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.
Family Friendly Home Walk to Beach Updated Kitchen! TVNC#1117
This is a legal vacation rental permit #TVNC 1117. Please see house rules or rental agreement for actual CANCELLATION POLICY and REFUNDS. We have a new kitchen refresh!! Pictures will be up in late Jan. 2024. Nestled among Kauai's tropical wild plant life, this...
Private luxury home with high ceilings and room for 6
Welcome to the Fairways, the upscale Townhouse community located in the exclusive Mauna Lani resort community on the Big Island of Hawaii. This private gated community offers beautifully appointed luxury homes with golf course views, vaulted ceilings and open floorplans...
O-523 Sunset Hale Retreat - Ko Olina Beach Villa. Steps to the Pool and Beach!
Welcome to our Sunset Hale Retreat - Ko'olina Beach Villa. Steps to the pool and beach!Amazing beachfront condo in the Ko'Olina resort overlooking swimming pool with beautiful pool and sunset views! Pristine residence features spacious living area and lanai with pocket...
Ocean view from every room! Listen to the ocean it's good for the soul.
Enjoy our condo in lovely Poipu with vast ocean views from the lanai and Master Bedroom. You will hear the ocean, see the ocean (and the whales in season) and be mesmerized by the ocean and the sea life. Sunset Kahili is the highest condo in the area. Our resort is on...
COMPLETELY REMODELED-AC THROUGHOUT-GROUND FLOOR-METICULOUS CLEANING
Book with confidence, this stunning, 2 bedroom, 2 bathroom (1200 sq. ft) condo that has been completely remodeled. 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...
Top Floor corner unit in main building!
Treat yourself to the ultimate in tropical island luxury with a stay at this beachside condominium. This luxury condominium offers access to two close elevators and is an end unit.Situated inside the brand new Waipouli Beach Resort and Spa, this condominium is fully...
Ocean View South Maui Condo with Lanai plus FREE parking, Wifi and Smart TVs
Condo with Ocean views from lanai, living room and kitchen. One bedroom (KING bed) , one bathroom (walk in shower), Lanai with seating to enjoy the gorgeous ocean views in South Kihei, Maui. Walk across the street to Kamaole II beach. Proximity to restaurants, shops,...
*Makani A Kai B9* Maui Condo Steps To The Sand!
This 2nd story beach front condo offers direct beach access from complex grounds with views of the breathtaking Maalaea Bay, the grand volcano Haleakala and the sparkling Kihei lights at night. Enjoy your private lanai. The loft style primary bedroom features a king...
Newly Renovated Closest to Ho'olei Pool, Wailea Beach, the Grand, Fitness Center
One of a kind four bedroom Ho'olei home in Wailea!Breathtaking is the best word to describe this luxury townhouse-style villa at Ho’olei, situated in beautiful Wailea on the sunny, southwestern shore of Maui. Ho’olei is the ultimate dream home in paradise!This recently...
Minutes from Downtown Hilo, Sleeps 6
Welcome to Hilo Hale Kaumana! Minutes from Downtown Hilo, this home has everything you need for that getaway to the Big Island. Sleeps 6This fully renovated and beautifully decorated 3 bedroom, 2 bath home is the relaxing retreat you’ve been seeking. The quiet...
Ma'alaea Surf, Unit G10, 2BR Beachfront Condo, AC, Wi-Fi, Pool, TV, Kitchen
Ma'alaea Surf, Unit G10 is a two-story townhouse unit with vaulted ceilings. This unit has a large lanai, stunning ocean views and overlooks the large pool and shuffleboard court. This elegant unit features a gorgeous fully furnished kitchen and is equipped with central...
Plumeria House, Poipu Beach, Koloa Home with a View
Don't miss out on your dream vacation in this 4 bedroom, 3.5 bath home located on Kauai's sunny south shore. Sip coffee on the lanai while watching the sunrise, or sunbathe on the deck in the heated pool. The upper floor holds a spacious, gourmet kitchen, which opens to...
Maui Resort Rentals: Honua Kai Hokulani 606 - Large 6th Floor 2BR, Corner Floor Plan w/ Direct Ocean & Mountain Views
Located in one of the closest 2 bedroom columns to the ocean at the entire resort, Hokulani 606 boasts direct 6th-floor ocean views AND lush West Maui Mountain views from its prime corner location.Suite 606 affords a perfect opportunity to gather, reconnect, and...
