
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.

Luxury Villa Turquoise Heaven in Pelican Key
Welcome to Villa Turquoise Heaven- Modern Luxury in Pelican Key, SXM Experience the pinnacle of Caribbean elegance at Villa Turquoise Heaven, the newest luxury villa in the exclusive Tepui Residence. Designed for relaxation and style, this modern retreat offers a seamless blend of indoor-outdoor living with unparalleled views of the turquoise Caribbean Sea. From waking up to the gentle sound of waves to savoring sunsets from your private infinity pool, Villa TH offers an unforgettable escape.

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

Beachfront Escape with Pool & Stunning Sunsets
Escape to a beachfront paradise with a pool and stunning sunsets. Wake up to the soothing sound of ocean waves and lounge on the private patio overlooking turquoise waters. Step onto white sandy beaches with direct access, or stroll to nearby restaurants and vibrant nightlife. Your coastal sanctuary offers unforgettable moments of relaxation and tranquility. Designed for comfort and convenience, the community and unit include: • Ocean-view pool • Elevator access • Full-building generator

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.

Saint 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...

Sunny Outlook - 1-bdr condo - Beachfront Residence
✨ Sunny Outlook with IRE Vacations ✨ This amazing 1 bedroom 1.5 bathroom unit is located at Palm Beach Condo’s, directly on Simpson Bay Beach. Palm beach is very convenient located in Simpson Bay, here you will find beach bars, restaurants and supermarkets within walking distance. Only a 10 minute drive from the airport. Palm beach offers you a large common pool and private access to the beach. Enjoy your day on the beach, at the pool or go on an adventure on our beautiful island!

Maho Love Shack: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.

Beachfront Royal Palm 1-BR
This one-bedroom unit is located on the 4th floor of the Royal Palm Hilton Vacation Club in Simpson Bay, St Maarten. This property boasts direct beach access and stunning ocean views! Inside you’ll find a spacious open-plan living area with a pull out sofa, and the modern kitchen is fully equipped. Situated in the heart of it all, close to restaurants, bars & nightlife! Please note: The Royal Palm requires a $250 refundable security deposit at check-in.

Sea Loft, Breathtaking View – Private Pool
* 200 m² loft * Exceptional sea view * Private pool * 250 meters from the small beach of Galisbay * Terrace with lounge chairs, garden furniture, outdoor table and BBQ * Office area * 100 Mbps Wi-Fi * 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, boutiques and other shops * 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.

Stunning Sea View – 1min Walk to the Beach & pool
Wake up to the endless blue of the Caribbean from your private terrace with breathtaking sea views. This beachfront apartment in Baie Nettle combines comfort, elegance, and serenity. Direct beach access, 4 pools, 2 tennis courts, Wi-Fi, A/C, and fully equipped kitchen. Ideally located between the French and Dutch sides, near top beaches and restaurants. A perfect escape for couples, remote workers, or anyone seeking peace.

New, a dream on the beach!
Villa "Malaka" is located in a unique and quiet complex called Nettlé Bay Beach Club, 4 swimming pools, 2 tennis courts, secure parking, breathtaking sea views, ideally located on Nettlé Bay between the French and Dutch sides, close to useful amenities: supermarket, bakery, 4 restaurants, water sports. The "Malaka" villa can accommodate up to 4 people, it will be the ideal place for a dream stay by the water.
Popular amenities for Simpson Bay rentals with a pool
House rentals with a pool

Pelican key - BEACH FRONT Villa

Sunrise Over St. Barths

Slowlife! Blooming Villa! Freshly Renovated

Blue Palm Estate Townhouse w/ Ocean View

Modern Bungalow with Stunning Seaview & Pool

Townhouse Villa LX

2 Bedroom Ocean Front Villa, Private Infinity Pool

*NEW* SeaSun New Home with Private Pool
Condo rentals with a pool

CasaPisani Tranquil 2Bed condo SimpsonBayYachtClub

The Cliff in Cupecoy Beach HEAVEN!!!

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

cosy apartment

Large 2BR Condo - STEPS FROM BEACH!

'Emerald Pearl' Studio in Maho with Full Amenities

Casa Nova, Indigo Bay SXM

Mullet Bay Suite 802 - Your luxury vacation in SXM
Other vacation rentals with a pool

Ocean Dream Villa

Indigo Bay Villa Poolside - Ocean 14

Apartment TalyJay

Simpson Bay Beach 3 Bedroom with pool

CondoSTmaarten panoramic (Adults Only)

Seaside : very cosy condo for 4

Sea view 3BR Spring Sea Villa w/ pool, St Maarten

Private Pool- 5 min DRIVE to Maho Beach & Airport
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 | $228 CAD | $267 CAD | $397 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 210 vacation rentals in Simpson Bay

Nightly prices starting at
Simpson Bay vacation rentals start at $109 CAD per night before taxes and fees

Verified guest reviews
Over 4,510 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
90 properties have a dedicated workspace

Wifi availability
210 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!
Destinations to explore
- San Juan Vacation rentals
- Carolina Vacation rentals
- Culebra Vacation rentals
- Sainte-Anne Vacation rentals
- Saint Thomas Vacation rentals
- Saint Croix Vacation rentals
- Aguadilla Vacation rentals
- Little Saint James Vacation rentals
- Basse-Terre Island Vacation rentals
- Tortola Vacation rentals
- Fort-de-France Vacation rentals
- Le Gosier Vacation rentals
- Pet-friendly rentals Simpson Bay
- Rentals with a patio Simpson Bay
- Apartment rentals Simpson Bay
- Family-friendly rentals Simpson Bay
- Condo rentals Simpson Bay
- Beach condo rentals Simpson Bay
- Rentals with beach access Simpson Bay
- Rentals with a washer and dryer Simpson Bay
- House rentals Simpson Bay
- Rentals with outdoor seating Simpson Bay
- Beachfront rentals Simpson Bay
- Waterfront rentals Simpson Bay
- Fitness-friendly rentals Simpson Bay
- Smoking-friendly rentals Simpson Bay
- Villa rentals Simpson Bay
- Rentals with a hot tub Simpson Bay
- Serviced apartment rentals Simpson Bay
- Rentals with pools Sint Maarten




