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.
New May Specials, 5 Star Reviews! F403 Top Floor 2 BR/3 BA
Welcome to the Waipouli Beach Resort and Spa! The premier resort on Kauai!Waipouli Beach Resort and Spa is located beach front on the Coconut Coast between the historic towns of Kapaa and Wailua. Located convenient to both Princeville on the north and Poipu Beach on the...
Experience Paradise At Our Modern Hawaiian Cottage With Ocean Across The Street
Experience paradise living at "Surf Temple," a stunning Hawaiian Cottage with a perfect blend of modern decor and traditional charm. With lava rock walls gracing both the house and property, every corner of this place embodies the essence of Hawaiian culture and spirit....
S&N Lux suite/Free Parking/King Bed/Kitchen/Wi-Fi
Experience luxury in our modern suite in Honolulu, Hawaii. Nestled amidst European-style gardens, our resort harmonizes with Oahu's tropical charm. Relax in the outdoor pool, stroll through the garden, stay fit in our gym, or unwind in the sauna. Explore Honolulu's...
Hawaii Oceanfront 1-bedroom Cottage
Throw a pebble into the Pacific Ocean from your lanai. Hale Aloha is a detached, very private, oceanfront guest house located in the magical neighborhood of Puako, next to Mauna Lani Resort on the Big Island of Hawaii. Ocean breezes and ceiling fans keep the home...
Beachfront 2 Bedroom / 2 Bathroom Condo in Kihei
Indulge in luxurious island living at this oceanfront 2-bedroom, 2-bath condo in Kihei, Hawaii! This well-appointed condo is located directly on Keawakapu Beach, so you can spend your days splashing and snorkeling under the sun. Explore the excitement of the area at top...
Breathtaking penthouse ocean view in South Kihei
Menehune Shores is an oceanfront complex located in North Kihei, which is ideal for families and couples that don’t like rain, love beautiful sandy beaches excellent for swimming, snorkeling, sunset watching and enjoyable relaxed condo living! Truly oceanfront, there...
Hihimanu House by Gather: Spacious Home w/ Lanai, Mountain Views & A/C
Welcome to the Hihimanu House by GatherNestled in the heart of Princeville, Hawaii, Hihimanu House is a serene oasis of modern luxury and island ambiance. Newly remodeled, this 2,499-square-foot single-family home offers 4 bedrooms and 3.5 bathrooms, seamlessly blending...
Newly renovated, Free Parking, One block to Waikiki Beach
See my other Properties # 1503692 and #3156864 and #3512192 for my 5-STAR reviews and to book multiple units in the same building.Located in the Waikiki Sunset with beautiful mountain and city views this condo offers enough beds to sleeps 6. 1 bedroom (king bed and twin...
Oceanfront Views * 3 Bedrooms With Baths * All Remodeled * Fabulous Beaches !
This entirely renovated private oceanfront view retreat on the North Shore of Kauai in Wainiha on the edge of Hanalei is perfect for short- or long-term getaways for family or friends seeking luxurious accommodations with breathtaking views. Discover the relaxing...
*Hono Kai A11* Maui condo steps to the sand!
In the beautiful ground floor Hono Kai A11 garden-view unit, you will be immersed in rich tropical foliage from your spacious private lanai only steps from the complex beach access! Remodeled and decorated with the spirit of Aloha, this unit features a primary bedroom...
Luxurious 3BR Fairways at Ko Olina 20G with Golf Views
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 Fairways at Ko Olina 20G by Gather,...
4 bedroom beach home with added sofa bed, ocean view, swimming pool, Jacuzzi
Hale Lanui is located across the street from the ocean and has sweeping unobstructed views of the ocean and sunsets. This two story 2700 SF home is located on a residential street and has a swimming pool (lots of beach towels) and Jacuzzi for total enjoyment. There are...
Maui Resort Rentals: Hokulani 4 Total Bedrooms, Stunning Partial Ocean & Mountain Views + XL Lanai!
This exceptional pairing combines a partial oceanview 2BR suite with an adjacent 2BR mountain view suite to create a four-bedroom offering featuring gorgeous views of the Pacific Ocean and the awe-inspiring West Maui Mountains. Together the neighboring suites boast over...
