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.
Breathtaking Oceanfront Home on Lava Rock Beach.
Summary:Embrace the beauty of Hawaii with a stay at our breathtaking oceanfront home, where you're surrounded by the soothing sounds of the waves and the gentle Tradewinds. From our expansive, floor-to-ceiling windows to multiple lanais, you'll enjoy panoramic views of...
Stunning BEACHFRONT Ground Floor Condo – Fully Renovated & Ready to Welcome You
Experience the ultimate in Tropical Beach Living at this beautifully renovated, ground-floor 1-bedroom, 1-bath condo at Kihei Sands. Complex located right on the beach, this chic retreat combines modern style with the laid-back charm of Maui. With a design that blends...
Dolphin House by Gather: North Shore Escape w/ Direct Beach Access
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.Welcome to Dolphin House by Gather, a charming...
Maui Sunset #A216 - Oceanview King Bed, 1BR, 2 BA Condo
Maui Sunset is a beautiful oceanfront resort and is the perfect vacation home on Maui. Swim in the large swimming pool or just enjoy sitting on a chaise lounge by the pool or in the jet spa. It is especially beautiful in the evening relaxing under the stars and enjoying...
Kauai North Shore Oceanfront - Mountain View Beachouse TVNC#1136 Tsunami Zone
Hawaiian Island Beachfront cottage with an incredible location on the North Shore of Kauai in between Hanalei and Haena close to Tunnels. The 3/4 acre property features a large sandy beach point. Some of the islands best snorkeling and shelling right out front of the...
Modern Renovated Kaanapali Studio! We have the Best Reviews for a Reason!!
After a full day of enjoying all that Maui has to offer, come home to your air conditioned oasis in the heart of the Kaanapali resort. Maui Eldorado J115 has been totally rebuilt to reflect the island lifestyle that you deserve.A ground floor unit in one of the best...
Maui Resort Rentals: Luana Garden Villas 2A – Modern 3BR Villa at Kaanapali’s Newest Luxury Residences!
This luxurious 3bedroom/3bath residence is conveniently set within Enclave One of the Luana Garden Villas. Villa 2A's north facing orientation offers a Shady respite from West Maui's legendary endless sun and its designation within "Grounded" collection at the Luana...
Oceanfront Penthouse Sleeps 8! New Central Air! Gorgeous 180° Views- w/Loft!
Penthouse views, three breezy bedrooms, and front-row whale watching. This top-floor oceanfront condo offers Moloka‘i sunsets, honu in the surf, and open-air dinners on the lanai. With central A/C, three baths, and Papakea’s pools below—you may never want to...
A 5-Star Estate, Large Groups, Luxury Living
This luxury condo is situated a short walk from the beauty of the beach! A 3,700 square foot, 3 bedroom, 3.5 bath gem, it is the ideal place for a quiet retreat. Features a Master Suite with private lanai and two additional bedrooms with en suite baths, sleeping up to a...
New Listing! Nature-themed oasis in Kihei
Welcome to Maui Kamaole F101 – your perfect island retreat! This beautifully appointed ground-floor condo features 1 bedroom and 2 full bathrooms, comfortably accommodating up to 4 guests. The dual-bathroom layout is ideal for families or couples traveling together....
Hawaii Life Rentals Presents Villas of Kamalii 17
This bright, spacious three-bedroom, three-bathroom townhome is located at Villas of Kamalii, in the prestigious resort community of Princevile. Perched on the highest part of world-famous Makai Golf Course, enjoy stunning mountain and waterfall views from your private...
Penthouse Condo with Ocean Views
**Special reduced rates for last minute bookings in August** Our slice of Hawaiian Paradise!Third floor corner unit at Vista Waikoloa. Private lanai with beautiful views of Mauna Kea, Moana Loa and Hualalai mountains plus A Bay beach palm trees and ocean. In the winter...
Beachfront Family Estate. Great for multiple families.
Nestled in central Kihei on the northern end of picturesque Halama Street, this family-owned, legal short-term rental features two accommodation options on a beachfront property: a two-story building with four individual units and a detached 2-bedroom cottage. Guests...
