
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.

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 Beach Condo
The Beach Condo, located in Palm Beach Apt. complex is a completely newly renovated 2 bedroom condo right on Simpson Bay Beach. Equipped with all amenities, this is your ideal tropical luxurious getaway. A brand new, fully equipped kitchen, large living and dining area and two king size bed-bedrooms with individual bathrooms give you all the space you need for a retreat in the Caribbean. Lounge on the porch, swim in the pool or live it up on the beach, it's all right there for you to enjoy.

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.

"SeaBird" studio, feet in the water on the beach
The "SeaBird studio" is ideally located with a beautiful view of the Caribbean Sea and an idyllic beach just for you! It offers plenty of comfort and storage with refined and original decoration. The residence is perfectly secure with a large swimming pool and tropical garden. Everything is within walking distance: grocery store, local market, shops, traditional or gourmet restaurants, ferry station to other islands, etc... High-speed Wi-Fi and TV Europe and America.

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 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 !

Royal Palm Hilton SXM
This beautiful 2-bedroom 2-bathroom condo is in the heart of Simpson Bay, located inside the Royal Palm Hilton Vacation Club, and offers full resort amenities including a swimming pool, direct beach access, and a gym. This fourth-floor units has dazzling sunset views. Wake up to the beautiful view and then head downstairs where all you have to do is choose between the beach or the pool.

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!
Popular amenities for Simpson Bay rentals with a pool
House rentals with a pool

Ocean View Villa-Indigo Bay W/Private Pool/0 Steps

Pelican key - BEACH FRONT Villa

Slowlife! Blooming Villa! Freshly Renovated

Sunrise Over St. Barths

Luxury Bungalow with Amazing Seaview & Pool

Paradise View, Creole house with private pool

Préstige - Luxurious 3 bedroom by the Beach

Teresa’s Ocean Paradise
Condo rentals with a pool

Royal Palm-5th floor-Amazing OceanViews-1 Bedroom

Popular Beachfront Property Barefoot /Simpson bay

Beachfront Condo| Pool View + Private Beach Access

Vacation in Paradise on the Beach

Brand New- Maho Condo Studio with Seaview and Pool

'Emerald Pearl' Studio in Maho with Full Amenities

Studio on the water in the Simpson Bay Yacht Club

Sunshine Apartment right on the beach
Other vacation rentals with a pool

Luxury Seafront Apartment & Panoramic Sea Views

B Maho Studio

Pelican Sea View 1bdrm Maison Mazu

Studio - Simpson Bay Yacht Club

Aman Oceanview

Apartment TalyJay

Green Balaou 15 min à pied Orient-Bay

Simpson Bay Beach 3 Bedroom with pool
When is the best time to visit Simpson Bay?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ933 | ﺩ.ﺇ999 | ﺩ.ﺇ999 | ﺩ.ﺇ837 | ﺩ.ﺇ716 | ﺩ.ﺇ735 | ﺩ.ﺇ793 | ﺩ.ﺇ723 | ﺩ.ﺇ599 | ﺩ.ﺇ569 | ﺩ.ﺇ624 | ﺩ.ﺇ757 |
| 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 ﺩ.ﺇ294 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 & kid-friendly amenities

Pet-friendly vacation rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
90 properties have a dedicated workspace

Wi-Fi availability
210 of Simpson Bay vacation rentals include wi-fi 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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