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.
Honolulu Luxury Condo w/ Resort Amenities & Private Courtyard Access
Welcome to Elevated Island Living at Sky Ala Moana West. This property can be rented for 30 nights or longer.Experience the perfect blend of luxury, comfort, and indoor-outdoor island living in this one-of-a-kind residence at Sky Ala Moana West. With soaring 12-foot...
Lanikai Ola Nani: Majestic Retreat, Close to Beach, Designer Details, Views!
Lanikai Ola Nani by Gather is a refined island sanctuary just steps from the sands of world-famous Lanikai Beach. This four-bedroom, four-bathroom retreat combines designer renovations with indoor-outdoor flow, creating a private haven for monthly stays in Kailua’s most...
Luxurious retreat at KaMilo in the Mauna Lani Resort
Welcome to Moana Ohana, your luxurious retreat at KaMilo in the Mauna Lani Resort. This exquisite four-bedroom home is nestled within a premier gated community and offers over 2,400 square feet of living space, perfect for families or groups seeking a memorable Hawaiian...
kaanapali-alii-unit-174
Kaanapali Alii 1742 Bedrooms | 2 Bathrooms | Sleeps 4 | Ocean View________________________________________Welcome to Kaanapali Alii 174, a charming two-bedroom ocean-view residence that perfectly captures the spirit of Maui. This inviting retreat combines the comfort of...
𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢 Beachfront Maui Ocean Club Resort+Amenities. 1BR Condo
Welcome to 𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢 🌴🌺 Ideally located in the heart of Kaanapali Beach along the famous Kaanapali beachwalk. It is right next to Kaanapali Point and mere minutes from the shops and restaurants of Whaler’s Village.Additional $500-$1000 SAVINGS available for 𝐅𝐢𝐧𝐝𝐢𝐧𝐠...
New Luxury Oceanfront Condo ★ Amazing 180° Ocean Views ★ Top-Floor Corner-Unit
Kana'i A Nalu 417 by KNOWLES MAUI• Recent full-condo remodel, new everything• Top-floor corner unit with unobstructed ocean and outer island views• Freshwater beachside swimming pool • On Sugar Beach – the longest beach in Maui, great for swimming, snorkeling, boarding...
Marriott's Maui Ocean Club Lahaina Villas Beachfront Resort!
Marriott's Maui Ocean Club - Lahaina Villas is one of the most popular timeshare resorts - and for good reason! Kids and kids-at-heart will get a kick out of the resort's 3.5-acre super pool complete with a water slide, waterfalls, and children's area. The poolside bar...
Kapalua Golf Villas | 2 Free Rental Cars | KBM Resorts | Large Bedrooms | 2 Units, 3 Bedrooms | KGV ML-2102
** 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...
Charming 1-bedroom apartment in tropical Kaneohe with WIFI, AC
Fully furnished High-End whole level rental, with separate entry. Renting 180+ days, long term rental. All furnishing is new and 2 new AC.Bedroom, living room, designer kitchen, modern bathroom, and spacious lanai. Includes own laundry room with brand-new full-size...
Kaanapali Maui Eldorado K111 Garden View Studio
Surrounded by greenery and steps from the sand, this Maui garden-view studio blends comfort with location. Enjoy peaceful mornings with a quick walk to the beach, and all the essentials for a restful retreat for two. Unit K111 Garden View Studio• Located in Building K...
Spacious Renovated 4bd - Koa Resort 2A
Welcome to your perfect vacation retreat! Recently fully renovated, this beautifully appointed 4-bedroom, 3-bath townhome offers serene comfort and a beautiful modern remodel that showcases the Hawaiian charm of the complex. With all-new furniture, bedding, and modern...
Ala Moana Hotel 24th FL R0 Ocean View 2 Double Beds
Welcome to Ala Moana Hotel Partial Ocean unit 24** Recently Renovated last May 2025. Enjoy and relax with our revamped studio unit that can accomodate 4 Guests. Centrally located with NO Hotel Fees! Ala Moana Hotel offers the ultimate convenience with direct access to...
cuzy Kaapuni
This (2) bedroom, 1 bath property is conveniently located just minutes away from highways, beaches, and stores. Find out more about this desirable location and all it has to offer Enjoy convenient access to all your favorite destinations while enjoying the comforts of...
