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.
Sea Village Oceanview Condo
Unwind with modern comforts, including a flat-screen TV with cable, high-speed WiFi, and a fully equipped kitchen perfect for preparing island-inspired meals. Step outside to soak up the sun in the oceanfront complex, where you can lounge by the pool, take a dip in the...
G204 | Tropical Paradise | Beachy Kihei Surf Bungalow
Welcome to your perfect Maui getaway at this beautifully updated 2-bedroom, 2-bathroom condo in Kihei Garden Estates. The contemporary "surf shack" design creates an authentic Hawaiian atmosphere, featuring a spacious loft primary bedroom with a plush king bed and...
KRV 1023 Experience Kapalua Maui from this 2BD condo with Spectacular Oceanviews
Kapalua Ridge Villas 1023 NEW LISTING Sweeping Kapalua Ocean Views from this Beautifully Remodeled Spacious Maui Villa! This spacious West Maui retreat offers breathtaking panoramic ocean views, with the neighboring island of Molokai as your dream backdrop. Thoughtfully...
Unique Chic Hotel with pool, WiFi, gym & AC in world-class Waikiki, Hawaii.
This lovely hotel room in Waikiki offers guests a comfortable stay with AC, WiFi, smart Roku TV, a newly renovated spa-like bathroom, balcony, fully stocked kitchenette, full gym, temperature-controlled outdoor pool with lush tropical lounge deck, and a BBQ deck area....
NEW! 2BR/2BA Tropical Paradise in the HEART of Waikiki - Foster Tower
NEW ON THE MARKET!We welcome you to our Aloha HOME! Soak in Paradise in this pristine, luxurious 20th floor suite with panoramic ocean and mountain views. The beach is right out front. When not at the beach, enjoy the onsite pool, hot tub, sun deck, fitness center, and...
Gorgeous Remodeled hotel suite in Princeville w/ pools & beach access, sleeps 4
Unwind in Princeville at this lovely hotel suite! Enjoy the modern comforts of this remodeled unit with A/C, a comfortable king-sized bed, 50" TV, sofa with a queen-sized pull-out bed, and a private lanai with a beautiful view of the north Kauai Mountains made famous by...
The Grand Islander, a Hilton Grand Vacations Club
Discover the beauty of Honolulu from this adorable 2-bedroom resort. The rooms feature 1 king bed in primary room and 1 king or 2 double beds in the second bedroom. perfect for a serene night's sleep. Enjoy the convenience of 2 full bathroom with showers and a cozy...
Papakea G-205 - Ocean Views - Free Fun - NEW LISTING
Ocean views at Papakea Resort in North Kaanapali. This beautiful 2-bedroom, 2-bath condo in a 4-story concrete building has been updated. Remodeled guest bathroom and new master vanity in October 2025. ** NO RESORT FEES ** "Sale" into Whale Season: PROMO CODE: SALE26....
🏝️SUMMER Deals - Walk to the beach, great and convenient location LSV15🏝️
South Maui Condo Steps from the BeachWelcome to our bright and airy second-floor end unit in the heart of Kihei. Located in Building 4, Unit #223, this condo offers windows on three sides, allowing natural light and refreshing trade winds to flow through.What Makes This...
Secluded Oceanfront Cottage- in Princeville – Private large Spa & Stunning Views
For less than half the price of a standard hotel room, this private ocean bluff Cottage-Studio offers a luxurious and romantic experience—giving you more space, more privacy, and more of Kauai’s magic. Instead of a crowded resort, you’ll wake up to the sound of waves,...
Gorgeous Napili Shores studio A/C
Come relax is this updated ground-floor studio located on famous Napili Bay (6 minute walk to beach!) Comfy, king-sized bed and twin sofa sleeper, full kitchen (all new appliances) with everything you need (fully stocked- even spices & oils!) Very close outdoor BBQ area...
Cozy 2-bedroom apartment in amazing Kailua-Kona with WiFi, AC
Walk to the Beach! This peaceful 2-bedroom Kona Shores condo offers the ideal blend of location and comfort. Stroll to Honl’s Beach and enjoy the oceanfront cafés along Ali‘i Drive, then return to a fully air-conditioned space with a private lanai and access to the...
