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.
4 Bdrm Luxury Golf Course Home with A/C
Welcome to Molokama. Walking distance to a white sand beach through Hanalei Bay Resort in Princeville, Kauai. The home overlooks the Robert Trent Jones designed Makai Golf Course. The 4-bed, 3-bath home sleeps 8 comfortably. 4 bikes, beach gear, outdoor shower. Master...
E Komo Mai at Princeville Pool House!
This charming two bedroom (king, queen) plus den (queen sofa sleeper) home is set in a quiet section of beautiful Princeville Resort. The comfortably furnished living area has open beam ceilings, artful skylights to let in the warm Kauai sun and koa wood framed slider...
25% discount now to mid July. Fab Kihei Condo-Across from beach, A/C, Pickleball
Our unit is in Building 9. As we vacation often in our condo, we have furnished it to represent our home away from home. Central air has been installed with units in the living room and both bedrooms. Each room can be controlled to enjoy wonderful, noiseless air...
🏖️AC Included | Gated Community | Pool & Ocean Views | vrKCV
vrKCV - Kamilo Place, Professionally Managed by Kona Coast Vacations Private 4-Bedroom Retreat with Ocean Views, Pool & AC in Gated CommunityEscape to your own island oasis in this luxurious 4-bedroom, 3.5-bathroom vacation home located in the prestigious gated...
Waikoloa Beach Villas O2 - Ground Floor Villa 7th Night Free April-June 2025!
Come enjoy the beauty of Hawaii in our perfectly located condo at Waikoloa Beach Villas. Just 20 minutes north of the Kona airport you will find yourself in paradise! Just added - Discounted GOLD GOLF KINGS' CLUB MEMBERSHIP. Book our villa and you will be able to set up...
A True Oceanfront Condo! Freshly Updated! Centrally Located 5 Star Views!
Aloha! Welcome to our freshly updated oceanfront condo located on the "Garden Island" Kauai. - The condo offers stunning views of the culturally significant Wailua Bay and the lush mountain range beyond. My grandparents’ home, the condo was sold, with regret, in 2016,...
Spacious 4BR Princeville Home -AC, SPA, and Bikes for faster beach access
Welcome to Paradise! Great design for family or friend gatherings in spacious two story home. Fast WiFi, and LG 75" inch OLED Smart TV and Outdoor Shower. Enjoy your vacation or workation with family and friends in a tropically landscaped property with Bali Hai...
Pakala Beach Estate: Island-Style Retreat on Kauai's West Shore
Rates shown are for 8 guests; additional guests up to maximum of 11 are $20/night each. This magnificent, island-style estate truly exceeds all expectations. Located on secluded Pakala's Beach on Kauai's west side, this totally serene property borders an orchard and is...
OCEANFRONT to Walking Path & Beach TVNC #1287
$325 per night up to 4 guests. $35 per night for each additional guest. Due to oceanfront location, this unit is located within the Tsunami Evacuation Zone. Honu Hale Kai is a warm and casual home base for your family vacation adventure. This home sits upon an...
Kahana Village #7 Beach Front Luxury
Elegant and luxurious describes our 3 bedroom, 2 bath condo with travertine floors, which makes it the perfect beach house. Our updated ground floor unit faces north with a spectacular view of the ocean and the island of Molokai. It's paces from the beach and overlooks...
Island Touches w/Modern Kitchen, Wood Floors, Lanai, Flat Screen, WiFi–Kaha Lani 203
Castle Kaha Lani Resort #203 - This 739 sq. ft. vacation unit looks out over our resort. Unit 203 features relaxing tropical décor along with convenient touches such as a full kitchen with dishwasher, ceiling fans, dining area, flat screen TV, and WiFi. Sleeps 4 in 1...
Tropical Oasis Studio in Ko Olina Beach Resort - 30 Day Rental
**Note: This property cannot be rented for less than 30 consecutive days. Rental prices will not be adjusted based on the number of days the rental is actually used or occupied.**Prime Location!** Nestled within the prestigious Coconut Plantation community of Ko Olina...
North shore Maui B and B room 1.
Holomakai B and B is a vacation rental with three bedrooms for rent individually on Maui’s north shore. Each room is on a separate floor with a private bathroom, ac, tv and Wi-Fi. The rest of the house, the entrance, fully equipped kitchen, living room and spacious...
