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.
Wailea Ekahi Village 50E - Relaxing Ocean and Mountain Views
Welcome to Wailea Ekahi 50E, our deluxe condo for two. We are on the 2nd (top) floor with beautiful ocean and garden views and wonderful tropical breezes. In addition, there are ceiling fans throughout the unit.The large living room-dining room is beautifully furnished...
Hale Makai ~ Gold Coast Comfort - Kuilima Estates West
Welcome to Hale Makai ~ Gold Coast Comfort, your idyllic retreat nestled in the heart of Kahuku, Hawaii. This charming 2-bedroom, 2-full bathroom, and 1-half bathroom vacation rental offers a perfect blend of comfort and style, accommodating up to 4 guests. Step inside...
Beautiful Waikoloa Beach Villa - Spring Dates on Sale!
Our villa is furnished in a casual tropical island theme with hardwood floors throughout. It is ideally located, just steps away from the pool. Our Hawaiian style townhouse is an end unit with windows on all four sides, 17-ft high living room ceilings and no one above...
Top-floor condo with ocean-view balcony, central AC, washer/dryer, & shared pool
Pacific Shores A402Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Tucked amid the mountains and ocean waters, this top-floor condo boasts beautiful views on either side of its...
Ke Nani Kai Unit 156- More Molokai
Enjoy the tranquility of Molokai with modern-day luxuries and all the comforts of home If the quiet solitude of Molokai has left you wanting more, then look no further... This 2-bedroom/2- bath condo has been fully renovated to give you the vacation of your dreams....
Kapaa Shore Resort A305, Oceanfront, Near Shops, Restaurants & Beaches
Kapaa Shore Resort A305 – Oceanfront Kauai Condo with Stunning ViewsEscape to the beauty of Kauai’s Coconut Coast at Kapaa Shore Resort A305, a newly updated oceanfront condo offering breathtaking views and luxurious Hawaiian living. Located on the top (3rd) floor...
Relaxing Ocean View Condo in Kauai | Pono Kai Resort | PK-E102
Pono Kai's pool and spa will be closed January 6-31, 2026 for the instillation of the new pool deck fencing.The Kapaa Public Pool, located less than one mile from the resort, is open to the public.Experience the beauty of Kauai in this charming 2 bedroom, 2 bathroom...
Hanalei Bay Resort Ocean Front Unobstructed Bali Hai View!
Hanalei Bay Resort is a 5 Star Resort and is widely regarded as one of the nicest places to stay on Kauai. 8232 is ideally situated on the 'point' of this 22 acre Resort giving you spectacular views! This 1 bedroom suite w/loft has some of the best views in all of...
Kihei Akahi Condo w/ Shared Grill, Free WiFi-Beaches and Beyond
Kihei Akahi C307Our 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...
Islander on the Beach 232: Beach Resort Room w/ View, AC & Kitchenette
Step into your own little slice of paradise with the quaint Islander on the Beach unit #232 condo! Just seconds from the beach, this eastward facing oceanside studio enjoys breathtaking sunrises on the iconic Coconut Coast of the Garden Isle of Kauai. This unbeatable...
Oceanfront w/Sunset Views Condo at the Colony Surf Full Kitchen and Parking
This property requires a minimum 30-day rental. Book with confidence—professionally managed by Ali'i Beach Rentals, an award-winning property management company.The Colony Surf is located at 2895 Kalakaua Ave.This fully furnished Colony Surf studio accommodates 2 and...
Hale Kai O Kihei Condo w/ Free WiFi, Shared W/D-Near Everything
Hale Kai O Kihei 106Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'This Hale Kai O’ Kihei condo offers a breathtaking ocean view from every room and includes a private lanai that...
Charming & Affordable Couple's Retreat w/ Ocean Views from Every Room
Sealodge E8 offers the perfect blend of classic island charm with modern touches! This intimate and inviting condo features a queen bed, as well as a twin-sized punee (Hawaiian day bed) in the living room that's perfect for sleeping a child if you're a small family. The...
