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.
Kona Sunset View Getaway
Welcome to our dreamy Kona getaway! This newly refurbished, luxury retreat is designed for relaxation in the heart of Kailua Kona. Perfect for group or family trips. Walking distance from Kona's best restaurants and incredible sunset views. It provides easy access to...
CW Royal Garden Waikiki | 1BR/1BA King Balcony Studio
Summary:CW Royal Garden Waikiki | 1BR/1BA King Balcony Studio• Size: 711 - 881• Kitchen: Partial• Baths: 1• Accommodates: 4 Guests• Beds: King Bed - 1 Queen Sleeper Sofa - 1Room Amenities• Hairdryer• In Room Safe• Washer/Dryer In Unit• Broadband...
Tropical Retreat w/ Outdoor Pool, Free Parking, Steps from Papaloa Beach!
Step into a world of relaxation, surrounded by swaying palm trees and vibrant hibiscus blooms. Your spacious suite features a full kitchen, separate living room, and private lanai. Refresh yourself in our sparkling outdoor pools, perfect for relaxation or family fun....
Beautifully remodeled Lanikai house,spacious inside alot of green space outside
In the quaint exclusive neighborhood of Lanikai, our quiet place sets back off the road. It’s a beautifully remodeled house. Beautiful Lanikai Beachhouse newly remodeled December 2022. Rarely available. New fresh paint, new floors, new beds, new mattress, new kitchen...
Hale Kaimana Breeze by Gather: 3BR Oceanfront Escape w/ Stunning Views
Property is currently for sale. The property manager will contact you to make arrangements to schedule showings at a convenient time. This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies...
153-1 Relaxing Puamana 2BR + Loft | Steps to Shoreline
Welcome to Puamana 153-1, a two-bedroom + loft townhome in the tranquil, gated Puamana community just south of Lahaina. Set on 30 private oceanfront acres, Puamana offers a peaceful alternative to high-rise resorts—just steps from the shoreline and perfectly located...
COMPLETELY REMODELED-BREATHTAKING OCEAN VIEWS & SUNSETS-LUXURY FINISHES-AC
Book With Confidence, This Stunning, Newly Remodeled 1 Bedroom, 1 Bathroom Condo At Kamaole Beach Royale. 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...
Island Colony 1-Bedroom Suite with full Kitchen and City View
Waikiki Serenity in the Heart of Honolulu at Island Colony Apartment 1520Welcome to your tropical retreat at Island Colony Apartment 1520, a 1-bedroom suite with a full kitchen and city view. Located in the heart of Waikiki at 445 Seaside Ave #1520, Honolulu, HI 96815,...
Hale Malie – South Kauai Villa with Ocean Views
*Please note that this private home requires a minimum stay of 30 nights for bookings online. If you are interested in a shorter stay, please call our reservations team to discuss options.Feel a sense of serenity wash over you the moment you step inside your Hale Malie...
Hainoa Villa 2903B
Extensively renovated, this contemporary 2 bedroom, 2 bath single-level upper corner floor villa is the perfect blend of luxury and sweeping ocean views. A spacious primary suite also features majestic ocean views overlooking the entire resort and is complete with a...
Papakea Resort - Beautiful Ocean Views! 1 BR w/AC
Enjoy stunning sunsets and whale watching at this centrally-located condo. Centrally located in West Maui, this beautiful condo is ocean front! The living room includes a queen sleeper sofa, with a king bed in the cozy bedroom. Located close to world-class beaches,...
Waiulu Villa at Hualalai Resort: Modern 3BR Villa w/ Lanai, Golf Carts & Pool Ac
September 15 – Mid-November, 2025The Hualalai Resort Spa will be undergoing enhancements to the outdoor aqua-thermal areas of both the men’s and women’s locker rooms. During this time, massage, body, and facial treatments will be temporarily relocated to the...
Honua Kai Konea 701 Ocean View Penthouse 3 Bedroom
Konea 701 Piilani Penthouse Suite 3 Bedroom- Exclusive on-site provider with the only homes meeting the prestigious AAA 4-Diamond designation - 1 king bed in Master Bedroom - 1 king bed in Second Bedroom - 1 queen bed and bunk bed in third bedroom - 2,300 Sq. Ft.- -...
