Monthly Rentals in Simm's Settlement

Discover long-term rentals that feel like home, for stays of a month or longer.

Nearby monthly rentals

Cottage in Stella Maris
5 out of 5 average rating, 5 reviews

Near stunning Cape Santa Beach, WiFi and Sat TV

TheidraRating, 5 stars12 months ago
It was the first time my family and I visited Long Island. We met Docky and Jill and they made us feel at home from the very beginning. Starting from the simplest details of providing, coffee, tea, bug spray, baby oil for mosquitoes to the more complex like taking time out to direct us everywhere on the entire island. The home is equipped with all of the basics even some cooking seasonings. The yard is big and has a beautiful huge tamarind trees. a nice gazebo, grill and the house hilltop view was spectacular. We had true privacy and the neighbors were quiet and kept to themselves. We never saw them..You definitely will need a car to get around especially to restaurants and grocery shopping. It’s located to the very northern tip of the island. The busiest settlement is 45 minutes to the south. We will be back again and will be delighted to book with Bonafide fishing house again. We didn’t do any fishing with Docky because of the rain. We came as visitors and left feeling like locals.
Apartment in Stella Maris
4.58 out of 5 average rating, 24 reviews

Apt for rent, walking distance to pool & beach!

JorgeRating, 5 stars7 months ago
Great place to stay!! Everyone is very friendly and the views are incredible.
Top Guest favourite
Cottage in Long Island
4.99 out of 5 average rating, 162 reviews

Tiny's - Toes In The Sand Key Lime Cottage.

AmandaRating, 5 stars2 weeks ago
Wow is all I can say! Exceeded expectations!! We can’t wait to come back!!
Top Guest favourite
Cottage in Long Island
4.92 out of 5 average rating, 39 reviews

Sunset Studio Cottage/ Hilltop/Sea views

RamonaRating, 5 stars1 month ago
Our stay was wonderful. The beaches are beautiful and many times we were the only two people on the beach. This is a very quiet island a great place to unwind. Henley is an exceptional host. He was on the island as well and shared a lot of information about the island. He even took us on a Sunday drive . The bed was comfortable, and the kitchen had everything we need. We highly recommend this cottage.

Amenities and perks for longer stays

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