Ocean view condo with lanai, WiFi, W/D & oceanfront pool/hot tub/BBQ area
Sea Village #3202Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Take in fragrant island breezes, the sounds of rustling palms, and a partial view of the Pacific Ocean from your...
Unbeatable Ocean Front Condo | Pono Kai Resort | PK-C302
Pono Kai's pool and spa will be closed January 6-31, 2026 for the instillation of the new pool deck fencing.The Kapaa Public Pool, located less than one mile from the resort, is open to the public.Unbeatable Oceanfront Condo – Your Perfect Paradise Getaway!Welcome to...
@ Marbella Lane - 3BR w/ amazing MT & Ocean Vistas
Summary:Make your stay memorable in this stylishly designed 3-bedroom home, situated in a gated community in the heart of the Makaha Valley. This comfy home is graciously appointed at the foot of the Wai‘anae Mountain Range feasting you with the marvelous ocean and...
OUTSTANDING Main Floor Condo - STEP directly onto the BEACH!!
WELCOME to the Makaha Beach Cabanas located on the northwest shores of Oahu! Our condo is on the Main Floor. No need to even use an elevator - step off our Lanai directly on the Beach! It really doesn't get better than this! Far from the hustle and bustle, we're in the...
Oceanfront Villa at Alii Point - AC & Private Pool
Please note, effective Jan 1st. 2026, Hawaii`s Transient Accommodations Tax will increase from 10.25% to 11% for all stays with an arrival in 2026 forward. We may need to collect the tax difference to secure and finalize your booking. We will contact you to confirm the...
Polo Beach Club 305, you will be drawn to the breathtaking views from lanai.
Polo Beach 305, with Spectacular Ocean Front Views! Located in the highly sought after beachfront stack. Take in an unforgettable sunset or views of Kaho'olawe, Molokini, and The West Maui Mountains!As you enter Polo Beach Club 305, you will be drawn to the breathtaking...
KS 819 Spacious Kaanapali Shores Condo w Ocean Views AC Pools
Kaanapali Shores 819 Spacious 1Bedroom Kaanapali Shores with Ocean Views & Central AC KAANAPALI SHORES IS A HOTEL ZONED LEGAL VACATION RENTAL PROPERTY FREE daily activities included with your stay value up to $570! Complimentary admission, every day of your stay*: Whale...
Cozy Waikiki Vacation Rental with Partial Ocean Views - Great for families!
As of January 1, 2026, Hawaii will increase its Transient Accommodations Tax (TAT) rate by 0.75%. For reservations booked before January 1, 2026, an additional payment request will be sent for the 0.75% tax increase.This is a legal conforming vacation rental. Please see...
Classy Waikiki Studio
Classy, Clean & City CenterJust a short 2 blocks walk to the beach! Conveniently situated at the entrance to Waikiki, across from Ft. DeRussy Park and Hilton Hawaiian Village. Walk to the biggest shopping center (Ala Moana Center) and get easy access to main buses to go...
KS 836 Studio in Kaanapali Shores w Pools AC
Kaanapali Shores 836 Spacious Studio at a Beautiful Oceanfront Resort in North Kaanapali. Unplug, Relax, and Recharge with Pools, Hot Tubs, Restaurants, and White Sand Beach FREE daily activities included with your stay value up to $570! Complimentary admission, every...
Maui Tropical Getaway w/ Ocean View, Full Kitchen, Pool, A/C, WIFI, King Bed
Your stay location is 25 miles south of Lahaina. The Kihei / Wailea area has not been impacted and is open to all, including travel, lodging and activities.PRIME BEACH LOCATION:Look no further than Haleakala Shores, #A-102 for your Maui Hawaii vacation rental. This two...
Just Another Amazing Day in Paradise! Ocean View, AC, 5-min. walk to beach!
Waikiki Park Heights #1508 – 2440 Kuhio Ave.(30-Night Minimum. ALL MONTHLY RESERVATIONS ARE SUBJECT TO APPROVAL.)You deserve many wonderful days in paradise and what better place than this beautifully renovated condo with great ocean views and central AC! (488 sq.ft....
