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.
Family luxury villa w/Pool Hilo — 5 min from the beach!
4 Bed, 4 Bath, sleeps 8, with a poo/ spa and next to secret beach 5 minute walk. Nice Views of Pacific Ocean, Mauna Kea or just relax with this amazing property in the sunny beach area of Hilo. Peaceful Hawaiian hideaway with plenty of room, ocean views, and privacy!...
Picture Perfect Oceanfront Condo at Mana Kai Resort
Hawaii Tax ID: TA-078-732-6976-01TMK: 390040230067Beautifully remodeled two bedroom in the desirable South Kihei area! Enjoy breathtaking Oceanfront views right from your lanai, see whales and turtles as you dine and relax in your home away from...
South Shore Ocean View 1 BR Condo Poipu Sands 112 Close to the Beach Upgrades
Life is a Beach at this beautiful south shore condo, located on the ground floor just a short walk from the Shipwreck beach. With newly upgraded appliances, bed and mattress, master bath vanity and cabinets, paint, Wi-Fi, cable, and Flat Screen TV. It's not too late to...
Halii Kai Waikoloa 2B-Private Ground-Floor, Golf Discount & Oceanfront Club!
Indulge in a premium golf experience with our exclusive GOLD GOLF KINGS' CLUB membership, offering discounted rates and access to one of Big Island's top resorts.Waikoloa 2B condo features a spacious private master bedroom with an en-suite bathroom, a guest bedroom with...
Reduced rates at Modern North Shore Getaway w/ AC!
Enjoy the best of Kauai’s North Shore at this beautifully updated condo in Princeville—one of the island’s most desirable communities! Surrounded by lush gardens and tropical scenery, this ground-floor retreat at The Plantation at Princeville features a spacious...
Luxurious condo with 2nd floor ocean & whale watching view, wifi, cable TV, DVD
With a unique, luxurious remodel, you'll appreciate what has been described as the nicest unit in the complex. Don't settle for just anything when you can make that Maui vacation a truly lasting memory.The unit has king- and queen-size beds and a sleeper sofa, robes for...
Hale Kona Kai 404 - Find your Beach with Kona Beach Properties
HALE KONA KAI UNIT 404 SPECIAL FEATURES: The bedroom and living room are separated by sliding french doors instead of the traditional closed rooms. This allows the condo to open up into one large space. A great benefit to this layout is that the AC works much more...
MRR Presents Kaanapali Ali'i 2103 - Gorgeously Remodeled 2BR+DEN w/ Stunning 10th-Floor Direct Ocean Views!
Never before available for vacation rental, this gorgeously remodeled 2br+DEN residence boasts an extra-large floor plan and direct ocean views from a stunning 10th-floor interior courtyard location. Enjoy over 1850 sq ft of interior living area, an extra-large balcony,...
Updated Poipu Home: Large Deck w/ Scenic View
Experience tropical scenery and island breezes at this updated 3-bedroom, 2-bath Koloa vacation rental! Boasting a large deck, spectacular ocean and mountain views, and a fantastic location minutes to Shipwreck Beach, this home allows your family to enjoy their Kauai...
Secure 1-bedroom with full kitchen, Washlet, parking & ocean/sunset views!
Four Paddle #1704 – 2140 Kuhio Ave.Enjoy partial ocean views and a great location from this newly remodeled, contemporary one-bedroom condo (553 sqft plus lanai) with central A/C and beautiful new ceramic flooring! 2-person max.Gourmet marketplace Dean & DeLuca is...
🏖️Walk to Kona Town | Ocean View | Concierge Included | vrKCV
vrKCV - Kona Pacific E630, Professionally Managed by Kona Coast VacationsWelcome to Kona Pacific E-630! This 1-bedroom, 2-bath condo offers serene ocean views and the perfect location within walking distance to Kailua-Kona's vibrant downtown and beach. Thoughtfully...
Beautiful Ocean View Alii Kai Condo
We are blessed with our 2021 renovated, beautiful ocean view, building 7 Alii Kai condo. We are willing to share it with clean, conscientious vacationers. This is an ideal place to stay for exploring the abundance of year-round activities in Kauai. If you compare other...
