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.
Cottage with Amazing View, Minutes to Dolphin Swimming, Very Private, Affordable
Please check out the main house on the same property for larger groups:vrbo 1542506This cottage is perfect for a couple looking to save money but still have a million dollar view. In Kealakekua Bay, just 3 minutes from some of the best snorkeling and wildlife viewing in...
Mahana 1215 Penthouse
This one bedroom two bath condo is located at the Mahana on Kaanapali Beach, once inside you will enjoy million dollar views of the Pacific Ocean which face West for sunsets you will never forget. Don't miss whale season as you will have the best location on Maui to sit...
Private Corner Unit with Spectacular Ocean Front Views
Aloha! Come and enjoy Hale Ho’ola. Our “House of Healing”, situated atop a bluff overlooking the beautiful blue Pacific is a corner unit so private, that it feels like you are the only ones there! Surrounded by the beautiful sights and sounds of the ocean along with the...
Beautiful Kealakekua Home w/ Spectacular Ocean View
Located approximately 10 miles south of Kailua-Kona is your Hawaiian home while visiting visiting us here on the Big Island of Hawaii. Arise in the morning and enjoy a freshly brewed cup of Kona coffee while planning your adventures for the day. You are just minutes...
Hilton Waikoloa Pool Pass thru 2025. Waikoloa Golf Discounts! J2 Waikoloa Beach
This vacation rental is professionally managed by ResorticaHawaiiWaikoloa Beach Villas J2Please scroll down for detailed informationHilton Pool Pass: Valid for stays now through December 31, 2026. Maximum 6 persons per pass (children under the age of 5 are not counted...
Oasis Kona: Luxury Ocean View peaceful Home with Pool, Spa & Outdoor Shower
Welcome to Oasis Kona, a beautifully curated ocean-view home for your perfect Hawaiian vacation. Relax by the pool, enjoy the spa & heated outdoor shower, and take in unforgettable sunsets. With an open floor plan, lush gardens, and a private setting, you’ll feel at...
Mountain View Retreat Unit 1 - highly rated on leading rental sites!
Peaceful rain forest guest house a few miles from Volcano National Park. Mountain View Retreat is located in a lush and relaxing paradise. Enjoy your coffee or tea in the morning on your own private lanai. For larger parties there is another guest house on the same...
Nestle Into Your Private Cottage After a Busy Day. Enjoy the Hottub - Permitted
Maui County Rental permit - STPH 2013/0024TA-091-083-1616-01TMK-270031060000Fabulous views, privacy and quiet were foremost for us in choosing where to build our dream home in Hawaii. We looked for several years before finding this special Maui hilltop location on the...
Sunset Golf Course Views from Lanai with Outdoor Kitchen!
Enjoy all the best that the Big Island has to offer!! Our beautifully Hawaiian furnished home at the Waikoloa Beach Villas - a luxury gated community at the Waikoloa Beach Resort - is conveniently located across the street from the King's Shops and Queen's Marketplace....
KRV 1723 Remodel 3BD Kapalua Villa w Ocean View
Kapalua Ridge Villas 1723 NEW LISTING Rare 3Bedroom, 3Bathroom Remodeled Ocean View Villa in Beautiful Kapalua, Maui! Discover the perfect blend of luxury and comfort in this rare, remodeled 3-bedroom, 3-bathroom condo at the Kapalua Ridge Villas. This spacious...
Polo Beach Club 409 - 2 Bedroom Oceanfront Condo
Polo Beach Club 409 is a luxurious oceanfront vacation rental located in the world-renowned beach vacation destination of Wailea. This two-bedroom, two-bathroom condo offers a premium beachfront experience with direct access to Polo Beach out front and stunning ocean...
Spectacular Oceanfront GEM!
Brand new fully remodeled Lahaina Gem! This stunning 2 bedroom 1 bath condo is where it’s at! Get the feel of old hawaii with a classy modern twist. We also provide snorkeling gear, body boards, beach chairs, beach towels, and new air conditioning. The Condo is ground...
Maui Family Owned & Managed - Wailea Grand Champions Villa
Located on the world-class Wailea Blue Golf Course. Our Wailea Grand Champions condo has been newly redecorated and furnished with decor that depicts the beauty of Hawaii and our rich Hawaiian culture. As a local family who live on island, we are able to actively...