Watermark - Luxury 2BD/2BA/1PA on 22nd floor with an Ocean View!
This unit has 1 queen size bed, 2 twin size beds, and 1 sofa bed, and can accommodate maximum of 5 people. This picture-perfect luxurious unit has 2 bedroom/2 bathroom/1 parking. From the bedroom, you are able to see the brilliant view of Ala Moana Beach from a window...
++BEACHFRONT RESORT+OCEAN VIEW STUDIO A-317+CENTRAL A/C+FULLY EQUIPEPPED++
Ka’anapali's finest beachfront setting, 1/2 mile north of Black Rock. A prime location near shopping, restaurants, and activities. Our studio condo, A-317, is located on the third floor of the Aloha Tower and offers a lovely partial ocean view. It is accessible by...
Beautiful Oceanfront Condo with Stunning Views in the Heart of Maui!
***Professionally Cleaned Condo, No-Contact Check-In/Check Out*** Welcome to your perfect slice of paradise in this stunning oceanfront condo in the heart of Maui. This condo is located on the top floor of the complex, offering breathtaking panoramic views of South...
Maui Eldorado Bargain Bargain Bargain - Book Now Ka'anapali Whalers Village K110
Note: Maui Eldorado resort charges a one time $60 resort fee and $20 per day fee at check in. Beautiful Ka'anapali beach resort and Whalers Village is an easy walk from # K110. Located on ground floor our Studio unit sleeps 3 comfortably. Gorgeous fully equipped kitchen...
Where Happiness Lives!
The Grand Champions Villas are nestled in a premier location of Wailea, Maui and provide the experience you would expect from a world-class resort. This quiet, well-managed property features two pools, two whirlpool spas, with barbecue facilities surrounded by lush...
Coastal Paradise 🏝️ Private 3 Bedroom - AC, Pool, Spa, Beach, WFH
Your private paradise awaits just steps away from Kahana beach. This newly remodeled 3 bedroom townhouse was designed by us with laidback, rustic accents and clean, thoughtful designs to welcome you to your luxury coastal stay.The spaceAll bedrooms feature exposed...
Another Day in Paradise with Spectacular Oceanfront View of Kailua Bay
Probably one of the finest direct ocean views in all of Kailua-Kona. This 3rd floor unit looks straight over the ocean and Kailua Bay. Watch the whales breeching and the Spinner dolphins spin. Enjoy your favorite beverage on the lanai while watching spectacular sunsets....
ONE BEDROOM OCEAN VIEW
Welcome to Kihei Akahi! This wonderful 1 bed /1 bath is the perfect location for your Maui vacation. Step cross the street and enjoy Kamaole Beach 2, one of Maui's best swimming beaches. The condo has a fully equipped kitchen, making it ideal to enjoy dinners at home...
Mauna Lani Point | J102
Welcome to Mauna Lani Point J102, a spacious 1,306-square-foot two-bedroom, two-bath condo that offers a perfect blend of luxury and tranquility. This recently updated ground-floor vacation rental features an open floor plan with island-inspired décor and modern...
Poipu Kapili 22 - Ocean Views * Deluxe Furnishings * Central Air Conditioned
Oversized 1 bedroom / 2 full bathrooms; ocean views from premium 2nd floor location Spectacular views and deluxe furnishings will make Poipu Kapili #22 your home away from home. This spacious and comfortable home has an air conditioned master suite and living room....
Your home in the islands!
Another unit we'd love to share with you! Ground floor unit just steps from the beautiful Wailua Bay. Ask anyone, Lae nani is the premier resort of the Coconut Coast; your vacation is sure to exceed your expectations. Enjoy a cup of Kauai's famous coffee while watching...
Luxurious Blue Horizon Villa near Hilo, entire villa
Welcome to the Blue Horizon. Our luxurious, modern villa with hot tub by the cliff is a perfect place for a family vacation for up to 6 people, 2 story approx 2300sf + 1000sf of view lanais. Downstairs has 2 bedrooms with king beds and 2 bath. Upstairs has a very open...
***SPRING SPECIAL*** Kulalani Complex: Experience Hawaiian Luxury, Stunning 2-Bedroom Townhouse
Escape to this luxury two-bedroom townhome in Kulalani at Mauna Lani Resort on the Kohala Coast of the Big Island, Hawaiʻi. This spacious and stylish retreat combines resort-style amenities with the privacy of a gated community.Highlights-Mauna Lani Beach Club Pass –...