Aloha Condos, Polynesian Shores, Condo 213, Oceanfront
Polynesian shores is a beautiful, recently renovated (2020) oceanfront resort on the charming, rocky shore of Honokowai, Maui, just 6 miles north of Lahaina- town. Enjoy swaying palms, fragrant plumeria trees, the calming sound of waves breaking against the shoreline,...
Come for your dream vacation! B206
A LITTLE BIT ABOUT OUR CONDO....Lokelani B206 is a mid-level two bedroom unit that has two full bath rooms which makes it perfect for that family dream vacation. With a NEW king bed in the master bedroom, two new twins in the second bedroom, (which can be made up as a...
Ocean View, Ground-Floor Condo w/ Lanai, WiFi, Shared Pool - Walk to Beach
Kepuhi Beach Resort #1182Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'This ground-floor condo, located in the middle of the villas complex at Kepuhi Beach Resort, provides...
Ocean view with lanai in Beachfront Sugar Beach Resort!
* Please note: The pool, hot tub and pool deck will be closed for maintenance in September, starting the 2nd Monday of September, from Sept 8 - 19, 2025 * As well, the living room pull out couch was replaced with a brand new couch January 2022.On the beautiful south...
Ground-Floor Air Conditioned Condo Near Beaches w/Free WiFi, Shared Pool/Hot Tub
Regency 810Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'If you're looking for fun in the sun on your Hawaiian vacation, a Regency Resort condo can't be beaten! Just an...
Maui Resort Rentals: Honua Kai Hokulani 510 - Spacious 5th Floor 2BR w/ Partial Ocean & Mountain Views
Hokulani 510 is a luxurious two-bedroom suite offering gorgeous views of both the blue Pacific Ocean and the lush West Maui Mountains. Suite 510 affords a perfect opportunity to gather, reconnect, and celebrate. The suite can accommodate up to six guests in two...
Family Vacation with 8 pass Honda Mini van included. Ocean and mountain view,
Aloha and Mahalo, This Family condo feature 3 bedrooms, 3 bathroom unit is a great vacation rental for larger families that have a hard time finding a place for a large family. It is on the 3rd story. .There are no elevators. The view is lovely from the Lanai.This is a...
Mountain view deluxe vacation rental, AC, close to beach, WiFi, pool, parking
Waikiki Banyan #2609-T2 – 201 Ohua Ave.Great Ko'olau Mountain views from this deluxe air-conditioned one-bedroom vacation rental suite (533 sq.ft. plus lanai with table and 2 chairs)! 4-person max.The Waikiki Banyan is a favorite of repeat visitors with its host of...
Hale Halai beautify large home perfect for families & small company retreats
This 5000 square foot spacious home with an open floor plan is excellent for families, friends, and co-workers to gather and enjoy each others company. It has 7 bedrooms, 5 bathrooms, A/C, and a private pool. Tropically landscaped grounds with a BBQ and a spacious yard....
Lovely beach condo with lanai, AC, modern kitchen, pool & grills - walk Old Town
Kona Plaza 307Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Within a quick walk of the beach, this charming condo in Kona Plaza boasts a breezy covered lanai with peekaboo ocean...
Hale Kamaole 207 Second floor condo, easy access to best beach on Maui!
New everything, 2014 remodel. Travertine floor from entrance to Lanai, new carpet installed in bedroom. All new appliances. Bedroom has new King bed. Living room provides queen Hide a bed and comfortable siting chairs. Bath has tub/shower enclosure. Kitchen & bath just...
Kolea 14L: 2 BR, 2 BA Condominium in Waikoloa, Sleeps 6
Kolea 14L is one of the few two bedroom villas at Kolea at Waikoloa Beach that has a pleasant, open ocean view. The villa has been thoroughly furnished to offer the utmost comfort in a vacation home.As you walk into the villa you will be struck by the spaciousness and...
2 bdrm 2 Bath Condo with Partial Ocean Views, Steps away from Kamaole III Beach
Spacious 1,200 square foot (with lanai) 2 bedroom 2 full bath condo with high beam vaulted open ceilings (Open air concept, bedroom walls do not extend up to the vaulted ceiling) and panoramic windows, across from the golden sands of Kamaole III Beach. The condo kitchen...
