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.
High-end condo with open-concept design
E Komo Mai “welcome” to Kapalua Golf Villa 25P 3&4! This 2-bedroom, 2-bathroom villa is nestled on the Kapalua Bay Course and can accommodate up to 6 guests. Enjoy cooking in this fully equipped kitchen that features granite counter tops and full-size...
Beautiful Ocean View Maui Sunset Condo - B213
Escape to the sunny shores of Kihei, Maui and experience the ultimate island getaway at our charming 1-bedroom condo. Nestled just a short 18-minute drive from the stunning Wailea Beach and 10 minutes from the pristine Kamaole Beach Park, you'll be perfectly positioned...
Your Oceanview Corner of Paradise: The perfect condo in the heart of Kihei.
This walk-up condo in the first building of Kihei Kai Nani is across the street from lovely Kamaole II, in a string of the some of the most beautiful beaches on Maui. If you use the map feature, you can see this is in building one - 200 feet from the beach! Yay! Choose...
Outstanding Wailea 3 bed/2 ba Grand Champion #94 - big lanai and ocean views
Bldg. 10 - Unit #94 - New, New New. New roof, new carpet, new appliances, new bed - renewed throughout, an impeccable 3 Bedroom + 2 Bathroom paradise condominium at the Wailea Grand Champion Villas. This is the finest that Wailea Grand Champion Golf Villas has to offer...
Kahana Sunset B4B Early Summer Specials at OceanFront Condo Just Steps to Ocean
The Stice Team — Powered by Gather Vacations. Maui Born and Raised Professionals. Your Local Experts in Crafting Unforgettable Stays. Welcome to Kahana Sunset B4B, a beautifully remodeled 1-bedroom, 1-bath hideaway nestled in the boutique beachfront enclave of Kahana...
EL J222 Remodeled Studio w Pools Hot Tub AC Gym Cabana
Eldorado J222 Remodeled Studio with Private Beach Cabana 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,...
Sleeps 4, Full kitchen & AC. Pool, hot tub, tennis court, bbq grills! And Beach!
Aloha, Our studio condo is very cozy and clean! It sleeps up to 4 with a cal. king bed and a queen size futon. The pool, hot tub, tennis courts and bbq grills are all very close by. Located across the street is Kalepolepo Park, which has great beach access and the...
Fully Remodelled View Condo Near Waikiki Beach with Free Parking/WiFi
Hawaii Tax ID No. TA 200-103-3216-01, 2020 NUC No. 90/TVU-1102Contact Owner Debbie for more information.Please note: Pool and Recreation Deck will closed for upgrading in 2025-2026. No refund or discount will given during this period. The Condo is located one block from...
❤️PiH❤️ Family Tides ★ Five Bedrooms ★ Resort Pool & Waterslide Pass
Brought to you by Paradise in Hawaii Luxury HomesWelcome to the newest elegant home, Family Tides, in our Hawaiian Luxury Collection.Family Tides is a wonderful large single level 5 bedroom, 5 bathroom home. With two ohana (family) suites this home is the perfect...
Kauai Exclusive - Hale Awapuhi 2E - Oceanfront Luxury - Steps to the water
Hale Awapuhi 2E is among the most luxurious oceanfront properties in Hawaii. Exclusively gated, this boutique 9-unit project offers panoramic ocean views and beach access just steps from the front door. Boasting three bedrooms with A/C, this elegantly appointed...
Snowbird-friendly condo with ocean view, pool, washer/dryer, lanai, & grill
Kona Ali'i 502Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Conveniently located right on the bay with an unobstructed ocean view, you won't want to leave after staying at this...
Waipouil Beach Resort Beautiful Garden & Peek Ocean View!
Beautiful Garden & Partial Ocean View, a 1 Bedroom, 2 Bathroom Condo at the Top Rated, 1st Class Waipouli Beachfront Resort & Spa on the beautiful island of Kauai.There is Central AC in this condo as well as a full size washer and dryer for laundry!Enjoy Oasis on the...
