
Vacation rentals with a pool in Simpson Bay
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Simpson Bay
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Oceanfront w Pool | Maho Beach area
Location , Location Location ! You can not get any closer to the ocean than in this cliff side apartment. The sound of waves crashing below and incredible ocean views from every room. The sunrise is magical everyday and by night the glowing lights of Simpson bay. This cliff side apartment has everything you need for a dream stay away from the crowds. . Just steps from 4 beaches Simpson bay, Mullet bay, burgeux bay and a 5minute walk to the world famous Maho Beach with its famous plane landings

The Beach Condo
The Beach Condo, located in Palm Beach Apt. complex is a completely newly renovated 2 bedroom condo right on Simpson Bay Beach. Equipped with all amenities, this is your ideal tropical luxurious getaway. A brand new, fully equipped kitchen, large living and dining area and two king size bed-bedrooms with individual bathrooms give you all the space you need for a retreat in the Caribbean. Lounge on the porch, swim in the pool or live it up on the beach, it's all right there for you to enjoy.

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.

Sunny Outlook - 1-bdr condo - Beachfront Residence
✨ Sunny Outlook with IRE Vacations ✨ This amazing 1 bedroom 1.5 bathroom unit is located at Palm Beach Condo’s, directly on Simpson Bay Beach. Palm beach is very convenient located in Simpson Bay, here you will find beach bars, restaurants and supermarkets within walking distance. Only a 10 minute drive from the airport. Palm beach offers you a large common pool and private access to the beach. Enjoy your day on the beach, at the pool or go on an adventure on our beautiful island!

Brand New- Maho Condo Studio with Seaview and Pool
Brand new studio, centrally located in Maho, with 24/7 security, amenity filled and a short distance to beaches, shopping and nightlife. The studio is a 5 minute walk to Maho Village and an 8 minute walk to the famous Maho Beach where you will find a multitude of restaurants, duty-free shopping and Casino Royale. It's also an 10 minute walk to Mullet Bay, one of the most beautiful and popular local beaches on the island. The location is a convenient 5 minute drive to the airport.

B-702 Stunning Ocean view corner unit
Welcome to Fourteen at Mullet Bay, one of the most exquisite and luxurious beachfront residence in St Maarten located directly on the famous Mullet Bay beach and golf course. <br><br>Welcome to our luxurious one bedroom apartment, situated on the seventh floor and boasting captivating views of the pristine beach. Prepare to immerse yourself in a haven of opulence and tranquility, where every detail has been meticulously curated to provide an unparalleled coastal retreat.<br><br>

New a Paradise on the beach!
Saint-Martin Baie Nettlé the new 2-room apartment "Paradis sur la plage" offers a fantastic sea view, 4 swimming pools, 2 tennis courts, it is located in the secure complex, highly sought after Le Nettlé Bay Beach Club within walking distance of good restaurants, a bakery, a wine cellar, a supermarket, a water sport, 4 restaurants. Come and discover this wonderful renovated accommodation with parking, fully equipped, it will be perfect for your next vacation on the waterfront!

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.

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.

"Blue Emerald € Studio" pool & fitness in Maho
Relax in this quiet and elegant tropical cocoon. All cooking utensils for homebodies, connected TV, free Wi-Fi, Netflix enabled, and also the delicious swimming pool just across the street and the high-tech weight room for the most motivated. Close to the tourist center (shopping, restaurants, bars, clubs...) and Mullet Bay Beach (800 m)... Come and enjoy a modern and comfortable space, ideal for couples or solo travelers. You'll love it...

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 !
Popular amenities for Simpson Bay rentals with a pool
House rentals with a pool

Pelican key - BEACH FRONT Villa

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

Sunrise Over St. Barths

Luxury Bungalow with Amazing Seaview & Pool

2 Bedroom Ocean Front Villa, Private Infinity Pool

LODGE Elegant Cocoon, Tropical Terrace, Sea View

Paradise View, Creole house with private pool

Préstige - Luxurious 3 bedroom by the Beach
Condo rentals with a pool

Royal Palm-5th floor-Amazing OceanViews-1 Bedroom

Villa Belharra, amazing view

"SeaBird" studio, feet in the water on the beach

Premium studio with Caribbean sea view & swimming pool - Marigot

Vacation in Paradise on the Beach

Large 2BR Condo - STEPS FROM BEACH!

Casa Nova, Indigo Bay SXM

Saint Maarten La Terrasse Maho
Other vacation rentals with a pool

Gorgeous 2 bedroom-17th floor, Fourteen Mullet Bay

Pelican Sea View 1bdrm Maison Mazu

Studio - Simpson Bay Yacht Club

Apartment TalyJay

Simpson Bay Beach 3 Bedroom with pool

The Lost Paradise

Softy green, baie Nettlé

Palm View Condo with pool
When is the best time to visit Simpson Bay?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$53,111 GYD | G$56,875 GYD | G$56,875 GYD | G$47,675 GYD | G$40,775 GYD | G$41,820 GYD | G$45,166 GYD | G$41,193 GYD | G$34,083 GYD | G$32,411 GYD | G$35,547 GYD | G$43,075 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 Simpson Bay

Total vacation rentals
Explore 210 vacation rentals in Simpson Bay

Nightly prices starting at
Simpson Bay vacation rentals start at G$16,728 GYD per night before taxes and fees

Verified guest reviews
Over 4,510 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
90 properties have a dedicated workspace

Wi-Fi availability
210 of Simpson Bay vacation rentals include wi-fi access

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

4.8 Average rating
Simpson Bay stays are highly rated by guests—averaging 4.8 out of 5!
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