Affordable 1 B/R Private Condo across from Kamaole II Beach (KKN252)
We have a welcoming second floor, corner, one bedroom 723 sq ft condominium, at the Kihei Kai Nani complex across the street from a beautiful beach, Kamaole II, in Kihei (200 meters to sand). The Condo faces the garden, which makes it wonderfully private and quiet....
Maui Resort Rentals: Honua Kai – 5 Total Bedrooms, 6th Floor Stunning Deluxe Ocean and West Maui Mountain Views!
This phenomenal sixth-floor offering that pairs two neighboring residences for nearly 2700 sq ft of combined interior living space. Your group will enjoy five luxurious bedrooms and bathrooms, two modern kitchens, and two expansive lanais featuring unparalleled views of...
Second floor studio with shared pool & hot tub, ocean view, washer/dryer
Kona Bali Kai #265Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Bask in front of an ocean view on your own private screened-in lanai while sipping a refreshing beverage - it's all...
Includes Hilton Pool Pass for thru June 2025. Waikoloa Colony Villas 505
505 Waikoloa Colony Villas. Luxurious. Relaxing. FunThis vacation rental is professionally managed by ResorticaHawaiiNewly Remodeled!Waikoloa Colony Villas 505. Please scroll down for detailed information505 Waikoloa Colony Villas. Luxurious. Relaxing. Fun. Nestled in...
Chic condo in oceanfront complex with resort amenities & wraparound lanai
Kona Makai 4-106Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Relaxation comes easy at this Kailua-Kona condo, located at the oceanfront Kona Makai Condominiums. Make the most of...
LOVE DA BLACK ROCK OCEAN VIEW WHALER ON KAANAPALI BEACH - APRIL / EASTER HOLIDAY
MAKING YOUR NEXT MAUI STAY A TRULY MEMORABLE EXPERIENCE. Our beautiful Whaler studio condo is all about views, privacy and comfort. It is located on the 10th floor of Tower 1 with 180 degree unobstructed views of the ocean, Isle Molokai, Black Rock and the North...
Heart of Waikiki! Close to Beach! Free off-site parking!
Regency on Beachwalk #22 – 255 Beach WalkYou'll really appreciate the convenient location of this fully-furnished 2nd-floor end unit condo (494sf plus 145sf lanai with table and chairs, for a total of 639 sf) at Regency on Beachwalk, right in the heart of Waikiki and...
Split AC in your Island Home! Direct Ocean Views!
BOOK NOW FOR Summer/Fall!Aloha from one bedroom Makani Sands #205, a beautiful oceanfront condo on Maui's scenic West Side. You are surrounded by traditional island design and Hawaiian Art. This condo has every convenience and luxury to make your vacation in paradise...
A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach
TA-061-740-4416-01GE-061-740-4416-01Air Conditioned 1 Bedroom and 1 Bath near Hookipa, sleeps 4. Beachy chic apartment in Kuau on the north shore of Maui. Located next to Mama's Fish House and down the road from world famous Hookipa Beach Park. Bright and comfortable...
Stylish and contemporary Hale Kukui OIa
Bright and beautiful, meticulously maintained, 2 bedroom plus loft, 2 bath custom home with hot tub and ocean views located in Kalapana Seaview Estates, Pahoa, Big Island Hawaii. Located just off the historic Red Road near Kehena Beach and Pohoiki, this is the perfect...
Pono Kai A306 Kauai Oceanfront Penthouse!
Paradise as you imagined Penthouse in the heart of wonderful Kapa'a Town! Pono Kai Condominiums are perfectly located RIGHT ON THE OCEAN a short drive from the airport and within walking distance of downtown Kapa'a with its restaurants and shops, parks and activities....
Maui Resort Rentals: Honua Kai Konea 320 – Upgraded Corner 2BR w/ Delightful West Maui Mountain Views
Konea 320 is a remarkable 2BR/2BA suite boasting a spacious corner location. Oversized picture windows bring the lush West Maui Mountain views right into the comfort of your living room. Recently upgraded with new wood grain tile flooring and new furniture, Konea 320...
Alii Villas#128 DIRECT OCEANFRONT, GROUND FLOOR, 2 BEDROOMS, 2 BATHROOMS!
