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.
Kamaole Sands BUILDING ONE Ocean View- 2BR/2BA- Large Lanai & A/C THRU-OUT
GE/TA# 146897766401Maui temperatures seem to keep going up so please note Kama'ole Sands 1-405 has a "three zone split air conditioning system". When the trade winds aren't blowing, you'll be glad 1-405 will be a cool place for you to recharge for the next day!So,...
Luxury 2 bedrooms on Molokai
2 Bedroom 1.5 Bath & very rare 2 lanais with oceanviews - Sleeps 6 Gorgeous rare condo at Wavecrest with the luxury of 2 bedrooms, 1.5 baths and 2 separate lanais that both have views of ocean and beautiful tropical courtyard.Also, private FREE High Speed wifi for...
Luxury Ko Olina O1002 Spacious 3BR : Ocean and Mountain Views
Luxurious Penthouse 3 Bedroom Sleeps 8(1king,1queen,2twin, (+2twin airbeds)) , 2.5 Bath (3toilets ,2 shower, 2 tubs ), 2 Parking Unit Ko Olina Beach Villas | Kapolei, Hawaii Newly Upgraded (Oct 2024): Washer, dryer, and dishwasherNew sofa (April 2025 )Villa...
Sleeping Giant Cottage with Plunge Pool TNVC #1244
We're thrilled to share our house in Kauai with you! There's a swimming pool, botanical garden-like setting, and location that's extremely convenient for exploring the island. Our plunge pool is perfect for cooling off after a day at the beach or just lounging in all...
NEW! Top Floor Views with A/C in Poipu Beach, Resort Amenities
Top Floor Unit | A/C | 3 Minute Walk to BeachKiahuna 42 is a top floor unit (2nd floor) that is centrally located in the heart of the Kiahuna Plantation in Building 8. It has built in A/C and new furnishings and is only steps away from Poipu Beach!Enjoy free access to...
Pali Ke Kua 101 .. Stunning Ocean & Bali Hai Views
Near the edge of a bluff overlooking the ocean, this ground-floor condominium offers fabulous ocean and coastline views. Bali Hai, the landmark mountain made famous in "South Pacific," is just one of the awesome sights that guests enjoy here. Relax indoors or on your...
Oceanfront Sugar Beach Resort Penthouse 34. Amazing Ocean Views! Remodeled!
Welcome to Sugar Beach Resort Penthouse 34, one of the best ocean view condos in Maui. The top floor lanai is very private and looks out on endless ocean and 5 miles of white sandy beach - perfect for peaceful morning or evening walks. Watch the whales during whale...
BEACHFRONT HOUSE KIHEI, MAUI..TRUE HAWAIIAN HOME 1960's
This is a Private, BEACHFRONT Residence. PROPERTY IS FRONTED BY A HAND BUILT LAVA ROCK WALL. We offer you and your family a True Hawaiian Home, built in 1960. All of the charm still remains, although we have updated the interior, but preserved the integrity and special...
Top floor stunner! Gorgeous Views! Book Now for Summer!
West Maui Welcomes You Back. Our communities of Kaanapali, Honokowai, Kahana, Napili, and Kapalua; we all welcome you. Please have compassion and malama (care for) the island during your visit!For only the most discerning guest. This top floor stunner offers magnificent...
❤️PiH❤️Aloha Paradise ★ Large Private Heated Pool & Spa ★ PLUS Hilton Resort Pass
BROUGHT TO YOU BY PARADISE IN HAWAII LUXURY HOMESWelcome to Aloha Paradise, nestled in the stunning Ainamalu community of Waikoloa Beach resort – your perfect retreat on the big island.Aloha Paradise is an elegant single level home thoughtfully designed for comfort...
Maui Resort Rentals: The Whaler 720 - Luxurious 7th Floor 1BR w/ Gorgeous Ocean and West Maui Mountain Views!
Enjoy beautiful views of the Pacific Ocean and Maui's neighboring island Molokai, as well as views of the West Maui Mountains from this luxurious 1 bedroom suite at the iconic Whaler in the heart of Kaanapali Beach.Tastefully remodeled and featuring numerous upgrades,...
Hale Ma'ana Hou - Poipu Beachfront Home with A/C and Pool!
The Garden Island offers you this beautifully appointed, Mediterranean style home that is located on a protected white sand beach in sunny Poipu. The large, stylish, and open living room offers magnificent, ever-changing views of the Pacific Ocean with spectacular...
