
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$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!
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

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.

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...

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.

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.

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.

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

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!

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.

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!

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

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
House rentals with a pool

Slowlife! Blooming Villa! Freshly Renovated

Sunrise Over St. Barths

Blue Palm Estate Townhouse w/ Ocean View

La plus belle vue de l'ile !

Villa Bahia

Bungalow luxueux avec piscine privée

Préstige - Luxurious 3 bedroom by the Beach

Teresa’s Ocean Paradise
Condo rentals with a pool

CasaPisani Tranquil 2Bed condo SimpsonBayYachtClub

Oceanfront w Pool | Maho Beach area

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

cosy apartment

Prive loft

Large 2BR Condo - STEPS FROM BEACH!

Brand New- Maho Condo Studio with Seaview and Pool

Sur Mer - Beachfront 3 bedroom on Simpson Bay
Other vacation rentals with a pool

Waterfront "Bonjour" Beacon Hill St Maarten

Aman_Aria

Escapes at the Emerald – Airport & Beach Nearby

Royal Palm-1st floor-walk right out to the beach

Villa Blue Roc

Indigo Oceanfront Condo Poolside - Unit 1

The Pineapple Suite

Modern 2 bedroom luxury beachside villa with 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 | G$63,613 GYD | G$61,939 GYD | G$64,241 GYD | G$47,710 GYD | G$40,805 GYD | G$41,851 GYD | G$45,199 GYD | G$41,223 GYD | G$34,108 GYD | G$34,945 GYD | G$40,805 GYD | G$60,684 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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