WOW! Gorgeous Kailua Bay views from this 2 bedroom, 2 bathroom fully furnished oceanfront condo located on Ali'i Drive in Kailua-Kona! Spinner dolphins are visible from the spacious lanai while sipping Kona coffee or cocktail! This is a ground floor unit, with one...
Beautiful Sunset Views, Ilikai Hotel #410 Free WIFI, No Resort Fees!
*Construction Update* Spall repair and exterior painting will be ongoing outside of the unit from August through mid-October 2025. Access to the lanai will remain available during work hours; however, please note that noise may be present as contractors work on this...
Time Beach @ Grand Van Kleef
Our mission is to provide a tranquil and serene vacation spot where you and yours will truly relax.Aqua Bedroom: air-conditioner, dresser, queen bed, closet and bathroom adjoined. The decor is meant to entice you to sleep well and create magical memories – yes! ☺....
KBM Resorts | FREE CAR | Honua Kai Hokulani | Ocean view | 2-Bedroom Condo, Close to Beach & Pool! HKH-242
Stylish 2-bedroom villa with stunning ocean views, remodeled interiors, luxury tile flooring, and seamless indoor-outdoor living-perfect for a relaxing and elegant Maui escape with the whole family.** Limited Time Special Offer: Book any KBM rental home in Hawaii for 6...
Beautifully updated home w/ private hot tub, spacious backyard and free WiFi
Tiki HaleOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Located in a peaceful neighborhood in the heart of Princeville, surrounded by the elegant Makai Golf Club, Tiki Hale has the...
Direct Ocean Beachfront!! One bedroom one bath one parking!!
Direct Ocean Beachfront!! One bedroom one bath one parking!!Located in the middle of the desirable San Souci. Direct Oceanfront One Bedroom/One Bath with huge lanai directly overlooking Sans Souci Beach. Enjoy the view of the calming Pacific Ocean from your lanai. Watch...
Hale Hui Kai 312 Panoramic oceanviews of Keawakapu Beach
This private oceanfront condo is on the third floor of the building ...about 20 steps along the pathway leads to the gem of south Maui, Keawakapu Beach!Keawakapu Beach, located on the south shore of Maui, Hawaii, is known for its stunning natural beauty and tranquil...
My Hawaii Oceanfront 2 Bedroom Vacation Rental - Kona
Centrally located, My Hawaii Vacation Rental, "Kona Luana", is within a ten minute walk of Kailua-Kona Village. There are many attractions some of which include Kailua-Kona pier, variety of dinning options, waterfront shopping, Farmers Market, coffee shops and friendly...
Rare, Spacious Penthouse, Big Ocean and Mountain Views, Great Location, AC
Hotel Zoned Accommodations: Condominium - 3 Bedrooms - 2 Baths - (Sleeps 6)Professionally Cleaned Condo, No-Contact Check-In/Check OutNewly installed AC throughoutThis spacious 1145 sq. ft. two bedroom and a loft bedroom, two bathroom condo offers panoramic views of...
Amazing 🏄♀️ Oceanfront Penthouse 🐬 Newly Renovated! - Banyan Tree 403C 🌅
Complete oceanfront penthouse with two bedrooms and two condos at the top floor. Wondrous views of the ocean, reefs, moon and sunset plus all the facilities that your family and you enjoy.. Surfers and long waves have entertained visitors from all over the world on one...
Maui Sunset A421 ~ Spectacular Sunsets from this 2 Bedroom, 2 Bath Condo!
One of the BEST OCEAN VIEWS @ Maui Sunset! Two bedroom, two bath ocean view fourth floor condo. Good walking, windsurfing, kitesurfing beach fronts this oceanfront condo complex in North Kihei. A couple of minutes away from Kamaole Beach I, one of the great beaches on...
Pali Ke Kua 211 .. Ultimate Oceanfront view!
Beautifully decorated spacious 2-bedroom, 2-bathroom condo offers the ultimate oceanfront view in incomparable Kauai. This is the Hawaii of your dreams. From sunrise to sunset, the view from Pali Ke Kua 211 is nothing less than spectacular. Overlooking the Pacific...
Sandcastles - Anahola Beachfront Estate with Hot Tub & Enclosed Yard
Sandcastles TVNCU#1305Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'This majestic home, Sandcastles, has vaulted ceilings and large sliding glass doors that open to a spacious...