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Condo vacation rentals in Simpson Bay

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Top-rated condo rentals in Simpson Bay

Guests agree: these condos are highly rated for location, cleanliness, and more.

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Top guest favorite
A spacious daybed is shaded by a wooden pergola, surrounded by vibrant greenery. The beach and ocean serve as a backdrop, with gentle waves lapping at the shore. Colorful cushions and a soft blanket add comfort, while a small Buddha statue creates a serene ambiance.
Condo in Simpson Bay
4.97 out of 5 average rating, 95 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

Guest favorite
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, 180 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 living area is depicted, featuring a light-colored sectional sofa and two armchairs facing a flat-screen television. Natural light fills the room through large sliding doors that open to a garden view, complemented by tasteful indoor plants and soft furnishings.
Condo in Simpson Bay
4.99 out of 5 average rating, 73 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.

Guest favorite
A spacious bedroom features a large bed adorned with white linens and a soft gray throw. Three framed black-and-white prints are displayed on the wall above the bed, while a window offers views of the beach and ocean beyond.
Condo in Lowlands
4.92 out of 5 average rating, 132 reviews

Modern Oceanview 2-Bedroom Condo on Mullet Bay

Welcome to Fourteen, one of the most luxurious beachfront residences in St Maarten located directly on the famous Mullet Bay beach and golf course. Located on the 9th floor, You will find this spacious 2 bedroom condo offering beautiful ocean views, great for a group, family, or romantic getaway. Indulge yourself in all of the amenities, outstanding concierge services and dining experience Fourteen has to offer. We aim to make your stay unforgettable. $5 per night resort fee not included

Top guest favorite
A large private pool is framed by vibrant greenery and colorful flowers. Sun loungers line the pool area, and a cruise ship is visible in the distance along the ocean, with the picturesque shoreline beyond.
Condo in Lowlands
4.9 out of 5 average rating, 50 reviews

Maho 1 Bed Condo with ocean view & Free Wi-Fi

Our cozy 1 Bed 1 Bath condo has a view from the balcony of the ocean and the famous Maho Beach . Two air conditioning units (common area and bedroom) are separately controlled for everyone's comfort. There is FREE HIGH SPEED FIBER WIFI in this unit, an IN-UNIT washing machine and beachy rattan furniture. You have access to the large private pool on the complex and the front desk reception provides free towel service. This building has a generator in case of any island power outages

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
4.95 out of 5 average rating, 124 reviews

Saint 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...

Top guest favorite
A well-maintained outdoor pool is surrounded by lounge chairs, offering a relaxing space for guests. Shade is provided by large umbrellas, and tropical palm trees are visible in the background. The pool area is complemented by modern residential buildings, enhancing the serene environment.
Condo in Lowlands
4.98 out of 5 average rating, 85 reviews

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.

Guest favorite
A light-filled living space features a comfortable beige sofa set, complemented by natural wood accents. Large windows provide a view of the ocean, while a doorway opens to an outdoor space adorned with greenery. Simple decor enhances the tranquil atmosphere of the room.
Condo in Simpson Bay
4.96 out of 5 average rating, 84 reviews

Hamaka condo, a beachfront retreat on Simpson Bay

Escape to the ultimate beachfront retreat at Hamaka, a fully equipped condo recently renovated to offer the perfect private beach escape with easy walking distance access to restaurants, bars, and nightly entertainment in Simpson Bay, Saint-Martin. Experience waking up to the sound of the waves and having your morning drink to the sight of the endless shades of the ocean. At the end of your day, unwind and enjoy the magnificent sunsets that this beautiful island has to offer.

Top guest favorite
Condo in Maho
4.91 out of 5 average rating, 226 reviews

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.

Top guest favorite
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
4.95 out of 5 average rating, 133 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 favorite
A neatly arranged bed with plush pillows is complemented by two rolled towels placed artistically in the foreground. A vibrant flower and small treats are positioned nearby. A modern lamp and a sofa adorned with colorful cushions are visible in the background.
Condo in Lowlands
4.81 out of 5 average rating, 149 reviews

Convenient Studio Apt Near Airport, Beaches & Food

This beautiful studio apartment is located in the newly built Jordan Village complex which is a convenient 10 minute drive away from the Juliana International Airport and is directly opposite the American University of the Caribbean (AUC) Medical School. Guests have the comfort of having the entire living space to themselves with free and accessible parking while having access to two convenient stores, restaurants, bars, beaches, and nightlife.

Top guest favorite
Condo in Collectivity of Saint Martin
5 out of 5 average rating, 18 reviews

Villa Bora Bora - Beach and Caribbean Sea

Stunning views of the Caribbean Sea, directly on the beach, overlooking a palm garden and the pool. Carefully decorated and fully equipped villa, air-conditioned, with a water reserve for your comfort. Located in a private, quiet, and secure residence with 4 swimming pools, 2 tennis courts, and private parking. Close to shops, restaurants, bakery, pharmacy, rotisserie, and car rental. Enjoy your meals on a large terrace with an electric awning.

Popular amenities for Simpson Bay condo rentals

When is the best time to visit Simpson Bay?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$59,807 GYDG$56,880 GYDG$59,180 GYDG$44,124 GYDG$39,732 GYDG$42,032 GYDG$44,542 GYDG$41,614 GYDG$37,641 GYDG$37,641 GYDG$40,987 GYDG$49,561 GYD
Avg. temp26°C26°C26°C27°C28°C29°C29°C29°C29°C29°C28°C27°C

Quick stats about condo rentals in Simpson Bay

  • Total vacation rentals

    Explore 90 vacation rentals in Simpson Bay

  • Nightly prices starting at

    Simpson Bay vacation rentals start at G$20,912 GYD per night before taxes and fees

  • Verified guest reviews

    Over 3,420 verified reviews to help you choose

  • Family-friendly vacation rentals

    50 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Vacation rentals with a pool

    70 properties feature pools

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

  • Wi-Fi availability

    90 of Simpson Bay vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Simpson Bay rentals

  • 4.9 Average rating

    Simpson Bay stays are highly rated by guests—averaging 4.9 out of 5!