Three Waters Resort and Marina
Best for families, groups and boaters who want many on-site activities, a full-service marina, and multiple dining options.
Hotel comparison guide
Three Waters Resort and Marina vs Chesapeake Beach Resort
Three Waters Resort and Marina is a large, marina-forward Islamorada resort with multiple pools, restaurants, and a 72-slip marina—good for families, groups, and boaters. Chesapeake Beach Resort is an established, smaller beachfront Islamorada hotel with strong guest ratings—read this if you want a classic beach stay close to local sights.
Updated
Chesapeake Beach Resort
Best for travelers who want a straightforward beachfront stay with a long-running local presence and high guest scores.
Quick Verdict: Three Waters Resort and Marina vs Chesapeake Beach Resort
Three Waters Resort and Marina wins when you want lots of on-site choices—multiple pools (including an adults-only Cove), a full-service 72-slip marina, many restaurants and bars, and family- and group-friendly programming.
Chesapeake Beach Resort wins when you want a more compact, classic beachfront hotel with a long local presence and very high guest ratings for a straightforward beach-focused stay.
Bottom line: pick Three Waters for scale, dining variety, marina access and more activities; pick Chesapeake Beach Resort for a simpler, well-reviewed beachfront hotel experience.
Three Waters Resort and Marina vs Chesapeake Beach Resort – At a Glance
| Category | Three Waters Resort and Marina | Chesapeake Beach Resort |
|---|---|---|
| Overall vibe | Resort-within-a-resort scale: social, many dining venues, active marina and event spaces | Classic beachfront hotel—smaller and simpler |
| Location (town) | Islamorada (mile marker 84) on Overseas Hwy | |
| Size / rooms | 214 rooms, suites, cottages across resort and The Cove | 60 air-conditioned rooms |
| Audience / ages | All ages overall; The Cove is adults-only (21+) enclave | All ages (not adults-only) |
| Pools/beaches | Three year-round pools (including adults-only Cove pool) and multiple beaches across the property | Private beach plus 2 outdoor pools |
| Marina & boating | Full-service marina with 72 slips and fishing/ferry options | Marina on site; boat tours and personal motor watercraft nearby |
| Restaurants & bars | Nine+ on-site outlets including Kindler Wood-Fired Fare, rooftop Little Limón, Tiki Bar, Kokomo swim-up bar and a coffee shop | One bar/lounge on site; complimentary continental breakfast; more limited dining on property |
| Spa & wellness | Oceanside massages and open-air fitness facilities (including Wave Motion Studio at The Cove) | Not published |
| Known for | Marina access, extensive dining, water taxi to sister properties, event/wedding venues | Established Islamorada beachfront property with strong guest ratings |
| Guest rating & stars | Part of Tribute Portfolio; rating not published here | 3.5 stars · guest rating 9.4/10 (supplier listing) |
A Look Inside Three Waters Resort and Marina
See all photos →
Location: Three Waters Resort and Marina vs Chesapeake Beach Resort
Three Waters Resort and Marina – Location
Three Waters sits at mile marker 84 on the Overseas Highway on 15 waterfront acres where the Atlantic, Florida Bay and Gulf meet.
- Close to Windley Key Fossil Reef Geological State Park and Theater of the Sea (walkable to some nearby sights).
- On-site marina and water taxi service to sister properties in the Islamorada Resort Collection.
- Shuttle service within the local area and self-parking included in the resort fee.
Choose Three Waters if you want a larger waterfront resort hub with easy boat access and local shuttles.
Chesapeake Beach Resort – Location
Chesapeake Beach Resort sits on Overseas Highway in Matecumbe, Islamorada, with direct private beach access.
- Located close to the History of Diving Museum and Windley Key Fossil Reef Geological State Park.
- Private beach on site plus two outdoor pools and beach loungers and towels.
- Complimentary continental breakfast and multilingual 24-hour front desk.
Choose Chesapeake Beach Resort if you prefer a straightforward beachfront hotel within easy reach of local museums and parks.
Rooms: variety and layout
Three Waters Resort and Marina – Rooms
Three Waters offers 214 rooms, suites and cottages across many room types including The Cove (21+) options.
- Room types include suites with balconies and several Cove (21) adult-only categories.
- Options for families and groups with multi-bedroom suites and sofa beds.
- Free Wi‑Fi included; enhanced Wi‑Fi and other perks included in nightly resort fee.
Three Waters gives more room-type variety and specific adult-only room choices inside The Cove.
Chesapeake Beach Resort – Rooms
Chesapeake Beach Resort has 60 air-conditioned rooms with a range of ocean-view and villa-style configurations.
- Room types listed include Ocean View Queens, Ocean View King Suite, Standard King and multiple villa-style one- and two-bedroom options.
- Rooms come with microwaves and flat-screen TVs; pillowtop beds noted in supplier listing.
- Accessible room options are available (ADA and hearing-impaired room types listed).
Chesapeake Beach Resort is smaller but includes several ocean-view and accessible room types suited to couples and families.
Dining & drinks: more options vs simpler on-site offerings
Three Waters Resort and Marina – Dining & drinks
Three Waters features a wide dining roster across casual and elevated choices on property.
- Signature restaurant Kindler Wood-Fired Fare plus rooftop Little Limón and Mercado Morada waterfront venue.
- Casual options include Islamorada Pizza Co., Lucky Twist soft-serve, Kokomo swim-up bar and a Starbucks.
- Multiple happy-hour offerings and many venues open to non-guests (reservations recommended for Kindler).
