Hollywood Casino Holiday Rentals

Compare Villas, Resorts, & Rentals 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 $329 per night
|
9.8 (102 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 Studio with Oceanview, 4th Floor
Apartment
Maho Beach House Studio with Oceanview, 4th Floor
From US $236 per night
|
10.0 (3 Reviews)
1 Bedroom 2 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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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 $688 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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OASIS Penthouse with private garden & shared pool
Apartment
OASIS Penthouse with private garden & shared pool
From US $361 per night
10.0 (1 Review)
2 Bedrooms 5 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 (4 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 $576 per night
|
8.6 (1009 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
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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 (124 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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Maho Beach House - Luxe 1-Bedroom - Ocean View
Apartment
Maho Beach House - Luxe 1-Bedroom - Ocean View
From US $217 per night
|
9.4 (13 Reviews)
1 Bedroom 3 Guests
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About Casai's Private Villas and Holiday Rentals in Hollywood Casino

Discover more than 1665 vacation rentals available in Hollywood Casino. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Hollywood Casino.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Hollywood Casino, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Hollywood Casino. On average, places to stay near Hollywood Casino offer 848.44 ft², with nightly prices averaging US $475.

With Casai, finding and comparing holiday rentals in Hollywood Casino is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.

Frequently Asked Questions About Hollywood Casino?

What are the top holiday rentals in Hollywood Casino?

How many Casai.com holiday rentals are available in Hollywood Casino?

As of 2025, Casai boasts over 1665 properties listed in the Hollywood Casino area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Hollywood Casino.

Nearby Neighborhood (12)

Neighborhood Property Count
Maho Vacation Rentals in Simpson Bay 450
Pelican Key Vacation Rentals in Simpson Bay 99
Indigo Bay Vacation Rentals in Simpson Bay 62
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 1665 Hollywood Casino, SX Vacation Rentals

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