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.
Private Pool, Hot Tub with AC, BBQ and Very Spacious
Welcome to your private island retreat in Kiahuna Golf Village—an elegant two-story home with distant views of the ocean, mountains, and lush Kauai landscape. Ideally located just minutes from the Poipu Shopping Village and the famous Poipu Beach, this spacious...
Direct Oceanfront 2B/2B ~ Maalaea Banyans 409 ~ Gorgeous Views, Great Location!
Enjoy being lulled to sleep by the sounds of the surf and the palm leaves swaying in the cool tropical breezes in this charming ocean front condo. Private lanai showcases a beautiful view that can be seen from the living room and kitchen. Also found here is an open air...
Entire 2 Bedroom Condo, King Bed, FREE Parking, Sleeps 6, Walk to Waikiki Beach
Aloha and welcome to Waikiki! Our condo is located at the Royal Aloha. We are minutes from the beach and the Waikiki strip. We offer the following:Free parking stallFull kitchenWifiPrivate lanai (balcony)Jalousie windows Ceiling fansPrivate Master Bedroom - Queen...
Gorgeous 2bd condo - walk to the beach
Ocean Views | Walk to Beach 2 Bedrooms • 2 Bathrooms • Sleeps 6 • 3 BedsBook with confidence – this property is located in a district not affected by any of the currently proposed transient vacation rental restrictions in Maui. Your reservation is secure and will remain...
Sugar Beach Resort 334: You will Feel like you're Sitting on the Water
Sit on your lanai and enjoy the Ocean Front views that will make you feel like you are sitting on the water. This third-floor condo has one bedroom and one bathroom. The bedroom has a king bed and the living room has a pull-out sofa bed, allowing this unit to...
Renovated Ocean Front 1 Bedroom! Ilikai Marina (IM92)
Firework! Great Ocean View! Ilikai Marina (IM92)In the sunFeel the sunWalk barefoot on the sandFeel the OceanRelaxEveryday sunny daySoak up Nature While In Hawaii!!This modern studio is bright thanks to the top to bottom windows. The studio offers a fully equipped...
Ocean-view condo on top floor with lagoon pool, hot tub, AC, W/D, great location
Maui Kamaole A214Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Luxury and privacy meet at this Kihei Condo, located in the condo resort known as Maui Kamaole®, and just minutes...
Lovely, oceanfront island home with pool, & washer/dryer
Mahina Surf 110Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'With such a perfect location next to the crystal waters of the Pacific Ocean, this amazing island home enjoys a...
Ocean & Lagoon Views
Luxury Oceanfront Condo in Waikiki – Stunning Views & Prime LocationExperience the beauty of Waikiki Beach from this exceptional oceanfront two-bedroom, two-bath condominium at the renowned Ilikai, famously featured in the original Hawaii Five-O series. Wake up to...
Studio in Princeville on Kauai's North Shore
Our studio is convenient to all the wonderful activities, beaches and scenery the North Shore of Kauai has to offer. Featuring queen bedding, flat screen TV, fully remodeled bath in Oct 2024, mini frig, microwave, toaster, and lanai making it the perfect spot for your...
Princeville Ocean Escape
Princeville Ocean Escape is a serene retreat perched on Kaua‘i’s North Shore bluffs, offering breathtaking ocean and palm views and modern comforts. The open-concept living area features floor-to-ceiling windows framing Pacific vistas, while a cozy daybed invites...
Spacious 3 Bedroom Ocean Front W/Lanai-Kaha Lani
Kaha Lani unit #307 on the third floor: One of the only three-bedroom, two-bathroom units showcases an open floorplan as one of the largest units in the complex, with tropical island décor and modern fixtures throughout. Floor-to-ceiling sliding glass doors allow for...
Maui Banyan Ground Floor 2 BR/2 BA at Kam II Beach. Family-Friendly, Sleeps 4-8
Imagine staying a one-minute walk from Kamaole II Beach in Kihei, with several lifeguards on duty 365 days a year. That's an uncrowded sandy beach conducive to sunning, snorkeling, swimming, and sunset watching. In winter you can even spot whales cavorting not far...
