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Parking
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Balcony/Terrace
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Air Conditioner
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Internet

Discover the Best Resort Vacations
Explore the top resorts, from luxury beachfront escapes to family-friendly all-inclusive resorts and relaxing spa retreats. Whether you’re planning a weekend getaway or an extended vacation, the Middlesex County offers world-class resort destinations for every travel style, season, and budget.
Guests
- Hotels
- Villas
- Cabins
- Rentals
- Cottages
- Resorts
- Accommodations
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Private Beach
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Oceanfront
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Breakfast
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Parking
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Private Beach
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Oceanfront
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Breakfast
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Parking
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Pool
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Spa
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Balcony/Terrace
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Kitchen
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Pool
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Spa
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Balcony/Terrace
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Kitchen
- Montego Bay
- ·
- Runaway Bay
- 1.93 mi to center
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Air Conditioner
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Internet
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Child Friendly
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Laundry
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Air Conditioner
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Internet
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Child Friendly
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Laundry
- Manchester
- ·
- Mandeville
- 2.50 mi to center
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Parking
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Pool
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Balcony/Terrace
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View
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Parking
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Pool
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Balcony/Terrace
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View
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Pool
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Air Conditioner
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Internet
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Child Friendly
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Pool
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Air Conditioner
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Internet
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Child Friendly
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Private Pool
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Pool
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Balcony/Terrace
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Kitchen
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Private Pool
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Pool
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Balcony/Terrace
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Kitchen
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Hot Tub
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Parking
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Pool
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Air Conditioner
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Hot Tub
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Parking
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Pool
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Air Conditioner
- Montego Bay
- ·
- St. Ann's Bay
- 3.19 mi to center
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Private Pool
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Parking
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Pool
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Balcony/Terrace
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Private Pool
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Parking
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Pool
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Balcony/Terrace
- Montego Bay
- ·
- St. Ann's Bay
- 2.65 mi to center
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Parking
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Pool
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Balcony/Terrace
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View
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Parking
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Pool
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Balcony/Terrace
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View
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Private Pool
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Breakfast
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Parking
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Pool
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Private Pool
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Breakfast
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Parking
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Pool
- Saint Ann
- ·
- Mammee Bay Estates
- 0.18 mi to center
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Private Pool
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Hot Tub
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Parking
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Pool
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Private Pool
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Hot Tub
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Parking
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Pool
- Montego Bay
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- Port Maria
- 1.10 mi to center
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Breakfast
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Parking
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Ocean View
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Balcony/Terrace
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Breakfast
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Parking
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Ocean View
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Balcony/Terrace
- Jamaica
- ·
- Silver Sands
- 0.04 mi to center
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Oceanfront
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Parking
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Ocean View
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Balcony/Terrace
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Oceanfront
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Parking
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Ocean View
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Balcony/Terrace
- Montego Bay
- ·
- Runaway Bay
- 1.32 mi to center
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Private Pool
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Hot Tub
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Breakfast
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Parking
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Private Pool
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Hot Tub
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Breakfast
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Parking
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Private Pool
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Oceanfront
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Parking
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Pool
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Private Pool
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Oceanfront
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Parking
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Pool
- Kingston
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- Caribbean Estates
- 0.58 mi to center
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Parking
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Ocean View
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View
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Kitchen
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Parking
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Ocean View
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View
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Kitchen
- Saint Mary
- ·
- Tower Isle
- 0.88 mi to center
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Private Beach
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Hot Tub
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Parking
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Pool
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Private Beach
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Hot Tub
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Parking
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Pool
- Montego Bay
- ·
- St. Ann's Bay
- 0.07 mi to center
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Internet
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Child Friendly
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Security/Safety
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Internet
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Child Friendly
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Security/Safety
- Jamaica
- ·
- Blue Mountains National Park
- 1.31 mi to center
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Breakfast
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Parking
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Balcony/Terrace
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Kitchen
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Breakfast
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Parking
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Balcony/Terrace
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Kitchen
- Saint Mary
- ·
- Highgate
- 5.30 mi to center
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Parking
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Kitchen
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Internet
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Pet Friendly
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Parking
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Kitchen
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Internet
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Pet Friendly
- Manchester
- ·
- Mandeville
- 0.62 mi to center
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Hot Tub
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Parking
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Pool
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Balcony/Terrace
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Hot Tub
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Parking
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Pool
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Balcony/Terrace
- Montego Bay
- ·
- St. Ann's Bay
- 0.07 mi to center
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Internet
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Child Friendly
