
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.

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

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.

Villa Solandra – 3BR Oceanfront Sunset w/ Pool
Welcome to Villa Solandra, a western facing ocean front luxury 3BR/3BA home with a private pool in Indigo Bay. Enjoy romantic & epic sunsets, this cliffside escape blends indoor-outdoor living with sweeping Sea & Bay views, two large oceanfront balconies, and designer interiors. Enjoy a chef inspired kitchen, luxury king suites w/ ensuite baths, private garden just minutes from beaches, dining, Simpson Bay and Maho’s iconic plane spotting. Perfect for families, friends, or romantic getaways.

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.

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

THE HILL HOUSE, 2 Bdr, pool, panoramique vue
Hébergement avec piscine privée et vue à couper le souffle Offrez-vous une parenthèse de rêve dans cette maison élégante, nichée dans le quartier sécurisé Almond Grove Estate. Profitez de 2 chambres climatisées, d’un salon lumineux, d’une cuisine équipée, et surtout d’un espace extérieur idyllique avec piscine et vue panoramique sur Simpson Bay. À seulement 5 min de Marigot, 10 min de l’aéroport et 15 min des plages, c’est l’adresse parfaite pour un séjour inoubliable !

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 .

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 !

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

*NEW* SeaRenity Villa With Private Pool Indigo Bay

La plus belle vue de l'ile !

2 Bedroom Ocean Front Villa, Private Infinity Pool

Luxurious villa with magnificent view ALSO 6bedr!

Teresa’s Ocean Paradise

Coconut Beach Villa Sxm

Modern 3BR with Private Pool
Condo rentals with a pool

Oceanfront w Pool | Maho Beach area

New "Coco Beach" 2 bedrooms beachfront

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

cosy apartment

Sea Lover - Las Brisas

Studio neuf superbe vue sur la mer des Caraïbes

Casa Nova, Indigo Bay SXM

Beachfront Caribbean Breeze in Paradise, SXM
Other vacation rentals with a pool

Pelican Sea View 1bdrm Maison Mazu

Brand new! - Slowlife - Enjoy Villa

Les Oiseaux du Pirate

B-1203 Stunning 2 bedroom corner balcony

Sea View Studio with Infinity Pool – Romantic Stay

The Lost Paradise

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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