Luxury Upgraded Condo #98, AC, Poipu Beach, Partial Ocean View
Air Conditioned? Yes!!!Only few condos at Kiahuna are Air Conditioned. We are excited to announce that as of Sep. 2, 2021, our condo is fully air conditioned.Kiahuna Resort is 35 acres of landscaped, manicured lawns and gardens. This oceanfront resort is just steps away...
Mika Kai 4 bd w/Pool and Hot Tub - Epic Spot for Whale Watching!!!
Fully Licensed Short Term RentalSTVR-19-344467/NUC-19-255GE-131-303-1680-01TA-131-303-1680-01Each guest will be asked to sign a rental agreement after booking is accepted. Fabulous furnishings and upgrades to this already beautiful house.Here is the base of operation...
11th Floor Oceanview Sunny Studio 1115! 5 Star Reviews!
Aloha from the gorgeous sunny studio Whaler #1115 at The Whaler on Ka'anapali Beach. Whaler 1115 is located on the 11th floor on the sunny courtyard side of Tower I, the north tower. This fully remodeled interior features an open kitchen with an oversized granite...
Waikomo 302 by Destination Kauai - A/C, Ground Level Updated Condo
E Komo Mai — Waikomo Stream Villas 302 | Updated Poipu CondoExperience tropical island living at Waikomo Stream Villas 302, a bright and beautifully updated 1-bedroom, 1-bath condo on the ground floor with peaceful landscaped views in the heart of sunny Poipu. The...
Kihei Garden Estates B-103 - Modern Design, Bright & Clean, Concrete Floors, AC!
The new roof project will take place over the pool area from 7/18/25 to 7/27/25. During this time there will be noise and debris surrounding the building.------------------------------------From the front door, a magical stretch of Maui beach awaits your exploration -...
Hale Kamaole 121: Ground Floor Gem with Sunset Views & Resort Amenities!
Welcome to the highly sought after Hale Kamaole 121! This perfectly located ground floor unit offers beautiful sunsets and ocean views right from your lanai.As you enter you are greeted by the open comfortable feel of this beautifully updated condo. The kitchen has been...
Maui Resort Rentals: Honua Kai – 7 Bedroom Groundfloor Resort Residence, Over 4500 Combined Sq. Ft., Massive Lawn Area, Steps to Pools/Beach/B.B.Q.s
This package combines three adjacent ground-floor residences at the luxurious Honua Kai Resort to create a seven-bedroom masterpiece that is simply in a league of its own. Large families and groups are treated to the space of a luxury home with all the advantages of...
🏖️Private Ground Floor Corner Unit | AC & Ocean Views | vrKCV
vrKCV - Kona Isle D1, Professionally Managed by Kona Coast Vacations.Oceanfront Serenity at Kona Isle D1 – A Couple's RetreatEscape to Kona Isle D1, a modern one-bedroom, one-bathroom ocean-view condo, perfect for a couple's getaway on the Big Island of Hawai'i. Nestled...
Escape to paradise at Mauna Lani B208, an exceptional oceanfront retreat
Mauna Lani B208 Oceanfront Vacation Rental – 2 Bed, 2.5 BathEscape to paradise at Mauna Lani B208, an exceptional oceanfront retreat offering unparalleled luxury and breathtaking views. This stunning 2-bedroom, 2.5-bath condo is situated in one of Hawaii's most...
Glorious Beachfront, High End Villa, grass to sand, free parking
Prime beach front and ocean front location.Located in the Ocean Villas at the Ritz Carlton Resort, in a gated private community. Beach front, and by the pool, beach toys available, convenient and free parkingWe invite you to come and experience your tropical...
Gorgeous 3bd/2ba villa with huge covered patio, BBQ, koi pond & playground
Alas Del Kealoha is a luxurious large private gated (not fenced) house located in the heart of Volcano Village. This beautiful getaway home is a well illuminated 3 bedroom / 2 bath one-story pine house. Sleep up 10 to guests! 8 guests sleep on beds, 2 more guests sleep...
Villages 640 - Expansive Maile Floorpan with BBQ & Ocean Views!
