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Front Street Cottage Rentals & Holiday Homes

Find the best cottages in Front Street - We found 15 exact matches

About Front Street Cottage Rentals on Wailea Vacation Rentals

Searching for cottages to rent near Front Street? Wailea Vacation Rentals features more than 15 cottages that are perfect for your next trip. Discover luxury cottage rentals that are a few miles away from the lake or beach. These cottage rentals in Front Street have hot baths, are kid-friendly & family-friendly, and are near top local attraction spots, to give guests the best travel experience they could ever wish for. Wailea Vacation Rentals’s cottage listings come in all shapes and sizes for large groups, friends, or couples in Front Street.

Are you planning to travel to the lakeside, beach, or mountain area? Wailea Vacation Rentals’s cottage rentals offers a wide selection, giving you direct access to the owners of these cottage rentals, and offering you the best opportunity to find a good price.

Wailea Vacation Rentals boasts of 15 holiday cottages and places to stay in Front Street. The site provides unique Airbnb, VRBO, Wailea Vacation Rentals-style cottages to fit your trip or get away with your friends and family. This can be a weekend getaway, spring break, summer vacation, or annual holiday -- all fitting within your budget.

Frequently Asked Questions About Front Street Cottage Rentals

How much does it cost to rent a cottage in Front Street?

The average cost for a cottage rental in Front Street is $551 per night. Waileavacationrentals has a wide list of great cottages near Front Street that would suit your needs. There are single and multiple rooms for solo trips or family vacations.

Do you have any rental cottages in Front Street that are suitable for families?

Most of our listed cottages are suitable for families. Check out the complete list of cottages in Front Street to find one that works for you.

Are there quality cottages in Front Street that have indoor swimming pools?

As of 2026, the data from Waileavacationrentals shows that there are Over 15 private swimming pools or cottages with indoor pools in the Front Street area along with other great amenities.