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.
Sky Ala Moana 2908: 2 BR, 2 BA Condominium in Honolulu, Sleeps 4
This stunning 2BR/2BA condo is located in the brand-new Sky Ala Moana building, offering breathtaking ocean views and luxurious amenities. The unit features a spacious living room, a fully equipped kitchen with modern appliances, and two elegant bedrooms with...
Maui Resort Rentals: Honua Kai Konea 348 – XL 1BR w/ Partial Ocean Views, Only 1 Stack Back from Oceanfront!
Boasting a premier location in the closest one-bedroom column to the ocean at the entire Honua Kai Resort, Konea 348 offers fantastic vistas of the tranquil blue Pacific Ocean as well as views of Maui's neighbor island Lanai. Step outside onto the generous balcony and...
Snowbird-friendly condo with ocean view, pool, washer/dryer, lanai, & grill
Kona Ali'i 502Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Conveniently located right on the bay with an unobstructed ocean view, you won't want to leave after staying at this...
Kona Sea Ridge#X1: Beautiful 2 level Spacious 3 bedroom with Ac & Ocean Views
Kona Sea Ridge#X-1 is an excellent beautifully furnished option for your Vacation. This VERY spacious, 2 story 3 bedroom, 3 bath unit has fantastic features that many guests enjoy. A perfect option for up to 6 people! ~Largest Floor Plan in Kona Sea Ridge. Living Area,...
Ko Olina Kai #17: Spacious, Stylish Retreat with Golf Course Views
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Ko Olina Kai Estate #17 by Gather, nestled on...
Kaanapali Royal K102- Maui Luxury at Kāʻanapali Royal | Heated Pool & A/C!
Welcome to Ka'anapali Royal – Your Island Escape in the Heart of West MauiNestled on the lush fairways of the Ka’anapali Golf Course, Ka'anapali Royal is a private resort community offering a refined blend of relaxation and island adventure. Located just above the...
Secluded Beachfront Luxury, Highly Desired Location
10/3/24 DISCLOSURE: Home is listed for sale and guests will need to accommodate showings with 48 hours notice. Reservations may not be guaranteed if home sells or is in escrow prior to arrival.Two-story beachfront home in Mokuleia. Four bedrooms with King, Queen and...
3BD Kauai Family Haven with A/C - Princeville, HI
This beautiful home welcomes you to endless, blissful moments! Situated in the heart of Kauai, this home boasts a beautiful location in Princeville, a charming community known for its magnificent scenery and world-class golfing.The exterior displays a lush backyard with...
2 Bedroom Garden Villa – Hali`i Kai Waikoloa 23C
Stylish island décor creates a casual vibe in this 1,082sf suite with lanai flowing onto the lawn. Homey ease plays out with a modern kitchen opening to the dining/living area, washer/dryer, flat screens, WiFi, double-vanity master bath, ceiling fans and central air....
Newly renovated, ocean view, steps from downtown
This beautifully updated 2-bedroom condo has everything needed for your Kailua-Kona trip. The condo comes with 3 A/C units, in house washer and dryer and free parking. During your stay you can also enjoy using a convenient pool, hot tub and grilling area. Our Airbnb is...
Beach Front Condo w/ Beautiful Sunrises on Private Sandy Beach + Turtles + Perfect Snorkel Spot
Escape the hustle & bustle of Waikiki crowds & enjoy beautiful sunrises, private beach, calm waters & experience amazing turtles sunbathing on the beach. Relax & experience a memorable vacation in our modern beach front condo w/ an Elegant Coastal Décor and serene cozy...
Courtyard and views of Black Rock - Newly remodeled
Unit 556 at the Whaler is a one-bedroom, one-bath. Sitting in the best location on Maui’s prestigious Kaanapali Beach, this luxurious courtyard facing condominium has breathtaking ocean and island views. Relax on the spacious private lanai while looking out over the...
Surreal ocean front view and breezes at Hali'i Kai at Waikoloa Beach Resort
11C is a prime location to enjoy those seamless Hawaiian sunsets. Situated right by the ocean, you will be able to smell the salt air as the winds of Waikoloa breeze on by. The condo is footsteps away from the Ocean Club, where you can enjoy the water front 4 tier lava...
