Book villas with a pool in Simpson Bay

Experience the Bliss of Private Pool Villas in Simpson Bay

Discover the ultimate retreat in Simpson Bay with luxurious villas featuring private pools. These exquisite accommodations provide the perfect blend of comfort and relaxation, allowing you to unwind in a tranquil setting while enjoying breathtaking views of the beach. Whether you’re traveling with family, embarking on a romantic getaway, or looking for a fun-filled vacation, a villa with a pool offers the space and privacy to create cherished memories together. With the soft sound of waves and the Caribbean sun overhead, your dream vacation awaits in this tropical paradise.

Our top choices for a great stay

ALMA - DIRECT BEACH ACCESS 4 BR VILLA

ALMA - DIRECT BEACH ACCESS 4 BR VILLA

Book a stay at this beach villa in Simpson Bay. Enjoy private pools, a beach locale, and a water park. Popular attractions Maho Beach and Mullet Bay Beach are located nearby.
10/10 Exceptional! (36 reviews)
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ALMA - DIRECT BEACH ACCESS 4 BR VILLA
Oceanfront amazing 2 BR Villa - 2 min from the beach

Oceanfront amazing 2 BR Villa - 2 min from the beach

Book a stay at this beach villa in Simpson Bay. Enjoy free WiFi, private pools, and a beach locale. Popular attractions Maho Beach and Mullet Bay Beach are located nearby.
8.8/10 Excellent! (53 reviews)
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Oceanfront amazing 2 BR Villa - 2 min from the beach
Pelican Key Private Luxury Villa With Panoramic View Of The Caribbean Sea

Pelican Key Private Luxury Villa With Panoramic View Of The Caribbean Sea

Book a stay at this family-friendly villa in Simpson Bay. Enjoy free WiFi, private pools, and a fitness center. Popular attractions Maho Beach and Mullet Bay Beach are located nearby.
9.4/10 Exceptional! (47 reviews)
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Pelican Key Private Luxury Villa With Panoramic View Of The Caribbean Sea
Pelikaan Sunset: A Villa With Stunning Ocean Views

Pelikaan Sunset: A Villa With Stunning Ocean Views

Book a stay at this family-friendly villa in Simpson Bay. Enjoy free WiFi, private pools, and breakfast (surcharge). Popular attractions Maho Beach and Mullet Bay Beach are located nearby.
9.8/10 Exceptional! (7 reviews)
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Pelikaan Sunset: A Villa With Stunning Ocean Views
Charming 2-bedroom villa with AC, WiFi, stunning ocean views

Charming 2-bedroom villa with AC, WiFi, stunning ocean views

Stay at this villa in Simpson Bay. Enjoy a garden, laundry facilities, and patios. Popular attractions Maho Beach and Mullet Bay Beach are located nearby.
10/10 Exceptional! (3 reviews)
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Charming 2-bedroom villa with AC, WiFi, stunning ocean views
Cliff House

Cliff House

3.5 out of 5
Stay at this 3.5-star villa in Simpson Bay. Enjoy furnished balconies, in-room washers/dryers, and an in-room coffeemaker. Popular attractions Maho Beach and Mullet Bay Beach are located nearby.
8.6/10 Excellent! (3 reviews)
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Cliff House
Villa Impala, 5 bedroom villa beachfront in Simpson Bay, Sint Maarten

Villa Impala, 5 bedroom villa beachfront in Simpson Bay, Sint Maarten

Book a stay at this beach villa in Simpson Bay. Enjoy free WiFi, private pools, and a beach locale. Popular attractions Maho Beach and Mullet Bay Beach are located nearby.
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Villa Impala, 5 bedroom villa beachfront in Simpson Bay, Sint Maarten
modern, breathtaking view of the Caribbean Sea and the island of Saba

modern, breathtaking view of the Caribbean Sea and the island of Saba

Stay at this villa in Simpson Bay. Enjoy private pools, laundry facilities, and concierge services. Popular attractions Maho Beach and Mullet Bay Beach are located nearby.
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modern, breathtaking view of the Caribbean Sea and the island of Saba
Beachfront Villa w/ pool, concierge service and airport transfers by SXMSIR

Beachfront Villa w/ pool, concierge service and airport transfers by SXMSIR

Book a stay at this beach villa in Simpson Bay. Enjoy free WiFi, private pools, and a beach locale. Popular attractions Maho Beach and Mullet Bay Beach are located nearby.
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Beachfront Villa w/ pool, concierge service and airport transfers by SXMSIR
Beautiful 6 bedroom Villa on the popular white sandy beach of Simpson bay

Beautiful 6 bedroom Villa on the popular white sandy beach of Simpson bay

Book a stay at this beach villa in Simpson Bay. Enjoy private pools, a beach locale, and laundry facilities. Popular attractions Maho Beach and Mullet Bay Beach are located nearby.
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Beautiful 6 bedroom Villa on the popular white sandy beach of Simpson bay
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.

Why choose a villa with a pool in Simpson Bay?

Opting for a luxury pool vacation villa for rent in Simpson Bay offers an unmatched experience compared to traditional hotels, especially for honeymooners, families, or leisure travelers. These private villas with swimming pools provide ample space for relaxation and recreation, allowing you to enjoy intimate moments and family gatherings without the distractions or noise of hotel environments. With a private pool at your disposal, you can take refreshing swims at your leisure, host delightful barbecues, or simply lounge by the water under the sun. Additionally, many villas boast beautiful outdoor spaces and are located in serene neighborhoods, helping you unwind after exciting days spent exploring the gorgeous beaches or indulging in local cuisine. While hotels offer their own benefits, villas stand out for their privacy, personalized experiences, and the ability to create lasting memories in a home-away-from-home atmosphere.