
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.

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.

Maho Love Nest: Unwind by the Rooftop Pool&Hot Tub
This charming, cozy, and tranquil tropical nest is located where all the action is! The golf course, iconic bars, the unprecedented landing strip, the popular Maho and Mullet bay beaches, Maho market with daily fresh take away breakfast/lunch buffets and a divine selection of exotic restaurants are all in walking distance. If you wish to just lounge and relax by the pool, jacuzzi, and private gazebo bar or enjoy the nightlife; it’s all readily available for you to indulge.

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

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.

Apartment garden - swimming pool
Take it easy at this unique and tranquil getaway. Enjoy your vacation in this renovated apartment in Ruby Blue Residences, with swimming pool. Ideally located in Pelican Key, next to the beach, restaurants, groceries, bars, casinos, clubs, Simpson Bay and close to the airport. This apartment, "Saba" is a ground floor unit by the garden , swimming pool, laundry, private and free parking. You will enjoy this peaceful place ! Adults only

Les Alysés - 2BR-private pool
Book your stay in the sun in this beautiful apartment located on the ground floor of a hacienda villa. The turquoise water pool and garden where you can enjoy your meals in the shade of Cycas will be entirely reserved for you. The furnished apartment in a carribé spirit offers you two bedrooms with TV and air conditioning, a bathroom with a large shower, a fully equipped kitchen and a spacious living room with a boxing bag and foosball.

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.

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 !

C344 - Lagoon view with balcony
C344 is a stylish 1-bedroom apartment at The Hills Residence, offering a peaceful lagoon view from a private balcony. Perfect for a relaxing getaway, it features a modern kitchen, cozy living area, and all the comforts of home. Guests can enjoy the shared pool, secure parking, and 24/7 security. Located just minutes from the beach, dining, and shopping, it’s the ideal base for exploring Sint Maarten.
Popular amenities for Cole Bay rentals with a pool
House rentals with a pool

Life's Good

2BR Villa w/ Lagoon View, Pool & Jacuzzi

New-Sunset Place Villa w Stunning Waterfront Views

SeaRenity Villa With Private Pool Indigo Bay

Private 3bdr ocean view villa in Almond Grove

Luxury Bungalow with Amazing Seaview & Pool

Préstige - Luxurious 3 bedroom by the Beach

Ocean view villa at Dawn beach
Condo rentals with a pool

Loft Condo - STEPS FROM BEACH!

"Seaduction" 2 bedroom apartment Nettle Bay

Oceanfront w Pool | Maho Beach area

Popular Beachfront Property Barefoot /Simpson bay

Villa Belharra, amazing view

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

Beachfront Condo| Pool View + Private Beach Access

Luxury Condo "The Q" + Huge Pool Patio + Beach/Bar
Other holiday rentals with a pool

New beautiful sea view 2 P renovated

"Blue Emerald ¤ Studio" swimming pool & fitness in Maho

Sunny Marina Residence

Gorgeous 2 bedroom-17th floor, Fourteen Mullet Bay

magnificent Orient Bay sea view apartment

Pelican Sea View 1bdrm Maison Mazu

Buddha Gardens Studio B

The Emerald at Maho
When is the best time to visit Cole Bay?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $433 AUD | $433 AUD | $418 AUD | $433 AUD | $351 AUD | $382 AUD | $373 AUD | $325 AUD | $297 AUD | $283 AUD | $336 AUD | $383 AUD |
| 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 $45 AUD 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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