Rare Princeville Views! Mountains, Waterfalls, Hot Tub, A/C, Amenities
Wake up to fabulous mountain and cascading waterfall views from multiple lanais! This is one of very few units in Princeville with these views.Makana Breeze is a luxury 2-level townhome featuring 3 bedrooms, including 2 spacious Masters w/ large recently remodeled...
Oceanview House near Best Beaches on Big Island, Massage Chair!
This house, called Hale ‘Uhane, (House of the Higher Self), is located in beautiful Kawaihae Village, near Hapuna Beach. The 3-bedroom hale boasts a very short drive to a variety of world famous and award-winning beaches. Along with the best beaches in Hawaii, there...
Visit Enchanting Nanea! April 19-26, 2025
Welcome to beautiful Maui! Stroll the white sand Ka’anapali Beach, sharing sunsets with the isles of Lana’i and Moloka’i. Dine in the finest restaurants or grill your own fresh fish and steaks near the pool. Ride to the top of massive Haleakala volcano, or take...
Makena Surf C-107: Premier Luxury Condo • Local Art • 2 New Pools • Pickleball
Located in a hotel-zoned area, our condo wouldn't be affected by Bill 9 if it passes. Vacation rentals would remain completely legal here—no worries for your stay!PLEASE NOTE THAT THE SECOND BEDROOM CAN BE CONFIGURED WITH EITHER A KING BED OR 2 XL TWIN BEDSMAKENA SURF...
101 - 2 bed/2 bath with A/C! Ground Floor Oceanfront with Breathtaking Views!
When only the Best will do! * Beautifully remodeled AIR CONDITIONED oceanfront condo! * FREE HI SPEED WIRELESS INTERNET CONNECTION * FREE LONG DISTANCE CALLING TO USA AND CANADA * 100 feet from one of the finest beaches in Maui * Wonderful snorkeling and water sports at...
Jungle Home/AC/ NearHot Ponds Fissure 8/Hot Tub
Right off 130 surrounded by lush jungle. We are ready to help you have the best adventure this side of Hawaii! . 7 person 58 jet Hot tub!! 3BDR/2BA FULL Access. Laundry Rm is SHARED w/ host.Cable High Speed Internet, snacks, avocados on site, AC in living rm . Make your...
Rainbow Hale Estate Ka'anapali - Luxury Oceanview Estate with Pool & Hot Tub
Set on 5.13 acres within the gated Kaanapali Coffee Farms, this single-level estate offers sweeping ocean views, three king suites and a convertible den to accommodate up to 8 guests. The gourmet kitchen features a built-in espresso machine; the saltwater infinity pool,...
Beautiful Oceanfront Ohana: Spectacular Views, Pool, A/C, Best Beach&WOW Sunsets
Aloha and Welcome to our Maui Ohana!Relax and recharge at this tropical retreat, perfectly situated within a short walk to Wailea in the Kihei Surfside Resort. Boasting stunning ocean views, direct access to Maui’s best beach, Keawakapu, and a sprawling lawn with a...
Beautiful Ocean Views 5 Bedroom Sleeps 14 Walk to Beach, Pool, AC, & Game room
The "Akai Beach House" is a beautiful 5 bedroom 4 bath home that sleeps 14 with ocean views, a pool, air conditioning and a large game room in the garage. Enjoy ping pong and foosball, or relax on the couch and watch TV in the game room. Magic Sands Beach - the best...
Kiahuna Plantation Resort 203 Ocean View 2 BD 2 BA
- Two story condo with beds and baths downstairs and living areas upstairs looking out to the ocean- Walk-up, no elevators- Bright and airy with tropical accents- Wood floors upstairs, tile downstairs- Full kitchen with granite countertops and backsplash includes full...
The Golden Lotus ~ Pool ~ Jacuzzi ~ Grills ~
A BEAUTIFUL GEM on the North Shore. This LUXURIOUS 2 Bedroom Suite offers HIGH-END COMFORT and Spectacular Ocean Vista, Jungle Valley & Mountain Waterfall Views. Enjoy the Sunsets on the Furnished Balcony. Ceiling Fans in every room - NO AIR CONDITIONING Ideal for...