Marriott Ko Olina Beach Club Ocean Front resort 2 Bedroom Villa.
Great for families! Enjoy a luxurious stay for a fraction of the cost. All of our units are managed and maintained by the resort. Upon arrival, guests will check-in at the resort’s front desk using their resort confirmation # just as if they had booked directly...
Kaanapali Alii | 485
Because Kaanapali Alii 485 is a corner unit, half of the walls that make up the living room, kitchen, and dining room are covered with floor-to-ceiling windows or transparent sliding doors. Enjoy constant views of the West Maui Mountains, manicured Kaanapali golf...
Stylish Apt with Amazing Views
Kick back and relax in the calm, stylish space. The Aloha Vibes apt was created to recharge your energy from the outside world. The perfect set up for remote workers or vacationers. Start your day sipping your coffee and watching the sunrise and gorgeous view from the...
Gorgeous 3-Bedroom Condo in Ma'alaea With Extra Large Waterfront Lanai
A true hidden Maui gem! Discover the beauty of Ma'alaea while relaxing in this recently constructed 3-bedroom condo, formerly the iconic WATERFRONT RESTAURANT. With 2 king beds, 1 queen sofa bed, a fold out bunk bed, extra large living room, and one of the largest condo...
Waipouli Beach Resort Partial Ocean 1 BD 2 BA
Relax in this light-filled one-bedroom condo with lovely partial ocean views. Perfect for two, it features a fully equipped kitchen, cozy living area, and lanai that’s perfect for enjoying the coastal breeze.Partial Ocean View 1 Bedroom 2 Bathroom• Kitchen features...
Wailea Beach Villas | PH205
Welcome to Wailea Beach Villas Penthouse 205, an elegant retreat that showcases sophisticated furnishings, vibrant colors, and striking artwork. This family-friendly penthouse features three bedrooms and three full baths, offering ample space for families or groups to...
Maui Resort Rentals: Honua Kai – 8 Total Bedrooms, Groundfloor Residences, Over 4600 Combined Sq. Ft., Large Lawn Areas, Steps to Pools/Beach/B.B.Q.s!
This remarkable offering combines 4 neighboring ground floor residences at the luxurious Honua Kai Resort to create a perfect retreat for large families and groups. Enjoy the space of a luxury home with all the advantages of resort living.Boasting a combined 4600 sq ft...
Maui Resort Rentals: Honua Kai - 4 Total Bedrooms w/ Beautiful Ocean & Lush West Maui Mountain Views!
This impressive 4BR offering combines two adjacent Mountainview residences with a neighboring partial oceanview studio, creating the perfect gathering place for larger groups or families—all at an excellent value!Overlooking the Konea Towers' beautiful courtyard,...
Ala Moana Hotel by Sandra Ocean view and balcony BEST RATE
The hotel unit is located within Ala Moana Hotel and next to the Ala Moana Center, the world's largest shopping mall. There is a skybridge that connect the hotel with the mall. Resort fees are separate ($25/day) and are paid directly to the hotel. The Ala Moana Condo...
Maui Kamaole #C-203 - Remodeled Upstairs Retreat with AC and Resort Pools!
Maui Kamaole #C-203Maui Kamaole #C-203 is a beautifully remodeled two-bedroom, two-bathroom upstairs unit offering a peaceful setting, modern comfort, and a fantastic location near some of South Kihei’s best beaches. This updated condo features island-inspired décor,...
Amazing & Modern Honolulu Haven, Renovated w/ AC
*** Disclosure: All rooms are renovated in a similar fashion. Furniture style may vary in pictures and in the unit. Functionality are all the same. Queen size bed in bedroom, sofa bed in the living room. Free tandem stall allowed park two cars. Pets friendly there is a...
Oceanside Kihei Condo | Steps to Beach | AC
Welcome to your perfect Kihei retreat! This beautiful 1-bedroom, 1-bathroom condo at Kihei Kai Nani offers an ideal location just steps from world-famous Kamaole Beach II. The spacious interior features cool ocean blue décor throughout, with a comfortable queen bed in...
