Hawaii Vacation Rentals – Island Condos, Beachfront Homes & Luxury Villas

Hawaii Vacation Rentals features curated stays across all islands - from beachfront condos to luxury villas - providing travelers with comfort, privacy, and a memorable island experience.
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Wailea Grand Champions | 111

Wailea Grand Champions Villa 111 is a spacious two-bedroom, two-bath vacation rental condo that accommodates up to six guests, making it an ideal choice for families or friends traveling together. The first bedroom features a comfortable king-sized bed, while the second...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Wailea, Hawaii

OCEAN VIEW 2 Bdrm condo with Secluded Beach - Kahana Sunset C7

Kahana Sunset OCEAN VIEW, newly remodeled 2 bedroom, 2 bath split level condo on secluded Keonenui Bay Beach.Heated Swimming PoolKiddie PoolBBQ AreaAir conditioningSecluded white sand beachTurtle SanctuaryFree parking and NO Resort Fees!This beautiful, 2-level,...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Lahaina, Hawaii

5-star and rave reviews. Amazing views. Newly furnished. Specials for April/May!

SPECIAL RATES for the 2025 Fall Season! Relax in what feels like your open-air home in paradise! Stunning views. Savor the outside air and breezes on your lanai. Superbly maintained. Consistent rave reviews (for years as we are original proud owners).Discounts for stays...

🛏 3 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 8
📍 Ko Olina, Hawaii

D35 Kona Reef - True Oceanfront & Top Floor! AC throughout!

Located just outside the heart of Kailua- Kona, this ocean front condo is your ticket to paradise! Just minutes from town, a short walk will take you to some of the finest dining and shopping destinations on the Big Island. Our modern, updated condo serves as the...

🛏 2 Bedrooms
🛁 1 Bathroom
👤 Sleeps 4
📍 Kailua-Kona, Hawaii

New "Beachy" 1BR, 2 Bth Kihei Condo w/Ocean/Mtn View-No Resort Fees!

It's cold and rainy outside...but not in Maui. We invite you to come and visit our condo and enjoy not only our 1 BR, 2 bath, full kitchen, LR, DR and no resort fees condo but also our private oasis. Palm trees are swaying, tropical breezes, island birds singing their...

🛏 1 Bedroom
🛁 2 Bathrooms
👤 Sleeps 4
📍 Kihei, Hawaii

Mauna Lani Terrace G102 Lagoon View Condo Beach - Restaurants, Bars Waterfront

⭕ UPSCALE LUXURY SUITE. LAGOONVIEW TERRACE #G102 ⭕ LARGE 1,150 SQ FT. WATER VIEWS OF LAGOON. COVERED LANAI ⭕ TWO MINUTE WALK TO OCEAN. 5 MINUTE WALK TO RESTAURANTS BARS ⭕ NO STAIRS! CENTRAL AIR CONDITIONING ⭕ FLOOR TO CEILING GLASS. LAGOON VIEW • Upscale...

🛏 1 Bedroom
🛁 2 Bathrooms
👤 Sleeps 2
📍 Kamuela, Hawaii

Ohana Anini - Enchanted Beachfront Home on Kauai's North Shore

Mana Kauai Island Vacations Presents Ohana AniniReady to experience all of the beauty and adventure that the north shore of Kaua’i has to offer? Stay at our spectacular Ohana Anini beach house with breathtaking ocean views, gentle trade winds, and air conditioning in...

🛏 4 Bedrooms
🛁 4 Bathrooms
👤 Sleeps 11
📍 Kilauea, Hawaii

Hale Hui Kai 211 Large Lanai overlooking the beach

South Maui oceanviews from both bedrooms and the living room/kitchen. This private oceanfront condo is on the second floor of the south side of the building ...about 30 steps along the pathway leads to the gem of south Maui, Keawakapu Beach!Keawakapu Beach, located on...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Kihei, Hawaii

MAUI IS OPEN! Come visit!Westin Kaanapali Ocean Resort-beautiful 2 bedroom villa

Reservations are available in weekly (7 night) increments with arrivals and departures on Fridays, Saturdays, and Sundays only. The Westin Ka'anapali Ocean Resort Villas is a gorgeous beachfront resort with luxury villas. Enjoy this villa and Maui's most spectacular...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 8
📍 Lahaina, Hawaii

Ocean & Diamond Head Exclusive Panoramic PH Condo w/Parking & Near the Beach

This property requires a minimum 30-day rental. Book with confidence—professionally managed by Ali'i Beach Rentals, an award-winning property management company.The Waikiki Landmark high rise is located at 1888 Kalakaua Ave. on the main strip of Waikiki. Situated in...

