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Vacation 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.

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Top guest favorite
A spacious daybed is shaded by a wooden pergola, surrounded by vibrant greenery. The beach and ocean serve as a backdrop, with gentle waves lapping at the shore. Colorful cushions and a soft blanket add comfort, while a small Buddha statue creates a serene ambiance.
Condo in Simpson Bay
4.97 out of 5 average rating, 106 reviews

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

Top guest favorite
The private patio features a saltwater pool with ocean views, complemented by lounge chairs and tropical plants. Soft clouds drift overhead, enhancing the serene atmosphere. Nearby, a dining area offers an inviting space for meals while overlooking the lush garden and the expansive sea.
Home in Cole Bay
4.89 out of 5 average rating, 38 reviews

Luxury Villa Turquoise Heaven in Pelican Key

Welcome to Villa Turquoise Heaven- Modern Luxury in Pelican Key, SXM Experience the pinnacle of Caribbean elegance at Villa Turquoise Heaven, the newest luxury villa in the exclusive Tepui Residence. Designed for relaxation and style, this modern retreat offers a seamless blend of indoor-outdoor living with unparalleled views of the turquoise Caribbean Sea. From waking up to the gentle sound of waves to savoring sunsets from your private infinity pool, Villa TH offers an unforgettable escape.

Guest favorite
Condo in Simpson Bay
4.88 out of 5 average rating, 8 reviews

Deep Blue Sea at LaSiesta - Oceanfront Condo

This stunning beach front / poolside ground floor 1 bedroom condo was completely renovated August 2025! Deep Blue Sea is an immaculate and well appointed luxury property centrally located in Simpson Bay right on the sparkling waters of Simpson Bay Beach. Nearly everything in this condo is brand new and updated in a chic & modern beach style with all the amenities and comforts of a luxury resort, but without the crowds or bustle that go with it. Peace, privacy, pool and the Deep Blue Sea...

Top guest favorite
A bright living area features large glass doors that open to a private outdoor space. A comfortable sofa and a coffee table are positioned on a light-toned rug. A TV is mounted on a sleek white cabinet, while wooden accents add warmth to the design.
Apartment in Simpson Bay
5 out of 5 average rating, 76 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.

Guest favorite
Apartment in Pelican
5 out of 5 average rating, 18 reviews

Luxurious Hidden Pearl - Private Pool

This luxurious studio has been remodeled in 2025 and is ready for guests seeking a stylish studio with pool. The room has a brand-new kitchen and bathroom and has everything you might need during your vacation. Enjoy the private saltwater pool and relax on the deck on the lounge chairs and comfortable seating areas. The outdoor space is beautifully set up and we offer a BBQ if you like a home cooked meal. The gorgeous tropical garden and breathtaking ocean views complete the experience.

Guest favorite
A spacious terrace offers a stunning view of the sea and distant coastline, featuring a glass railing. A dining table and woven chairs are positioned on the tiled floor. Lush greenery is present in a planter, contributing to the serene atmosphere.
Condo in Sint Maarten
4.87 out of 5 average rating, 45 reviews

Apt2 (2 bedrooms, terrace & sea view)

Spacious and cozy duplex with 2 bedrooms and large sea-view private terrace. 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. Shared pool with sea view. Ideal for up to 4 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.

Top guest favorite
An outdoor terrace features comfortable white lounge furniture arranged around a coffee table. Sun loungers are positioned beside a private infinity pool, overlooking the ocean and distant boats. The scene is framed by tropical plants and a clear blue sky, enhancing the serene coastal environment.
Loft in Marigot
4.99 out of 5 average rating, 192 reviews

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

Top guest favorite
Condo in Les Terres Basses
4.98 out of 5 average rating, 65 reviews

Starfruit Condo with ocean view in Kombawa Domaine

Discover our Kombawa Bungalow with its breathtaking sea view! The peace and quiet and the sound of birdsong will help you recharge your batteries! The exclusive Baie aux Prunes beach is just a few minutes' walk away, where you can enjoy peaceful swims in turquoise waters! The bedroom with a quality hotel mattress and bathroom are spacious and contemporary, opening onto a pleasant terrace, ideal for watching the sunset. A change of scenery and unforgettable emotions guaranteed!

Guest favorite
The living area features a spacious sectional sofa arranged around a woven coffee table. A television sits on a mid-century modern wooden console, complemented by a potted cactus. Floor-to-ceiling windows provide expansive views of the beach and coastline.
Apartment in Cupecoy Beach
5 out of 5 average rating, 33 reviews

B-1602 Luxury two bedroom unit oceanview with balc

Welcome to our luxurious two-bedroom apartment, situated on the 16th floor and offering a seamless blend of elegance, comfort, and breathtaking beach views. Prepare to immerse yourself in a world of opulence and tranquility, where every detail has been meticulously designed to create an extraordinary coastal retreat.<br><br>As you step into the apartment, you'll be immediately captivated by the stunning beach view that greets you through the floor-to-ceiling windows.

Top guest favorite
A panoramic ocean view is captured from the terrace featuring a private heated pool. The crystal-clear water of the pool reflects sunlight, while the vast sea and distant islands are visible under a bright blue sky with scattered clouds.
Apartment in Little Bay
4.95 out of 5 average rating, 152 reviews

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!

Guest favorite
A private swimming pool with a clear blue surface is visible on a spacious terrace. Lush palm trees and ocean views create a vibrant backdrop, while lounge chairs are placed on the deck. The surrounding area is well-maintained and features a bright, sunny atmosphere.
Guesthouse in Cole Bay
4.91 out of 5 average rating, 53 reviews

New ! Apartment with pool and ocean view #1

Newly renovated apartment with swimming pool and ocean view. Ideally located in Pelican Key, next to the beach, restaurants, groceries, bars, casinos, clubs, next to Simpson Bay and close to the airport. This apartment, "Aruba", is part of Ruby Blue Residence with 5 other independent apartments, swimming pool, garden, laundry with washer and dryer, private free parking. Enjoy your vacation in our peaceful place ! Adults only

Top guest favorite
A spacious terrace is furnished with a wooden dining table surrounded by black wicker chairs. Lush greenery and the lagoon are visible beyond the railing, with palm trees swaying gently in the breeze. The sky is bright blue with scattered clouds.
Apartment in Simpson Bay
5 out of 5 average rating, 29 reviews

Vitamin sea 2

Welcome to Vitamin Sea 2 ! This one bedroom condo is well located in Simpson Bay Yacht club, central location in the heart of the action, and nonetheless peaceful atmosphere, tucked away by lush yet elegant landscaping and architecture. The living room and the master bedroom have an amazing view over the lagoon, offering a fresh respite from the town of Simpson Bay. 24/7 security gated residence, swimming pool, parking.

Popular amenities for Simpson Bay rentals with a pool

When is the best time to visit Simpson Bay?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$63,613 GYDG$61,939 GYDG$64,241 GYDG$47,710 GYDG$40,805 GYDG$41,851 GYDG$45,199 GYDG$41,223 GYDG$34,108 GYDG$34,945 GYDG$40,805 GYDG$60,684 GYD
Avg. temp26°C26°C26°C27°C28°C29°C29°C29°C29°C29°C28°C27°C

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$12,555 GYD per night before taxes and fees

  • Verified guest reviews

    Over 5,080 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!