Sunsets in Paradise
Welcome to Sunsets in Paradise - Your perfect Maui vacation rental Sunsets in Paradise is located in the heart of the Ka’anapali-Kapalua area, on the west side of the beautiful Valley Isle of Maui. We are minutes away from Lahaina, the historic Royal Capital of Hawaii...
New Custom Hawaiian Cottage - Poipu Beach- Koloa, Hi
The Sea Glass Cottage offers an unforgettable Garden Isle vacation. This custom-designed Hawaiian style Cottage is located just steps from Poipu Beach. The 2-bedroom, 2 bath Sea Glass Cottage graciously combines the beauty and simplicity of a classic Hawaiian home with...
Hanalei Bay Resort 4303: Oceanview w/ Lanais & Resort Perks, Pools & Tennis
Welcome to Hanalei Bay Resort 4303 by Gather, a beautifully appointed one-bedroom, one-bathroom condo located on Kauai’s lush North Shore. Set within the prestigious Hanalei Bay Resort, this tropical retreat offers mesmerizing views of Hanalei Bay, the majestic Na...
Alii Villas#116 Ground Floor, No Stairs, Remodeled unit to sleep 4!
Unit#116 at Alii Villas is a newly remodeled beautiful unit. This adorable condo offers an inviting blend of modern updates and island living. Recently refreshed with stylish upgrades, including new appliances and fixtures, this unit is PERFECT for those who are looking...
'The Aloha Green House' Retreat w/ Ocean Views!
The ultimate Hawaii getaway awaits at this 2-bedroom, 1-bathroom vacation rental apartment with sweeping views of the Pacific. Ideally located between Kona and Hilo, this home-away-from-home provides easy access to popular areas such as Hawai'i Volcanoes National Park...
Wailea Ekahi Gem! Remodeled Large 1BR+sleeper, Close to Beach & Pools, XL Lanai
Experience Maui paradise at Wailea Ekahi 21B, a fully renovated ground-floor one-bedroom/two-bath vacation condo nestled within the prestigious Wailea resort district. This beautiful unit showcases a designer remodel, offering a spacious, modern, and bright atmosphere...
Stunning 5 Star Ocean View Condo with all the Amenities!
Our unit is spacious with high ceilings, ceiling fans, fabulous sunlight, and gorgeous ocean views. This elevated third story unit affords a wonderful lanai with a view overlooking manicured golf courses, tropical flowers, natural lava formations, and lush palm trees...
Live Like a North Shore Local~Walk To Coffee/Store, near Road to Hana, Haleakala
We invite you to stay in our peaceful home on the North Shore of Maui, within walking distance to a local coffee shop, small grocery and near the Road to Hana and Haleakala. IMPORTANT: NO LAUNDRY ACCESS - VRBO has a glitch on my property and is showing this amenity but...
Oceanfront Private Home, AC, Outdoor Kitchen, Magic Sands, Lymans Bay, Turtles!
**'LITTLE PIECE OF HEAVEN'** -Heavenly beach house on a little Bay! *Incredible ocean views and the relaxing sound of the waves right outside your door! *ENJOY watching the Turtles sleep and play a few feet away from your lanai * Stay indoors and watch your favorite...
🌺 Oceanfront Resort Napili Shores ~ Majestic Maui Paradise ~ AC ~ Napili Bay! 🌴
Aloha & Welcome to Napili Shores C215, your second-floor end-unit, steps from pristine Napili Bay! Amazing resort amenities - 2 heated swimming pools, hot tub, BBQs, lush tropical gardens, shuffleboard, the famous Gazebo restaurant, Kitchen 5315 & Tiki Bar! Views of...
ICC 16 Kaanapali 2BD Plantation Cottage w AC Near Beach
FREE daily activities included with your stay value up to $570! Complimentary admission, every day of your stay*: Whale Watch (seasonal), Dinner Sunset Sail, Snorkel Sail, Alpaca Farm Tour, Pineapple Farm Tour, and All Day Electric Bike Rental. (W1)*One ticket per...