🛏 3 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Honolulu, Hawaii

BEACH LUX VILLA with AWESOME VIEW! CLICK on “About this Property” for a TOUR!

If you are looking for luxurious, yet affordable, accommodations in a premier location, you have found it. The Grand Champions Villas are located in the heart of Wailea on Maui's sunny south shore - where the weather is just a little bit better than anywhere else on the...

🛏 1 Bedroom
🛁 2 Bathrooms
👤 Sleeps 2
📍 Kihei, Hawaii

Maui's Premier Vacation Home: New Pickleball Court and Unmatched Luxury for Family Reunions

UPDATE: Starting March 20th, guests will enjoy our newly built pickle ball court, available for your private and exclusive use, located on property. Upon entering this gated estate, you'll instantly feel a sense of calm as you'll sense you have arrived in paradise. No...

🛏 7 Bedrooms
🛁 7 Bathrooms
👤 Sleeps 28
📍 Lahaina, Hawaii

Kolea Landing Modern Beach House w/ Double Suite and Third Bedroom Option

Aloha and Welcome to Kolea LandingA short walk (less than 400 steps to be exact) and you will be relaxing at Lanikai Beach! Our 2,200 sf guest house is the perfect blend of island and modern living. Our guest house has a master bedroom (king bed) with an en suite...

🛏 3 Bedrooms
🛁 1 Bathroom
👤 Sleeps 6
📍 Kailua, Hawaii

Truly Oceanfront - Rare 3BR - Amazing Sunsets & Awesome Views - SunsetShoresMaui

Truly DIRECT OCEANFRONT 3-bedroom END UNIT condo on the shoreline of Maui's beautiful west coast. SunsetShoresMaui offers unbeatable PANORAMIC OCEAN, ISLAND & SUNSET VIEWS from our nicely-upgraded, recently remodeled condo, located literally steps from the shoreline....

🛏 3 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 6
📍 Lahaina, Hawaii

Affordable Rates, Upscale 2BR in Oceanside Complex!

This large upscale 2BR/2BA villa is at Hali'i Kai, the only OCEANFRONT condo community within the famous Waikoloa Beach Resort. Besides a great condo, you will get to enjoy Hali'i Kai's unique Ocean Club. Perched at the ocean's edge, it features a multi-tiered...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 5
📍 Waikoloa Beach Resort, Hawaii

HIGH Floor w/Canal, Mtn and Partial Ocean Views! AC, W/D, WiFi, Pool,Parking!

Fairway Villa #2418 – 2345 Ala Wai Blvd(30-Night Minimum. ALL MONTHLY RESERVATIONS ARE SUBJECT TO APPROVAL.)NEW TO OUR INVENTORY! You'll love this corner property with its amazing Ala Wai Canal, mountain and partial ocean views and its proximity to shopping,...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 3
📍 Honolulu, Hawaii

RARE 2 BEDROOM, SINGLE LEVEL-2 LANAIS-WELL EQUIPPED-METICULOUS CLEANING-AC

Book with confidence, this nicely updated 2 bedroom, 2 bathroom (1086 sq. ft) single level condo. 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 available 24/7 to our...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Kihei, Hawaii

Elegant 3BR Pili Mai 12A w/ Pool, Golf Course Views & Modern Amenities

Welcome to Pili Mai 12A by Gather, the perfect three-bedroom, three-bathroom condo in Koloa. This ground-floor condo, alongside the picturesque Kiahuna Golf Course, offers garden views and a newly designed layout with central air conditioning. Each of the three...

🛏 3 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 6
📍 Koloa, Hawaii

Hale Honu -Turtle House Oceanview Luxury Penthouse

Located in the beautiful area of Waikoloa Beach resort, just 5 minutes from the beach, Restaurants, shopping, and nightlife. Enjoy the Penthouse suite in Vista Waikoloa and ocean views from the wrap around Lanai. This unit has been completely renovated with a modern...

