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.
OCEAN and POOL View, remodeled 2 bdrm condo with A/C - PAPAKEA K406
Stunning Ocean and pool view Papakea 2 bedroom / 2 bathNewly remodeled throughout & new furnishings2 beautiful swimming pools, 2 ocean side cabanas, jetted spaPool side BBQs3 tennis/pickle ball courts & 2 putting greensWalking distance to stores and restaurantsShuffle...
Maui Kaanapali Villas #A102: At the heart of the Maui Ka’anapali Villas Resort,
Maui Kaanapali Villas #A102: At the heart of the Maui Ka’anapali Villas Resort, a tropical retreat awaits. This ground-floor condo has two bedrooms with en-suites and a half bathroom. The primary bedroom is just off the living area and features a king bed. The second...
Hapuna Beach Residence A32 at Mauna Kea Resort
This extraordinary, oceanfront, family-friendly, third level masterpiece offers floor-to-ceiling sliding window walls that create indoor/outdoor living space, a magnificent chefs' kitchen outfitted with professional-grade Wolf, Sub-Zero and Miele appliances, wine...
Beautiful 2 Bedroom / 2 Bath / Sleeps 6
The beautiful home is located on the east side of Oahu in Hawaii Kai. Located near beaches such as the famous Hanauma Bay, restaurants, shopping centers,hiking trails, scenic lookouts and water sports. The home offers 2 bedrooms (2 queen beds), 1 sofa bed and 2...
3BR condo with A/C, pool & 10min walk to the beach!
RENTAL CARS We also have rental cars available. Please check with us if a rental car is available for your dates. We just recently bought this beautifully decorated, spacious vacation home! Our luxurious 3 bedroom/2.5 bathroom condo is a perfect place to unwind, leave...
Oceanfront - Kanaloa at Kona - Newly Remodeled
OCEANFRONT CONDO - As Kona residents for 25 years, our desire is to share ALOHA. This is your opportunity to Experience Tropical Paradise, spectacular sunsets year-round, spouting whales in winter, and frolicking dolphins. This secluded and prestigious 18 acre Resort is...
Direct Oceanfront 2BD, Kaanapali/Kahana area, FANTASTIC! Home Away from Home!
Maui is outdoor living at its finest! Enjoy having breakfast lunch and dinner on your lanai staring at the ocean! Wake each morning to birds singing, swaying palm trees and the teal blue waters of the ocean.. there is no escaping the absolute OUTSTANDING view from this...
Honu House; Unit 209, Amazing views!! Watch the turtles & whales from lanai!
Honu House, unit 209 is a corner unit, in an oceanfront complex located in Honokowai, just minutes away from downtown Lahaina! This unit does NOT have A/C. Second floor condo with an ocean view and just steps from access to the ocean. The unit is freshly painted through...
It's All About the View! Oceanfront, A/C, Elevator
2025 UPDATE: SPECIAL! The dates of 9/3-9/24 have been discounted due to the closing of the pool area for renovations. The SPECIAL rate will be $180 + 17.962% + $185 one-time cleaning. The standard nightly rate is $280 + 17.962% + $185 one-time cleaning fee.Enjoy the...
Sweeping Ocean Views - Makena Surf Resort C-106 - Peaceful Ground Level Gem
Makena Surf C-106Nestled within the exclusive Makena community, Makena Surf Resort is a luxurious beachfront retreat offering spectacular views of the Pacific Ocean. This gated property features six carefully designed two- and three-story buildings, each strategically...
Hapuna Beach Residence B22 at Mauna Kea Resort
This spectacular, oceanfront, newly-constructed studio offers floor-to-ceiling sliding window walls that create indoor/outdoor living space, a luxe chefs' kitchen outfitted with professional-grade Wolf, Sub-Zero and Miele appliances, wine storage, plus a dining table...
Get Away to Paradise
COVID Free Quaint 3 bedroom 2 1/2 Bathroom condo located in Ko' olina Fairways. Perfect place to unwind and relax. Two story with 3 bedrooms and two full bathrooms upstairs and kitchen, living room dining room and half bath downstairs. All the comforts of home to...
Romantic 1 Bedroom Home at Anini Beach! - Sleeps 2
Retreat from the cares of the world in this tastefully furnished, one-bedroom, one-bath, oceanfront home.TVR #5082 Punana Aloha, which means 'Love Nest' in Hawaiian, is a one-bedroom, one-bath hideaway on incomparable Anini Beach. Constructed of natural cedar...