🏖️Includes access to Mauna Lani Tennis & Fitness facility! | 3 Primary Suites | vrKCV🏖️
vrKCV - Mauna Lani Islands K1, Professionally Managed by Kona Coast VacationsExperience Luxury and Relaxation at Villa K1, The Islands at Mauna LaniAloha! Welcome to Villa K1 at The Islands in Mauna Lani, where your Hawaiian escape combines luxury, convenience, and...
Ground-floor, golf-view condo near A-Bay beach & shops with infinity pool & spa
Waikoloa Fairway Villas O3Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Nestled in the exclusive enclave of Fairway Villas on the Big Island's Kohala Coast, this...
Splendid 2BD w/ One FREE Parking
This lovely 2 bedroom unit is a rare find in Waikiki. With 1,000 sq ft of spacious living, 2 bath, 2 balconies, 1 free parking, split AC, 4 beds, 8 guests, this unit is one you can't go wrong with. We are centrally located making restaurants, Friday night fireworks,...
Luxurious 3-Bedroom, The Villages at Mauna Lani #325
Luxurious 3-Bedroom Villa at The Villages at Mauna Lani | Hawaii Dream GetawayWelcome to your private slice of paradise! This stunning 3-bedroom, 3-bathroom luxury villa located in The Villages at Mauna Lani offers the perfect blend of relaxation and elegance, with a...
Kona Sea Ridge Y23 30 day minimum rental
Summary:Welcome to our bright and spacious 2-bedroom, 2-bathroom condo, offering stunning ocean and mountain views. Relax on the large lanai overlooking lush grounds and a sparkling pool. This second-floor unit features an open layout with a well-appointed eat-in...
Hale Kamaole 276 Second floor condo, easy access to best beach on Maui!
**7 Night minimum stay required**Ocean Views Forever – also overlooks beach. Unit just completely Upgraded and remodeled with high end materials, finishes and furniture. Master Bedroom has King Size Bed, spacious Master Bathroom and large flat screen TV. Downstairs...
Wailea Ekahi Village | 22F
Wailea Ekahi 22F is located in an ideal location, closest on property (a short walk) to Keawakapu Beach and the Wailea Ekahi beachfront swimming pool and recently remodeled beach pavilion. Whip up some happy hour drinks and snacks in your vacation rental and then stroll...
Paradise vibes awaits @ Hali"i Kai, ocean front resort in Waikoloa Beach
23H Island inspired décor to give you all the feels of Hawaii. This 1400 square foot 3 bedroom, 2 bath condo is located in the most desired resort on the Big Island, Hali'i Kai at Waikoloa. Situated in the coconut grove amongst the relaxing tropical garden, 3 outdoor...
Gecko'z South Sea Bungalows
Welcome to South Sea Bungalows:South Sea Arts has grown beyond the gallery and restaurant designing to provide Polynesian culture aficionados, collectors of Hawaiiana and people who appreciate culture in an oasis to call home during their stay on the island of Oahu....
Poipu Shores 205A - Best views - Compare! miles of coastline -A/C-Fully equipped
Poipu Shores is a gem property perched overlooking the Pacific Ocean on a rocky cliff where you can view sealife year round from your private covered lanai. Enjoy endless views from our oceanfront pool. There are two gas grills, larger ocean front entertainment area for...
~Naupaka Breeze~ Newly remodelled! Ocean View Home 30 Day Stays
Recently updated ocean view home on an ocean front peninsula. Enjoy the views of Laie Bay from the comforts of the home or deck of the house, or venture to the Ocean Front cliffs right in the back yard and indulge in the beauty captured only from this peninsula.Naupaka...
4Br 4.5 Ba Punahele House with Ocean and Mountain Views, Beach Gear, Near Queens Pond
Welcome to the Punahele bluff! The treehouse style upstairs vibe of this house with oversized deck, entertainment kitchen, and extremely large spaces makes you feel like you are part of the Hanalei mountain range. It's so close you can touch it! You have ocean views,...
Elevated Honolulu Sanctuary Renovated w/ Aircon
*** Disclosure: All rooms are renovated in a similar fashion. Furniture style may vary in pictures and in the unit. Functionality are all the same. Queen size bed in bedroom, sofa bed in the living room. Washer dryer in the unit, free WiFi, free tandem parking allowed...