Charming Kailua-Kona Apartment Near Hiking & Golf!
Head to the Big Island of Hawaii and relish the ocean breeze at this coastal retreat! With 1 bedroom and 1 bathroom, this vacation rental offers a relaxing respite for couples looking to experience island life. Spend your days swimming at Kamakahonu Beach, traversing...
Sweet Ground Floor Suite w/WiFi, Lanai, Kitchen, Flat Screens, DVD–Kaha Lani 122
Castle Kaha Lani Resort #122 - This spacious 1,183 sq. ft. two-bedroom vacation condo is just steps from the shores of Kauai’s east coast. With its full kitchen, separate living area and bedrooms, and convenient touches including ceiling fans, flat screen TV, and WiFi,...
Cozy North Shore Charmer w/ Beautiful Ocean Views & Great Amenities
Alii Kai 8H is a lovely, private top floor condo with gorgeous views of the ocean that you can enjoy from your balcony lanai. This two bedroom corner unit has a comfortable and homey main living space, a fully stocked kitchen, and two private ensuite bathrooms so nobody...
Great Waikiki Studio, Just Steps to Waikiki Beach, Zoo WAIKIKI GRAND HOTEL® 801
Legally permitted rental - 134 Kapahulu Ave #801Allow us to welcome you to our Hawaiian home with the warmth of our “aloha” hospitality. We are just half a block from the beach in one of Waikiki's best locations. We actually have two charming studios, adjacent to one...
Maui Sunset A303 - Great large 1 bedroom close to ocean
Book with us and come to Maui to explore everything we have to offer!This nicely furnished 3rd floor 1 bedroom with 2 bathrooms is the perfect place to relax when in Maui. Full sized kitchen and large living room to relax in after your busy day under the Maui sun....
Amazing oceanfront views, 2bd spacious condo
Kanai A Nalu 202 is a 2nd-floor condo with 2 bedrooms and 2 bathrooms that offers 1 window A/C unit in the living room, ocean and pool views, and a private washer/dryer. This property has elevators for easy access. Unit 202 can accommodate up to 6 guests. This spacious...
5 star review gorgeous private pool/spa with ACs close to beaches
Aloha and welcome to Kilohana Hale. This beautiful house is located in an upscale peaceful neighborhood. Kilohana Hale is only minutes away from Magic Sand Beach, Kahaluu Beach Park, and downtown Kailua-Kona. This 5 bedroom2, 4.5 bathrooms, ocean view home can...
Tropical Splendor! Ocean View w/Wraparound Lanai and Kitchen–Waikīkī Shore #600
With chic décor and touches, this luxe 1,190sf corner suite defines tropical splendor! Friends and families embrace the space and amazing Pacific/Diamond Head panorama flowing from the wrap-around lanai into the open-style living area and gourmet kitchen for “at home”...
Ocean views from every room @ this 2 bedroom condo
Welcome to Hololani A404. Ocean views from every single room on this 4th floor corner unit. This 2 bedroom, 2 bathroom unit features ocean & Molokai island views. This unit can accommodate 6 people with the living room's queen sofa sleeper. Enjoy sunsets & whale...
Maui Vista 1210 | Renovated Condo, Balcony, Pool!
There’s a reason guests return year after year to Maui Vista 1210. The condo is beautifully maintained, in an ideal location across from Charley Young Beach, just north of Kamaole Beach I, and offers amenities that are simply exceptional. Best of all, the resort has an...
Ocean View 4-bedroom house with AC, WiFi in welcoming Princeville
About this space:Open & Spacious Tri-level home sleeps 12+ w/4 bedrooms & 3 bathrooms.Perfect for Friends & Family Gatherings!TOP-LEVEL: Master Suite w/180 degrees of Ocean, Mountain & Waterfall View, 2nd bedroom, 2 baths + bonus TV loft area.MIDDLE-LEVEL: Open Concept...
Honomu Home w/ Screened Lanai + Ocean Views!
