Holiday rentals with a pool in Pelican Key

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Top-rated rentals with a pool in Pelican Key

Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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Guest favourite

A cozy living area features a comfortable gray sofa and a wooden coffee table. Two windows offer expansive views of the ocean, with light reflecting off the water. Beams stretch across the ceiling, enhancing the airy feel of the space.

Condo in Simpson Bay

4.81 out of 5 average rating, 181 reviews

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

Top Guest favourite

A bright living area features large glass doors that open to a private outdoor space. A comfortable sofa and a coffee table are positioned on a light-toned rug. A TV is mounted on a sleek white cabinet, while wooden accents add warmth to the design.

Apartment in Simpson Bay

5 out of 5 average rating, 65 reviews

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.

Guest favourite

An outdoor seating area offers a spacious table and comfortable couch, framed by a wooden pergola. Views of the ocean and sailboats are visible in the distance, while tropical plants add a natural touch to the relaxed atmosphere.

Townhouse in Billy Folly Hill

4.94 out of 5 average rating, 89 reviews

Pelican Sea View 1bdrm Maison Mazu

Beautiful large 1 bedroom 1.5 bathroom. Ocean sunset views from the large balcony. Watch the ships come and go. Located in community of Pelican, walking distance to a beach or steps to the pool, still near the heart of Simpson Bay. Vaulted ceilings with fans in the bedroom & living room. The bedroom has AC, romantic hand carved king size bed with ocean views. Mazu the sea goddess, brings peace and calm. The atmosphere, stunning ocean views create the perfect setting to relax and unwind.

Guest favourite

Apartment in Pelican

5 out of 5 average rating, 12 reviews

Luxurious Hidden Pearl - Private Pool

This luxurious studio has been remodeled in 2025 and is ready for guests seeking a stylish studio with pool. The room has a brand new kitchen and bathroom and has everything you might need during your vacation. Enjoy the private salt water pool and relax on the deck on the lounge chairs and comfortable seating area's. The outdoor space is beautifully set up and we offer a bbq if you like a home cooked meal. The gorgeous tropical garden and breathtaking ocean views complete the experience.

Guest favourite

The complex features a large swimming pool surrounded by palm trees and lounge areas. In the background, boats can be seen in the calm water beneath a vibrant sunset sky. The building showcases modern architecture with multiple balconies overlooking the pool.

Apartment in Simpson Bay

5 out of 5 average rating, 6 reviews

Gorgeous 2 Bedroom Beachfront Ground Floor

ONLY 10 feet from the beach Our ground floor 2-bedroom 2 bath full kitchen step out of your door directly onto the beach. swimming pool, swim up bar and restaurant. Walking distance to outstanding restaurants. Enjoy all water sports On-site gym, restaurant free internet free laundry facility 24 hour security free parking. *Guests are charged $26.20 per day resort fee at The Hilton Royal Palm (pool,beach, gym usage, pool towel changes,and tax are all included in this low daily resort fee).

Guest favourite

The image depicts a clear blue swimming pool surrounded by lounge chairs and tropical palm trees. In the background, the ocean can be seen alongside a beach area with a white railing, under a bright sky featuring fluffy clouds.

Apartment in Simpson Bay

5 out of 5 average rating, 8 reviews

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!

Top Guest favourite

A serene beachfront view is presented through sliding glass doors, showcasing a private terrace with a small round table and two chairs. Palm trees gently sway in the breeze, framing the clear turquoise sea and sandy beach beyond.

Condo in Marigot

4.96 out of 5 average rating, 136 reviews

"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.

Guest favourite

A spacious swimming pool features clear blue water and is surrounded by palm trees. Lush landscaping adds to the serene environment. The backdrop showcases the resort building and outdoor dining area, all bathed in natural light under a partly cloudy sky.

Apartment in Cole Bay

4.96 out of 5 average rating, 26 reviews

Beachfront Royal Palm 1-BR

This one-bedroom unit is located on the 4th floor of the Royal Palm Hilton Vacation Club in Simpson Bay, St Maarten. This property boasts direct beach access and stunning ocean views! Inside you’ll find a spacious open-plan living area with a pull out sofa, and the modern kitchen is fully equipped. Situated in the heart of it all, close to restaurants, bars & nightlife! Please note: The Royal Palm requires a $250 refundable security deposit at check-in.

Top Guest favourite

An outdoor terrace features comfortable white lounge furniture arranged around a coffee table. Sun loungers are positioned beside a private infinity pool, overlooking the ocean and distant boats. The scene is framed by tropical plants and a clear blue sky, enhancing the serene coastal environment.

Loft in Marigot

4.99 out of 5 average rating, 178 reviews

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

Guest favourite

A bright living area features large glass doors opening to a waterfront view. Neutral-toned furnishings include a comfortable sofa and a unique wooden coffee table atop a circular area rug. Decorative greenery and modern art elements provide subtle accents against the white walls.

Apartment in Point Pirouette

4.91 out of 5 average rating, 131 reviews

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.

Guest favourite

A terrace features a swimming pool surrounded by lounge chairs, offering a view of palm trees and the ocean in the distance. The design includes a blue railing, and the outdoor space is spacious, inviting relaxation in a tranquil environment.

Guesthouse in Cole Bay

4.83 out of 5 average rating, 30 reviews

New ! Apartment with pool and ocean view #3

Take it easy at this unique and tranquil getaway. Newly renovated apartment in complex with pool and ocean view. Ideally located in Pelican Key, next to the beach, restaurants, groceries, bars, casinos, clubs, Simpson Bay and close to the airport. This apartment, "St Maarten" is part of a complex with 5 other independent apartments, with pool, garden, laundry, private and free parking. You will enjoy this peaceful place ! Adults only

Superhost

A vibrant view from the terrace showcases lush greenery and blooming flowers, with colorful buildings framed by palm trees. The sea is visible in the distance, complementing the tranquil residential surroundings. The scene captures a mix of nature and architecture under a clear blue sky.

Apartment in Cole Bay

4.82 out of 5 average rating, 11 reviews

Cozy loft style apartment

Enjoy your own apartment close to the beach during your visit to Sint-Maarten. You will be on the first and last floor of the building and will have a private terrace with a view of the sea. In loft style, the bedroom is located on the mezzanine and has its own AC and wardrobe. The apartment is equipped for all your needs and comfort (kitchen equipment, linens etc). Animals are not accepted. Smoking is prohibited inside.