Stunning High-Floor Unit with Spectacular Ocean, Diamond Head, and Waikiki Views
Welcome to Waikiki Landmark, where paradise meets luxury living. Come stay at this stunning high-floor views of the Ocean, Diamond Head, and Waikiki. This exquisite 2-bedroom, 2-bathroom unit with 1 parking spot embodies the essence of island living. Located at the...
Kaanapali Alii | 383
Welcome to Kaanapali Alii 383, a stunning two-bedroom oceanview condo that serves as the perfect gathering place for your Hawaiian getaway. The extra-wide lanai is a natural focal point, featuring a dining table, a comfortable lounger, two chairs, and a cocktail...
Wailea Ekahi Village | 19B
Wailea Ekahi Village 19B is a two-story, two-bedroom, two-and-a-half-bath townhome that comfortably accommodates up to four guests. This beautifully designed residence features island-inspired décor, creating a cozy and inviting atmosphere perfect for families or...
Spacious1bed Ocean View Pool Beach Access Tennis Pickle Ball Air Conditioning!!
Our spacious 1bed, 1 bath condo is the perfect place to unwind after a long day of adventuring around this beautiful island. Relax on the lanai with a tropical drink in your hand while watching the beautiful sunset.*3 min walk to swimmable beaches & restaurants*10 min...
Luxury Villa at Mauna Kea w/Private Pool, Stunning Coastal Views & AC: Villa 21
This newly renovated four bedroom luxury property, walking distance to the Mauna Kea Beach Hotel, offers the ideal oasis for relaxing and luxuriating in paradise. Unwind on the generous private pool deck and covered lanai and revel in fabulous ocean, coastline, sunset...
The Maui Moon Oceanfront Condo- Perfect for couples!
Voted as one of the top 25 islands in the world 2020 by Travel and Leisure magazine. Maui is truly the garden paradise for your hard earned Hawaiian Vacation. Aloha and welcome to the Maui Moon Condo in the Menehune Shores oceanfront complex in low key Kihei located on...
2BD/2.5BA, Golf View w Pool, Tennis & Gym, Gated Townhome in Waikoloa Colony
Welcome to Our Luxury Townhouse at Waikoloa Colony Villas!Nestled in the heart of the prestigious South Kohala Gold Coast, our townhouse offers a blend of luxury, comfort, and convenience in a prime resort location. Perfectly positioned in the center of Waikoloa Colony...
KPL 19 Stunning West Maui Getaway Close to the Beach Fully Remodeled 2BD Ocean View Condo
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...
Hilton Hawaiian Village Rental
We are please to provide our Suite units by Hilton Grand Vacations. The resort gives guests ideal access to the best stretch of Waikiki's famous white-sand beach and the extensive entertainment, shopping and dining options within the renowned Hilton Hawaiian...
Wonderful executive home steps from a gorgeous beach
The Beach Haven is a beautiful home that can make your vacation very special. Only steps from one of the best beaches in Hawaii, you will feel the ocean breeze surround you. The home is treetop level which provides views of the ocean and of the Koolau mountains. This...
Perfect Kailua Vacation at Ka Hale Lai-House of Serenity-pool and spa.
Perfect Kailua Home on 18,000 square feet of land all your own!! Lots of room to spread out!! We have a gorgeous newly tiled Swimming Pool and spa! You are invited to rest and relax in “Ka Hale Lai” , Kailua’s House of Serenity, 5 minutes to the beach, and a short...
Steps from waves - Ground Floor - Direct Ocean Front condo -full AC & King bed
Our well-appointed, ground floor, completely remodeled condo is waiting to welcome you in to RELAX. The breathtaking ocean view straight out onto the waves will thrill you the moment you enter into our home. "WOW!!" As our guests, we are confident that you will love it...
1 Bedroom Oceanfront #604
Maui Kai #604. One Bedroom- Flat screen TV, King Bed, Queen sofabed; TV in bedroom. | | This is a beautiful one bedroom sixth floor unit, with expansive views of Molokai and Lanai. Decorated luxuriously with beige tile in the entryway, kitchen and bath, a french curve...
