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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.

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Apartment in Marigot, St. Martin

4.82 out of 5 average rating, 115 reviews

Gorgeous studio ON THE BEACH,ocean view

BEAU STUDIO au 2 étage dans une résidence sécurisée,avec plage privée et accès directement par la résidence. Notre studio est l'endroit idéal pour passer de bonnes vacances.Une vue incroyable sur la mer turquoise des caraïbes et des couchers de soleil époustouflants.Il est entièrement équipé en cuisine et le linge de maison ,il y a un lit queen et un canapé lit Il as aussi le wifi et Tv. Il y a une épicerie à 200m,le parking est gratuit et nous sommes à 5 mn du ferry pour St Barth et Anguilla

29 Oct – 5 Nov

$153 SGD per night

Guest favourite

Villa in Indigo Bay, Sint Maarten

4.95 out of 5 average rating, 100 reviews

Villa Life is Good

Sint Maarten Indigo Bay: One whole villa to yourself at 10 minutes from Princess Julianna airport the Villa "Life is Good" with infinity pool is located on the mountainside with a 180 degree view of the sea. View of the Islands, Saba, St Kitts & Nevis and Sint Eustatius. A spectacle of breathtaking sunrises and sunsets. Far from the noise and hustle of the city, you will find peace and quiet guaranteed. You will find 5 minutes drive from the villa: beaches, restaurants and all amenities.

9–16 May

$820 SGD per night

Flat in Simpson Bay, Sint Maarten

5.0 out of 5 average rating, 3 reviews

The Loft at Simpson Bay Yacht Club

Welcome to The Loft at the Simpson Bay Yacht Club. 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.

4–11 Jul

$223 SGD per night

Guest favourite

Apartment in Maho, Sint Maarten

4.88 out of 5 average rating, 171 reviews

2 Min to Beach/Exclusive Rooftop Jacuzzi, Pool+Bar

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!

12–19 Oct

$213 SGD per night

Apartment in Simpson Bay, Sint Maarten

5.0 out of 5 average rating, 6 reviews

Renovated 2-Level Condo @ Simpson Bay Yacht Club

This spacious and luxurious 1-bedroom 2-level condo, has been appointed with high-end Miele appliances, granite counters, rain-shower heads in both bathrooms, Stressless leather couches and Posture-pedic beds for your ultimate comfort. The main floor balcony and very private upper balcony offer gorgeous views across the lagoon to nearby marinas and mountains. Your reserved parking is steps from your door in this sought after gated community in the heart of Simpson Bay.

12–19 Aug

$198 SGD per night

Guest favourite

Home in Calabash Rd, Cole Bay, Sint Maarten

4.93 out of 5 average rating, 111 reviews

THE HILL HOUSE, 2 Bdr, pool, panoramique vue

La maison se compose de 2 belles chambres avec piscine dans le quartier residentiel de Almond Grove Estate, sécurisé 24h/24, (résidence de standing), la villa est entièrement privée, vous ne partagerez pas la piscine et ses extérieurs. Vous allez apprécier le charme de cette maison. La vue est juste magnifique, collines verdoyantes et mer de Simpson bay, un endroit à la fois discret et proche de l agitation touristique, des commerces et des plages.

13–20 Sep

$404 SGD per night

Guest favourite

Loft in Marigot, St. Martin

4.99 out of 5 average rating, 116 reviews

Sea Loft Stunning View - Private Pool

* 200m² loft * Exceptional sea view * Private pool * 250 meters from the small beach of Galisbay * Terrace with sun loungers, garden furniture, outdoor table and BBQ * Office area * Wifi 100 Mbps * TV with thousands of channels from around the world * 250m walk to Fort Louis de Marigot Marina * 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

26 Jan – 2 Feb

$587 SGD per night

Guest favourite

Flat in Little Bay, Sint Maarten

4.98 out of 5 average rating, 113 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 !

23–30 Sep

$471 SGD per night

Guest favourite

Flat in Simpson Bay, Sint Maarten

5.0 out of 5 average rating, 5 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.

31 May – 7 Jun

$216 SGD per night

Guest favourite

Apartment in Marigot, Guadeloupe

5.0 out of 5 average rating, 18 reviews

D'Ô, cozy studio facing the sea Caraîbes, Baie Nettlé

Very nice studio for two people located on the floor of a luxury residence, secure and guarded, 4 pools and two tennis courts. Fully equipped kitchen and bath. Decorated terrace with magnificent views of the Caribbean sea. Close to all amenities, supermarket, doctor, pharmacy, hairdresser and restaurants.

