
Holiday rentals in Cole Bay
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Top-rated holiday rentals in Cole Bay
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Sunset 2BR 2BH House in Cupecoy with Private Pool
This Brand New Luxurious town house is perfectly located in the sought after area of Cupecoy. Offering a perfect blend of comfort, convenience & Caribbean charm for a memorable stay that fits perfectly to your weekend getaways, staycation, or work from home This house will bring your Caribbean dream vacation come true. It is walking distance to the Cupecoy beach and just 5 minutes drive from MulletBay & Maho Beach It has a private plunge pool and a rooftop terrace with amazing lagoon views.

Endless Views @ Acqua Bleu
Nestled in the heart of Saint Martin, Acqua Bleu offers breathtaking views of turquoise waters and pristine beaches. You'll have direct access to some of the most gorgeous spots on the island, ensuring endless fun in the sun. You’ll enjoy access to various amenities, including a fully equipped kitchen, spacious living areas, a refreshing swimming pool, and much more! Acqua Bleu features two king bedrooms, each accompanied by a private bathroom. Get ready to enjoy a truly rejuvenating vacation!

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.

CasaPisani Tranquil 2Bed condo SimpsonBayYachtClub
A spacious apt in a great location. This apt is located on the 2nd and 3rd floor in a gated +24/7 secured community of the Simpson Bay Yacht Club. A fully stocked kitchen. Open concept Dining/Living room combination leads to a covered patio for outdoor dining with panoramic bay views. 2 large and spacious bedrooms with private baths. Enjoy morning coffee or afternoon cocktails on one of the 3 patios all overlooking water. This complex offers 2 pools, Tennis, Jacuzzi, security and parking.

Ocean View Villa Little Bay
🌴 Villa Little Bay – Oceanview Bliss With 360° Views Enjoy the peaceful sound of the waves and a serene, private atmosphere that’s still close to everything. We’re located within walking distance to Philipsburg, the vibrant heart of SXM—Front Street, top shopping, restaurants, and the island’s best casinos. The beach is just 5 minutes away, Step outside to your private patio for sunbathing, and shimmering ocean‑view pool. Villa offers the perfect blend of tranquility and convenience.

The Beach House Apartment
A stylishly modern one bedroom apartment directly located on the beautiful white sand beach of Simpson Bay. Enjoy the crystal clear waters by day and explore the Caribbean charm of our bustling nightlife. Our island getaway provides you with the full relaxation experience complete with beach chairs, umbrellas, outdoor shower, snorkel gear and paddle boards to complete beach side experience Amenities include free WIFI, kitchen, king size bed, beach chairs, umbrella's and much more

Casa Bay 3 Bedroom in St.Maarten
Welcome to Casa Bay, your tropical retreat in the heart of Cole Bay, St. Maarten. This spacious and beautifully designed 3-bed, 2-bath condo offers the perfect blend of comfort and convenience. Centrally located, you're just 15 minutes from the airport and a short drive to stunning beaches, vibrant nightlife, and a variety of dining options. Whether you're here to relax or explore, Casa Bay is the ideal home base for your island getaway Rental car available at additional fee.

07 yellow cliff
07 YELLOW CLIFF is a brand-new, stylish two-bedroom with breathtaking views of the ocean and a beautiful panoramic of Cul de sac, Orient bay, Tintamarre island and St. Barths from your private terrace. Bright, fully equipped, and tastefully decorated, it offers comfort and elegance with easy access and parking at your door. Enjoy a tranquil setting close to beaches, restaurants, and shops — the perfect spot for couples, friends, or family to relax and soak in paradise

Beautiful, bright apartment with a lagoon view in Simpson Bay
Profitez d’un séjour inoubliable dans cet appartement confortable avec vue sur le lagon. Le logement dispose d’un espace de vie agréable, soigneusement aménagé pour votre confort. Le balcon vous permettra de savourer vos repas ou un café face au lagon, avec une vue apaisante à toute heure de la journée. La cuisine est entièrement équipée. Situé dans une résidence calme, vous êtes à proximité des plages, restaurants, commerces et activités incontournables de l’île.

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

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 !

Modern 3BR with Private Pool
Escape to this modern 3-bedroom, 2.5 bath retreat with own private pool on a tropical island paradise. Each bedroom features comfortable beds and quality linens. The open-concept living area includes a fully equipped kitchen, comfortable living room, and dining area. Just a short drive from the beach, restaurants, and shops. Special long term rates available. Just send an inquiry to discuss further!
Popular amenities for Cole Bay holiday rentals
Other great holiday rentals in Cole Bay