🛏 2 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 4
📍 Waikoloa Village, Hawaii

SPRING BREAK SPECIAL! Lau'eki Estate ~ Hualalai ~ Sweeping Views ~ Infinity pool

Step through a tropical courtyard into Elegant Lalani Lau’eki Estate, a 4-bedroom retreat with a separate Ohana guesthouse, ideal for couple getaways or family gatherings. A breathtaking hallway frames ocean views from the expansive lanai, where you’ll sip coffee as...

🛏 4 Bedrooms
🛁 4 Bathrooms
👤 Sleeps 8
📍 Kailua Kona, Hawaii

Snorkel at Kam Beach Steps From Chic Resort Condo!

Sink your toes into the sand of heavenly Kamaole Beach Park III found just a quick stroll from this tropical chic 1-bed, 2-bath condo! Featuring an ideal location on the lush acreage of Kamaole Sands, this Kihei vacation rental inspires pure relaxation coupled with a...

🛏 1 Bedroom
🛁 2 Bathrooms
👤 Sleeps 4
📍 Kihei, Hawaii

Reserve Your 5 STAR Big Island Get-a-way ⭐⭐⭐⭐⭐

Looking for just the right place to enjoy your Big Island Hawaiian Holiday? Treat yourself to a fresh approach. Your own private 1 bedroom 1 bath cottage. Newly renovated, this delightful guest cottage is tucked away behind gates at the end of a cul-de-saq. The perfect...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 2
📍 Waikoloa Village, Hawaii

One of our best ON SALE & Wide Open (4/16- 5/8) ~ Must See OCEAN FRONT Villa ~

Welcome to Hale O Ho'okipa which translates in Hawaiian to 'House of Hospitality'.Truly one of the nicest ocean front villas in the Kapalua Bay Villa Resort! Some make this claim without conviction, but we have provided quality photos and a professionally produced video...

🛏 2 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 6
📍 Kapalua, Hawaii

Spacious 5-bedroom villa in charming Kukuiula with AC, WiFi

Escape to this marvelous villa in picturesque Kukuiula in Poipu. This superb property boasts 5 bedrooms, including 4 king beds and 1 bunk bed, perfect for larger groups. With 5 bathrooms equipped with luxurious amenities like a bathtub and shower, guests will feel...

🛏 5 Bedrooms
🛁 4 Bathrooms
👤 Sleeps 13
📍 Koloa, Hawaii

Waipouli Beach Resort Exquisite Ocean Front Condo in Oceanfront "H" Building

Oceanfront! Exquisite and Tranquil #1 Rated Oceanfront 2 bedroom, 3 bath condo at the beautiful #1 Ranked Waipouli Beach Resort & Spa on the 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 Beach...

🛏 2 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 8
📍 Kapaa, Hawaii

Walk to Ocean from house- close to BYU-H & Polynesian Cultural Cntr 3 bed 2 bath

Enjoy a slower pace in our family-friendly home, conveniently located only eight houses from the ocean in a local neighborhood close to Laie. We invite you to relax in our comfortable beds and huge cozy couch, or recline on the lanai chaise while reading a classic. When...

🛏 3 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 9
📍 Hauula, Hawaii

Mountain & Waterfall Views - Pool & BBQ

Hawaiian jungle paradise awaits you at Villas of Kamali'i. Welcome to this fabulous split-level townhouse with wonderful mountain and waterfall views. The spacious design is beautifully furnished and is loaded with amenities to make your stay an extraordinary and...

🛏 3 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 6
📍 Princeville, Hawaii

Sans Souci Unit 1001 - One Bedroom

Nestled on Kaimana Beach, this charming, fully furnished one bedroom in Sans Souci is just steps away from the ocean. The unit boasts a complete kitchen and offers wifi & cable for your convenience. Enjoy the proximity to the renowned restaurant Hau Tree, located at the...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 2
📍 Honolulu, Hawaii

Oceanfront Condo with A/C, 10 Steps to the Ocean, Ground Floor, Kuhio Shores 112

Kuhio Shores 112 is a quiet, private oceanfront air conditioned condo that is 10 steps from the water’s edge. No need to deal with stairs or elevators; simply walk out the sliding glass door, and enjoy the ocean’s majesty! The first-floor location allows easy access...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 2
📍 Koloa, Hawaii