Pualani Villa by Gather: Luxe Princeville Retreat w/ Pool & Hot Tub
Escape to Pualani Villa by Gather, a stunning three-bedroom + den, 2.5-bathroom townhome in the heart of Princeville’s prestigious resort community. Offering a beautifully designed living space, this two-story retreat combines modern luxury with island charm, creating...
AlohaCation - Oceanfront Work and Family Time
Work from Paradise or Enjoy Family Time by the BeachImagine waking up to breathtaking ocean views, working remotely with the sound of waves in the background, or spending quality time with your little ones on a peaceful, safe beach. Our oceanfront apartment blends...
Walk to Kalapaki Beach: Condo w/ Ocean & Mtn View!
Banyan Harbor | Saltwater Pool Access | Near Shopping & DiningSay hello to a prime location with 24-hour security and an easy drive to the North and South shores at this Lihue vacation rental. This single-level unit features 2 bedrooms, each with a private full...
A Tropical Paradise 2 Bed/1bath. Stunning Bay and Ocean Views
A Tropical Paradise on Hawaii's Big Island This updated 2bed, 1/bath penthouse has stunning views of both the bay and the ocean. Whether you are a lover of marine life or just a lover of tropical views, this home is the perfect spot for you. The penthouse's prime...
PERFECT LOCATION BEACH FRONTnINQUIRE special discounts reduced rates for march
Experience Haleiwa like a local in this delightful 1-bedroom apartment. Relax in the cozy living room or unwind in the jetted bathtub after a day of exploring. The bedroom features a comfortable king bed for a brilliant night's sleep. With amenities like a washing...
Maui Westside Presents - Eldorado H208
🌺 Aloha from Maui Eldorado H208! 🌺Winter Special - Book 7 nights and receive a 10% length of stay discount. Rates are updated automatically and applied when selecting 7 nights or more. Escape to your dream Maui getaway in this fully renovated, 1,440 sq ft, 2-bed/2-bath...
Coconut Coast Oceanview
Enjoy convenience and simplicity from this peaceful and centrally-located retreat. Watch the sunrise over the Pacific from your private lanai , walk to lots of restaurants and shopping at the nearby Coconut Marketplace as well as Longs Drugs, Safeway, Starbucks and...
Ocean View•1 BR Corner Condo•Mins to Waikiki Beach
Experience breathtaking, panoramic ocean views from this stunning top-floor 1-bedroom condo in the heart of Waikiki. This spacious retreat offers an open, airy layout with original hotel finishes, large windows, and a private outdoor dining space perfect for soaking in...
3 bedrooms 3 baths • Oceans views • Steps to beach
A combined rental for 2 adjacent, beautiful ocean & sunset view condos. One is a 2 br 2 bath double lanai unit and the other is a 1 br 1 bath unit. The combined space is 3 bedrooms 3 baths sleeping up to 10! You will have an ocean view triple wide lanai, 2 living rooms...
Spectacular View, Direct Oceanfront Kona, Top Floor, Brand new A/C
ALOHA, WE INVITE YOU TO RELAX AT SEA VILLAGE, New A/COur lovely top floor condo is perfect for you! Sit back and take in the spectacular view from the lanai as you watch dolphins and whales (in season) during the day and beautiful sunsets in the evening! Lose yourself...
40% off ! Oceanfront Views in the Heart of Kihei - Full A/C, W/D, 85"TV
Panoramic ocean views from this beautifully updated, fully air-conditioned condo at the popular Island Surf complex in Kihei. This airy guest favorite is across from Kalama Beach Park and Cove Beach. It's a 2-3 minute walk to food trucks, bars, restaurants and shopping....
Maui Resort Rentals: Honua Kai Hokulani 138 – Upgraded Large Ground Floor 1BR, Spacious Lawn Area + Easy Pools/Beach Access!
Maui Resort Rentals is proud to bring you this extraordinary 1BR Ground Floor Garden View Suite at the Honua Kai Resort, newly launched on 2/5/2025 to start taking reservations for check-ins starting 3/14/2025!Hokulani 138 is a luxurious ground floor suite with one of...
New Listing: Waipouli Beach Resort, Pool, AC, Gym & more
Escape to the luxurious Waipouli Beach Resort, where villa F202 offers a blend of elegance, comfort, and Hawaiian charm. This stunning 2-bedroom, 2.5-bathroom condo is the perfect retreat for families, couples, or friends seeking the ultimate Kauai getaway. Step inside...
