Hollywood Casino Vacation Rentals

Compare Vacation Rentals & Rent By Owner Homes in Hollywood Casino, Simpson Bay, Sint Maarten

Oasis@The Cliff: Beachfront Luxury Experience!
Condo
Oasis@The Cliff: Beachfront Luxury Experience!
From US $293 per night
10.0 (147 Reviews)
2 Bedrooms 4 Guests
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Mullet Bay Suites: Your Luxury Stay Awaits
Apartment
Mullet Bay Suites: Your Luxury Stay Awaits
From US $302 per night
|
9.8 (98 Reviews)
1 Bedroom 2 Guests
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Anchor House - Direct Oceanfront - Luxury & Modern Style
Condo
Anchor House - Direct Oceanfront - Luxury & Modern Style
From US $723 per night
10.0 (145 Reviews)
3 Bedrooms 6 Guests
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Serenity Penthouse - The Pinnacle of Luxury
Apartment
Serenity Penthouse - The Pinnacle of Luxury
From US $1,202 per night
|
10.0 (4 Reviews)
4 Bedrooms 8 Guests
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condostmaarten by the sea -Adults Only-
Apartment
condostmaarten by the sea -Adults Only-
From US $395 per night
|
9.6 (22 Reviews)
1 Bedroom 2 Guests
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Beautiful beachfront at The Villas On Great Bay
Villa
Beautiful beachfront at The Villas On Great Bay
From US $266 per night
10.0 (120 Reviews)
2 Bedrooms 6 Guests
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Boheme
Apartment
Boheme
From US $100 per night
10.0 (4 Reviews)
1 Bedroom 3 Guests
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The Horny Toad Guesthouse
Apartment
The Horny Toad Guesthouse
From US $361 per night
|
9.4 (53 Reviews)
1 Bedroom 2 Guests
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The Lady Bug
Apartment
The Lady Bug
From US $72 per night
|
10.0 (3 Reviews)
3 Bedrooms 8 Guests
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Spectacular View Ocean Front w/New Furnishings On Private Beach!
Condo
Spectacular View Ocean Front w/New Furnishings On Private Beach!
From US $266 per night
10.0 (90 Reviews)
2 Bedrooms 4 Guests
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Maho Beach House - Spacious 2 Bedroom - Ocean View
Apartment
Maho Beach House - Spacious 2 Bedroom - Ocean View
From US $352 per night
|
10.0 (2 Reviews)
2 Bedrooms 6 Guests
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Maho Beach House Studio with Oceanview, 4th Floor
Apartment
Maho Beach House Studio with Oceanview, 4th Floor
From US $236 per night
|
10.0 (2 Reviews)
1 Bedroom 2 Guests
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Blue Sanctuary
Villa
Blue Sanctuary
From US $575 per night
10.0 (2 Reviews)
3 Bedrooms 6 Guests
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LUXURIOUS BEACH FRONT UNIT - SPECTACULAR OCEAN VIEWS.
Condo
LUXURIOUS BEACH FRONT UNIT - SPECTACULAR OCEAN VIEWS.
From US $545 per night
10.0 (77 Reviews)
2 Bedrooms 4 Guests
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Peace of Mind - Las Brisas
Apartment
Peace of Mind - Las Brisas
From US $431 per night
10.0 (2 Reviews)
3 Bedrooms 6 Guests
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Skyline Luxury 5 Star Condo
Apartment
Skyline Luxury 5 Star Condo
From US $578 per night
|
10.0 (1 Review)
3 Bedrooms 6 Guests
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Top of the art penthouse on the beach - 4000 sq. ft of luxury
Apartment
Top of the art penthouse on the beach - 4000 sq. ft of luxury
From US $627 per night
10.0 (75 Reviews)
3 Bedrooms 8 Guests
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Puerta al Mar
House
Puerta al Mar
From US $805 per night
|
10.0 (1 Review)
5 Bedrooms 10 Guests
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WOW! WOW! WOW!, NEW VILLA LIBRE` STUNNING INSIDE AND OUT!
Villa
WOW! WOW! WOW!, NEW VILLA LIBRE` STUNNING INSIDE AND OUT!
From US $636 per night
10.0 (73 Reviews)
3 Bedrooms 6 Guests
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Beachfront luxury 2br condo
Apartment
Beachfront luxury 2br condo
From US $566 per night
|
10.0 (1 Review)
2 Bedrooms 8 Guests
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ALMA - DIRECT BEACH ACCESS 4 BR VILLA
Villa
ALMA - DIRECT BEACH ACCESS 4 BR VILLA
From US $1,080 per night
10.0 (58 Reviews)
4 Bedrooms 8 Guests
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Charming 3BR Villa w Private Pool in Pelican Key
Villa
Charming 3BR Villa w Private Pool in Pelican Key
From US $572 per night
10.0 (1 Review)
1 Bedroom 8 Guests
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3 Bedroom Condo in Simpson Bay
Apartment
3 Bedroom Condo in Simpson Bay
From US $320 per night
10.0 (1 Review)
3 Bedrooms 6 Guests
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Beautiful 2 bed rooms apartment at Aquamarina
Apartment
Beautiful 2 bed rooms apartment at Aquamarina
From US $230 per night
10.0 (1 Review)
2 Bedrooms 4 Guests
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Villas on Great Bay VILLA FOXIE
Villa
Villas on Great Bay VILLA FOXIE
From US $325 per night
|
9.8 (24 Reviews)
2 Bedrooms 6 Guests
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Maho Beach House - Grand Ocean Suite - 2 Bedroom
Apartment
Maho Beach House - Grand Ocean Suite - 2 Bedroom
From US $421 per night
|
9.7 (3 Reviews)
2 Bedrooms 6 Guests
