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Our top choices for Orient Bay condo rentals

Sunny Days at Simpson Bay Yacht Club
Sunny Days at Simpson Bay Yacht ClubSimpson Bay
10.0 out of 10, Exceptional, (2)
$1,023 nightly
The price is $1,068
Jan 16 - Jan 17, 2026
Total with taxes and fees

Oceanview Escape in Sint Maarten
Oceanview Escape in Sint MaartenPelican Key
$676 nightly
The price is $706
Jan 1 - Jan 2, 2026
Total with taxes and fees

2 BR 2 BA, beachfront condo, amazing oceanview, private beach access
2 BR 2 BA, beachfront condo, amazing oceanview, private beach accessSimpson Bay
9.4 out of 10, Exceptional, (16)
$502 nightly
The price is $520
Jan 26 - Jan 27, 2026
Total with taxes and fees

Beacon Hill Hideaway: Luxury Condo in Simpson Bay
Beacon Hill Hideaway: Luxury Condo in Simpson BaySimpson Bay
$706 nightly
The price is $738
Jan 28 - Jan 29, 2026
Total with taxes and fees

Maho Beach Modern 1-Bedroom, Ocean Level
Maho Beach Modern 1-Bedroom, Ocean LevelMaho
9.4 out of 10, Exceptional, (3)
$269 nightly
The price is $269
Jan 29 - Jan 30, 2026
Total with taxes and fees

Prime Maho 1BR w/ Pool | Front Row to the Action!
Prime Maho 1BR w/ Pool | Front Row to the Action!Simpson Bay
$267 nightly
The price is $279
Jan 20 - Jan 21, 2026
Total with taxes and fees

Maho Beach House - Petit Studio Océanique - Charmante Vue
Maho Beach House - Petit Studio Océanique - Charmante VueMaho, Sint Maarten
9.0 out of 10, Wonderful, (2)
$401 nightly
The price is $401
Jan 1 - Jan 2, 2026
Total with taxes and fees

Maho Beach House: Elegant 1-Bedroom, Beach Level
Maho Beach House: Elegant 1-Bedroom, Beach LevelSimpson Bay
$439 nightly
The price is $439
Jan 7 - Jan 8, 2026
Total with taxes and fees
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Orient Bay Hotel Reviews

La Playa Orient Bay
10/10 Excellent
Find out more about Orient Bay
Orient Bay Condo Rentals information
Number of reviews | 31 |
|---|---|
Accommodation | 32 Condo Rentals |
Lowest Price | $269 |
Highest Price | $1,068 |
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