Oceanfront Luxury Home with Beach Access and Private Pool - 5 bed/5 bath
Perfect for Families and Large Groups!Overlooking the dramatic Kona Coast, an oceanfront Oasis; sits Mele Kai — a luxurious island sanctuary welcoming guests in search of unforgettable memories and warm Hawaiian hospitality on Hawaii’s Big Island. Oceanfront suites...
New Luxury Home in Nohea w/ Private Pool Spa and Two Ohanas
Step into refined island living with Abita Luxury Rentals at this 3,000 sq ft, 4-bedroom home built in 2023 in Nohea at Mauna Lani. Combining sophistication and comfort, this private retreat features a private pool and spa nestled among tropical landscaping along the...
F207 Spectacular Ocean Views - Beautifully Renovated Condo - 2 New Pools
We are pleased to announce that Makena Surf has completely renovated the South Pool! This beautiful new space is a welcome addition to the paradise we call Makena Surf!This beautiful Makena Surf condo provides the best that Maui has to offer. High end furnishings and...
Sandy Beach Front Property - Family Friendly - 4 min stroll to H2O - Ocean Views
Escape to paradise to our family friendly beach front property, Wailea Ekahi Villas unit 35B. 35B is a luxurious 2-bedroom, 3-bathroom 2 story condo (nobody above you!) and only a 4-minute walk down a gentle slope to Keawakapu Beach, a mile-long stretch of pristine...
Hilo Lagoon Retreat – 2BR w/View, A/C, Pool
Relax and Unwind at Hilo Lagoon CenterWelcome to your home away from home in the heart of Hilo! This spacious 2-bedroom, 2-bathroom condo offers comfort, convenience, and beautiful views of the peaceful waters at Wailoa River State Park.The spaceInside, you’ll...
🏖️New Listing! | Beautiful Townhome | Great Location | Concierge Included!
vrKCV - Kulalani at Mauna Lani 205 - Professionally managed by Kona Coast VacationsSecluded Kulalani Villa in the Mauna Lani ResortYour perfect vacation in a tranquil tropical oasis! Kulalani at Mauna Lani is a private gated community of quiet luxury townhomes,...
4BR Bali Inspired Luxury Home in Kukuiula
Hale Kahakai is a stunning four-bedroom luxury vacation rental in the highly desirable Kukuiula neighborhood in Poipu. Inspired by the villas in Bali, you'll admire every thoughtful detail put into this luxury home, from the latticework carved gates to vaulted ceilings...
Oceanfront Living at Luxurious Mermaid Manor in Kailua-Kona, Hawaii
Welcome to your oceanfront home in the heart of Kailua-Kona! At Mermaid Manor, the ocean is literally your backyard—no road, no fences, just lava rocks and tidepools steps from your door. While some homes across the street may say "oceanfront," we invite you to truly...
Kauai Oceanfront Condo Princeville, Pali Ke Kua 218, Best views, End unit
Beautiful Princeville Pali Ke Kua condo perched on a cliff overlooking Bali Hai, with unobstructed views of the ocean, sunsets, waterfalls, and rainbows. Turtles can be seen swimming in the cove below. December through April whales can be seen on their journey to and...
Direct Beachfront Spectacular Ocean Views Fully Renovated!!
Imagine the thrill of expansive direct ocean views from every room and the covered lanai! Kihei Kai 9 is the only true beachfront penthouse or top floor condominium in boutique Kihei Kai. Drift to sleep serenaded by lapping waves.This fully remodeled one bedroom pampers...
Oceanfront Tranquility at Hale Maluhia, Kona Coast
Beautiful oceanfront property featuring a private gated home with two additional separate king Bedroom Suites, each with private entrances. Enjoy unobstructed ocean views of the Pacific Ocean, Kona Coast, and Kahalu'u Beach with stunning sunsets. This property includes...
Ekahi 38-A Luxury and Grace Located in Sunny South Maui
The Quiet Luxury and Attention to Detail Will Give You the Sense That You Have Arrived Home. Our Unit is Air-conditioned With a Master Bedroom / Bath Suite That Includes a New Serta King Mattresss With 1000 Count Prima Linens, Fluffy Bath Towls for the Bath and a...
