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.
Lanai + Ocean Views: Secluded Holualoa Retreat!
Outdoor Dining | Fruit Picking On-Site | Short Drive to Snorkeling & BeachesSeeking a serene Hawaii escape? Look no further than ‘Lilikoi Inn!’ With stunning ocean views and a prime location just minutes from the shores of Magic Sands Beach, this 2-bedroom, 2-bath...
Kona coffee estate in Holualoa
Kona Coffee Estate Guest Apartment with Ocean and Garden ViewsOur estate is situated on the slopes of Mt. Hualalai on the Big Island of Hawaii. We are located just 15 minutes from the Kona Airport, 10 minutes from the quaint coastal town of Kailua-Kona, 10 minutes from...
Penthouse, 11th Floor, Sunset Side, Beach Tower, Panoramic Ocean View
Our unit in the Beach Villas at Ko Olina is located on the top 11th floor of the Beach Tower. The Beach Tower is one of two towers in the Beach Villas and is the one located closest to the water). The panoramic views of the water, sand beach, and even mountains are...
Direct Oceanfront Maui Studio,Romantic,Breathtaking View from Huge Private Lanai
Welcome to my Oceanfront studio, which is literally 50 ft to the water. Wake up to a breathtaking oceanview, take it all in from the spacious lanai, fall asleep to the sound of the ocean every nightRecently upgrade the TV to a 55inch Smart TV, which works w/ Apple...
ALA 38 Beautifully Renovated 3BD w/ Partial Ocean Views in Gated Oceanfront Community
Alaeloa 38 NEW LISTING Experience Your Next Amazing Family Vacation on Maui from this Newly Renovated Home in a Private, Gated Oceanfront Neighborhood!REE daily activities included with your stay value up to $1035! Complimentary admission, every day of your stay*:...
Create unforgettable memories in this Modern Family Friendly Villa in KoOlina!!
Choose to spend your days on the Ko Olina Championship golf course or at the Marina; relax at one of four breathtaking sandy lagoons, pamper yourself at the award winning Four Seasons Resort and Spa; spoil the kids at Au’lani Disney Resort or explore the rich culture...
1 bedroom at Honua Kai Mountain view remodeled April 2023 King Bed, Central AC
Fully remodeled in April 2023, this upscale and spacious one-bedroom retreat awaits you. Unit # is 626 on the 6th floor of the Hokulani tower. Enjoy all the amenities the Honua Kai resort has to offer, freshly prepared meals in your fully stocked kitchen and a cool,...
Luxurious Wailea Ocean Vistas
Summary:Completely remodeled (Dec 2022). Our new Wailea luxury condo is immaculate and offers direct ocean views. Airy, comfortable, and with stylish decor, every amenity a Maui visitor could hope for is provided. Guests will fall in love with Wailea's beautiful...
West Maui Ocean Front Resort Papakea Penthouse K-401 2Bed 2Bath with A/C
We invite you to experience one of Papakea's finest top floor, end units K-401. (Fun Fact: Papakea means crest of the wave in Hawaiian) This penthouse unit underwent a complete renovation in 2022. Each bedroom features a beautiful queen size bed with premium Purple...
Tropical Garden Condo with AC and pool
Spacious, ground floor condo on the famous north shore - Princeville. 2 bedroom / 2 bath, 1500 sq feet. Lush, tropical landscaping! Huge private wrap-around lanai with lush landscaping, 4 sliders & walls of glass. Mauna Kai has the largest pool in the area! Grill on...
Kaanapali Alii | 3102
Welcome to your tropical getaway at this one-bedroom vacation rental with partial ocean views, featuring two bathrooms and an inviting open floor plan with island-inspired design elements. This spacious condo comfortably accommodates up to four guests, making it perfect...
OCEAN VIEWS-EXCEPTIONAL NEW REMODEL-AC-GREAT BEACH ACCESS-METICULOUS CLEANING
Book with confidence, this stunning 1 bedroom, 2 bathroom condo at Kamaole Sands that was just remodeled as of December 2019. Everything in the condo is brand new and finished with high end materials that you would be hard pressed to find in a rental unit. This condo is...
