
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 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!

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.

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.

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 !

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

Pelican key - BEACH FRONT Villa

Sunrise Over St. Barths

Blue Palm Estate Townhouse w/ Ocean View

Townhouse Villa LX

New-Sunset Place Villa w Stunning Waterfront Views

Luxury Bungalow with Amazing Seaview & Pool

*NEW* SeaSun New Home with Private Pool

LODGE Elegant Cocoon, Tropical Terrace, Sea View
Condo rentals with a pool

Villa Belharra, amazing view

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

Luxury Condo "The Q" + Huge Pool Patio + Beach/Bar

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

cosy apartment

Large 2BR Condo - STEPS FROM BEACH!

'Emerald Pearl' Studio in Maho with Full Amenities

Stylish Maho Condo w/ Pool | Walk to Everything!
Other holiday rentals with a pool

CasaPisani Tranquil 2Bed condo SimpsonBayYachtClub

NEW! Orient Bay's best view 2 bedrooms 2 bathrooms

Ocean Dream Villa

Azure Heaven, Breathtaking views, Pool, Gym, Maho

Simpson Bay Beach 3 Bedroom with pool

CondoSTmaarten panoramic (Adults Only)

Seaside : very cosy condo for 4

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 | $420 NZD | $450 NZD | $450 NZD | $377 NZD | $323 NZD | $331 NZD | $358 NZD | $326 NZD | $270 NZD | $276 NZD | $323 NZD | $480 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 $132 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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