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 Hidden Retreat On North Shore Near Beach!
Discover Ha‘ena Place | North Shore Kaua‘iNestled on a quiet cul-de-sac, Ha‘ena Place is a true hidden gem—just a short stroll to some of Kaua‘i’s most iconic North Shore beaches, including Tunnels (Makua), Ke‘e, Lumaha‘i, and Hanalei Bay. Whether...
KA 211 OceanFront Island Style Condo w Ocean View Pool
Kaleialoha 211 OceanFront Island Style 1Bedroom Condo with Ocean Views for Beautiful Sunsets, Whale Watching and Year Round Indoor-Outdoor Living for Getaways, Relax and Recharge FREE daily activities included with your stay value up to $570! Complimentary admission,...
BRAND NEW AC | Ground Floor 1 Bdrm | Peekaboo Ocean View | Pool | 5 Min to Beach
Brand new 24,000 BTU AC installed in the living room March 2023.The perfect Hawaiian getaway at this ground floor 1-bedroom condo with private lanai, located at the beautiful Kiahuna Resort.The condo is centrally located in Poipu and is within a 5 min walk of the...
Aloha Suite Near the Sea I, 3 Block Walk to Beach! Great Location!
TA-166-694-5024-01 STR Permit # 2211-CCH-0303, TMK 1260230500039Enjoy the ocean with gorgeous sunsets day after day. Fun shopping, great restaurants & entertainment all around you!This studio is the perfect choice for your Hawaiian holiday! With comfortable...
Dreamy 2 Bedroom Condo on Kiahuna Beach in Poipu! With AC! Unit 140
This beautiful 2 bedroom/2 bath 2-story beachy, tropical treehouse-feel condo is located on the 35 acres of impeccably landscaped tropical gardens of Kiahuna Plantation; considered to be the only beachfront complex in beautiful Poipu, Kauai. Year after year Poipu Beach...
Garden Oasis Near Kukuiʻula Shopping Village w/Shared Pool and Free WiFi
Waikomo Stream Villas 202Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Like right out of the scene of a magazine, the garden oasis around Waikomo Stream Villas 202 welcomes you to...
Awesome Ocean Views in Top Floor Unit
Newly Remodeled Honua Kai Hokulani 710 - This is a top floor ocean view unit which is on the quiet south side of the Hokulani building. You will start your day with a beautiful sunrise over the Maui mountains and end your day watching the sunset all from the comfort of...
Your paradise - entire > 800 square feet apartment with affordable rate
DescriptionsFind your personal paradise at this lovely 1-bedroom, 2-bathroom vacation rental condo in beautiful Kihei. Nestled in the fantastic Kamaole Sands complex with access to pools, hot tubs, and the pristine beach shores, this unit offers accommodations for 2 and...
Completely Remodeled - Full Ocean View!
Our luxurious fully remodeled, non-smoking, front-row (G building) condominium is furnished and decorated to meet your highest expectations. It offers spectacular panoramic views of popular Kamaole III Beach and the ocean and neighboring islands beyond. Watch breaching...
Oceanfront Condo with Absolutely Breathtaking Ocean/Sunset Views - B238
Incredible Oceanfront corner location with an unsurpassed view of the ocean and sunsets. Enjoy 700' of tropical outdoor living on your L-shaped lanai. The sound of the waves will lull you to sleep since you are only 30' from the ocean. Comfortable tropical decor is...
Seaside Oasis-Near Beach w/ AC, BBQ & more!
*PER COUNTY REGULATION THIS PROPERTY ONLY ACCEPTS 1 BOOKING PER 30 DAYSThe Seaside Oasis has it all! Relax and soak in the views of the ocean that is just across the street. The Seaside Oasis is a gem on Northeast Oahu that sits just feet away from the warm, blue,...
Amazing 180° West Maui Ocean View Estate Pool w/Hot Tub- Central AC
Perched on four lush acres in Launiupoko, this gated estate blends the comfort of a secluded retreat with the feel of a boutique resort. Outside, ocean views stretch toward Moloka’i and Lana’i on the horizon. The main house sleeps 7 across three ensuite bedrooms...
3BR Ocean View Condo w/ FREE Parking, WiFi, Walking Distance to Waikiki Beach
3 Bedroom unit located on the 20th floor of a very popular condo. The unit is located in the heart of Waikiki, walking distance to Waikiki Beach, shopping, Honolulu Zoo and Waikiki Aquarium and fine dining restaurants. (World famous Hy's Steak house is located in the...