Private, Comfortable and Cozy with Distant Ocean and Mountain Views

Boulay Inn is nestled on Kauai’s south side in rural Omao. It is your own secluded home away from home with all the amenities to ensure your comfort. There is a spacious airy living area, a queen sized bed, tiled shower and a verdant yard outside your windows. Your...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 2
📍 Koloa, Hawaii

Garden Retreat w/Ground Floor Ease - Kiahuna #2115

Kiahuna Plantation #2115: Tropical décor delights in this 690sf rare deluxe ground-floor suite. You and your friends or family can easily access the grounds from your ground-floor balcony and walk to world-famous Poipu Beach which according to "Travel Channel" was once...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 4
📍 KOLOA, Hawaii

Hawaii Life Rentals Presents Puu Poa 309

Welcome to your dream retreat at Puu Poa 309! This impeccably renovated (completed - 3/1/24) two-bed, two-bath condo has AC throughout and two oversized lanais that have one of the greatest views on Kauai's north shore. The condo combines a harmonious blend of modern...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 4
📍 Princeville, Hawaii

Close to Everything, Stunning Palms at Wailea Condo, Full A/C, Upper Floor

Welcome to Palms at Wailea 2304. Come to Wailea to enjoy the most beautiful beaches and best restaurants Maui has to offer. Get ready to make long-lasting memories while relaxing at this recently updated two-bedroom condo at the beautiful Palms at Wailea. This second...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Kihei, Hawaii

NEW Full Reno 4BD/3B PRINCEVILLE HOME, STEPS FROM QUEEN'S BATH w/ AC & Jacuzzi!

LUXURY PRIVATE 4 bed 3 bath 1760 sf home on a >10K lot w/mtn views in Princeville, a luxury high end community. AC/Jacuzzi/Bikes/Beach Gear included. ***MAJOR RENO NOW DONE!*** ***New photos now up! 5 min. walk to Queen's Bath trailhead (follow safety signs!), ≈15...

🛏 4 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 10
📍 Princeville, Hawaii

❤️PiH❤️ BLUE SUNSET ★ Steps to A-Bay Beach ★ Resort Pool & Waterslide Pass

Brought to you by Paradise in Hawaii Luxury HomesWelcome to Blue Sunset, part of our Hawaiian Luxury Collection. Blue Sunset is in the front row of the Kolea community at the Waikoloa Beach Resort. This gated community is situated on more than 30 acres and boasts...

🛏 3 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 8
📍 Waikoloa, Hawaii

Incredible Highrise Views! | Heart of Town

Enjoy breathtaking ocean views in this recently completely remodeled 1-bedroom hotel condo, perfectly located next to Ala Moana Mall and across from Ala Moana Beach Park. Ideal for up to 4 guests, the condo features two double beds, a functional kitchenette, and a...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 4
📍 Honolulu, Hawaii

Location Location! Ekahi 32C! Designer Remodel 2bdrm $400 Remaining SpringSummer

Wailea Ekahi Unit 32C is a beautiful vacation condominium in the prestigious area of Wailea, known as the 'sunny side' of Maui. It is located on the greenbelt, just across from one of Ekahi Village's four private pools and a very short stroll to the beach and pool...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Wailea-Makena, Hawaii

ICC 22 Beautiful 2BD Cottage Perfect Tropical Vacation

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...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 5
📍 Lahaina, Hawaii

Ilikai Hotel Lite #2139: Studio condo with Sunset Ocean View

Ilikai Hotel Lite #2139: Studio condo with Sunset Ocean View and Kitchen, adjacent to Waikiki Beach and Yacht Harbor and just 2 blocks to Hawaii Convention Center and Ala Moana Beach Park.The iconic Ilikai Hotel and Luxury Suites is defined by its bold architecture and...