KoOlina Beach Club Oceanfront Resort
Please choose a Friday through Sunday check-in for a 7 night stay. Thank you for your interest in booking with Dash Realty Group, Windermere Florida. Dash Realty Group is registered in Florida as a licensed Fla. Seller of Travel Ref. No. ST42435.Rates are set for...
Cottage with Amazing View, Minutes to Dolphin Swimming, Very Private, Affordable
Please check out the main house on the same property for larger groups:vrbo 1542506This cottage is perfect for a couple looking to save money but still have a million dollar view. In Kealakekua Bay, just 3 minutes from some of the best snorkeling and wildlife viewing in...
PRIVATE CORNER UNIT WITH SPECTACULAR OCEAN FRONT VIEWS
Aloha! Come and enjoy Hale Ho’ola. Our “House of Healing”, situated atop a bluff overlooking the beautiful blue Pacific is a corner unit so private, that it feels like you are the only ones there! Surrounded by the beautiful sights and sounds of the ocean along...
Beautiful Kealakekua Home w/ Spectacular Ocean View
Located approximately 10 miles south of Kailua-Kona is your Hawaiian home while visiting visiting us here on the Big Island of Hawaii. Arise in the morning and enjoy a freshly brewed cup of Kona coffee while planning your adventures for the day. You are just minutes...
Hilton Waikoloa Pool Pass thru 2025. Waikoloa Golf Discounts! J2 Waikoloa Beach
This vacation rental is professionally managed by ResorticaHawaiiWaikoloa Beach Villas J2Please scroll down for detailed informationHilton Pool Pass: Valid for stays through December 31, 2025. Maximum 6 persons per pass (children under the age of 5 are not counted...
Ocean View 4-bedroom house with AC, WiFi in welcoming Princeville
About this space:Open & Spacious Tri-level home sleeps 12+ w/4 bedrooms & 3 bathrooms.Perfect for Friends & Family Gatherings!TOP-LEVEL: Master Suite w/180 degrees of Ocean, Mountain & Waterfall View, 2nd bedroom, 2 baths + bonus TV loft area.MIDDLE-LEVEL: Open Concept...
WG 220 - Charming studio in wonderful Honolulu with WiFi and AC - Sleeps 3
Legal Nightly RentalWaikiki Grand Hotel® 220♥Escape to this charming studio in picturesque Honolulu and less than 2 mins walk to Waikiki Beach. This delightful space features a cozy living area with 1 Queen bed and 1 sofa-bed, perfect for a small group of guestsEnjoy...
Mountain View Retreat Unit 1 - highly rated on leading rental sites!
Peaceful rain forest guest house a few miles from Volcano National Park. Mountain View Retreat is located in a lush and relaxing paradise. Enjoy your coffee or tea in the morning on your own private lanai. For larger parties there is another guest house on the same...
Nestle Into Your Private Cottage After a Busy Day. Enjoy the Hottub - Permitted
Maui County Rental permit - STPH 2013/0024TA-091-083-1616-01TMK-270031060000Fabulous views, privacy and quiet were foremost for us in choosing where to build our dream home in Hawaii. We looked for several years before finding this special Maui hilltop location on the...
Sunset Golf Course Views from Lanai with Outdoor Kitchen!
Enjoy all the best that the Big Island has to offer!! Our beautifully Hawaiian furnished home at the Waikoloa Beach Villas - a luxury gated community at the Waikoloa Beach Resort - is conveniently located across the street from the King's Shops and Queen's Marketplace....
KRV 1723 Remodel 3BD Kapalua Villa w Ocean View
FREE daily activities included with your stay value up to $1035! Complimentary admission, every day of your stay*: Lu’au, Golf, Whale Watch (seasonal), Dinner Sunset Sail, Snorkel Sail, Alpaca Farm Tour, Pineapple Farm Tour, and All Day Electric Bike Rental. (W3)*One...
SPECTACULAR OCEANFRONT GEM!
Brand new fully remodeled Lahaina Gem! This stunning 2 bedroom 1 bath condo is where it’s at! Get the feel of old hawaii with a classy modern twist. We also provide snorkeling gear, body boards, beach chairs, beach towels, and new air conditioning. The Condo is ground...