Great Unit with a Private Lanai
Our complex is zoned hotel/resort and therefore won't be affected by any future ban on short term rentals, which will be for apartment zoned units only, You can book with confidence and not worry about a cancelation. Unique qualities of this unit are its central...
Steps to the Beach, Dining and Shopping! Spring Specials! Inquire now!
Location is everything with this property. Not only are you less than two minutes from the beach and a large swimming pool, you are also walking distance from restaurants and shops of every kind. This unit is away from the street and on the second floor thus, very...
Haleiwa Waterfront House
LEGALLY LICENSED VACATION RENTALLocation, location, location! This lovely home is perfectly situated on a beautiful white sandy beach, at the end of a quit cull de sac. You will find all the space and privacy that one needs to enjoy a nice peaceful holiday. Historic...
Puamana 58-1 Oceanfront Comfort in Puamana
Located in Puamana, a 30-acre oceanfront gated community just south of Lahaina, this charming three-bedroom, 2.5-bath townhome offers a tranquil escape amidst Maui’s natural beauty. While the 2023 Lahaina fires affected parts of Puamana, including areas near this...
Unit 120 Island bliss with great views!
A LITTLE ABOUT THIS CONDO....Welcome to Polynesian Shores 120—your perfect island retreat! This beautifully designed condo embraces warm tropical décor, creating a cozy and inviting atmosphere.After a day of exploring Maui’s breathtaking beauty, unwind in the...
Resort Living Off the Beaten Path
The fabled North Shore of Hawaii is a hidden jewel off the beaten path. Enjoy wonderful dinners watching the sunset on your peaceful breezy lanai.This spacious condo has 1 bedroom, 1 bath, plus loft with 2 queen beds and is fully air conditioned and can sleep 6. Kuilima...
🏝 Private Home, Large Lanai -2 Minute Walk to Poipu Beach! 🐠
Welcome to Kipuka Hale, a beautiful designed, newly renovated home. Located in a quiet, stunning neighborhood just two minutes to the world famous Poipu Beach. Our guests have full access to Poipu Beach Athletic Club, which includes a pool, hot tub, basketball/tennis...
1BR Top Floor, Beachfront, Stunning Views, & Poolside Fun Kihei Kai Nani
This property is hotel zoned, and not being affected by the recent proposed legislation.LOCATION! LOCATION! LOCATION! Welcome to Kihei Kai Nani!Kai Nani is centrally located in sunny South Kihei with easy access to famous Kamaole II Beach Park and walking distance to...
LAST MINUTE SUMMER DEALS- Oceanfront getaway in Kihei, Maui.
A perfect oceanfront view from the living room or lanai. Make a coffee or mix up your favorite beverage in the fully appointed kitchen, then sit on the lanai and look at sunrise or sunset from this oceanfront unit. It has everything you need to be the perfect home base...
Wailea Elua Village 1001 - 2 Bedroom Oceanfront Condo
Wailea Elua Village #1001 is a stunning oceanfront sanctuary that has recently undergone a complete transformation. For discerning travelers who enjoy the best of Wailea, the extended outdoor living space allows you to enjoy panoramic ocean views while relaxing with a...
KKSR#3203 DIRECT OCEANFRONT, 2ND FLOOR, REMODELED, SPECTACULAR VIEWS!
Keauhou Kona Surf & Racquet Club#3-203 DIRECT OCEANFRONT, 2ND FLOOR OF BUILDING#3 in complex! #3-203 is extensively upgraded & remodeled.A truly beautiful oceanfront condo in a gated complex with unobstructed ocean and Kailua town views. Elegant furnishings in this...
Island oasis on golf course w/private lanai, pool, tennis, WiFi, & ocean views
Waikoloa Villages E108Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Find yourself enjoying a favorite beverage while overlooking the signature sixth hole of The Village Course at...
Spacious studio condo with private lanai, kitchenette, & shared pool
Island Colony 3414 - 30-Night MinimumOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Island Colony is a gorgeous, modern building in the heart of Waikiki that offers guests access to...
