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.
Colorful condo with lanai, W/D, on-site outdoor pool, tennis, hot tub, gas grill
Nihilani 32BOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'If you're looking to spend quality time with the ones you love, look no further than this cozy condo in Princeville,...
Blue Sky Escapes Vacation Home w/ big Oceanviews, Pool, Jacuzzi, 5min to beach
Come stay at my Blue Sky Escapes Maui Vacation home! Located in sunny south Maui the home is a beautiful, remodeled ocean view home with private pool swimming pool. This property is extremely private with no other rentals on property located in Maui Meadows a hillside...
Unbeatable Location at Kamaole III Beach - Kam Sands Bldg. 1
This third floor, perfectly located, inner courtyard condo in Buildin #1 has a highly desirable single level floor plan. Situated at the end of the building, this unit offers increased privacy and views, with an extra window to watch the sunrise over Haleakala. The...
Ocean View, Fully Remodeled, New A/C, Walk to Beach
Across the street from one of Maui's most beautiful beaches. Perfect for families. Relax on the lanai (patio) and feel the cool island breeze as you gaze over turquoise waters. Take a short walk to the beach to relax, swim, snorkel, read, and soak up the sun and views....
Panoramic Ocean Views Remodel - FREE Parking/Wi-Fi, AC, Washlet, Sleeps 6
Ilikai #1944 – 1777 Ala Moana Blvd.Enjoy luxurious high-end ocean-view living in this beautiful condo at the world-famous Ilikai, made famous by Hawaii Five-O. This 19th floor corner unit has magnificent views of the Pacific Ocean, Duke Kahanamoku Lagoon, and Waikiki...
Beachfront Condo W/ Unbeatable Ocean Views! Floor To Ceiling Windows & Lanai!
Address for this Condo: 800 S. Kihei Rd #505, Kihei HI 96753***Professionally Cleaned Condo, No-Contact Check-In/Check Out*** Koa Lagoon is an oceanfront condominium complex located in North Kihei with spectacular panoramic views of the Pacific Ocean, the other islands...
Feb special Beautiful Beachfront 1/1 condo on the beach with free parking & W/D
Sugar beach Resort unit# 336 is on the third floor. It has wash and dryer in the unit and free parking on the property. The property is perfect for watching the humpback whales play during the winter months and each evening as the Maui sun sets off in the distance. The...
KAS 10203 1BD Condo w Ocean Views Across From Beach
Kamaole Sands 10203 Make Magical Maui Memories at Remodeled Kihei Home Across the Street From Beach Located Near Shops and Eateries FREE daily activities included with your stay value up to $554! Complimentary admission, every day of your stay*: Whale Watching...
Ocean View Top Floor Free High Speed Internet
Experience the essence of paradise in our top floor unit. Lush tropical grounds surround two swimming pools and a tennis court. The smell of tropical flowers drift on the wind from over 50 different varieties of vegetation. Our view extends from South Maui to the exotic...
4Br Princeville Home, AC, Pool, Tennis, Private Yard, Beach Toys, Sleeps 10
Adventure Awaits on KauaiWhether you're surfing the North Shore waves, playing golf at the Princeville resort, or hiking the NaPali coast, you'll find this modern and luxurious property the perfect home base for all your adventures on the Garden Isle of Kauai. Ideal for...
KKSR5203 DIRECT OCEANFRONT, 2ND FLOOR, SPECTACULAR REMODEL, ONE OF THE BEST!
Keauhou Kona Surf & Racquet Club #5-203 is hands down one of the nicest remodels in the entire development. Step into a dream come true! This second floor, 2 bedroom, 2 bath offering is THE premiere unit in one of Kona's finest oceanfront complexes. Located in Building...
Gorgeous renovated 3-Bedroom Oceanfront Condo!!
A few short steps from the semi-private, white sand Kahana Beach lies the Kahana Outrigger Resort. This resort is located oceanfront along the West Maui shoreline, situated centrally between the renowned Ka`anapali and Kapalua Resorts. A quiet and family-friendly...
Spacious 1BD Ocean View Golf Villa with A/C
Welcome to Kapalua Golf Villa 20T5, your refined escape on Maui's spectacular northwest coast. Nestled on the terrace level of the prestigious Kapalua Golf Villas—no stairs required—this stunning one-bedroom, two-bathroom villa was completely transformed in 2013...
