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.
Completely Renovated! Kona Reef Oceanfront 2 Bedroom Penthouse A37
See dolphins, whales, turtles and surfers from our oceanfront lanai, in the most desirable 2 bedroom penthouse in Kona! Enjoy our brand new oceanfront pool area , hot tub and BBQ pavilion (completed Nov 2021)!Kona Reef Oceanfront Resort is the 1st choice in vacation...
Oceanfront - Beautifully updated - Ground Floor - Kuleana 605
Beautiful - Oceanfront - Ground Floor - Walk OutFabulous updated oceanfront condo location: Kuleana 605 is right on the ocean on Maui's pristine West Coast with gorgeous panoramic views of the Pacific Ocean and the lovely off-shore islands of Molokai and Lanai. This...
Luxurious & Tasteful Oceanfront Condo!
Indulge yourself in a direct oceanfront atmosphere replete with refinement and luxury. Enjoy porcelain ceramic tile floors, granite counter tops, custom-built lighted cabinets, a spiral staircase ascending to the Master Bedroom Loft Suite, brushed glass Shoji closet...
Aloha Villas # 2, Steps to Beach, Close to Golf & Restaurants
Your Ideal Maui Family Getaway Steps from Lipoa BeachImagine carefree days at the beach with your kids, building sandcastles and splashing in the waves. At Elua Villa, your Maui family getaway awaits! This luxurious 3-bedroom, 3-bath ground-floor condo is just steps...
A Must See! Beautifully renovated Direct Ocean Front condo. 1 Bedroom, 1 Bath.
Welcome to Paradise on the Big Island of Hawaii! Gorgeous Direct Ocean front condo located at Sea Village in the HIGHLY DESIRABLE ocean front building #3 (unit 3217). This unit is special because of its location within the complex. Due to its position, it is more...
Luxury Ocean Front Living -- 180 Degree Direct Ocean View -- Best in Kihei
Welcome to Unit #330 at Sugar Beach Resort, Your private oceanfront oasis! The unit is in the Front row, literally 50 feet from the Ocean. Come enjoy the 180 Degree Panoramic Pacific views with winter time whale sightings right from your Lanai. The sunsets are memorable...
Magnificent! Private Pool & Hot Tub - 180 degree Ocean View; U pick Orchard
“Wow.”That’s the first word guests say when they arrive — and it’s easy to see why. The beauty of this place will take your breath away.If you’re dreaming of an authentic Hawaiian escape, welcome home. Wake up to the scent of tropical flowers, the songs of...
Maui Resort Rentals: Honua Kai - 4 Total Bedrooms, Gorgeous West Maui Mountain & Partial Ocean Views!
This tandem package combines 2 neighboring two-bedroom suites to create one of the best 4 bedroom values on the island. Each suite offers a great corner location and gorgeous views of the West Maui Mountains. One of the suites even offers some modest partial ocean views...
Spacious 3br/1ba home, A/C & WiFi
Our home is situated on a quiet family orieneted culdesac just below the Pauwela Cannery in Haiku. It is newly renovated with everything you'll need while you're here on your Hawaiian vacation. Hale Roselani offers an updated kitchen with granite countertops & stainless...
🏖️Ocean Front Views | Central AC | 3 Complex Pools | vrKCV
vrKCV - Kanaloa at Keauhou 2301, Professionally Managed by Kona Coast VacationsExperience Oceanfront Bliss at Kona CoveWake up to the soothing sound of waves and breathtaking ocean views from this stunning 2-bedroom, 2-bathroom oceanfront condo, Kona Cove. Located in...
Maui Eldorado D206~Renovated & Spacious 1 Bed/2 Bath with Ocean Views
🌴 Aloha from Maui Eldorado D206 – Your Ocean-Kissed Home Away from Home! Imagine waking up to the soft glow of sunrise over the West Maui Mountains cascading into the Pacific, sipping fresh Maui coffee on your private oversized lanai with two plush chaise...