🛏 2 Bedrooms
🛁 1 Bathroom
👤 Sleeps 4
📍 Honolulu, Hawaii

The Best Ocean View Studio Condo at the Royal Kahana Oceanfront Resort

We finished a complete remodel of the kitchen and the living room in December 2021.Stop!! You found it!! The best studio condo at the Royal Kahana based on the view, condition and price. If you've stayed in other studio's at the Royal Kahana it's time you stayed in the...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 2
📍 Kahana, Hawaii

❤️PiH❤️DOLPHIN HALE★Close to Pool and Fitness★Bikes Beach Gear★ Full 3 Bath

Brought to you by Paradise in Hawaii Luxury Homes. What makes a Paradise in Hawaii home stand above the rest? Our homes have adult and kid bikes, tons of beach gear, well equipped kitchens, smart TVs and comfy beds and Fast WiFi with great coverage included!! Welcome to...

🛏 3 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 8
📍 Kamuela, Hawaii

50 steps away from Maui's best beach, furnished with luxury details

Welcome to your perfect getaway in Maui! This exquisite 2-bedroom, 2-bathroom apartment, nestled on the 2nd floor of Pacific Shores complex, elevator-accessible building, offers 745 sqft of living space. Furnished with brand new, high-end items in 2021, this apartment...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Kihei, Hawaii

Beautiful 2-BR Villa at Four Seasons Hualalai

**Please note that the Chairman's Club Event takes place each year at Four Seasons Resort at Hualalai from approx December 2 - December 7th. . This event will result in limited access to resort amenities. Details at end of listing!. **Enjoy the quintessential Hawaiian...

🛏 2 Bedrooms
🛁 1 Bathroom
👤 Sleeps 4
📍 Kailua Kona, Hawaii

Kekela Nui Beachfront - Steps to beach + AC!!

*30-night rental*Are you looking for an affordable beachfront property that will fit the whole family and not break the bank? It is a private beachfront property that your family will enjoy and love. The ocean is just steps away. There are no crowds to fight, no public...

🛏 5 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 20
📍 Laie, Hawaii

New Year's Eve at Hilton Grand Vacation Resort - Kings' Land 12/30/23 - 1/6/24

Hilton Grand Vacation Club - Kings' Land - 2 Bedroom Plus Unit (2KP) - 1269 Sq Ft, Sleeps 6 (second level) - RESERVATION IS FROM SATURDAY to SATURDAYLocated on the Kohala Coast, Kings’ Land is a Hilton Grand Vacations Club resort on 112 ares with world-class amenities...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Waikoloa, Hawaii

Maui's Ultimate Luxury Estate – Ka'anapali Beachfront Paradise

Boasting an epic location on one of only 6 beachfront residential parcels in all of Kaanapali, this breathtaking 9BR/9.5BA estate represents the pinnacle of Maui vacationing. Guests will enjoy the space and solitude of this luxurious private home nestled steps from...

🛏 9 Bedrooms
🛁 9 Bathrooms
👤 Sleeps 22
📍 Lahaina, Hawaii

Kukuiula Cottage #27 By Parrish Kauai

This handsomely designed and decorated Kauai cottage offers the details of early plantation days yet with the modern conveniences of central air conditioning, as well as everything else one needs to indulge themselves on a luxury Kauai vacation. Enjoy the lush garden...

🛏 3 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 6
📍 Koloa, Hawaii

Ocean front 1 Bedroom condo in desired F building in Papakea Resort in Maui HI

No resort fees!! Papakea is an unique property. Instead of a high rise it is a set of buildings only 4 levels high. There are three sets of buildings that front the ocean and we are located in the middle section--the perfect location for reaching either of the two...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 4
📍 Lahaina, Hawaii

Luxury Poolside Villa | Stunning Ocean View, Lanai

Summary:D210 | TA-019-101-6960-01Enjoy tropical views and elevated comfort at Villa D210, part of the Poolside Villas at Poipu Kai. This spacious 3-bedroom retreat features an open layout, designer furnishings, central A/C, and a fully equipped gourmet kitchen. Dine...

🛏 3 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 6
📍 Koloa, Hawaii

Jaw Dropping Ocean Views from Second Story, 2 Bedroom Unit 2D

As you wake up in the morning, take in the beautiful view with the cool ocean breeze. Sit on the balcony with a refreshing drink as you appreciate the magical Maui sunsets. Vaulted ceilings. Granite countertops. Spacious bathrooms. Open concept. Large glass sliding...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 4
📍 Kihei, Hawaii

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