A calm lake with several boats anchored, surrounded by hills and a cloudy sky.

Cay Bay Hill Vacation Rentals

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Our top choices for Cay Bay Hill vacation rentals

1. condostmaarten by the sea -Adults Only-

condostmaarten by the sea -Adults Only-
4.0 star property
Indigo Bay
9.2 out of 10, Wonderful, (43 reviews)
"Love love the property was amazing. Will definitely return."
United States
Muneca
The price is CA $423
CA $625 total
includes taxes & fees
Oct 14 - Oct 15
condostmaarten by the sea -Adults Only-

2. Modern Indigo Bay Studio – 3 Min Walk To Beach!

Modern Indigo Bay Studio – 3 Min Walk To Beach!
Indigo Bay
9.0 out of 10, Wonderful, (2 reviews)
"Beautiful unit, great view, everything fantastic!"
United States
Joseph K.
The price is CA $231
CA $449 total
includes taxes & fees
Sep 20 - Sep 21
Modern Indigo Bay Studio – 3 Min Walk To Beach!

3. Luxury 4BR Villa w/ Private Pool & Ocean Views

Luxury 4BR Villa w/ Private Pool & Ocean Views
Indigo Bay
10.0 out of 10, Exceptional, (1 review)
"This property has a breathtaking view and is in the perfect location—close to stores and just minutes from the beaches.Fritz, the host, was amazing! The island had just gone through a major storm the day before we arrived, and despite the circumstances, Fritz was always available and ready to help with anything we needed. He even offered us an extra day to make up for any inconvenience, which was so thoughtful and appreciated.I would absolutely stay here again and would highly recommend this...
United States
Ms Light T.
The price is CA $771
CA $1,765 total
includes taxes & fees
Oct 7 - Oct 8
Luxury 4BR Villa w/ Private Pool & Ocean Views

4. Villa Solandra – 3BR Oceanfront Sunset w/ Pool

Villa Solandra – 3BR Oceanfront Sunset w/ Pool
Indigo Bay
10.0 out of 10, Exceptional, (1 review)
"Our stay at Villa Solandra was nothing short of amazing. The check in process was seamless, the communication with the host was always smooth and timely, the villa itself was beautiful. It was clean, great location, and the view is insane. This place was part of the reason we had such a memorable time in St. Maarten. "
United States
Olivia G.
The price is CA $582
CA $1,238 total
includes taxes & fees
Sep 29 - Sep 30
Villa Solandra – 3BR Oceanfront Sunset w/ Pool

5. Hilton Vacation Club Royal Palm St. Maarten

Hilton Vacation Club Royal Palm St. Maarten
4.0 star property
Simpson Bay
9.0 out of 10, Wonderful, (1,298 reviews)
"Perfect location."
United States
Andre
The price is CA $201
CA $248 total
includes taxes & fees
Oct 4 - Oct 5
Hilton Vacation Club Royal Palm St. Maarten

6. July Apartments

July Apartments
3.0 star property
Madame's Estate
9.0 out of 10, Wonderful, (253 reviews)
"The property was no frills and the staff super helpful. Would stay again!"
United States
JoyAnn Carolyn
The price is CA $130
CA $136 total
includes taxes & fees
Sep 21 - Sep 22
July Apartments

7. The Hills Residence

The Hills Residence
3.0 star property
Simpson Bay
8.4 out of 10, Very good, (169 reviews)
"Very good"
United States
Alyssia
The price is CA $218
CA $379 total
includes taxes & fees
Oct 6 - Oct 7
The Hills Residence

8. Simpson Bay Suites

Simpson Bay Suites
3.5 star property
Simpson Bay
7.2 out of 10, Good, (165 reviews)
"Overall good. Location is great."
Canada
Manishkumar
The price is CA $170
CA $190 total
includes taxes & fees
Sep 19 - Sep 20
Simpson Bay Suites

9. MIDTOWN MOTEL SXM

MIDTOWN MOTEL SXM
2.5 star property
Downtown Philipsburg
7.4 out of 10, Good, (73 reviews)
"It was a wonderful stay and experience"
United States
Yollanda
The price is CA $93
CA $114 total
includes taxes & fees
Sep 29 - Sep 30
MIDTOWN MOTEL SXM

10. The Castle ᴷ

The Castle ᴷ
Downtown Philipsburg
10.0 out of 10, Exceptional, (1 review)
The price is CA $168
CA $209 total
includes taxes & fees
Oct 14 - Oct 15
The Castle ᴷ

