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Vacation rentals with a pool in Simpson Bay Beach

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Simpson Bay Beach

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

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A clear swimming pool reflects sunlight, featuring tranquil ripples across its surface. In the background, several blue lounge chairs are arranged on a deck, flanked by lush greenery, providing a serene environment for relaxation.

Condo in Simpson Bay

4.97 out of 5 average rating, 91 reviews

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

5 star hotel luxury is yours in this modern beach home! 2 guest rooms with en-suite bathrooms and deck access. Enjoy cooking your own meals and dine inside or on the deck (or beach!). Largest deck on Simpson Bay beach has it all: huge daybed, loungers, living and dining areas for your comfort and pleasure. Unwind in the den and enjoy the big screen there or in either bedroom. Your neighbor is a boutique hotel and will gladly serve you meals and drinks right to your deck! Much more info available

A rectangular pool features clear blue water, reflecting light from the sun. The surrounding walls are painted white, with large windows allowing natural light to enter the space. A metal ladder is positioned at one end of the pool.

Condo in Simpson Bay

4.8 out of 5 average rating, 173 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 favorite

A spacious swimming pool is framed by lush landscaping and poolside chairs, offering a serene view of the ocean. The clear blue water reflects the sky, with a backdrop of gently swaying palm trees and distant ships on the horizon.

Condo in Simpson Bay

4.99 out of 5 average rating, 68 reviews

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.

An infinity pool extends over the edge, offering panoramic views of the lagoon. The tranquil water reflects the blue sky, while steps lead from the pool's edge to the terrace. Lush greenery is visible, enhancing the serene atmosphere of the space.

Guest suite in Cupecoy

4.9 out of 5 average rating, 111 reviews

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.

Top guest favorite

A spacious swimming pool is surrounded by lush greenery and palm trees. Lounge chairs are positioned around the pool area, which reflects the clear blue sky and is adjacent to a series of two-story white buildings with blue roofs.

Condo in Simpson Bay

5 out of 5 average rating, 30 reviews

Beachfront Caribbean Breeze in Paradise, SXM

Caribbean Breeze inviting Beach front home. A few steps to our beach and pool. Walk to mainstream. Amazing views . 2/2.5 with huge Master. Hear the waves flowing in onto the shore for those relaxing days and nights. New kitchen, living room , bathrooms, dining area,etc. Unwind on any balcony, penthouse ocean view, on daybed with a nice drink , looking over the verse tranquil ocean. Take a dip in the soothing crystal clear waters, 1 minute walk away. Amenities enclosed & Wi-Fi included.

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, 4 reviews

Sunny Outlook - 1-bdr condo - Beachfront Residence

✨ Sunny Outlook ✨ This amazing completely renovated 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 favorite

A scenic view reveals a large swimming pool surrounded by lounge chairs and colorful flower gardens. The sparkling blue ocean and a distant boat can be seen, under a bright sky with fluffy clouds. Palm trees gently sway in the breeze, adding to the tropical ambiance.

Condo in Lowlands

4.96 out of 5 average rating, 122 reviews

Sint Maarten La Terrasse Maho

It's a cozy large studio with a king size bed, a queen size sleeper sofa and a big balcony, it is at the second floor at Royal Islander Club Resort La Terrasse in Maho, fully equipped and furnished. Located just in front of Maho Bay beach and few minutes walk from Mullet bay beach. There are few restaurants and boutiques like cigar shops, jewelers and beauty store. Casino Royale is right next door. There are also a supermarket for grocery shopping, a pharmacy, a clinic and more...

4.9 out of 5 average rating, 211 reviews

Serene Oasis: 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, at your fingertips!

Top guest favorite

A clear blue swimming pool is surrounded by lush palm trees and tropical plants. Comfortable sun loungers with blue cushions are positioned around the pool area, offering a relaxing space. The backdrop features rolling green hills under a partially cloudy sky.

Condo in Marigot

4.95 out of 5 average rating, 121 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.

A private pool is framed by a wooden deck, offering lagoon views. Two lounge chairs are positioned nearby, with a small round table beside them. The surrounding area is brightened by natural sunlight, enhancing the serene waterscape.

Apartment in Point Pirouette

4.91 out of 5 average rating, 119 reviews

Secret View amazing apartment- Private pool

Welcome to Secret View, a stunning, fully renovated, stylish and modern apartment located directly on the lagoon with a private pool and breathtaking views. Quiet and secure area, next by Maho, Mullet Bay, the golf course, supermarket, bars, restaurants, and casinos. A true sanctuary, it’s sure to be the highlight of your holiday. Private and free parking Your ultimate vacation retreat. Sint Maarten is currently experiencing some daily power outages

Top guest favorite

A private pool is surrounded by a wooden deck, featuring multiple lounge chairs arranged for relaxation. The space offers a clear view of the sea and distant hills, complemented by a bright sky with scattered clouds. The outdoor area invites enjoyment of the coastal scenery.