Cozy 3bd/3b Beach Retreat, Sleeps 10, AC, WiFi, Fam-Friendly in fantastic Koloa
Escape to paradise in this relaxing 3 bed/3 bath retreat at the Pili Mai condos located on the Kiahuna golf course. This unit can sleep up to 10 guests, relax in its plush interiors with a king bed, 1 queen bed and a cozy bunk room (1 queen, 1 full, 2 twin beds),...
Kona Islander Inn - #316 - Located in beachfront town of Kailua Kona Hawaii.
Experience the convenience of being close to popular beaches, shops, restaurants, and historic landmarks with this delightful and cozy retreat. Ideal for explorers and relaxers alike, it is your perfect base for memorable adventures and relaxation. You can walk to many...
Modern Spacious Beachfront Luxury in Wailea. Family Friendly!
A modern 2 bedroom, 2 bath condo with extra bunk beds and an amazing ocean view!South Maui is one of the most beautiful destinations in all of Maui and Wailea Ekahi Village is a perfectly situated, beachside resort we call home. Guests return to Ekahi year after year to...
Kolu Honu – Stunning Beachfront Condo for 2!
Summary:You’re so close to making the Hawaiian vacation of your dreams a reality, and at Kolu Honu, all the enchantment of the islands comes to life, beckoning you to a truly magical experience!The Space:You're just moments away from making the Hawaiian getaway of your...
Hale Kunu | Stunning Views
Summary:Say aloha to your Big Island vacation rental! Hale Kunu is nestled in the oceanfront condo complex White Sands Village, located in the gorgeous town of Kailua-Kona. Maximum occupancy strictly enforced in accordance with local ordinances.The Space:Guests will...
Na Hale O Keauhou | Beach Views, Hot Tub & Pool
Summary:Welcome to Na Hale O Keauhou #I1! Located in one of Keuhou’s newer neighborhoods, this one is a delightful Hawaiian getaway home. Enjoy nearby beaches and glorious sunsets, it’s perfect for vacationers looking to unwind and bask in the tropical sun. Maximum...
Kona Reef F2 – Charming Oceanfront Condo for 4!
Summary:The mesmerizing gem of Kailua-Kona is something that truly has to be seen to be believed, offering an unforgettable tropical escape for visitors from around the globe.The Space:Margo and Frank first came to the big island some 10 years ago. They came to Kona...
White Sands Village #217 – Perfect Tropical Escape
Summary:Whether you seek serenity along ocean shores or adventure beneath the waves, White Sands Village offers an unforgettable getaway immersed in the culture of the Hawaiian Islands. Located on Hawaii’s Big Island in beautiful Kailua-Kona, this 2-bedroom vacation...
Kaanapali Royal Vacation Rental - Tropical Paradise with Stunning Views
Kaanapali Royal Vacation Rental - Tropical Paradise with Stunning ViewsLocation Highlights: • Prime Kaanapali location in a quiet, gated complex • Breathtaking golf course and ocean views • Large private lanai • Convenient access to Napili and Kapalua beaches,...
Pili Pono: Elegant Honolulu Retreat with Pool & Private Oasis
Welcome to Pili Pono, a show-stopping 5-bedroom, 6.5-bath luxury estate set within Honolulu’s prestigious Black Point enclave. Spanning 7,470 sq ft of indoor–outdoor living space on a fully enclosed, gated 0.33-acre lot, this custom-designed retreat blends architectural...
Spacious retreat with hot tub & BBQ grill
Summary:Ocean Front Pool/Hot Tub, Near Golf /Beach, TennisThe Space:Welcome to your Hawaiian retreat at Waikoloa Beach Resort - perfect for families & groups seeking relaxation by the coast! Enjoy peaceful garden views, resort amenities & easy island living:- Sleeps 6 |...
Honu Hideaway Studio at Royal Garden | Lanai Oasis
This gorgeous Waikiki studio is located at the beginning of Waikiki with easy access to some of the best Oahu has to offer. At the luxurious “Royal Garden” building, guests are free to enjoy the gardens, pool, sauna, BBQ grills, fitness center, 24/7 laundry room with...
Fully Renovated Studio in the Heart of Waikiki – A/C, Wi-Fi, FREE Parking!
