
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 The Gap offers world-class resort destinations for every travel style, season, and budget.
Guests
- Hotels
- Villas
- Cabins
- Rentals
- Cottages
- Resorts
- Accommodations
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- Chicago
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- Near South Side
- 0.41 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
- Chicago
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- Near South Side
- 0.08 mi to center
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Parking
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Parking
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Hot Tub
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Parking
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Kitchen
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Air Conditioner
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Hot Tub
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Parking
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Kitchen
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Air Conditioner
- Chicago
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- South Loop
- 0.54 mi to center
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Parking
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Parking
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Balcony/Terrace
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Kitchen
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Air Conditioner
- Chicago
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- Printers Row
- 0.15 mi to center
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Parking
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Parking
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Balcony/Terrace
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Kitchen
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Air Conditioner
- Chicago
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- South Loop
- 0.47 mi to center
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Parking
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Parking
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Balcony/Terrace
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Kitchen
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Air Conditioner
- Chicago
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- Bronzeville
- 0.35 mi to center
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Parking
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Parking
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Balcony/Terrace
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Kitchen
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Air Conditioner
- Chicago
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- Bronzeville
- 0.39 mi to center
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Parking
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Balcony/Terrace
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View
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Kitchen
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Parking
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Balcony/Terrace
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View
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Kitchen
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Parking
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Kitchen
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Air Conditioner
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Internet
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Parking
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Kitchen
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Air Conditioner
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Internet
- Chicago
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- Grand Boulevard
- 0.46 mi to center
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Parking
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Air Conditioner
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Internet
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Pet Friendly
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Parking
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Air Conditioner
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Internet
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Pet Friendly
- Chicago
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- Bronzeville
- 0.42 mi to center
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Parking
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Ocean View
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Balcony/Terrace
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View
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Parking
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Ocean View
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Balcony/Terrace
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View
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Parking
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Parking
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Balcony/Terrace
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Kitchen
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Air Conditioner
- Chicago
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- South Loop
- 0.49 mi to center
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Internet
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Internet
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Internet
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Balcony/Terrace
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Kitchen
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Air Conditioner
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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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Air Conditioner
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Parking
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Parking
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Kitchen
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Air Conditioner
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Internet
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Parking
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Kitchen
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Air Conditioner
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Internet
- Chicago
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- Grand Boulevard
- 0.46 mi to center
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Parking
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Air Conditioner
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Internet
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Pet Friendly
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Parking
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Air Conditioner
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Internet
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Pet Friendly
- Chicago
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- Bronzeville
- 0.42 mi to center
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Parking
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Ocean View
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Balcony/Terrace
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View
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Parking
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Ocean View
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Balcony/Terrace
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View
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Parking
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Parking
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Balcony/Terrace
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Kitchen
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Air Conditioner
- Chicago
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- South Loop
- 0.49 mi to center
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Internet
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Internet
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Internet
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Internet
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Parking
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- Chicago
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- Bridgeport
- 0.78 mi to center
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Kitchen
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Air Conditioner
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Child Friendly
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TV
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Kitchen
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Air Conditioner
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Child Friendly
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TV
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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
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Parking
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Kitchen
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Air Conditioner
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Internet
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Parking
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Kitchen
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Air Conditioner
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Internet
- Chicago
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- Grand Boulevard
- 0.46 mi to center
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Parking
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Air Conditioner
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Internet
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Pet Friendly
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Parking
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Air Conditioner
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Internet
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Pet Friendly
- Chicago
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- Bronzeville
- 0.42 mi to center
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Parking
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Ocean View
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Balcony/Terrace
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View
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Parking
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Ocean View
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Balcony/Terrace
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View
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Parking
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Parking
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Balcony/Terrace
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Kitchen
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Air Conditioner
- Chicago
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- South Loop
- 0.49 mi to center
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Internet
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Internet
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Internet
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Balcony/Terrace
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Kitchen
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Air Conditioner
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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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Find the Perfect Resort Vacation in the The Gap
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 The Gap
What are the Top Resort Locations Across the The Gap?
Discover resorts in the most sought-after travel destinations nationwide:
Robert W Roloson Houses
Robert W Roloson Houses VACATION RENTALSPilgrim Baptist Church
Pilgrim Baptist Church VACATION RENTALSDouglas
Douglas VACATION RENTALSHow to Reserve Your Resorts Vacation Accommodation?
Booking Made Simple
Resorts Vacations connects travelers with verified resort stays from trusted partners across the The Gap. 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 The Gap
What Amenities Can You Expect When Booking with Resorts Vacations?
Resorts Vacations offers carefully selected resort stays across the The Gap, 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 The Gap? 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.
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Internet
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Resorts Vacations FAQs
What are the top vacation rentals in The Gap?
There are a lot of options in The Gap. If you plan on staying in the The Gap area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in The Gap:
How many vacation rentals have private pools in The Gap?
There are 11 vacation rentals with private pools near The Gap. Top-rated homes that have access to a swimming pool include:
Which vacation homes in The Gap are best for families?
If you are looking for a family-friendly vacation home in The Gap, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in The Gap:
How many vacation rentals are available in The Gap?
Currently, the total number of properties listed in 2026 is over 1 in the The Gap area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in The Gap.
More Resorts Vacations to Explore
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Travel Stories and Guides For The Gap
Explore tips, destination guides, and inspiration for your next getaway.