Mauna Lani Villages 640 is a spacious & modern three bedroom two-story town home that can accommodate eight guests comfortably and includes plenty of lanai space with garden and distant partial ocean views located right in the middle of the exclusive Mauna Lani Resort....
Exquisite Oceanview - Kihei Surfside #310 - Your Gateway to Maui Bliss!
Kihei Surfside #310 – Breathtaking Ocean Views with Island Comfort and Split-Duct ACStep into the serene beauty of Maui with a stay at Kihei Surfside #310. This 1-bedroom, 1.5-bathroom condo offers stunning oceanfront views from the third floor and a comfortable...
Ocean/beach FRONT Ground FLOOR Spectacular VIEWS
Spectacular views, peace, tranquility and beautiful sunsets are found at Hoyochi Nikko 102. After a busy day of sight seeing, golfing, visiting beaches or whatever you choose to do during the day, this is the paradise you will come home to. This ground floor condo is...
Maui Resort Rentals: Honua Kai Hokulani 616 - 6th Floor 1BR w/ Partial Ocean & Mountain Views
Hokulani 616 is a wonderful 6th-floor suite offering views of both the blue Pacific Ocean and the verdant West Maui Mountains. A southern orientation offers abundant light as well as natural protection from the strong Maui trade winds.Suite 616 boasts an exquisite...
Top Floor Oceanfront Studio #311 W/LANAI and A/C
COOL A/C IS AVAILABLE when ocean breezes aren't enough.Unit # 311 - We have one of the few units in the building with an ACTUAL outdoor patio to enjoy the beautiful ocean view, which is direct ocean front, with famous Magic Sands Beach right next door! And with our COOL...
20% Fall Discount! Newly Renovated! Oceanfront & Pool Family Hideaway. Paradise.
Kalani Kai Beach House is a newly renovated, private gated oceanfront home located on one of the Waialae Beach Lots with a beautiful swimming pool nestled next to a sandy beach.The upstairs master suite has a king-size bed and panoramic ocean views from a spacious...
Pristine White Sand Beaches, in Waikoloa Resort
Kolea #16E is in the only beachfront complex in the Waikoloa Resort. NO RESORT FEES. Unlike other resorts, Kolea #16 does not charge any resort fees. This property is located on the famous Anaeho'omalu Bay, a 4 minute walk away through the Beach Club.Discerning guests...
Beachfront Beach Villas at Ko Olina O-501
Summary:Beach Villas at Ko Olina is about a couple miles stretch of coastline in this resort area. Four lagoon beaches that is shared with Disney Aulani, Four Seasons and the Marriott Vacation Club. But, the Beach Villas sits on "Honu" Lagoon which is basically...
Relaxing Hawaii Beach House
Located in a peaceful private community next to the sea, this newly-built home is perfect for those seeking a serene retreat. This home sits within walking distance of Kokololio Beach Park as well as a shopping center for essentials and popular local eateries. Venture...
Oceanfront, Palm Trees and the Beautiful Blue Pacific Ocean...Poipu Palms 202!
Palm trees and the beautiful blue waters of the Pacific Ocean greet you the second you open the front door of Poipu Palms 202.This is the beginning of your perfect Hawaiian vacation.Overlooking the powerful Pacific Ocean and the spectacular Poipu coastline, this nani...
KBM Resorts | FREE CAR | Mahana | Oceanfront | Stunning 2-Bedroom Condo! MAH-419
** 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...
10 Acre Private Bamboo Retreat Located Just Minutes From Volcano National Park
Lush 10 acre farm located just 15 minutes from the entrance to Volcano National Park and less than 20 miles from Hilo Town. A scenic drive south takes you to visit the turtles at Punaluu Black Sand Beach and South Point. Enjoy waking up to the sound of frogs, birds, and...
H-G-T-V type Renovation, Million Dollar view starting at only $210/night!
This unit was renovated by an HGTV interior designer and is virtually identical to another unit that was featured on the HGTV show House Hunters that aired in November 2013. Unit 109 offers the most luxurious accommodations for the best value. Unobstructed ocean view,...
Ku'u Lei Villa: Condo w/ AC, Shared Pool & Spa
Welcome to Kuʻu Lei Villa by Gather/Elite, your peaceful home away from home in Princeville, Kauaʻi. Nestled along the fourth tee of the Princeville Makai Golf Club, this elegant three-bedroom, three-bath townhome offers scenic golf course and mountain views, a...
