Hawaii long-term rentals

Call (888) 257-7970 for additional information about long-term bookings.

View from the deck overlooking the beach and the ocean at a vacation rental in Hawaii.
The living area overlooking the ocean at a vacation rental in Lahaina, HI.

A long-term vacation to look forward to

Receive a discounted rate on many of our monthly rentals (displayed at check-out) and reductions in our usual fees. We also allow for partial payment if you book at least 45 days ahead of time.

Plus, enjoy peace of mind with our simple cancellation policy and optional travel insurance.

Overview of a vacation rental in Hawaii on the beach with a hot tub.

Ease into island time

Swinging hammocks, swaying palms, and impeccable ocean views—enjoy it all for a month or longer with a long-term vacation rental. Remote work and schooling have made it easier than ever to plan a snowbird trip or extended stay in dream vacation destinations—Hawaii, especially. Take your time traversing through the jungle, sightseeing one island at a time, or savoring your slice of paradise by the beach. Find monthly house rentals, condos, and resorts with amenities like nearby golf courses, on-site dining, hot tubs, swimming pools, ocean access, and more.

Drone shot of a vacation rental with a pool in Koloa, HI.

FEATURED LONG-TERM VACATION HOME IN HAWAII

Makena

Koloa, Kauai

Experience Kauai bliss. Relax with your family on a long-term stay with everything you need, like a spacious kitchen, a washer/dryer, an outdoor eating area, a swimming pool, and a hot tub. When it comes time to hit the beach or the fairways, it’s only a short trip to Baby Beach, Poipu Beach, and Kiahuna Golf Club. Stay close to dining, shopping, and surf schools from the comfort of a breezy monthly vacation rental.

Long-term vacation destinations on the Big Island

covered resort patio with views of ocean waves, beach, and palm trees
Kailua-Kona

Kailua-Kona offers a taste of Big Island culture on the western coast. Snorkel along Kamakahonu Beach’s colorful coral reef, tour through Kaloko-Honokōhau National Historical Park, and sample the area’s incredible coffee scene.

Aerial shot of vacation rentals on the coast of Keaau, HI.
Keaau

If you’re looking to reconnect with nature and relax at a slower pace, try the small town of Keaau. Here, you’ll find yourself surrounded by breathtaking state parks, nature reserves, protected forests, the Hawaii Volcanoes National Park, and panoramic ocean views.

Waikoloa

Enjoy comfort and convenience from Waikoloa—with luxury accommodations, resort-style amenities, and a shopping district, all just 15 minutes from the beach.

View of golf course from a vacation rental in Princeville, HI

Our favorite long-term rentals on the Big Island

Maui Kaanapali beach aerial shot.

FEATURED LONG-TERM VACATION DESTINATION ON MAUI

Kaanapali

Home to award-winning beaches and endless adventure, Kaanapali rests only 30 miles from the Kahului Airport. Here, you can bask in the sun by the pool, snorkel in deep-blue waters at the iconic Black Rock Beach, enjoy shopping at Whalers Village, and attend an island Luau to experience the taste and rich culture of the Hawaiian Islands.

Long-term rentals on Maui

With a monthly condo rental in Maui, you can take advantage of resort-style amenities like ocean views, swimming pools, hot tubs, fitness centers, tennis courts, and its centralized location to shops, restaurants, beaches, and attractions.

A bedroom with a view at a long-term rental in Honolulu, HI.

FEATURED LONG-TERM CONDO RENTAL

The Landmark #2705

Honolulu, Oahu

Live the high life from a lofty condo in the heart of Waikiki. With its high-end furnishings, centralized location, city, and ocean views, elegant design, and luxury amenities, you’ll be wanting to extend your long-term vacation a little longer. Sip your morning coffee on the private balcony, enjoy easy walkability to shopping, dining, and the beach, and indulge in the resort’s rooftop pool, hot tub, and fitness center.

Long-term destinations on Kauai

Aerial shot of North Shore, Maui.
North Shore

North Shore is legendary for a reason. Keep world-famous surfing, incredible food trucks, pineapple farms, and thriving coral reefs at your fingertips with a long-term vacation rental.

Poipu Bay shoreline in Poipu, HI
Poipu

An extended stay in Poipu is a great choice for those traveling with family or children. Enjoy tranquil kid-friendly beaches, check out nearby Spouting Horn, and end your evenings with a few dazzling sunsets.

covered resort patio facing lush manicured grounds and ocean in hawaii
Kapaa

Take your time savoring Kapaa’s small-town charm with a long-term vacation rental. Though its beaches are rocky, you’ll find plenty of fun between the town’s boutiques, delicious dining options, shaved ice stands, and the area’s beautiful waterfall hiking trails.

Princeville

Looking for a little luxury? Treat yourself to a month or more of ocean views, lavish spas, impressive golf courses, and beachside bliss. Snag an oceanfront stay and let your worries slip away.

Our favorite long-term rentals on Kauai

The view of the back of a long-term vacation rental in Honolulu, HI.

FEATURED PET-FRIENDLY LONG-TERM RENTAL ON O’AHU

Kalanianole Estate

Located between Waikiki and Hawaii Kai, this luxurious pet-friendly vacation rental offers a getaway you’ll never forget. Bring the whole family for fun on the beach in your own backyard. Boasting oceanfront access and ocean views, a fully-equipped kitchen and wet bar, a pool table, a swimming pool and hot tub, an outdoor dining area, a fire pit, and nearly 4,300 square feet of living space, your family will be talking about this long-term vacation for years to come.

