
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

Popular Beachfront Property Barefoot /Simpson bay
This Beautiful Beachfront condo in Sint Maarten, Barefoot, is like being on your own little island. 1 min. to shore. The beautiful crystal blue ocean waters you can see and hear from every corner of this condo. This Oasis has such beauty. Mostly private with pure tranquility. . A constant breeze as you open up the doors and windows to let the sea air open up your senses. 8 minute drive from the Dutch airport 16 minutes walking distance from main restaurants casinos and live entertainment.

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.

Maho studio overlooking airport, Free Wi-Fi!
Welcome to "Flight Deck", a cozy and unique studio apartment overlooking the Princess Juliana International Airport & runway and beautiful Simpson Bay Beach. This unit is in a prime location, as it is just a 5 minute walk to the heart of Maho Village, which is full of shops, restaurants, bars, nightclubs, casinos, and the world famous Maho Beach, where thrill-seekers can stand just feet below planes as they land and experience the thrilling sensation of the jet blast of planes taking off.

Gorgeous 2 bedroom-17th floor, Fourteen Mullet Bay
For an unforgettable stay in paradise, choose our beautifully furnished 2 bedroom, 2.5 bathroom condo, with its panoramic breathtaking view over Mullet Bay beach, the golf court and the lagoon. Located on the 17th floor of Fourteen in Mullet Bay, with direct access to the beach. Enjoy the tranquility and great comfort offered, while being 5 minutes away from the airport, with several restaurants, bars, casinos and shops close by. Everything was carefully thought to exceed your expectations.

Sea Loft Vue imprenable - piscine privée
* Loft de 200m² * Vue mer exceptionnelle * Piscine privée * A 250 mètres de la petite plage de Galisbay * Terrasse avec chaises longues, salon de jardin, table d'extérieur et BBQ * Espace bureau * Wifi 100 Mbps * TV avec milliers de chaines du monde entier * A 250 m à pied de la marina Fort Louis de Marigot * A 5 min à pied du centre ville de Marigot avec ses restaurants, boutiques et autres commerces * A 5 min de l'embarcadère pour Saint-Barth et Anguilla, et de la station de taxis

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.

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.
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

Sunrise Over St. Barths

Townhouse Villa LX

New-Sunset Place Villa w Stunning Waterfront Views

Luxury Bungalow with Amazing Seaview & Pool

*NEW* SeaSun New Home with Private Pool

Préstige - Luxurious 3 bedroom by the Beach
Condo rentals with a pool

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

Studio COCO

Studio «SeaBird» les pieds dans l’eau sur la plage

Vacances au Paradis sur La Plage

The Beach Condo

Large 2BR Condo - STEPS FROM BEACH!

'Emerald Pearl' Studio in Maho with Full Amenities

Villa Bora Bora - Beach and Caribbean Sea
Other vacation rentals with a pool

Pelican Sea View 1bdrm Maison Mazu

Nouveau un Paradis sur la plage !

Brand new! - Slowlife - Enjoy Villa

Ocean Dream Villa

SEA TRUE VILLA,Lavish,Sea view near Maho&Mulletbay

Aman Oceanview

Cozy condo in Blue Pelican

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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