New Listing! Palms at Wailea 1501! Ground floor with Ocean views!
Welcome to our magnificent Oceanview retreat, nestled within the highly coveted Palms at Wailea. This nicely updated ground floor 1-bedroom, 2-bath unit promises an idyllic Hawaiian escape, complete with all the essential comforts and amenities you could desire.Step...
Amazing private home with AC, Pool, Garage, Hot Tub and Toys N27C
PROPERTY DESCRIPTIONWelcome to your immaculate North Shore oasis! This 3-bedroom, 2.5-bath home is surrounded by tropical foliage, with a lagoon-like pool with a hot tub and expansive sun deck. This upscale rental is a fantastic spot for families, weekend excursions,...
Great 2025 Rates!! Koa Resort Unit 4I - Spacious and Beautiful 3 Bdrm / 2 bth
Koa Resort Unit 4i offers an ideal setting for a serene and enjoyable vacation in a tropical paradise. Situated on the second floor, this renovated condo features three bedrooms and two bathrooms, accommodating up to six guests comfortably. Each bedroom is equipped with...
OCEANFRONT, gated Kapalua Bay Villa 29B4 - Molokai view, steps to water!
Discover the beauty and tranquility of Maui at this newly renovated 1-bedroom, 1-bathroom villa in the exclusive oceanfront community of Kapalua Bay Villas. Nestled within a secure, gated 16-acre enclave of lush tropical landscape, this elegant retreat offers...
Mahina Kai: Large Tropical Modern Home with Pool, Ocean & Koko Head Views & A/C
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.Exciting Updates Coming Soon: This property...
Sleeps 6! Palm Villas B23, 2 bed plus 3rd bedroom loft! Walk to Beach!
Please be advised that during the month of September 2025 the pool will be closed for maintenance.There will possibly be noise from the pool area as it is getting refurbished. This beautiful and spacious condo at the Palm Villas at Mauna Lani Resort is located on Pauoa...
Kamaole Sands 4-306 - Steps to Kamaole III Beach - Split AC + Pool + King Bed
Welcome to Kamaole Sands 4-306 - a beautifully remodeled, third-floor condo designed for comfort, luxury, and an authentic Maui experience. This bright and airy one-bedroom retreat accommodates up to four guests and features a fully upgraded interior, including a modern...
Keauhou Punahele Golf Course and Ocean View
Hawaii, Big Island, Kona, Keauhou Punahele, golf course with the ocean in the background. The condo is located close to Keauhou Bay, Keauhou shopping center (with cinema) and snorkel/surfing beaches.We have owned this top floor 3 bedroom/3 bath room unit overlooking the...
Maui Banyan Q-109 | Tropical w/ Resort Amenities
Maui Banyan Q-109 is an idyllic condo for an idyllic vacation. Not only is the ground-floor unit across the street from Kamaole Beach II and a short walk from Kamaole Beaches I and III, but it’s also within a gorgeous resort that features swimming pools, tennis...
Island Life Retreat-Ocean Front-Beach Access
BEACHFRONT • GROUND FLOOR • WALK-OUT Step straight from your lanai onto a quiet stretch of white sand—your own authentic Hawaiian paradise. The reef-protected turquoise waters are calm and perfect for swimming, paddleboarding, kayaking, or simply floating in the...
🏖️Concierge Included | Ground Floor with Lake Views | vrKCV
vrKCV - Fairway Villas Waikoloa K3, Professionally Managed by Kona Coast VacationsFairway Villas Waikoloa K3Aloha and welcome to your tropical Hawaiian retreat at Fairway Villas Waikoloa K3. This beautiful ground-floor condo offers stunning views of the lush green 4th...
Delighted City View 1 BDRM Condo, Cal King Bed w/Kitchenette and Free WIFI!
Aloha from the Ilikai in Waikiki! Happy Vacations is a short-term vacation rental company. Property is located 4 minutes to the beach and 10 minutes to one of the nation's biggest outdoor malls, "Ala Moana Shopping Center". Friday night fireworks display starting at...
