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.
Plantations at Princeville unit 111
Welcome to your private oasis on the north shore of Kauai. Nestled within the upscale Plantation at Princeville complex, our corner unit 111 offers unparalleled privacy and breathtaking views.Immerse yourself in the beauty of the Hanalei Wildlife National Reserve,...
Beautifully Updated & Fully Air Conditioned - Prime Location w/ Huge Lanai
Mauna Kai 5A offers the perfect combination of comfort, style, and an unbeatable location on Kauai’s North Shore! This beautifully remodeled, fully air-conditioned townhome is ideal for those looking for a peaceful and relaxing getaway, without sacrificing...
Gorgeous, remodeled 3 bed/2.5 bath Ka'anapali Plantation
Welcome to your private island sanctuary—a stunningly remodeled 3-bedroom, 2.5-bathroom villa set within the lush, gated grounds of Ka’anapali Plantation, one of West Maui’s most exclusive low-rise communities. Perfectly positioned between world-class golf...
Kihei Akahi Condo w/ Shared Pool, A/C-Snorkel, Surf, Swim
Kihei Akahi C418Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Step across the street and enjoy Kamaole Beach Park II, one of Maui’s best swimming and stunning beaches. Revel in...
Professionally designed new unit at Kiahuna plantation with A/C
Kiahuna plantation unit 427 in bldg. 41.You are a very short walk away from a beach, actually 200 steps.On the middle floor. Poipu beach is very nearby.Welcome to Sunny Poipu and Kiahuna Plantation Beach! This newly remodeled A/C .Kiahuna Plantation leaves nothing to be...
Affordable total comfort Studio at 1 of Waikiki's Top Locations, Pool & Wifi
Located in Honolulu & with a beautiful Pool, this charming studio is a dream. With a cozy living room featuring a queen bed and sofa bed, guests can unwind after a day of exploring. The bathroom offer a relaxing bathtub /shower combo with hair dryer for added...
Great 2bd condo on iconic Sugar Beach
Kihei Sands B2 is a 2-bedroom, 2-bathroom condo located on the 2nd floor that offers a three-split air conditioning system - one in every room and can accommodate up to 6 guests. Access to the second floor is by stairs only; this low-rise complex does not have an...
Luxurious Wailea Condo | Ocean Glimpses & Modern Living Palms 604
Experience the perfect blend of luxury and comfort in this beautifully updated 2-bedroom, 2-bathroom condo at the prestigious Palms at Wailea. This spacious retreat features a modern open-concept living area, plush king beds in both bedrooms, and efficient ductless AC...
Hale Maluhia Villa O-603 the perfect getaway
Welcome to Hale Maluhia, O-603, your serene retreat in the heart of paradise. Located on the 6th floor of the Beach Villas at Ko Olina, this exquisite two-bedroom, two-bath villa offers unparalleled comfort and luxury for up to four guests. Upon entering, you'll find a...
Luxury Ilikai 2-bedroom 2-bathroom Unit NO RESORT FEES! FREE WIFI
Best 2-bedroom, 2-bathroom city view Ilikai unit!Great deal for a world-famous Ilikai unit over 1000 s.f. with two lanais to enjoy some cool ocean breeze.It is tastefully furnished with all you need for a comfortable stay in paradise.The Master bedroom has a king bed,...
Reduced Rates for a Private Getaway In Tropical Oceanview Princeville Villa
Welcome to Your Private Island Oasis | Hanalei Bay Villas, PrincevilleTucked in one of Princeville’s premier locations, this detached villa at Hanalei Bay Villas offers the perfect North Shore escape. Enjoy easy access to world-class beaches, scenic walking trails,...
Studio apt. with A/C, Fridge, Semi-Private pool in the Center of kihei
This is a fourth floor studio apartment, with full bathroom, near the center of Kihei. Includes A/C, fridge, coffee-maker, microwave, as well as cable TV and wireless internet. We are walking distance to the grocery store, bars and restaurants, and the beach, as well as...
Coastal Condo Retreat - Exquisite Views. Short Walk to Beaches. Tennis Courts!