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Security/Safety
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Internet
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Child Friendly
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Security/Safety
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Oceanfront
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Ocean View
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View
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Air Conditioner
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Oceanfront
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Ocean View
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View
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Air Conditioner
- Jamaica
- ·
- Stewart Town
- 3.78 mi to center
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Private Pool
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Parking
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Pool
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Kitchen
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Private Pool
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Parking
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Pool
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Kitchen
- Saint Mary
- ·
- Tower Isle
- 1.55 mi to center
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Private Pool
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Oceanfront
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Parking
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Pool
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Private Pool
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Oceanfront
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Parking
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Pool
- Jamaica
- ·
- Mammee Bay
- 0.55 mi to center
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Parking
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Pool
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View
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Air Conditioner
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Parking
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Pool
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View
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Air Conditioner
- Saint Catherine
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- Ewarton
- 0.21 mi to center
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Parking
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Balcony/Terrace
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Kitchen
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Internet
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Parking
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Balcony/Terrace
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Kitchen
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Internet
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Oceanfront
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Parking
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Ocean View
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View
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Oceanfront
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Parking
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Ocean View
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View
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Parking
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Pool
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Balcony/Terrace
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View
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Parking
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Pool
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Balcony/Terrace
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View
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Parking
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Pool
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Balcony/Terrace
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View
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Parking
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Pool
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Balcony/Terrace
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View
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Parking
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Pool
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Balcony/Terrace
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View
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Parking
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Pool
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Balcony/Terrace
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View
- Jamaica
- ·
- Mammee Bay
- 0.15 mi to center
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Oceanfront
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Hot Tub
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Parking
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Pool
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Oceanfront
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Hot Tub
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Parking
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Pool
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Private Pool
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Parking
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Pool
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Spa
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Private Pool
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Parking
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Pool
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Spa
- Saint Mary
- ·
- Tower Isle
- 1.51 mi to center
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Private Beach
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Oceanfront
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Parking
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Pool
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Private Beach
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Oceanfront
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Parking
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Pool
- Montego Bay
- ·
- Robins Bay
- 1.15 mi to center
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Breakfast
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Parking
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Balcony/Terrace
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Kitchen
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Breakfast
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Parking
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Balcony/Terrace
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Kitchen
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Hot Tub
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Parking
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Pool
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Balcony/Terrace
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Hot Tub
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Parking
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Pool
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Balcony/Terrace
- Jamaica
- ·
- Stewart Town
- 6.99 mi to center
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Parking
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Pool
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Kitchen
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Air Conditioner
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Parking
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Pool
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Kitchen
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Air Conditioner
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Parking
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Pool
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Kitchen
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Air Conditioner
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Parking
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Pool
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Kitchen
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Air Conditioner
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Breakfast
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Parking
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Pool
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Balcony/Terrace
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Breakfast
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Parking
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Pool
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Balcony/Terrace
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Air Conditioner
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Internet
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Child Friendly
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Laundry
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Air Conditioner
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Internet
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Child Friendly
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Laundry
- Jamaica
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- Blue Mountains National Park
- 1.34 mi to center
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Breakfast
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Parking
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Pool
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Balcony/Terrace
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Breakfast
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Parking
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Pool
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Child Friendly
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Laundry
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Kitchen
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Air Conditioner
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Child Friendly
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Laundry
- Saint Mary
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- Highgate
- 4.85 mi to center
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Private Pool
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Parking
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Pool
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Balcony/Terrace
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Private Pool
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Parking
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Pool
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Balcony/Terrace
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Pool
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Internet
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Child Friendly
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TV
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Pool
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Internet
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Child Friendly
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TV
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Pool
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Pool
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Balcony/Terrace
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Kitchen
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Air Conditioner
Find the Perfect Resort Vacation in the Middlesex County
What makes our resorts stand out?
