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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.

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Rental unit in Point Pirouette

4.92 out of 5 average rating, 100 reviews

Secret View amazing apartment- Private pool

Secret View, amazing apartment directly on the lagoon with private pool. Totally and newly renovated apartment with one separate bedroom, 1,5 bath, full equipped kitchen, huge terrace, private pool, directly on the lagoon. Very quiet and secure location, next to Maho, Mullet Bay , golf course , supermarket, bars, restaurants, casinos. A really relaxing place, it will be the best part of your holidays. Private and free parking. Sint Maarten is currently experiencing some daily power outages

Rental unit in Simpson Bay

5 out of 5 average rating, 19 reviews

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.

Guesthouse in Cole Bay

4.96 out of 5 average rating, 26 reviews

New! Apartment with pool and ocean view#4

Take it easy at this unique and tranquil getaway. Renovated apartment in a complex with pool and ocean view. Ideally located in Pelican Key, next to the beach, restaurants, groceries, bars, casinos, clubs , Simpson Bay and close to the airport. This apartment, "Statia" is part of a complex with 5 other independent apartments, with swimming pool, garden, laundry, private and free parking. You will enjoy this peaceful place ! Sint Maarten is currently experiencing some daily power outages

Condo in Maho

4.89 out of 5 average rating, 188 reviews

Serene Oasis: 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, at your fingertips!

Rental unit in Oyster Pond

4.88 out of 5 average rating, 110 reviews

Lovely Studio Apartment with Pool & Nature Views!

Take a break and unwind at this peaceful studio apartment, perfect for your Caribbean getaway! This fully equipped studio is located just 7-10 minutes away from the capital, Philipsburg, and a few minutes away from several beautiful beaches. It also has gorgeous scenic views and an inviting and relaxing pool! As well as a rooftop terrace with scenic 360 views. Baby crib and grill available upon request for small fee and washer & dryer available on premise for free use.

Loft in Marigot

4.99 out of 5 average rating, 136 reviews

Sea Loft Stunning View - Private Pool

* 200m² Loft * Exceptional sea views * Private pool * 250 meters to small beach Galisbay * Terrace with sun loungers, garden furniture, garden furniture, outdoor table, and BBQ * Desk area * 100 Mbps WiFi * TV with thousands of channels from all over the world * A 250m walk to Marina Fort Louis de Marigot * 5 min walk to the city center of Marigot with its restaurants, shops and other shops * 5 min from the pier for St. Barts and Anguilla, and the taxi station

Villa in Cul-de-Sac

4.95 out of 5 average rating, 100 reviews

VILLA JADE3: 2 BEDROOMS & POOL FEET IN THE WATER

VILLA JADE is a complex of 3 villas , feet in the water. VILLA JADE 3, our 2 bedroom villa is located in the Bay of Cul de Sac, facing the Ilet PINEL and the nature reserve with turquoise waters. Life is peaceful, kayak outings, idleness, BBQ ... You are 5 minutes from the fabulous Oriental Bay, its restaurants, bars and water activities... The 3 villas are terraced but very intimate and quiet, your only view is the sea....your only goal is to " enjoy"......

Home in Calabash Rd, Cole Bay

4.93 out of 5 average rating, 127 reviews

THE HILL HOUSE, 2 Bdr, pool, panoramic view

The house consists of 2 beautiful bedrooms with pool in the residential area of Almond Grove Estate, secured 24 hours a day, (luxury residence), the villa is completely private, you will not share the pool and its yard. You will appreciate the charm of this house. The view is just magnificent, green hills and views of Simpson Bay, a place both discreet and close to tourist hustle and bustle, shopping and beaches.

Rental unit in Little Bay

4.98 out of 5 average rating, 129 reviews

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 !

Condo in Cole Bay

4.82 out of 5 average rating, 51 reviews

Comfy Loft Unit #1 @Lagoon Garden Apartments

The loft is in a quiet neighborhood with groceries, bars, and small restaurants within walking distance. Just a 15-minute walk from Simpson Bay with Casino, Movie, and Restaurants. It has a full kitchen with a dining table. The bedroom is upstairs with the bathroom downstairs. There is a balcony to relax and enjoy the breeze. There is a stove, fridge, and other amenities. The room is fully air-conditioned.

Rental unit in Simpson Bay

5 out of 5 average rating, 8 reviews

Studio - Simpson Bay Yacht Club

Located in the Simpson Bay Yacht Club, the residence is gated and secured 24/7. Available amenities include 2 pools, an outdoor Jacuzzi, and 2 tennis courts. The accommodation is close to bakeries, restaurants, supermarkets, a cinema, and beaches. The main street of Simpson Bay is lively and attractive in the evening for strolling. Your private parking space is located in front of the studio.

Villa in Philipsburg

4.98 out of 5 average rating, 250 reviews

Villa Dream View Belair Sint Maarten SXM

Embrace the tranquility in a friendly tropical caribbean modern designed private villa with spacious rooms that are sure to keep you comfortable and feeling at home. Enjoy the sunny day with infinity pool overlooking caribbean sea or enjoy the sea view while watching the sailing huge cruise ships.

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Popular amenities for Cole Bay rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in Collectivity of Saint Martin

4.98 out of 5 average rating, 42 reviews

New! On La Plage Villa 2ch sea view pool

Home in Lowlands

4.9 out of 5 average rating, 71 reviews

Sapphire Fantasy : Oceanfront paradise

Home in Collectivity of Saint Martin

5 out of 5 average rating, 19 reviews

Fantastic 2 bedroom villa, pools, tennis

Home in Collectivity of Saint Martin

4.87 out of 5 average rating, 62 reviews

ALMOND BLUE ...Pinel bay view - caribbean feeling

Home in Les Terres Basses

5 out of 5 average rating, 17 reviews

Luxury Bungalow Sea & Pool View

Home in Pelican Key

5 out of 5 average rating, 9 reviews

Pelican Pearl Villa with Pool and Generator

Home in Upper Prince's Quarter

4.92 out of 5 average rating, 25 reviews

Teresa’s Ocean Paradise

Home in Philipsburg

4.96 out of 5 average rating, 52 reviews

Villa Allamanda a Indigo Bay

Condo rentals with a pool

Condo in Lowlands

4.86 out of 5 average rating, 73 reviews

Amenity-Filled Maho Studio, Close to Airport/Beach

Condo in Marigot

4.95 out of 5 average rating, 95 reviews

Studio "SeaBird" with your feet in the beach

Condo in Lowlands

4.86 out of 5 average rating, 35 reviews

Maho 1BR Condo w/ocean view, pool & Free Wi-Fi

Condo in Collectivity of Saint Martin

5 out of 5 average rating, 67 reviews

Holidays in the Paradise on the Beach

Condo in Marigot

5 out of 5 average rating, 18 reviews

Beautiful sea view duplex with pool and beach access

Condo in Lowlands

4.95 out of 5 average rating, 106 reviews

Sint Maarten La Terrasse Maho

Condo in Lowlands

4.86 out of 5 average rating, 44 reviews

Havya Cozy Stays

Condo in Orient Bay

4.87 out of 5 average rating, 271 reviews

Charming Studio 1 in Baie Orientale (Orient Bay)

Home rentals with a private pool

Quick stats about vacation rentals with a pool in Cole Bay

Total rentals
310 properties
Nightly prices starting at
$30 before taxes and fees
Total number of reviews
3K reviews
Family-friendly rentals
140 properties are a good fit for families
Pet-friendly rentals
40 properties allow pets
Rentals with dedicated workspaces
150 properties have a dedicated workspace

Destinations to explore