4-bedroom mini-splits AC vacation home just 5 minutes drive to Wailea Beach
Discover the breathtaking Wailea area in Kihei and indulge in top-notch tropical life at this lavish four-bedroom holiday house. Nestled just minutes away from the pristine Wailea Beach and the vibrant Shops at Wailea, this property offers the perfect blend of...
Indulge in Luxurious poolside living: Ground Floor Condo in Waikoloa
Upgraded Ground-Floor Villa | Steps to Pool & BBQ | Walk to Shops & BeachWelcome to Waikoloa Beach Villas D2, a beautifully upgraded 2-bedroom, 2-bath ground-floor villa in a private gated community on the Big Island. Just steps from the resort-style pool, hot tub, and...
❤️PiH❤️ SLICE OF PARADISE ★Stunning Garden Views★Bikes
Brought to you by Paradise in Hawaii Luxury Homes.Welcome to Slice of Paradise Villa, a part of our Hawaiian Luxury Collection. Slice of Paradise at KaMilo is a wonderful 4 bedroom home (Mahina Model)We pride ourselves on providing some of the most sought after homes on...
Kiahuna Condo Unit 155 - A/C Living Room & Bed Room, Private, Perfect Location
Kiahuna Plantation Resort, on Poipu Beach, is one of the most popular destinations on Kauai. The property offers 35 acres of tropical gardens, lawns, and beachfront along with the famous South Shore sunshine. Kiahuna Unit #155 is a second story (top floor) one bedroom...
Hale Ho'okipa: 2 Homes / 2 Pools in Poipu - Sleeps 16
Gathering of the clan? Extended-family reunion? Or just an amazing shared adventure? Whatever the occasion, this beautiful 7BR/5+BA compound, with ample space for 16+ guests, offers blissfully comfortable accommodations for a large, congenial group. Two impeccably...
Escape, Relax, Renew 🌈 Hilton Pool Pass included!
Spring and Fall discount pricing during May and September!E komo mai! Welcome to the Big Island! Our spacious and updated condo is the perfect place to relax and enjoy all the amenities and adventures of the Big Island. Two bedrooms and two full bathrooms--one of each...
Enjoy the View - Listen to Nature - Hanalei Bay Villa #37
Views, Ocean, Sunset, Mountains, Jungle, Rainbows, Waterfalls, Views and Refreshing Breezes!Within the Hanalei Bay Villas, this individual family home is 'Haleakamanu' - the house of the birds. It is situated within walking distance of the luxurious Princeville Hotel...
Private Renovated Manoa Cottage
Go back in time to this renovated 1950's Hawaiian Cottage located in luscious Manoa Valley on the Island of Oahu. Lounge indoors on mid century Hawaiian koa furniture or outdoor on either the dining patio or the sitting patio. A short drive to shops, restaurants,...
Luxury Mauna Lani Home, Family Friendly, Golf, Private Beach Club, Walk to Shops
Deluxe Two-story Town House with Lanai Partial Ocean View, Triple Suites and Garage.We invite you and your loved ones to experience the vacation of a lifetime in our elegant yet comfortable island home. The Big Island of Hawaii is a magical place. You will fall in love...
Waikiki Shore 1114
"This tastefully decorated island suite is fully equipped with everything you need to have a fantastic Waikīkī vacation. With a stellar location, you’ll enjoy gorgeous views of the Pacific Ocean and Waikīkī beach from your furnished, screened-in lanai. You’ll...
Elegant Oceanview Villa w/Resort Pool, Spa & AC: Hali'i Kai 12C on Kohala Coast
This rare ground-level oceanfront condo at Waikoloa Resort places you in one of the most coveted spots on the Big Island. 2BD Hali'i Kai (12C) at Waikoloa Resort opens directly to sweeping Pacific views, brilliant sunsets, and the rolling green backdrop of the golf...
New Sunsets 2 kings 1st floor
Summary:Vacation of lifetime in this upgraded ground-level unit that blends modern design with an island vibe. Living room flows into a fully equipped chef's kitchen and opens to a lanai with stunning views of the golf course, lake, plaza, sunsets every evening. Beach...
Maui Resort Rentals: Honua Kai - 4 Total Bedrooms, 7th Floor Deluxe Ocean AND West Maui Mountain Views
This tandem one-of-a-kind 4BR offering combines one of Honua Kai's highly sought after deluxe ocean view 2BR corner suites with a neighboring 2BR. Your party will enjoy stunning 7th-floor direct ocean views in addition to views of the majestic West Maui Mountains. The...