Verified Properties
Every vacation home shown on Resort Vacation comes from trusted travel sources and verified hosts, so you can browse with confidence.
Value You Can Trust
Compare a range of properties and find fair, transparent pricing—no hidden fees.
Endless Variety
From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.
Popular Resort Destinations in the Middlesex County
What are the Top Resort Locations Across the Middlesex County?
Discover resorts in the most sought-after travel destinations nationwide:
Jamaica
Jamaica VACATION RENTALSNorth Coast
North Coast VACATION RENTALSSaint Ann
Saint Ann VACATION RENTALSOcho Rios
Ocho Rios VACATION RENTALSOcho Rios
Ocho Rios VACATION RENTALSSaint Catherine
Saint Catherine VACATION RENTALSClarendon
Clarendon VACATION RENTALSThompson Town
Thompson Town VACATION RENTALSMorgans Pass
Morgans Pass VACATION RENTALSSaint Mary
Saint Mary VACATION RENTALSPortmore
Portmore VACATION RENTALSSt. Ann's Bay
St. Ann's Bay VACATION RENTALSHow to Reserve Your Resorts Vacation Accommodation?
Booking Made Simple
Resorts Vacations connects travelers with verified resort stays from trusted partners across the Middlesex County. Once you find the perfect resort, you’ll be seamlessly guided to our partner’s secure booking platform to complete your reservation with confidence.
SEARCH PROPERTIES
Use filters for location, amenities, and budget.
VIEW DETAILS
Check photos, reviews, and features for your top picks.
BOOK SECURELY
Confirm your stay safely through our trusted travel partners.
Common Resort Vacation Amenities in the Middlesex County
What Amenities Can You Expect When Booking with Resorts Vacations?
Resorts Vacations offers carefully selected resort stays across the Middlesex County, designed for comfort, convenience, and memorable experiences.
Indoor Amenities
Spacious guest rooms and suites
Spacious living areas with streaming TVs
Complimentary Wi-Fi
Air conditioning and heating
In-unit washer and dryer
Plush bedding and comfortable furniture
Outdoor Amenities
Balconies or patios with coastal views
Private or shared pools
BBQ grills and outdoor dining areas
On-site parking
Easy access to beaches and attractions
More Places to Stay with Resorts Vacations
Looking for the perfect resort vacation in the Middlesex County? Discover a curated collection of resort stays offering comfort, convenience, and unforgettable experiences in top destinations nationwide. Whether you’re searching for a beachfront resort, a family-friendly escape, or a luxury retreat, Resorts Vacations makes it easy to explore and compare verified resort options for your next getaway.
- Montego Bay
- ·
- Robins Bay
- 1.15 mi to center
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Breakfast
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Parking
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Balcony/Terrace
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Kitchen
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Breakfast
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Parking
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Balcony/Terrace
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Kitchen
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Private Pool
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Parking
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Pool
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Spa
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Private Pool
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Parking
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Pool
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Spa
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Private Beach
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Oceanfront
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Parking
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Pool
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Private Beach
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Oceanfront
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Parking
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Pool
- Montego Bay
- ·
- Oracabessa
- 1.21 mi to center
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Parking
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Pool
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Balcony/Terrace
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View
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Parking
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Pool
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Balcony/Terrace
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View
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Breakfast
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Parking
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Pool
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Spa
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Breakfast
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Parking
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Pool
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Spa
- Saint Mary
- ·
- Tower Isle
- 1.52 mi to center
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Private Beach
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Oceanfront
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Parking
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Pool
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Private Beach
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Oceanfront
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Parking
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Pool
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Hot Tub
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Breakfast
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Parking
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Pool
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Hot Tub
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Breakfast
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Parking
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Pool
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Hot Tub
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Parking
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Pool
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Balcony/Terrace
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Hot Tub
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Parking
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Pool
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Balcony/Terrace
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Hot Tub
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Breakfast
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Parking
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Pool
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Hot Tub
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Breakfast
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Parking
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Pool
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Parking
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Pool
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Balcony/Terrace
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View
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Parking
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Pool
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Balcony/Terrace
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View
- Saint Mary
- ·
- Tower Isle
- 1.32 mi to center
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Hot Tub
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Breakfast
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Parking
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Pool
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Hot Tub
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Breakfast
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Parking
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Pool
- Jamaica
- ·
- Silver Sands
- 2.38 mi to center
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Private Beach
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Oceanfront
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Hot Tub
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Parking
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Private Beach
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Oceanfront
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Hot Tub
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Parking
Resorts Vacations FAQs
What are the top vacation rentals in Middlesex County?
