Vacation rentals with a pool in Simpson Bay
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Simpson Bay
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Simpson Bay rentals with a pool
House rentals with a pool
Home in Simpson Bay, Sint Maarten
5.0 out of 5 average rating, 70 reviewsVilla Blue View .. stunning views of endless sea!
Home in Cole Bay, Sint Maarten
4.89 out of 5 average rating, 38 reviewsSaint-Tropez With Ocean View - Boat Charter
Home in Philipsburg, Sint Maarten
5.0 out of 5 average rating, 7 reviews2 Bedroom Ocean Front Villa
Home in Lowlands, Sint Maarten
4.9 out of 5 average rating, 69 reviewsSapphire Fantasy : Oceanfront paradise
Home in Simpson Bay, Sint Maarten
4.9 out of 5 average rating, 10 reviewsCoco's Beach House - Simpson Bay Beach
Home in Upper Prince's Quarter, Sint Maarten
5.0 out of 5 average rating, 7 reviewsTeresa’s Ocean Paradise
Home in Cole Bay, Sint Maarten
5.0 out of 5 average rating, 20 reviewsSpacious 3BR with Private Cozy Pool
Home in Collectivity of Saint Martin, St. Martin
5.0 out of 5 average rating, 14 reviewsFantastique villa 2chambres, piscines, tennis
Condo rentals with a pool
Condo in Orient Bay, St. Martin
4.88 out of 5 average rating, 264 reviewsCharming Studio 1 in Baie Orientale (Orient Bay)
Condo in Marigot, St. Martin
4.82 out of 5 average rating, 115 reviewsGorgeous studio ON THE BEACH,ocean view
Condo in Maho , Sint Maarten
4.79 out of 5 average rating, 14 reviews'Emerald Pearl' Studio in Maho with Full Amenities
Condo in Lowlands, Sint Maarten
4.86 out of 5 average rating, 65 reviewsAmenity-Filled Maho Studio, Close to Airport/Beach
Condo in Simpson Bay, Sint Maarten
4.9 out of 5 average rating, 10 reviewsLovely Lagoon Townhouse SBYC
Condo in Lowlands, Sint Maarten
4.95 out of 5 average rating, 91 reviewsSint Maarten La Terrasse Maho
Condo in Saint Martin,Guadeloupe, St. Martin
5.0 out of 5 average rating, 28 reviewsVilla Belharra, amazing view
Condo in Cole Bay, Sint Maarten
4.83 out of 5 average rating, 42 reviews3 Palms - A lovely 2 bedroom condo with pool.
Home rentals with a private pool
Condo in Upper Prince's Quarter, Sint Maarten
New Listing! Coral Beach Club Condo, Dawn Beach
Villa in Toiny, St. Barthélemy
South Wave
Home in Saint-Martin , St. Martin
Rental Villa Saint-Martin, 3 bedrooms, 6 persons
Home in Saint-Martin , St. Martin
New place to stayRental Villa Saint-Martin, 4 bedrooms, 8 persons
Home in Saint Martin, France
Rastafari
Quick stats about vacation rentals with a pool in Simpson Bay
Total rentals
200 properties
Rentals with dedicated workspaces
80 properties have a dedicated workspace
Pet-friendly rentals
40 properties allow pets
Family-friendly rentals
110 properties are a good fit for families
Total number of reviews
4.6K reviews
Nightly prices starting at
$82 CAD before taxes and fees
Destinations to explore
- Orient Bay Vacation rentals
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- Rentals with pools Saint Martin
- Rentals with pools Sint Maarten
- Rentals with pools Sint Maarten
- Rentals with pools Saint Barthélemy
- Condo rentals Simpson Bay
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- Rentals with a hot tub Simpson Bay
- Serviced apartment rentals Simpson Bay
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- Monthly Rentals Simpson Bay
- Rentals with outdoor seating Simpson Bay
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