❤️PiH❤️ Island Seabatical ★Private Pool★ Private Ohana Studio ★Free Hilton Passes
Brought to you by Paradise in Hawaii Luxury Homes.Welcome to the elegant home, Island Seabatical, a part of our Hawaiian Luxury Collection. Island Seabatical is a wonderful, new, large, single-level 3 bedroom, 3 bathroom home. The home includes a studio with its own...
Sophisticated, Luxurious...Best in West Maui
HALE MAHINA BEACH RESORT -- ROMANTIC BEACH FRONT GET-A-WAYRelax to the soothing sounds of waves and the caress of trade winds in a completely remodeled and impeccably decorated large corner unit at one of the most sought after beach resorts on Maui's prestigious west...
GORGEOUS OCEANFRONT PENTHOUSE
Completely renovated true oceanfront 3 bedroom (2 bedroom plus loft) 3 bathroom penthouse in Papakea unit F405. The view is phenomenal!!! There is absolutely nothing in between you and the ocean which is 50 feet away. Whale watching from the living room, the...
Kaanapali Ground Floor Renovated & 20 steps to the Ocean
Welcome to our tropical paradise at beautiful Papakea Resort. Our condo E106 is conveniently located on the ground floor with very close access to the ocean and the pool area in building E. This is a legally permitted vacation rental and hotel zone according to the...
Hale Nalu - Premier Beachfront 3br Home Steps Away from Baby Beach with Spa!
Hale Nalu is a roomy 3 bedroom, 3 bath home fronting the delightful Baby Beach and situated in a charming Poipu residential neighborhood. Spacious and appealing at 2,450 square feet, Hale Nalu features a beachfront master suite with Jacuzzi tub upstairs and a 2nd master...
Lodge at Kukui'ula Villa | 7
Look no further! This four bedroom villa at The Lodge at Kukui’ula on Kaua’i offer luxurious accommodations and exclusive access to the award winning private club facilities and amenities of The Club at Kukui’ula, including the 18-hole Tom Weiskopf designed golf...
40th Floor One Bedroom Condo
Newly developed and completed in Fall 2021, Azure Ala Moana makes the perfect home away from home. Perfect for long term stays- you'll have a spacious full kitchen with dishwasher, full size oven, and a washer and dryer in the condo, and a beautiful view of Sunset....
🌈 Sharing our Blessings! Spectacular Views, Sunsets, Whales, Rainbows🌈
🌈 Sharing our Blessings! Unrivaled Views, Sunsets, Whales, Rainbows 🌈Nestled on the picturesque Kahana Beach, our extraordinary property boasts stunning views of Molokai and Lanai. Experience the perfect blend of serenity and convenience as we are within walking...
Oceanfront ground level recent remodel at Kona Isle
Direct oceanfront, ground level, recently remodeled D4 at Kona Isle. Enjoy beautiful ocean views and breezes. Steps to the beachfront area with lounge chairs to relax in. Or swim in the solar heated pool. BBQ grills and picnic tables make for cooking out a breeze and a...
Emmalani Hale, High-end, Luxurious, Tranquil retreat, AC in Princeville
Welcome to Emmalani Hale, your perfect retreat in Kauai!More than just a vacation rental, Emmalani Hale offers a luxurious and welcoming island escape designed for relaxation and comfort. This beautiful 3-bedroom, 3-bathroom home with large spacious living space,...
Beautiful, Renovated, Hale Kamaole 159
Hale Kamaole 159 is ready for your ideal Maui beach vacation! It is a recently renovated, exceptionally clean, 1 bedroom, 1 bath condo located in beautiful Hale Kamaole with pools and tennis courts, and you're right across from Kamaole Beach Park III, where you can...
Stylish Waikiki 1 Bedroom Gem with Parking
30-Day Rental Only!Kick back, relax in this stylish, newly remodeled space in quiet Waikiki. Charming 1-bedroom apartment featuring fully-equipped modern kitchen and bathroom, and air-conditioned bedroom for restful nights. Perfect for solo travelers or couples with...
The Best Condo in Wailea Ekahi Village!