There are a lot of options in Middlesex County. If you plan on staying in the Middlesex County area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Middlesex County:
- Blessings at Strawberry Fields
- Pineapple Vista Resort
- Hermosa Cove Villa Resort & Suites
- WaveCrestResortRaceCourse
- Jamaica Inn
- Chrisanns Beach Resort, Apt 21
- Sandals Jamaica Royal Plantation All Inclusive Adults Only
- 1 Bedroom Penthouse Suite 63, Mystic Ridge Resort
- Couples Sans Souci All Inclusive
- 1 bedroom Penthouse Suite 63 at Mystic Ridge Resort
How many vacation rentals have private pools in Middlesex County?
There are 659 vacation rentals with private pools near Middlesex County. Top-rated homes that have access to a swimming pool include:
Which vacation homes in Middlesex County are best for families?
If you are looking for a family-friendly vacation home in Middlesex County, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Middlesex County:
How many vacation rentals are available in Middlesex County?
Currently, the total number of properties listed in 2026 is over 86 in the Middlesex County area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Middlesex County.
More Resorts Vacations to Explore
- Jamaica
- ·
- Mammee Bay
- 0.01 mi to center
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Breakfast
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Parking
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Pool
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Spa
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Breakfast
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Parking
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Pool
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Spa
- Montego Bay
- ·
- Runaway Bay
- 1.72 mi to center
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Private Beach
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Oceanfront
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Parking
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Pool
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Private Beach
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Oceanfront
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Parking
-
Pool
- Montego Bay
- ·
- Robins Bay
- 1.15 mi to center
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Breakfast
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Parking
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Balcony/Terrace
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Kitchen
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Breakfast
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Parking
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Balcony/Terrace
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Kitchen
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Parking
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Pool
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Balcony/Terrace
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View
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Parking
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Pool
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Balcony/Terrace
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View
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Oceanfront
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Parking
-
Pool
-
Ocean View
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Oceanfront
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Parking
-
Pool
-
Ocean View
- Saint Mary
- ·
- Tower Isle
- 1.51 mi to center
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Private Beach
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Oceanfront
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Parking
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Pool
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Private Beach
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Oceanfront
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Parking
-
Pool
- Montego Bay
- ·
- Oracabessa
- 1.21 mi to center
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Parking
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Pool
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Balcony/Terrace
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View
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Parking
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Pool
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Balcony/Terrace
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View
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Oceanfront
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Breakfast
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Parking
-
Pool
-
Oceanfront
-
Breakfast
-
Parking
-
Pool
- Montego Bay
- ·
- Runaway Bay
- 0.82 mi to center
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Parking
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Pool
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View
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Air Conditioner
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Parking
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Pool
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View
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Air Conditioner
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Private Beach
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Oceanfront
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Parking
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Pool
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Private Beach
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Oceanfront
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Parking
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Pool
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Oceanfront
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Parking
-
Pool
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Ocean View
-
Oceanfront
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Parking
-
Pool
-
Ocean View
- Montego Bay
- ·
- Runaway Bay
- 1.22 mi to center
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Breakfast
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Parking
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Pool
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Spa
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Breakfast
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Parking
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Pool
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Spa