Your next exciting stay on the Big Island awaits at this stunning Honomu vacation rental! Walk across the tranquil landscaped pond with floating lily pads into this 3-bed, 2-bath home’s open and bright interior, which features stylish touches like exposed wood beams,...
House of the Rising Sun
Per Oahu law, all bookings must be for a minimum of 29 nights. If you plan to stay less than 30 days, that's OK but your booking will still be for 30 days per Oahu Law and the monthly rental fee will NOT be pro-rated based on the actual number of days you plan to occupy...
Stylish Modern Studio in Waikiki, Steps from Beach!Tradewinds
Welcome to a brand-new modern studio apartment, ideally situated in Waikiki steps from the stunning beach, waterfront park, and Honolulu Zoo, this vacation rental is perfect for couples and solo travelers wanting to experience the best of Hawaii's vibrant city life...
Spacious house with private gas grill, shared pool, close to golf
The H-HouseOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'The award winning "H House", designed by George Heneghan, is truly one of Waikoloa's finest architectural specimens. In the...
Ocean-view corner unit at oceanfront resort - steps to beachside pool & hot tub
Islander on the Beach 304Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Discover the perfect ocean getaway at Islander on the Beach, a 6.5-acre oceanfront resort with stunning...
Kahala Beachfront Unique Bohemian Home
($99- Clean Fee special for Spring bookings, please inquiry. Car/ Suv Available at discounted rate- pls inquire)A relaxing escape in this abode situated in the coveted Kahala, tucked away for your enjoyment . ENTIRE High end condo-home for rent (2bedroom 2bath) with a...
Oceanview 1BR- Top Floor Elevator access - see video tour -WiFi and free calling
This is a top floor oceanview unit with an excellent ocean view and overlooks the pool area. It is one of many of the nicer units we own or manage, including two bedroom ocean front units, 1 bedroom ocean front units, and 1 bedroom ocean view units. It is fully equipped...
Beautiful house on golf course with amazing lanai, washer/dryer, & patio
Hale Ho'omahaOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'With its soaring ceilings, open and breezy layout, and wall of glass framing the Makai Golf Club out back, this...
Aqua Aloha Surf Waikiki 1501 Deluxe Studio with Lanai and Partial City Views
Aqua Aloha Surf Waikiki 1501 Deluxe Studio with Lanai and Partial City Views located just 2 Blocks to Waikiki Beach, (1) Full/double bed, (1) Twin bed, (1) Queen sofa sleeper, Sleeps 4, 360 St FtAqua Aloha Surf Waikiki brimming with island personality offers a range of...
Fall Special! Hale Nene Volcano A-Frame Cottage with Hot Tub
This one bedroom home Hale Nene is perfect for honeymooners, a special anniversary, or as a writer or artist's retreat. With a brand new queen-sized bed and sofa couch in the living room, it sleeps 2-4 guests comfortably. Max 4 guests. Reserve the Hale Palila cabin next...
Matchless condo with washer/dryer, pools & condo - near multiple beaches
Maui Kamaole I216Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Luxury and privacy meet at this Kihei Condo, located in the condo resort known as Maui Kamaole®, and just minutes...
Maui Kamaole C209: Ocean View, 2 bedroom & 2 bathroom condo in S. Kihei
Oceanview condo with two bedrooms and two bathrooms. The beautiful furnishings in the condo incorporate bright colors and wild sunlight to make this unit inviting and suitable for anyone looking to enjoy their time on Maui. The lively décor brightens the area and is...
Tropically lush grounds with beachfront breezes
E Komo Mai “welcome” to Hale Mahina B103! This beautiful one bedroom, one bathroom ground floor condo has a well thought out, open concept floorplan. It does not have A/C but has ceiling fans throughout. The living area offers a queen sleeper sofa for additional guests...
Ocean-view Sugar Beach Resort condo overlooking pool, hot tub & beach access
Sugar Beach Resort PH04Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Experience the laid-back island life at this tropical condo at the oceanfront Sugar Beach Resort. Spend your...
