
Holiday 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!

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

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

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 !

D431 - Condo with amazing view
Take in the amazing views from this modern 1-bedroom condo at The Hills Residence in Simpson Bay. Unit D431 offers a bright and airy space with a fully equipped kitchen, stylish living area, and a private balcony perfect for enjoying morning coffee or sunset skies. Located close to beaches, restaurants, and nightlife. Guests enjoy access to a rooftop pool, gym, and 24/7 security for total comfort.

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

Pelican key - BEACH FRONT Villa

Ocean View Villa-Indigo Bay W/Private Pool/0 Steps

Life's Good

Blue Palm Estate Townhouse w/ Ocean View

2 Bedroom Ocean Front Villa, Private Infinity Pool

Pelican Pearl Villa with Pool and Generator

Teresa’s Ocean Paradise

CoCo Signature Luxurious Villa & Exceptional View
Condo rentals with a pool

Oceanfront w Pool | Maho Beach area

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

cosy apartment

New studio with superb view of the Caribbean Sea

Beachfront Caribbean Breeze in Paradise, SXM

Casa Nova, Indigo Bay SXM

Sint Maarten La Terrasse Maho

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

Pelican Sea View 1bdrm Maison Mazu

Coconut Studio with Sea View

NEW 1BR apt lagoon & sunset view 2/3p

Studio - Simpson Bay Yacht Club

The Lost Paradise

Villa Blue Roc

SeaDream Luxury Villa With Private Pool SXM

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 | $508 NZD | $508 NZD | $491 NZD | $508 NZD | $412 NZD | $449 NZD | $438 NZD | $382 NZD | $349 NZD | $333 NZD | $394 NZD | $450 NZD |
| 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 holiday rentals with a pool in Cole Bay

Total holiday rentals
Explore 350 holiday rentals in Cole Bay

Nightly prices starting at
Cole Bay holiday rentals start at $53 NZD per night before taxes and fees

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

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

Pet-friendly accommodation
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
150 properties have a dedicated workspace

Wi-Fi availability
340 of Cole Bay holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi 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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