Gorgeous Ocean View, Comfortable Cool Elevation, Close to Everything!
This is a new home with stunning views. Beautifully nestled in Mt. Hualalai which is your backyard and a gorgeous ocean view in the front. You will never want to leave the luxury and comfort of this home. The cooler temperatures at this elevation make it a comfortable...
~ The Kauai Luna ~ Ocean - Waterfall & Sunset View
A Terrific Condo on Kauai...! AMAZING & SPECTACULAR VIEWS Ideal for Special Occasions, Traveling Couples & Families. It offers Multiple Unobstructed Views that other locations just can't offer including: The Jungle Valley with Tropical Birds singing at dawn and at dusk,...
Marriott's Ko Olina Beach Club Studio ( Read Description)
“This is a timeshare. While the amenities and features will be the same, you may not get the exact unit shown in the photos.”Units are assigned at check-in. Some units categorized as "Ocean view" may have obstructed view to the ocean.Welcome to our Marriott Ko Olina...
FULLY REMODELED-GROUND FLOOR CONVENIENCE-OCEAN VIEW-AC-METICULOUS CLEANING
Book with confidence, this stunning, 1 bedroom, 2 bathroom (820 sq. ft) condo at Kamaole Sands has been fully remodeled. 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...
Elegant Ocean View Condo- Just Remodeled with Central Air and King Size Bed
TAX ID TA/GE 119-559-9872-01HIGH END REMODEL COMPLETED 2017FREE WIRELESS INTERNETKING SIZE BEDCENTRAL AIR CONDITIONINGEnjoy swimming, snorkeling, or whale watching on one of Maui's finest beaches.Our privately-owned, SIXTH FLOOR condominium (VRBO 21787) has magnificent...
❤️PiH❤️ SUMMER BREEZE ★ NearPools/Rec Center ★ BeachToys/Bikes ★
Brought to you by Paradise in Hawaii Luxury Homes.Welcome to Summer Breeze at Kulalani on the Big Island of HawaiiThis home provides a perfect setting for your Hawaii getaway and is well suited for couples or families up to 7 people.We love friends & families• Big...
Mountain-view retreat with 2 suites, pool & hot tub - near restaurants & beaches
Villas of Kamali'i Apt 20Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'At the Villas of Kamali’i 20, you get it all - a convenient, split-level floor plan, gorgeous finishes, and...
Wailea Beach Villas PH112 - 3 Bedroom Garden View Penthouse
Awaken to the sweet sounds of palm trees swaying in the tropical breeze from Wailea Beach Villas PH112. Spanning 2,500 square feet, this main level, corner villa fuses a Hawaiian vibe with warm, earthy interior tones. The wraparound lanai offers peekaboo views of the...
Ohana Hale at Kahua Ranch - Private Ranch Paradise in Kohala -
Aloha! The Ohana Hale at Kahua Ranch is located in the Kohala Mountains on the stunning, privately owned, 4000 acre Kahua Ranch. We are a working ranch with sheep, cattle and horses and one adorable pig. Breathe in some of the world's freshest, crisp, clean air that...
🏖️Ocean View | 2BD with Loft | Fully Air-Conditioned | Complete Remodel
Country Club Villas 303, This TOP FLOOR UNIT comfortably sleeps 6 with each bedroom having its own full bath. 2-bedroom PLUS additional Queen bed in Loft. Three full bathrooms, Fully Air-Conditioned with Spectacular Sunset, Ocean and Golf Course ViewsCountry Club Villas...
Two Incredible 5 star reviewed Kolea villas
This listing is for two villas located in the best condo community in Waikoloa - Kolea! Our villas have over 150 5 star ratings and we have been doing this for over 10 years. We decided to create a new listing to allow guests to search for accommodations that will...
Large Home w/ 2 covered Pickleball Courts near Volcano National Park sleeps 16
Hawaii Pickleball Addicts Lodge is a beautiful, large private home with 2 covered Pickleball Courts (35' x 60' x 22' each) on 2 acres in Mountain View, HI, close to Volcano National Park, Kea'au, Kalapana Black Sand Beach, Uncle Robert's Awa Bar and Farmer's Market, and...