2 Bedroom Penthouse and Amazing Ocean Views!
Enjoy a top floor penthouse villa, directly overlooking the ocean and newly renovated pool at the Mauna Lani Terrace! Building "H" is one of the most requested and boasts a location directly on the seafront, nestled between the luxurious Auberge Hotel and the private...
VACATION DATES: OCTOBER 18-25, 2025: 2BR/2BATH VILLA KAANAPALI
ENJOY AN OHANA HAWAII EXPERIENCE AT A VALUE PRICE. EXPERIENCE PERSONAL CUSTOMER SERVICE FROM AN OWNER OF THIS VILLA TIMESHARE.OFFERING OUR 2 BEDROOM / 2 BATHROOM UPPER FLOOR OCEANFRONT VILLA AT $850 DAILY RENTAL PRICE. GUARANTEED UPPER OCEANFRONT VILLA ON FLOORS 9-...
Downtown condo with pool, tennis, & mountain view - walk to beach
Waikiki Sunset 1605Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome to your newly renovated 1-bedroom, 1-bath condo at the Waikiki Sunset in Honolulu, HI. This apartment...
(4102/03) 2Br Ground Floor Hanalei Bay Resort, Ocean View, Pool, Tennis
Welcome to Hanalei Bay Resort unit 4102/4103. A ground floor unit with stunning views of Hanalei Bay and the surrounding Bali Hai Mountains. This beautiful unit has 2 bedrooms, one with a King size bed and large en-suite bathroom with a shower to rinse off after a day...
Banzai Surf Escape -w/ AC, Epic beach by the house!
Banzai Surf Escape has all of your basic needs so that you can best spend your time relaxing near the ocean and enjoying all of the local spots. The open floor plan allows you to breath and relax during your stay. Enjoy air conditioning after a hot day at the beach and...
Pili Mai Family Fun Condo, AC, Game Room, 2 Bedroom, 2.5 Bath, Sleeps 6
FAMILY FUN at Pili Mai, 2br + Game room (bumper pool, poker table, classic video game console, board games, piano, masks and snorkels, beach chairs, croquet, and small yard for the kids to play) 2.5 bath, sleeps 6, no stairs, back yard lawn. Condo is located near the...
Spacious Lanai Retreat: Kapalua Maui's Golf Villa with Breathtaking Views 14T 1-2
This is a legally permitted vacation rental according to the County of Maui ordinances.Spacious Lanai Retreat: Kapalua Maui's Golf Villa with Breathtaking ViewsImmerse yourself in the epitome of luxury with our recently refurbished 1-bedroom, 2-bathroom condo, nestled...
Epic Forest View, A/C, Fruit Trees, Beach 5m drive
Experience this forest retreat complete with a cozy queen bed, AIR CONDITIONING, vaulted ceilings, convenient kitchenette, half bath, and an outdoor hot/cold shower. Relax on the expansive deck facing breathtaking panoramic views of the untouched jungle. Immerse...
Wavecrest Oceanfront Rental
TA-061-740-4416-01GE-061-740-4416-01This recently remodeled ground floor oceanfront condo with spectacular ocean views on the lush and undeveloped east end of the " friendly" island of Molokai , is one of the most picturesque locations. Enjoy the amenities of the...
Artevilla at Pauoa Beach - Luxury Estate with Private Pool & Club Perks
Welcome to Artevilla at Pauoa Beach, the best of modern living in a classic Hawaiian setting.Nestled adjacent to the renowned Fairmont Orchid 5-star Hotel and Mauna Lani, Auberge Resorts Collection, Artevilla is a lavish two-story villa offering unrivaled luxury....
Luxury Oceanfront Air-Conditioned 2 bedroom Condo Rental- 35 Feet from the Water
Open the door to our beautiful second home in Kauai and know you are in paradise. There is nothing between you and the vast blue ocean, just 35 feet away, which is framed by a wall to wall expanse of floor to ceiling windows. The soothing sounds of the ocean fill the...
REMODELED 2 BED/2 BATH CONDO ACROSS FROM KAM3 BEACH W/ OCEAN VIEW
Maui Parkshore at 2653 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 store!...