This perfectly positioned condominium with private lanai will inspire your sense of adventure as well as be your space for relaxation! Support Maui's economic recovery by building your book of vacation memories in central Kihei close to everything you want to do! The...
Luxury Ocean Marina View Studio World Famous Ilikai NO RESORT FEES! FREE WIFI
This much-desired marina ocean view unit has great unobstructed views of the ocean and marina. You can enjoy this breathtaking view on the 120 s.f. Lanai, which has a table and chairs for meals or rest.The unit is in great condition with brand new Pergo, travertine...
Waikiki Banyan Bliss: Ocean View & Walk to Beach!
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...
Wailea Ekahi Village | 15A
Walk to the beach in minutes from this ground floor condo at Wailea Ekahi Village. Slide open the glass lanai doors of Wailea Ekahi 15A and you will quickly be out on the manicured grass lawns surrounded by palm trees, plumeria trees, and colorful hibsicus. Feel the...
Spacious Ground Floor Revitalized Oasis- Discover Wailea Ekahi #22B
Wailea Ekahi #22B – Ground-Floor Elegance with Ocean Breezes and Garden ViewsStep into comfort, space, and tranquility at Wailea Ekahi #22B, a large and light-filled 1-bedroom, 2-bathroom ground-floor retreat just a 2-minute stroll from Keawakapu Beach, the oceanfront...
Luxe, 2-Level Condo with Mountain View, Lanai, WiFi & On-Site Pool/Hot Tub/Golf
Pili Mai 1EOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'You'll be immersed in the sun-splashed, tropical beauty of Kauai's South Shore at Pili Mai 1E, a luxe, two-story escape...
Beautiful Princeville Island Style Townhouse! Walk to Beach! High speed WiFi
This spacious 2 bedrooms + Loft, 2 baths extra bright Kauai Princeville Townhouse is tastefully remodeled and decorated, it’s crispy clean and ready for you to enjoy it. Conveniently situated as an end-unit, the two-story Townhouse takes advantage of the reviving...
Beautifully upgraded condo in Maui Vista steps from world class beaches.
Aloha! We are happy to share our gorgeous, bright, clean and well-equipped vacation home with you. One bedroom with one queen bed, one bath and a sofa bed (sleeps four). Maui Vista is just steps from Charley Young beach. This quiet unit is located in the 2nd...
Spacious lanai and newly remodeled. Shores at Waikoloa 317
This vacation rental is professionally managed by ResorticaHawaiiShores at Waikoloa 317. Newly remodeled!Please scroll down for detailed informationBedding Configuration:Master Bedroom: King BedLiving Room: Sleeper Sofa and Twin Size Fold Out Sleeper ChairBeach...
Waimea Bay Luxury Estate Views & Hot tub
Summary:Immerse yourself in the ultimate Hawaiian experience at Waimea Bay Luxury Estate, located on a corner bluff lot in the peaceful neighborhood of Pupukea on Oahu's North Shore. This expansive estate boasts breathtaking ocean views from every angle and is just...
Junior Suite Oceanfront #302
This is a lovely Studio featuring a Queen sized Murphy Bed. The bed is easily placed into the wall to expand your living space if you so desire. One of Maui Kai’s little gems is unit 302. In colorful, floral designs, this room presents itself as a bright, airy part of...
Large Roof Balcony (1,385 Sqft)!! Comfortable 2 Bedroom at Waikiki! (LW14)
Step inside of a spacious 2bed-room you will be astonished by the amount of sunlight beaming through the floor to ceiling windows. You will quickly notice the clean and modern feel of the space, with Waikiki's skyline as a backdrop!The warm and inviting air of your...
Enjoy Ocean Views From Lanai, Living room & Bedroom, Beachfront Pool!
Address for this Condo:938 S. Kihei Rd #324, Kihei HI 96753***Professionally Cleaned Condo, No-Contact Check-In/Check Out*** ***New Mattresses IN Bedroom And Sleeper Sofa Aloha & Welcome to our mid-century modern Maui condo. We invite you to stay and enjoy the peaceful...
