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

Total vacation rentals
Explore 230 vacation rentals in Simpson Bay

Nightly prices starting at
Simpson Bay vacation rentals start at G$14,644 GYD per night before taxes and fees

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

Family-friendly vacation rentals
130 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
90 properties have a dedicated workspace

Wi-Fi availability
230 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!
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
ValueLocationAir conditioning

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
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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!
FamilyLocationGetting around

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.
ValueLocationAir conditioning

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.
FamilyValueCheckout

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
FamilyValueGetting around

4 Bedroom Beachfront Condo with Private Pool D2.1
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!
LocationFamilyComfort

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
ValueFamilyCheck-in

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 .
ValueFamilyPets

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.
LocationValueComfort

Stunning Ocean View - 2 / 3 Brm Terraces Lt. Bay
Treat yourself to the stylish and modern ocean view apartment . This spacious environment, is designed to be enjoyed as a family, has a terrace with stunning sea view, climatized private pool, two master suites (one w/Japanes king bed and walking closet), the other with two double size beds (you can join them and make a king bed) and closet and a third room with daybed. All of them with their own bathroom and ocean view. Welcome!
ValueFamilyCleanliness

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

ALMOND BLUE ...Pinel bay view - caribbean feeling
ValueFamilyPool

Townhouse Villa LX
LocationFamilyCheck-in

Spacious 3BR with Private Cozy Pool
LocationFamilyLaundry

Luxury Villa Turquoise Heaven in Pelican Key
FamilyValueWalkability

Designer 3BR House w Pool, Sunsets & Ocean Views
FamilyValueView

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

3 Bed 3 Bath Villa | Private Pool | Pelican | SXM
ValueLocationComfort

Slowlife! Blooming Villa! Freshly Renovated
LocationFamilyNearby
Condo rentals with a pool

Maho Love Shack:Unwind by the Rooftop Pool&Hot Tub
FamilyLocationWifi

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

Brand New- Maho Condo Studio with Seaview and Pool
LocationValueHospitality

Large 2BR Condo - STEPS FROM BEACH!
FamilyValueKitchen

Havya Cozy Stays | In Maho, Near Beaches & Airport
LocationValueKitchen

Sint Maarten La Terrasse Maho
ValueLocationDecor

Maho studio overlooking airport, Free Wi-Fi!
LocationValueNearby

The Beach Condo
ValueFamilyHospitality
Other vacation rentals with a pool

Modern 2 bedroom luxury beachside villa with pool
FamilyLocationCleanliness

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

Royal Palm Hilton SXM
ValueFamilyKitchen

Villa Ocean - Indulge Yourself in Paradise
FamilyLocationOutdoor spaces

Evasion au bord du Lagon
LocationFamilyAccess

Sea view 3BR Spring Sea Villa w/ pool, St Maarten
LocationValueNearby

CasaPisani Tranquil 2Bed condo SimpsonBayYachtClub
LocationFamilyLaundry

Escapes at the Emerald – Airport & Beach Nearby
ValueLocationNearby
When is the best time to visit Simpson Bay?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$63,596 GYD | G$61,923 GYD | G$64,224 GYD | G$56,484 GYD | G$52,090 GYD | G$48,116 GYD | G$45,187 GYD | G$41,212 GYD | G$34,099 GYD | G$34,936 GYD | G$40,794 GYD | G$60,668 GYD |
| 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 |
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