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 Indigo Bay, Sint Maarten

5.0 out of 5 average rating, 13 reviews

Indigo Bliss Villa SXM

Welcome to the Indigo Bliss, your luxurious retreat in the heart of St. Maarten! Nestled in the exclusive community of Indigo Bay, this property promises an unforgettable Caribbean escape with breathtaking views and unparalleled comfort. Dip into the private infinity pool and feel the stress of everyday life melt away. Surrounded by tropical landscaping, the pool area is your own private oasis, perfect for basking in the sun, taking refreshing swims, or enjoying a cocktail at the poolside bar.

Apr 8 – 15

$733 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 18 – 25

$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.

May 8 – 15

$525 per night

Guest favorite

Villa in Upper Prince's Quarter, Sint Maarten

5.0 out of 5 average rating, 21 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.

Mar 1 – 8

$710 per night

Guest favorite

Villa in Cay Bay, Sint Maarten

4.98 out of 5 average rating, 65 reviews

Make your dream come true!

Overlooking the private beach of Indigo Bay, Villa Olisa is in a tropical environment with spectacular sea view; it offers a private swimming pool, marble terrace, trendy outdoor living room, outdoor dining room on the sea, equipped with a power BBQ, large indoor dining room, a large super-equipped kitchen (where you can show off your talents as a chef), 3 bedrooms with 2 Queen beds and a King bed, 2 large bathrooms with glass showers, an outdoor toilet and shower on the pool.

Nov 13 – 20

$426 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.

Dec 13 – 20

$539 per night

Guest favorite

Villa in Simpson Bay, Sint Maarten

4.98 out of 5 average rating, 41 reviews

Waterfront "BONJOUR" Beacon Hill St Maarten

This stunning 4-bedrooms, 4 bathrooms villa overlooks Maho Bay and provides a front row seat to beautiful SXM sunsets, and over the famous Maho Beach. Enjoy the views while taking a dip in the home’s infinity pool overlooking the ocean or from its multiple outdoor dining and seating options conveniently and securely located minutes from restaurants, bars, nightlife, Maho Market and more, steps away from direct beach access to the crystal clear waters of Simpson Bay.

Jul 31 – Aug 7

$774 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.

Aug 31 – Sep 7

$375 per night

Guest favorite

Villa in Oyster Pond , Sint Maarten

5.0 out of 5 average rating, 31 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.

Feb 7 – 14

$895 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 31 – Apr 7

$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.

Oct 11 – 18

$599 per night

Guest favorite

Villa in Grand Cayes, St. Martin

4.97 out of 5 average rating, 32 reviews

VILLA "ON THE SEA" , ON THE WATER...

Relax at villa ON THE SEA... Ideally located in the pretty bay of "CUL DE SAC" and its Ilets... Perfect for family holidays or friendly sharing with friends... You have: - 1 wide deck ( living room, table and chairs, BBQ, hammock, deckchairs ) - 1 swimming pool overhanging the sea - 1 access to the private pontoon/ kayaks & paddles to reach Ilet PINEL! - 3 bedrooms / 3 bathrooms - 1 cozy living room ( TV, wifi ) - 1 equipped kitchen/ laundry Join us quickly!!!

Oct 15 – 22

$468 per night