Newly Renovated Kahana Sunset ocean view
Summary:Kahana Sunsets is your place for an ocean front resort. This is a ground level condo with ocean views from the patio, bedroom and living room. This condo is fully renovated and all new items with many upgrades. Enjoy the secluded beach, BBQ's (either poolside or...
Aloha Villas Resort | 12 Bed, 12.5 Bath
Aloha Villas Resort: Your Maui Oceanfront OasisDiscover ParadiseNestled on the picturesque South Maui coastline, Aloha Villas Resort offers a luxurious beachfront retreat for your next family gathering. This stunning 4-villa complex provides an unparalleled oceanfront...
Extra spacious, private, 1BR/2BA, front row, ocean view at Maui Kamaole (A101)
Set on a grassy hilltop with expansive ocean views in beautiful South Kihei is Anthurium House at Maui Kamaole. Surrounded by lush tropical landscaping, this extra spacious (1,061 SF) 1BR/2BA ground floor condominium unit enjoys an unbeatable front row, end-unit...
North shore beachfront villa on Ke-iki beach
ALOHA!Welcome to our beachfront villa!This three bedroom home is located in a gated community fronting Ke-Iki beach, famous for its sand, surf and sunsets. It's also a great place to catch a glimpse of Humpback whales and spinner dolphins passing in the far-off waters....
Oceanview condo with 3 bedrooms, 3 1/2 baths and AC throughout
Enjoy captivating ocean views from this spacious 3 bedroom, 3-1/2 bath condo, where you can relax with spectacular sunsets on the lanai. There is air-conditioning throughout the condo, and you can control the temperature in each room individually. Our condo is on the...
SPECIAL DEALS! Hotel Room Studio - Direct Bali Hai & Hanalei Bay Ocean Views
Lovely and romantic, this popular honeymoon destination condo overlooks Bali Hai and Hanalei Bay. The room boasts a comfortable, king size bed with designer bedding, large remodeled bathroom, a small sofa sleeper, and large slate covered private lanai for sunset...
Private luxury home with high ceilings and room for 6
Welcome to the Fairways, the upscale Townhouse community located in the exclusive Mauna Lani resort community on the Big Island of Hawaii. This private gated community offers beautifully appointed luxury homes with golf course views, vaulted ceilings and open floorplans...
Ocean view from every room in the condo!
Enjoy our condo in lovely Poipu with vast ocean views from the lanai and Master Bedroom. You will hear the ocean, see the ocean (and the whales in season) and be mesmerized by the ocean and the sea life. Sunset Kahili is the highest condo in the area. Our resort is on...
COMPLETELY REMODELED-AC THROUGHOUT-GROUND FLOOR-METICULOUS CLEANING
Book with confidence, this stunning, 2 bedroom, 2 bathroom (1200 sq. ft) condo that has been completely 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...
The Best of the Best
Our condominium located at Kamaole Sands in sunny south Kihei has one of the superior garden/ocean views and is just steps from the Kamaole Beach III which is rated the top family beach in Hawaii by Sunset Magazine. This location is very protected from weather and...
3 bedroom with central A/C at Fariways at Mauna Lani #1705!
You, along with your family and friends, will make wonderful memories at this spacious, well-appointed townhome located in the quiet gated community of The Fairways at Mauna Lani. North of the Kona International Airport, on the sunny Kohala Coast, this townhome is...
Top Floor corner unit in main building !
Treat yourself to the ultimate in tropical island luxury with a stay at this beachside condominium. This luxury condominium offers access to two close elevators and is an end unit.Situated inside the brand new Waipouli Beach Resort and Spa, this condominium is fully...
Ocean View South Maui Condo with Lanai plus FREE parking, Wifi and Smart TVs
Condo with Ocean views from lanai, living room and kitchen. One bedroom (KING bed) , one bathroom (walk in shower), Lanai with seating to enjoy the gorgeous ocean views in South Kihei, Maui. Walk across the street to Kamaole II beach. Proximity to restaurants, shops,...
*Makani A Kai B9* Maui Condo Steps To The Sand!
This 2nd story beach front condo offers direct beach access from complex grounds with views of the breathtaking Maalaea Bay, the grand volcano Haleakala and the sparkling Kihei lights at night. Enjoy your private lanai. The loft style primary bedroom features a king...
