
Vacation rentals with a pool in Cole Bay
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Cole 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

cosy apartment
Profitez d'un logement élégant et central. Proche de la capital (Marigot) avec des commerces et des restaurants a 10 minutes a pied, un accès piscine et plage privé, le marche de marigot est proche avec son poisson Frais tout les mercredi et samedi matin. Nous attirons l’attention des voyageurs sur le fait que les conditions météo propres aux antilles peuvent amener des coupures temporaires de la distribution de l’électricité et de l’eau. Nous précisons que ces désagréments son peu fréquents

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.

Pelican Sea View 1bdrm Maison Mazu
Beautiful large 1 bedroom 1.5 bathroom. Ocean sunset views from the large balcony. Watch the ships come and go. Located in community of Pelican, walking distance to a beach or steps to the pool, still near the heart of Simpson Bay. Vaulted ceilings with fans in the bedroom & living room. The bedroom has AC, romantic hand carved king size bed with ocean views. Mazu the sea goddess, brings peace and calm. The atmosphere, stunning ocean views create the perfect setting to relax and unwind.

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 salt water pool and relax on the deck on the lounge chairs and comfortable seating area's. 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.

SeaBelle 2 Bedroom Condo in Indigo Bay
Welcome to your home away from home in the heart of Sint Maarten! Nestled in the tranquil and upscale Indigo Greens development, this stunning 2-bedroom, 2-bathroom apartment offers a perfect blend of comfort, style, and convenience. Whether you’re here to explore the island or unwind in paradise, this apartment offers everything you need for a memorable stay. With its central location, modern comforts, and inviting ambiance, it’s the perfect base for your Sint Maarten getaway.

"SeaBird" studio, feet in the water on the beach
The "SeaBird studio" is ideally located with a beautiful view of the Caribbean Sea and an idyllic beach just for you! It offers plenty of comfort and storage with refined and original decoration. The residence is perfectly secure with a large swimming pool and tropical garden. Everything is within walking distance: grocery store, local market, shops, traditional or gourmet restaurants, ferry station to other islands, etc... High-speed Wi-Fi and TV Europe and America.

Beachfront Royal Palm 1-BR
This one-bedroom unit is located on the 4th floor of the Royal Palm Hilton Vacation Club in Simpson Bay, St Maarten. This property boasts direct beach access and stunning ocean views! Inside you’ll find a spacious open-plan living area with a pull out sofa, and the modern kitchen is fully equipped. Situated in the heart of it all, close to restaurants, bars & nightlife! Please note: The Royal Palm requires a $250 refundable security deposit at check-in.

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.

Villa Belharra, amazing view
You dream of a vacation in paradise, Villa Belharra will satisfy you. Unique location directly on the beach, breathtaking view day and night. New apartment for 2/4 people. It is located in a private, quiet and secure residence (night guard) which has 4 private swimming pools, 2 tennis courts, and parking lots. Next to all amenities there are food shops (supermarket, bakery, caterer ...), pharmacy, car rental restaurant.

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 !
Popular amenities for Cole Bay rentals with a pool
House rentals with a pool

Slowlife! Blooming Villa! Freshly Renovated

Blue Palm Estate Townhouse w/ Ocean View

The best view on the island!

LODGE Elegant Cocoon, Tropical Terrace, Sea View

Paradise View, Creole house with private pool

Préstige - Luxurious 3 bedroom by the Beach

Villa Monchal, 1-minute walk to the beach

Infinite Blue – Elegant Villa & Turquoise Views
Condo rentals with a pool

CasaPisani Tranquil 2Bed condo SimpsonBayYachtClub

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

Sea Lover - Las Brisas (Sea Lover)

The Beach Condo

Brand New- Maho Condo Studio with Seaview and Pool

Large 2BR Condo - STEPS FROM BEACH!

Saint Maarten La Terrasse Maho

Studio on the water in the Simpson Bay Yacht Club
Other vacation rentals with a pool

Studio 9 Alamanda Resort

Beach apartment

Popular Beachfront Property Barefoot /Simpson bay

Studio Iguana

Studio - Simpson Bay Yacht Club

Green Balaou 15 min à pied Orient-Bay

CondoSTmaarten panoramic (Adults Only)

La Plage Bleue, feet in the water with a pool
When is the best time to visit Cole Bay?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$60,577 GYD | G$60,577 GYD | G$58,488 GYD | G$60,577 GYD | G$49,088 GYD | G$53,475 GYD | G$52,222 GYD | G$45,537 GYD | G$41,568 GYD | G$47,835 GYD | G$52,430 GYD | G$60,786 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 |
Quick stats about vacation rentals with a pool in Cole Bay

Total vacation rentals
Explore 380 vacation rentals in Cole Bay

Nightly prices starting at
Cole Bay vacation rentals start at G$6,267 GYD per night before taxes and fees

Verified guest reviews
Over 4,180 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
120 properties have a dedicated workspace

Wi-Fi availability
370 of Cole Bay vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Cole Bay rentals

4.8 Average rating
Cole Bay stays are highly rated by guests—averaging 4.8 out of 5!
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