
Holiday 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.

Luxury Villa Turquoise Heaven in Pelican Key
Welcome to Villa Turquoise Heaven- Modern Luxury in Pelican Key, SXM Experience the pinnacle of Caribbean elegance at Villa Turquoise Heaven, the newest luxury villa in the exclusive Tepui Residence. Designed for relaxation and style, this modern retreat offers a seamless blend of indoor-outdoor living with unparalleled views of the turquoise Caribbean Sea. From waking up to the gentle sound of waves to savoring sunsets from your private infinity pool, Villa TH offers an unforgettable escape.

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

Teresa’s Ocean Paradise
St. Maarten’s best kept secret with breathtaking ocean views from every room! Step into Teresa’s Ocean Paradise where you’ll wake up to panoramic views of turquoise water. Nestled in a private gated community with a communal pool overlooking the ocean, fully equipped kitchen, and two king bedrooms – each with private bathrooms. Perfectly located to enjoy the best of the Dutch and French side’s beaches and restaurants. A one-of-a-kind property to make your vacation an unforgettable retreat.

Villa Solandra – 3BR Oceanfront Sunset w/ Pool
Welcome to Villa Solandra, a western facing ocean front luxury 3BR/3BA home with a private pool in Indigo Bay. Enjoy romantic & epic sunsets, this cliffside escape blends indoor-outdoor living with sweeping Sea & Bay views, two large oceanfront balconies, and designer interiors. Enjoy a chef inspired kitchen, luxury king suites w/ ensuite baths, private garden just minutes from beaches, dining, Simpson Bay and Maho’s iconic plane spotting. Perfect for families, friends, or romantic getaways.

Panoramic View Terrace Infinity Pool Top Penthouse
Wake up to the magnificent panoramic view of the lagoon on the top floor, rejuvenate your body with a refreshing dip in the private rooftop infinity pool with a coffee or tropical drink. Take a 10 mins stroll to the famous Mullet bay Beach and grab a few freshly French croissants by the Square. After sunset, enjoy the plentiful neighborhood bars and restaurants or take 5 mins drive to Maho where you will find a vast variety of restaurants, casino and clubs or Porto Cupecoy for romance spot.

Coco's Beach House - Simpson Bay Beach
Coco's Beach House is a stunning property just steps away from the Simpson bay beach. It will leave you feeling like you are in paradise, 2 King bedrooms with ensuite, full kitchen, 2 private patios, glittering glimpses of the beautiful turquoise ocean and all the comforts of home. It is the perfect spot for 2 couples or a family with small children. Situated in the heart of the Island, we are walking distance to some of the nicest restaurants on the island, bakery, restaurants & nightlife.

Sea Loft Vue imprenable - piscine privée
* Loft de 200m² * Vue mer exceptionnelle * Piscine privée * A 250 mètres de la petite plage de Galisbay * Terrasse avec chaises longues, salon de jardin, table d'extérieur et BBQ * Espace bureau * Wifi 100 Mbps * TV avec milliers de chaines du monde entier * A 250 m à pied de la marina Fort Louis de Marigot * A 5 min à pied du centre ville de Marigot avec ses restaurants, boutiques et autres commerces * A 5 min de l'embarcadère pour Saint-Barth et Anguilla, et de la station de taxis

The Pineapple Suite
Discover The Pineapple Suite, a chic 2-bedroom retreat accommodating up to 4 guests, nestled within the secure confines of Simpson Bay Yacht Club's gated community. Unwind in modern luxury, relish on-site amenities like the two swimming pools, tennis courts, bbq area and soak in breathtaking views of the yachts, lagoon, hills and sunset from your balcony. Conveniently located near the airport in Simpson Bay within walking distance from restaurants, the beach, bars and supermarkets.

The Blue Door Villa - 4 bed ocean view home
At the Blue Door Villa, we offer our guests all the creature comforts of being in a well-equipped vacation home. We are located on the Dutch side, minutes from the French border in a quiet gated community. The Blue Door Villa is a perfect place to relax while you listen to ocean waves and swim in the infinity pool. There are multiple outdoor spaces offering privacy or space to gather. We are now offering our guests an exclusive, free concierge service.

Appartement indépendant bas de villa - Indigo Bay
L'appartement de la Villa Stella vous accueille dans un cadre unique avec une vue spectaculaire sur la mer des Caraïbes. Située dans une résidence sécurisée 24h/24, la tranquillité est au rendez-vous. Vous serez à seulement 8 min à pied de la plage d'Indigo Bay et proche des commerces et restaurants de la partie néerlandaise. Composée de 2 chambres et de 2 salles de bain, vous pourrez vous détendre dans la piscine/jacuzzi surplombant la baie .

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 !

Paradiso - 2 bedroom Condo steps to Cupecoy Beach!
✨Paradiso at The Cliff with IRE Vacations ✨ Built on St. Maarten’s “Gold Coast”, the Cliff at Cupecoy Beach has luxury condominium suites, all with ocean views, full amenities and privacy. If you are looking for a secure, comfortable, relaxing vacation, in a lavish setting where the quality service for our guest is unparalleled, then The Cliff at Cupecoy is your next vacation spot.
Popular amenities for Simpson Bay rentals with a pool
House rentals with a pool

Pelican key - BEACH FRONT Villa

Sunrise Over St. Barths

Slowlife! Blooming Villa! Freshly Renovated

Blue Palm Estate Townhouse w/ Ocean View

ALMOND BLUE ...Pinel bay view - caribbean feeling

Villa proche de la plage

5B Oceanview villa near Philipsburg

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

Loft Condo - STEPS FROM BEACH!

Appartement «Seaduction» 2 chambres Nettle Bay

Popular Beachfront Property Barefoot /Simpson bay

Studio «SeaBird» les pieds dans l’eau sur la plage

« Shell Beach » Splendide 2 chambres sur la plage

Luxury Condo "The Q" + Huge Pool Patio + Beach/Bar

cosy apartment

French Kiss apartment, 2 bdr on the beach!
Other holiday rentals with a pool

Sunny Marina Residence

Ocean Dream Villa

Modern Bungalow With Pool - 3 Min Walk To Beach

Azure Heaven, Breathtaking views, Pool, Gym, Maho

Villa Indigo Dream, Indigo Bay SXM

Villa Tibo

Beachfront Royal Palm 1-BR

CondoSTmaarten panoramic (Adults Only)
When is the best time to visit Simpson Bay?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £189 | £203 | £203 | £170 | £145 | £149 | £161 | £147 | £121 | £124 | £145 | £216 |
| 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 holiday rentals with a pool in Simpson Bay

Total holiday rentals
Explore 210 holiday rentals in Simpson Bay

Nightly prices starting at
Simpson Bay holiday rentals start at £60 per night before taxes and fees

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

Family-friendly holiday rentals
120 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
90 properties have a dedicated workspace

Wifi availability
210 of Simpson Bay holiday rentals include wifi 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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