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.
Kuleana Club #615 Oceanfront - 1 bd&1 ba - Gated
Summary:Located on Maui's tropical west coast, the Kuleana Club has a panoramic view of the Pacific and the lovely offshore islands of Molokai and Lanai. This unit is a 2nd floor oceanfront condo, only steps to the ocean, and surrounded by a plush Hawaiian garden. Enjoy...
Anini Vista Viila at Princeville Resort By Parrish Kauai
Perched above the turquoise waters of Anini Reef and the lush fairways of the Prince Golf Course, Anini Vista Villa is a contemporary luxury retreat in the prestigious Queen Emma’s Bluffs neighborhood of Princeville. This luxe four all bedroom suite home offers nearly...
Beach escape NorthShore 1BR Unit OceanView
NOTE: There's ongoing(as of November 2021) building construction that may cause noise and some areas closed during your stay. Working hours between 9am-2:30PM(Mon-Fri).This is a beautiful area of Oahu, which takes you away from the crowds of town yet you are close to...
Kapalua Bay Villas | 2 Free Rental Cars | KBM Resorts | Whale Watching | 2 Units, 3 Bedrooms | KBV ML-2023
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
Hawaiian King 212 Studio Suite, Full Kitchen, Pool, Sleeps 2
Welcome to Hawaiian King 212 Suite - Your Home in the Heart of Waikiki!Address: 417 Nohonani St #212, Honolulu, HI 96815Room Type: 1 bedroom Hawaiian King 212 Suite Overview: Discover your own slice of paradise in the heart of Waikiki with our Hawaiian King 212 Suite....
NEW! Tropical Hideaway by Keauhou Bay | Golf, Beaches & Views
Keauhou Palena – Kailua-Kona Vacation Rental CondoDiscover Your Perfect Hawaiian EscapeNestled between the scenic Keauhou Bay and the Kona Country Club Golf Course, Keauhou Palena is a peaceful, secluded condo village where you can park right at your own front door....
Tropical 2BR Ocean View Retreat – Marriott Kauai Beach Club
Experience island serenity in this 2 Bedroom Ocean View Villa at Marriott’s Kauai Beach Club, nestled on the golden sands of Kalapaki Beach and surrounded by lush tropical gardens. Located just minutes from Lihue Airport, this resort combines oceanfront beauty,...
Makani A Kai B5 Ocean Front condo 10 yards from private beach access.
Oceanfront Escape at Makani A Kai B5 – Maalaea, MauiWelcome to your personal paradise on Maui’s southern coast! Nestled directly on the beach in Maalaea, this 2-bedroom, 2-bathroom oceanfront condo offers the ultimate island retreat. With sweeping views of the...
Honua Kai | 3 Free Rental Cars | KBM Resorts | Amazing | 3 Units, 5 Bedrooms | HK ML-1784
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
Kaanapali Alii | 235
Welcome to Kaanapali Alii 235, your perfect luxury vacation rental nestled in the heart of Maui's Kaanapali. This stunning two-bedroom, two-bathroom condo offers an unparalleled oceanfront experience, making it an ideal short-term rental for families and couples seeking...
1 Bedroom Ocean View - Silver
Welcome to the serene and luxurious Mauna Lani Point B102, your perfect retreat nestled in the heart of Kamuela. This stunning 1-bedroom, 1-full bathroom, and 1-half bathroom condo offers an elegant blend of comfort and style, ideal for a romantic getaway or a peaceful...
Maui Kaanapali Villas #221: Studio garden view at a beach front resort in West M
Maui Ka’anapali Villas #221: Studio garden view condo at Beach Front Resort on N. Kaanapali BeachThe space: This condominium is located in the Aloha Tower, the central hub of the property. Situated on the second floor, this condo has views of the surrounding foliage....
Most Expensive Luxurious Oceanfront Estate on Makena Beach-6BR/7.5BA 8,030 Sq Ft
Step into island luxury at this breathtaking oceanfront estate on Makena Beach, one of Maui’s most expensive, exclusive and pristine stretches of coastline. With 8,030 square feet of elegantly designed living space, 6 spacious bedrooms, and 7.5 bathrooms, this private...