Bright, modest studio with fully equipped kitchen
Welcome to Kihei Bay Surf Resort, a studio located in the beautiful North Kihei region of Maui, just a short 15-minute drive from Kahului Airport. This condo features a comfortable queen-size bed and a queen-size sofa bed in the living room to accommodate additional...
Ground-floor condo steps from pool - hot tub, tennis, beach access
Maui Kamaole C110Our 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...
❤️PiH❤️ Aloha Shores ★ 2024 Hilton Resort Passes ★ Pool & Waterfall Spa
Brought to you by Paradise in Hawaii Luxury Homes.Welcome to the newest elegant home, Aloha Shores, in our Hawaiian Luxury Collection. Aloha Shores is a wonderful new large single level 4 bedroom, 3 bathroom home. This home has one of our largest private pools and...
🏖️🌸 STUNNING Ocean front Views! 2 Mstr Bdrms/2 Bths 🏝️🌺
Best of island 250 degree view. You are so close to the beautiful turquoise ocean you can toss a coin into it! The first thing thing you see in this NON SMOKING CONDO & RESORT, 2 bdrm/2bath, is the amazing ocean and islands of Lanai and Molokai with views that wrap...
koolkondo 2283 Hoohu Rd Oceanview, KoolKondo 2283 Hoohu Rd Oceanview
The Emerald Pagoda: Luxury Vacation Rental in Kauai with Ocean View and Pool2283 Ho’ohu Rd., Koloa, HIWelcome to koolkondo, where you will experience luxury vacation rentals at their finest. Our stylish boutique hotel style condos and homes have it all. You will...
Ko Olina Beach Villas O521: Luxury Ocean View, 3 Bedrooms & Grand Lanai
Welcome to Ko Olina Beach Villas O521 by Gather, an exquisite luxury home nestled in the renowned Ko Olina Resort, offering an idyllic Hawaii escape. This beachfront villa with its stunning views is the epitome of island living. This three bedroom, three bathroom villa...
Oceanfront property with amazing view, clean & quiet end unit
Aloha! Our condo is a 1 BR/1 BA clean and quiet end unit with an amazing ocean view! We understand that the importance of cleanliness has never been more critical. Rest assured that our unit has been professionally cleaned and sanitized so that you can enjoy a peaceful...
Hale Kamaole 245 Second floor condo, easy access to best beach on Maui!
This two bedroom corner unit with loft has an Ocean View from the living room & kitchen. Additional side window provides extra light. There is a King bed located in the master bedroom, the loft is enclosed with a queen bed, and the downstairs bedroom provides 2 twins...
Wailea Grand Champions Unit 33: Large 2 Br Condo in Wailea Sleeps 6 guests
*New Furniture throughout!! This two-bedroom, two-bath garden-view condo has just been remodeled with all new furniture throughout each room in the condo. The primary bedroom and the guest bedroom both have Cal-King beds plus the living includes a queen sofa sleeper...
2025 Waikoloa Hilton pool pass included 6 guests daily, available through 2025!
Waikoloa Beach Resort provides comfort and relaxation. Located in the resort right across the street from the Queen and King shops. Walking distance to the beautiful Pacific Ocean, A-Bay provides great clear water for all types of water activities with pure clean sand...
Maui Vista 1421: 2 Br w/partial ocean views near Kamaole Beach Park I
Beautifully remodeled and renovated partial ocean view condo. This two-bedroom unit sleeps up to six people with a king in the master bedroom, two twins in the upstairs loft bedroom and a pull-out sofa bed in the living room. The kitchen has been renovated with new...
Awesome Ground Floor! Easy Beach access and Just Steps to Ocean #103
ALOHA AND WELCOME TO HALE KAI # 103Located right on the ocean on the beautiful island of Maui, our condo can be your _home by the sea_. Comfortably decorated with tropical Hawaiian furniture and artwork, our unit will provide you with all the comforts of home, including...
KONA MAKAI#5-205 BEAUTIFUL 2ND FLOOR UNIT IN OCEANFRONT COMPLEX!
