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Island Stays with More Comfort
Find Hawaii vacation rentals across Oahu, Maui, Kauai, Big Island, Molokai, and Lanai, including beachfront condos, private homes, studios, and luxury villas. These island stays offer more space, privacy, kitchens, lanais, and flexible home bases for beach days, activities, family trips, honeymoons, and longer vacations.
Browse by Island
Start with the island you are visiting, then narrow your search by resort area, town, beach access, bedroom count and rental style.
Waikiki condos, Ko Olina villas, North Shore homes and beach towns near Honolulu.
Explore Oahu
Kaanapali condos, Kihei beach stays, Wailea villas and West Maui resort rentals.
Explore Maui
Princeville, Poipu, Hanalei, Kapaa and scenic rentals near beaches and lush valleys.
Explore Kauai
Kona Coast condos, Kohala resort villas, Hilo stays and Volcano-area retreats.
Explore Big Island
Low-key condos and homes near Kaunakakai, Maunaloa and relaxed island scenery.
Explore Molokai
Quiet island stays for travelers looking for space, privacy and a slower pace.
Explore LanaiPopular Rental Areas
Compare well-known beach towns, resort districts and oceanfront communities before choosing where to stay.
Rental Finder
Use these quick links to jump into the most requested Hawaii vacation rental areas. Each island has a different mix of resort condos, beach homes, villas and quieter neighborhood stays.
Oceanfront condos, large homes and holiday dates can sell out well before peak travel weeks.
Check kitchens, pools, parking, laundry, air conditioning, beach access and sleeping layouts.
Pick a base near the beaches, tours, restaurants and driving routes you plan to use most.
Review final rates, cleaning fees, taxes, house rules and cancellation policies before booking.
Featured Rentals
Browse featured Hawaii vacation rentals from the current listings.
From $325/night
Aloha! This Beautifully Designed and Updated (March 2026) Large one bedroom condo unit is Tastefully redone to complement its Natural Surroundings....
From $386/night
Oceanfront 2bd/2ba Unit with Amazing Ocean Views & A/C. Oceanfront, 2 bedrooms, 2 bathrooms, Tile floors, tile showers, granite counters and bar, new...
From $176/night
Traveling with the family or taking time for yourself, you'll love coming home to this beautiful home. Three bedrooms each with their own ensuite...
From $302/night
This air-conditioned direct oceanfront unit on the 3rd floor (with elevator) overlooks a large lava tide pool that is frequented by turtles and...
From $421/night
Kolea 15G at Waikoloa Beach Resort -- Amazing Location -- 5 minutes walking to the beach -- Heated Infinity Pool and Hot Tub with Ocean View --...
From $206/night
COME TO OUR TROPICAL PARADISE AND EXPERIENCE THE SERENE, MAJICAL FLEELING OF OUR OCEANFRONT LANAI AT SUNSET. EXTRA AMENITY If you are arriving early...
From $475/night
If you like Kauai Haven (VRBO Listing #683110), you're going to love this condo too. It is nestled within a classic Hawaiian style backdrop, resting...
From $398/night
Maui Permit #BBPH 2009/0002 , Hawaii Permit #SUP2 2002/0005Hawaii Tax I.D. TA035-442-8928-01 TMK (2)2-7-035-010-0000Maui's Ultimate Private, Romantic...
Hawaii Rental Planning Support
Use island, town, rental style and amenity details together so your lodging choice supports your beach days, tours, meals and driving plans.
Hawaii vacation rentals include beachfront condos, oceanview villas, resort residences, private homes, studios, cottages and larger estates for families or groups.
Oahu is convenient for Waikiki, Ko Olina and city access. Maui has many resort condos and beach communities. Kauai offers scenic, quieter stays, while the Big Island has Kona Coast, Kohala Coast and Volcano-area rentals.
Yes. Many rentals offer kitchens, separate bedrooms, lanais, laundry, parking and resort amenities, which can work well for families and groups who want more space than a hotel room.
Book early for holiday weeks, summer, winter high season, oceanfront units, larger homes and rentals in popular areas like Waikiki, Kaanapali, Kihei, Wailea, Princeville and Kailua-Kona.
Review the final nightly rate, fees, taxes, cancellation policy, sleeping layout, parking, air conditioning, beach access, pool access and house rules on the partner booking page.