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.
Best Window seats to Ocean Views- in wonderful Ocean View HI with WiFi
If you love Hawaii, then this place is for you. The Guest house has magical views of South-point beach with panoramic views from the oversized window seats. South-point is the southernmost tip in the United States and a national historic landmark! Shore fishing, tide...
3 Bedroom Penthouse W/Private Lanai–Poipu Shores
Nestled along the shoreline, this serene haven offers sweeping ocean vistas and mesmerizing sunset displays that will leave you in awe. Step inside this stunning oceanfront penthouse, where breathtaking ocean views of the Pacific Ocean welcome you home. Designed with...
Ko Olina Beach Villas O805: Chef's Kitchen & Stunning Views
This villa features impressive ocean views from the large lanai, as well as mountain and golf course views from the back lanai. For convenience, the elevators are steps away from the parking entrance door and open to your semi-private floor. A full kitchen and open...
Discover Your Paradise at Royal Mauian 104
Welcome to Royal Mauian 104, where luxury meets the beauty of Maui’s coastline. Nestled on the ground floor of the prestigious Royal Mauian complex, this modern 2-bedroom, 2-bathroom condo offers the perfect blend of style and comfort. With direct access to manicured...
Relaxing garden setting with ocean view A210
Watch the life of Maui unfold from the morning till evening from your private 114 sq foot private view deck. Premium condo suite located near the pool area. Second floor means easy access to tropical gardens and the ocean beyond. Quiet location features large private...
Maui Kamaole F-106 Garden View, Walk to Kam III Beach Park in Kihei
Garden Paradise at the beautiful Maui KamaoleDon't get us wrong- the entire Maui Kamaole property is gorgeous in itself, but this condo is one to behold. It is located in a quiet corner of the property in one of the last buildings to be completed meaning a new and...
Holua Kai#8 w/ Private Pool, Ocean & Golf Views, Community Pool & Spa
Holua Kai #8 invites you to unwind in style within the private gated community of Kona Country Club Ocean Course. This elegant single-level home blends open, light-filled interiors with a private heated pool and lanai framed by lush golf course greens and distant...
Ma'alaea Surf, Unit H3-Ground Floor Beachfront Condo, AC, Wifi, Pool, TV
Ma'alaea Surf, Unit H3 is an ideally located ground floor condo, just steps from Sugar beach. This condo features a full kitchen and dining table. The master bedroom has a king-sized bed. The large living room has expansive views of the ocean. Enjoy Maui's colorful...
Poolside Waikiki Retreat w/ AC, surfboard storage, walking distance to beach!
Located in the center of Waikiki with amenities like A/C, on premises laundry, and bike & surfboard storage, this spot is a no brainer. Directly across from the *eight foot deep* outdoor pool and patio, and just blocks from the beach, this apartment is truly a piece of...
Beach Studio with private yard in Lanikai - 30 day Minimum Stay
Escape to your beachside retreat with this beautifully renovated studio located just a block from the pristine sands of Lanikai Beach on the east side of the island. Designed as your ultimate home away from home, this property offers a unique blend of seclusion and...
Poipu Shores 102A Shorebreak Lanai, Ground Floor Unit, w/AC
POIPU SHORES 102A AT KOLOA KAI VACATION RENTALSEnjoy the unobstructed ocean views of Southern Kauai from the lawn-access lanai of Poipu Shores 102A! Listen to the soothing sounds of the waves breaking on the rocks just feet below while you enjoy your morning coffee in...
Beautiful Kamaole Sands Oceanview Condominium - MAUI IS OPEN FOR VISITORS!!
This beautiful, large two bedroom, two bath townhouse type unit is decorated in light, airy island decor. The living room has a cathedral ceiling with a circular oak staircase to the second floor master bedroom and bath. Interior amenities include a fully equipped,...
Last minute special 180 from 7/1/24-7/31/24! nCome and enjoy Aloooooohaa!!
Yes you can afford this great vacation in our wonderful condo, located near Wailea . We are in the Hale Kamaole resort and are on the ground floor.Features include:Nice quiet split system air conditioner throughout the condo.1. Walking distance to Kamaole Beach 3 (it's...