Wailea Ekahi Village is a tropical oasis that sits right on Ke'awakapu Beach, considered by locals to be Maui’s best beach. Surrounded by major resort hotels, shopping centers, and championship golf courses, it's a vacationer's dream! This condo is in one of Ekahi...
Enjoy garden views and ocean glimpses from your private lanai at #138
Location! Location! Location! Who needs a car?!? This central Wailea location makes it favorable as you can find tennis, golf, retailers at the Shops at Wailea, casual to fine dining restaurants, world's top beaches, and five-star hotels just moments away.Kick back and...
*25% Off-Steps to Beach-AC in Every Room-Remodeled
🌟 COMFORT AND ELEGANCE COMBINED 🌟Step Into A World Of Contemporary Elegance With This Modern Remodeled Condo. Honus Hideaway Is Thoughtfully Designed To Provide A Comfortable And Luxurious Stay. The Condo Is 880 Square Feet. It Features Two Cozy Bedrooms With...
Wyndham Bali Hai Villas | Three 2BR/2BA Villas!
Summary:This listing is for three 2BR/2BA suites at Club Wyndham Bali Hai Resort in Princeville, HI. Live Suite guests will have access to all resort amenities. Each suite sleeps up to 6 guests. - Photos are stock photos provided by the resort. Your suite may vary...
Ocean Views | Polo Beach Club Ground Floor Condo | Walk to Beach, Private Patio
Summary:Escape to paradise at this ground-floor condo at the exclusive Polo Beach Club. Enjoy stunning ocean views, lush gardens and direct access to Wailea’s premier swimming beach. The “endless lanai” allows you to step straight onto the pool, beach or scenic...
Kaanapali Shores 702 Find Your Next Summer Escape at Beautiful Beachfront Condo
The Stice Team — Powered by Gather Vacations. Maui Born and Raised Professionals. Your Local Experts in Crafting Unforgettable Stays.Welcome to Kaanapali Shores 702, a show-stopping direct-oceanfront residence perched on the 7th floor of the acclaimed Kaanapali Shores...
Location - Location - Location: FULLY RENOVATED @ TBR: 1xBR/BA/PRK - WiFi/AC
*Gutted to Gorgeous: everything new* - JAN 2025: FULL Renovation - *Professionally Sanitized: always glistening clean* - New kid on the TBR block - you’ll feel the Aloha - TBR: 1 Bedroom/1 Full Bathroom/ 1 Reserved Parking - Perfect get-a-way w/ sandy beach cove -...
Kaanapali Alii | 3112
Condo 3112 is a one-bedroom condo with a sleeping den and beautiful views of both Kaanapali Beach and the West Maui Mountains. This condo is a good choice for two couples traveling together as the sleeping den includes a queen bed and its own bath with a walk in glass...
Beautiful View • Close to Beach and Close to Town
This is a Hosted Property. Recently constructed and fully remodeled 700 square foot self-contained living space in a private, separate wing of the house. The bedroom and living areas are filled with light, looking out to gorgeous views of the three mountains - Mauna...
Papaya & Palm - A Private Tropical Oasis
Come and relax in this private guest home on the western slope of Mauna Kea, Hawaii's oldest dormant volcano. Centrally located and just 15 minutes from the island's best white sand beaches and renowned resorts, this space makes the perfect home base for all your Big...
Charming 2bd split-level in garden setting
Welcome to Maui Kamaole M109, a tropical paradise nestled in the heart of Maui's beautiful South Kihei region. This delightful property offers the perfect combination of comfort, convenience, and island charm. Step into this enchanting ground floor 1-bedroom, 2-bathroom...
Spectacular Urban Location - A Peaceful Surrender in Waikiki
This privately owned unit at the newly renovated Aqua Palms Lifestyle Hotel offers a serene escape with stunning mountain and city views. Located across from the world-renowned Hilton Hawaiian Village Hotel, you`ll enjoy easy access to the Duke Kahanamoku Lagoon, weekly...
"Hale Maluhia" - Cottage with expansive ocean views in central Kailua Kona.
Enjoy our hosted private 1 bedroom, 1 1/2 bathroom accommodations. Beautifully detailed with a king size bed, tv, wireless internet, laundry, closet, and large covered lanai. Everything my mom needs for her month long stays with our family!The large lanai (covered deck)...