Kamaole Sands -inner court - ocean views- Remodeled
Unit 6304. Wonderful views and on the third floor.Please come and stay you will love it!Totally remodeled with new solid granite kitchenLuxury planking floors in the living room and. bedroom Brand new Sealy King size bed in Master bedroom Smart new 65" flat screen TV in...
Kona Shores#130 Beautifully Remodeled Ground Floor Condo w/AC!
Kona Shores#130 is a spectacular ground floor condo at an Oceanfront Condominium Complex. Kona Shores is just a mile to all restaurants, cafes and shopping within Kailua Village. From the oceanfront Pool and BBQ Area you will be able to enjoy the famous Kona Sunsets, as...
Fun in the Sun at Maui Sunset-Ocean View 1BR/2BA
The Maui Sunset is located on over 5 acres of ocean front in Kihei, which is considered one of the best locations on the Valley Isle. Kihei is noted for its year round sunshine, balmy trade winds and soothing evening air. It is one of the driest and sunniest areas on...
Maui Sunset B218 ~ 2 Bedroom Beautiful Ocean Views, Full Kitchen
Relax and unwind in this tastefully done Hawaiian Island style 2 bedroom / 2 bathroom condo. Feel the spirit of Maui as you watch the spectacular Sunsets, and whale watching during the whale season from your Lanai. Maui Sunset grounds are immaculately groomed with...
OCEANFRONT 2 bed/2bath West Maui condo on Napili Bay! Napili Point C12
Experience the beauty and tranquility of West Maui at Napili Point, a premier oceanfront property perched above the turquoise waters of Honokeana Cove. This well-appointed two-bedroom, two-bathroom condo offers panoramic views of the Pacific Ocean, Molokai, Lanai, and...
Beachfront on Kauai's Beautiful Coconut Coast!
This charming, oceanfront condo is attractively furnished with your comfort in mind. Its ground-floor location offers convenience as well as easy access to the beach. You have nice ocean views from your living room and master bedroom as well as from your private lanai....
Budget Friendly - Kihei Akahi C-608, Ocean Views, Short Walk to Kamaole Beach II
Step into Kihei Akahi C-608, your dream island retreat, where every detail is designed to create the perfect Maui vacation experience. This top-floor, 1-bedroom getaway offers serene ocean views, upscale comfort, and a welcoming space for both relaxation and adventure -...
420123 Hanalei Bay Resort 3br 3ba Sleep 8 Absolutely Gorgeous View
Hanalei Bay Resort 420123 3 bedroom sleeps 8Vacation Rental Tax Number GE/TA #049-852-4160-01TMK 4540110030016(Special Permit – SP-2011-18) (TVNCU 4198)Jan 22-Feb 2, 2025 Units 4022 & 4203 available with King Bed & 2 Double Beds can sleep 6NO EXTRA COSTS for early...
Steps to beach, pool, garden. April/May Cancellation Special. CALL NOW!
Minimum 30 day rental, this 3 bedroom, 3 bath with a private pool is the perfect location to relax and unwind. The entire property is surrounded by lush landscaping, beautiful palm trees and tropical flowers. The spacious yard is perfect for sun bathing, barbecuing or...
Poipu Shores B202: Beautiful Oceanfront Condo on Kaua'i's Pristine South Shore
Beautiful two-bedroom oceanfront condo on Kaua'i's pristine South Shore. This remodeled Poipu Shores unit is equipped with a full kitchen, air conditioning, and Hawaiian style furnishings. Relax at Poipu Shores' oceanfront pool, enjoying the gorgeous views, or take time...
🏖️Beautiful Ocean View | Updated | WIFI Included | vrKCV
vrKCV - Casa de Emdeko 216, Professionally Managed by Kona Coast VacationsEnjoy stunning ocean views from the private lanai of Casa 216! This 2nd floor condo is the 4th unit from ocean front! The covered lanai is the perfect place to watch whales and spinner dolphins,...
