CHESAPEAKE BEACH RESORT

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Key details

About the Hotel

83409 Overseas Highway, Islamorada, Florida, United States, 33036

Near Whale Harbor Marina

Great

8.6

9.1

/10

3.2

4.2

Loved by guests

Spacious rooms
Ocean views
Friendly staff
Clean beach

"Upgraded to a villa! Beautiful spot to watch sunrise."

Mason from United States

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"The resort provides kayaks, SUP, and fishing gear for any interested guest."

Becki W from United States

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"ROOMS Clean, staff nice, and SO close to a wide private beach.VERY NICE"

Duane

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Featuring a heated pool, the oceanfront Chesapeake Beach Resort Islamorada is 4.5 km from the Rain Barrel Village. This Islamorada resort offers 45 rooms with views of the beach.

Location

The 3-star smoke-free hotel enjoys proximity to Wilson Key, located approximately 5 minutes' walk away. The traditional property also lies in close proximity to the Whale Harbor Marina.

This hotel is 3.6 km from the Hurricane Monument.

Rooms

The rooms feature an iron and an air conditioner, along with a flat-screen TV with satellite channels for guests' utmost comfort. Bathrooms inlude a walk-in shower, a lowered sink, and a raised toilet, and such fine comforts as a hair dryer and bath sheets.

Eat & Drink

Jaws Raw Bar serves a good range of American food and lies not far from the Chesapeake.

Leisure & Business

A tennis court and a play area are available for an additional charge. This accommodation has an own beach area with free Wi-Fi access, sun loungers, and beach towels. Guests can enjoy a diving club at Chesapeake Beach Resort, which is located on a private beach.

“This Islamorada resort strikes a pleasing balance, especially for families. The private beach and complimentary water sports add real value. It's a solid choice for those seeking a relaxed oceanfront experience, with spacious villas catering particularly well to longer stays.”

James DavidEditor-in-Chief at Dogfriendly-hotels

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Highlights from guests

Sports & FitnessWater Fun

The resort has free kayaks and paddle boards. Great beach area for swimming and snorkeling. Pools are nice, plus a spa tub.

Kevin Olsen from Canada

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Guest ParkingEasy Parking

Plenty of open parking spots right next to the rooms. Free and plentiful parking which made access very easy.

Jane Miller from United States

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DiningDelicious Breakfast

Breakfast offered omelettes and pancakes made to order. The breakfast room has outdoor seating with ocean views.

David Smith from Australia

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Room FeaturesModern Comfort

Rooms are modern and clean with comfortable beds. Balconies offer great views. Mini fridge and microwave are included.

Maria Lopez from Spain

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Select your room type

The hotel provides many room choices—family rooms, doubles, and pet-friendly suites—with breakfast, free cancellation, and special offers

Ocean View King

2 persons

32 m²

1 King-size bed

Shower

Coffee machine

room details

Deluxe King Suite

2 persons

55 m²

1 King-size bed

Shower

Coffee machine

room details

Standard Queen Room

2 persons

29 m²

2 King Size Beds

Shower

Coffee machine

room details

Hearing impaired Ocean view Two Queen Beds

2 persons

34 m²

2 King Size Beds

Shower

Coffee machine

room details

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Rates & availability calendar

See current prices and availability for your chosen dates!

Facilities

Hotels feature amenities designed to keep both you and your pet comfortable

General

No smoking on site
Free Wi-Fi
Parking
24-hour reception
VIP check-in/ -out
Pets allowed
Rooms/ Facilities for disabled
Wheelchair access
Security
Luggage storage
Private beach
Allergy-free rooms
Lift
Smoke detectors
Fire extinguishers
Key card access

Sports & Fitness

Yoga class
Fishing

Guest Parking

Cookware/ Kitchen utensils

Services

Housekeeping
Shops/Commercial services
Welcome drink

Dining

Snack bar

Children

Board games

Facilities for people with disabilities

Toilet for disabled
Bathroom for disabled

Spa & Leisure

Heated swimming pool
Outdoor swimming pool
Beach access
Sun loungers
Live entertainment
Pool with view
Shallow end