New to VRBO. Air Conditioned Luxury Island Retreat - Newly Remodeled
Newly remodeled ground-floor condo at Alii Kai with all new fixtures and furnishings.Located on the cliffs above Turtle Cave, you are just steps away from a private path leading to snorkeling with Kauai's magnificent Sea Turtles. Enjoy ocean views from the front porch...
Modern and Quiet Mauna Kea Gem
New to VRBO! This three bedroom home sleeps six to eight with modern amenities, a gourmet kitchen, large open floor plan, pool and spa. Located on the resort side and ocean side of the highway in one of the original Mauna Kea developments - just a short drive or walk...
❤️PiH❤️ Sun Ray Retreat ★Ocean & Sunsets Views★Optional Mauna Kea Hotel Privileges
Brought to you by Paradise in Hawaii Luxury Homes.Welcome to Sun Ray Retreat, a part of our Hawaiian Luxury Collection. Sun Ray Retreat at the Mauna Kea Resort Kumulani complex has stunning views of golf, ocean and sunsets. This three bedroom upper-level unit is...
KBM Resorts | FREE CAR | International Colony Club | 2-Bedroom Cottage, True Essence of Hawaii! ICC-11
Plantation-style 2BR cottage near Ka'anapali's Airport Beach with high beam ceilings, updated kitchen, and lush tropical gardens. Walk to the beach or relax by the pool in authentic Hawaiian charm.*Special Offer - Book any KBM rental home in Hawaii for 6 nights or more...
Maui Resort Rentals: The Whaler 212 - Gorgeous Remodel, 1BR/2BA w/ Ocean and West Maui Mountain Views!
Not previously available for vacation rental, this gorgeously remodeled 1B/2BA suite at the Whaler boasts a desirable vantage point with beautiful views of the Pacific Ocean and Maui's neighbor island Molokai, as well as views of the West Maui Mountains.Your party will...
Waikoloa Fairways #A310: Top Floor,Breathtaking Lake, Golf Course&Ocean Views
VIEWS, VIEWS, VIEWS!! This gorgeous condominium has the WOW Factor when you go to the Lanai. Absolutely Breathtaking views over the Golf Course that sweep to the Ocean over the Kohala Coast and to Maui, make this condominium a truly special property.The location, views,...
Beachfront Paradise/Ocean Views & 5 Star Reviews/ Shared pool. Steps to the Sea!
paradisesandshawaiirentals.com8083828016E’komo mai “welcome” to Turtle Bay Ocean Villa unit 210! Newly updated, painted and re-decorate- this charming 1700 sq ft villa will help make all of your Hawaii vacation dreams come true. Located on the second floor with...
A perfect suite for temporary short term visitors
To our dear and faithful previous visitors and new vacationers Please always remember we NEVER charge an owner host fee - everything you see is yours to use, eat - candy, snacks, coffee, all beach and snorkel equipment etc etc etc. enjoy and of course no cleaning fee....
Charming Guest House in Mountain View
Newly remodeled home on a two acre property will provide you a real taste of big island living. Peaceful and relaxing environment. Fresh mountain air. Magnificent native foliage. Comfortable cool climate.Explore the island by kayaking in Hilo Bay. Complimentary rental...
Beautiful 3 Bedroom Rainforest Retreat, minutes from HVNP
Come and enjoy our beautiful retreat, just minutes from Volcano Village and the world renowned Hawaii Volcanoes National Park. Designed by renowned local architect, Boone Morrison, this unique property features lots of natural wood and light, providing a wonderful...
Puna Rainforest Hot Spring Retreat - Green Bamboo Cottage
Studio with oceanview, full kitchen and bathroom, queen size bed, plus small couch for one child or small adult. Perfect for couples. The property offers 1 mile private rainforest trail, pool, steam vents, two steam vent hot springs and private retreat setting...
Kihei Surfside #508: Gorgeous Oceanfront Escape with Mesmerizing Views
Kihei Surfside #508 – Oceanfront Escape with Split-Duct AC and Breathtaking ViewsWelcome to Kihei Surfside #508, a beautifully situated 1-bedroom, 1-bathroom oceanfront condo offering unobstructed views of Maui’s stunning coastline. Perfect for two guests, this...