Beachfront Paradise! Enjoy surf & sunsets on beautiful uncrowded beach. Relax!
Oct/Nov Special $7500 mo. Gorgeous, oceanfront, beachfront home in beautiful Makaha. Great 30 day rental specials. Contact owner for dates, availability and any questions. Spectacular views of beautiful Makaha beach, coastline and mountain range from all major rooms in...
Spacious Hillside Villas 1500-7 by Gather w/AC, Lanai, Pool Access & Golf Ne
Hillside Villas 1500-7 welcomes you to the relaxed elegance of Ko Olina in Kapolei. This spacious two-story villa offers three bedrooms, two and a half baths, and 1,553 square feet of thoughtfully designed living space. With peaceful garden and golf course views, it’s...
Kapalua Bay Villa 19B2 Gold Oceanfront 2 Bedroom
- Villa closest to Oneloa Beach- 1st floor villa with 16 stairs between parking and front door- Travertine tile floors throughout- Updated open kitchen with granite counters and all the expected appliances, including: fridge with ice maker, stove/oven, microwave,...
Luxury, Comfort and Aloha Spirit Await on the Big Island
Welcome to the ultimate Hawaiian escape at Na Hale O Keauhou, where the gentle ocean breezes, swaying palms, and stunning sunsets create the backdrop for an unforgettable vacation. This enticing two-story condo, available for vacation rental by owner (VRBO), offers the...
Stunning Hawaiian Vacation: 2 Bedroom at WorldMark Kona
Spread out with the whole family in this spacious two-bedroom suite. Bed sizes may vary in bedrooms.Located in the area regarded by King Kamehameha as one of the most beautiful spots on the Big Island, this resort is an ideal destination for your...
Kailani Vista - 3-Story Oceanfront Home w/ Hot Tub, Elevator & Putting Green
Kailani Vista is a private, 3-story oceanfront haven perched directly on iconic Ali‘i Drive, a leisurely stroll from downtown Kailua Kona. Spend your days exploring lava-rock tide pools at your doorstep, perfecting your short game on the backyard putting green, or...
Oceanfront Resort-Beach Access, Close to Oahu's Popular Sites
This delightful two-bedroom provides the perfect respite for the whole family.Ocean View Two Bedroom Villa, 2 King, Sofa beds: 2, Bathrooms: 2, Full kitchen, Microwave, 1280sqft/115sqm, Living/sitting area, Dining area, Separate dining room, Separate living room,...
Garden Setting Close to Beach with A/C Central Location Maui Vista 1BR/1BA
Escape to this fabulous condo in picturesque Kihei. Secluded, quiet, ground floor unit with garden view. 5-minute walk, (0.3 mile) to Charley Young Beach. Perfect retreat for an individual or couple. Fully equipped NEW kitchen, split A/C, large lanai, in-unit laundry,...
Kaanapali Alii 444
Welcome to Kaanapali Alii 444, a luxurious vacation rental nestled in Maui's exclusive Kaanapali Alii Resort. This stunning condominium offers a breathtaking view of the Pacific Ocean, surrounded by swaying palm trees and the meticulously maintained grounds of...
Cozy Ocean Stay 2BR unit
Escape the bustle of Waikiki and access some of the North Shore’s best beaches! You’ll be in proximity to Ahupuaʻa ʻO Kahana State Park, Turtle Bay, the Maʻakua Ridge Trail and World Famous Banzai Pipeline where you can catch a wave or watch pro surfers in...
Aloha Surf Waikiki: Pool & Beach Access
Aqua Aloha Surf Waikiki 504: Studio Deluxe room with Lanai and Partial City Views located just 2 Blocks to Waikiki Beach. A surfer’s lifestyle is all about being inspired by the ocean, hitting the beach for sun therapy, and laid-back living with aloha. (1) Full bed,...