Newly Renovated Closest to Ho'olei Pool, Wailea Beach, the Grand, Fitness Center
One of a kind four bedroom Ho'olei home in Wailea!Breathtaking is the best word to describe this luxury townhouse-style villa at Ho’olei, situated in beautiful Wailea on the sunny, southwestern shore of Maui. Ho’olei is the ultimate dream home in paradise!This...
Minutes from Downtown Hilo, Sleeps 6
Welcome to Hilo Hale Kaumana! Minutes from Downtown Hilo, this home has everything you need for that getaway to the Big Island. Sleeps 6This fully renovated and beautifully decorated 3 bedroom, 2 bath home is the relaxing retreat you’ve been seeking. The quiet...
Ma'alaea Surf, Unit G10, 2BR Beachfront Condo, AC, Wifi, Pool, TV, Kitchen
Ma'alaea Surf, Unit G10 is a two story townhouse unit with vaulted ceilings. This unit has a large lanai, stunning ocean views and overlooks the large pool and shuffleboard court. This elegant unit features a gorgeous fully furnished kitchen and is equipped with central...
Maui Resort Rentals: Honua Kai Hokulani 606 - Large 6th Floor 2BR, Corner Floor Plan w/ Direct Ocean & Mountain Views
Located in one of the closest 2 bedroom columns to the ocean at the entire resort, Hokulani 606 boasts direct 6th-floor ocean views AND lush West Maui Mountain views from its prime corner location.Suite 606 affords a perfect opportunity to gather, reconnect, and...
Luxury Upgraded Condo #98, AC, Poipu Beach, Partial Ocean View
Air Conditioned? Yes!!!Only few condos at Kiahuna are Air Conditioned. We are excited to announce that as of Sep. 2, 2021, our condo is fully air conditioned.Kiahuna Resort is 35 acres of landscaped, manicured lawns and gardens. This oceanfront resort is just steps away...
Mika Kai 4 bd w/Pool and Hot Tub - Epic Spot for Whale Watching!!!
Fully Licensed Short Term RentalSTVR-19-344467/NUC-19-255GE-131-303-1680-01TA-131-303-1680-01Each guest will be asked to sign a rental agreement after booking is accepted. Fabulous furnishings and upgrades to this already beautiful house.Here is the base of operation...
11th Floor Oceanview Sunny Studio 1115! 5 Star Reviews!
Aloha from the gorgeous sunny studio Whaler #1115 at The Whaler on Ka'anapali Beach. Whaler 1115 is located on the 11th floor on the sunny courtyard side of Tower I, the north tower. This fully remodeled interior features an open kitchen with an oversized granite...
Waikomo 302 by Destination Kauai - A/C, Ground Level Updated Condo
E komo mai, welcome to Waikomo Stream Villas 302!This 1-bd/1-ba condo is on the ground floor with landscaped views in the heart of sunny Poipu. The fully equipped kitchen has been renovated with new cabinets, countertops, and stainless steel appliances. The bathroom is...
Kihei Garden Estates B-103 - Modern Design, Bright & Clean, Concrete Floors, AC!
The new roof project will take place over the pool area from 7/18/25 to 7/27/25. During this time there will be noise and debris surrounding the building.------------------------------------From the front door, a magical stretch of Maui beach awaits your exploration -...
Hale Kamaole 121: Ground Floor Gem with Sunset Views & Resort Amenities!
Welcome to the highly sought after Hale Kamaole 121! This perfectly located ground floor unit offers beautiful sunsets and ocean views right from your lanai.As you enter you are greeted by the open comfortable feel of this beautifully updated condo. The kitchen has been...
Maui Resort Rentals: Honua Kai – 7 Bedroom Groundfloor Resort Residence, Over 4500 Combined Sq. Ft., Massive Lawn Area, Steps to Pools/Beach/B.B.Q.s
This package combines 3 adjacent ground floor residences at the luxurious Honua Kai Resort to create a 7 bedroom masterpiece that is simply in a league of its own. Large families and groups are treated to the space of a luxury home with all the advantages of resort...
🏖️Private Ground Floor Corner Unit | AC & Ocean Views | vrKCV
vrKCV - Kona Isle D1, Professionally Managed by Kona Coast Vacations.Oceanfront Serenity at Kona Isle D1 – A Couple's RetreatEscape to Kona Isle D1, a modern one-bedroom, one-bathroom ocean-view condo, perfect for a couple's getaway on the Big Island of Hawai'i....