Maui Resort Rentals: Honua Kai Hokulani 937 – 2 BR Corner w/ Stunning 9th Floor Ocean Views!
Hokulani 937 is one of only (4) 2 bedrooms at Honua Kai with this highly sought after floor plan. Exclusive to the 9th floor of Honua Kai, this suite offers commanding direct ocean views, unsurpassed among two-bedroom ocean views at Honua Kai. Experience a true panorama...
Hula House: Luxury Kukui'ula Villa with Superb Amenities
A private luxury home with all the appeal of a beautiful 5-star resort, and an emphasis on recreational activities: that was the defining vision behind the creation of Hula House, and this extraordinary property in Kukui'ula’s scenic Kula Makai section delivers...
OCEANVIEW 3 Bedroom 2 Bath Condo - Kahana Village 13
Welcome to your Maui dream vacation at Kahana Village — a serene oceanview oasis located on the desirable West Side of the island. This 3-bedroom, 2-bathroom ground-floor condo is new to the rental market and features stunning views, fresh updates, and the comfort and...
Oceanfront resort, Kanaloa at Kona, Sleeps 6
Enjoy your tranquil Hawaiian experience in this spacious 2 Bedroom/2 Bath End Unit. Located off the 11th Fairway with stunning garden views from our 2 lanais, our home sleeps 6 with a sleeper sofa in the living room. Envision yourself sipping a tropical beverage at the...
Fresh and New Luxury Elua Village 2 Bdrm+2 Bath Paradise Condominium #907
New, New, New! New furniture, new electronics, new beds, mattresses and linens, paint and artwork. Sooooo close to the beach! Treat yourself to the best that Elua Village has to offer. You and your guests will enjoy the short walk to the beach from this special property...
Newly installed A/C! Unit 48 beautiful condo with 2 beaches within 2 minutes
Brand new A/C just installed. Remodeled and upgraded just for you! Unit 48 (building 9) is in a peaceful and secluded location of the sprawling 35 acre Kiahuna Plantation resort complex. The grounds boast wide, green manicured spaces coupled with beautiful flowering...
Aloha! Close enough to the beach you can walk. Maui misses you!
This unit is the Trifecta of locations! Close enough to walk to the beach(6 min), close enough to walk to grocery stores(12 min) and restaurants yet far enough away from the road noise on S. Kihei Rd not to hear it. This generously sized 2BR 2 BA condo with 745sf...
Blue Kauai at Islander on the Beach!
Aloha and Welcome to Blue Kauai at Islander on the Beach!Beautifully Renovated Ocean & Pool View Studio Condo - Air Conditioned! No Resort Fees!Blue Kauai - Ocean/Pool View & Prime Location! This Beautiful Ocean & Pool View Studio Condo is located on the second floor,...
Expansive 5-Star Resort Living with all of the Advantages Of Home.
AccommodationsStep into your Aloha home away from home and feel the rest of the world melt away. This beautiful home has it all - almost 2500 square feet of indoor living including a fully equipped gourmet kitchen with granite counter tops, stainless steel appliances,...
Ground-floor condo with ocean view, high-speed WiFi, & full kitchen
Mahina Surf 102Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Set up for comfort and ease, this condo on the ground floor is ready to welcome guests to the island. Underneath the...
16th Floor PH in Ocean Twr w/Panoramic Ocean View Ko Olina
*Brand New furniture just delivered to the unit! New couch, new chairs, new coffee table, new dinning table and chairs and twin mattresses (As of April, 2025)Enjoy privacy and luxury in this one of a kind penthouse. This penthouse has exclusive elevator access and only...
2nd floor, 2 bedroom deluxe vacation condo
Kaanapali Royal D202 is a lavish 2 bedroom, 2 bathroom sanctuary adorned with opulent furnishings and modern upgrades. Situated on the 2nd floor at this deluxe vacation condo, but please note that the resort does not offer elevator access. This haven comfortably...