Kihei Kai Nani ~ Building 6 Dream Location
Come to this Premier newly remodeled unit at the Kihei Kai Nani. Known for our desirable, ground floor unit. This unit has everything to make this your best vacation yet. Take in the tropical garden and pool view from this 2 bed, 1 bath unit with split AC. The King size...
The Secret Manor - artFULL living in Kona Coffee Country
Live like a local on this 5 acre secret estate that can sleep 20 with hot tub in Kona on the Orchid Isle of Hawaii. Designed by architect Skip Goodell. Great for creative retreats & family groups : be close but not TOO close to town or travel companions. Original...
Fabulous 8 bedrooms for 16 Poipu Kai. Steps to beach!
Listing provided by "The Vacation Rental Experts". Contact directly for more options!Beautiful 8 bedrooms for 16 in Poipu Kai is located only 250 yards to Brenneckes Beach and 350 yards to Poipu and Shipwreck Beach! Paved walkway from your door to the beaches! Only a...
New Listing! Napili Point C32 - Luxurious and Spacious Direct Ocean Front 2B/2B!
Discover Your Perfect Maui Getaway at Napili Point Resort C32If you're looking for the ultimate Maui escape, look no further than the oceanfront villas at Napili Point Resort C32. Nestled above the sparkling waters of Honokeana Bay, our 2-bedroom, 2-bathroom oceanfront...
Big Blue Whale - Spacious "Tiny" Home with COLD A/C
Large "tiny" house in the back of the main house now available!A short unpaved walkway along the side of the main house leads you to the back of the yard where this fully remodeled home with your own private entrance awaits. This spacious and clean home-away-from home...
Fairways 902: Stunning Golf Views, Lanai, Pool, Spa, AC & Beach Club Access
Escape to comfort at The Fairways at Mauna Lani 902 by Gather, a beautifully curated vacation rental where every detail ensures relaxation and enjoyment. Nestled in a prime location within the community, this lovely home overlooks the lush greens of the golf course,...
Charming studio on the 1st-Floor w/ ocean view, lanai, gas grills, pool, W&D
Kepuhi Beach Resort 1156Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome to your serene ocean view retreat in Maunaloa, HI! This charming studio condo offers the perfect blend...
Steps Away from Kalapaki Beach! Stunning Oceanfront Room | Outdoor Pool
This listing is for a room within a hotel.✦ Your room is 1000 sq. ft, equipped with complimentary toiletries, standard quality TV, available with Standard cable.✦ Daily cleaning services included in the nightly price.There are a few additional details to know before...
Princeville Kauai Condo Sleeps 3
Please Send An Inquiry Before Requesting To Book By Clicking The Contact Host Tab.Nestled on 22 acres along the beautiful coastline of the North Shore, the resort abounds with tropical foliage and amazing views of the green mountains, waterfalls, tropical sunsets over...
Sugar Beach #306-Ocean view condo located on the beach in N. Kihei, Sleeps 4
This updated one-bedroom, one-bath condo, with central A/C, sleeps up to four people with a king bed in the bedroom and a new queen sofa bed with an upgraded Tempurpedic mattress in the living room. This condo has all of the conveniences of home including a flat-screen...
Designer Studio in Hawaii Kai! Close to beaches, shopping, and hiking!
Come and enjoy this newly updated and professionally designed studio in beautiful Hawaii Kai. This fresh and inviting space is the perfect getaway and launch pad for all of your Hawaii adventures or just to relax and get away from it all.This is a gorgeous, designer...
Beachfront - Parking incl - Oceanview - Waikiki Shore
We can give you a in site parking.***Maxmum is only 2 persons ***COMPACT VEHICLE ONLY (Stall is very small with limited space)Please let us know if you will arrive in the unit after 5pm to 9am. If you would like to check in between the hours of 5pm -9am, we will charge...
Relaxing, Convenient Location In Waikiki!
