Vacation rentals in Cay Bay Hill

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Top-rated vacation rentals in Cay Bay Hill

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

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Guest favorite

Villa in Indigo Bay

4.95 out of 5 average rating, 58 reviews

Villa Ocean - Indulge Yourself in Paradise

A three-bedroom, two-bathroom beauty overlooking beach/vast views of the ocean in Indigo Bay. Sunset viewing on the deck, private pool or down to the beach 10 min by walking. 10 min to airport, night life, other popular beaches. Close to town. groceries, restaurants. All the bedrooms have a view of beach and the ocean. There is free wireless internet, TV, air conditioning, a dishwasher, refrigerator, microwave, wine refrigerator, coffee maker, washer dryer, outdoor gas grill and private parking.

Guest favorite

Home in Sint Maarten

5 out of 5 average rating, 20 reviews

Luxury Villa "Villamour" w/ Private Pool

Villamour is a brand new, multilevel 5 bed, 4.5 bath villa overlooking the Caribbean Sea. You can watch boats and cruise ships sail by from the comfort of your private pool and patio. The villa was decorated by a top interior designer in South Florida. It is modern, chic, and inviting. It is only a 5 min walk to the beach and a short drive to restaurants, nightlife, supermarkets, & shopping. Top chef available for booking. This is an ideal spot for a romantic getaway or a group/family vacation.

Guest favorite

Rental unit in Simpson Bay

5 out of 5 average rating, 191 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

Guest favorite

Rental unit in Oyster Pond

4.88 out of 5 average rating, 110 reviews

Lovely Studio Apartment with Pool & Nature Views!

Take a break and unwind at this peaceful studio apartment, perfect for your Caribbean getaway! This fully equipped studio is located just 7-10 minutes away from the capital, Philipsburg, and a few minutes away from several beautiful beaches. It also has gorgeous scenic views and an inviting and relaxing pool! As well as a rooftop terrace with scenic 360 views. Baby crib and grill available upon request for small fee and washer & dryer available on premise for free use.

Guest favorite

Villa in Little Bay

4.94 out of 5 average rating, 47 reviews

Luxury 1 bedroom at VILLA KIMON + AMAZING PATIO!

Villa Kimon is the largest and most spectacular villa overlooking Great Bay harbor. Your beautiful 1 bedroom apartment with all the amenities of home awaits your arrival. A fully equipped kitchen, laundry room and beautiful large deck where you will have unrestricted panoramic views of Philipsburg, Great Bay Harbor, the Cruise terminal are all part of this property. Shopping, beaches, restaurants, water sports and other activities are within walking distance.

Guest favorite

Villa in Sint Maarten

5 out of 5 average rating, 13 reviews

Beach-Private Pool-2 Master King Bedrooms

Get away from your everyday stress and let the breathtaking views of the Caribbean Sea wash it all away as you enjoy the incomparable blue hues of the sea. Unwind in two sublime master suites, each boasting an inviting king-size bed and private bathrooms where you can melt away your worries like never before. Slip into total relaxation with every dip in a heated pool within a breathtaking courtyard—all at your own leisure!

Guest favorite

Rental unit in Little Bay

4.98 out of 5 average rating, 129 reviews

Stunning 2 BD Ocean View - Terraces Lt Bay

Treat yourself to the utmost stylish and modern ocean view apartment located in the exclusive Little Bay Hill . This spacious environment, is designed to be enjoyed as a family, has a terrace with stunning sea views, private pool, one master suites ( Japanese king bed and a walking closet), one bedroom suite with two twin size beds ( could be converted to king size bed ) . Welcome to Terraces Little Bay !

Guest favorite

Rental unit in Indigo bay

4.94 out of 5 average rating, 82 reviews

Independent low villa apartment - Indigo Bay

Villa Stella's apartment welcomes you in a unique setting with spectacular views of the Caribbean Sea. Located in a 24-hour secure residence, tranquility is at the rendezvous. You will be just an 8 min walk to Indigo Bay beach and close to shops and restaurants in the Dutch part. Consisting of 2 bedrooms and 2 bathrooms, you can relax in the pool/hot tub overlooking the bay .

Superhost

Guest suite in Simpson Bay

4.81 out of 5 average rating, 194 reviews

MYRIEL — Perfect Location/Nightlife/Beach

This Duplex 1 Bed apt is all about LOCATION. Nicest/Safest area of St.Maarten. Few steps from Simpson beach, Maho Beach nightlife/restaurants. 5-10mn walk on the beach to Karakter Beach bar and Sunset Beach Café. Very clean. Perfect for single or couple. Sleep up to 3 with sofa bed.. Private entrance, full kitchen, Stove, Microwave, A/C, WIFI, Linens and towels.

Guest favorite

Townhouse in Sint Maarten

5 out of 5 average rating, 62 reviews

Indigo Bay Villa Poolside - Ocean 14

Experience refined Caribbean living in this enchanting 2-bedroom villa, nestled within the exclusive Indigo Bay community of St. Maarten. This beautifully designed villa offers a perfect blend of comfort, style, and outdoor elegance, making it an ideal retreat for those seeking tranquility and luxury.

Guest favorite

Villa in Philipsburg

4.98 out of 5 average rating, 250 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.

Superhost

Guesthouse in Little Bay

4.86 out of 5 average rating, 222 reviews

Your oasis with spectacular views and private pool

Long idelness by the infinity pool. Two bedrooms each with its own bathroom and seperate toilette. A few minutes from the beach, shops and nightlife and yet in a quiet and safe area. The guests has the entire home with a private pool. Please check “villa_pi” on instagram for more photos