Hawaiian-inspired studio with ocean view
Papakea B307 is a Studio condo featuring amenities such as a stunning ocean view, a washer/dryer, and air-conditioning! The condo can accommodate up to 4 guests with a Queen-size Murphy bed. The spacious main living area includes modern furniture with tile flooring and...
Oceanfront New House on Kealakekua Bay
*We are only accepting 31+ day reservations*With construction completed during the Summer of 2020, be one of the first to enjoy the open design and simple elegance of the Dolphin House. This oceanfront house has 3 bedrooms with en-suite bathrooms. Each bedroom opens up...
Wailea Beach Villas | PH111
Curated with our guests in mind, Wailea Beach Villas PH111's outdoor elements are just as immaculate as the home’s interiors. Unwind and enjoy peekaboo views of the ocean along with tropical greenery from your private lanai. The pristine Wailea Beach is located nearby...
🌴Beautiful home centrally located in Kailua Kona. Aloha and welcome to Hale Kona!🌴
Aloha and Welcome to Hale Kona! This beautiful home is located right in the heart of Kona. It is your perfect tropical getaway.Enjoy the hot tub as you wind down for the evening. Located in a quiet and peaceful gatedcommunity, the home is just minutes away from all of...
Hokulani 509 at Honua Kai Resort ~ Rare Indoor Ocean Views & Wrap Around Lanai
Welcome to Hokulani 509, your luxury beachfront oasis at the stunning Honua Kai Resort & Spa. Marvel at breathtaking ocean views from inside this rare and unique interior courtyard, 2 bed/2 bath condo, boasting a 1300 sq ft interior with travertine floors and...
Welcoming, open and spacious 3 Bed/3Bath - Enjoy the magic of the Northshore!
If you’re looking for a prime location on the North Shore of Kauai, this is it. Villas on the Prince 34 is a 3 bedroom, 3 bath home which offers privacy in a quiet, gated, upscale community. This home is delightful and wonderfully appointed and has everything you...
Beautiful Luxury Garden View 2 Bedroom, 3 Bathroom Condo
Beautiful Luxury Garden View 2 Bedroom, 3 Bathroom Condo at #1 Rated 1st Class Waipouli Oceanfront and Beachfront Resort & Spa on the beautiful island of Kauai. This exceptionally, well decorated ground floor 2 Bedroom, 3 Bath Condo offers easy access to the pool and...
Coastal Living Celebrated-North Shore Beach House
**Please contact for availability!Experience the ideal North Shore lifestyle in this architecturally renowned Hawaiian beachfront cottage. Here you will find the perfect Island getaway for couples or small families looking for privacy, modern comfort, and direct beach...
Spacious Resort Townhome with Ocean Views & Private Pool
Four specialized Sirrus bikes with helmets included with rental. This spacious two-story town home holds 3,132 sq. feet of living area including spacious covered lanai and is a perfect retreat for families looking to stay in close proximity to hotel facilities and two...
Includes Beach Gear! Shores at Waikoloa 331
This vacation rental is professionally managed by ResorticaHawaiiPLEASE NOTE: The tile walkway on the 2nd floor of the Bo Tree Tower will be replaced from July 14-September 15, 2025. The first two weeks of the project are expected to be the noisiest while the current...
Hale Holokai at KAANAPALI VISTA~LUXURY Golf Course Ocean View Home 6 bedroom 3 bathroom~
This is a legally permitted vacation rental according to the County of Maui ordinances.Luxury 6-Bedroom Retreat with Private Pool & Lanai – Steps from Kaʻanapali BeachE komo mai (welcome) to your Hawaiian sanctuary, a luxurious 6-bedroom retreat in the heart of the...
Stunning Views! Luxury Penthouse Kahana Villa E705
Summary:Enjoy your stay in Maui worry-free! Our short-term rental property is unaffected by any proposed legislation that may impact other accommodations. Book with confidence and experience the beauty of our island without any risk of cancellation.Stunning views that...
