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Quiet oceanfront resort in Florida Keys

Roomy Upper Keys hotel

Wide open to sunshine and Atlantic Ocean views, this hotel by the sea in Islamorada features lots of room for tranquil sunbathing. The resort is spread across six and a half acres.

Pools and picnic tables

Grills and picnic tables are on site, and one of two pools has an adjacent spa and a view of the ocean; a small harbor offers snorkeling and fishing trips.

Balconies with views

Guestrooms in pink buildings feature balconies facing the pool area, garden, or waterfront. Rooms also have 37-inch HDTVs, clock radios with CD players and MP3 players, and wireless Internet access.

Chesapeake Beach Resort

At your hotel

Chesapeake Beach Resort has a tennis court and children's play area. The hotel hosts weddings outdoors in its tropical gardens among flowering foliage, winding pathways, and waterfalls. Other amenities include two heated swimming pools and wireless Internet access in public areas.

  • On private beach
  • Front desk (limited hours)
  • Total number of rooms - 65
  • Laundry facilities
  • Library
  • Barbecue grill(s)
  • Picnic area
  • Full-service spa
  • Number of floors - 2
  • Spa treatment room(s)
  • Multilingual staff
  • Garden
  • Free self parking
  • Pool sun loungers
  • Beach towels
  • Smoke-free property
  • Number of buildings/towers - 15
  • Coffee/tea in lobby
  • Complimentary newspapers in lobby
  • Fitness facilities
  • Free Wi-Fi
  • Computer station
  • Marina on site
  • Room service (limited hours)
  • Tennis on site
  • Outdoor tennis court
  • Spa tub
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Stay connected

Available in all rooms: Free Wi-Fi

Available in some public areas: Free Wi-Fi

Park your car

Free self parking

In your room

  • Balcony
  • Ceiling fan
  • Air conditioning
  • Climate control
  • Phone
  • Refrigerator
  • Coffee/tea maker
  • Daily housekeeping
  • Private bathroom
  • Complimentary toiletries
  • Hair dryer
  • Iron/ironing board
  • In-room safe
  • Desk
  • HDTV
  • Rollaway/extra beds available
  • Cribs/infant beds available
  • Free Wi-Fi
  • Satellite TV service
  • Flat-panel TV
  • Pillowtop mattress
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Eat and drink

All guests at Chesapeake Beach Resort have the option of a complimentary Continental breakfast served every morning on the beach.

The hotel does not have its own restaurant, but there are several dining options within the surrounding area.There are three resturants located next door at our sister property.Nearby restaurants: Islamorada Fish Co., Lorelei Restaurant, Morada Bay, Lazy Days

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A water sports center on the beach has for your enjoyment, bicycles, fishing gear, pedal boats, small catamarans and kayaks. There are limited boat slips in the marina located at the property. Please call the resort to check availability, using the information in the confirmation received after booking. Deep-sea and flats-fishing charter boats are available, as well as snorkeling excursions. The recreational activities listed below are available at or near the hotel; fees may apply.

  • Snorkeling nearby
  • Scuba diving nearby
  • Parasailing nearby
  • Complimentary bicycles on site
  • Ecotours nearby
  • Bicycle rentals on site
  • Fishing on site
  • Kayaking on site
  • Playground on site
  • Rowing or canoeing on site
  • Sailing on site
  • Tennis on site
  • Boat tours nearby
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  • Hot stone massage
  • Deep tissue massage
  • Prenatal massage
  • Couples treatment rooms
  • Manicures and pedicures
  • Body wraps
  • Body scrubs
  • Aromatherapy treatments
  • Hydrotherapy treatments
  • Massages
  • Body treatments
  • Facial treatments


To make requests for specific accessibility needs, complete the “Special or Accessibility Requests" section of “Trip Preferences" when you book your hotel.

  • Accessible bathroom
  • Accessible parking

The fine print for Chesapeake Beach Resort

When you arrive

Check-in time ends at 11 PM

Check-in time starts at 3 PM

Minimum check-in age is 21

Special check-in instructions:

The front desk will be closed daily from 11 PM - 7 AM.

When you leave

Check-out time is 11 AM

How you can pay

Accepted at this hotel: American Express, Discover, MasterCard, Visa

You need to know

Extra-person charges may apply and vary depending on hotel policy.

Government-issued photo identification and a credit card are required at check-in for incidental charges.

Special requests are subject to availability upon check-in and may incur additional charges. Special requests cannot be guaranteed.

  • Minimum Spring Break check-in age is 21 years old.

Minimum guest age is 21

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We should mention

A resort fee is included in the total price displayed. Children 12 years old and younger stay free when occupying the parent or guardian's room, using existing bedding.

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