Vacation rentals with a pool in Sint Maarten

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Top-rated rentals with a pool in Sint Maarten

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Guest favourite
Condo in Maho
2 Min to Beach/Exclusive Rooftop Jacuzzi, Pool+Bar
This charming, cozy, and tranquil tropical nest is located where all the action is! The golf course, iconic bars, the unprecedented landing strip, the popular Maho and Mullet bay beaches, Maho market with daily fresh take away breakfast/lunch buffets and a divine selection of exotic restaurants are all in walking distance! If you wish to just lounge and relax by the pool, jacuzzi, and private gazebo bar or enjoy the nightlife; it’s all readily available, at your fingertips!
Oct. 14 – 21
$245 CAD per night
4.88 out of 5 average rating, 162 reviews
Guest favourite
Home in Calabash Rd, Cole Bay
THE HILL HOUSE, 2 Bdr, pool, panoramic view
The house consists of 2 beautiful bedrooms with pool in the residential area of Almond Grove Estate, secured 24 hours a day, (luxury residence), the villa is completely private, you will not share the pool and its yard. You will appreciate the charm of this house. The view is just magnificent, green hills and sea of Simpson Bay, a place both discreet and close to tourist hustle and bustle, shopping and beaches.
Oct. 22 – 29
$402 CAD per night
4.92 out of 5 average rating, 104 reviews
Guest favourite
Apartment in Little Bay
Stunning 2 BD Ocean View - Terraces Lt Bay
Treat yourself to the utmost stylish and modern ocean view apartment located in the exclusive Little Bay Hill . This spacious environment, is designed to be enjoyed as a family, has a terrace with stunning sea views, private pool, one master suites ( Japanese king bed and a walking closet), one bedroom suite with two twin size beds ( could be converted to king size bed ) . Welcome to Terraces Little Bay !
Jul. 18 – 25
$522 CAD per night
4.98 out of 5 average rating, 106 reviews

Popular amenities for Sint Maarten rentals with a pool

House rentals with a pool

Guest favourite
Home in Sint Maarten
Lux 5* Indigo Bay Villa Private Pool-Walk to Beach
Jun. 5 – 12
$875 CAD per night
5.0 out of 5 average rating, 60 reviews
Superhost
Home in Cay Bay
Luxury Villa Summer Sea - Indigo Bay SXM
Apr. 14 – 21
$864 CAD per night
4.93 out of 5 average rating, 92 reviews
Superhost
Home in Lowlands
Sapphire Fantasy : Oceanfront paradise
Jun. 7 – 14
$666 CAD per night
4.9 out of 5 average rating, 67 reviews
Guest favourite
Home in Simpson Bay
Villa Blue View .. stunning views of endless sea!
Sep. 2 – 9
$1,084 CAD per night
5.0 out of 5 average rating, 62 reviews
Superhost
Home in Philipsburg
Villa Allamanda a Indigo Bay
Nov. 6 – 13
$870 CAD per night
4.96 out of 5 average rating, 47 reviews
Superhost
Home in Sint Maarten
Stunning 5 bedroom villa with 180° ocean view !
Feb. 7 – 14
$1,029 CAD per night
4.75 out of 5 average rating, 85 reviews
Guest favourite
Home in Sint Maarten
Puerta Al Mar Villa
Sep. 22 – 29
$1,106 CAD per night
4.8 out of 5 average rating, 5 reviews
Guest favourite
Home in Upper Prince's Quarter
Villa Tamarind | Luxury Oasis | Ocean views | 4BDR
Oct. 9 – 16
$1,124 CAD per night
5.0 out of 5 average rating, 56 reviews
Guest favourite
Home in Upper Prince's Quarter
Tropical Oasis/Million $ Views!
Jul. 15 – 22
$918 CAD per night
5.0 out of 5 average rating, 6 reviews
Superhost
Home in Upper Prince's Quarter
«La Vue SXM» Paradise "Villa Rosa" 5 bedroom Rate
May 13 – 20
$1,152 CAD per night
5.0 out of 5 average rating, 3 reviews
Superhost
Home in Sint Maarten
Villa 2 Chambres Indigo Bay
Jun. 12 – 19
$617 CAD per night
4.71 out of 5 average rating, 7 reviews
Guest favourite
Home in Cole Bay
Spacious 3BR with Private Cozy Pool
Jan. 15 – 22
$605 CAD per night
5.0 out of 5 average rating, 12 reviews

Condo rentals with a pool

Guest favourite
Condo in Simpson Bay
Beach front luxury! Huge 2BR that has it all! 😍🤩😍
Sep. 11 – 18
$850 CAD per night
5.0 out of 5 average rating, 52 reviews
Superhost
Condo in Pelican
SeaLaVie Apartment with Private Pool
Sep. 11 – 18
$423 CAD per night
4.89 out of 5 average rating, 27 reviews
Guest favourite
Condo in Simpson Bay
Five Star Luxury Beachfront Condo Private Hot Tub
Feb. 22 – Mar. 1
$1,064 CAD per night
4.96 out of 5 average rating, 71 reviews
Guest favourite
Condo in Simpson Bay
Encanto -2BR beachfront w/pool & gorgeous sunsets!
Nov. 22 – 29
$515 CAD per night
5.0 out of 5 average rating, 23 reviews
Superhost
Condo in Lowlands
Amenity-Filled Maho Studio, Close to Airport/Beach
Aug. 30 – Sep. 6
$172 CAD per night
4.84 out of 5 average rating, 55 reviews
Guest favourite
Condo in Lowlands
Loft Condo - STEPS FROM BEACH!
Nov. 8 – 15
$128 CAD per night
4.81 out of 5 average rating, 48 reviews
Guest favourite
Condo in Lowlands
Brand New- Maho Condo Studio with Seaview and Pool
Oct. 2 – 9
$151 CAD per night
4.93 out of 5 average rating, 29 reviews
Guest favourite
Condo in Philipsburg
Apt3 - 3 bedrooms amazing sea view, terrace, Pool
Aug. 6 – 13
$474 CAD per night
4.79 out of 5 average rating, 38 reviews
Guest favourite
Condo in Lowlands
Gorgeous Beachfront PENTHOUSE- Sunset Ocean Views!
Feb. 14 – 21
$418 CAD per night
5.0 out of 5 average rating, 28 reviews
Guest favourite
Condo in Lowlands
Sint Maarten La Terrasse Maho
Oct. 19 – 26
$187 CAD per night
4.94 out of 5 average rating, 84 reviews
Guest favourite
Condo in Simpson Bay
The Beach Condo
Sep. 22 – 29
$386 CAD per night
5.0 out of 5 average rating, 49 reviews
Guest favourite
Condo in Lowlands
The Cliff in Cupecoy Beach HEAVEN!!!
Sep. 6 – 13
$298 CAD per night
5.0 out of 5 average rating, 26 reviews

Destinations to explore