Luxury Kolea Golf & Hilton Pass, Partial Ocean View, 2 Min to Beach & Clubhouse
Villa Makai at Kolea, an ocean and beach front resort located on Anaeho’omalu Bay (A Bay), is the perfect spot for a refreshing get-away or the ultimate location for your home-away-from-home! Just a few minutes' walk from A-Bay, the only white sandy beach at Waikoloa...
Great View, 3 Pools, A/C, Walking Distance to Beaches! Kapalua Bay Villa #38G3
* NEW PROMO: Stay 5 or more nights from August 1st - October 25, get 1 FREE! Welcome to Kapalua Bay Villa 38G3, a beautifully renovated 1-bedroom, 1.5-bathroom ocean-view villa that offers the perfect blend of refined luxury and island serenity. Located in the...
Across From Kamaole 2 Beach, This Concrete Resort Is Maintained Well
Very important, Kihei Kai Nani is HOTEL ZONED, and not affected by ongoing Maui Transient accommodation issues, ours is a one-bedroom condo, on the top corner (2nd floor) of building #3, which is the second floor of a concrete building. The unit has a full kitchen and...
Large, beautiful, updated home w/pool, AC,mins from beach in Kailua! Flex stays!
Welcome to Holoholo Hale in the beautiful town of Kailua on the island of Oahu. Kailua is the home of two of the best beaches in the world, Kailua Beach Park and Lanikai Beach. The home is a short drive to all the island has to offer including Diamond Head, the pill box...
Welcome to Luana Garden Villas 3B & 3D
Crafted for multi-family vacations or larger gatherings, this listing offers two distinct Villas at the illustrious Luana Garden Villas — nestled on the captivating Kaanapali Beach on Maui’s western coast. Together, the upper and garden level villas are a haven of...
Villa Hui Hou: Luxe O'ahu Villa Private Oasis! Gourmet Kitchen & Media Room
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.Discover the allure of Kailua at Villa Hui Hou...
KHV 17 Spacious 2BD West Maui Condo with Ocean Views and Spectacular Sunsets
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 All Day Electric Bike Rental. (W1)*One ticket per...
Ko Olina Beach Villas 410: 4th Floor Ocean Front, Gourmet Kitchen, Private Lanai
Step into the world of luxury at Ko Olina Beach Villas B410 by Gather. Located on the fourth floor, this magnificent villa offers an awe-inspiring direct ocean front and luxury finishes. This two bedroom, two bathroom villa is the perfect space for up to four guests.The...
Kona Coffee Mountain Getaway, in Holualoa
Completely renovated 2nd story home. Everything is brand new! New beds, new appliances, new cabinets and flooring! The house is 2 bedroom, 1 bath with shower and tub. Both bedrooms have a Cal king size bed. Living room with dining area, WiFi and TV, a full kitchen and...
AMAZING OCEAN VIEW Popular White Sands Village Steps To The Beach!!!
Hale Lihi LaniOcean View Vacation Rental at White Sands Village. We are located 4 miles south of charming Kailua-Kona Village and directly across from Kona's spectacular Magic Sands Beach. You will enjoy beautiful ocean views and dreamy sunsets from our large covered...
Kaanapali Royal B201: Your Dream Hawaiian Retreat
🌴 Escape to Paradise: Your Dream Vacation Awaits at Kaanapali Royal B201 🌺Imagine waking up in the heart of Kaanapali (Kāʻanapali), where the gentle sounds of swaying palm trees (nā niu) and the scent of tropical flowers (nā pua) welcome...
🏖️Concierge Included| No Stairs | Ocean View | vrKCV
vrKCV - Country Club Villas 230, Professionally Managed by Kona Coast VacationsDiscover the essence of island living at Unit 230 of the Country Club Villas in Kona, Hawaii. This charming 2-bedroom, 2-bathroom retreat offers an idyllic getaway in the desirable Keauhou...
MOST STUNNING Oceanfront Views, A/c, Washer/Dryer, Kitchen, Elevator, Beach 0.5m
2 Bedrooms, 2 Baths, Sleeps 6THIS CONDO HAS THE MOST STUNNING OCEAN & COVE VIEWS, BARRING NONE!!! THE WAVES CRASH RIGHT IN FRONT OF THE PATIO INTO THE MAGNIFICENT COVE BELOW. The occasional spray is the cherry on the top. The unit is fully air-conditioned.The living and...