+DIRECT OCEANFRONT+GROUND FLOOR 1-BEDROOM A109+ SPLIT A/C+FULLY EQUIPPED+
We have loved vacationing at this resort for years, and are very grateful to have the opportunity to share our Maui home. Papakea is a low density, oceanfront resort, located on 13 tropically landscaped acres, 1 1/2 miles north of Black Rock on Ka'anapali Beach. Our...
Maui Resort Rentals: Honua Kai Konea 609 - Expansive 6th Floor Interior Courtyard 2BR w/ Stunning Ocean Views!
Konea 609 is an expansive 2 bedroom ocean view suite at Honua Kai. Its 6th-floor location offers stunning ocean views , high enough to avoid the palm tree blockage that affects lower floors. This prime interior Konea Tower location is one of the most sought after areas...
WBH D115 Aloha Kai2 – Garden View Suite by the Sea
Summary:This family-friendly remodeled beachfront, ground floor 1-bedroom/ 1-bath air-conditioned Condo Suite comes with a comfortable king-size bed and living room couch that pulls out to a queen size sofa-sleeper (8.5" mattress) allowing the unit to sleep up to 4...
Ocean Front! Kona Alii #402
Ocean Front in the heart of historic Kailua-KonaKona Alii #402Bedroom Configuration:Master Bedroom: King Bed Living Area: Full Size Cabinet Fold Out BedLiving Area: Sectional Couch (not fold out) Amenities:Beach Equipment: All of our vacation rentals include beach...
Holua Kai #26: Luxury Fairway Front Villa w/ Pool, Spa, Lanai, AC & Ocean Views
Holua Kai #26 is a two-story, plantation-style retreat in the gated Holua Kai at Keauhou community, overlooking the 2nd hole green of the Kona Country Club’s Makai Golf Course with glimpses of the Pacific from its expansive covered lanai. This 2,685-square-foot...
Steps Away from the Beach in This Premium Oceanfront Condo - SENIOR RATES AVAIL.
SPECIAL RATE FOR SEPTEMBER, OCTOBER AND NOVEMBER 2025 - $190./NT FOR ALL (2 persons; add $50./nt for additional guests) Keywords: New AC with cold plasma air purification device, medical grade air purifier in bedroom, ground floor condo, located on 12 beachfront acres,...
Great Rates - Clean and Cozy Condo!
Come relax in this clean, quiet, and quaint studio condo.Kihei Bay Surf is a 2-story, 7 building complex, with 118 total units in a tropical setting. The 7 buildings are built around a central courtyard that includes a swimming pool, hot tub, 2 tennis courts, and a BBQ...
Clean, Ocean Front, Large 1 Bd, 1st Floor, Royal Kahana
Lovely one bedroom home conveniently located on the first floor of the Royal Kahana Resort with a view of the ocean and pool from the lanai. This oceanfront resort is one of Maui’s best-kept secrets. We clean and sanitize the property before each guest arrives. The...
Beachfront Palaypa - Former Mission House
Direct beachfront at Sunset Beach. Incredible views to Kaena Point. Watch the sunsets from your covered lanai. World class surf break right in front of the house. Pumping surf in the winter, glassy and calm in the summer.This charming cottage has everything you need for...
Maui Resort Rentals: Honua Kai Hokulani 144 – Large Ground Floor 1BR, Spacious Lawn Area + Easy Pools/Beach Access
Hokulani 144 is a premier ground floor suite with one of Honua Kai's largest one-bedroom floor plans and easy access to the pools, beach, and B.B.Qs mere steps away! Enjoy the extra space to spread out on the partially secluded adjacent lawn area. Take in the views of...
Kihei Akahi C405 Beautiful Ocean and Garden Views
"Escape to Maui and Experience Warm Aloha! Enjoy Last-Minute Deals Through March 2026!".Nice ocean and garden views! 4th Floor comfortable beach home - Building CPlease review the property description and pictures carefully prior to booking, and call/email if you have...
Kiahuna #39 PRIVATE + QUIET! Seconds to beach +ground floor A/C New furniture!
Kiahuna Plantation is the only beach-front property on Poipu Beach. White sands, palm tree shaded grassy areas, state of the art gas grills, complimentary towels and beach chairs and chaise lounges are all standard fare. Relax on the beach or go boogie boarding....