Pair of Maui Kai Suites with Shared Pool & Hot Tub - Near Beaches, Golf & Dining
Maui Kai 507 & 508Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'This family of Maui Kai condos is exactly what you need to wow your family and friends! Enjoy breathtaking ocean...
Kona Reef F13 - Nicely Renovated - Ocean View - Free WiFi, 3 minute walk to town
You have just found your vacation spot in Paradise! Sit back and enjoy the spectacular, crystal blue and balmy Pacific Ocean.This one bedroom, one bath, Ocean View condominium is on the second floor of the F building with fabulous ocean/sunset views. It is wheelchair...
Ocean View Oasis Escape, Sunset View & Fast Wi-Fi
Summary:🌴 Steps to the Beach – Charley Young & Kamaole 1 nearby📍 Prime Location – Walk to top restaurants & shops💻 Fast WiFi + Smart TV 🏠 Spacious & Stylish – Modern decor & cozy ambiance💎 Luxury King Bed – Guests rave about comfort!🏊 Resort Perks – Pool, hot tub, BBQ,...
Condo near the beach with grill, pool & hot tub - near surfing, biking & golf
Maui Kamaole K110Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Luxury and privacy meet at this Kihei Condo, located in the condo resort known as Maui Kamaole®, and just minutes...
Ocean Views in the Heart of Waikiki Beach
STUNNING OCEAN VIEWS in the heart of the most famous beach in the world, WAIKIKI BEACH! Just a stone's throw away from white sandy beaches, fun ocean adventures like surfing, SUP, canoes, & all the pampering options of the 5-star resorts. The unit has AC & a lanai with...
WE 1509 Beautifully Remodeled Wailea 2BD w Ocean Views AC Pools Golf Course
Wailea Ekolu 1509 Luxurious 2Bedroom Wailea Villa on The Wailea Blue Golf Course with Expansive Occean Views, AC and Pools. Close to Beaches, Shops, Restaurants, Tennis FREE daily activities included with your stay value up to $956! Complimentary admission, every day of...
GOLF COURSE UNIT - NO STAIRS!
Walk right out of your condo onto the spacious covered lanai just feet away from the beautiful Keauhou golf course with an ocean view across the course, you will never want to leave! Roomy 2 bedroom, 2 bath (end unit)condo with parking nearby, and no stairs. Located at...
Sunset Haven: Elegant Beachfront Maui Retreat
Summary:🔹 Walk to Charley Young Beach – Just 3 blocks away 🌅 Ocean Views – Enjoy coffee on the private lanai 💤 King-Size Bed – Luxury linens for restful sleep 📶 Fast WiFi & Smart TV – Work& stream seamlessly 🏖️ Beach Gear Included – Chairs, towels umbrellas 🏊♂️ Pool &...
Hotel room with view of Hanalei Bay, lanai, outdoor pool, hot tub & grills
Hanalei Bay Resort 9204Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Enjoy Hanalei Bay Resort 9024. This air-conditioned hotel room features a king bed, large bathroom, TV, and a...
Say “Aloha” to Ocean Views, Free WiFi, Modern Kitchenette – Waikīkī Shore 1214
It’s hard to not love this fabulous deluxe ocean view studio. You’ll adore all the upgrades, which were completed in 2014. The kitchenette has new stainless-steel appliances, modern wood cabinetry, and new tile floors. There is a quaint table for two, for casual dining,...
Kihei Akahi C-607: 1BR/1BA with Ocean Views, Private Lanai, and Resort Amenities
This property is hotel zoned, and not being affected by the recent proposed legislation.Kihei Akahi is situated on six and a half acres of beautiful lush tropical grounds, with two great swimming pools, 4 large gas BBQ's, and a tennis court. You have everything you need...
Turtle Bay Condo: Hawaiian Style & Cozy - Kuilima Estates East
Our condo was carefully designed and decorated to provide a cozy, Hawaiian home feel. It is located on the North Shore , Oahu, which is famous for Turtle Bay and it's Kuilima Point. Home to the best of Oahu's beaches, surfing, golfing, horseback riding and more. If you...