Lahaina Winter Rentals & Holiday Homes

There are a lot of options in Lahaina. If you plan on staying in the Lahaina area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Lahaina:

• HOKULANI 436-CORNER UNIT 2BD/2BA w/OCEAN & MOUNTAIN VIEWS,505SQFT LANAI BALCONY
• Mahana at Kaanapali, Spectacular Oceanfront, Amazing Sunsets & Sea Life Unit1014
• SLEEP NUMBER BED! #759 1bdrm-A Guest Favorite-Ocean/Beach View w/XBOX & ROKU!
• nRead Our Reviews and See Why Our Guests Love to Stay with Us.
• The Whaler! ~Beautifully remodeled ground floor courtyard studio~
• Luxury Studio | 5 star Honua Kai Resort Konea 215 | Beach Access | AC | Pools
• Views! Views!
• Maui Resort Rentals: Hokulani 605 – Premier 6th-Floor Oceanview Penthouse | Closest 2BR Column to the Ocean!
• MAHANA ON THE BEACH-PREMIUM 11th FL CORNER 270 DEG OCEANFRONT VIEWS 2BR/2BA
• 4 Diamond OCEANFRONT Honua Kai, OCEAN VIEW large Konea STUDIOnon Kaanapali Beach

The average cost for winter rentals in Lahaina is $1,208 per night. Travelthehorizon has a wide list of great winter places to stay near Lahaina that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.

Yes, here are the top cottage/chalet rentals in Lahaina that allow you to bring your pet or dog:

• Breathtaking Transformation! Luxury 3-BR Oceanfront Condo
• Lahaina Oceanfront Estate-Main House
• Puunoa - CoralTree Residence Collection
• May 199 nightly plus fees. Pay owner for clean fee prior to arrival. BEACHFRONT

See all pet-friendly vacation rentals in Lahaina on Travelthehorizon

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Lahaina to find what works for you.

As of 2026, the data from Travelthehorizon shows that there are over 6961 private swimming pools or indoor pools accommodations near Lahaina along with other great amenities.