NEW! Fully Renovated 1BR/1BA condo. Short walk to beach & Coconut Marketplace!
Welcome to your slice of paradise on Kauai’s beautiful Coconut Coast. This newly renovated 1-bedroom, 1-bathroom corner unit at Plantation Hale Suites is located on the ground floor for easy access and offers the perfect blend of comfort, convenience, and island...
Kona Sea Ridge#Y22: Beautiful Top Floor unit with Ocean Views in Gated area
.Oceanview Paradise | Top-Floor 2BR/2BA Kona Sea Ridge Condo | Kailua-Kona, HawaiiWelcome to your slice of paradise at Kona Sea Ridge! This top-floor, two-bedroom, two-bath condominium offers beautiful ocean views and the perfect blend of island comfort and modern...
Ocean view Waikiki suite! Free parking, full kitchen, pool, close to beach!
Waikiki Banyan #3508-T1 – 201 Ohua Ave.NEW TO OUR INVENTORY! Enjoy your perfect Hawaiian getaway in this fully-furnished 1-bedroom/1-bath ocean view suite in the heart of Waikiki! 533 square-feet of interior living space, plus a private lanai with gorgeous views of...
Ocean view, fully remodeled, 2nd floor, few steps away from the best beaches
**Welcome to Your Perfect Maui Getaway!**Nestled on the second floor with breathtaking views, our recently remodeled rental unit offers a seamless blend of modern comfort and coastal tranquility. Enjoy stunning vistas from the lanai, overlooking a beautiful green belt...
Kolea 3B - Special Rates Plus Lava Lava Beach Club!!
Kolea 3B Special Rate $550/nt+tax Plus $100 Lava Lava Beach Club for a limited time!3 bedroom, 3.5 bath2nd floor level with semi private elevatorPartial ocean and mountain viewsMaster suite king bed with private lanai, ensuite with dual walk in shower, deep soaking tub,...
Kaanapali Alii | 143
Welcome to Kaanapali Alii 143, a stunning two-bedroom plus den residence designed for ultimate comfort and style in the heart of Maui. This spacious retreat offers ample room for your entire group, making it the perfect getaway. The den can be fully enclosed, providing...
Mokulua Sunrise Ocean Villa Lanikai
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.Enjoy top-tier luxurious living on your next...
Kimo's Getaway
This a very private duplex. Your host lives upstairs. Your's is a new two bedroom, one bath unit, with a full sized kitchen and adjoining dining area. . There is a large lanai viewing the ocean with plenty of relaxing chairs and an outside dining area.You will be a 7...
$150 off the normal nightly rate ($825) for May 22nd to July 20th dates
Cozy coastal sanctuary steps from Waialea Bay. Tucked into lush tropical landscaping, Honu is a beautifully simple, single‑story retreat designed for serene beach‑side living. The home features a central living and dining area adjacent to a recently updated kitchen,...
LUXURIOUS OCEAN VIEW CORNER UNIT W/ ALL AMENITIES
You will love our condo that is located at The Whaler with one of the best locations on Kaanapali Beach. We are located right on the beach and a few steps away from Whalers Village. VRBO walking map is incorrect. I think it is about 30 steps from our building to the...
15 Steps to the Beach! Ground Floor Completely Renovated on the North Shore
Brand new rental on the North Shore, 15 steps from the beach! This property was 100% renovated in January 2023 and everything is in *MINT* condition. Everything is brand new. You're going to love the tasteful decor, the incredibly comfortable beds and sheets, the...
Hale Joli: Historic Typical Hawaiian Home w/Ocean Views, Lanai & BBQ Area
Welcome to Hale Joli by Gather, a serene retreat that captures the essence of old Hawaii while providing all the modern amenities you desire. This unique three-bedroom, two-and-a-half-bathroom ranch home is a tranquil oasis nestled on a private road, offering you a...
Anini Vista Drive Estate - Kauai North Shore Gem
A grand estate centered on a magnificent lagoon-style saltwater pool with two waterfalls, a grotto, hot tub and bridge, Anini Vista Drive Estate is a paradise in its own right. Inviting ocean views and expansive gardens surround the main house and guesthouse, which are...