Title: Book the Best Caribbean Islands Hotels with Early Check-in in 2026 from CA $155 | Expedia.ca

[Caribbean Islands Travel Guide](https://expedia.ca/Caribbean-Islands.dx3000652683)[Hotels in Caribbean Islands](https://expedia.ca/Caribbean-Islands-Hotels.d3000652683.Travel-Guide-Hotels)[Vacation Rentals in Caribbean Islands](https://expedia.ca/Caribbean-Islands-Vacation-Rentals.d3000652683.Travel-Guide-VacationRentals)[Flights to Caribbean Islands](https://expedia.ca/Cheap-Flights-To-Caribbean-Islands.d3000652683.Travel-Guide-Flights)[Caribbean Islands Car Rentals](https://expedia.ca/Car-Rentals-In-Caribbean-Islands.d3000652683.Car-Rental-Guide)[Caribbean Islands Vacation Packages](https://expedia.ca/Caribbean-Islands.d3000652683.Destination-Travel-Guides)

![Panoramic view of a tropical beach paradise with a calm sea and palm trees.](https://images.trvl-media.com/place/3000652683/0f906013-1c42-421c-97bc-ef4a41f0db0e.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

# Find Hotels with Early Check-in in Caribbean Islands from CA $155

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## Check availability on Caribbean Islands Hotels with Early Check-in

Tonight

[Dec 17 - Dec 18](https://www.expedia.ca/Hotel-Search?regionId=3000652683&startDate=2025-12-17&endDate=2025-12-18&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Dec 18 - Dec 19](https://www.expedia.ca/Hotel-Search?regionId=3000652683&startDate=2025-12-18&endDate=2025-12-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=3000652683&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=3000652683&startDate=2025-12-26&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Caribbean Islands hotels with express check-in

![Premium bedding, in-room safe, desk, blackout drapes](https://images.trvl-media.com/lodging/2000000/1520000/1513800/1513765/3136c51d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/2000000/1520000/1513800/1513765/w5760h3835x0y5-cd22db78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1520000/1513800/1513765/9ed2aba1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/2000000/1520000/1513800/1513765/w5754h3840x5y0-8294f063.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hodelpa Garden Court

[](https://www.expedia.ca/Santiago-De-Los-Caballeros-Hotels-Hodelpa-Garden-Court.h1513765.Hotel-Information)

Puñal

9.4/10

Exceptional

(1008)

"I enjoy my stay there "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Emmanuel

CA $130

CA $167 total

includes taxes & fees

Jan 16 - Jan 17, 2026

[](https://www.expedia.ca/Santiago-De-Los-Caballeros-Hotels-Hodelpa-Garden-Court.h1513765.Hotel-Information)

![Premium Suite, 1 Bedroom, Non Smoking](https://images.trvl-media.com/lodging/1000000/980000/973700/973681/w541h383x36y38-2d2d03bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Point of interest](https://images.trvl-media.com/lodging/1000000/980000/973700/973681/b8382710.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hypo-allergenic bedding, down comforters, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/1000000/980000/973700/973681/a341ae31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lounge](https://images.trvl-media.com/lodging/1000000/980000/973700/973681/5b7a97d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Radisson Hotel Santo Domingo

[](https://www.expedia.ca/Santo-Domingo-Hotels-Radisson-Hotel-Santo-Domingo.h973681.Hotel-Information)

Downtown Santo Domingo

8.6/10

Excellent

(1012)

"The Breakfast was fresh and nice"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jeudienne

CA $121

CA $155 total

includes taxes & fees

Dec 20 - Dec 21

[](https://www.expedia.ca/Santo-Domingo-Hotels-Radisson-Hotel-Santo-Domingo.h973681.Hotel-Information)

![Beach nearby, white sand, beach towels](https://images.trvl-media.com/lodging/28000000/27600000/27595000/27594919/2229c460.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/28000000/27600000/27595000/27594919/8fd9628e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/28000000/27600000/27595000/27594919/ee0a8227.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/28000000/27600000/27595000/27594919/3d5ca337.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Vieques Guesthouse

[](https://www.expedia.ca/Vieques-Hotels-The-Vieques-Guesthouse.h27594919.Hotel-Information)

Esperanza

9.8/10

Exceptional

(503)

"Great stay and lovely hotel & staff!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Amanda

