C, offer high-end amenities and stylish decor, ensuring comfort and luxury during your stay. Each...
Hilton Pool Pass thru June 2025. Waikoloa Colony Villas 1303
This vacation rental is professionally managed by ResorticaHawaiiGolf Views • 2 King Beds + Sleeper • Pool Access + Hilton Waikoloa Resort Pass🌺 Waikoloa Colony Villas 1303 | 2 Kings + Sleeper | Golf Views + Hilton Pool Pass thru December 31, 2025🌴 Steps from...
Hale Awa'puhi 1-C Oceanfront Luxury 2 BR w/ AC and Private Beach Access
Welcome to Hale Awa'puhi 1-C, an oceanfront gem among one of the most luxurious oceanfront condominiums on Kaua’i in a gated boutique 9-unit property on a private cove. Relish the panoramic ocean views and the soothing sound of surf while relaxing in this modern...
Kihei, Maui - Fully Renovated, A/C, Pool, Tennis, Beach
This condo has been completely remodeled floor to ceiling! - New tile, bathroom, kitchen, appliances, and new furniture & bedding throughout.Condo Includes:- Stackable washer and dryer with complimentary start-up detergent supply- A/C in the living room and bedroom-...
*Remodeled Oceanfront in Waikiki - Ilikai Marina
Welcome to our oceanfront home offering stunning ocean views and Hawaiian sunsets, all within walking distance to the beach. Whether you're seeking adventure, family fun, or relaxation, this is the perfect destination while visiting Oahu. On Friday nights, enjoy...
Luana Garden Villa 6D @ Honua Kai Resort Kaanapali
Stay in an ocean front luxury villa in Maui, steps from Kaanapali Beach. Discounted Rates are offered for this family-friendly sanctuary of tranquility, natural beauty, and openness. Relax on the 500 sq. ft. lanai and feel the Pacific air gently flow over you. Enjoy a...
Waikoloa Resort gem with pool, hot tub & balcony - 1 mile to beach
Waikoloa Fairway Villas B32Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Experience the best of Hawaii from this third-floor 2BR/2BA condo at the Waikoloa Beach Resort. Soak up the...
Charming Hale Mokolea in Lanikai –2BR, 2BA, Full Kitchen
Nestled in the beachside community of Lanikai, Kailua, this fully furnished home is over 1400 square feet of island style living. Beautifully yet simply decorated, this unit is the whole upper half of the main house. The entrance is at mid-floor level with a Brazilian...
Premium Studio Suite on Beautiful Ka'anapali Beach
Beautiful premium condo resort on Ka'anapali Beach. Studio condominium is 480 sq ft with king size bed and a sofa sleeper and small kitchen with full refrigerator, microwave, dishwasher and 2 burner cooktop. In-room amenities include Jacuzzi tub, DVD player, private...
🏖️New to Vacation Rental! | Professionally decorated August 2023 | Concierge Included | vrKCV
vrKCV - Mauna Lani Fairways 801, Professionally Managed by Kona Coast VacationsWelcome to our Hawaiian home on the sun drenched Kohala Coast - 801 Fairways at Mauna Lani ResortSoaring ceilings, bright open concept living, a large comfortable lanai backing onto the golf...
Newly Renovated 3 BR, 3.5 Bath Oceanfront Estate with Pool, Spa, A/C and Turtles
Our home was updated during the last half of 2021 and in early 2022 with new cabinets, countertops, appliances, sinks, faucets and dimmable recessed lighting in kitchen, baths, wet-bar and laundry; all new showers and a free-standing tub in the baths; all new walnut...
OCEANFRONT. Amazing views of dolphins and sunsets. Newly renovated. No stairs.
RIGHT ON THE WATER in one of Kailua-Kona's most sought after complexes! This open and spacious, 2-bedroom condo has a spectacular, 180-degree, Kona coastline and ocean view. From the private lanai, watch spinner dolphins as you savor your morning Kona coffee. Later,...
Luxurious, Private Suite
Luxury Suite with Private Entrance~We have created a peaceful, sparkling clean and private Studio Suite, including plush linens and stocked with over-the-top amenities. We provide all the basics and much more, like flashlights/lanterns, binoculars, beach towels, yoga...
Dream of Aloha
— "This property may not be rented for less than 30 consecutive days. Rental prices will not be reduced or adjusted based on the number of days the rental is actually used or occupied." (PER CITY AND COUNTY OF HONOLULU). — This property cannot accommodate long...
Private, Serene & Cute Cottage. Ocean Views & A/C. Near Hana Hwy.
Relax & enjoy the peace & quiet, coastal ocean views, lush tropical setting & complete privacy at your modern cottage with private lanai.Palm Cottage is ideal for a quiet vacation, honeymoon or just a peaceful getaway. Come to quiet, rural Maui to get away from the...
