
Holiday rentals with a pool in Simpson Bay
Find and book unique homes with a pool on Airbnb
Quick stats about holiday rentals with a pool in Simpson Bay

Total holiday rentals
Explore 230 holiday rentals in Simpson Bay

Nightly prices starting at
Simpson Bay holiday rentals start at £52 per night before taxes and fees

Verified guest reviews
Over 5,620 verified reviews to help you choose

Family-friendly holiday rentals
130 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
90 properties have a dedicated workspace

Wifi availability
230 of Simpson Bay holiday rentals include wifi 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!
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
4.96 out of 5 average rating, 109 reviews
Endless Views @ Acqua Bleu
Nestled in the heart of Saint Martin, Acqua Bleu offers breathtaking views of turquoise waters and pristine beaches. You'll have direct access to some of the most gorgeous spots on the island, ensuring endless fun in the sun. You’ll enjoy access to various amenities, including a fully equipped kitchen, spacious living areas, a refreshing swimming pool, and much more! Acqua Bleu features two king bedrooms, each accompanied by a private bathroom. Get ready to enjoy a truly rejuvenating vacation!
4.99 out of 5 average rating, 107 reviews
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.
5.0 out of 5 average rating, 84 reviews
Horizon (Apt3) – Sea & Pool View, Terrace
Stylish triplex with 3 bedrooms, all with sea and pool view. Located in Black Palm, an elegant residence of 7 apartments in Indigo Bay, a calm and exclusive neighborhood. Indigo Beach is just a 5-minute walk away. Enjoy the shared pool with sea view. Ideal for up to 5 guests: couples, friends or families looking for relaxation. - 5 minutes’ walk from Indigo Beach - 5 minutes’ drive from the nearest supermarket - Private parking on site - Concierge service available for any request.
4.81 out of 5 average rating, 103 reviews
4 Bedroom Beachfront Condo with Private Pool C2.1
Welcome to Kim Sha Beach Front apartment where amazing memories are made! Location is our shining spot! Just mins walking to the beach and located in the busiest area! Surrounded by bars and popular restaurants with local and international food, spas, shops and casinos! Walking distance to Simpson Bay Marina where you have departures to different islands with numerous boat charter and water sports activities. The location assures that you will have an unforgettable holiday!
4.86 out of 5 average rating, 22 reviews
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.
4.91 out of 5 average rating, 259 reviews
Waterfront "Bonjour" Beacon Hill St Maarten
This stunning 4-bedrooms, 4 bathrooms villa overlooks Maho Bay and provides a front row seat to beautiful SXM sunsets, and over the famous Maho Beach. Enjoy the views while taking a dip in the home’s infinity pool overlooking the ocean or from its multiple outdoor dining and seating options conveniently and securely located minutes from restaurants, bars, nightlife, Maho Market and more, steps away from direct beach access to Simpson Bay Beach. Back up Diesel Generator
4.97 out of 5 average rating, 92 reviews
Serenity Seascape | 2BR Retreat, 270° Oceanviews
Wake up to a jaw-dropping panoramic view of the Caribbean Sea from this chic oceanfront gem in Point Blanche! Bask in 270° views, picture-perfect sunrises, and views of St. Barths from your own private terrace. The space features modern coastal interiors and hotel-quality bathrooms, blending luxury with cliffside serenity. Located just five minutes from Philipsburg, it offers easy access to beaches, restaurants, and shopping while preserving tranquility.
5.0 out of 5 average rating, 11 reviews
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
5.0 out of 5 average rating, 202 reviews
Stunning oceanfront condo
Unit 1201 in Tower A: Enjoy spacious luxury accommodations for the whole family at this stylish place only minutes from the airport and steps from the famous Mullet Bay Beach. Two spacious bedrooms each with ocean views and 2.5 bathrooms. Take advantage of the fully furnished well appointed kitchen, free gym and free large heated pool with its own restaurant/bar. Stunning panoramic views of the ocean, beach, mountains, and the golf course.
4.98 out of 5 average rating, 40 reviews
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 !
4.99 out of 5 average rating, 189 reviews
Préstige - Luxurious 3 bedroom by the Beach
Nestled on the hills of Indigo Bay, Préstige is located midway between Philipsburg and the Simpson Bay touristic hangout. Préstige exudes relaxation the minute you walk through the door, elegant and distinguished! The 3-bedroom spacious residence sleeps six! Overlooking Indigo Beach with private swimming pool! Caribbean living, yours to enjoy!
4.83 out of 5 average rating, 215 reviewsPopular amenities for Simpson Bay rentals with a pool
House rentals with a pool

