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 Collectivité de Saint-Martin
4.75 out of 5 average rating, 8 reviewsMy Paradise Bleu beach house!
Home in Collectivité de Saint-Martin
5 out of 5 average rating, 5 reviewsVilla Taïana - Oyster Pond
Home in Sint Maarten lowlands Maho
4.78 out of 5 average rating, 58 reviewsVilla Blue Lagoon SXM
Home in MF
5 out of 5 average rating, 12 reviewsVILLA CECILIA
Home in Caribbean
4.88 out of 5 average rating, 52 reviewsPelican Paradise
Home in Collectivité de Saint-Martin
4.79 out of 5 average rating, 14 reviewsVilla Louisiana
Home in Mont vernon 3
4.67 out of 5 average rating, 3 reviewsVilla Carib sxm piscine.
Home in Parc de la Baie Orientale
4.78 out of 5 average rating, 9 reviewsMaison les Sucriers, Baie Orientale le Village
Condo rentals with a pool
Condo in Lowlands
4.8 out of 5 average rating, 69 reviewsLoft Condo - STEPS FROM BEACH!
Condo in Simpson Bay
5 out of 5 average rating, 29 reviewsCasaPisani Tranquil 2Bed condo SimpsonBayYachtClub
Condo in Lowlands
5 out of 5 average rating, 34 reviewsThe Cliff in Cupecoy Beach HEAVEN!!!
Condo in Lowlands
4.86 out of 5 average rating, 35 reviewsMaho 1BR Condo w/ocean view, pool & Free Wi-Fi
Condo in Upper Prince's Quarter
4.83 out of 5 average rating, 6 reviewsBeautiful, airy 2BR condo overlooking Dawn Beach
Condo in Simpson Bay
4.98 out of 5 average rating, 59 reviewsThe Beach Condo
Condo in Little Bay
4.93 out of 5 average rating, 15 reviewsLittle Bay- Stunning View, 2 bedroom, sleeps 6
Condo in Lowlands
4.92 out of 5 average rating, 24 reviewsEnjoy Stunning Sunsets Beachside 2 BR/2 Bath Condo
Home rentals with a private pool
Quick stats about vacation rentals with a pool in Simpson Bay
Total rentals
220 properties
Nightly prices starting at
$60 before taxes and fees
Total number of reviews
5.1K reviews
Family-friendly rentals
120 properties are a good fit for families
Pet-friendly rentals
50 properties allow pets
Rentals with dedicated workspaces
90 properties have a dedicated workspace
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