CA $257

CA $295 total

includes taxes & fees

Dec 19 - Dec 20

[](https://www.expedia.ca/Vieques-Hotels-The-Vieques-Guesthouse.h27594919.Hotel-Information)

![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/30000/23100/23011/040172a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![42-inch plasma TV with cable channels, TV, pay movies](https://images.trvl-media.com/lodging/1000000/30000/23100/23011/f8cb6e7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/30000/23100/23011/711cecd3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/1000000/30000/23100/23011/f3088f76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sheraton Santo Domingo Hotel

[](https://www.expedia.ca/Santo-Domingo-Hotels-Sheraton-Santo-Domingo-Hotel.h23011.Hotel-Information)

Gascue

8.8/10

Excellent

(1003)

"Quick stopover, clean rooms. Kind staff"

![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg)

Greg

CA $149

CA $190 total

includes taxes & fees

Jan 4 - Jan 5, 2026

[](https://www.expedia.ca/Santo-Domingo-Hotels-Sheraton-Santo-Domingo-Hotel.h23011.Hotel-Information)

![Property amenity](https://images.trvl-media.com/lodging/1000000/10000/1400/1395/dbced3a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Royal Suite (Ambassador) | View from room](https://images.trvl-media.com/lodging/1000000/10000/1400/1395/4c3d0169.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, open 7:30 AM to 7:30 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/10000/1400/1395/90b269a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, pillowtop beds, minibar, in-room safe](https://images.trvl-media.com/lodging/1000000/10000/1400/1395/6516bce6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### El Embajador, a Royal Hideaway Hotel

[](https://www.expedia.ca/Santo-Domingo-Hotels-El-Embajador.h1395.Hotel-Information)

Bella Vista

9.2/10

Wonderful

(1288)

"Great stay "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Nelson

CA $138

CA $176 total

includes taxes & fees

Dec 25 - Dec 26

[](https://www.expedia.ca/Santo-Domingo-Hotels-El-Embajador.h1395.Hotel-Information)

![Premium Apartment, 1 Queen Bed, Non Smoking | Private kitchenette](https://images.trvl-media.com/lodging/32000000/31760000/31752900/31752803/9ae1d1ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium Apartment, 1 Queen Bed, Non Smoking | In-room dining](https://images.trvl-media.com/lodging/32000000/31760000/31752900/31752803/e97b2698.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/32000000/31760000/31752900/31752803/792a31bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Flat-screen TV, Netflix, iPod dock, MP3 dock](https://images.trvl-media.com/lodging/32000000/31760000/31752900/31752803/547fb209.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Modern Suite - Pasavento Building

[](https://www.expedia.ca/Aguadilla-Hotels-Modern-Suite-Pasavento-Building.h31752803.Hotel-Information)

Aguadilla Pueblo

9.4/10

Exceptional

(211)

"Perfect"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Alexis

[](https://www.expedia.ca/Aguadilla-Hotels-Modern-Suite-Pasavento-Building.h31752803.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/10000000/9490000/9487600/9487555/357fb72d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/10000000/9490000/9487600/9487555/f8be78cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast, lunch, dinner served; international cuisine, pool views ](https://images.trvl-media.com/lodging/10000000/9490000/9487600/9487555/66f471df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite (Queen Bed) | Terrace/patio](https://images.trvl-media.com/lodging/10000000/9490000/9487600/9487555/7bc39196.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Spring Hotel Bequia

[](https://www.expedia.ca/Bequia-Island-Hotels-Spring-Hotel-Bequia.h9487555.Hotel-Information)

Bequia Island

8.8/10

Excellent

(56)

"For a small hotel the staff, facilities and rooms have so much to offer. It’s not a mainstream hotel so the rooms are very Caribbean and traditional style but it adds so much to your experience. The chef and staff are beautiful, me and partner wanted to invite the chef back to the uk, such incredible flavours come from the kitchen. Definitely had the best sleep ever, the Bequia suite is amazing! me and my partner will be coming back yearly to visit family in Saint Vincent and agreed we can’t...

