Vacation rentals in Sile Bay

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Top-rated vacation rentals in Sile Bay

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Guest favourite

Condo in Simpson Bay, Sint Maarten

5.0 out of 5 average rating, 56 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

Aug. 29 – Sep. 5

$906 CAD per night

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.

Sep. 23 – 30

$1,247 CAD per night

Guest favourite

Home in Island Harbour, Anguilla

5.0 out of 5 average rating, 5 reviews

Oceanfront Villa With Pool Jacuzzi Near Shoal Bay

Your 2 bedroom oceanfront villa includes a private pool, hot tub & breathtaking caribbean views of Scilly Cay, Island Harbor. 5 minute drive to Shoal Bay. One of a kind sunrises from oceanfront terraces. Wake up to endless Caribbean turquoise views from the master King Bed. Relax on the spacious lower and upper decks . Take a dip in the pool or sea. Outdoor shower. Access additional club pool, common area and fire pit. Perfect for a family or romantic getaway. Welcome to Arawak Beach Villa.

Aug. 17 – 24

$613 CAD per night

Superhost

Home in Shoal Bay Village, Anguilla

4.92 out of 5 average rating, 13 reviews

Shoal Bay Coastal Sanctuary, Anguilla

Shoal Bay Coastal Sanctuary is located directly on the coast with beautiful unobstructed views of the sea. It's a gracious two story home of 3 bedrooms and 3 full bathrooms--the lower level is comprised of 2 bedrooms on either side of an open plan "kitchen / dining room / living room" with the penthouse bedroom on the upper level. All rooms face onto the Caribbean and overlook the freshwater pool--every room is fully screened and air conditioned and graciously decorated in a Caribbean motif.

Jul. 28 – Aug. 4

$862 CAD per night

Guest favourite

Home in Shoal Bay, Anguilla

5.0 out of 5 average rating, 13 reviews

Harmony at Bayview Homes

Harmony, our largest home, commands 4260 sq ft of space and features 3 bedrooms each with a king bed, balcony, ensuite bathroom, walk-in closet, air-conditioning, and wifi. In addition to this, there are 3 shared living spaces, a dining room, 6 balconies, a fully equipped kitchen, smart TVs, washing machine, dryer and expansive outdoor space for entertaining. ‍ Wether traveling as a group of friends, multiple couples, or as a family, Harmony is the perfect place with lots of room for fun!

Mar. 26 – Apr. 2

$617 CAD per night

Guest favourite

Apartment in Simpson Bay, Sint Maarten

5.0 out of 5 average rating, 171 reviews

The Beach House Apartment

A stylishly modern one bedroom apartment directly located on the beautiful white sand beach of Simpson Bay. Enjoy the crystal clear waters by day and explore the Caribbean charm of our bustling nightlife. Our island getaway provides you with the full relaxation experience complete with beach chairs, umbrellas, outdoor shower, snorkel gear and paddle boards to complete beach side experience Amenities include free WIFI, kitchen, king size bed, beach chairs, umbrella's and much more

Oct. 5 – 12

$432 CAD per night

Guest favourite

Apartment in The Quarter, Anguilla

5.0 out of 5 average rating, 22 reviews

Thrush Nest View Studio Apartment

Forget your worries in this spacious and serene studio apartment designed for relaxation after a long day at the beach . Kick your feet up while enjoying a cup of coffee to the sunrise or a glass of wine to the sunset as this space provides panoramic views from every angle. Located in the centre of the island this vacation apartment is the ideal platform for exploring beaches, island tours and extraordinary dinning. Contemporary decor with modern amenities all can enjoy.

Jul. 14 – 21

$183 CAD per night

Guest favourite

Apartment in East End Village, Anguilla

5.0 out of 5 average rating, 26 reviews

C&J Apartments overlooking Mimi Bay Beach (Apt 2)

Enjoy Anguilla while staying in a spacious 2 bedroom unit, which is apart of a 2 bedroom 4 unit apartment complex. It was designed and is maintained by the hosts. Each room is tastefully decorated to ensure a calming experience. Pictures add to the decor some featuring the work of the talented artist, Canita Ruan, the hosts' daughter. Ceiling fans are in each room, but you may not need them as the area is pretty cool. The area is very quiet. "Your Home Away From Home"

Oct. 13 – 20

$133 CAD per night

Guest favourite

Apartment in Mount Fortune, Anguilla

5.0 out of 5 average rating, 45 reviews

Fortune Estate (Car rental available)

Newly built modern cozy apartment with remote gate access, back up generator and perimeter security camera system located in Mount Fortune on the eastern end of the island. Five minutes driving access to grocery stores, Island Harbour beach and the restaurants thereon like Falcon Nest. 10 minutes drive from the famous Shoal Bay beach.

Dec. 17 – 24

$187 CAD per night

Guest favourite

Cottage in Cul-de-Sac, St. Martin

4.98 out of 5 average rating, 101 reviews

VILLA JADE 2: WATERFRONT/ POOL

VILLA JADE is a complex of 3 villas located in THE BAY OF ASS DE SAC and its islets ... VILLA JADE 2 is a spacious suite/sea view for 2 people seafront, with private pool. The 3 villas are adjoining but very quiet and intimate. Your only view is the sea... Direct access to the sea by a pontoon, and kayaks at your disposal.

Apr. 8 – 15

$488 CAD per night

Guest favourite

Villa in Philipsburg, Sint Maarten

4.99 out of 5 average rating, 224 reviews

Villa Dream View Belair Sint Maarten SXM

Embrace the tranquility in a friendly tropical caribbean modern designed private villa with spacious rooms that are sure to keep you comfortable and feeling at home. Enjoy the sunny day with infinity pool overlooking caribbean sea or enjoy the sea view while watching the sailing huge cruise ships.

Oct. 19 – 26

$657 CAD per night

Superhost

Apartment in Bad Cox Pond, Anguilla

4.88 out of 5 average rating, 17 reviews

The Studio at AXA Farmhouse

Welcome to your tranquil retreat at AXA Farmhouse. This private studio offers a serene getaway, complete with a fully equipped kitchen, a spa-inspired bathroom, and a separate entrance for your convenience. Rest easy on a plush bed, and enjoy the comfort of air conditioning throughout your stay.

May 2 – 9

$162 CAD per night