Wailea Grand Champions 152 - 1 Bedroom Golf Course View Condo
Relax on your private lanai at Grand Champions #152, perched upon the second-floor, and enjoy views of manicured fairways, putting greens, and tee boxes as golfers tackle the Wailea Golf Course. This vacation rental is ideally situated to showcase Maui’s natural...
Aqua Aloha Surf Waikiki 402 Superior Studio with Lanai and Partial City Views
Aqua Aloha Surf Waikiki 402 Superior Studio with Lanai and Partial City Views located just 2 Blocks to Waikiki Beach, (1) King bed, Sleeps 2, 335 Sq Ft.Aqua Aloha Surf Waikiki offers a range of accommodations that are perfect for couples and solo travelers. On-site...
Spectacular Ocean and Golf Course Views! Luxury Home with Separate Guest House ** 2 Golf Carts**
Spectacular Sweeping Views from this Four Bedroom Luxury Home with Separate Guest House is Paradise Perfected. Located on the #16 Fairway of the Hualalai Golf Course, this luxury home is recently redecorated by Willman Interiors, and boasts beautiful furnishings, an...
Hanalei Bay Resort 4301: Oceanview w/ Lanais & Resort Perks, Pools & Tennis
Welcome to Hanalei Bay Resort 4301 by Gather, a serene one-bedroom, one-bathroom condo perched above Kauaʻi’s breathtaking North Shore. Overlooking Hanalei Bay and the lush Na Pali Coast, this peaceful island retreat is perfect for couples or solo travelers seeking...
Koi Palms 1 bedroom Cottage - Great location! 5 Minute Walk to Kailua Beach!
Come and enjoy our island home with us. Koi Palms Cottage is located within our gated property alongside our lovely Koi pond, in the quaint town of Kailua. The owners live on the property in the main house.The cottage is a 600 square foot 1 bedroom unit. The kitchen is...
Alana by the Waves - Oceanfront Home in Napili
Stunning Oceanfront Retreat in Napili, MauiPerched above a secluded bay and wrapped in lush tropical greenery, this private oceanfront home is a true Napili gem. Enjoy sweeping, unobstructed ocean views and a rare sense of seclusion that makes it feel like your own...
Comfy Surf Studio 2 Blocks From The Ocean
This comfy and clean Surf Studio is located 2 blocks from the beach and Ali'i drive where all the best attractions are such as tasty restaurants, fun retail shops, bars, coffee and smoothie spots, fresh farmers markets, Magic Sands Beach, and much more. This relaxing...
WOW! "BEST IN CLASS" POSH NEW REMODEL! 2 BR/2 BA-SLEEPS 9 - 6 BEDS-Great Views!
Unit F-202 is the ABSOLUTE NICEST "fully remodeled" CENTRAL AIR CONDITIONED unit at the relaxing Kaanapali Royal condominium resort. ...And reasonably priced !!! This very quiet unit has wonderful Ocean, pool & Hawaiian landscaping views. The "partial ocean view" can be...
Poipu Bay Getaway - Poipu House - Saltwater pool, hot tub, AC!, Walk to Beach and Hyatt!
Spacious 6-Bedroom Villa with Saltwater Pool, Hot Tub & Prime Location. Welcome to Poipu BayGetaway, your ultimate island retreat on Kauai’s sunny South Shore. Just350 yards from the beach and a short walk to the Grand Hyatt Resort, thisluxurious 6-bedroom, 4-bathroom...
Maui Budget Condo with Oceanfront Luxury at Papakea
** Please review the note at the bottom of this section for detailed rate information. **For an overview of Papakea Resort check out: https://www.youtube.com/channel/UChREir40cH28E7foXaSMBkAThis Papakea condominium has a commanding ocean view of Molokai and Lanai. You...
Stunning ocean view 2 bedroom • Steps from beach
Enjoy beautiful ocean & sunset views from, Ohana Lani, a 5th floor condo with 1120 sq of living space and a stunning double wide lanai. The condo artfully blends modern amenities and island style. Ideally located in Kihei, the unit is right across the street from the...
Hilton Pool Pass thru June 2025 and Golf Discounts. Waikoloa Colony Villas 1002
This vacation rental is professionally managed by ResorticaHawaiiWaikoloa Colony Villas 1002Please scroll down for detailed information.Bedding Configuration:Master Bedroom: King BedGuest Bedroom: King BedGuest Bedroom:Queen BedAdditional Bedding: Sleeper Sofa in Living...