2-Bedroom Condo in Charming Princeville. AC. Sleeps 6. Pool, Hot Tub Fitness Rm
Located in the heart of Princeville, This condo is a dream. Air Conditioned 2-bedroom 2-bathroom condo which includes a master bedroom/bathroom, king bed and Lanai right off the Master Bedroom, a guest bedroom with a queen size bed and a double twin size bunk bed....
Steps Away from Kalapaki Beach! Onsite Parking, Pool, Beachfront Location!
This listing is for a room within a hotel.✦ Your room is 452 sq. ft, equipped with complimentary toiletries, standard quality TV, available with Standard cable.✦ Cleaning services availability and frequency vary by stayThere are a few additional details to know before...
Lodge at Kukui'ula Villa 10
Welcome to Lodge at Kukui'ula Villa 10, your private island retreat on the sunny south shore of Kaua‘i. Blending laid back elegance with modern comfort, this four-bedroom villa offers a serene escape surrounded by the beauty of Hawai'i's lush landscape, sparkling ocean,...
NEW! KBM Resorts | FREE CAR | Mahana | Oceanfront | 2-Bedroom Condo with Beautiful Nightly Sunsets! MAH-109
** 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...
Lux Ko Olina B609 & B610: 4BR Oceanfront Villas w/ Lanai & Views
Ko Olina Beach Villas B609 & B610 by Gather is a rare 4-bedroom, 4-bathroom oceanfront retreat that sleeps up to 12 guests. These adjoining sixth-floor villas offer sweeping views of Ko Olina’s 2nd Beach Lagoon, two gourmet kitchens with Sub-Zero and Wolf appliances,...
Remodeled Awesome View Waikiki Studio with Full Kitchen
This beautifully remodeled corner studio on 35th floor of Hawaiian Monarch is the perfect place to enjoy your Waikiki vacation! With awesome views of Diamond Head, Ala Wai canal, ocean, mountains and the city, this condo has it all. Guests can specify if they want one...
Spacious 2BR Condo w/ Balcony by Kihei Beach
Gather your loved ones and unwind in this spacious 2-bedroom condo at Maui Schooner Resort in Kihei. With a full kitchen, A/C, and a private balcony or patio, it’s perfect for families or friends. Enjoy nearby beaches, a refreshing pool, hot tubs, and BBQ areas. Whether...
Remodeled Ground Floor Condo - Papakea Resort C108
Remodeled with garden views on the ground floor in North Ka'anapali. Walk out into green grass under your feet and take a short walk past koi ponds and putting greens to the pool and Jacuzz and the Ocean. A beautifully updated kitchen allows for cooking family meals in,...
Maui Resort Rentals: Honua Kai Hokulani 513 - Premier 5th Floor Interior Courtyard 1BR w/ Gorgeous Ocean Views!
Located in the only 1BR column of interior courtyard facing suites at the entire Honua Kai Resort, Hokulani 513 is uniquely positioned to offer guests incredible views of the turquoise-hued Pacific Ocean and Maui's neighboring island Molokai from its 5th-floor vantage...
Honua Kai Resort View 1 Bedroom + Den
1 Bedroom Resort View with Den - Exclusive on-site provider with the only homes meeting the prestigious AAA 4-Diamond designation- In addition to a separate bedroom, this suite has a separate den area- Picturesque views that include the beautiful landscaped grounds,...
Honua Kai Piilani Suite 3 Bedroom
3 Bedroom Piilani Suite- Exclusive on-site provider with the only homes meeting the prestigious AAA 4-Diamond designation - 1 king bed in each bedroom and a queen sofa sleeper in the living room; Open floor plan 2,300 Sq. Ft.- 3rd guest bed can be split into two twin...
20th Fl Waikiki Banyan | King | AC | Parking
The SpaceEnjoy the newest accommodations at Waikiki Banyan in this beautifully renovated 20th-floor suite. Fully updated in August 2025, the unit features brand new modern furnishings, upgraded fixtures, and stylish décor. With partial ocean views, bright natural light,...
