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Chesapeake Beach Resort

4.3(1,165)
Hotel

About

Chesapeake Beach Resort offers bright rooms and suites with private balconies overlooking the ocean or lush gardens, creating a tranquil setting for business stays or multi-night group bookings. The recently renovated property features two outdoor pools, including a saltwater option with a hot tub, plus direct beach access for breaks between meetings.

The resort’s oceanfront event spaces provide a scenic backdrop for small corporate gatherings, with on-site food and beverage service enhancing the turnkey experience. Conveniently located near local dining and amenities, Chesapeake Beach Resort combines relaxed Florida Keys charm with professional hospitality for memorable business events.

Best for

  • Executive retreats with ocean views
  • Team offsites by the beach & pools
  • Multi-day group stays with water sports

Request a Package

Tell the venue what you're planning and they'll respond with a custom proposal within 1–2 business days.

Group Meeting

Custom request

Professional meeting space for your team — whether it's a meeting, training, workshop, or multi-day offsite. Half-day, full-day, or multi-day — with the option to request AV, catering, and your preferred room layout.

What's typically included

  • Meeting room & layout
  • Food & beverage
  • AV & technology

Room Block

Custom request

Reserve a block of rooms for your group — ideal for multi-day conferences, offsites, or any event where attendees are traveling from out of town.

What's typically included

  • Reserved guest rooms for your group
  • Flexible check-in & check-out dates
  • Negotiated group rates

Meeting + Room Block

Custom request

Bundle your meeting space and guest rooms in one request — perfect for multi-day offsites and conferences where the team meets by day and stays overnight.

What's typically included

  • Meeting room & layout
  • Food & beverage
  • AV & technology
  • Reserved guest rooms for your group

Venue Details

Standout features

Two outdoor pools with ocean views
Outdoor Amenities
Two outdoor pools with ocean views
The resort offers both a saltwater and a freshwater pool, each overlooking the ocean, plus a hot tub and direct beach access. These features create a relaxing setting for breaks or socializing during events.
Oceanfront setting in the Sport Fishing Capital of the World
Location
Oceanfront setting in the Sport Fishing Capital of the World
Situated on the beach in Islamorada, the resort provides scenic ocean views from every room balcony and immediate access to water sports rentals, making it ideal for groups seeking a distinctive seaside experience.
Made-to-order breakfast with standout omelets
Food & Beverage
Made-to-order breakfast with standout omelets
Guests consistently praise the complimentary breakfast, especially the made-to-order omelet station, which adds a personalized and high-quality touch to morning dining.

At a glance

Rated 4.3 on Google · 1,165 reviews