Cliffside Home w/Gorgeous Ocean Views and Tropical Garden. Paradise Bluff
Paradise Bluff is a beautiful home perched on the cliffs of the small seaside town of Laupahoehoe. Relax, take a deep breath, and enjoy the Aloha spirit and traditions of the Big Island of Hawaii. Located on the spectacular Hamakua Coast between Hilo and Waimea,...
All New! Beachy Chic Remodel, Ocean front with AC
All new! Fully Air conditioned and decorated with a warm beachy chic vibe! Top floor, direct oceanfront.The spacious bedroom offers a new king bed. The living room has AC, new full size sleeper sofa, Smart TV, Free wifi New kitchen is fully equipped. Steps to the...
Amazing Direct Ocean Waterfront - 1bd/1ba Condo in Kahana Maui!
Come visit our spacious top floor corner oceanfront condo with fantastic views of Molokai and Lanai. You can watch spectacular sunsets and enjoy whale and turtle watching from your private lanai. Conveniently located between Kaanapali and Kapalua, our condo is ideal for...
Waipouli Beach Resort - Ground Floor #E103, 2 King Masters Suites
Aloha~Why should you stay in our ground floor unit? Pride of Ownership Shows! We have decorated our 1300 square foot unit with high end amenities~ Our unit shows like a model. Our unit features dual master suites opposite sides of the living room. The kitchen is simply...
Hawaiian Bungalow Steps to the Beach 1BR 1BA Ocean View with AC
Welcome to Hale Makani Aloha, a gorgeous 1 bedroom and 1 bath condo located conveniently just steps away from the longest stretch of sandy beach on the Island of Maui. Given our excellent location in the heart of Maui and just 10 miles from the Kahului Airport, you will...
Lanikai Hillside Cozy Cottage with Spectacular Ocean View with Mokulua Islands.
This beautiful hillside cottage with stunning ocean view offers the perfect getaway for a couple, small family, or up to four vacationers . Ideal for Military personnel transferring to or from O'ahu who need a month or several months rental. Bedroom has partitioned...
Spectacular Diamond Head and Ocean Views! Free Valet Parking, Wi-Fi, Pool!
Waikiki Beach Tower #3602 – 2470 Kalakaua Ave.This spacious, centrally air-conditioned two-bedroom, two-bath condo (1025 square feet plus large lanai with table and chairs) has one of the most breathtaking panoramic ocean views in Waikiki, plus an unobstructed Diamond...
Pua Oriana: A Polynesian Tropical Retreat
E komo mai — welcome to our hale. Welcome to the Pua Oriana – a mix of Hawaiian and Samoan language, ‘pua’ meaning flower, and ‘oriana’ means the flower that adorns a woman’s head. Enjoy the space and the grounds with 880 acres of pristine gardens, walking paths, golf...
500 feet to the 🌊, 1000 feet 🏝 and 🐢
The most incredible location, nestled among the trees and flowers, over an acre to overlook, and stunning sunsets, and the famous Poipu Beach is just steps away you’ll never want to leave our beautifully styled 1 bedroom, 1 bath condo. We have everything you’ll need and...
Chic Kihei Beach Retreat with Ocean Views across from Charley Young Beach
Our 2 bed, 2 bath unit has been remodeled, including a three zone mini-split A/C system, quartz counter tops, tile floors, open concept kitchen, and custom tiled showers. New stainless steel appliances, including full-size fridge, dishwasher & microwave, large capacity...
Papakea J405: Luxurious Ocean View Penthouse, 2 Min Walk to Beach, Many Updates!
Experience the ultimate Maui getaway at our top-floor penthouse condo, offering breathtaking ocean views and a plethora of amenities to make your stay unforgettable. Located just a 2-minute walk from the beach, this exquisite three-bedroom condo is perfect for families...
604 - Luxury Oceanfront - top floor unit with A/C and a spectacular ocean view!
*NEW* unit 604 now has air-conditioning! This upgrade will provide a more comfortable and cool environment for our guests! This sixth (top) floor oceanfront condo at the Kihei Surfside Resort is located on the sought after ocean side of the elevator, and has a...