Royal Sea Cliff Kona 602 Ocean View 1 Bedroom
This ocean view one-bedroom condo sits on a lava rock bluff near Kailua-Kona, offering striking views and tranquility. It’s a serene retreat close to beaches, dining, and local attractions. Unit 602 Ocean View 1 Bedroom 1 Bath• 6th floor condo located on south side of...
Lahaina Shores 515 Oceanfront Studio with Lanai, Sunset & Island Views
Lahaina Shores 515 Breathtaking Ocean and Sunset Views from this Beautifully Remodeled Studio Condo Just an Elevator Ride from the Beach, Pool and Hot Tub Welcome to your Maui Retreat: Wake up to the soothing sounds of the ocean at Lahaina Shores 515, a remodeled 5th...
Christmas Week Roomy 3 Bdrm Beachfront Villa Nanea Resort Sleeps 12
Ocean Front 3 King Size Bedrooms and King Size Pullout Sofa during Christmas Week and the Brand new NANEA Westin Resort. Sleeps 8 with additional rollaways if room for 1 or 2 more needed. Relax in luxury and comfort at a resort with all the amenities in Maui. This brand...
Lux Makakilo Hale by Gather: 5BR Retreat w/ Private Pool & Ocean Views
Perched high above Kapolei on O‘ahu’s sunny west side, Makakilo Hale by Gather offers a private hillside escape blending modern design, panoramic views, and relaxed island luxury. With 5 bedrooms, 2.5 baths, and a resort-style pool, this expansive retreat is perfect for...
Lagoon Waterfront Retreat
Escape to the quiet community of Paiko Lagoon on Oahu's South Shore. This duplex single story home is the perfect getaway with the right mix of modern and beach. Very private with separate entrance and keypad entry. Enjoy watching the sunrise from your bed over the...
Upscale 3BR Luana Waikiki Suite • Sleeps 6 • Walk to Beach
**Free Parking** (parking in Waikiki hotels can be around $70/night)Welcome to your home base in paradise at the Luana Hotel in Waikiki – a modern, 3-bedroom private residence suite that comfortably sleeps up to 6 guests. Located just a short walk from Waikiki Beach,...
Beautiful Ocean View Condo, Near Beach + Parking
Aloha from Midway Vacations! Our team of local hospitality experts is dedicated to turning your Hawaiian getaway into a reality. When you stay at one of our properties, you can count on a professionally cleaned and meticulously maintained experience. We're even...
1BR Oceanview Condo w/ Pool & Balcony in Kihei
Retreat to this oceanview 1-bedroom condo at Maui Schooner Resort in Kihei. Enjoy modern comforts like air conditioning, Wi-Fi, a full kitchenette, and a private balcony or patio. Whether you're sipping coffee with sunrise views or relaxing after beachside adventures,...
Cozy Beachfront Waianae Condo Oahu Hawaii Close to Disney Ko Olina & Waikiki.
Unwindw in our stylish 1-bedroom condo where tropical serenity meets modern comfort. Just steps from the ocean, enjoy stunning views and fall asleep to the sound of waves.Swim in a semi-private lagoon, spot whales from your balcony in winter, or snorkel with sea turtles...
Royal Kahana Maui 315 Ocean View 1 Bedroom
Unwind in your comfortable one-bedroom with beautiful ocean views, just minutes from sandy shores. Ideal for families, friends, or beach enthusiasts. Unit 315 Ocean View 1 Bedroom 1 Bath• 3rd floor condo with nice ocean views • Kitchen includes microwave, stovetop/oven,...
🚐 Skip the hotel — 🏕️ Camping Experience — 🤑 Budget Friendly Vacation! 🏝️
Embark on a camping experience in Hawaii with our minivan camper perfect for individuals or couples.**Located in Kailua!! It's a 25 minute Uber/Lyft from the airport.CAMPING GEAR INCLUDED:â–º 8" Memory Foam Mattress with CLEAN FRESH sheets â–º Solar Powered Rechargeable...
Lihue Kauai 1 Bedroom Sleeps 4
Please Send An Inquiry Before Requesting To Book By Clicking The Contact Host Tab.The 1 bedroom condo which is located only two miles from the Lihue Airport, is centrally located on the island of Kauai. A short five-minute walk will take you to Kalapaki Beach. The...