Ko Olina Beach Villas O1402: Spectacular 14th Floor Penthouse w/Ocean Views
Welcome to Ko Olina Beach Villas O1402 by Gather, a 14th-floor penthouse where sophistication and comfort meet Hawaii’s natural beauty. Overlooking the Pacific Ocean and Ko Olina’s tranquil lagoons, this luxurious three-bedroom, two-and-a-half-bath villa accommodates up...
Removed Trees=stunning ocean sunsets,@Wailea Beaches, Green, and Foodie Kitchen!
To enjoy our GORGEOUS OCEAN VIEW, from our upscale, VERY GREEN, very sound proof, 2 Bedroom, 1 and 1/2 Bath Condo, just a 4 minute walk to the nicest Beach on Maui, Keawakapu. Just book it here! Take a nap or read a book looking out on lawn, woods, and ocean as the...
Kamaole Sands -Inner Court-Extra Large Lanai-Ocean & Garden Views
Aloha!Quick note: --We also own another Maui Condo & Sunriver Oregon Vacation Properties, see below for VRBO #'sWe invite you to escape to our newest place in paradise. We now have something for everyone at Kamaole Sands. We also own a 1 Bdrm/2 Bath condo at Kamaole...
HOL 104 Poolside Condo at OceanFront Resort
Hale Ono Loa 104 Poolside Ground Floor 1Bedroom Condo at Oceanfront Property in West Maui. Updated, Spacious and Clean for a Fun Quick Getaway or Much Needed Vacation FREE daily activities included with your stay value up to $570! Complimentary admission, every day of...
Coconut Plantation 1086-4: Elegant 3BR Ko Olina Townhouse w/ Fairway Views
Set along the 11th fairway in Ko Olina Resort, Coconut Plantation 1086-4 by Gather is an upstairs townhouse villa where island ease meets resort convenience. Contemporary Asian-inspired decor, a breezy covered lanai, and views of swaying palms create a tranquil home...
Beautiful Custom Eco Friendly Home with Private Back Yard POOL
Beautiful furnished plantation style truly custom home on sunny Kaloli point in Hawaiian Paradise Park. We are a legal short term rental with the state of Hawaii. Also eco friendly as the entire house and pool is solar powered with the exception of our gas stove! 15x30...
Prime ground-floor location with many extras
Papakea B102 is a 1-bedroom, 1-bathroom condo featuring amenities such as a washer/dryer, 1 window air-conditioning and more! The condo can accommodate up to 4 guests with a California King-size bed in the bedroom and a queen sleeper sofa in the living space. The...
Magnificant Condo in Paradise. New mini split air condioners. Unit A208
Welcome to the sunny side of Maui! Our 2 bedroom, 2 bath condo is exceptionally large, approximately 1050 sq. ft. with a terrific Kehei location. Restaurants, shops, and beaches are easily walked to within a matter of minutes. Haleakala Shores is a smaller condo complex...
Kaanapali Alii | 384
Kaanapali Alii 3842 Bedrooms | 2 Bathrooms | Sleeps 8 | Ocean View________________________________________The phrase “modern elegance” perfectly describes platinum-rated Kaanapali Alii 384. Clean white walls, tiled floors, and cream-colored furnishings are paired with...
Dreamy Puako Beach House on White Sand Beach with AC!
Absolutely stunning 3 bedroom/2 bath beach house. Hale Laʻi Laʻi ~ Home of tranquility and contentment. Recently remodeled to create a feeling of contemporary elegance and relaxation with total beach vibes. Everything has been upgraded with soft modern finishes...
A/C - Blue Ocean - Mountain & Waterfall Views
This air conditioned island gem is set atop the Jungle Valley. Sit back and take in the stunning Mountains, Waterfalls and partial Ocean Views. Take a stroll and sit on the nearby grassy bluff to watch migrating whales when in season. Experience the symphony of tropical...
Kona Bali Kai 213 – Oceanfront Condo–Private Lanai
Wake up to the sound of the waves on the shore. This 2-bedroom condo looks directly over the Pacific Ocean, offering a waterfront retreat unlike any other. The spacious lanai gives you a private place to relax and enjoy the views. Inside you’ll find a relaxing space to...