Includes Mauna Lani Beach Club Pass. 1702 Kulalani
Kulalani 1702. Includes Mauna Lani Beach Club Pass This vacation rental is professionally managed by ResorticaHawaiiPlease scroll down for detailed informationBedding Configuration:Master Bedroom: King BedGuest Bedroom: King BedGuest Bedroom: Queen BedMauna Lani Beach...
Valley Isle Resort #707 - Vacation West Maui - Beachfront Luxury
From the moment you arrive to Valley Isle 707, you will be mesmerized by the views of Molokai and Lanai. Step inside and find a spacious, modern living space with porcelain tiled floors, a luxurious queen-sized Murphy bed, and a comfortable loveseat sleeper sofa. The...
Kaanapali Alii | 155
Welcome to the paradise of Maui! Nestled along the pristine shores of Kaanapali Beach, this two-bedroom oceanfront condo offers a slice of paradise like no other. As you step into your luxurious home away from home, you'll be greeted by stunning ocean views.The spacious...
🌺🍍Direct Oceanfront Condo with Amazing Views!! 🍍🌺
Welcome to "My Hawaiian Condo" - Hale Mahina Unit A405!Hale Mahina (Ha-lay Ma-hee-nah), is one of the most unique properties on Maui's West side.Just a few miles from the big resorts and crowded beaches of Kaanapali, Hale Mahina is situated on the ocean front with a...
ALOHA-WAIKIKI 2 Blocks 2 Shoreline of BEACH and Upgraded!!!
Located just two short blocks from the shoreline, this unit features a comfy queen sized bed, free wifi, a kitchenette, private bathroom and a private covered balcony from which you are able to enjoy mountain views and tropical breezes.Within our CLEAN PRIVATE unit, my...
Lanikai Cottage: Charming Tropical Oasis w/Private Pool & A/C, Walk to Beach
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.Charming Lanikai Cottage features two...
KBM Resorts | FREE CAR | Honua Kai Konea | Ocean view | 2-Bedroom Condo, Great for Families! HKK-213
Spacious 2-bedroom, 2-bathroom Honua Kai condo featuring ocean and pool views, large wrap-around lanai, gourmet kitchen, and full access to resort amenities.** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and...
BEAUTIFULLY UPDATED-WELL EQUIPPED-LARGE LANAI-AC-METICULOUS CLEANING
Book with confidence, this stunning, 2 bedroom, 2 bathroom (1188 sq. ft) condo that has been beautifully updated. This condo is managed by PMI Maui, a local Real Estate Brokerage that specializes in vacation rentals. We are located within a mile of the resort and...
Waialua Oceanfront Luxury Home – Secluded North Shore Escape
Featuring Two Master Suites!!!Search no further - this luxurious oceanfront beauty has all the makings of a heaven-sent vacation on one of Oahu's most secluded coastlines. Furnished throughout with hand-picked Balinese furniture and decor, this home is a treat to see...
Beachfront Condo B303 May 10-15 available at special rate of 750 per night
Relax and enjoy panoramic views and beachfront perfection. The 2 bedroom, 2 bath home is located in the B building and sits only steps from an extraordinary sandy beach offering the famous 'five island view' along with the accompanying year-round sunsets. A refreshing...
Kauai Luxury home, Private Pool & Spa, walk to the beach, restaurants and shops
We have just added a private pool & Spa and a 5 th bedroom suite(3/12/25),We have not updated the video yet but have added a few photos. AC in all rooms of home. 5 master suites with private bathrooms, each with a private lanai. Gourmet Kitchen, Large lanai deck for BBQ...
Paradise at Mauna Lani- Private, Modern Townhouse
Welcome to ParadiseHidden away in the outer rim of The Fairways community in the coveted Mauna Lani resort area sits this spacious and modern 2 bedroom, 2.5 bathroom, 2-story townhome. This area along the south Kohala Coast of the Big Island is regarded as having the...
Ocean-view condo at White Sands Village #216, steps from Magic Sands beach!
Welcome to White Sands Village, # 216! Enjoy this two-bedroom, two-bathroom, fully air-conditioned condo. Located just across the street from Magic Sands beach, along the iconic Alii Drive, this new, completely remodeled condo has all the amenities you could need! Smart...
Luxury 4BR Penthouse at the Villas at Poipu Kai
Welcome to The Villas at Poipu Kai, one of the nicest luxury condominium resorts on the South side of Kauai in Poipu. These spacious and upscale villas are part of the Poipu Kai Resort that offers access to additional recreational amenities to all in the Poipu Kai...
Includes Hilton Waikoloa Pool Pass thru June 2025! Waikoloa Colony Villas 1605
This vacation rental is professionally managed by ResorticaHawaiiWaikoloa Colony Villas 1605 Please scroll down for detailed informationHilton Pool Pass: Valid for stays through December 31, 2025. Maximum 6 persons per pass (children under the age of 5 are not counted...