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Vacation rentals with a pool in Little Bay

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Little 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

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 Philipsburg

5 out of 5 average rating, 10 reviews

2 Bedroom Ocean Front Villa, Private Infinity Pool

Clearwater is a cliffside waterfront property with one of the most spectacular views on the island! Overlooking Great Bay, Philipsburg, Divi Little Bay, the turquoise Caribbean Sea and the magnificent cruise ships, this one-of-its-kind location will be sure to Wow you. It is perfectly situated for easy access to all SXM has to offer; 2 nearby beaches, restaurants, grocery stores, downtown shopping, bars and entertainment.

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 !

Rental unit in Indigo bay

4.94 out of 5 average rating, 82 reviews

Independent low villa apartment - Indigo Bay

Villa Stella's apartment welcomes you in a unique setting with spectacular views of the Caribbean Sea. Located in a 24-hour secure residence, tranquility is at the rendezvous. You will be just an 8 min walk to Indigo Bay beach and close to shops and restaurants in the Dutch part. Consisting of 2 bedrooms and 2 bathrooms, you can relax in the pool/hot tub overlooking the bay .

Townhouse in Sint Maarten

5 out of 5 average rating, 63 reviews

Indigo Bay Villa Poolside - Ocean 14

Experience refined Caribbean living in this enchanting 2-bedroom villa, nestled within the exclusive Indigo Bay community of St. Maarten. This beautifully designed villa offers a perfect blend of comfort, style, and outdoor elegance, making it an ideal retreat for those seeking tranquility and luxury.

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.

Guesthouse in Little Bay

4.86 out of 5 average rating, 222 reviews

Your oasis with spectacular views and private pool

Long idelness by the infinity pool. Two bedrooms each with its own bathroom and seperate toilette. A few minutes from the beach, shops and nightlife and yet in a quiet and safe area. The guests has the entire home with a private pool. Please check “villa_pi” on instagram for more photos

Vacation rentals for every style

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Popular amenities for Little 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 Cole Bay

5 out of 5 average rating, 32 reviews

Spacious 3BR with Private Cozy Pool

Home in Collectivity of Saint Martin

4.87 out of 5 average rating, 62 reviews

ALMOND BLUE ...Pinel bay view - caribbean feeling

Home in Pelican Key

5 out of 5 average rating, 9 reviews

Pelican Pearl Villa with Pool and Generator

Home in Philipsburg

4.96 out of 5 average rating, 52 reviews

Villa Allamanda a Indigo Bay

Home in Upper Prince's Quarter

4.92 out of 5 average rating, 25 reviews

Teresa’s Ocean Paradise

Home in Collectivité de Saint-Martin

5 out of 5 average rating, 16 reviews

Fairytale ocean views and sunsets!

Condo rentals with a pool

Condo in Marigot

4.95 out of 5 average rating, 95 reviews

Studio "SeaBird" with your feet in the beach

Condo in Marigot

4.98 out of 5 average rating, 46 reviews

Utopia Condo: Cozy, Quiet & Central with a Pool

Condo in Marigot

4.94 out of 5 average rating, 33 reviews

Beachfront property with pool view

Condo in Lowlands

4.86 out of 5 average rating, 35 reviews

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

Condo in Marigot

4.97 out of 5 average rating, 67 reviews

cosy apartment

Condo in Collectivity of Saint Martin

5 out of 5 average rating, 67 reviews

Holidays in the Paradise on the Beach

Condo in Lowlands

4.95 out of 5 average rating, 44 reviews

Brand New- Maho Condo Studio with Seaview and Pool

Condo in Lowlands

4.95 out of 5 average rating, 106 reviews

Sint Maarten La Terrasse Maho

Home rentals with a private pool

Quick stats about vacation rentals with a pool in Little Bay

Total rentals
100 properties
Nightly prices starting at
$90 before taxes and fees
Total number of reviews
2K reviews
Family-friendly rentals
70 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
50 properties have a dedicated workspace

Destinations to explore