
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.

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.

PARADISE ONE TO LAS BRISAS
A proximité de l'aéroport international de JULIANA [10 min], nous vous proposons un appartement de luxe, dans une très belle résidence sécurisée, en bord de lagon, avec une piscine et un jardin PRIVE, qu'une magnifique vue sur les yatchs durant la haute saison. Pour les sorties nocturnes, vous serez idéalement situés, non loin de Simpson Bay, avec de nombreux restaurants, casinos, boites de nuit ect... Possibilité de faire de footing, qui est une attraction incontournable de l'île.

Secret View amazing apartment- Private pool
Welcome to Secret View, a stunning, fully renovated, stylish and modern apartment located directly on the lagoon with a private pool and breathtaking views. Quiet and secure area, next by Maho, Mullet Bay, the golf course, supermarket, bars, restaurants, and casinos. A true sanctuary, it’s sure to be the highlight of your holiday. Private and free parking Your ultimate vacation retreat. Sint Maarten is currently experiencing some daily power outages

THE HILL HOUSE, 2 Bdr, pool, panoramic view
Accommodation with private pool and breathtaking views Treat yourself to a dream break at this stylish home, nestled in the secure Almond Grove Estate neighborhood. Enjoy 2 air-conditioned bedrooms, a bright living room, a full kitchen, and especially an idyllic outdoor space with a pool and panoramic views of Simpson Bay. Just 5 min from Marigot, 10 min from the airport and 15 min from the beaches, it is the perfect address for an unforgettable stay!

VILLA JADE3: 2 BEDROOMS & POOL FEET IN THE WATER
VILLA JADE is a complex of 3 villas, on the waterfront. VILLA JADE 3, our 2 bedroom villa is located in Cul de Sac Bay, facing PINEL Island and the turquoise water nature reserve. Life is peaceful there, kayaking, relaxing, BBQ... You are 5 minutes from the fabulous Baie Orientale, its restaurants, bars and water activities... The 3 villas are adjoining but very private and quiet, your only view is the sea... your only goal is to "enjoy"......

Sea Loft, Breathtaking View – Private Pool
* 200 m² loft * Exceptional sea view * Private pool * 250 meters from the small beach of Galisbay * Terrace with deckchairs, garden furniture, outdoor table and BBQ * Office space * 100 Mbps WiFi * 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, shops and other stores * 5 min to the pier for Saint-Barth and Anguilla, and the taxi station

Ocean Dream Villa
Indulge in luxury at a two-bedroom villa in Indigo Bay, Sint Maarten. Enjoy modern elegance, a private pool, and ocean views. Relax indoors or outdoors, savor gourmet meals, and unwind under starlit skies. Luxurious bedrooms offer ocean vistas. Whether for romance or family, this villa promises a memorable Caribbean escape at Ocean Dream, where luxury meets natural beauty. Book now for an extraordinary island retreat.

"La Vue SXM" Luxe "Villa La Vue" + Beach / Bar / Food
Located in private gated community Indigo Bay, minutes from beach. Villa has private infinity pool and is neighbored by large communal pool. Modern art déco 2 floor villa has 3 bedrooms, 3 full bathrooms, equipped kitchen, balcony, and terrace with ocean views. **Construction of new hotel began in Indigo Bay as of March 2025 which impacts the entire bay** Free : - Champagne on arrival - 1 Mid Housekeeping Services

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 !

Independent apartment at the bottom of the villa – Indigo Bay
The Villa Stella apartment welcomes you in a unique setting with spectacular views of the Caribbean Sea. Located in a 24-hour secure residence, tranquility awaits. You will be just an 8-minute walk to Indigo Bay Beach and close to shops and restaurants in the Dutch side. Composed of 2 bedrooms and 2 bathrooms, you can relax in the pool/jacuzzi overlooking the bay.

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!

C342 - Glorious Lagoon View Apartment with Balcony
Welcome to Apartment C-342 at The Hills Residence Vacation Rentals! Located on the fourth floor of Building 3, this stunning apartment offers an elevated perspective with spectacular views of Simpson Bay. Its prime location makes it the perfect retreat, offering both a peaceful getaway and easy access to local attractions.
Popular amenities for Cole Bay rentals with a pool
House rentals with a pool

Pelican key - BEACH FRONT Villa

Life's Good

Blue Palm Estate Townhouse w/ Ocean View

Private 3bdr ocean view villa in Almond Grove

The best view on the island!

2 Bedroom Ocean Front Villa, Private Infinity Pool

Teresa’s Ocean Paradise

"Sweet Home on the Beach"
Condo rentals with a pool

Oceanfront w Pool | Maho Beach area

"SeaBird" studio, feet in the water on the beach

cosy apartment

Sea Lover - Las Brisas (Sea Lover)

New studio with superb view of the Caribbean Sea

Casa Nova, Indigo Bay SXM

Beachfront Caribbean Breeze in Paradise, SXM

Sint Maarten La Terrasse Maho
Other vacation rentals with a pool

Pelican Sea View 1bdrm Maison Mazu

Brand new! - Slowlife - Enjoy Villa

The Pirate's Birds

Beachfront Royal Palm 1-BR

Sea View Studio with Infinity Pool – Romantic Stay

Villa Blue Roc

Villa Elysian: Luxurious Ocean View in Indigo Bay

Sea view 3BR Spring Sea Villa w/ pool, St Maarten
When is the best time to visit Cole Bay?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $406 CAD | $406 CAD | $392 CAD | $406 CAD | $329 CAD | $358 CAD | $350 CAD | $305 CAD | $278 CAD | $266 CAD | $315 CAD | $359 CAD |
| 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 350 vacation rentals in Cole Bay

Nightly prices starting at
Cole Bay vacation rentals start at $42 CAD per night before taxes and fees

Verified guest reviews
Over 3,990 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
150 properties have a dedicated workspace

Wifi availability
340 of Cole Bay vacation rentals include wifi 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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