Long-term rentals on O’ahu

O’ahu has the most must-see places for any Hawaiian vacation. Here you’ll find the state’s capital, Honolulu, as well as Waikiki Beach, Pearl Harbor, and the North Shore. For youngsters, parks like Sea Life Park Hawaii or Honolulu Zoo make exploring O’ahu with kids a breeze. Adventure to your heart’s content with the perfect long-term resort, home, or condo vacation rental.

Long-term rentals on Molokai

Molokai spans 38 miles of stunning natural landscape, with Hawaii’s highest sea cliffs, longest continuous fringing reef, and not a skyscraper in sight. Reserve your long-term vacation rental and experience a slice of island life untouched by modernity.

Long-term oceanfront rentals in Hawaii

Nothing should come between you and the beach. Savor ocean views from sunrise to sunset, with access to beach activities and water sports in an oceanfront vacation rental.

luxurious hawaii vacation home with outdoor hot tub and wraparound deck surrounded by lush greenery

FEATURED HOME WITH BEACH ACCESS

Sandcastles

Anahola, Kauai

Relax with room for you and your crew to spread out on the beach. This oceanfront vacation home is the perfect place to create lasting memories with family, with stunning ocean views, beach access, a spacious enclosed yard, beach gear, and a hot tub. Take your time getting to know nearby Anahola and learn how to catch a wave with surf lessons.

The pool area at a vacation rental in Kailua-Kona, HI.

FEATURED HOME WITH PRIVATE POOL

Kona Kanewa Home

Kailua-Kona, The Big Island

Seek out adventures through the jungle, savor the warm ocean waves, then return to your rental for some well-deserved rest and relaxation. This charming retreat is perfect for a couple or small family’s long-term vacation, with a private pool and backyard, a grilling area, ocean views, and rooftop deck—all a quick drive from the airport and downtown Kailua-Kona. Settle into tropical paradise in this private sanctuary.

The covered deck overlooking the jungle at a vacation rental in Princeville, HI.

FEATURED EXTENDED STAY WITH MOUNTAIN VIEWS

Hale Carly & Lia Lani

Princeville, Kauai

Welcome to an escape that’s easy on the eyes. Sit back on the deck for some downtime with loved ones while admiring mountain views and distant waterfalls. Pick some ripe fruit to add to your breakfast from the backyard fruit trees, savor a soak in the jetted tub, and rinse off ocean salt in the outdoor shower. Unwind with a home base the whole family is sure to love.

Golf vacation rentals in Hawaii

Explore Hawaii golf resorts offering extended stays

Plan a trip away to play on island time, where palm trees and beach breezes are perfectly on par. Reserve your extended stay at a monthly vacation rental that keeps fairways at your fingertips. With 16 golf clubs on the Big Island alone, you can spend your vacation touring one course at a time.

Best places to buy a beach house 2021 - Sugar Beach Resort, Kihei, HI
Sugar Beach Resort in Kihei

Not only can you enjoy the resort’s namesake sugar-white sand beaches (the longest continuous stretch of shoreline in Hawaii), but after practicing your swing along the resort’s putting greens, try out the world-class golf courses just minutes away.

View from the pool at the Waikoloa Beach Resort.
Waikoloa Beach Resort in Waikoloa

If a tropical paradise isn’t tempting enough, this beachside resort also boasts ocean views, sparkling outdoor pools, and Hawaii’s “Premiere 27-Hole Golf Experience.”

Aerial shot of Pili Mai Resort.
Pili Mai Resort

Located right on the 18-hole Kiahuna Golf Course, this resort condo is the perfect home base for a golf getaway. After a day on the green, surrounded by gorgeous mountain views and ocean breezes, take a dip in the waves at nearby Poipu Beach.

Two chairs overlooking a lush Hawaiian golf course.

FEATURED MONTHLY RENTAL FOR GOLFING

Hale On'tario

Princeville

This home overlooks the sixth hole of Princeville’s premier golf club, Princeville Makai Golf Club. It's spacious and surrounded by palm trees, making your Hawaiian dream oasis a reality. Enjoy stunning, panoramic views of the Pacific Ocean, the Bali Hai Mountains, and of course, the golf course.

Hawaii long-term stays FAQ

In many cases, yes. If your reservation is eligible for a discount, you’ll see that reflected in the price when you book. Our long-term reservation sales specialists can also help answer any questions about discounts. Call (888) 257-7970) or email snowbirdreservations@vacasa.com.

You don't have to pay all at once. In fact, you’ve got a couple of different options to pay in installments. First, you can make monthly payments (over 3, 6, or 12 months) on most reservations through our partnership with Affirm. It’s easy, too—just select “Pay later with Affirm” when completing your vacation purchase.

If you book at least 45 days before your trip, your other option is to split your trip into just two payments. If the cost of your reservation is between $2,000 and $9,999, 50% is due at the time of booking. If the cost of your reservation is over $10,000, 25% is due at the time of booking. If you choose to make two payments, you must make your second payment 30 days before the start of your trip.

Hawaiian vacation inspiration