
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

Pelican key - BEACH FRONT Villa

Ocean View Villa-Indigo Bay W/Private Pool/0 Steps

Life's Good

Breathtaking views of St Barth - 8 people

New-Sunset Place Villa w Stunning Waterfront Views

SEA TRUE VILLA,Lavish,Sea view near Maho&Mulletbay

The best view on the island!

Préstige - Luxurious 3 bedroom by the Beach
Condo rentals with a pool

Waterfront, beautiful ELBA! 2 to 4 people

Villa Belharra, amazing view

"SeaBird" studio, feet in the water on the beach

Maho Vibes Condo

Maho 1 Bed Condo with ocean view & Free Wi-Fi

The Beach Condo

Beachfront Caribbean Breeze in Paradise, SXM

Blue vista - Paradise in nettle Bay-1BR Queen Size
Other vacation rentals with a pool

Waterfront "Bonjour" Beacon Hill St Maarten

Gorgeous 2 bedroom-17th floor, Fourteen Mullet Bay

NEW 1BR apt lagoon & sunset view 4/5p

Beacon Hill Hideaway: Luxury Condo in Simpson Bay

'Emerald Pearl' Studio in Maho with Full Amenities

Love beach loft

Palm View Condo with pool

The Pineapple Suite
Quick stats about vacation rentals with a pool in Simpson Bay
Total rentals
240 properties
Nightly prices starting at
$83 CAD before taxes and fees
Total number of reviews
5.9K reviews
Family-friendly rentals
120 properties are a good fit for families
Pet-friendly rentals
60 properties allow pets
Rentals with dedicated workspaces
100 properties have a dedicated workspace
Destinations to explore
- San Juan Vacation rentals
- Carolina Vacation rentals
- Culebra Vacation rentals
- Sainte-Anne Vacation rentals
- Saint Thomas Vacation rentals
- St. Croix Vacation rentals
- Fort-de-France Vacation rentals
- Tortola Vacation rentals
- Basse-Terre Island Vacation rentals
- Le Gosier Vacation rentals
- Aguadilla Vacation rentals
- Luquillo Vacation rentals
- Family-friendly rentals Simpson Bay
- Condo rentals Simpson Bay
- Rentals with beach access Simpson Bay
- Apartment rentals Simpson Bay
- Beach condo rentals Simpson Bay
- Pet-friendly rentals Simpson Bay
- Rentals with a hot tub Simpson Bay
- Serviced apartment rentals Simpson Bay
- Rentals with outdoor seating Simpson Bay
- Rentals with a washer and dryer Simpson Bay
- Rentals with breakfast Simpson Bay
- Rentals with a patio Simpson Bay
- Waterfront rentals Simpson Bay
- Beachfront rentals Simpson Bay
- Fitness-friendly rentals Simpson Bay
- Smoking-friendly rentals Simpson Bay
- House rentals Simpson Bay
- Villa rentals Simpson Bay
- Rentals with pools Sint Maarten