Maui Resort Rentals: Honua Kai Hokulani 246 - 2BR w/ Partial Ocean AND Lush West Maui Mountain Views!
Hokulani 246 is an opulent two bedroom partial ocean view suite offering views of the Pacific Ocean and the awe-inspiring West Maui Mountains. As the second two bedroom back from the front you will find that this suite is well situated to enjoy what Maui is known for,...
Luxe Tropical Retreat w/ Private Pool, Spa, AC, Golf Cart Included
This newly constructed split-level home features an open floor plan, only the finest finishes, and its own pool and jacuzzi, along with access to the KaMilo pools, fitness center, and other recreational facilities. Luxuriously appointed, it creates a peaceful atmosphere...
3BR/3BA Penthouse: Central A/C! Short Walk 2Beach!
Welcome to BlueTideVillas! This is a VERY spacious (1650+ square feet), top floor (2nd & 3rd), corner Penthouse, 3BR/3BA with two private lanai's to sit on and enjoy your favorite tropical drink. This is one of the most demanded units in all of Poipu due to its central...
Puako Oceanfront Paradise
Enjoy your personal piece of paradise while staying at this private oceanfront oasis in Puako. Relax in the hammock on a lush yard while listening to the waves. Enjoy prime snorkeling or diving just steps away from the yard. Cool off or exercise in the lap pool. Unwind...
Poipu Crater 20 - A/C, Close to Beaches, Shopping, Golf and Restaurants
POIPU CRATER 20 AT KOLOA KAI VACATION RENTALSA Unique Hawaiian Retreat Inside a Tropical CraterWelcome to Poipu Crater 20, a charming and secluded two-bedroom condo nestled within a dormant volcanic crater. Surrounded by lush tropical gardens and vibrant birdlife, this...
New Aloha Ilikai 1Free Parking<br>(1777 Ala Moana BLVD)
ALOHA! Fully Renovated in June of 2025 / 1 free parking(There is a top-quality water purifier inside the unit, so there is no need to buy bottled water.)Perfect for couples, families, solo travelers, or business stayWe offer the ultimate Waikiki experience, combining...
Modern Oceanfront Condo with Stunning Views, Perfect for Any Getaway #705
Spectacular Maui condo! This bright and beautifully, modern condo is perfect for honeymooning couples, anniversary stays, family getaways, and those just looking to escape to their own tropical retreat. Mana Kai Resort is a favorite oceanfront community among travelers...
Secluded Ocean View Sleeps 14 EASTER PRICING Book 10 nights for the price of 7
Looking for the perfect tropical retreat? MAUI TURTLE COVE is your ideal vacation home! Enjoy Maui in a beautiful 5 bedroom home with mature tropical landscaping and beautiful ocean views, including breathtaking Molokai Island! Just a short 3-minute walk down a private...
Papala Place at Kahakai Estates by Gather: Luxe Poolside Oasis
This private four-bedroom retreat within the gated Kahakai Estates blends elegance, space, and island charm. With partial ocean views, lush gardens, and a resort-style pool area, Papala Place offers a serene escape just minutes from Kailua Kona’s beaches, shopping,...
Ocean Front Studio , perfect for a romantic getaway ....
Unit 321 is in the Konea Tower of Honua Kai.The Ocean View Suite on the 3rd floor overlooks the Adult ( quiet) pool and steps away from Dukes Restaurant and Bar You have full access to the resort and your key gives you access to the fully equipped Gym that is also in...
Luxurious Poipu condo - Walk to multiple beaches - Central AC - Wifi - Pools
Welcome to your slice of paradise in Poipu!Nestled in the prestigious Regency @ Poipu Kai Resort, our newly furnished, air-conditioned, 5-bedroom luxury condo offers an oasis of comfort and elegance on the beautiful island of Kauai. Perched on the 2nd and 3rd floors,...
PARADISE RV .You won't forget your time in this romantic, memorable place.
Experience the magic of Maui on your terms! Our camper vans provide you the freedom to explore hidden beaches, wake up to sunrise on Haleakala. Tailor your Hawaiian adventure. Enjoy Maui beautiful!!!!