Honeyed Jade: 8 BD Ultra Luxury Oceanfront Diamond Head Estate with Pool & Hot Tub
Honeyed Jade is an enchanting Diamond Head vacation rental estate located on the exquisite island of Oahu. Oahu is an ideal island to visit if you envision yourself amid beautiful Pacific blue waters and within easy access to shopping and first-class restaurants....
Welcome to Windsor Waikiki #3804! A Beautiful Vacation Rental.
The perfect getaway, high above world-famous Waikiki Beach! The Windsor unit 3804 has Limitless views of the sparkling ocean, the Ala Wai marina, Ala Moana Park, and the twinkling lights of downtown Honolulu. Whether it's a romantic interlude or chance to work remotely...
Sea Glass: Luxurious 3BR in Princeville w/ Lanais, Pool Access & Mountain Views
Welcome to Sea Glass by Gather, a pristine residence nestled within the premier gated community of the Villas of Kamali’i, just steps from the Princeville Makai golf course in Princeville, HI. This stunning three-bedroom, three-bathroom home, recently renovated from...
Honua Kai | 3 Free Rental Cars | KBM Resorts | Studio Value Price | 3 Units, 5 Bedrooms | HK ML-1321
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
Royal Kahana Maui 519 Ocean View Studio
- 5th floor condo with balcony on the south side of the building- Updated kitchen with granite counters includes stove, oven, stainless steel refrigerator, microwave, coffeemaker, toaster, coffee starter kit, blender, tea kettle and complimentary tea- Updated bathroom...
Honua Kai | 2 Free Rental Cars | KBM Resorts | Extra-large Corner Suite | 2 Units, 3 Bedrooms | HK ML-1430
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
Kiahuna Plantation Resort 403 Garden View 1 BD
Surrounded by tropical greenery, this one-bedroom cottage-style condo offers peaceful garden views and island comfort. Just steps from Kauai’s most famous beach, it’s the perfect retreat to relax and recharge. Unit 403 Garden View 1 Bedroom 1 Bath• First floor...
Maui Resort Rentals: The Whaler 520 - 5th Floor 1BR w/ Partial Ocean Views!
This suite is the ideal retreat for your next Maui getaway. With over 900 sq ft of interior living space and over 200 sq ft of lanai space, your party will have plenty of room to relax, gather, and reconnect.Located on the 5th floor with a north-facing orientation, the...
New listing: Oceanfront Oasis on Maui - Ocean View Aston Kaanapali Shores 606
Welcome to Kaanapali Shores 606 – Your Oceanfront Oasis on MauiNew Listing! This condo was previously managed by the front desk program and just transitioned to private management—so no guest reviews yet, but it’s the same great unit with even better service.Step...
Kaanapali Alii 1102
Welcome to your dream luxury vacation rental at Kaanapali Alii 1102, a stunning oceanfront condo nestled in the heart of Lahaina, Maui. This short-term rental offers a perfect blend of comfort, elegance, and convenience, making it an ideal choice for families and...
Gorgeous 6 bedrooms for 16 Lahaina Maui ocean view penthouse
Gorgeous 6 bedrooms for 16 Lahaina Maui ocean view penthouse! This gorgeous 6 bedrooms 5 baths for 16 is made up of two separate 3 bedroom ocean view penthouses! The complex features 2 pools, cabanas, tennis courts, putting greens, shuffleboard and plenty of gas BBQ's...
Wailea Ekahi Village 6F - 1 Bedroom Garden View Condo
Wailea Ekahi Village 6F is a premier vacation rental located in the heart of Wailea, Maui. This one-bedroom, two-bathroom condo located within the resort community of the Wailea Ekahi Village, a low-density collection of condo clusters set across 34 acres of beautifully...
Cute Loft Studio above Kona, surrounded by Coffee farms
Cute Loft studio in Holualoa, right above Kona. Our 2 acre property is surrounded by Coffee farms. Hike to a famous Kona Coffee farms like : Heavenly Hawaiian and Buddha's Cup. Cooler elevation. Tropical fruits and flowers. Conveniently located close to tourist...