Loft in Marigot

4.99 out of 5 average rating, 164 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 deckchairs, garden furniture, outdoor table and BBQ * Office space * 100 Mbps WiFi * 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, shops and other stores * 5 min to the pier for Saint-Barth and Anguilla, and the taxi station

Top guest favorite

A private heated pool is featured at the edge of the terrace, offering views of the ocean and nearby islands. The clear blue water contrasts with the light-colored stone surrounding the pool, while lush greenery can be seen in the background against a clear sky.

Apartment in Little Bay

4.99 out of 5 average rating, 153 reviews

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 !

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Popular amenities for Simpson Bay Beach rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Top guest favorite

A modern villa exterior is showcased, featuring a private pool surrounded by a sleek patio. Sun loungers sit near the water, and vibrant greenery adds a touch of natural beauty. The structure's open design connects the indoor living space with the outdoors, framed by clear blue skies.

Home in Sint Maarten

5 out of 5 average rating, 38 reviews

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

Top guest favorite

The villa features a modern design with two levels, surrounded by lush greenery. An infinity pool is situated in front, with reclining chairs positioned nearby. The outdoor dining area is visible, and the expansive glass windows reflect the vibrant surroundings, inviting natural light into the space.

Home in Indigo Bay

5 out of 5 average rating, 20 reviews

Life's Good

An expansive infinity pool extends toward the horizon, blending with the vibrant blue sea. The sky is clear with a few clouds. Lush ocean waves can be seen in various shades of turquoise and azure, creating a serene and picturesque backdrop.

Home in Upper Prince's Quarter

4.94 out of 5 average rating, 18 reviews

Breathtaking view of St Barth – 8 people

A rooftop pool area is presented, featuring an infinity edge that overlooks the ocean. Comfortable lounge chairs are arranged along the pool deck, with clear blue skies and distant hills visible in the background. The tranquil water reflects the sunlight, creating a serene ambiance.

Home in Simpson Bay

4.92 out of 5 average rating, 12 reviews

Townhouse Villa LX

An open-air lounge area features comfortable seating with accent cushions in red. A coffee table is placed in the center, surrounded by tropical greenery. Large sliding doors lead to a view of the lagoon and ocean, with an infinity pool visible in the background.

Home in Les Terres Basses

5 out of 5 average rating, 11 reviews

Slowlife - Villa Wellness 4 beds

The villa is presented from an elevated angle, showcasing a private pool surrounded by a sleek patio. Large glass doors provide a view of the inviting interior, while sun loungers are placed alongside the pool, integrating seamlessly with the lush surroundings.

Home in Lowlands

4.74 out of 5 average rating, 122 reviews

SEA TRUE VILLA,Lavish,Sea view near Maho&Mulletbay

Top guest favorite

A private swimming pool with a unique shape is visible, surrounded by a spacious patio area. Sun loungers are placed nearby under a large white umbrella. Lush greenery and palm trees frame the scene, with the turquoise waters of Great Bay in the background.

Home in Philipsburg

5 out of 5 average rating, 27 reviews

2 Bedroom Ocean Front Villa, Private Infinity Pool

An inviting terrace features a private swimming pool with clear water, overlooking the shimmering sea and coastline. A barbecue grill is positioned beside the pool, with a view of the lush landscape and azure waters stretching into the horizon.

Home in Indigo Bay

4.83 out of 5 average rating, 185 reviews

Préstige - Luxurious 3 bedroom by the Beach

Condo rentals with a pool

The image displays a well-equipped kitchen with wooden cabinetry and white tile countertops. A set of stairs leads to the upper level, while a cozy living area is visible with a dark sofa and a large wall clock. Natural light illuminates the space.

Condo in Lowlands

4.74 out of 5 average rating, 101 reviews

Loft Condo - STEPS FROM BEACH!

A tranquil outdoor pool is surrounded by palm trees and offers a clear blue water surface. The pool area features a paved deck with lounge chairs and is set against a backdrop of multi-roofed residences.

Condo in Collectivity of Saint Martin

5 out of 5 average rating, 34 reviews

Waterfront, beautiful ELBA! 2 to 4 people

Top guest favorite

A sparkling blue pool is set against a backdrop of vibrant clouds and clear skies, with the tranquil ocean visible in the distance. Surrounding the pool, a sunbathing area with lounge chairs invites relaxation under the sun.