Beautiful 2 Br/2Ba, Oceanfront Unit.
Stunning views of breaking surf fill the living room of this contemporary condominium. Situated on a bluff overlooking Hideaways beach, the two bedroom, two bath end unit boasts endless ocean views and an open floor plan. Incredible surfing, snorkeling and beach-combing...
Spectacular Views and Natural Beauty
On the slopes of Mauna Kea, at 1200’ above the little town of Honomu is located the great waterfall of Akaka. Nearby, on top a hill is our private little piece of paradise. The house overlooks a vast swath of East Hawaii. From the blue of Hilo Bay to the mountain top...
Hale Hui Kai 106 - Beautiful Ground Floor Unit, on Keawakapu Beach, Split AC!
This unit, Hale Hui Kai 106, is one of Maui's hidden gems. Hale Hui Kai sits directly on the sand on one of the best beaches in the Hawaiian Islands, Keawakapu (Kay-Ah-Vah-Kah-Poo) Beach. Immerse yourself in the ultimate Maui beach vacation, with an ocean view from its...
Includes Mauna Lani Beach Club Pass. Fairways at Mauna Lani 704
This vacation rental is professionally managed by ResorticaHawaiiFairways at Mauna Lani 704. Includes Mauna Lani Beach Club PassPlease scroll down for detailed informationBedding Configuration:Master Bedroom: King BedGuest Bedroom: Queen BedAdditional Bedding: Single...
Maui Resort Rentals: Honua Kai Hokulani 232 - 1BR Suite w/ West Maui Mountain Views
Hokulani 232 is a luxurious 2nd-floor one-bedroom suite that offers views of The West Maui Mountains with its frequent afternoon rainbows. The suite is ideally suited for small families and couples who are looking for luxurious and spacious accommodations at a good...
Lovely Oceanfront 4th Floor Condo with A/C
This lovely 4th (top) floor, two bedroom, two bath, bright, clean and oceanfront condo has everything that you'll need for a great vacation, including A/C! (Mini-Split System - not a separate blower in guest bedroom). It's located at the very oceanfront Kona Bali Kai...
Lae Nani Beautiful Oceanfront Condo with newly installed AC 2BR/2BA
This two bedroom, two bath condo is located in the stunning oceanfront Lae Nani Resort on Kauai's East Shore. It is a second floor end unit featuring a large covered lanai, perfect for outdoor dining, with unobstructed views of the ocean and Wailua Bay.Lae Nani is a...
#239 Steps to Kamaole III Beach, New Kitchen 'Solid Gold Value' Maui Revealed
You will be right at the beach, there is super boogie boarding, great sunsets, & lots of beach walking! Hale Kamaole is a beautifully landscaped, low density property consisting of spacious one and two bedroom condominiums, it is rated 'Solid Gold' by Maui Revealed. Our...
Kona's Shangri La: Oceanfront Home with Pool & Spa
Kona’s Shangri La by Gather is the epitome of modern luxury. This stunning, custom-designed tri-level home sits right on the edge of the ocean’s rocky shoreline in Kailua-Kona. Perfect for large families or friend groups, this Big Island luxury vacation rental is...
Hale Mahie: 4 BR Spanish Colonial Historic Home with Ocean Views & AC
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.A 10-minute walk from Waikiki, discover your...
Luxurious Oceanfront Condo at Wailea Elua Village - Unit 1201, Central AC, Wi-Fi
Wailea Elua 1201 is perfectly positioned in the coveted interior courtyard, 39 steps to famous Ulua Beach, perennially named as one of the world's top 10 beaches and one of the best snorkeling reefs on Maui. This ground floor condo features an oversized, shaded...
Oceanfront 3 Bedroom Residence
This three-bedroom and three-bath standalone townhome is one of the Kona’s most desirable properties with stunning ocean views, an outdoor dining space, and access to a beautiful oceanfront pool. One of just 12 units in the community, this home offers a private...
Kona Ocean View, Pool and BBQ, Beautiful Gardens
Our condo has been renovated and has granite counter tops, upscale furnishings, remodeled bathrooms and everything a home needs. There is a king size bed in the master suite and two twins in the guest bedroom.The condo sleeps 4 with comfort and loads of space to spread...
