Monthly Rentals in Simpson Bay

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

Nearby monthly rentals

Superhost
Condo in Simpson Bay
4.8 out of 5 average rating, 166 reviews

Oceanfront w private Pool | Maho Beach area

CindyRating, 5 stars2 weeks ago
We loved Jean’s place. I hated leaving. The serenity, views and comfort were wonderful. The sound of the waves crashing on the cliffs so calming, we slept to the sound every night. We loved seeing various iguanas out the window every day. Jean informed us of some good restaurants. I just can’t see staying on a mountain or back from the beach. The water views are astounding. You will never want to get out of the shower, lol
Guest favorite
Apartment in Simpson Bay
4.82 out of 5 average rating, 114 reviews

Apartment on the beach 3

ProssieRating, 5 stars4 weeks ago
One thing that stood out about this place is how well furnished it was. Whatever you think you need, you could find. Everything from a well stocked kitchen (with everything including a coffee machine, blender, baking pans, dishes, places, cups, knives, glasses, oven, fridge etc) to beach chairs and noodles, to an abundance of towels, Lucy and Radek have truly turned this into a home away from home for every guest. Lucy was gracious in letting me borrow an electric mosquito zapper racket which took care of the bugs and mosquitoes. With the house being on the beach, you walk out and straight into the beautiful Simpson Bay beach. The apartment is located in a quite neighborhood with friendly locals who always greeted me with a smile as I passed, but it is also located very close to all the amenities you need (stores, restaurants, casinos, clubs etc). If you take excursions, you will be walking distance from the dock and the boats! I would unreservedly recommend this apartment!
Guest favorite
Condo in Lowlands
4.87 out of 5 average rating, 63 reviews

Maho studio overlooking airport, Free Wi-Fi!

EricaRating, 5 stars2 days ago
Awesome stay! We loved how close everything in Maho was to the condo. The view from the balcony was such a treat as aviation fans. Chris was always quick to message us back with answers to our questions, and we appreciated that he checked in with us to ensure our whole stay was wonderful. Great host - we’d love to come back and stay exactly here again ☺️
Top guest favorite
Apartment in Simpson Bay
5 out of 5 average rating, 36 reviews

The Loft at Simpson Bay Yacht Club

KendallRating, 5 stars6 days ago
love this place. It's a great location with nearby restaurants, markets, and Kim Sha beach, which is a 7 minute walk. My favorite thing about this air bnb is the safety. There is a guard that let's you into the property every time. I felt at peace sleeping here. I took advantage of the property's pools, which are nice and have great views. Overall, a great stay! Random thing to note: there is no TV in the bedroom upstairs.

Amenities and perks for longer stays

Furnished rentals

Fully furnished rentals include a kitchen and the amenities you need to live comfortably for a month or longer. It’s the perfect alternative to a sublet.

Flexibility you need

Choose your exact move-in and move-out dates and easily book online, without any additional commitment or paperwork.*

Simple monthly prices

Special rates for long-term vacation rentals and a single monthly payment without additional charges.*

Book with confidence

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Work-friendly spaces for digital nomads

Traveling professional? Find a long-term stay with high-speed wifi and dedicated working spaces.

Looking for serviced apartments?

Airbnb has fully furnished apartment homes ideal for staffing, corporate housing, and relocation needs.

Stay near Simpson Bay's top sights

Maho Beach72 locals recommend
Carrefour Market, Sint Maarten61 locals recommend
Karakter Beach Bar/Restaurant48 locals recommend
Avantika36 locals recommend
Soggy Dollar Bar31 locals recommend
The RedPiano Lounge29 locals recommend

Destinations to explore

*Some exclusions may apply in certain geographies and for some properties.