![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg)

Aisha

CA $150

CA $193 total

includes taxes & fees

Dec 18 - Dec 19

[](https://www.expedia.ca/Bequia-Island-Hotels-Spring-Hotel-Bequia.h9487555.Hotel-Information)

![Beach nearby, beach towels](https://images.trvl-media.com/lodging/17000000/16010000/16000700/16000623/a663a09d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/17000000/16010000/16000700/16000623/6fe1a1e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Single Room, Balcony, Park View](https://images.trvl-media.com/lodging/17000000/16010000/16000700/16000623/f8085367.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/17000000/16010000/16000700/16000623/e3a33bde.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### RINCON PLAZA HOTEL

[](https://www.expedia.ca/Rincon-Hotels-Que-Chevere.h16000623.Hotel-Information)

Rincon

8.8/10

Excellent

(624)

"Great place to stay. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Angel

CA $166

CA $193 total

includes taxes & fees

Dec 19 - Dec 20

[](https://www.expedia.ca/Rincon-Hotels-Que-Chevere.h16000623.Hotel-Information)

![View from room](https://images.trvl-media.com/lodging/1000000/190000/186000/185936/fc0e384d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Apartment, 1 Bedroom, Ocean View](https://images.trvl-media.com/lodging/1000000/190000/186000/185936/b32bb410.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior entrance](https://images.trvl-media.com/lodging/1000000/190000/186000/185936/e0539d8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/1000000/190000/186000/185936/aa1903b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Gem Holiday Beach Resort

[](https://www.expedia.ca/St-Georges-Hotels-Gem-Holiday-Beach-Resort.h185936.Hotel-Information)

St. George's

8.2/10

Very good

(357)

"Clean , spacious room. Comfortable beds with good ac in the bedroom and a nice little patio area to sit outside. They also provided beach towels which was handy. Some tea and coffee in the room would have been nice but the kitchen was well stocked otherwise. The staff were mostly very welcoming and friendly."

![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg)

Marsha

CA $189

CA $229 total

includes taxes & fees

Jan 16 - Jan 17, 2026

[](https://www.expedia.ca/St-Georges-Hotels-Gem-Holiday-Beach-Resort.h185936.Hotel-Information)

![Garden](https://images.trvl-media.com/lodging/32000000/31850000/31840400/31840320/5adb2004.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium Apartment, 1 King Bed, Non Smoking, Garden View](https://images.trvl-media.com/lodging/32000000/31850000/31840400/31840320/1dbf6c4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium Apartment, 1 King Bed, Non Smoking, Garden View | Private kitchen](https://images.trvl-media.com/lodging/32000000/31850000/31840400/31840320/07f99178.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Point of interest](https://images.trvl-media.com/lodging/32000000/31850000/31840400/31840320/2c81d9cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Millsborough B&B

[](https://www.expedia.ca/Kingston-Hotels-MillsborougH-BnB.h31840320.Hotel-Information)

Jack's Hill

10/10

Exceptional

(16)

"Suzanne was very pleasant. The place was very clean and cozy. "

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Clifton

[](https://www.expedia.ca/Kingston-Hotels-MillsborougH-BnB.h31840320.Hotel-Information)

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.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2025-12-31&endDate=2026-01-01&regionId=3000652683&adults=2&property_amenities_group_explore=express_checkin&sort=RECOMMENDED&openPlayBack=true)

## Top Caribbean Islands Hotel Reviews

![Hotel Riu Montego Bay - Adults Only - All Inclusive](https://images.trvl-media.com/lodging/3000000/2070000/2062100/2062016/5bbbc6e7_y.jpg)

### Hotel Riu Montego Bay - Adults Only - All Inclusive

10/10 Excellent

"Everything was perfectly 👌"

[](https://expedia.ca/Montego-Bay-Hotels-Riu-Montego-Bay-Adults-Only-All-Inclusive.h2062016.Hotel-Information)

![The Royal at Atlantis](https://images.trvl-media.com/lodging/1000000/470000/460500/460429/b4c36dbb_y.jpg)

### The Royal at Atlantis

10/10 Excellent

"Wonderful experience and place to stay"

[](https://expedia.ca/Nassau-Hotels-The-Royal-At-Atlantis.h460429.Hotel-Information)

![The Condado Plaza Hotel](https://images.trvl-media.com/lodging/1000000/10000/7200/7143/e18049f2_y.jpg)

### The Condado Plaza Hotel

10/10 Excellent

"Room overlooked the ocean pool was amazing "

[](https://expedia.ca/San-Juan-Hotels-The-Condado-Plaza-Hilton.h7143.Hotel-Information)