Villa vacation rentals in Simpson Bay

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Top-rated villa rentals in Simpson Bay

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Guest favorite

Villa in Pelican Key, Sint Maarten

5.0 out of 5 average rating, 16 reviews

Villa Sea Forever @ Pelican Key - Paradise Awaits!

Experience a piece of paradise at "Villa Sea Forever" in Pelican Key, Simpson Bay, Sint Maarten! This top floor, 2-bedroom, 2.5-bathroom haven offers mesmerizing, panoramic ocean & sunset views. Dive into pure bliss with a pool, gated community, private parking space, and all the comforts you need, including a full size washer & dryer, and fully stocked kitchen. Feel the breeze from your huge double balcony. Your dream escape awaits at "Villa Sea Forever" where breathtaking moments are endless!

Oct 27 – Nov 3

$200 per night

Guest favorite

Villa in Upper Prince's Quarter, Sint Maarten

5.0 out of 5 average rating, 36 reviews

EXQUISITE 5-STAR BEACHFRONT VILLA

SPECIAL: MARCH 18-30 @ $800/NIGHT Guaranteed to create a 5-Star experience! Fully air-conditioned 3 BR, 3 1/2 bath Beachfront Villa w/private pool. If you love the ocean & spectacular views, but fine living & comfort are important to you, we have it all! My home offers Personal housekeeper, Private Chef for hire, full Concierge Service, private garage, and gym. Also, food and groceries delivered prior to your arrival, access to all the services and amenities next door at the Oyster Bay Hotel.

Aug 24 – 31

$880 per night

Guest favorite

Villa in Upper Prince's Quarter, Sint Maarten

4.96 out of 5 average rating, 99 reviews

The Blue Door Villa - 4 bed ocean view home

Welcome to The Blue Door Villa where 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 to help plan your vacation.

Aug 2 – 9

$795 per night

Guest favorite

Villa in Indigo Bay, Sint Maarten

4.95 out of 5 average rating, 100 reviews

Villa Life is Good

Sint Maarten Indigo Bay: One whole villa to yourself at 10 minutes from Princess Julianna airport the Villa "Life is Good" with infinity pool is located on the mountainside with a 180 degree view of the sea. View of the Islands, Saba, St Kitts & Nevis and Sint Eustatius. A spectacle of breathtaking sunrises and sunsets. Far from the noise and hustle of the city, you will find peace and quiet guaranteed. You will find 5 minutes drive from the villa: beaches, restaurants and all amenities.

Nov 5 – 12

$525 per night

Guest favorite

Villa in Upper Prince's Quarter, Sint Maarten

5.0 out of 5 average rating, 22 reviews

Villa Blue Roc

Cette villa luxueuse , est situee dans une residence securisee avec une vue epoustouflante , face a l ocean et l ile de St Barthelemy, Perchee sur les hauteurs de Dawn Beach, a 15 minutes des fameuses plages/restaurants d Orient Bay et Grand Case en partie francaise. La villa est egalement a 5 minutes de la capital hollandaise , Philipsburg, un incontournable du shopping. Grace aux grands espaces exterieurs et a la piscine a debordement , cette villa vous offrira un sejour inoubliable.

Feb 27 – Mar 6

$710 per night

Guest favorite

Villa in Koolbaai, Sint Maarten

5.0 out of 5 average rating, 20 reviews

3 Bed & 3 Bath Villa Domila with Private Pool SXM

Villa Domila is gorgeous and spacious with a modern Caribbean look. She is perfectly located in the private community of Pelican Key. The Simpson Bay busy hub is only a couple minutes but you will still feel like you have your own secluded piece of paradise. The views from the deck and pool oversee the gorgeous Simpson Bay. The Villa receives sun all day and is witness to amazing sunsets over the sea. The villa is not shared with other guests and it is completely private.

Sep 29 – Oct 6

$363 per night

Guest favorite

Villa in Oyster Pond , Sint Maarten

5.0 out of 5 average rating, 32 reviews

Ultra Modern Tropical Villa w. stunning sea views

Villa Helios overlooks the Ocean with 210 degree views, including St. Barts. Views from every room. Private and secure, the villa is suitable for an extended family or three/four couples - rooms are well separated. The wind provides a steady cooling breeze on the Atlantic side of the island. Open the sliding door in the morning and enjoy the topical breeze all day. Located on the prestigious quiet and peaceful Plateau, a small gated community of only 6 homes.

Apr 22 – 29

$695 per night

Guest favorite

Villa in Collectivity of Saint Martin, St. Martin

5.0 out of 5 average rating, 39 reviews

VILLA I LOVE View-villa luxe avec vue mer

Villa I LOVE VIEW is an oasis of tranquility – with its private swimming pool (naturism possible), large terrace and luxurious kitchen space. Come and discover its view of multiple shades of blue while relaxing on the deckchairs by the pool with Zen natural stone glare Located in Cul de Sac, facing Saint Barth , Pinel Island and Baie Orientale. Close to the most beautiful beaches of the island, restaurants, water entertainment, it is the perfect place for your vacation.

Apr 18 – 25

$377 per night

Superhost

Villa in Simpson Bay, Sint Maarten

4.84 out of 5 average rating, 37 reviews

Modern 2 bedroom luxury beachside villa with pool

Your own private paradise. Modern 2 bedroom luxury villa in safe gated community with security. New appliances with air conditioning, WIFI, security cameras, and secured free parking including Smart TV with free NetFlix, HBO Max, and Prime access. Private pool with adjacent outdoor dining/lounge area. Perfect for families or couples. Maid and private chef service available if needed. Walking distance from dining, night clubs, and shopping. Steps away from the beach.

Mar 12 – 19

$390 per night

Superhost

Villa in Sint Maarten, Sint Maarten

4.84 out of 5 average rating, 51 reviews

Villa Indigo Dream, Indigo Bay SXM

Prepare to de-stress and to be mesmerized by the continuous influence of the sunlight and the sea throughout the villa. The villa offers a spectacular indoor-outdoor living experience which opens onto the infinity pool deck and boasts breathtaking views of the islands Saba, St. Eustatius and St.Kitts. The home defines true tranquility. Listen to the surf as sip your coffee in the morning or make a sunset toast watching nature's greatest light show over the sea.

Apr 18 – 25

$715 per night

Guest favorite

Villa in Indigo Bay, Sint Maarten

4.92 out of 5 average rating, 25 reviews

Villa Elysian: Luxurious Ocean View in Indigo Bay

Villa Elysian is a very well appointed 3 Bedroom Villa with spectacular views of the Caribbean Sea nestled in the highly sought-after neighborhood of Indigo Bay. It is very centrally located close to all SXM has to offer. A definite top-tier choice for the savvy Sint Maarten traveller. We also include a nice starter kit of Soap, Shampoo & Body Lotion in each bathroom and basics like Toilet Paper, Paper Towels, Laundry Pods and Dishwasher Detergent.

Jan 19 – 26

$653 per night

Guest favorite

Villa in Cul-de-Sac, St. Martin

4.99 out of 5 average rating, 116 reviews

VILLA JADE 1: WATERFRONT SUITE/ POOL

VILLA JADE is located in the bay of "FRENCH CUL DE SAC". It is a beachfront complex composed of 3 private villas. VILLA JADE 1 is a suite for 2 people with private pool. The villas are calm and intimate...your unique view is the sea. The bay of "FRENCH CUL DE SAC" is 5 minutes from ORIENT BAY, tourist with restaurants, bars, water activities, but also a few minutes from GRAND CASE, our small typical village with gourmet restaurants by the sea....

Sep 5 – 12

$237 per night