Marine Surf #2207 – 364 Seaside Ave.Beautifully furnished contemporary 22nd-floor studio in the heart of Waikiki, fully renovated in January 2025, complete with resort-style kitchenette, comfortable Queen size bed, A/C, free high-speed Wi-Fi, and 1 free onsite parking...
Wailea Elua 1304 - Spectacular Oceanfront Condo with Panoramic Views
Wailea Elua #1304 – Oceanfront Comfort in the Heart of Wailea’s Resort CommunityWelcome to Wailea Elua #1304, a beautifully appointed 2-bedroom, 2-bathroom oceanfront condo offering the perfect blend of luxury and relaxation. Nestled in one of Wailea’s most exclusive...
Comfortable Camping - North Shore Oahu #2
This simple accommodation creates a distraction free space to reconnect. You’ll love peering over the banana trees and watching the sun disappear beyond the mountain. There is incredible stargazing at this site. To top off your vacation bliss, the glamping tent is just...
Ko'Olina Retreat - Short Walk to Resorts, Golf, Restaurants & Lagoons!
Welcome to your dream retreat in the heart of Ko'Olina! This beautifully remodeled 3-bedroom, 3-bathroom townhome is nestled in the exclusive, gated community of Ko'Olina Kai, offering the perfect blend of luxury, comfort, and island charm.Step inside and be captivated...
Hawaiian Oceanfront Oasis
Summary:Escape to our newly renovated oceanfront property for the ultimate island getaway. Enjoy breathtaking ocean and mountain views right from your doorstep, with easy access to the best local food and famous attractions just minutes away. Experience the perfect...
Island Oceanfront Getaway
Summary:Relax with the whole family at this peaceful home. Our newly renovated oceanfront property is the perfect island getaway. With ocean and mountain views from your doorstep yet just minutes from the best local food and famous attractions you will enjoy the perfect...
Kona Bali Kai#164:Stunning Remodeled Studio with Ocean Views: Walk to Beach!
Discover the perfect blend of island living in this gorgeous fully remodeled studio unit at Kona Bali Kai with Ocean views located on the desirable ground floor. This beautiful unit offers just what you need for your Vacation: Ocean Views, Beautiful Furnishings, Very...
Fully Renovated Condo located close to the beach!
Newly remodeled, and conveniently located, this 556 sq. ft. 1 bedroom, 1 bathroom condo villa offers privacy and modern comfort set in the heart of popular Kihei Town!This unit sleeps 2 guests on the comfortable king bed with built in wardrobe cabinetry and individual...
Kahikole Street Estate – Four Seasons Hualalai Home with Pool & Spa
Aloha and welcome to your private oasis at the exquisite 4 bedroom home in Hualalai with amenities near The Four Seasons resort. Spectacular views include an unobstructed ocean panorama and the Kohala Volcano to the north, you also enjoy a front row seat of the 8th hole...
Boutique 1-bedroom condo in Waikiki! WiFi, AC, Pool, Hot Tub, BBQ Free Parking
Enjoy a pleasant stay at this newly rennovated 1-bedroom condo in Waikiki, Honolulu with Free Parking. This 11th floor home features 2 queen beds,a pullout sofa-bed, Japanese tolilet, magnetic arm and rainshower head,perfect for a small group of guests and families....
❤️PiH❤️ Hono Loa ★ Bikes/Beach Toys ★ Private Beach Club ★
Presented by Paradise in Hawaii Luxury HomesWelcome to Hono Loa at the Fairways in Mauna Lani!Hono Loa offers the ultimate backdrop for your Hawaiian getaway. Perfectly designed to accommodate up to 6 guests, it's an inviting, luxurious, and serene retreat for both...
New Listing! Beautiful ocean view 2bed/2ba Condo on Kaanapali Beach Resort-style
Welcome to our beautiful 2 bedrooms and 2 bathrooms ocean view condo at Kaanapali Shores! Sleep up to 8 guests. Perfect for your family or group traveling together to beautiful Maui.Kaanapali Shores's location in the heart of West Maui where you can find many 5-stars...
Walk to Poipu Beaches: Koloa Condo w/ Pool Access!
Community Hot Tub, Grills & Tennis Courts | 1 Mi to Poipu Bay Golf Course | In-Unit LaundryCreate lasting memories at this 2-bedroom, 2-bath Koloa condo! Boasting an open layout with 2 balconies, access to resort-style perks, and a prime location near stunning ocean...