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Cheeca Lodge & Spa Islamorada, Florida
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Hotel comparison guide

Cheeca Lodge & Spa vs Chesapeake Beach Resort

Cheeca Lodge & Spa is a five-star, amenity-heavy beachfront resort in Islamorada for travelers who want a full-service luxury stay with spa, golf, kids' activities and multiple dining outlets. Chesapeake Beach Resort is a long-running, classic Islamorada beachfront option with a smaller footprint and straightforward, family-friendly rooms — read this if you want a simpler, waterfront stay or are comparing value vs. resort amenities.

Updated · about 1.2 km apart

Curved resort pool lined with palm trees and lounge chairs at Cheeca Lodge & Spa

Cheeca Lodge & Spa

Luxury · Family-friendly · Activities-heavy

Best for travelers who want a full-service luxury escape with a large beach, multiple pools, a full spa and more on-site activities.

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Chesapeake Beach Resort, Islamorada, Florida

Chesapeake Beach Resort

Classic beachfront · Compact · Value-oriented

Best for travelers who want a straightforward, classic Florida Keys beachfront stay in a smaller, well-known Islamorada property.

Quick Verdict: Cheeca Lodge & Spa vs Chesapeake Beach Resort

When Cheeca Lodge & Spa wins: Choose Cheeca if you want more on-site options — multiple restaurants and bars, a full-service spa with a dedicated spa pool, a long private beach, a fishing pier, golf and organized family programming.

When Chesapeake Beach Resort wins: Choose Chesapeake Beach Resort if you prefer a smaller, simpler beachfront hotel with two outdoor pools, private beach access, complimentary continental breakfast and an established local name.

Bottom line: Cheeca is the pick for amenity-rich, resort-style stays and special-occasion travel; Chesapeake Beach Resort is a sensible, compact beachfront choice for travelers who prioritize a classic Keys location and a smaller property footprint.

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Cheeca Lodge & Spa vs Chesapeake Beach Resort – At a Glance

Side-by-side facts for Cheeca Lodge & Spa and Chesapeake Beach Resort
CategoryCheeca Lodge & SpaChesapeake Beach Resort
Overall vibeFive-star, resort with many on-site amenities and family programmingClassic Islamorada beachfront hotel with a straightforward offering
LocationAtlantic side of Islamorada, mile marker 82; private white-sand beach and 525-foot fishing pierIslamorada (Matecumbe) waterfront location on Overseas Hwy
SizeOver 240 rooms across a 27-acre property60 air-conditioned rooms
Ages / audienceAll ages; seasonal kids' club (Camp Cheeca) and family pools plus adults-only pool areasAll ages (not adults-only)
PoolsThree resort pools (two oceanfront family pools + one adults-only relaxation pool) plus a spa adults-only lap poolTwo outdoor pools
Restaurants & barsMultiple on-site restaurants and bars (Atlantic's Edge, Nikai Sushi Bar & Restaurant, Mia Cucina, Tiki Bar, 25 South, Pierre's and others)Not published
Spa & wellnessFull-service 5,700 sq ft Spa at Cheeca Lodge with six treatment rooms, fitness center and spa poolNot published
Known for1,200 feet of private white-sand beach, 525-foot fishing pier, golf course, family and event facilitiesClassic, long-running Islamorada beachfront resort name and waterfront location
Accessibility & practicalResort-wide complimentary Wi‑Fi, valet and self-parking, 24-hour shuttle service, resort fee appliesComplimentary Wi‑Fi, off-street parking, 24-hour front desk

A Look Inside Cheeca Lodge & Spa

Cheeca Lodge & Spa: rooms & suitesRooms & suitesCheeca Lodge & Spa: pools & beachPools & beachCheeca Lodge & Spa: diningDiningCheeca Lodge & Spa: spa & wellnessSpa & wellness
See all photos →

Location: Cheeca Lodge & Spa vs Chesapeake Beach Resort

Cheeca Lodge & Spa – Location

Cheeca sits on the Atlantic side of Islamorada at mile marker 82 with a long private beach and a 525-foot fishing pier.

  • 1,200 feet of private white-sand beach on property.
  • 525-foot fishing pier described as the longest in the Florida Keys.
  • Close to MoradaWay Arts & Cultural District, Florida Keys Brewing Co. and local attractions.

Cheeca offers an expansive beachfront setting with direct Atlantic access and easy local walkability around mile marker 82.

Chesapeake Beach Resort – Location

Chesapeake Beach Resort is a Matecumbe-area beachfront hotel on Overseas Highway in Islamorada.

  • Located in Islamorada (Matecumbe) with direct beach access listed as 'on private beach'.
  • Within short local distances to nearby museums and parks (History of Diving Museum, Windley Key Fossil Reef Geological State Park).
  • Supplier listing gives the address as 83409 Overseas Hwy, Islamorada, FL 33036.

Chesapeake is a straightforward beachfront location in Matecumbe with easy access to nearby Islamorada attractions.

Rooms: variety and size

Cheeca Lodge & Spa – Rooms

Cheeca has a large and varied room portfolio across guestrooms, suites, bungalows and villas.

  • Over 240 rooms listed across 21+ room types including Beach Bungalow, Premier Suites and 2-bedroom villas.
  • Room types accommodate families and groups (suites with sofa beds, multi-bed configurations).
  • Rooms include resort-wide complimentary Wi‑Fi; many room types have oceanfront or resort views.

Cheeca offers many room types for families, couples and groups seeking space and varied views.

Chesapeake Beach Resort – Rooms

Chesapeake Beach Resort offers a more compact set of room types focused on standard rooms, suites and villas.

