
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.

Luxury Condo "The Q" + Huge Pool Patio + Beach/Bar
This luxury 2-bedroom, 2-bathroom apartment boasts breathtaking ocean views and a private expansive pool, offering a sense of serenity that’s unmatched. Largest pool in the neighborhood. Ocean views from shower! Thoughtfully managed by a top-tier host, every detail has been considered to ensure your stay is comfortable and unforgettable. Nestled near the beach and steps away from a chic beach bar, this place provides some of the island’s best views—an oasis of beauty in the heart of St Maarten.

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.

Maho Love Shack: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.

"SeaBird" studio, feet in the water on the beach
The "SeaBird studio" is ideally located with a beautiful view of the Caribbean Sea and an idyllic beach just for you! It offers plenty of comfort and storage with refined and original decoration. The residence is perfectly secure with a large swimming pool and tropical garden. Everything is within walking distance: grocery store, local market, shops, traditional or gourmet restaurants, ferry station to other islands, etc... High-speed Wi-Fi and TV Europe and America.

Sea Loft, Breathtaking View – Private Pool
* 200 m² loft * Exceptional sea view * Private pool * 250 meters from the small beach of Galisbay * Terrace with lounge chairs, garden furniture, outdoor table and BBQ * Office area * 100 Mbps Wi-Fi * 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, boutiques and other shops * 5 min to the pier for Saint-Barth and Anguilla, and the taxi station

Studio Ocean Front, 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 put you at awe. It is perfectly situated for easy access to all SXM has to offer; restaurants, beaches, grocery stores, downtown shopping, bars and entertainment.

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 !

CondoSTmaarten panoramic (Adults Only)
Condo St. Maarten is located in the quiet and secure subdivision of Indigo Bay. 8 miles or 5 km from Juliana Airport. Ideally located between the Dutch capital Phillipsburg with its beautiful bay lined with a long white sandy beach, duty free shops, cruise boats and Simpson Bay renowned for nightlife, casinos, restaurants and night clubs. Supermarkets are a 5-minute drive away.

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.

Your oasis w/ocean view, private pool&hiking track
Long idelness by the infinity pool. Two bedrooms each with their own bathrooms. A few minutes from the beach, shops and nightlife and yet in a quiet, secluded and safe district. The guests has the entire unit with a private pool, a pool deck for sunbathing and a wide porch including a seating and a dining place. The house has a private gated parking.

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 Little Bay rentals with a pool
House rentals with a pool

Pelican key - BEACH FRONT Villa

Comfort & Views - LUX Fortress

Luxury Bungalow with Amazing Seaview & Pool

5B Oceanview villa near Philipsburg

Paradise View, Creole house with private pool

LODGE Elegant Cocoon, Tropical Terrace, Sea View

Villa Allamanda a Indigo Bay

Infinite Blue – Elegant Villa & Turquoise Views
Condo rentals with a pool

Oceanfront w Pool | Maho Beach area

Popular Beachfront Property Barefoot /Simpson bay

NEW! Orient Bay's best view 2 bedrooms 2 bathrooms

cosy apartment

Brand New- Maho Condo Studio with Seaview and Pool

Large 2BR Condo - STEPS FROM BEACH!

Villa Bora Bora - Beach and Caribbean Sea

Luxury Little Bay- Caribbean Blue
Other vacation rentals with a pool

Gorgeous 2 bedroom-17th floor, Fourteen Mullet Bay

Pelican Sea View 1bdrm Maison Mazu

Sunny Outlook - 1-bdr condo - Beachfront Residence

"Paradise Beach" - Impressive 2 bedrooms seafront

Studio - Simpson Bay Yacht Club

Indigo Bay Villa Poolside - Ocean 14

EXQUISITE 5-STAR BEACHFRONT VILLA

Love beach loft
When is the best time to visit Little Bay?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ2,020 | ﺩ.ﺇ1,623 | ﺩ.ﺇ1,844 | ﺩ.ﺇ1,601 | ﺩ.ﺇ1,561 | ﺩ.ﺇ1,469 | ﺩ.ﺇ1,495 | ﺩ.ﺇ1,432 | ﺩ.ﺇ1,333 | ﺩ.ﺇ1,451 | ﺩ.ﺇ1,561 | ﺩ.ﺇ2,016 |
| 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 vacation rentals with a pool in Little Bay

Total vacation rentals
Explore 100 vacation rentals in Little Bay

Nightly prices starting at
Little Bay vacation rentals start at ﺩ.ﺇ331 per night before taxes and fees

Verified guest reviews
Over 2,730 verified reviews to help you choose

Family-friendly vacation rentals
70 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
60 properties have a dedicated workspace

Wi-Fi availability
100 of Little Bay vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Little Bay rentals

4.9 Average rating
Little Bay stays are highly rated by guests—averaging 4.9 out of 5!
Destinations to explore
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- Rentals with pools Sint Maarten