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*OCEANFRONT Cosy and modern style condo*
Condo
*OCEANFRONT Cosy and modern style condo*
From US $271 per night
10.0 (52 Reviews)
2 Bedrooms 6 Guests
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Prive Loft
Apartment
Prive Loft
From US $94 per night
|
9.7 (3 Reviews)
1 Bedroom 3 Guests
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CHEZ SOCOLISA AT THE CLIFF
Condo
CHEZ SOCOLISA AT THE CLIFF
From US $376 per night
10.0 (45 Reviews)
2 Bedrooms 6 Guests
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Sea View @ La Siesta, Simpson Bay, St. Maarten, N.A.
Condo
Sea View @ La Siesta, Simpson Bay, St. Maarten, N.A.
From US $595 per night
10.0 (16 Reviews)
2 Bedrooms 4 Guests
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Very luxury Waterfront apartment at Las Brisas
Apartment
Very luxury Waterfront apartment at Las Brisas
From US $300 per night
|
9.7 (3 Reviews)
1 Bedroom 4 Guests
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Tradewinds at Simpson Bay
Condo
Tradewinds at Simpson Bay
From US $220 per night
|
9.4 (28 Reviews)
1 Bedroom 2 Guests
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Luxury 8 Bedroom Villa Kimon Fantastic Ocean View!
Villa
Luxury 8 Bedroom Villa Kimon Fantastic Ocean View!
From US $1,489 per night
10.0 (15 Reviews)
8 Bedrooms 24 Guests
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Modern 3BR Home with Own Private Pool
Apartment
Modern 3BR Home with Own Private Pool
From US $234 per night
|
9.6 (30 Reviews)
3 Bedrooms 8 Guests
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Calinago Friendly Family Sxm Home
Bed & Breakfast
Calinago Friendly Family Sxm Home
From US $120 per night
8.8 (21 Reviews)
1 Bedroom 2 Guests
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Charming 1-Bed Studio in Simpson Bay - Beacon Hill
Apartment
Charming 1-Bed Studio in Simpson Bay - Beacon Hill
From US $115 per night
|
9.6 (10 Reviews)
1 Bedroom 2 Guests
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Sonesta Ocean Point All Inclusive, Adults Only Resort
Resort
Sonesta Ocean Point All Inclusive, Adults Only Resort
From US $543 per night
|
8.6 (1005 Reviews)
1 Bedroom 2 Guests
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Reflection Y 5 Star Villa
Villa
Reflection Y 5 Star Villa
From US $424 per night
|
9.6 (9 Reviews)
3 Bedrooms 6 Guests
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"SeaBreeze" Beautiful oceanfront 2 bedroom, 2 bathroom condo.
Condo
"SeaBreeze" Beautiful oceanfront 2 bedroom, 2 bathroom condo.
From US $313 per night
10.0 (14 Reviews)
2 Bedrooms 4 Guests
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Serenity Penthouse
Apartment
Serenity Penthouse
From US $945 per night
|
9.6 (6 Reviews)
4 Bedrooms 8 Guests
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Gorgeous Beachfront Ground Floor 2 Bedroom 2 Bath Condo
Condo
Gorgeous Beachfront Ground Floor 2 Bedroom 2 Bath Condo
From US $303 per night
10.0 (14 Reviews)
2 Bedrooms 4 Guests
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THE VILLAS ON GREAT BAY, Villa LAVINIA #9
House
THE VILLAS ON GREAT BAY, Villa LAVINIA #9
From US $175 per night
|
9.5 (13 Reviews)
2 Bedrooms 6 Guests
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Luxury Oceanview 1BR on beach
Apartment
Luxury Oceanview 1BR on beach
From US $284 per night
|
9.5 (10 Reviews)
1 Bedroom 4 Guests
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MEcasaMEnavia Hidden Gems
Apartment
MEcasaMEnavia Hidden Gems
From US $107 per night
10.0 (14 Reviews)
1 Bedroom 2 Guests
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Maho Beach House - Elegant 1 Bedroom - Ocean View
Apartment
Maho Beach House - Elegant 1 Bedroom - Ocean View
From US $311 per night
|
9.5 (2 Reviews)
1 Bedroom 4 Guests
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Villa Bonjour water front villa next to Maho
Villa
Villa Bonjour water front villa next to Maho
From US $819 per night
10.0 (13 Reviews)
4 Bedrooms 8 Guests
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Oceanfront Escape At Aqua Mirage Condo!
Apartment
Oceanfront Escape At Aqua Mirage Condo!
From US $244 per night
9.5 (2 Reviews)
1 Bedroom 6 Guests
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Luxurious Porto Cupecoy
Condo
Luxurious Porto Cupecoy
From US $267 per night
10.0 (13 Reviews)
1 Bedroom 2 Guests
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Mullet Bay Suites - Your Luxury Stay Awaits
Apartment
Mullet Bay Suites - Your Luxury Stay Awaits
From US $271 per night
|
9.4 (141 Reviews)
40 Bedrooms 20 Guests
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condostmaarten by the sea -Adults Only-
Apartment
condostmaarten by the sea -Adults Only-
From US $198 per night
|
9.4 (123 Reviews)
12 Bedrooms 24 Guests
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LUXURY 6 BR. Ocean View - Villa Kimon With a Pool.
Villa
LUXURY 6 BR. Ocean View - Villa Kimon With a Pool.
From US $1,155 per night
10.0 (12 Reviews)
6 Bedrooms 20 Guests
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Reflection Z 5 Star Villa
Villa
Reflection Z 5 Star Villa
From US $700 per night
|
9.4 (8 Reviews)
3 Bedrooms 6 Guests
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About Hollywood Casino Vacation Rentals