  • Listing shows about 60 air-conditioned rooms with many named room types (Standard King, Ocean View King Suite, 2-bedroom villa, ADA options).
  • Room features commonly include microwaves, flat-screen TVs and pillowtop beds.
  • Complimentary continental breakfast is offered daily.

Chesapeake has fewer rooms and a straightforward set of room types suitable for travelers who want a simple beachfront room.

Dining & drinks: choices and style

Cheeca Lodge & Spa – Dining & drinks

Cheeca provides multiple on-site dining outlets from casual to fine-dining.

  • Atlantic's Edge (flagship seafood/steak restaurant) plus Nikai Sushi Bar & Restaurant, Mia Cucina (pizza), Tiki Bar and 25 South pool bar, among others.
  • Breakfast, lunch and dinner options; reservations recommended for signature restaurants during peak times.
  • Tiki Bar and some outlets offer live music and casual, beachside service.

Cheeca suits guests who prefer many on-site dining options and varied cuisine styles without leaving the resort.

Chesapeake Beach Resort – Dining & drinks

Chesapeake's supplier listing confirms at least one bar/lounge and complimentary continental breakfast.

  • Supplier listing notes a bar/lounge and complimentary continental breakfast served daily from 6:00 AM to 10:00 AM.
  • Rooms include microwaves for simple in-room meal options.
  • Specific on-site restaurant names and a full dining lineup are not published in the supplied listing.

Chesapeake covers basic dining needs on-site and in-room but does not publish a multi-venue dining program like Cheeca.

Pools, beach & signature amenities

Cheeca Lodge & Spa – Pools, beach & signature amenities

Cheeca centers on beach and water-based amenities, plus sports and family activities.

  • Three outdoor pools: two oceanfront family pools and one adults-only relaxation pool; plus the spa's adults-only heated lap pool.
  • 1,200 feet of private white-sand beach and a full line of watersports (kayaks, paddleboards, snorkeling lagoon, fishing pier).
  • On-site Jack Nicklaus executive 9-hole par-3 golf course and six lighted sport courts (tennis, pickleball, basketball, sand volleyball).

Cheeca is the choice for guests who want extensive beach, water and active-sport options without leaving the resort.

Chesapeake Beach Resort – Pools, beach & signature amenities

Chesapeake focuses on direct beach access and simpler pool offerings.

  • Private beach access and beach sun loungers are listed among amenities.
  • Two outdoor pools are available on property.
  • On-site marina and boat/ watercraft activity listings include boat tours and nearby personal motor watercraft.

Chesapeake provides the waterfront basics — private beach and pools — without the larger resort activity program.

Wellness & nightlife

Cheeca Lodge & Spa – Wellness & nightlife

Cheeca pairs a full spa with evening live music and multiple bars.

  • The Spa at Cheeca Lodge is a 5,700 sq ft facility with six treatment rooms, fitness center, adult lap pool and daily hours 9:00 AM–6:00 PM.
  • Evening options include live music at Atlantic's Edge and the Tiki Bar plus two poolside bars for sunset drinks.
  • Spa treatments include massages, facials, body wraps, aromatherapy and CBD therapies; spa bookings are recommended in advance at peak times.

Cheeca supports a wellness-focused stay and relaxed after-dark options on property.

Chesapeake Beach Resort – Wellness & nightlife

Chesapeake's supplied listing emphasizes basic on-site services and a bar/lounge.

  • Amenities list includes a bar/lounge and multilingual 24-hour front desk.
  • No full-service spa or spa hours are published in the supplier listing.
  • Property offers concierge services and boat tours on site.

Chesapeake covers essential evening and concierge services but does not publish a full spa program.

Who Wins? Best Pick by Travel Style

Best for spa and wellness
Spacious lobby seating area with chandeliers and bar at Cheeca Lodge & Spa

Cheeca Lodge & Spa

Cheeca — full-service 5,700 sq ft spa with treatment rooms, adults-only lap pool and scheduled classes.

Best for a compact beachfront stay
Chesapeake Beach Resort, Islamorada, Florida

Chesapeake Beach Resort

Chesapeake Beach Resort — smaller property with direct private beach access and two outdoor pools.

Best for families who want activities
Lobby lounge with sectional sofas and ocean mural behind the front desk at Cheeca Lodge & Spa

Cheeca Lodge & Spa

Cheeca — kids' club, watersports, fishing pier, golf and multiple family pools.

Best for a simpler room-and-beach budget
Chesapeake Beach Resort, Islamorada, Florida

Chesapeake Beach Resort

Chesapeake Beach Resort — straightforward rooms, free continental breakfast and fewer on-site extras.

Frequently asked questions

Cheeca Lodge & Spa vs Chesapeake Beach Resort: FAQs

See all FAQs →
Which property is better for families with kids?

Cheeca is aimed at families with a seasonal kids' club (Camp Cheeca), multiple family pools and many on-site activities; Chesapeake accepts families but offers fewer organized kids' amenities.

Do both hotels have private beaches?

Yes. Cheeca has 1,200 feet of private white-sand beach; Chesapeake Beach Resort is listed as being on a private beach.

Is there a full spa at Chesapeake Beach Resort?

Not published — the supplier listing for Chesapeake does not provide details about a full-service spa.

Which hotel is better for booking on-site dining options?

Cheeca has multiple named restaurants and bars covering casual to fine-dining; Chesapeake's listing notes a bar/lounge and complimentary continental breakfast but does not publish a multi-venue dining lineup.

More Cheeca Lodge & Spa Comparison Guides

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