Blue Palm Estate Townhouse w/ Ocean View

Coco's Beach House - Simpson Bay Beach

Modern Sea View Apartment from Pinel island

PARADISE ONE TO LAS BRISAS

C314 - Stunning 1 Bedroom Apartment

Restful Room - Fast Wi-Fi - Pool - Lagoon Garden

A heavenly Sint Maarten's retreat

Luxurious Sunset Lagoon View
When is the best time to visit Cole Bay?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $249 SGD | $236 SGD | $236 SGD | $251 SGD | $206 SGD | $195 SGD | $191 SGD | $180 SGD | $171 SGD | $185 SGD | $192 SGD | $236 SGD |
| 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 |
Frequently Asked Questions
What are the best places to stay in Cole Bay?
Cole Bay has a mix of vacation rentals near the marina, as well as apartments and houses close to waterfront dining and local markets. Many accommodations feature outdoor space and family-friendly amenities.
What are the best things to do in Cole Bay with kids?
Families often enjoy boat tours departing near the marina, checking out local parks, and sampling Caribbean treats at casual eateries. Calm beaches around Cole Bay make popular spots for swimming and building sandcastles.
What are some of the best things to do in Cole Bay?
Explore marina activities, dine at waterfront restaurants, and browse local markets for crafts or specialties. Many visitors join boat tours or relax at nearby beaches, combining leisure and adventure.
How is the weather in Cole Bay?
Cole Bay has warm temperatures year-round, ranging from 74°F to 89°F (23°C to 32°C), with more rainfall in autumn months. Lightweight clothing and sun protection are useful as the area is generally sunny and humid.
When is the best time to visit Cole Bay?
Late winter and early spring are often recommended for milder weather and lower rainfall, while summer draws visitors for vibrant festivals and warm temperatures. Some travelers enjoy the quieter atmosphere during autumn months.
What are the best places to visit in Cole Bay?
Explore the marina area and waterfront markets, then take in local art murals or sample Caribbean dishes at neighborhood restaurants. Cole Bay is also near several beaches and nature spots favored by visitors.
What are some hiking trails in Cole Bay?
Cole Bay and the surrounding region have trails that lead through low hills, scenic overlooks, and nature reserves. Guided walks are often available, allowing travelers to spot local flora and enjoy gentle outdoor exercise.
What are some family activities we can do in Cole Bay?
Families in Cole Bay enjoy waterfront parks, boat tours, and outings to local markets or casual eateries. Kid-friendly beaches around the area often have calm waters suitable for swimming and sandcastle fun.
What are some of the best day trip ideas from Cole Bay?
Plan a beach day on the island's sandy shores, visit lively Phillipsburg for shopping and cultural sites, or explore hiking trails in nearby nature areas. Guided snorkeling tours and boat outings are frequently suggested activities.
Are there any pet friendly accommodations available in Cole Bay?
Many vacation rentals in Cole Bay welcome pets, especially apartments and homes with outdoor spaces. Be sure to check pet policies and ask about local parks or waterfront areas suitable for walks with your companion.
What are some local tips for visiting Cole Bay?
Locals often suggest exploring culinary spots, taking in sunset views at waterfront areas, and browsing markets for handmade crafts. Comfortable shoes and a relaxed schedule help travelers enjoy Cole Bay's slower pace.
What is Cole Bay known for?
Cole Bay is known for its waterfront marinas, vibrant boating culture, and friendly community atmosphere. The area features local dining, markets, and convenient access to both beaches and urban amenities.
What are the best hidden gems to explore in Cole Bay?
Explore waterfront markets with local crafts, visit tucked-away eateries serving Caribbean comfort foods, or join a guided boat excursion departing near Cole Bay. Neighborhood marinas and mural-lined streets add to the area's distinctive character.
What are the best foods to try in Cole Bay?
Cole Bay is known for Caribbean cuisine, such as grilled seafood, stewed chicken, and johnnycakes. Island-style barbecue, fresh fish, and side dishes with plantains or rice are frequently suggested by locals.
What should I bring for a trip to Cole Bay?
Pack lightweight clothing, a swimsuit, sunscreen, and comfortable sandals for exploring beaches and markets. A reusable water bottle, sunhat, and insect repellent are often suggested for outdoor activities and island excursions.
What is the nightlife in Cole Bay like?
Cole Bay has bars, casual restaurants, and lounges that host music and social gatherings. The area draws a mix of locals and visitors, creating a lively yet laid-back atmosphere, especially along waterfront spots.
What are the most popular events or festivals in Cole Bay?
Carnival season, often celebrated across Sint Maarten in late spring, features lively parades and music that locals and visitors enjoy. Food, dance, and cultural performances add to the festive atmosphere around Cole Bay and nearby neighborhoods.
Are there family friendly vacation rentals in Cole Bay?
Cole Bay has a variety of vacation rentals, including spacious houses and apartments that accommodate families. Many options feature amenities like kitchens and outdoor areas, making it easy for travelers of all ages to relax together.
Quick stats about holiday rentals in Cole Bay

Total holiday rentals
Explore 500 holiday rentals in Cole Bay

Nightly prices starting at
Cole Bay holiday rentals start at $38 SGD per night before taxes and fees

Verified guest reviews
Over 5,950 verified reviews to help you choose

Family-friendly holiday rentals
180 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 50 rentals that welcome pets

Holiday rentals with a pool
380 properties feature pools

Rentals with dedicated workspaces
180 properties have a dedicated workspace

Wifi availability
500 of Cole Bay holiday 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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