Hale Luana – Luxury Oceanfront Vacation Estate on Poipu Beach
This stunning beachfront estate is located directly on the pristine sands of Poipu’s Baby Beach, making it one of the few oceanfront rentals in Kauai that offers both beach access and proximity to shopping and dining options in Poipu. Nestled above a shallow,...
Kaanapali Alii | 322
Welcome to Kaanapali Alii 322, where understated elegance meets the beauty of tropical paradise. This stunning residence offers refreshing views of lush gardens, creating a serene backdrop for your Hawaiian getaway. The elegantly designed living area opens up to a...
6BR/6BA Luxury Villa w Pool, A/C, Walk to Beach!
Perfect for large families, wedding groups, or multigenerational getaways, this setup offers two side-by-side first-floor villas in Po‘ipu’s newest luxury complex—just a 5-minute walk to top-rated beaches and the Grand Hyatt. With 6 bedrooms, 6 full bathrooms, 2...
LUXURY VILLA - 3BR/3BA with Pool & A/C - Short Walk to Beaches
Welcome to Sugar Sands Villas!Luxurious and spacious (1600+ sqft) 3 bedroom 3 full bathroom villa with central A/C (rare in Poipu), fully-stocked gourmet kitchen and folding glass doors that open to a private lanai with lush views of the Po'ipu Greenbelt. Walk to...
🏖️Easy Walk to Village | Air-Conditioning | Ocean View | WIFI | vrKCV
vrKCV - Kona Pacific D622, Professionally Managed by Kona Coast VacationsWelcome to Our Home on the Big IslandAloha and welcome to our home on the Big Island, a place of wonder, diversity, friendship, and beauty. As our guests, please relax and enjoy everything that our...
Foster Tower Waikiki Beach Condo
Foster Tower is located steps away from beautiful Waikiki Beach. This is a one-bedroom unit in a highly desirable building and location. Enjoy beautiful ocean views and immediate access to the beach for surfing, swimming, and snorkeling, hundreds of restaurants, the...
🏖️Luxury Island Oasis | Spectacular Ocean Views & Pool | vrKCV
vrKCV - Aloha Place, Professionally Managed by Kona Coast VacationsAloha Place – Luxurious 3-Bedroom, 3-Bathroom Home with Spectacular Ocean ViewsExperience the ultimate in luxury and tranquility at Aloha Place, a Bali-inspired retreat perched in the serene upper Kona...
Marriott's Ko Olina Beach Club 2 BR Oceanview Villa
Just half an hour from Honolulu, Ko Olina Beach Club is nestled among the lush grounds of Ko Olina Resort & Marina, a picturesque 640-acre community built along a pristine stretch of the Oahu coastline. Situated in the stunning southwest region of Kapolei with...
Beautiful "Beachfront" House on the Beach at Sunset Beach Paradise on the Beach
A Truly Luxury Beachfront House Located on World Famous Sunset Beach on Oahu's North Shore. Named 'Paradise on the Beach' at Sunset Beach by many guests this premier Direct Beachfront two-story, two large bedrooms, three full baths, executive style house affords the...
Ko Olina Beach Villas B901: Luxe 3BR Penthouse w/ Beachfront Views
Welcome to Ko Olina Beach Villas B901 by Gather, a luxurious penthouse in the heart of the Ko Olina Resort. This exclusive ninth-floor beachfront vacation rental offers breathtaking ocean and pool views, providing an unparalleled experience for those seeking a tranquil...
Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui
The Hamoa Bay Bungalow is HANA MAU'Is most charming vacation hide-away. Balinese inspired, private, with partial ocean views, secluded and romantic. Just beyond sleepy Hana Town... this property is tucked in amongst lush ferns, banana trees, bamboo, colorful heliconias,...
Direct Ocean Front Property Wailea Ekahi 16A 2 Bed 2 Full Bath Ocean Views 5star
5-Star - Unit 16A: 2 Bed/2 Bath. Ocean Front Property - Ocean Views:Imagine waking to the gentle lull of trade winds and a panoramic ocean view, featuring the West Maui Mountains and the island of Lanai in the distance. This is the promise of a perfect day in paradise...
Makahuena 1202. Partial Ocean View, 2 bed, 2 bath with AC. Poipu.
