
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.

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.

Coco's Beach House - Simpson Bay Beach
Coco's Beach House is a stunning property just steps away from the Simpson bay beach. It will leave you feeling like you are in paradise, 2 King bedrooms with ensuite, full kitchen, 2 private patios, glittering glimpses of the beautiful turquoise ocean and all the comforts of home. It is the perfect spot for 2 couples or a family with small children. Situated in the heart of the Island, we are walking distance to some of the nicest restaurants on the island, bakery, restaurants & nightlife.

Apt2 (2 bedrooms, terrace & sea view)
Spacious and cozy duplex with 2 bedrooms and large sea-view private terrace. Located in Black Palm, an elegant residence of 6 apartments in Indigo Bay, a calm and exclusive neighborhood. Indigo Beach is just a 5-minute walk away. Shared pool with sea view. Ideal for up to 4 guests: couples, friends or families looking for relaxation. - 5 minutes’ walk from Indigo Beach - 5 minutes’ drive from the nearest supermarket - Private parking on site - Concierge service available for any request.

Aman_Aria
This unique place has a style all its own, newly built, contemporary retreat features two elegant master bedrooms, each with its own private bathroom, a spacious living area seamlessly connected to a fully equipped kitchen, an inviting outdoor terrace. Every bedroom and the living room offer uninterrupted vistas of the mesmerizing ocean. The heart of Aman is its spectacular infinity pool and sun-drenched deck, inviting you to relax while soaking in breathtaking panoramas.

Modern 2 bedroom luxury beachside villa with pool
Your own private paradise. Modern 2 bedroom luxury villa in safe gated community with security. New appliances with air conditioning, WIFI, security cameras, and secured free parking including Smart TV with free NetFlix, HBO Max, and Prime access. Private pool with adjacent outdoor dining/lounge area. Perfect for families or couples. Maid and private chef service available if needed. Walking distance from dining, night clubs, and shopping. Steps away from the beach.

VILLA JADE 1: FEET IN THE WATER/POOL SUITE
VILLA JADE is located in the bay of "FRENCH CUL DE SAC". It is a beachfront complex consisting of 3 private villas. VILLA JADE 1 is a suite for 2 people with a private pool. The villas are quiet and private... your only view is the sea. The bay of "FRENCH CUL DE SAC" is 5 minutes from ORIENT BAY, touristy with restaurants, bars, water activities, but also a few minutes from GRAND CASE, our typical little village with gourmet restaurants by the sea....

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

The Lost Paradise
Ce magnifique appartement, situé près des plages de Maho et Mullet bay et du quartier touristique de Maho, est idéal pour passer de superbes vacances. Très fonctionnel, il est parfait pour 4 personnes avec ses 2 salles de bains et sa chambre indépendante. Un lit escamotable dans le salon servira de second lit. Situé sur la presqu’île pittoresque de Point Pirouette, ce logement unique vous fera passez de merveilleux moments.

1 bedr in the middle of Simpson Bay-with Generator
This apartment is located in the best spot of the island. You have everything right at your doorstep. The beautiful pool is right at your apartment, the Beach is at 2 minutes walking and so is Market Garden Supermarket but also lots of restaurants, bakeries, bars, casinos etc. This is a perfect 1 bedroom apartment if you want to enjoy all of SXM. Add my listing to your wishlist by clicking the❤️ in the upper right corner.

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 !

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

Villa Coco

Villa Terres Basses

Slowlife! Blooming Villa! Freshly Renovated

Sunrise Over St. Barths

Blue Palm Estate Townhouse w/ Ocean View

Aquamarine, beautiful 2 bdr house, private pool!

Atypik Villa

2 Bedroom Ocean Front Villa, Private Infinity Pool
Condo rentals with a pool

CasaPisani Tranquil 2Bed condo SimpsonBayYachtClub

Oceanfront w Pool | Maho Beach area

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

Little Bay Condo with Private Pool

2BR Sunset Condo at Blue Mall – Near Maho

cosy apartment

Large 2BR Condo - STEPS FROM BEACH!

Saint Maarten La Terrasse Maho
Other vacation rentals with a pool

New beautiful sea view 2 P renovated

Waterfront "Bonjour" Beacon Hill St Maarten

Gorgeous 2 bedroom-17th floor, Fourteen Mullet Bay

Beachfront Paradise with Pool & Stunning Sunsets

Penthouse! 3-Bdr. Apartment with Stunning Views!

Villa Indigo Dream, Indigo Bay SXM

Beachfront Royal Palm 1-BR

PEACEFUL VILLA WITH POOL 5 MIN FROM THE BEACH
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.ﺇ613 | ﺩ.ﺇ716 | ﺩ.ﺇ1,065 |
| 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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