
Holiday 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

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 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.

Beacon Hill Hideaway: Luxury Condo in Simpson Bay
Escape to luxury at Beacon Hill Hideaway, a modern beachfront condo overlooking Simpson Bay Beach. This spacious 2-bedroom property features stunning ocean views, elegant modern interiors, and direct beach access. Enjoy a covered terrace, private gated entry, and proximity to vibrant Maho nightlife. With high-end finishes, ample amenities, and the beach at your doorstep, it’s the perfect Sint Maarten getaway for families, couples, or friends. Book today and experience Caribbean paradise!

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!

B-702 Stunning Ocean view corner unit
Welcome to Fourteen at Mullet Bay, one of the most exquisite and luxurious beachfront residence in St Maarten located directly on the famous Mullet Bay beach and golf course. <br><br>Welcome to our luxurious one bedroom apartment, situated on the seventh floor and boasting captivating views of the pristine beach. Prepare to immerse yourself in a haven of opulence and tranquility, where every detail has been meticulously curated to provide an unparalleled coastal retreat.<br><br>

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.

Appartement indépendant bas de villa - Indigo Bay
L'appartement de la Villa Stella vous accueille dans un cadre unique avec une vue spectaculaire sur la mer des Caraïbes. Située dans une résidence sécurisée 24h/24, la tranquillité est au rendez-vous. Vous serez à seulement 8 min à pied de la plage d'Indigo Bay et proche des commerces et restaurants de la partie néerlandaise. Composée de 2 chambres et de 2 salles de bain, vous pourrez vous détendre dans la piscine/jacuzzi surplombant la baie .

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.

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

Pelican key - BEACH FRONT Villa

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

Sunrise Over St. Barths

Blue Palm Estate Townhouse w/ Ocean View

Modern Bungalow with Stunning Seaview & Pool

Townhouse Villa LX

*NEW* SeaSun New Home with Private Pool

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

Loft Condo - STEPS FROM BEACH!

Villa Belharra, amazing view

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

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

cosy apartment

'Emerald Pearl' Studio in Maho with Full Amenities

Villa Bora Bora - Beach and Caribbean Sea

Sint Maarten La Terrasse Maho
Other holiday rentals with a pool

"Black Pearl"

Ocean Dream Villa

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

Simpson Bay Beach 3 Bedroom with pool

CondoSTmaarten panoramic (Adults Only)

Seaside : very cosy condo for 4

Love beach loft

Studio Ocean Front, Infinity 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 | $421 NZD | $451 NZD | $451 NZD | $378 NZD | $323 NZD | $332 NZD | $358 NZD | $327 NZD | $270 NZD | $277 NZD | $323 NZD | $481 NZD |
| 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 holiday rentals with a pool in Simpson Bay

Total holiday rentals
Explore 210 holiday rentals in Simpson Bay

Nightly prices starting at
Simpson Bay holiday rentals start at $133 NZD per night before taxes and fees

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

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

Pet-friendly accommodation
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
90 properties have a dedicated workspace

Wi-Fi availability
210 of Simpson Bay holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi 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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