Located on the southern most point of Kauai, right between Poipu Beach State Park and Shipwreck Beach. Partial ocean view. Nicely remodeled 2 bedroom, 2 bath condo with Lanai. Master bedroom has a king bed, 2nd bedroom has 2 twin beds that can be moved together for a...
Beach-AC-Pool-Gym-Oceanview-Garden-two lanais-212, Spectacular View w/ W/D and AC
Relax! Condo on Kiahuna Beach! Updated Stone Countertops, cabinets, and open concept! This amazing oceanview Kiahuna condo with AC overlooking the garden/lagoon on the most beautiful resort grounds on the south shore has plenty of space for the whole family! The pool...
Hawaiian*Elegance*FULLY REMODELED OCEANVIEW 2 Bdrm
Indulge in the epitome of Hawaiian luxury within this impeccably renovated condominium. Immerse yourself in the tasteful Hawaiian decor that effortlessly transports you to paradise. The well-appointed interior boasts high-end furnishings and comprehensive amenities for...
Maui Resort Rentals: Honua Kai Hokulani 546 - Spacious 2BR w/ Partial Ocean & Mountain Views!
Perfectly positioned to provide guests with the ideal combination of Maui scenery, Hokulani 546 showcases gorgeous views of both the blue Pacific Ocean and the lush West Maui Mountains. With over 1100 sq ft of luxurious living interior, this spacious two-bedroom suite...
❤️PiH❤️ BIG ISLAND OASIS ★ Family Oasis★Free Hilton Passes ★ Bikes & Ping Pong★
Big Island Oasis brought to you by Paradise in Hawaii Luxury HomesWelcome to our 4 bedroom Big Island Oasis at KaMilo, on the Big Island of Hawaii\Big Island is such a wonderful place to spend with your friends and family, children and grandchildren. Vacations create...
99 Steps to the Sand - Ground Floor 3 Bedroom - Hokulani 104
This condo is zoned hotel and is in legal compliance with all Maui County ordinancesGround-Floor Oceanfront Suite and Wraparound Lanai at Honua KaiE komo mai (welcome) to Kai Hele Ku ("The Quickest Way to the Ocean"), where the warm embrace of Maui's kai (sea) and the...
Beautiful Pacific Shores Condo 2BR, 2BA Full A/C & ready for your Maui visit!
This VRBO listing is a fully renovated and very well furnished and equipped condo located in the Pacific Shores complex in the heart of South Kihei, Maui. It is just steps away from wonderful beaches, restaurants, and shopping.The unit includes two bedrooms (each with...
MARRIOTT WAIKOLOA OCEAN CLUB, Top Rated Resort On The Big Island!
Please choose a Friday, Saturday, or Sunday check-in and enjoy a seven or night stay. If you need larger accommodations, ask our agent about our two bedroom option. Thank you for your interest in booking with DashWeek/ Dash Realty Group, Windermere Florida. Dash Realty...
Ilikai 824
Top-of-the-line modern, high-end designer remodel. The direct ocean view will greet you as soon as you open the door! This studio unit boasts a unique feature of separation doors that create a one bedroom atmosphere. The open floor plan sweeps from the full size...
Ilikai 30-Day Rental in Waikiki
This rental is on the 19th floor of the Ilikai Hotel with direct lagoon and ocean views. This 1 bedroom apartment has been remodeled into a large 500 sq ft studio and is gorgeous! High-end materials were used throughout the apartment. We used beautiful flooring in the...
Luxurious Tropical Retreat Wailea Ekahi Unit - 31 D
Luxurious Tropical Retreat - Unit 31D is truly "one-of-kind"!Ideally located overlooking the lower Ekahi Village, Unit 31D provides our guests with the best of everything Maui has to offer: spectacular views, privacy and a short stroll to the beach and main pool.With...
Exquisite on Paradise*Fully Upgraded with Ocean Views!
This freshly renovated condo offers stunning ocean views and a large, airy lanai with comfortable outdoor seating. Pack up the cooler and head to the beach or lounge by the pool and soak up the serenity that is Kauhale Makai.This roomy condo is just steps from the...
Villa Moana - Beachfront Perfection
Spacious Luxury Beachfront Private Villa - 8 BR - 3,850 Sq. Ft. - Newly Built. Right on the beach in Kihei. Hosted with aloha and professionalism. Locally owned and operated. If you need more or fewer bedrooms, please send us a note and we can offer a customized rate....