If in-resort dining variety or waterfront nightlife matters, Three Waters provides significantly more choices.
Chesapeake Beach Resort – Dining & drinks
Chesapeake Beach Resort offers a simpler on-site food-and-drink setup with a bar/lounge and complimentary continental breakfast.
- Bar/lounge on site for evening drinks.
- Complimentary continental breakfast served daily from 6:00 AM to 10:00 AM.
- Nearby restaurants are a short drive away along Overseas Highway.
Chesapeake is a good pick if you want a quieter stay and don’t need many on-site dining options.
Pools, beach and signature amenity
Three Waters Resort and Marina – Pools, beach and signature amenity
Three Waters offers three year-round pools, multiple beaches and a sizable marina as its signature amenities.
- Three pools include Kokomo (swim-up bar), Overseas Pool, and The Cove adult-only pool.
- Five beaches across the Islamorada Resort Collection properties; The Cove has its own private walk-in beach.
- Full-service marina with 72 slips and fishing charters available.
Three Waters is the choice for guests who want varied pool options plus marina access and many beaches to explore.
Chesapeake Beach Resort – Pools, beach and signature amenity
Chesapeake Beach Resort features a private beach area and two outdoor pools for guests.
- Private beach access with beach sun loungers and towels provided.
- Two outdoor pools and pool sun loungers listed in the supplier facts.
- On-site options for fishing, kayaking and boat tours nearby.
Chesapeake focuses on a straightforward beach-and-pool stay rather than a wide array of aquatic venues.
Wellness, nightlife and extras
Three Waters Resort and Marina – Wellness, nightlife and extras
Three Waters mixes wellness and nightlife across the resort, from oceanside massages to live-music venues.
- Oceanside massages (Ooh La La / Oo La La) and open-air fitness facilities including a 21+ Wave Motion Studio.
- Live music at the Tiki Bar and events at Mercado Morada and other venues.
- Daily resort fee includes activity rentals, water taxi, shuttle and a welcome cocktail.
Three Waters blends wellness and a lively evening scene, suitable for active travelers and those wanting on-site entertainment.
Chesapeake Beach Resort – Wellness, nightlife and extras
Chesapeake Beach Resort provides basic hotel services, local proximity to attractions and a calm beachfront setting.
- 24-hour front desk, concierge services and computer station listed in supplier details.
- Boat tours and personal motor watercraft available nearby; fishing and snorkeling options close by.
- Construction at a neighboring building is noted in supplier policies (possible noise during stays).
Chesapeake is for travelers who want a quieter, service-focused beachfront base rather than an activity-packed resort.
Who Wins? Best Pick by Travel Style
Three Waters Resort and Marina
Three Waters — three pools, kids’ activities, arcade and broad family programming across the resort.
Three Waters Resort and Marina
Three Waters — full-service 72-slip marina with transient slips and fishing-charter access.
Chesapeake Beach Resort
Chesapeake Beach Resort — smaller beachfront hotel with private beach access and high guest ratings.
Chesapeake Beach Resort
Chesapeake Beach Resort — 60 rooms, simple on-site amenities and a long-running local presence.
Frequently asked questions
See all FAQs →Three Waters Resort and Marina vs Chesapeake Beach Resort: FAQs
Which hotel is better for families with kids?
Three Waters—it’s set up for families with multiple pools, kids’ activities, an arcade and family-oriented dining options; The Cove is the only 21+ area.
Which is closer to local Islamorada attractions?
Both are located on Overseas Highway in Islamorada near local sights; Chesapeake’s supplier listing highlights proximity to the History of Diving Museum and Windley Key Fossil Reef.
Which hotel is better if I’m bringing a boat?
Three Waters—its full-service marina with 72 slips (including transient slips) and the deepest Upper Keys channel is built for boaters and fishing charters.
Are either property’s rooms wheelchair accessible?
Yes. Chesapeake lists ADA and hearing-impaired room types in its supplier listing; Three Waters also offers accessible rooms and a wheelchair-accessible fitness center per its info.
More Three Waters Resort and Marina Comparison Guides
Explore how Three Waters Resort and Marina stacks up against other hotels nearby:
- Three Waters Resort and Marina vs Cheeca Lodge & Spa
- Three Waters Resort and Marina vs Hawks Cay Resort
- Three Waters Resort and Marina vs Playa Largo Resort & Spa, Autograph Collection
- Three Waters Resort and Marina vs Baker's Cay Resort Key Largo, Curio Collection
- Three Waters Resort and Marina vs Islander Resort
- Three Waters Resort and Marina vs La Siesta Resort & Villas
- Three Waters Resort and Marina vs Amara Cay Resort
- Three Waters Resort and Marina vs Lime Tree Bay Resort
- Three Waters Resort and Marina vs Ocean Pointe Suites at Key Largo
- Three Waters Resort and Marina vs Waterside Suites & Marina
- Three Waters Resort and Marina vs Hadley Resort and Marina
- Three Waters Resort and Marina vs Fisher Inn Resort & Marina
- Three Waters Resort and Marina vs Hampton Inn Key Largo
- Three Waters Resort and Marina vs Holiday Inn Key Largo
- Three Waters Resort and Marina vs Largo Resort
- Three Waters Resort and Marina vs Bayside Inn Key Largo
- Three Waters Resort and Marina vs Drop Anchor
- Three Waters Resort and Marina vs Coconut Cove Resort and Marina
- All Three Waters Resort and Marina comparisons
Book your stay
Daily Rum Runner Water Taxi Included
- Lowest rate guarantee
- Complimentary perks & upgrades
- 24/7 concierge