
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.

Beach front luxury! Huge 2BR that has it all! 😍🤩😍
5 star hotel luxury is yours in this modern beach home! 2 guest rooms with en-suite bathrooms and deck access. Enjoy cooking your own meals and dine inside or on the deck (or beach!). Largest deck on Simpson Bay beach has it all: huge daybed, loungers, living and dining areas for your comfort and pleasure. Unwind in the den and enjoy the big screen there or in either bedroom. Your neighbor is a boutique hotel and will gladly serve you meals and drinks right to your deck! Much more info available

Oceanfront w Pool | Maho Beach area
Location , Location Location ! You can not get any closer to the ocean than in this cliff side apartment. The sound of waves crashing below and incredible ocean views from every room. The sunrise is magical everyday and by night the glowing lights of Simpson bay. This cliff side apartment has everything you need for a dream stay away from the crowds. . Just steps from 4 beaches Simpson bay, Mullet bay, burgeux bay and a 5minute walk to the world famous Maho Beach with its famous plane landings

The Loft at Simpson Bay Yacht Club
Welcome to The Loft at SBYC. Located in the heart of Simpson Bay in walking distance to the beach, great restaurants, grocery stores, shopping, salons/spas and more. In this fully renovated loft-style apartment, you will find high quality amenities throughout including a European kitchen and an amazing rainfall shower. The SBYC property offers 3 swimming pools, a hot tub, tennis courts and plenty of outdoor space for relaxing, all under 24-hour gated security. Free concierge service included.

Sint Maarten La Terrasse Maho
It's a cozy large studio with a king size bed, a queen size sleeper sofa and a big balcony, it is at the second floor at Royal Islander Club Resort La Terrasse in Maho, fully equipped and furnished. Located just in front of Maho Bay beach and few minutes walk from Mullet bay beach. There are few restaurants and boutiques like cigar shops, jewelers and beauty store. Casino Royale is right next door. There are also a supermarket for grocery shopping, a pharmacy, a clinic and more...

Maho Love Nest: Unwind by the Rooftop Pool&Hot Tub
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 for you to indulge.

Sea Loft, Breathtaking View – Private Pool
* 200 m² loft * Exceptional sea view * Private pool * 250 meters from the small beach of Galisbay * Terrace with deckchairs, garden furniture, outdoor table and BBQ * Office space * 100 Mbps WiFi * TV with thousands of channels from around the world * 250 m walk to Fort Louis de Marigot marina * 5 min walk to Marigot city center with its restaurants, shops and other stores * 5 min to the pier for Saint-Barth and Anguilla, and the taxi station

Secret View amazing apartment- Private pool
Welcome to Secret View! An elegant and intimate retreat with a private pool and a spacious terrace set directly on the lagoon. Designed for couples seeking calm, romance and discretion, just minutes from vibrant Maho with its restaurants, bars and casinos, and Mullet Bay Beach, one of the island’s finest beaches with stunning turquoise waters. Free private parking. This hidden gem is the perfect setting for unforgettable moments together.

"Blue Emerald ¤ Studio" swimming pool & fitness in Maho
Relax in this quiet and elegant tropical cocoon. All the cooking utensils for homebodies, connected TV, free wifi, Netflix activated, and also the delicious swimming pool just in front and the high-tech weight room for the most motivated. Close to the tourist centre (shopping, restaurants, bars, clubs...) and Mullet Bay beach (800 m)... Come and enjoy a modern and comfortable space, ideal for couples or solo travellers. You'll love...

Stunning Ocean View - 2 / 3 Brm Terraces Lt. Bay
Treat yourself to the stylish and modern ocean view apartment . This spacious environment, is designed to be enjoyed as a family, has a terrace with stunning sea view, climatized private pool, two master suites (one w/Japanes king bed and walking closet), the other with two double size beds (you can join them and make a king bed) and closet and a third room with daybed. All of them with their own bathroom and ocean view. Welcome!

Loft Condo - STEPS FROM BEACH!
Experience tropical luxury at our Mullet Bay vacation rental in Sint Maarten. Our 1BR loft boasts a queen bed, full kitchen, laundry facilities and a gated community complete with pool and barbecue area. Perfect for families or couples seeking a tranquil escape. Enjoy the comfort of spacious bedrooms and the convenience of on-site amenities. Book now for the ultimate island getaway!

Independent apartment at the bottom of the villa – Indigo Bay
The Villa Stella apartment welcomes you in a unique setting with spectacular views of the Caribbean Sea. Located in a 24-hour secure residence, tranquility awaits. You will be just an 8-minute walk to Indigo Bay Beach and close to shops and restaurants in the Dutch side. Composed of 2 bedrooms and 2 bathrooms, you can relax in the pool/jacuzzi overlooking the bay.

Cozy condo in Blue Pelican
Blue Pelican is a soothing sanctuary of apartments nestled around a lovely garden and zen style dipping pool. Go on, make a splash! Smart and sophisticated: for those who desire ambience and fine accommodations with a relaxed approach. The comfort, intimacy and privacy that only a small boutique property can offer. It's all in the details.
Popular amenities for Simpson Bay rentals with a pool
House rentals with a pool

Pelican key - BEACH FRONT Villa

2BR Villa w/ Lagoon View, Pool & Jacuzzi

New-Sunset Place Villa w Stunning Waterfront Views

Aman Oceanview

Luxury Bungalow with Amazing Seaview & Pool

2 Bedroom Ocean Front Villa, Private Infinity Pool

Préstige - Luxurious 3 bedroom by the Beach

Villa Monchal, 1-minute walk to the beach
Condo rentals with a pool

Villa Belharra, amazing view

Popular Beachfront Property Barefoot /Simpson bay

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

Beachfront Condo| Pool View + Private Beach Access

Sea Lover - Las Brisas (Sea Lover)

Beautiful Large 2 Bedrooms apartment in Maho

New studio with superb view of the Caribbean Sea

Brand New- Maho Condo Studio with Seaview and Pool
Other vacation rentals with a pool

Waterfront "Bonjour" Beacon Hill St Maarten

B Maho Studio

Pelican Sea View 1bdrm Maison Mazu

Infinity Ocean Edge - Luxury Oceanfront Penthouse

cosy apartment

Vacation in Paradise on the Beach

'Emerald Pearl' Studio in Maho with Full Amenities

CondoSTmaarten panoramic (Adults Only)
When is the best time to visit Simpson Bay?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $347 CAD | $372 CAD | $372 CAD | $312 CAD | $267 CAD | $273 CAD | $295 CAD | $269 CAD | $223 CAD | $212 CAD | $232 CAD | $282 CAD |
| Avg. temp | 26 °C | 26 °C | 26 °C | 27 °C | 28 °C | 29 °C | 29 °C | 29 °C | 29 °C | 29 °C | 28 °C | 27 °C |
Quick stats about vacation rentals with a pool in Simpson Bay

Total vacation rentals
Explore 220 vacation rentals in Simpson Bay

Nightly prices starting at
Simpson Bay vacation rentals start at $82 CAD per night before taxes and fees

Verified guest reviews
Over 5,590 verified reviews to help you choose

Family-friendly vacation rentals
120 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 50 rentals that welcome pets

Rentals with dedicated workspaces
100 properties have a dedicated workspace

Wifi availability
220 of Simpson Bay vacation rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Simpson Bay rentals

4.8 Average rating
Simpson Bay stays are highly rated by guests—averaging 4.8 out of 5!
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