SPECIAL RATE! - All New, Beautifully Renovated 5th Floor Condo, Amazing Views!
PLEASE NOTE: The unit was recently 100% completely renovated including all new furniture, appliances, and amenities, placing it in the highest 'superior' category of all rentals! Summary: This beautiful, exquisitely appointed, 5th floor, ocean-view, one bedroom condo...
Calm island condo with ocean views & pool - walking distance from beaches
Hale Lolo at Poipu KaiOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Escape to Hale Lolo, your gateway to Kauai's paradise! Immerse yourself in tropical bliss with a prime...
❤️PiH❤️ Hawaiiana Escape ★ Hilton Resort Passes ★ Beach Club Access ★ Near Pools ★
Brought to you by Paradise in Hawaii Luxury HomesWelcome to Hawaiiana Escape at Kulalani on the Big Island of Hawaii, a part of our Hawaiian Luxury Collection. Hawaiiana Escape is a wonderful 3 bedroom home in the gated Kulalani community with high-end finishes and golf...
Oceanfront Top Floor Loft-Central AC, Sleep to the Sound of Waves! L-405
Sleep to ocean waves and wake to whales breaching just 25 feet from your lanai. This top-floor penthouse at Papakea is decked in original Hawaiian art and thoughtful upgrades — quartz counters, French-door oven, and a full kitchen built for real cooking. With three...
🏖️Holua Kai 31 | Private Pool | Central AC | Concierge Included | vrKCV
vrKCV - Holua Kai 31, Professionally Managed by Kona Coast VacationsWelcome to Your Tropical Oasis in Keauhou!Escape to this beautifully decorated Hawaiian-themed vacation rental in the heart of Keauhou on the Big Island of Hawaii. With a private pool, hot tub, and...
Great location between Hana Town and Hamoa Beach, private, family-friendly
Hale Nanea is close to everything Hana, yet far enough away that it's private and peaceful at night. The cottage is well equipped and very comfortable with custom Bali furnishings. Enjoy the tranquility of the cottage on the screened in patio or explore Hana's most...
Renovation Complete! One Bedroom, Direct Ocean front -Everything inside is New!
This beautiful, ocean front condo is unit # 322 at the Kaha Lani Resort, which is located on Kauai 's beautiful east shore, the famous 'Royal Coconut Coast'. We just finished a 100% renovation on this condo, and everything inside is new ... - New kitchen cabinets, - New...
Ocean front 1-bedroom house, good location with AC, WiFi
Steps from the ocean. Escape to a cool 1-bedroom house by the Beach. This excellent property features a cozy queen bed, AC, WiFi, and a sofa bed. Guests can unwind in this serene space, just a stone's throw away from the beach. Kick back, relax, and enjoy everything Ewa...
UPPER UNIT -1500 sq/ ft - 30 + days !
Owner hosted - Upper unit. Walking distance to the Magic Sands and Kahalu'u beach park, we are half block off of Ali'i Dr. 1500 sq/ft of comfort and 400+ sq/ft of lanai, three bedrooms and two full bathrooms. A master suite with KS bed and an on suite bath. Bedroom 2...
Ocean-view condo with free WiFi, central ac, lanai, & onsite pool/spa/gym
Pili Mai 13GOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Escape to paradise along Kauai's South Shore at this gorgeous, Poipu condo. Located in the scenic, Pili Mai community,...
Maalaea Kai 2BR/2BA Oceanfront, New Furnishings, Hawaiian Decor, Immaculate
Spectacular Ocean Views at Maalaea KaiClean, well-maintained Maui two-bedroom, two-bath condo away from the crowds, with fantastic views, located in Maalaea Bay with easy access to local beaches and towns. This condo is our second home and before each visitor the unit...
Ocean Front With Stunning Views! Halii Kai 13E
This vacation rental is professionally managed by ResorticaHawaiiHalii Kai 13E. Ocean Front With Stunning Views!Please scroll down for detailed informationBedding Configuration:Master Bedroom: King BedGuest Bedroom: Queen BedGuest Bedroom: 2 Twin BedsLiving Room: ...
Maui Hill 70 - Renovated and Spacious 3/3 - Ocean View Condo - Sleeps 8 - AC!