Just Renovated- Minutes to the beach. Perfect for long stays!
Be one of the first to enjoy staying in our beautiful one bedroom condo, just a couple blocks to world famous Waikiki Beach. Newly renovated in Spring 2023, you'll find a full stocked kitchenette to enjoy preparing meals in, a brand new walk in shower, and a bedroom...
Skyline Island Stay • Two Adjoining Studios
Located on the 35th floor, this spacious 2-bedroom, 2-bathroom unit offers stunning views of the Ala Wai Canal and Manoa mountains. What makes this place unique is the incredible panoramic views combined with generous living space. We feature 2 fully stocked kitchens...
Oceanfront Bungalow with Gated Entry and Pet Friendly
A classic single-story, semi-renovated, beach cottage just steps from your own, private sandy beach. A real chance to experience an authentic Hawaiian getaway, in an old sugar farming neighborhood away from the tourist mobs of Waikiki. We're on the south shore of Oahu,...
Scenic Maui Room with Outdoor Pool Near Ocean, Dining, Shops & Shuttle
Discover the magic of Maui from this harborfront stay! Walk to Ho‘aloha or Paukūkalo Beach, explore Iao Valley trails, and enjoy nearby dining and shopping. The perfect base for your island adventure!This listing is for a room within a hotel.✦ Your room is 432 sq. ft,...
Villa with a View - Kailua-Kona Style
Consider this condo your home away from home while you visit Holualoa. This lovely space features two comfortable bedrooms and two bathrooms, perfect for relaxing after a day of exploring. Guests will appreciate the ocean breeze that keeps the atmosphere just right. The...
Kamilo 430 - 3 Bedroom Luxury Home
Welcome to Kamilo 430, your idyllic retreat nestled in the heart of Kamuela, Hawaii. This stunning 3-bedroom, 3-bathroom villa offers a perfect blend of comfort and luxury, ideal for families or groups seeking a serene getaway. As you step inside, you'll be greeted by...
Kaanapali Maui Eldorado Partial Ocean Studio
Enjoy island living in this Maui studio with a partial ocean view, just steps from the beach and nestled on a scenic Kaanapali golf course. Ideal for two guests, it features a breezy lanai and a comfy interior. Partial Ocean View Studio• Studio kitchen includes...
2-Bedroom Oceanfront Condo w/ Private Lanai
Experience the best of Hawaii in this spacious 2-bedroom condo at Hawaiian Princess Makaha. Ideal for families or friends, this oceanfront retreat offers stunning views, a private lanai, and direct access to the beach. Enjoy comfortable living spaces, a fully equipped...
Adventurers' Dream Launchpad -no car needed!
Princeville Vacation Rental / Kauaʻi North Shore Adventure Base Your perfect launchpad for adventure on Kauaʻi’s North Shore. This beautifully renovated Princeville guest suite is just a short walk to shops, restaurants, sunset views, golf, and some of Kauaʻi’s best...
Diamond Ocean And Canal View Affordable Great Value
Amazing value and accommodation mixed in the center of Waikiki. Convenient to bus stop, shopping center, parks, and other tour places. It has a food market newly opened. This one could accommodate up to seven guests.
koolkondo 2597 Halalu Compound
2597 Halalu CompoundWelcome to your dream escape in Poipu Beach Estates! This beautifully upgraded, two-story luxury vacation home is the perfect blend of island elegance and laid-back comfort. Complete with a one bedroom Guest house, it is tucked away in a serene,...
NEW LISTING! Waikiki Ocean View One Bdrm Condo. AC, Parking, Pet. Close to Beach
PET FRIENDLY. FREE PARKING (onsite). Spend your vacation in the heart of Waikiki minutes to the beach, Ala Moana mall, restaurants and more. Enjoy ocean and Diamond Head views from your lanai (balcony). Entertain on the rooftop with BBQs, picnic tables, pool, lounge...
New Listing! Scenic West Maui Mountain View Escape
Retreat to an intimate sixth-floor studio at the iconic Lahaina Shores Beach Resort, thoughtfully curated for couples or discerning solo travelers seeking effortless island elegance. Designed for comfort and style, the residence features a plush king-size bed, central...