Escape to paradise at Mauna Lani B208, an exceptional oceanfront retreat
Mauna Lani B208 Oceanfront Vacation Rental – 2 Bed, 2.5 BathEscape to paradise at Mauna Lani B208, an exceptional oceanfront retreat offering unparalleled luxury and breathtaking views. This stunning 2-bedroom, 2.5-bath condo is situated in one of Hawaii's most...
Gorgeous 3bd/2ba villa with huge covered patio, BBQ, koi pond & playground
Alas Del Kealoha is a luxurious large private gated (not fenced) house located in the heart of Volcano Village. This beautiful getaway home is a well illuminated 3 bedroom / 2 bath one-story pine house. Sleep up 10 to guests! 8 guests sleep on beds, 2 more guests sleep...
Villages 640 - Expansive Maile Floorpan with BBQ & Ocean Views!
Mauna Lani Villages 640 is a spacious & modern three bedroom two-story town home that can accommodate eight guests comfortably and includes plenty of lanai space with garden and distant partial ocean views located right in the middle of the exclusive Mauna Lani Resort....
Exquisite Oceanview - Kihei Surfside #310 - Your Gateway to Maui Bliss!
Kihei Surfside #310 – Breathtaking Ocean Views with Island Comfort and Split-Duct ACStep into the serene beauty of Maui with a stay at Kihei Surfside #310. This 1-bedroom, 1.5-bathroom condo offers stunning oceanfront views from the third floor and a comfortable...
OCEAN/BEACH FRONT GROUND FLOOR SPECTACULAR VIEWSn
Spectacular views, peace, tranquility and beautiful sunsets are found at Hoyochi Nikko 102. After a busy day of sight seeing, golfing, visiting beaches or whatever you choose to do during the day, this is the paradise you will come home to. This ground floor condo is...
Maui Resort Rentals: Honua Kai Hokulani 616 - 6th Floor 1BR w/ Partial Ocean & Mountain Views
Hokulani 616 is a wonderful 6th-floor suite offering views of both the blue Pacific Ocean and the verdant West Maui Mountains. A southern orientation offers abundant light as well as natural protection from the strong Maui trade winds.Suite 616 boasts an exquisite...
Top Floor Oceanfront Studio #311 W/LANAI and A/C
COOL A/C IS AVAILABLE when ocean breezes aren't enough.Unit # 311 - We have one of the few units in the building with an ACTUAL outdoor patio to enjoy the beautiful ocean view, which is direct ocean front, with famous Magic Sands Beach right next door! And with our COOL...
20% Fall Discount! Newly Renovated! Oceanfront & Pool Family Hideaway. Paradise.
Kalani Kai Beach House is a newly renovated, private gated oceanfront home located on one of the Waialae Beach Lots with a beautiful swimming pool nestled next to a sandy beach.The upstairs master suite has a king-size bed and panoramic ocean views from a spacious...
Pristine White Sand Beaches, in Waikoloa Resort
Kolea #16E is in the only beachfront complex in the Waikoloa Resort. NO RESORT FEES. Unlike other resorts, Kolea #16 does not charge any resort fees. This property is located on the famous Anaeho'omalu Bay, a 4 minute walk away through the Beach Club.***DISCLOSURE: We...
Beachfront Beach Villas at Ko Olina O-501
Summary:Beach Villas at Ko Olina is about a couple miles stretch of coastline in this resort area. Four lagoon beaches that is shared with Disney Aulani, Four Seasons and the Marriott Vacation Club. But, the Beach Villas sits on "Honu" Lagoon which is basically...
Relaxing Hawaii Beach House
Located in a peaceful private community next to the sea, this newly-built home is perfect for those seeking a serene retreat. This home sits within walking distance of Kokololio Beach Park as well as a shopping center for essentials and popular local eateries. Venture...
Oceanfront, Palm Trees and the Beautiful Blue Pacific Ocean...Poipu Palms 202!
Palm trees and the beautiful blue waters of the Pacific Ocean greet you the second you open the front door of Poipu Palms 202.This is the beginning of your perfect Hawaiian vacation.Overlooking the powerful Pacific Ocean and the spectacular Poipu coastline, this nani...