Ocean Views, Updated Condo, Great Location MPS315
Beautiful remodel and ideal Kihei location create beachy perfection for your island getaway.Relax on your own huge lanai. Feel the wonderful trade winds and take in the island scents from the beautiful Plumeria trees and Hawaiian foliage. The lanai furnishings coupled...
NICELY REMODELED-2 BEDROOM WITH LOFT-OCEAN VIEWS-AC THROUGHOUT
Book With Confidence, This Nicely Updated 2 Bedroom Condo That Features A loft With An Additional Queen Sized Bed. 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...
Wraparound Lanai - Direct Oceanfront View, sleeps 6, new A/C, free WIFI
Our fully central air conditioned condo unit 711 is beautifully appointed with island decor throughout. The master suite boasts a tropical trip-tic by a local artist. In addition, the dining and living areas also include original art. From the moment you step in the...
Maui Resort Rentals: Honua Kai Konea 214 - Upgraded 1BR w/ Extra-Large Balcony and Gorgeous Mountain Views!
One of the finest 1br mountain view suites available to rent at Honua Kai, Konea 214 is a luxurious upgraded 1br mountain view suite featuring a spacious floor plan, an extra-large balcony, and numerous upgrades throughout. From suite 214 your group will be treated to...
TOP FLOOR, OCEAN VIEW 2/2 WITH COOL SPLIT A/C
You're on the top floor of desirable "A" building with OCEAN & mountain views..SO CLOSE TO THE OCEAN YOU CAN HEAR THE WAVES! Decorated island style with traditional Hawaiian tapas and Tropical furniture...you will truly feel you are in Hawaii. We want you to fall in...
The Beach House - Closest House to Magic Sands Beach, Pool, Pickleball Court
Location, location, location. The Beach House is the closest rental house to Magics Beach and Magics Grill. Magic Sands Beach is the the most popular beach in town and gets its name from the fact that the sand comes and goes based on the waves. (Really big waves will...
Beautiful top floor condo w/ amazing view of Papohaku Beach
Hale Kamaluhia, Hawaiian for House of Serenity is our tropical retreat on the West coast of Molokai. Our desirable second floor condo has vaulted ceilings and an unobstructed view of Papohaku Beach, one of the longest white sand beaches in Hawaii. Hale Kamaluhia is our...
NUC 90/BB-0069, GE-014-134-8864-01, TA-014-134-8864-01
Start your day with a stroll on one of the most beautiful beaches in the world. Enjoy the sunrise in Kailua where your Hawaiian holiday truly begins. Kailua Beach is a perfect place to go to 'get-away-from-it-all.' Swim, boogie board, surf, kayak, sail, or windsurf in...
Oceanfront Luxury | Best View at Kuleana | AC | Pool | Lanai 614
Welcome to Unit 614 at Kuleana Resort — a true oceanfront gem nestled between Kaanapali and Kapalua in West Maui. Just steps from the water, this fully remodeled 1-bedroom, 1-bath condo offers unobstructed, panoramic views of the Pacific, Lanai, and Molokai.Enjoy...
Kona Alii Penthouse with Village and Ocean Views
This beautiful condo is located in the heart of downtown Kailua-Kona. Two bedrooms with private baths, and king size beds and flat screen TV. The loft bedroom opens to the private sun deck with stunning panoramic views.The kitchen is fully equipped with everything you...
Gilligan's-secluded air-conditioned Cottage Near Gorgeous Beach--TVNC-4189
And not only secluded, but only a four and a half minute walk to a gorgeous and private beach! (I know VRBO wrote “six minute walk” in the title, but I measured it once!). Gilligan's Beach Cottage is not like one of the houses packed into town--it is about 15...
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
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
Rent All 4 Beachfront Villas for Your Family Reunion or EventDiscover 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...
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....