Maui Resort Rentals: Honua Kai Konea 543 - Expansive 5th Floor 2BR w/ Fantastic Ocean Views
Konea 543 is a gorgeous oversized 1315 sq ft 2 bedroom oceanview villa with three king-size beds that affords а perfect opportunity for a grounp of six to gather and celebrate or just have a relaxing time! Its 5th-floor location offers beautiful ocean and pool views....
Spacious Home In Kahala That's Centrally Located w/AC, Pool, Lanai 5BR/4Bath
Minimum rental period of 30 days, Rental included Electric, Water, Cable WiFi Clean the yard twice a month and clean the swimming pool every Tuesday and FridayUpscale neighborhood of Kahala that is walking distance to Kahala Mall. It's about a One mile drive to the...
Princeville Queens Bath House - 100 steps to Trailhead
Our house was designed to be the ultimate family vacation house. It has a 29' pool and exotic tropical hot tub with waterfall ! You'll love the fully opening sliding glass lanai doors, bringing the island style open feeling from the great room to the outdoor lanai -...
🏖️Spectacular Ocean Views | Beautiful Landscaping | Private | vrKCV
vrKCV - Puuwai Alii Place, Professionally Managed by Kona Coast VacationsPu'uwai Villa is on a landscaped half-acre on a private road with plenty of off-street parking.Private, very quiet, one of only six homes on the private road. A large open space forest borders the...
Experience the best in Waikiki, while staying in our "Halona" Suite.
This centrally located studio at the Marine Surf, comes with free, assigned parking and features all the essentials for a comfortable stay, including a fully equipped kitchen, private lanai, and convenient amenities.Just steps from world-class beaches, shopping, dining,...
Rare Single Level 2 Bedroom-Spectacular Ocean Views-Ac-Meticulous Cleaning
Book with confidence, this beautiful over sized, 2 bedroom, 2 bathroom condo that has stunning ocean views. 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 available...
5 Minutes to the Beach! Oahu Ocean View + Family retreat
☆☆☆ Why guests LOVE our home? Why guests find it such a great VALUE?- Free parking for 5 cars (save $40–$100/car nightly)- Private SPA & BBQ in backyard, full kitchen to cut dining costs, - Spacious single-story for large family with senior and kids, 3 bedroom, 9 beds...
New Waikiki Boutique Condo 1.5 blocks to the sands of Waikiki Beach!
This boutique condo is just 1½ blocks to the pristine sands of Waikiki Beach! Newly renovated studio with a fully equipped kitchenette, and beautiful mountain/city views from the private lanai. The ideal location and beach themed decor make this vacation retreat one you...
Paradise found! 3 bedroom home with large lanai, AC and 2 blocks from the ocean
Your Pāhoa adventure begins at this 3-bedroom house with air conditioned bedrooms and downstairs studio. With two bedrooms upstairs (king in primary bedroom with en suite bathroom and a guest room with a queen bed and separate bathroom) and a studio downstairs (king...
Kona Coast Original Beach Boys 9.5 acre Estate, Pool and Amazing Ocean Views
Kona recalls the Beach Boys playing their pop hits by the pool. The band left but the good vibrations linger. Situated on 9.5 gated acres, gated for with an amazing Hawaiian plantation-style home with separate sleeping quarters and a guest house. Pool hot tub, gas...
NEW!! Iconic Hawaiian Getaway at Mauna Lani. Beach, Bike, Golf, Books, Relax.
Parking Pass to Mauna Lani Beach Club Included.Welcome to the Surf House in picturesque Kulalani, a gorgeous, upscale community within the world-class Mauna Lani Resort. This charming, light-filled two-bedroom townhouse is your perfect Hawaiian escape. Featuring soaring...
This apartment is a 1 bedroom(s), 1 bathrooms, located in Honolulu, HI.
Welcome to our "Plumeria Suite" - A vibrant, stylish apartment, with fully stocked kitchen, located in the iconic Ilikai. Very short distance from the Pacific Ocean, Duke's Lagoon, Magic Island, Ala Moana Center and an abundance of shops and restaurants.• Complimentary...
Ground-Floor Ocean View W/Lanai–Kaha Lani #105
Castle Kaha Lani Resort #105 on the ground floor: Set on the ground floor with ocean views, this one-bedroom/one-and-a-half-bathroom condo features bright and airy interiors with oversized windows. Calm earth tones, ornate finishes, and pops of tropical-colored patterns...