6–13 Nov

$159 SGD per night

Guest favourite

Villa in Philipsburg, Sint Maarten

4.99 out of 5 average rating, 224 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.

13–20 Oct

$623 SGD per night

Guest favourite

Flat in Simpson Bay, Sint Maarten

4.93 out of 5 average rating, 273 reviews

Fig Paradis ocean front pool & jacuzzi

We offer romantic gastronomic dinners by a private chef on site. Elegant and Chic Apartment with Terrace opening into your private tropical Garden. The pool and Jacuzzi are a short path from the garden to the ocean view side of our home.

15–22 Apr

$238 SGD per night

Holiday rentals for every style

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Convenient locations with everyday essentials

Popular amenities for Cole Bay rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Guest favourite

Home in Philipsburg, Sint Maarten

5.0 out of 5 average rating, 7 reviews

2 Bedroom Ocean Front Villa

15–22 Oct

$703 SGD per night

Guest favourite

Home in Collectivité de Saint-Martin, St. Martin

4.88 out of 5 average rating, 32 reviews

"Salty Beach" - Amazing 1 bedroom beachfront

1–8 Oct

$241 SGD per night

Guest favourite

Home in Les Terres Basses, St. Martin

5.0 out of 5 average rating, 9 reviews

Luxury Bungalow Sea & Pool View

12–19 Nov

$310 SGD per night

Guest favourite

Home in Koolbaai, Sint Maarten

5.0 out of 5 average rating, 6 reviews

Blue Palm Estate Townhouse w/ Ocean View

29 May – 5 Jun

$325 SGD per night

Home in Cole Bay, Sint Maarten

4.89 out of 5 average rating, 38 reviews

Saint-Tropez With Ocean View - Boat Charter

19–26 May

$876 SGD per night

Guest favourite

Home in Collectivity of Saint Martin, St. Martin

5.0 out of 5 average rating, 13 reviews

Fantastic 2 bedroom villa, pools, tennis

19–26 Sep

$402 SGD per night

Guest favourite

Home in Simpson Bay, Sint Maarten

5.0 out of 5 average rating, 68 reviews

Villa Blue View .. stunning views of endless sea!

19–26 Nov

$1,208 SGD per night

Guest favourite

Home in Sint Maarten, Sint Maarten

5.0 out of 5 average rating, 10 reviews

*New* The Beach House at Indigo Bay

27 Nov – 4 Dec

$1,412 SGD per night

Apartment rentals with a pool

Guest favourite

Apartment in Orient Bay, St. Martin

4.88 out of 5 average rating, 262 reviews

Charming Studio 1 in Baie Orientale (Orient Bay)

2–9 Sep

$109 SGD per night

Guest favourite

Apartment in Marigot, St. Martin

5.0 out of 5 average rating, 15 reviews

Beachfront property with pool view

23–30 Apr

$121 SGD per night

Guest favourite

Apartment in Marigot, St. Martin

4.94 out of 5 average rating, 87 reviews

Studio "SeaBird" with your feet in the beach

2–9 Sep

$136 SGD per night

Guest favourite

Apartment in Marigot, St. Martin

4.91 out of 5 average rating, 35 reviews

My Home : Very comfortable apartment for 4 people

3–10 Sep

$142 SGD per night

Guest favourite

Apartment in Marigot, St. Martin

5.0 out of 5 average rating, 36 reviews

Utopia Condo: Cozy, Quiet & Central with a Pool

18–25 Jul

$160 SGD per night

Guest favourite

Apartment in Cole Bay, Sint Maarten

4.86 out of 5 average rating, 49 reviews

Comfy Loft Unit #1 @Lagoon Garden Apartments

7–14 Aug

$105 SGD per night

Guest favourite

Apartment in Simpson Bay, Sint Maarten

5.0 out of 5 average rating, 27 reviews

CasaPisani Tranquil 2Bed condo SimpsonBayYachtClub

13–20 Apr

$363 SGD per night

Guest favourite

Apartment in Simpson Bay, Sint Maarten

4.9 out of 5 average rating, 10 reviews

Lovely Lagoon Townhouse SBYC

5–12 Sep

$261 SGD per night

Quick stats about holiday rentals with a pool in Cole Bay

Total rentals
280 properties
Rentals with dedicated workspaces
140 properties have a dedicated workspace
Pet-friendly rentals
40 properties allow pets
Family-friendly rentals
140 properties are a good fit for families
Total number of reviews
2.5K reviews
Nightly prices starting at
$41 SGD before taxes and fees

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