Kona Makai#5-205 is a fantastic option for your Hawaiian Vacation. Gorgeous Luxury Vinyl Plank Flooring Installed throughout Living Areas/Bedroom. No Carpet! This beautiful 2nd floor unit is located in a very accessible spot of Building#5 at the Kona Makai. Don't have...
Ocean View! 2 Br 3 Bath Condo In Town!
Relax and enjoy Kona Coffee on your private, ocean view lanai, watching whales, spinner dolphins & awesome sunsets. This corner (end unit) overlooks the pool and BBQ area of Kona Pacific which also offers a sun deck with ocean view and reading/gathering room.The condo...
🏖️Excellent Ocean View | AC | Concierge Included | vrKCV
vrKCV - Kona Makai 6204, Professionally Managed by Kona Coast Vacations.Experience Oceanfront Living at Kona MakaiNestled along the lava rock shores of Kailua-Kona, Kona Makai offers the perfect blend of island charm and modern comfort. This second-floor, one-bedroom...
Oceanfront -Waterview 1 BedroomCondo Heart of Town at Kona Plaza walk to Ironman
A GORGEOUS Fully equipped 1 bedroom condo in the Heart of beautiful Kona.Nicely decorated, newly done Kitchen and Bath, with a new full-sized washer and dryer. This 1 bedroom unit has a huge comfortable King bed a, a pull-out queen(outside), and a new comfy trundle bed...
Time to Spoil Yourself! Deluxe Ocean Front and Steps to N. Kaanapali Beach ~
Almost ocean front on Kaanapali Beach. Our 2 bedroom, 2 bath condo is one unit back from being direct ocean front. Being ground floor allows for easy access to pool and beach. Enjoy amazing Maui sunsets from our lanai. Tastefully furnished and ready for occupancy. Enjoy...
Mauna Lani KaMilo Home 424
This stunning property is now accepting longer-term stays at reduced rates. Please inquire for details.This spectacular three-bedroom, three-bath single-level home enjoys an ideal location within KaMilo, in the heart of the Mauna Lani Resort area. Nestled into a gated...
Enjoy a nice view of the ocean from this 2 bedroom extended floor plan villa!
Kolea 9L offers a nice view of the ocean along with close proximity to the Kolea Beach Club and the white sand beach at A'Bay. The villa has been nicely furnished to offer the utmost comfort in a vacation home.The extended floor plan offers ample living space as well as...
North Shore Tropical Studio with breathtaking mountain views!
This beautiful studio apartment with stunning mountain views is a perfect place to unwind for your North Shore get-away. The studio features a queen bed with additional twin bed, and it sleeps up to 3 people. There is air conditioning which you are welcome to use to...
STUDIO: Kalama Beach Park, South Maui Gardens, Food Trucks, Hula Shows, Luaus
🌺 The Island Surf is located in the Heart of South Maui. For guests that do not want to spend a fortune in hotel bills, but want a clean affordable place in a great location. Many guests feel no need to rent car. Speedi Shuttle runs from OGG to Island Surf.You can...
A 'Spa feel' at the Diamond Head Beach Hotel
Legally permitted vacation rentalDiamond Head Beach Hotel🕉2947 Kalakaua Ave 303⚕⚕For your health and safety⚕⚕We utilize additional Sterilization procedures between reservations.Whether for business or pleasure the delightful attention to detail...
The White Lotus Oceanfront Hale
Where PEACE and PARADISE flow together. A RESTORATIVE Retreat has been created for you on the Garden Island of Kauai. Every detail has been thoughtfully prepared. The Calm ENERGY combined with the Breathtaking Ocean Views is what sets this location apart from the rest....
Hale Malie - Mauna Kea Family Home with Stunning Ocean Views
Behold the most breathtaking view of the Kohala coastline! Hale Malie is a charming Hawaiian vacation home, featuring stunning ocean views, 3 spacious bedrooms, and 3 bathrooms in the exclusive Fairways South community at Mauna Kea Resort. This classic Mauna Kea home...
Top-floor beach condo - partial ocean views - steps to beachside pool & hot tub
Islander on the Beach 370Our 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...