ALMOND BLUE ...Pinel bay view - caribbean feeling
4.89 out of 5 average rating, 100 reviews
Blue mornings, swimming pool, superb view
4.9 out of 5 average rating, 104 reviews
Sweet Home on the Beach rdc
5.0 out of 5 average rating, 8 reviews
Townhouse Villa LX
4.81 out of 5 average rating, 26 reviews
Designer 3BR House w Pool, Sunsets & Ocean Views
4.88 out of 5 average rating, 41 reviews
Spacious 3BR with Private Cozy Pool
5.0 out of 5 average rating, 61 reviews
Stunning Panoramic Views Of The Ocean & St Barth!
5.0 out of 5 average rating, 47 reviews
SeaRenity Villa With Private Pool Indigo Bay
4.97 out of 5 average rating, 37 reviewsApartment rentals with a pool

Oceanfront w Pool | Maho Beach area
4.8 out of 5 average rating, 192 reviews
Brand New- Maho Condo Studio with Seaview and Pool
4.98 out of 5 average rating, 120 reviews
"SeaBird" studio, feet in the water on the beach
4.96 out of 5 average rating, 155 reviews
Havya Cozy Stays | In Maho, Near Beaches & Airport
4.9 out of 5 average rating, 132 reviews
Maho studio overlooking airport, Free Wi-Fi!
4.82 out of 5 average rating, 102 reviews
Large 2BR Condo - STEPS FROM BEACH!
4.81 out of 5 average rating, 139 reviews
Saint Maarten La Terrasse Maho
4.95 out of 5 average rating, 143 reviews
Beachfront Ultra Luxury Modern Condo / Beach Views
4.96 out of 5 average rating, 24 reviewsOther holiday rentals with a pool

SEA TRUE VILLA,Lavish,Sea view near Maho&Mulletbay
4.77 out of 5 average rating, 154 reviews
Modern 2 bedroom luxury beachside villa with pool
4.87 out of 5 average rating, 89 reviews
Aman_Aria
4.98 out of 5 average rating, 47 reviews
Royal Palm Hilton SXM
4.93 out of 5 average rating, 67 reviews
Escapes at the Emerald – Airport & Beach Nearby
4.93 out of 5 average rating, 28 reviews
Luxurious Hidden Pearl - Private Pool
5.0 out of 5 average rating, 27 reviews
AZUR 4BR 4.5BA Walk to Indigo Beach- Sea Side Dr.
4.83 out of 5 average rating, 18 reviews
Sunny Marina Residence
4.84 out of 5 average rating, 31 reviewsWhen is the best time to visit Simpson Bay?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £227 | £221 | £230 | £202 | £186 | £172 | £162 | £147 | £122 | £125 | £146 | £217 |
| 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 |
Destinations to explore
- Family-friendly rentals Simpson Bay
- Beach apartment rentals Simpson Bay
- Pet-friendly rentals Simpson Bay
- Rentals with beach access Simpson Bay
- Flat rentals Simpson Bay
- Rentals with a hot tub Simpson Bay
- Apartment rentals Simpson Bay
- House rentals Simpson Bay
- Serviced apartment rentals Simpson Bay
- Villa rentals Simpson Bay
- Beachfront rentals Simpson Bay
- Waterfront rentals Simpson Bay
- Rentals with pools Sint Maarten





