
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.

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.

Apt4 (1 bedroom with terraces & amazing sea view)
Warm and Intimate Triplex with 1 Master bedroom, with sea and pool view. Located in Black Palm, an elegant residence of 6 apartments in Indigo Bay, a calm and exclusive neighborhood. Indigo Beach is just a 5-minute walk away. Enjoy the shared pool with sea view. Ideal for up to 2 guests: couples or friends looking for relaxation. - 5 minutes’ walk from Indigo Beach - 5 minutes’ drive from the nearest supermarket - Private parking on site - Concierge service available for any request.

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

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.

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.

Casa Nova, Indigo Bay SXM
CasaNova is an newly built condo in the Indigo Bay gated community. If you like a good view. This place is for you. It’s a 5 minute walk to the beautiful Indigo Bay Beach. The snorkelling will not disappoint. Explore the sunken ship and meet the resident octopus. Have breakfast on our 300sq-ft balcony while overlooking the ocean. Its modern construction methods deliver a comfortable, safe and cool vacation home.

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.
Popular amenities for Little Bay rentals with a pool
House rentals with a pool

Ocean View Villa-Indigo Bay W/Private Pool/0 Steps

Pelican key - BEACH FRONT Villa

Ocean View House 3 Terraces/2BR/2BA - Shared Pool

Sunset View

5B Oceanview villa near Philipsburg

Préstige - Luxurious 3 bedroom by the Beach

Teresa’s Ocean Paradise

Villa Monchal, 1-minute walk to the beach
Condo rentals with a pool

Loft Condo - STEPS FROM BEACH!

Oceanfront w Pool | Maho Beach area

Popular Beachfront Property Barefoot /Simpson bay

Little Bay Condo with Private Pool

Villa Bora Bora - Beach and Caribbean Sea

Saint Maarten La Terrasse Maho

Beach front luxury! Huge 2BR that has it all! 😍🤩😍

Koala 1 – Elegant 1 Bedroom Duplex Sea View
Other vacation rentals with a pool

Life's Good

Orient Bay Dream Studio 2, Sea View

Pelican Sea View 1bdrm Maison Mazu

Ocean Breeze A

Cozy condo in Blue Pelican

Cozy Cabanita, in lush tropical garden with pool

Ciel En Mer, in the heart of Orient Bay, swimming pool

Sea View Studio with Infinity Pool – Romantic Stay
When is the best time to visit Little Bay?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$114,918 GYD | G$92,352 GYD | G$104,889 GYD | G$91,099 GYD | G$88,800 GYD | G$83,577 GYD | G$85,039 GYD | G$81,487 GYD | G$75,846 GYD | G$75,637 GYD | G$83,368 GYD | G$114,918 GYD |
| 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 G$18,805 GYD 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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