Condo in Saint Martin,Guadeloupe

5 out of 5 average rating, 51 reviews

Villa Belharra, amazing view

Top guest favorite

A private terrace features a comfortable seating area with soft cushions, surrounded by lush tropical plants. Beyond, white sand leads to the beach, framed by palm trees under a bright blue sky with scattered clouds.

Condo in Collectivité de Saint-Martin

5 out of 5 average rating, 24 reviews

New "Coco Beach" 2 bedrooms beachfront

A living area features a modern television mounted on a minimalist white console. A circular coffee table sits below, accompanied by a decorative shell. Light filters through sheer curtains, illuminating the space and offering a glimpse of the outdoor area.

Condo in Marigot

4.93 out of 5 average rating, 54 reviews

Beachfront Condo| Pool View + Private Beach Access

A spacious bedroom features a large bed centered against a light grey wall. Natural light enters through sliding glass doors, which lead to an outdoor space. Wooden furniture includes a minimalist desk and bedside tables, while warm tones enhance the welcoming ambiance.

Condo in Maho Beach

5 out of 5 average rating, 7 reviews

Maho Vibes Condo

Top guest favorite

A balcony is presented with two yellow chairs and a small table, set against a backdrop of a sparkling blue sea dotted with sailboats. Lush green plants add a touch of nature, and a clear blue sky creates a bright and open atmosphere.

Condo in Marigot

5 out of 5 average rating, 27 reviews

New studio with superb view of the Caribbean Sea

A spacious bedroom features a large window offering panoramic views of the ocean and nearby mountains. Two elegant chairs sit beside a small table, with a tray holding beverages and snacks placed on the bed. Natural light fills the room, creating a bright atmosphere.

Condo in Simpson Bay

4.95 out of 5 average rating, 19 reviews

Beacon Hill Hideaway: Luxury Condo in Simpson Bay

Other vacation rentals with a pool

A comfortable outdoor seating area is featured, consisting of a white sectional sofa and individual chairs, all accented with red cushions. A small table sits in the center, surrounded by lush greenery and a view of the beach in the background.

Apartment in SAINT MARTIN

5 out of 5 average rating, 18 reviews

"Black Pearl"

Top guest favorite

The living area features floor-to-ceiling windows offering panoramic views of the lagoon and mountains. A comfortable blue sofa is complemented by textured cushions, with a cozy brown armchair nearby. A round table sits in the center, showcasing a remote control and decorative elements.

Apartment in Lowlands

5 out of 5 average rating, 61 reviews

Gorgeous 2 bedroom-17th floor, Fourteen Mullet Bay

A bright living area features large windows that allow natural light to fill the space, offering views of the outdoors. A comfortable gray sofa is positioned near a round dining table with four chairs. Decorative elements, including a small centerpiece and a television, complete the inviting setting.

Apartment in Lowlands

4.87 out of 5 average rating, 23 reviews

Stunning Gem in Prime Location

A bright swimming pool offers a clear blue surface, surrounded by a sun patio with lounge chairs arranged along the edge. Palms sway gently in the background, with modern villas visible beyond the pool area.

Apartment in Saint Martin

4.96 out of 5 average rating, 68 reviews

On the beach! Villa Marina pool splendid view

Top guest favorite

A spacious terrace is complemented by a dining table surrounded by four chairs. A comfortable seating area with two wooden chairs and a couch is visible. Large glass windows provide a view of the lagoon and the outdoors, enhancing the natural light in the space.

Apartment in Marigot

5 out of 5 average rating, 8 reviews

NEW 1BR apt lagoon & sunset view 4/5p

An outdoor infinity pool is surrounded by wooden decking and landscaped greenery, providing a serene setting. Sun loungers are positioned nearby, offering views of the Caribbean Sea and the hillside landscape in the background under a clear blue sky.

Apartment in Cole Bay

4.85 out of 5 average rating, 33 reviews

A101 - Outstanding Lagoon View & Garden

Top guest favorite

A private pool surrounded by a wooden deck is featured, offering views of the turquoise ocean and nearby islands. Comfortable lounge chairs and a hammock are positioned for relaxation, while swaying palms provide a natural ambiance under the clear blue sky.

Villa in Cul-de-Sac

5 out of 5 average rating, 46 reviews

Only Villa with private beach Beach Villa Cala Mar

Loft in Sandy Ground

4.93 out of 5 average rating, 29 reviews

Love beach loft

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