
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, quiet and pure tranquility. A constant breeze as you open up the doors and windows to let the sea air open up your senses. 8 minutes from the Dutch airport 16 minutes walking distance from main restaurants casinos and live entertainment.

Teresa’s Ocean Paradise
St. Maarten’s best kept secret with breathtaking ocean views from every room! Step into Teresa’s Ocean Paradise where you’ll wake up to panoramic views of turquoise water. Nestled in a private gated community with a communal pool overlooking the ocean, fully equipped kitchen, and two king bedrooms – each with private bathrooms. Perfectly located to enjoy the best of the Dutch and French side’s beaches and restaurants. A one-of-a-kind property to make your vacation an unforgettable retreat.

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.

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.

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.

A-1701 Stunning oceanfront two bedrooms
Welcome to our exquisite luxury two-bedroom corner apartment, perched on the 17th floor and offering a breathtaking vantage point overlooking the beach. Prepare to indulge in a world of beauty, comfort, and sophistication, where every detail has been carefully curated to create an extraordinary coastal retreat.<br><br>As you enter the apartment, you'll be immediately captivated by the stunning panoramic views of the beach through the floor-to-ceiling windows.

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

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

Townhouse Villa LX

New-Sunset Place Villa w Stunning Waterfront Views

SeaRenity Villa With Private Pool Indigo Bay

Luxury Bungalow with Amazing Seaview & Pool

2 Bedroom Ocean Front Villa, Private Infinity Pool

LODGE Elegant Cocoon, Tropical Terrace, Sea View

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

Villa Belharra, amazing view

2BR Beachfront Bliss in Simpson Bay - Encanto

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

Maho 1 Bed Condo with ocean view & Free Wi-Fi

Vacation in Paradise on the Beach

Apt5 (2 bedrooms, terrace & sea view)

Large 2BR Condo - STEPS FROM BEACH!

Saint Maarten La Terrasse Maho
Other vacation rentals with a pool

Waterfront Studio, Bay Nettley, Saint-Martin

Brand new! - Slowlife - Enjoy Villa

NEW 1BR apt lagoon & sunset view 2/3p

Ocean Dream Villa

Aman Oceanview

CondoSTmaarten panoramic (Adults Only)

Seaside : very cosy condo for 4

The Emerald at Maho
When is the best time to visit Simpson Bay?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | € 218 | € 234 | € 234 | € 196 | € 168 | € 172 | € 186 | € 169 | € 140 | € 133 | € 146 | € 177 |
| 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 € 52 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 & kid-friendly amenities

Pet-friendly vacation rentals
Find 50 rentals that welcome pets

Rentals with dedicated workspaces
100 properties have a dedicated workspace

Wi-Fi availability
220 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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