
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.

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

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.

Sint 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...

Maho Love Nest: 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.

THE HILL HOUSE, 2 Bdr, pool, panoramic view
Accommodation with private pool and breathtaking views Treat yourself to a dream break at this stylish home, nestled in the secure Almond Grove Estate neighborhood. Enjoy 2 air-conditioned bedrooms, a bright living room, a full kitchen, and especially an idyllic outdoor space with a pool and panoramic views of Simpson Bay. Just 5 min from Marigot, 10 min from the airport and 15 min from the beaches, it is the perfect address for an unforgettable stay!

Sea Loft, Breathtaking View – Private Pool
* 200 m² loft * Exceptional sea view * Private pool * 250 meters from the small beach of Galisbay * Terrace with deckchairs, garden furniture, outdoor table and BBQ * Office space * 100 Mbps WiFi * 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, shops and other stores * 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.

"Blue Emerald ¤ Studio" swimming pool & fitness in Maho
Relax in this quiet and elegant tropical cocoon. All the cooking utensils for homebodies, connected TV, free Wi-Fi, Netflix activated, and also the delicious swimming pool just in front and the high-tech weight room for the most motivated. Close to the tourist centre (shopping, restaurants, bars, clubs...) and Mullet Bay beach (800 m)... Come and enjoy a modern and comfortable space, ideal for couples or solo travellers. You'll love...

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 !

C344 - Lagoon view with balcony
C344 is a stylish 1-bedroom apartment at The Hills Residence, offering a peaceful lagoon view from a private balcony. Perfect for a relaxing getaway, it features a modern kitchen, cozy living area, and all the comforts of home. Guests can enjoy the shared pool, secure parking, and 24/7 security. Located just minutes from the beach, dining, and shopping, it’s the ideal base for exploring Sint Maarten.

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

Pelican key - BEACH FRONT Villa

2BR Villa w/ Lagoon View, Pool & Jacuzzi

New-Sunset Place Villa w Stunning Waterfront Views

Aman Oceanview

Luxury Bungalow with Amazing Seaview & Pool

2 Bedroom Ocean Front Villa, Private Infinity Pool

Préstige - Luxurious 3 bedroom by the Beach

Blu Azur : Your Dream Villa on the Lagoon
Condo rentals with a pool

"Seaduction" 2 bedroom apartment Nettle Bay

Studio COCO

Villa Belharra, amazing view

Popular Beachfront Property Barefoot /Simpson bay

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

Beachfront Condo| Pool View + Private Beach Access

Vacation in Paradise on the Beach

New studio with superb view of the Caribbean Sea
Other holiday rentals with a pool

New beautiful sea view 2 P renovated

B Maho Studio

Modern apartment with shared pool and generator

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

Sunny Outlook - 1-bdr condo - Beachfront Residence

Beachfront Royal Palm 1-BR

CondoSTmaarten panoramic (Adults Only)

The Lost Paradise
When is the best time to visit Simpson Bay?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $379 AUD | $406 AUD | $406 AUD | $340 AUD | $291 AUD | $298 AUD | $322 AUD | $294 AUD | $243 AUD | $231 AUD | $254 AUD | $307 AUD |
| 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 220 holiday rentals in Simpson Bay

Nightly prices starting at
Simpson Bay holiday rentals start at $90 AUD per night before taxes and fees

Verified guest reviews
Over 5,590 verified reviews to help you choose

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

Pet-friendly accommodation
Find 50 rentals that welcome pets

Rentals with dedicated workspaces
100 properties have a dedicated workspace

Wi-Fi availability
220 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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