Charming cabin in Pāhoa for a peaceful getaway
Unwind in Pāhoa at this peaceful cabin. With a cozy living room featuring a comfortable queen bed, guests can relax after a day of exploring. The bathroom offers a refreshing rainfall shower and skylight for a wonderful start to the day. Experience what Pāhoa has to...
Pili Mai 13M - Golf Course Villa in Poipu by Coldwell Banker
Pili Mai 13M - Golf Course Villa in PoipuThis beautiful, ground-floor villa in exclusive Pili Mai Resort combines modern luxury with all the conveniences of Poi'pu.Nestled within the exclusive Pili Mai Resort, this lovingly maintained 3-bedroom, 3-bathroom sanctuary...
Royal Kahana Maui 120 Garden View 2 Bedroom 2 Bath
- Tile flooring throughout and vinyl plank flooring in each bedroom- Open kitchen with– fridge, stove/oven, microwave, cookware, tableware- Both bathrooms have a walk-in shower- 1 king bed, 1 queen bed and 1 queen sofa bed- 1,141 sqft/106 sqm- 1st floor condo with...
Amazing views! Exclusive & peaceful Hawaii Kai. Walk to ocean & hikes, Pool, AC,
A pristine, quiet neighborhood on the backside of Hanauma Bay, your Honolulu/Oahu adventure begins at this lovely 4-bedroom house. With 2 king beds, 1 full bed, and 1 queen bed, this newly rebuilt property is perfect for families or small groups of friends. Three of the...
Deluxe Garden View w/WiFi & A/C-Maui Banyan
Maui Banyan T108A: Tasteful artwork, chic floral patterns, and rustic island color tones set the mood in this wide-open 1st-floor unit that boasts sleek hardwood flooring and oversized garden-facing windows. The functional layout is furnished with premium furniture that...
Hale Nalu (Lower Level) by Gather: Oceanfront w/ Lanai, Grill & Views
At Hale Nalu (Lower Level), the Pacific Ocean stretches out from your backyard while the famous beaches of O'ahu’s North Shore frame your days. This three-bedroom, two-bath home offers relaxed beachfront living with its own full kitchen, living spaces, and covered...
Peaceful Ground Floor Unit- Hale Kaileia Kai with Infinite Pool & Hot tub
Welcome to your serene island hideaway at Fairway Villas #C2, in the beautiful Wāikoloa Beach Resort on the Kohala Coast. This spacious 2-bed, 2-bath ground-floor villa (1,170 SF) blends modern comfort with relaxed resort living. Enjoy golf course + Mauna Kea views...
KBM Resorts: Napili Point, NAP-B26, 1 Bedroom Condo w/ luxury amenities, Includes Free Rental Car!
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
Live Local Redwood Pole house panaramic Ocean views quiet convienent nbrhood
. Wailupe is on mountain side , 5 blocks facing ocean. enjoy tennis, bball/park across street, great views. Convenient location to town, Waikiki 4 miles away. Two bedrooms in large great room. Main bedroom has a queen size bed, sons room has a twin, and living room has...
2 Bedroom Premier (2BX) at Grand Waikikian, a Hilton Grand Vacations Club
Step into the tropical oasis of The Grand Waikikian by Hilton Grand Vacations Club and prepare for the Hawaiian vacation of a lifetime! Nestled within the renowned Hilton Hawaiian Village® Waikiki Beach Resort, this upscale resort offers a perfect blend of island...
Maui Resort Rentals: Honua Kai – 4 Total Bedrooms + Den w/ Beautiful Ocean & Mountain Views!
Unquestionably one of Honua Kai’s best values, this exceptional 4BR plus den offering combines two neighboring partial oceanview suites with an adjacent mountain view suite. Together, the residences provide the perfect retreat for large groups or families seeking a...
Kaanapali Alii 464
Welcome to Kaanapali Alii 464, a luxurious vacation rental nestled in Maui's exclusive Kaanapali Alii Resort. This deluxe condominium offers breathtaking views of the Pacific Ocean, surrounded by palm trees and the resort's manicured grounds. Immerse yourself in the...