Maui Family Owned & Managed - Wailea Grand Champions Villa
Located on the world-class Wailea Blue Golf Course. Our Wailea Grand Champions condo has been newly redecorated and furnished with decor that depicts the beauty of Hawaii and our rich Hawaiian culture. As a local family who live on island, we are able to actively...
Spectacular Ocean and Golf Course Views ! Luxury Home with Separate Guest House ** 2 Golf Carts**
Spectacular Sweeping Views from this Four Bedroom Luxury Home with Separate Guest House is Paradise Perfected. Located on the #16 Fairway of the Hualalai Golf Course, this luxury home is recently redecorated by Willman Interiors, and boasts beautiful furnishings, an...
Hanalei Bay Resort 4301: Oceanview w/ Lanais & Resort Perks, Pools & Tennis
Welcome to Hanalei Bay Resort 4301 by Gather, a one-bedroom, one-bathroom condo located in the heart of Princeville on Kauai’s North Shore. This serene retreat offers breathtaking views of Hanalei Bay and the surrounding lush green mountains, perfect for couples or...
Koi Palms 1 bedroom Cottage - Great location! 5 Minute Walk to Kailua Beach!
Come and enjoy our island home with us. Koi Palms Cottage is located within our gated property alongside our lovely Koi pond, in the quaint town of Kailua. The owners live on the property in the main house.The cottage is a 600 square foot 1 bedroom unit. The kitchen is...
Alana by the Waves - Oceanfront Home in Napili
Stunning oceanfront private home in Napili, MauiNestled over a secluded bay and surrounded by luscious tropical trees, this stunning oceanfront home offers breathtaking views along with unmatched privacy. Both bedrooms boast oceanfront views, allowing you to drift off...
Comfy Surf Studio 2 Blocks From The Ocean
This comfy and clean Surf Studio is located 2 blocks from the beach and Ali'i drive where all the best attractions are such as tasty restaurants, fun retail shops, bars, coffee and smoothie spots, fresh farmers markets, Magic Sands Beach, and much more. This relaxing...
WOW! "BEST IN CLASS" POSH NEW REMODEL! 2 BR/2 BA-SLEEPS 9 - 6 BEDS-Great Views!
Unit F-202 is the ABSOLUTE NICEST "fully remodeled" CENTRAL AIR CONDITIONED unit at the relaxing Kaanapali Royal condominium resort. ...And reasonably priced !!! This very quiet unit has wonderful Ocean, pool & Hawaiian landscaping views. The "partial ocean view" can be...
Poipu Bay Getaway - Poipu House - Saltwater pool, hot tub, AC!, Walk to Beach and Hyatt!
Spacious 6-Bedroom Villa with Saltwater Pool, Hot Tub & Prime Location. Welcome to Poipu BayGetaway, your ultimate island retreat on Kauai’s sunny South Shore. Just350 yards from the beach and a short walk to the Grand Hyatt Resort, thisluxurious 6-bedroom,...
Maui Budget Condo with Oceanfront Luxury at Papakea
** Please review the note at the bottom of this section for detailed rate information. **For an overview of Papakea Resort check out: https://www.youtube.com/channel/UChREir40cH28E7foXaSMBkAThis Papakea condominium has a commanding ocean view of Molokai and Lanai. You...
Stunning ocean view 2 bedroom • Steps from beach
Enjoy beautiful ocean & sunset views from, Ohana Lani, a 5th floor condo with 1120 sq of living space and a stunning double wide lanai. The condo artfully blends modern amenities and island style. Ideally located in Kihei, the unit is right across the street from the...
Hilton Pool Pass thru June 2025 and Golf Discounts. Waikoloa Colony Villas 1002
This vacation rental is professionally managed by ResorticaHawaiiWaikoloa Colony Villas 1002Please scroll down for detailed information.Bedding Configuration:Master Bedroom: King BedGuest Bedroom: King BedGuest Bedroom:Queen BedAdditional Bedding: Sleeper Sofa in Living...
Ko Olina Beach Villas O1402: Spectacular 14th Floor Penthouse w/Ocean Views
Welcome to Ko Olina Beach Villas O1402 by Gather, a stunning penthouse on the 14th floor where luxury meets comfort in a tropical paradise. This three-bedroom, two-and-a-half-bathroom penthouse villa accommodates up to six guests.As you enter, the peaceful Pacific...