Villa holiday rentals in Simpson Bay

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Top-rated villa rentals in Simpson Bay

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Guest favourite

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.

10–17 Sep

$1,240 SGD per night

Guest favourite

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.

13–20 Aug

$742 SGD per night

Guest favourite

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.

19–26 Apr

$822 SGD per night

Guest favourite

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.

9–16 Dec

$747 SGD per night

Guest favourite

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.

12–19 Nov

$656 SGD per night

Guest favourite

Villa in Beacon Hill, Sint Maarten

5.0 out of 5 average rating, 11 reviews

Private Pool, Luxury Oceanfront unique Penthouse

*For stays of 7 nights or more, enjoy a free night - *This promotion cannot be combined. Offer for select dates and already included in the price. Come take advantage of this luxury property located on the end of the Beacon Hill peninsula, ensconced on all sides by the inviting Caribbean Sea! This spectacular waterfront property is one of a kind. Located just minutes from several of St. Maarten’s most popular beaches and beach bar hangouts, a great day is always guaranteed.

13–20 Dec

$1,291 SGD per night

Guest favourite

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.

27 Nov – 4 Dec

$660 SGD per night

Guest favourite

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.

6–13 Nov

$585 SGD 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.

26 Jul – 2 Aug

$487 SGD 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.

24 Sep – 1 Oct

$936 SGD per night

Superhost

Villa in Cul-de-Sac, St. Martin

4.94 out of 5 average rating, 82 reviews

VILLA JADE3: 2 BEDROOMS & POOL FEET IN THE WATER

VILLA JADE is a complex of 3 villas , right on the water. VILLA JADE is located in the quiet Baie de Cul de Sac, facing the Ilet PINEL and the turquoise nature reserve. Life is peaceful, kayak outings, lounging, BBQ with family or friends... You are 5 minutes from the fabulous Baie Orientale, its restaurants, bars and water activities... The 3 villas are adjoining but very intimate and quiet, your only view is the sea....your only goal is to " enjoy"......

17–24 Apr

$699 SGD per night

Guest favourite

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.

1–8 Dec

$1,020 SGD per night