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.
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
This is it, your quaint and nicely decorated Haiku Surf Cottage on the North shore of Maui.SUMMARY: Walk out the back gate to the coffee cafe or small local grocery store. Enjoy the outdoor shower, semi-private yard with a surfboard fence and murals and outdoor covered...
2 Bed 2 BA with Full Direct Views of Bali Hai and Hanalei Bay! This is Paradise!
Hanalei Bay Resort 4221/4222 – Bali Hai & Hanalei Bay at Your DoorstepWelcome to Hanalei Bay Resort 4221/4222 – a truly one-of-a-kind getaway offering iconic panoramic views of Bali Hai and Hanalei Bay. From the moment you walk in, you’ll know you’ve arrived in...
Mango Sunsets: Gorgeous Oceanview Estate w/Private Pool, Spa & AC
Perched high above the Kohala Coast, Mango Sunsets welcomes you to a 3-acre private estate where modern elegance meets timeless Hawaiian craftsmanship. Hand-carved Balinese doors open to reveal 2,924 square feet of open living space framed by panoramic ocean, mountain,...
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
Oceanfront Kona Vacation Rental at Kanaloa Resort – Spacious 3-Bedroom Condo with Sunset ViewsExperience the beauty of Hawaii at Kanaloa 3304, a private and spacious oceanfront vacation rental in Kona located just steps from Heeia Bay. This 3-bedroom, 3-bath Big...
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...
Wailea Ekahi Village 42C - 1 Bedroom Garden View Condo
This 1,090 square foot one-bedroom, two bathroom vacation rental sleeps four comfortably. Wailea Ekahi Village 42C is conveniently located close to the pool, but offers a quiet sanctuary surrounded by lush greenery. Featuring contemporary, yet comfortable décor...
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...
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, 2026🌴 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
Luana Garden Villa 6D is a unique family friendly, ocean front luxury villa on Maui. The Villa is located in the center of the Honua Kai Resort & Spa between the two resort towers. It is just 330 steps from Ka'anapali Beach. Very attractive rates are offered for this...
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 Vacations🌺 Private Hawaiian Retreat — Beaches Golf & Aloha Living 🌺801 Fairways at Mauna Lani - Kohala Coast - Big IslandWake up to sweeping golf-course views, relax under soaring ceilings,...
Studio by the ocean. Oceanfront property with WiFi, AC, parking, great location.
Escape to this fantastic studio in Ewa Beach. Oceanfront property, convenient amenities like WiFi and AC, queen size bed, kitchen, parking.Located just 50 steps from a natural authentic Hawaiian beach, the second house on Oceanfront property. Nothing compares to the...
Newly Renovated 3 BR, 3.5 Bath Oceanfront Estate with Pool, Spa, A/C and Turtles
Our home was updated in 2021 and 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 hardwood flooring throughout with...
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 ultimate luxury vacation rental on Maui! Nestled along the pristine shores of Kaanapali Beach, Kaanapali Alii 155 offers an oceanfront escape that promises unforgettable memories. As you step into this stunning two-bedroom condo, you'll be captivated by...
🌺🍍Direct Oceanfront Condo with Amazing Views!! 🍍🌺
Oceanfront Condo at Hale Mahina – Unit A4052 Bedrooms • 2 Bathrooms • Sleeps 5 • Oceanfront • Pool & Hot Tub • Top-Floor UnitWelcome to your Maui getaway! Hale Mahina (Ha-lay Ma-hee-nah) is a boutique, oceanfront property on Maui’s beautiful West...
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 with Private Pool
Just steps from the turquoise shoreline of Lanikai Beach, Lanikai Cottage by Gather is a beach-chic 3-bedroom, 2-bath retreat with two separate dwellings on one property and a brand-new private pool. Ideal for families or couples traveling together, this island holiday...
Polished condo with Hawaiian decor
Welcome to Maui Parkshore 213, your tropical paradise retreat on the stunning island of Maui. This 2-bedroom, 2-bathroom condo is designed to accommodate up to 6 guests, offering a comfortable and stylish escape just steps away from the beach. Please note there are only...
KBM Resorts | FREE CAR | Honua Kai Konea | Ocean view | 2-Bedroom Condo, Great for Families! HKK-213
** 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...
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: Maximum 6 persons per pass (children under the age of 5 are not counted towards the 6 person max). Use of the Hilton...
Designer-Amazing Ocean Views-Turtle Viewing Beach-Directly On Top of Ocean
Step into the island luxury of this brand new, fully remodeled 2nd-floor oceanfront studio vacation rental! Luxury and comfort all wrapped into one with ocean and island views, award-winning interiors, and access to a secret sea turtle beach. Endless ocean views from...
Spacious 2 Bdrm Remodeled Oceanfront 01 unit
Above and beyond any other unit. Stunningly large with separate 2 Bdrms. Newly remodeled oceanfront condo on the Gold Coast. This is definitely the quiet end of the building and with the additional windows on the mountain side, you get incredible cross breezes all year....
Luxury Gated Community in Princeville Resort
A vision in white, this airy and bright Princeville condominium at Villas of Kamali'i boasts 3 bedrooms and 3 baths accommodating five guests (K,K,T) in a multi-level configuration, making it an ideal property for couples or families traveling together.Overlooking the...