DOWNTOWN KAILUA-KONA AC, FREE WIFI, FREE PARKING, Historic Kailua-Kona Village
Aloha and welcome to Unit #110 Hale Moana (Moh-ah-nah)! This bright and airy studio apartment was freshly remodeled in 2019 and recently updated with new furnishings in April 2021. It is conveniently located in the heart of downtown Kailua-Kona. Our studio is the...
Special Rate! Ground Floor at Royal Sea Cliff, Central AC!
Royal Sea Cliff is an architectural wonder that sits on the pristine Kona Coast. If you are looking to be close to town but feel away from it all, this is the place for you to make your Hawaii memories. This one bedroom, one bath is the perfect oasis to enjoy your...
*Luxurious & Remodeled *Complex is OCEANFRONT*
*Please Note the Lanai / balcony in the property is not accessible, however make sure to take advantage of the gorgeous one of a kind 360° wrap around views just a 60 second walk from the property on the complexes rooftop or enjoy the ample grassy area around the...
Paradise in Puamana just steps to the Pacific Ocean 4 king beds
Puamana 177-1 is like staying at a Hawaiian home. Living area is 1250 SQ FT with 220 SQ FT of front and back lanai’s and an added-on room to the rear of unit that provides a 3rd bedroom at night. It has an 800 SF backyard and 300 SF front yard which includes a unique...
Kona Plaza#202 2ND FLOOR OCEAN VIEW IN HEART OF KONA TOWN! AC & Elevators!
Knutson & Associates Property Management is proud to be representing Kona Plaza#202. Best location in the development! Highly desirable west facing with Ocean views! Best location in all of Kona Plaza. Its amazing location puts you right in immediate walking distance to...
VI 902 BeachFront Condo w Sunset and Ocean Views Pool
Valley Isle 902 Amazing Ocean View at Beachfront Resort 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...
Ocean View KAN106 - Maui Beach Front, Lovely & Charming Ground-Floor Condo
Looking for a tranquil oceanview condo for your vacation in Maui, Hawaii? Look no further than Kanai A Nalu #106. This 2 bedroom/2 bath unit is fully furnished and can comfortably accommodate up to 4 guests. With a serene master bedroom, fully equipped kitchen, and...
Villa 114: 2 sets of bunk beds at Turtle Bay!
Our Villa is Located at the Ritz Carlton, Oahu Turtle Bay Resort! You can use the Ocean Villas pool and Jacuzzi, park for free, and pay no resort fees! You can also use most of the Ritz Carlton, Oahu Turtle Bay amenities for a fee. You have FREE access to the 12 miles...
KA 409 OceanFront Condo w Ocean Views Heated Pool AC
Kaleialoha 409 Convenient Location Steps Away From the Pacific Ocean 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...
KBM Resorts | FREE CAR | Honua Kai Konea | Ocean view | 2-Bedroom Condo with Huge Lanai, Corner Villa! HKK-234
** 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...
Beautiful Second-Floor Studio w/Free WiFi, Private Balcony + Shared Pool/Hot Tub
Islander on the Beach 257Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'With partial ocean views from the furnished private balcony, this lovely second-floor studio is a terrific...
Kapaa Shore Resort A309, Oceanfront, Walk to Shops, Restaurants, Beaches
Kapaa Shore Resort A309 on the Coconut Coast, in the heart of Kapaa Town, Kauai Vacation Rental.*Two bedrooms, two bath, oceanfront, 3rd (top floor, no elevator) unit with washer and dryer in the unit.*King bed in the upstairs loft bedroom with private bathroom and...
Hale A Kai: Big Island Home w/partial Ocean view, AC &WiFi
Hale A Kai by Gather or Home by the Sea translated from Hawaiian, is nestled at the end of a quiet neighborhood cul de sac. This recently updated four bedroom, four bath home, is aptly named due to its proximity to the ocean, located just minutes away. The...
NEW to Our Inventory! FULLY RENOVATED! Modern Condo in the Heart of Waikiki!
Niihau Apartments #203 – 247 Beach WalkFULLY RENOVATED! Welcome to your home away from home! This newly remodeled (2023) condo is the perfect launching point to explore all that Waikiki and Oahu have to offer! FREE Wi-Fi and parking at nearby lot. Secured...