Maui Hill 70 is a spacious and contemporary 3-bedroom, 3-bath split-level condo located in the best part of South Kihei, just 2 blocks from Wailea. Beautifully updated condo with one of the largest floor plans of any condo in Kihei. Equipped to host three couples or a...
Tropical Gated Oceanfront Estate, Pool, Privacy, and huge ocean view on 2/3 acre
Our very private home, a spacious, 3,500 sq. ft. oceanfront estate, sits on 2/3rds of an acre. It has a large indoor living area, plus an expansive outdoor living area, featuring a 1,000 sq. ft. covered ocean view terrace with a large seating area, a dining table...
Breathtaking Ocean and Yacht Harbor Views! #1788
**Important Notice: Limited Lanai (Balcony)Access**Due to scheduled lanai sealant application, painting, and waterproofing work, the lanai sliding door will be locked and cannot be opened from 12/3-12/23/2025Access to the lanai will be unavailable during this...
Whaler Tower II - 1 Bedroom Condo with Beautiful Ocean View
The Whaler at Kaanapali Beach is situated on the magnificent Kaanapali coast with beautiful beaches and beachfront walking path next to the upscale Whalers Village with high-end shopping, dining and the famous Hawaiian gem Black Rock. It is an oasis of tranquility over...
OCEANFRONT GROUND FLOOR TWO BED CONDO AT MAALAEA KAI
GROUND LEVEL TWO BEDROOM, TWO BATH CONDO ON GROUND LEVEL WITH STUNNING VIEW OF OCEAN. UPGRADED KITCHEN AND BATHROOMS. IN UNIT LAUNDRY AND AIR CONDITIONING. MASTER HAS A CALIFORNIA KING AND SECOND BEDROOM HAS A QUEEN AND XL TWIN. PERFECT FOR TWO COUPLES OR A FAMILY. CAN...
Kauai Exclusive - Waipouli Beach Resort E401
The number one place to stay on the East Shore of Kaua'i is the Waipouli Beach Resort and Spa. Located in Kapaa, this World Class Resort has a central location with easy access to everything that you will want to see and do. Plus, it provides a luxury experience with...
GROUND FLOOR-KAMAOLE SANDS-LARGE LANAI-NICELY UPDATED-AC-METICULOUS CLEANING
Book with confidence, this nicely updated 1 bedroom, 2 bathroom (818 sq ft.) condo at Kamaole Sands. This condo is managed by PMI Maui, a local Real Estate Brokerage that specializes in vacation rentals. We are located within a mile of the resort and available 24/7....
Wailea Ekahi Village 29B - 2 Bedroom Ocean View Condo
This beautifully remodeled first-floor suite combines two separate condos into one expansive unit, offering a luxurious and spacious retreat over 2,100 square feet. Perfect for alfresco dining, the extended private lanai provides stunning ocean views beyond the swimming...
Amazing ocean views from this 11th floor villa!
This elegant Villa in the Ocean Tower overlooks the Pacific Ocean, sandy beach Lagoons, and the pools at KoOlina's premier residential resort community, The Beach Villas. Our resort sits aside the 2nd lagoon beach, next to the world class Disney Aulani Hotel and...
Beachfront Condo E 303/ Incredible views/Pickleball/Great Snorkelingn
Makena Surf E 303, located on the third floor of a gated low rise community, provides privacy, seclusion and spectacular sunset views. The condominium is located on the dry sunny leeward side of Maui. The private lanai provides views of Molokini, Kohololawe, and Lanai....
Private home w/resort style salt water pool and A/C
E Komo Mai! This 4 bedroom 3 bathroom North Shore/Princeville home is centrally located in the desirable Queens bath neighborhood. The backyard is a tiki style oasis boasts a private salt water pool, waterfall, Rockwall and tropical landscape that is sure to relax...
Nakoa Carriage House on Kauai's Sunny South Shore
Located in Poipu Beach Estates, this second level home features air conditioning, an open kitchen and living area and a King size bed. The private lanai provides sweeping views of the mesmerizing sunsets and cosmic evening sky.You will only be minutes from the Shops at...
Cozy suite with lovely ocean views, washer/dryer & furnished lanai - near dining
Sealodge F6Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Tucked away on the bluff above the incredibly blue Pacific Ocean, Sealodge F6 offers some of the best views on the North...