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 $429
CA $634 total
includes taxes & fees
Oct 19 - Oct 20
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 $258
CA $513 total
includes taxes & fees
Oct 22 - Oct 23
Modern Indigo Bay Studio – 3 Min Walk To Beach!

3. 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 $647
CA $1,303 total
includes taxes & fees
Oct 27 - Oct 28
Villa Solandra – 3BR Oceanfront Sunset w/ Pool

4. 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 $891
CA $1,911 total
includes taxes & fees
Nov 2 - Nov 3
Luxury 4BR Villa w/ Private Pool & Ocean Views

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, (1,319 reviews)
"The staff was very friendly"
United States
Carmelle,
The price is CA $229
CA $277 total
includes taxes & fees
Nov 5 - Nov 6
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, (254 reviews)
"The property was no frills and the staff super helpful. Would stay again!"
United States
JoyAnn Carolyn
The price is CA $152
CA $160 total
includes taxes & fees
Oct 20 - Oct 21
July Apartments

7. MIDTOWN MOTEL SXM

MIDTOWN MOTEL SXM
2.5 star property
Downtown Philipsburg
7.6 out of 10, Good, (74 reviews)
"It was a wonderful stay and experience"
United States
Yollanda
The price is CA $93
CA $114 total
includes taxes & fees
Oct 29 - Oct 30
MIDTOWN MOTEL SXM

8. The Hills Residence

The Hills Residence
3.0 star property
Simpson Bay
8.4 out of 10, Very good, (171 reviews)
"Very good"
United States
Alyssia
The price is CA $233
CA $391 total
includes taxes & fees
Oct 22 - Oct 23
The Hills Residence

9. Simpson Bay Suites

Simpson Bay Suites
3.5 star property
Simpson Bay
7.2 out of 10, Good, (168 reviews)
"Overall good. Location is great."
Canada
Manishkumar
The price is CA $192
CA $215 total
includes taxes & fees
Oct 17 - Oct 18
Simpson Bay Suites

10. 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, (185 reviews)
"This place was amazing. Perfect experience"
United States
Kenneth
The price is CA $363
CA $510 total
includes taxes & fees
Oct 17 - Oct 18
Mullet Bay Suites: Your Luxury Stay Awaits

11. Charming studio with splendid Caribbean Sea view & pool/beach access

Charming studio with splendid Caribbean Sea view & pool/beach access
Marigot
9.4 out of 10, Exceptional, (3 reviews)
"Beautiful view and the host was very welcoming."
United States
Dasha A.
The price is CA $234
CA $327 total
includes taxes & fees
Oct 25 - Oct 26
Charming studio with splendid Caribbean Sea view & pool/beach access

12. Blue Sail Apartments - Two bedroom apartments

Blue Sail Apartments - Two bedroom apartments
Pelican Key
6.0 out of 10, (3 reviews)
"Check in was seamless accommodations were exactly as expected and the staff were very friendly. We noticed many things were brand new and we were informed that there was a new owner- appears that they are working hard!"
United States
Heidi
The price is CA $172
CA $200 total
includes taxes & fees
Oct 18 - Oct 19
Blue Sail Apartments - Two bedroom apartments

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 $141
CA $226 total
includes taxes & fees
Oct 17 - Oct 18
Beach Front Studio C3

14. Lovely room in a nice villa , close to Friars bay and happy bay

Lovely room in a nice villa , close to Friars bay and happy bay
Saint-martin
9.0 out of 10, Wonderful, (11 reviews)
"Great place to stay. Will definitely be staying again next year! "
United States
Kurt
The price is CA $111
CA $172 total
includes taxes & fees
Oct 19 - Oct 20
Lovely room in a nice villa , close to Friars bay and happy bay

15. Convenient studio close to airport, beaches and food

Convenient studio close to airport, beaches and food
Maho
10.0 out of 10, Exceptional, (30 reviews)
"Wonderful stay"
Netherlands
john bracebridge w.
The price is CA $141
CA $247 total
includes taxes & fees
Oct 17 - Oct 18
Convenient studio close to airport, beaches and food

16. 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 $152
CA $239 total
includes taxes & fees
Oct 17 - Oct 18
Beach Front 1 Bedroom Flat D3

17. Hillside Penthouse spacious 2-bed/bath condo - ideal getaway but still central

Hillside Penthouse spacious 2-bed/bath condo - ideal getaway but still central
South Reward
10.0 out of 10, Exceptional, (3 reviews)
"Home away from home "
United States
Trevayne
The price is CA $160
CA $329 total
includes taxes & fees
Oct 31 - Nov 1
Hillside Penthouse spacious 2-bed/bath condo - ideal getaway but still central

18. Tropical Gem! Watch Jets Fly into Airport+Ocean Beach+Garden Views+MANY PERKS!!!

Tropical Gem! Watch Jets Fly into Airport+Ocean Beach+Garden Views+MANY PERKS!!!
Maho Bay
10.0 out of 10, Exceptional, (90 reviews)
"Great location!!"
United States
Jill W.
The price is CA $183
CA $331 total
includes taxes & fees
Oct 17 - Oct 18
Tropical Gem! Watch Jets Fly into Airport+Ocean Beach+Garden Views+MANY PERKS!!!

19. Philips Scott House Calinago

Philips Scott House Calinago
3.0 star property
Downtown Philipsburg
2.0 out of 10, (1 review)
The price is CA $193
CA $308 total
includes taxes & fees
Nov 16 - Nov 17
Philips Scott House Calinago

20. Maho Beach House Ocean Front Garden Studio

Maho Beach House Ocean Front Garden Studio
Maho, Sint Maarten
9.4 out of 10, Exceptional, (3 reviews)
Maho Beach House Ocean Front Garden Studio
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 home 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.