You'll love waking up to the calming view of the Pacific Ocean in the distance! This beautifully appointed condo is located on the 15th floor of Discovery Bay, offering comfort, convenience, and a perfect home-away-from-home experience in Waikiki. For your convenience,...
Wailea Ekahi Village | 49B
Wailea Ekahi 49B is a stunning ocean view condominium located in the heart of the renowned Wailea resort area. Nestled along the pristine white sand beaches of Keawakapu Beach, this luxurious condo complex offers sits on 34 acres of lush tropical landscaping.Spanning...
1940’s Retro Shack By The Sea
The Poipu Aloha “Shack” is a lovingly restored 1940’s vintage cottage that blends the charm of old Hawaii with the ease of modern luxury. Nestled in one the best spots on the sunny side, Poipu Beach, this adorable two-bedroom retreat is just down the street from...
Magic Skies Top Flr Ocean View Under the Sea Room
Enjoy the panoramic views from your large top floor ocean facing room with private bathroom, walk-in shower and walk-in closet and kitchenette. The room has sea life themed decor and custom art and woodwork featuring a wall of ocean facing windows and double doors...
Top floor 1 bedroom Kihei beachfront gem with AC & partial ocean view
Welcome to Nani Kai Hale 403. Make your Maui memories from this top floor 1 bedroom partial ocean view beachfront condo. Feel right at home with everything from split AC in both the living room & bedroom, sofa sleeper, fully equipped kitchen, some beach gear, & luxury...
Menehune Shores #609 - Top-Floor Oceanview Condo Steps from Beach
Menehune Shores #609Enjoy the laid-back charm of South Maui at Menehune Shores #609, a top-floor Oceanview condo located just steps from the sandy shores of North Kihei. This two-bedroom, two-bathroom vacation rental is perfect for couples, families, or small groups...
Nihilani 18C Newly renovated plantation style home
Located on an upper floor and a corner unit .... this newly renovated and elegantly furnished town home will comfortably accommodate your family. Nihilani 18C features central air conditioning and garage parking. Sit on your lanai with a tropical beverage and enjoy the...
Royal Sea Cliff Kona Studio
Studio + Kitchen- Studio condos located on 3rd and 5th floors- Kitchen features stovetop, oven, refrigerator, microwave, dishwasher, coffeemaker, blender, cookware and tableware- Private balcony- 1 king bed- 600-650 sqft/55-60 sqm- Maximum 2 persons including children...
Waipouli Beach Resort C104 Garden View 2 BD 3 BA
Escape to this relaxing two-bedroom condo tucked among swaying palms and flowering gardens. Ideal for small groups or families, it offers a calm and comfortable home base with a distinct island feel.Unit C104 Garden View 2 Bedroom 3 Bathroom• Ground floor condo with...
Magic Skies Top Floor Dream
You are in paradise when you stay with us in the Top Floor Living space at Magic Skies! With 1,954 sq feet, the top floor is a complete living quarters! Enjoy the entire top floor all to yourselves, complete with 3 bedrooms (2 kings, 1 queen), 3 bathrooms (2 are...
Amaui Villa #9
Nestled within the exclusive enclave of Mauna Kea Resort, Amaui Villa 9 embodies Hawaiian luxury with breathtaking ocean views and thoughtfully designed spaces. The epicurean kitchen, adorned with premium appliances and natural stone countertops, seamlessly flows into...
Beautiful Poipu 6 Bedrooms for 12 with AC!
New Listing!!Gorgeous Poipu 6 bedrooms for 12 with AC! The 6 bedrooms are made up of two separate 3 bedrooms 3 baths for 6, just steps apart! 6 bedrooms, 6 baths for 12 total! This fabulous property located in wonderful proximity to Brenneckes, Poipu, and Kiahuna...
Waikiki Beach Studio Condo..Minutes to Beaches!nGreat Value.
Aloha and welcome to the ideal Waikiki studio Condo rental getaway in Waikiki...just a short stroll to incredible beaches! Ideally located at the start of Waikiki, near the marina, we are close to everything for your vacaction getaway. World-class shopping & wonderful...