Stunning Ocean Views - Upgraded 1BR - Kaanapali Shores 545
This condo is zoned as hotel and is compliant with current Maui County Short Term Rental ordinances.Oceanfront Paradise: Modern Comfort, Stunning Lanai Views, and Steps to Kāʻanapali Beach Aloha e kāua! Step into paradise and make this your home away from home, where...
Villas By The Cove, Ocean View 2 Bedroom Villa Steps To The Beach
Villa 4 at Villas By The Cove is a 2 Bedroom, 2 Bathroom villa. Remodeled with a spacious living room and ocean view patio, Villa 4 offers privacy and comfort set back in a tropical lush garden filled with mango and palm trees. This single story, stand-alone villa is...
Fabulous Diamond Head and Ocean views from this two-bedroom penthouse suite!
Waikiki Sunset #PH3807 – 229 Paoakalani Ave. (7-Night Minimum)This beautiful 38th floor penthouse suite boasts dramatic unobstructed ocean and Diamond Head views! The spacious 1308 square feet of modern design is cooled by energy-efficient central air conditioning and...
Renovated Condo on Golf Course
ALOHA! This beautiful ocean inspired condo is perfect for a romantic retreat or a solo getaway! It's bright and clean, and stocked with all you should need for a great stay! Located in the Turtle Bay Area, it's very close to beaches (about a 5 minute walk), golf course,...
REMODELED 2 BED/2 BATH CONDO W/OCEAN & MOUNTAIN VIEWS
Haleakala Shores at 2619 South Kihei Road is located in the heart of South Kihei, just a step away from some of the best beaches Maui has to offer. Its convenient location is also a walking distance to many restaurants, cafes, tourist gift shops, and a health food...
Hilton Waikoloa PoolPass for stays thru June 2025. ML Beach Club Pass. Golf Vill
This vacation rental is professionally managed by ResorticaHawaiiGolf Villas at Mauna Lani O2. Includes Mauna Lani Beach Club PassPlease scroll down for detailed informationBedding Configuration:Master Bedroom: King BedGuest Bedroom: : Queen BedHilton Pool Pass: Valid...
Hawaiian-Style Garden View 2-Br Villa, Ground Floor AC Kitchen & Beach Club Pass
Aloha! Relax and Enjoy this newly renovated, ground floor, 2-bedroom 2-bath Villa. Enjoy the fully equipped kitchen complete with granite countertops, bar seating, and all the cooking amenities you will need for a truly memorable stay! Added conveniences include a...
Incredible Unobstructed Pacific Ocean and Diamond Head Views!
Diamond Head Vista #1903 – 2600 Pualani Way(30-Night Minimum. ALL MONTHLY RESERVATIONS ARE SUBJECT TO APPROVAL.)Located on a quiet street at the edge of the Waikiki and Kapiolani Park, this 19th-floor Diamond Head Vista beauty has unforgettable, unobstructed Ocean and...
FABULOUS BEACH HOUSE, OCEAN FRONT VIEW, BEST LOCATION, WALK TO BEACH, RELAXING!.
STEPS AWAY FROM KAHALU'U BEACH!! PIECE OF PARADISE!! PRIVATE BEACH HOME!! COVID 19/ .... OPEN SPACE! Best priced in this area of Single-family PRIVATE homes of KAHALU'U BEACH AND MAGIC SANDS BEACH. Significance of landscape. Ali'i Drive of Natural Beauty. This land had...
Beautiful Ocean Facing Condo on Kaanapali Beach!
Nestled amidst the breathtaking vistas of Maui, this expansive one-bedroom condo presents an unparalleled ocean panorama, boasting captivating views of Molokai and Lanai. Set against the backdrop of one of Maui's most picturesque beaches, our retreat offers an array of...
Private Guest Suite near Beaches, Hiking & Golfing
Enjoy the peaceful tranquility of the location in the resort development of Princeville, with 24-hour security offering a delightful and safe venue for your North Shore “get-a-way.”This charming suite attached to a private home features a comfortable king-sized bed...
Gorgeous Oceanfront Home with Pool and Hot Tub in Paia
Maui County Rental permit - STPH 2013/0008TA-048-493-9776-01 / GE-048-493-9776-01TMK-260040080000WALK TO EVERYTHING IN PAIA TOWN!The setting is just stunning! Enter the back gate, and the first view looking through the glass door, across the entry area, and beyond the...