With more than 1653 Hollywood Casino vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Rent By Owner Homes (RBOs) and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at an RBO property in Hollywood Casino.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With RentByOwner Hollywood Casino, you have the flexibility of comparing different options of various deals with a single click. Looking for an RBO with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner (RBOs), and other popular Airbnb-style properties in Hollywood Casino. Places to stay near Hollywood Casino are 849.66 ft² on average, with prices averaging US $473 a night.

RentByOwner makes it easy and safe to find and compare vacation rentals in Hollywood Casino with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Hollywood Casino Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Hollywood Casino?

How many Rentbyowner vacation rentals are available in Hollywood Casino?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 1653 in the Hollywood Casino area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Hollywood Casino. 

Nearby Neighborhood (12)

Neighborhood Property Count
Maho Vacation Rentals in Simpson Bay 441
Pelican Key Vacation Rentals in Simpson Bay 99
Indigo Bay Vacation Rentals in Simpson Bay 61
Belair Vacation Rentals in Simpson Bay 31
St. Peters Vacation Rentals in Simpson Bay 824
Cay Bay Vacation Rentals in Simpson Bay 1010
Almond Grove Vacation Rentals in Simpson Bay 1024
Madame's Estate Vacation Rentals in Simpson Bay 1054
Middle Region Vacation Rentals in Simpson Bay 828
South Reward Vacation Rentals in Simpson Bay 1082
Saunders Vacation Rentals in Simpson Bay 1185
Fort William Vacation Rentals in Simpson Bay 1015

There are 1653 Hollywood Casino, SX Vacation Rentals

Recently Booked Vacation Rentals Near Hollywood Casino