Centrally Located Downtown Gem
EVERYTHING IN TOWN AT YOUR FINGERTIPS! 5 bedroom, 4 bathroom, 2 kitchens, and an office/hang out room. Just minutes walking distance to all restaurants, sports bars, shops and beautiful beaches in the heart of kona, yet in a quiet neighborhood with no traffic noise in a...
Relax...Recharge...Retreat!
The perfect place to relax and recharge with the expanse of the ocean and sound of the waves right in front of you....plus every once in a while a rainbow will mesmerize you with its beauty....right from your lanai. A central air system in every room to cool you off!...
Sugar Beach Resort Oceanview 1 bed/1 bath - Last minute)deal $200/nt March 17-25
Come experience Paradise! 1 Bedroom Condo right at the water's edge. Perfect for those who want to get away from it all, this condo has everything you need. The living room and kitchen have full ocean views. This perfect piece of Paradise offers a beautiful white sand...
Hilton Waikoloa Pool Pass thru 2025. 18G Halii Kai
**Complimentary Late Check Out up to 7:00pm for stays of 5 nights or more between October 1-December 19, 2025 (stay must be complete by December 19th) based on availability at the time of booking. Valid for new bookings made September 24 or after. Please message us...
Stylish Unit Near Waikiki Beach with Free Parking!
Aloha from Midway Vacations! Our team of local hospitality experts is dedicated to turning your Hawaiian getaway into a reality. When you stay at one of our properties, you can count on a professionally cleaned and meticulously maintained experience. We're even...
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!
No Additional Fees except HI state tax.The Condo you are Renting is the Condo in the Pictures. 715 S. Kihei Rd., Kihei, HI 96753 Unit 254Purchase Traveler's InsuranceAloha! When you rent this condo, you will be renting from me, Kevin. I own, manage and maintain this...
April rates ONLY 129/nt ! Accommodates 6 guests/ 2 BEDROOM !
Charming Ground-Floor Retreat at Kihei Holiday just steps away from the renowned Sugar Beach, this beautifully updated 2 bedroom, 1-bathroom condo offers a serene and inviting escape to Maui. Beachfront Access & Seasonal Whale Watching just across the street! Both...
Polo Beach Club 508 - 2 Bedroom Oceanfront Condo
Polo Beach Club 508 is a stunning oceanfront vacation rental located in the heart of the luxurious Wailea area of Maui. This two-bedroom, two-bathroom condo offers an exceptional blend of comfort and elegance, accommodating up to six guests. Positioned on the fifth...
Aloha Suite Near the Sea II, 3 Block Walk to Beach
TA 028 872 2944 01, STR Permit # 2025-STR-482 expires 10/24/26, TMK 260230500087Convenience & Location! Just 3 SHORT BLOCKS TO WAIKIKI BEACH! Enjoy the ocean with gorgeous sunsets day after day. Fun shopping, great restaurants & entertainment all around you!This studio...
Waipouli Beach Resort Exquisite Luxury VIP Oceanfront Condo! AC Pool
Oceanfront! Exquisite Luxury VIP Oceanfront Condo in highly desirable "A" Building at the #1 Ranked Waipouli Beach Resort & Spa on Beautiful Kauai offering stunning Direct Oceanfront views from every room with delightful watercolor sunrises, whale watching (November to...
Spacious, Luxurious, Tropical Townhouse Style Condo For A Truly Aloha Vacation
Aloha Hale is a one of a kind, 2 bedroom, 2 1/2 bath, fully appointed town house style condominium that is located near the calm, protected harbor and beach of Keauhou Bay. The downtown Kailua-Kona area, on Alii Drive, is a short 10 minute drive or take the Kona Trolley...
Stunning ✨ Comfortable and Well Decorated Property 🌺 Incredible Views! 🏖 White Sands 318
Short distance away from Magic sands beach but without road noise! (less than 100 yards from the beach) Enjoy watching body surfing, boogie boarding, and beach activities while drinking a beverage on your lanai. Enjoy amazing sunsets and the crash of ocean waves while...