11. Mullet Bay Suites: Your Luxury Stay Awaits

Mullet Bay Suites: Your Luxury Stay Awaits
4.0 star property
Maho
9.6 out of 10, Exceptional, (184 reviews)
"This place was amazing. Perfect experience"
United States
Kenneth
The price is CA $347
CA $492 total
includes taxes & fees
Oct 7 - Oct 8
Mullet Bay Suites: Your Luxury Stay Awaits

12. The Castle ᴶ

The Castle ᴶ
Downtown Philipsburg
10.0 out of 10, Exceptional, (1 review)
"Host was welcoming and the apartment was very clean and inviting. We will Definitely stay here again when we come back. "
United States
Neil C.
The price is CA $168
CA $209 total
includes taxes & fees
Sep 27 - Sep 28
The Castle ᴶ

13. Beach Front Studio C3

Beach Front Studio C3
Simpson Bay
8.8 out of 10, Excellent, (5 reviews)
"Really cool place and the location was prime. The cleaning lady was the nicest person there could be as well. "
Canada
Benjamin
The price is CA $138
CA $208 total
includes taxes & fees
Sep 20 - Sep 21
Beach Front Studio C3

14. Beach Front 1 Bedroom Flat D3

Beach Front 1 Bedroom Flat D3
Simpson Bay
10.0 out of 10, Exceptional, (3 reviews)
"Great location near Simpson Bay restaurants and nightlife. Accommodations were exactly as pictured with modern furnishings. Car rental is recommended to fully enjoy the island. "
United States
Christopher
The price is CA $175
CA $248 total
includes taxes & fees
Sep 20 - Sep 21
Beach Front 1 Bedroom Flat D3

15. The Castle f

The Castle f
Downtown Philipsburg
8.0 out of 10, Very good, (1 review)
"After a bit of confusion about checking in, we arrived and after that everything was great. It was a surprise to find the window was onto a corridor, but the air con was good so no need to open a window, and also helped to make the room quiet."
United Kingdom
Pat R.
The price is CA $168
CA $209 total
includes taxes & fees
Sep 20 - Sep 21
The Castle f

16. The Castle ᴵ

The Castle ᴵ
Downtown Philipsburg
10.0 out of 10, Exceptional, (1 review)
The price is CA $189
CA $232 total
includes taxes & fees
Sep 20 - Sep 21
The Castle ᴵ

17. Cozy flat on the boardwalk!

Cozy flat on the boardwalk!
Downtown Philipsburg
10.0 out of 10, Exceptional, (2 reviews)
"Host was very accommodating and helpful. Amenities were abundant."
United States
Robert H.
The price is CA $189
CA $285 total
includes taxes & fees
Sep 19 - Sep 20
Cozy flat on the boardwalk!

18. Blue Sail Apartments - Double room

Blue Sail Apartments - Double room
Pelican Key
2.0 out of 10, (1 review)
The price is CA $144
CA $156 total
includes taxes & fees
Sep 20 - Sep 21
Blue Sail Apartments - Double room

19. The Castle L - Twin Studio

The Castle L - Twin Studio
Downtown Philipsburg
The price is CA $168
CA $209 total
includes taxes & fees
Sep 20 - Sep 21
The Castle L - Twin Studio

20. The Castle ᴳ

The Castle ᴳ
Downtown Philipsburg
The price is CA $168
CA $209 total
includes taxes & fees
Sep 22 - Sep 23
The Castle ᴳ
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Cay Bay Hill Hotel Reviews

Find out more about Cay Bay Hill

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Cay Bay Hill. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a vacation rental in Cay Bay Hill?

Yes, we offer vacation rentals close to top points of interest in Cay Bay Hill, or you can select a more remote option if you're looking for relaxation.

What are some of the best vacation rentals that Cay Bay Hill has to offer?

Philips Scott House Calinago: You might want to consider this vacation rental near Cay Bay Hill, which is in a shopping district and equipped with air-conditioning and WiFi to help you feel perfectly comfortable in your new surroundings. Amenities like a microwave and free parking are also available for your convenience.

How many vacation rentals are there in Cay Bay Hill?

Choose from 3 Expedia vacation rentals in Cay Bay Hill for a memorable vacation.

What can I see and do in Cay Bay Hill?

While you're exploring the area, Maho Beach and Little Bay Beach are a couple of picturesque spots to get outside and enjoy nature. Great Bay Beach and Hollywood Casino are a couple of places you'll find in the larger area.

What are vacation rentals like in Cay Bay Hill?

Vacation rentals are privately owned properties you can reserve for a short or long stay in Cay Bay Hill. Vacation rentals feature extras like kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, vacation rentals can provide a sense of privacy away from shared hotel elevators and busy front desks while still allowing you to travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive choice for families.