Kaanapali Alii | 2101
Kaanapali Alii 2101 is a luxurious vacation rental nestled on the stunning western shores of Maui, offering a blend of elegance, comfort, and breathtaking ocean views. Located within the prestigious Kaanapali Alii Resort, this spacious 1,500-square-foot condo is an...
Tropical Wailea Retreat
We invite you to come and stay at our spacious suite where you can enjoy the exclusive Wailea lifestyle. Relax & restore in this serene space surrounded by tropical palms!This bright and airy 1 bed/2 bath, corner end unit is a modern Hawaiian retreat. The suite features...
KAUAI'S Plantation-style Paradise for 2! Peaceful North Shore Cottage 5-STAR!
**THIS RENTAL IS EXCLUSIVE TO VRBO - DO NOT RENT OFF CRAIG'S LIST OR ANY OTHER WEB SITE**If you are looking for the ultimate Kauai experience, then look no further! Located on the North Shore, the most desirable area of Kauai, known for its tropical lushness, sandy...
KLVR welcomes you to Honua Kai Luana upper level 5C Oceanfront Resort, POOL view
Kaanapali Luxury Vacation Rentals (KLVR) Welcomes you to the Beautiful Luana Garden Villa at Honua Kai Resort*5CLuana Garden Villas is the final phase of Honua Kai Resort and Spa, located on the stunning Kaanapali Beach on Maui’s western shores, and steps from...
★ - Rainbow Lookout! Private Hot Tub + Pool Access + New Central Conditioning
Rainbow Honeymoon Lookout at Huelo Point Lookout is the perfect starting point for adventurers embarking on the famous Road to Hana, making it a great jumping-off point for exploring Maui's stunning natural attractions. This hidden gem on Maui's North Shore is an ideal...
Marine Surf Waikiki Studio
Location, location, location! Our elegantly appointed studio is a block from Waikiki Beach, and at the center of shopping, restaurants, and nightlife. We offer FREE parking, high speed WiFi, and a well-equipped kitchen with essentials for cooking. The lanai offers a...
Spacious Ocean View Home. Steps From White Sand Beach. Private pool & spa.
Our home is perfect for a family vacation, romantic getaway or couples retreat!Enjoy our spacious home in the exclusive resort of community of Pauoa Beach. One of 46 homes in the private enclave with access to the private Pauoa Beach Club amenities: * Family friendly...
Affordable, Luxury Resort condo w/ AC @ Kam III Beach
Aloha from Maui.Our beautiful, spacious, Resort Condo is located at Kamaole III Beach Park...one of Maui's finest swimming and snorkeling beaches! The unit is fully equipped with everything you need for a great stay, including a full kitchen, washer/dryer, beach gear,...
Kepharts' Ocean-view Hale: A Home Away from Home
This five-bedroom/three-bath home sits on five acres of land in the Kohala Estates. We specifically designed and built the house as a family vacation gathering spot. Its high ceilings and 760 square feet of windows make it particularly light and airy. Tradewinds and 13...
*TOP FLOOR REMODELED OV 1BR * A204
E Komo Mai “welcome” to Maui Eldorado A204! This newly remodeled tropical condo is located in the heart of Kaanapali, one of the world's most well-known destination resorts with spectacular ocean and Kaanapali north golf course views from the Maui Eldorado,...
Charming Oceanfront retreat- Steps from the Beach, 2BR/2BA Polo Beach Club 308
For those looking for a peaceful, comfortable home base on Maui with true beachfront access. Just steps away, you can enjoy wonderful swimming and snorkeling- no roads to cross, no long walks. From our lanai, you might spot whales in the winter, turtles passing by, and...
Kona Bali Kai 411, Oceanfront, Two bathroom
Welcome to Bali Kai 411, an oceanfront condo offering a peaceful retreat with panoramic views of the Pacific Ocean. Located on the beautiful Big Island of Hawaii, this spacious 2-bedroom, 2-bathroom unit is the ideal getaway for families, couples, or small groups...
Kiahuna Plantation Luxury
STOP! You can go to our owners' website by clicking below on 'CLICK HERE' under links to more information.Why does our unit create such a high rental following? The reasons we keep hearing from past renters...1) Just steps from Poipu's best beach (60+/-, but who's...