Room features

Air conditioning
Heating
Sitting area
Patio
Garden furniture
Dining table

Bathroom

Free toiletries
Sink

Self-catering

Cookware/ Kitchen utensils

Media

Flat-screen TV
AM/FM alarm clock

Hotel location

83409 Overseas Highway, Islamorada, Florida, United States, 33036

Map view

83409 Overseas Highway, Islamorada, Florida, United States, 33036

City landmarks

Museum

History of Diving Museum

950 m

Landmark

Windley Key Fossil Reef Geological State Park

2.3 km

Gallery

Lobster Trap Art Gift Shop and Gallery

2.2 km

Museum

Florida Keys History and Discovery Center

2.3 km

Island

Upper Matecumbe Key

2.9 km

Island

Windley Key

2.4 km

Monument

Hurricane Monument

3.1 km

Gallery

Michelle Nicole Lowe Art Gallery

2.8 km

Landmark

Keys History & Discovery Center

2.4 km

Landmark

In the Doghouse Art Studio

3.0 km

Gallery

Pasta Pantaleo Signature Gallery

3.4 km

Gallery

Gallery Morada

3.4 km

Landmark

Carysfort Reef

3.0 km

Island

Plantation Key

3.0 km

Island

Raccoon Key

3.0 km

Church

Matecumbe United Methodist Church

3.1 km

Gallery

Elena Madden Studio Gallery

3.3 km

Gallery

Portside Studio & Gallery

3.4 km

Landmark

Cheeca Rocks

3.6 km

Landmark

Indian Key State Historic Site

4.1 km

Landmark

Lignumvitae Key Botanical State Park

4.1 km

Landmark

Rain Barrel Village

5.0 km

Landmark

FNX Club by Islamorada Fitness

4.4 km

Landmark

Rain Barrel Sculpture Gallery

5.0 km

Landmark

Crossland Gallery

4.6 km

Nearby

Marina

Whale Harbor Marina

210 m

Restaurants

Wahoo's Bar and Grill

190 m

83413 Overseas Hwy

Whale Harbor Seafood Buffet

210 m

83413 Overseas Hwy

The Sand Bar

210 m

83413 Overseas Hwy

Shuck N Dive

210 m

83413 Overseas Hwy

Casa Mar Seafood

560 m

97001 Oversea Hwy Islamorada

Ziggie & Mad Dog's

910 m

83000 Overseas Hwy

Explore Islamorada

Explore the Area

History of Diving Museum

12 minutes walking

Museum showcasing the history of diving with artifacts and exhibits. Special exhibits and guided tours available.

Windley Key Fossil Reef Geological State Park

4 minutes driving

Unique fossil reef park featuring hiking trails and geological displays. Great for nature lovers and history buffs.

Florida Keys History and Discovery Center

5 minutes driving

Center offering insights into the rich history and ecology of the Florida Keys with engaging exhibits and artifacts.

Snorkeling at Carysfort Reef

5 minutes driving

Exciting snorkeling opportunities at Carysfort Reef, ideal for thrill-seekers. Rentals and guided tours available.

Yoga on the Beach

3 minutes walking

Relaxing beach yoga sessions offered nearby, perfect for rejuvenation and connecting with nature. Classes available daily.

Wahoo's Bar and Grill

3 minutes walking

Casual spot known for fresh seafood and vibrant atmosphere. Try their famous fish tacos and outdoor seating.

Whale Harbor Seafood Buffet

3 minutes walking

Buffet offering a variety of seafood dishes in a family-friendly environment. A local favorite for seafood lovers.

Islander Watersports

3 minutes walking

Recreation area with live music and themed events. Family-friendly, featuring activities for all ages throughout the week.

Morada Way Arts & Cultural District

5 minutes driving

Local art and culture hub with galleries and occasional live performances. Experience local art events and exhibitions.

Local transport and travel tips

City Centre

Islamorada24 min · 2.0 km

Bus

Bus stop8 min · 5.3 km

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Property information and rules

Check-in

from 16:00-23:00

Check-out

from 07:00-11:00

Guest Parking

Private parking is possible on site for free.

Internet

is available in for free.

Breakfast

A full breakfast is served at the price of US$0.10 per person per day.

Children & extra beds

There are no extra beds provided in a room. There are no cots provided in a room.

Pets

Pets are allowed on request.

Year renovated:

2008

Number of rooms:

FAQs

About Chesapeake Beach Resort

What is the distance between Chesapeake Beach Resort and the nearest attractions?

Chesapeake Beach Resort is located 0.5 km from Whale Harbor Marina and 1 km from the History of Diving Museum.

What amenities are available at Chesapeake Beach Resort?

The resort features an outdoor swimming pool, a private beach, free Wi-Fi, and air conditioning in all rooms.

What types of dining options are provided at Chesapeake Beach Resort?

While there are no on-site restaurants, guests can enjoy nearby dining options such as Wahoo's Bar and Grill, Shuck N Dive, and Whale Harbor Seafood Buffet, all within 0.5 km.

What are the check-in and check-out times at Chesapeake Beach Resort?

Check-in is at 16:00 and check-out is at 11:00.

Is parking available at Chesapeake Beach Resort?

Chesapeake Beach Resort offers free private parking on-site, with prior reservation required.

What room amenities can guests expect at Chesapeake Beach Resort?

Rooms come equipped with free Wi-Fi, a 37-inch flat-screen TV, a small refrigerator, and air conditioning.

Does Chesapeake Beach Resort offer any recreational activities?

Guests can enjoy access to the private beach, fishing, and complimentary water sports equipment rentals.

Which attractions are located near Chesapeake Beach Resort?

Popular nearby attractions include the Theater of the Sea, located 4 minutes by car, and the Windley Key Fossil Reef Geological State Park, which is about 3 km away.

What additional services does Chesapeake Beach Resort provide?

The resort offers a 24-hour reception, luggage storage, and a fitness club on-site.

Are there any family-friendly amenities at Chesapeake Beach Resort?

Chesapeake Beach Resort features board games and offers a children's playground.

What features does the pool at Chesapeake Beach Resort have?

The pool is heated, open year-round, and provides ocean views along with sun loungers.