Kakela Kai, Beachfront Kailua Home, Private, A/C
A comfortable beachfront home set in a security-gated neighborhood with central air condition. Decorated with island style rattan furnishings, ceiling fans throughout the house, cool white tile, granite counters and wooden flooring. There is a well stocked kitchen with...
Beautiful Hawaii!nPanoramic Ocean View, a Private Pool!
30 Days Rental!**Rates are subject to change during peak seasons, holiday and summers. Please communicate with Host for renting!Panoramic Ocean & Mountain View from Entire House.Located in central area that is close to everywhere, 5 to 10 minutes to World famous Waikiki...
'We Loved This Romantic Getaway for Two !' - Testimonial.
This rustic wooden mountain cabin is situated next to a forest, in a secluded spot away from the main house, on a 3.5 acre farm. At an elevation of 2,100 feet, it avoids the summer heat at sea level ('Cool and peaceful..' - Teri), yet is close to Kealakekua Bay (5...
New Listing! Peaceful Poipu Retreat Waikomo 200
Experience the perfect blend of serenity and convenience in this beautifully updated one-bedroom corner unit at Waikomo Stream Villas. Nestled among lush Hawaiian foliage, this modern retreat offers a peaceful jungle atmosphere while being just steps away from Poipu's...
Charming Cottage
TVR 4181: Charming cottage above historic Koloa Town, about 20 minutes from Lihue airport.Front door opens into expansive screened-in lanai with dining table. Living room includes comfortable furnishings, seating area and a pune'e, Hawaiian style couch, that can sleep...
Regency 610 Mala Pua by Destination Kauai - Central AC, Walk To The Beach
E Komo Mai, Welcome to Mala Pua Regency 610!A 2-bd/2-ba ground floor condo in the heart of beautiful sunny Poipu offers the perfect home away from home. Enjoy open living space with two sofas, TV entertainment center, and a fully-equipped kitchen with granite counter...
Beachfront condo w/AC, Ocean Views, Steps to Beach, Sunrises and Moonrises
A spectacular second-floor beachfront condo offers breathtaking views of the ocean. The beach is steps away so take your morning cup of coffee on the beach as you watch the inspiring sunrise and listen to the soothing sound of the waves. Conveniently close to shops,...
1-Bedroom unit on the 21st Floor overlooking the surrounding Waikiki area!
1 Bedroom City View on the 21st Floor! Relax in the bedroom or lanai and watch the Honolulu city come alive at night. There is a Blu-ray and Netflix for you to watching movies and TV during your stay. **Condo is listed for sale by the owner. Guest must allow to showing...
Ocean View Poipu Sands Condo in sunny Poipu
Beautifully appointed 1 bedroom, 1.5 bath ocean view condo offers the Kauai experience you've been looking for! Highly sought after ground floor unit provides abundant open space and direct access to the barbecue grill and pool. Plenty of free parking close to the condo...
The Best 3bd 3ba Condo Near Ocean with AC Office and Loft ACJ1
TMK: 750180080055TA-014-093-3632-01Alii Cove's Best Ocean Views! This unit is very quiet and has exceptional ocean views from the main lanai and upper lanai. The townhome comes with anything you could possibly need for an extended stay, including super fast wifi! Alii...
Beautiful Oceanfront Kona Reef Resort Private Top Floor Condo A33, AC throughout
We are the proud owners of this beautiful vacation home and we are excited to share this slice of Paradise with you! We are experienced Superhosts and Premier Partners and we have worked hard to make sure you will have the most comfortable stay ever!We have updated this...
Puamana Maluhia - Princeville Two Bedroom / Two Bathroom
Come and relax in our newly renovated, two bed, two bath condominium on Kauai's famous North Shore. Adventures abound so rest assured our place will be your spot to rejuvenate. Surrounded by cool coastal towns like Kilauea and Hanalei, Puamana is centrally located...
Ekahi 8F, Oceanview Studio, extremely close to Beach and Main Pool! 2nd Floor
Escape to paradise with stunning ocean and green belt views from the lanai of this 2nd floor studio. 8F is a fully-furnished studio featuring cathedral ceilings, a comfortable living area, a California King bed, and a fully-equipped kitchen. The layout and décor of our...