Entire condo

Caloosa Cove Resort by CoolVacay

Property class: 3

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Caloosa Cove Resort by CoolVacay provides amenities, such as a marina and a restaurant. Stay connected with free in-room WiFi.

Reviews

9.0 out of 10
Wonderful

Popular amenities

  • Kitchen
  • Parking included
  • Free Wi-Fi
  • Air-conditioning

Room options

Available filters for rooms
Showing 30 of 30 rooms

View all photos for Standard Studio, Balcony, Pool View

A hotel room with a bed, a sofa, a nightstand, a lamp, a framed picture, and a wicker hanging light fixture.

Standard Studio, Balcony, Pool View

  • 37 sq m
  • 1 bedroom
  • Sleeps 3
  • 1 Queen Bed and 1 Double Sofa Bed

View all photos for Standard Studio, Balcony, Ocean View

A hotel room with a bed, a sofa, a nightstand, a lamp, a framed picture, and a wicker hanging light fixture.

Standard Studio, Balcony, Ocean View

  • Ocean view
  • 37 sq m
  • 1 bedroom
  • Sleeps 3
  • 1 Queen Bed and 1 Double Sofa Bed

View all photos for Standard Studio, Balcony, Pool View

A hotel room with a bed, a sofa, a nightstand, a lamp, a framed picture, and a wicker hanging light fixture.

Standard Studio, Balcony, Pool View

  • 37 sq m
  • 1 bedroom
  • Sleeps 3
  • 1 Double Sofa Bed and 1 Queen Bed

View all photos for Deluxe Suite, 1 Bedroom, Balcony

Room

Deluxe Suite, 1 Bedroom, Balcony

  • 74 sq m
  • 1 bedroom
  • Sleeps 6
  • 2 Queen Beds and 1 Double Sofa Bed

View all photos for Standard Studio, Balcony, Ocean View

A hotel room with a bed, a sofa, a nightstand, a lamp, a framed picture, and a wicker hanging light fixture.

Standard Studio, Balcony, Ocean View

  • Ocean view
  • 37 sq m
  • 1 bedroom
  • Sleeps 3
  • 1 Double Sofa Bed and 1 Queen Bed

View all photos for Standard Studio, Balcony, Ocean View

A hotel room with a bed, a sofa, a nightstand, a lamp, a framed picture, and a wicker hanging light fixture.

Standard Studio, Balcony, Ocean View

  • Ocean view
  • 37 sq m
  • 1 bedroom
  • Sleeps 3
  • 1 Double Sofa Bed and 1 Queen Bed

View all photos for Standard Suite, 1 Bedroom, Balcony

A bedroom with a bed, a nightstand, a lamp, a ceiling fan, and a wardrobe.

Standard Suite, 1 Bedroom, Balcony

  • 74 sq m
  • 1 bedroom
  • Sleeps 6
  • 1 Queen Bed, 1 Double Sofa Bed and 1 Queen Sofa Bed

View all photos for Deluxe Suite, 1 Bedroom, Balcony, Pool View

Room

Deluxe Suite, 1 Bedroom, Balcony, Pool View

  • 74 sq m
  • 1 bedroom
  • Sleeps 6
  • 2 Queen Beds and 1 Double Sofa Bed

View all photos for Deluxe Suite, 1 Bedroom, Balcony

Room

Deluxe Suite, 1 Bedroom, Balcony

  • 74 sq m
  • 1 bedroom
  • Sleeps 6
  • 2 Queen Beds and 1 Double Sofa Bed

View all photos for Deluxe Suite, 1 Bedroom, Balcony

Room

Deluxe Suite, 1 Bedroom, Balcony

  • Marina view
  • 74 sq m
  • 1 bedroom
  • Sleeps 6
  • 2 Queen Beds and 1 Double Sofa Bed

View all photos for Standard Studio, Balcony

A hotel room with a bed, a sofa, a nightstand, a lamp, a framed picture, and a wicker hanging light fixture.

Standard Studio, Balcony

  • 37 sq m
  • 1 bedroom
  • Sleeps 3
  • 1 Double Sofa Bed and 1 Queen Bed

View all photos for Deluxe Suite, 1 Bedroom, Balcony

Room

Deluxe Suite, 1 Bedroom, Balcony

  • 74 sq m
  • 1 bedroom
  • Sleeps 6
  • 2 Queen Beds and 1 Double Sofa Bed

View all photos for Standard Suite, 1 Bedroom, Balcony

A bedroom with a bed, a nightstand, a lamp, a ceiling fan, and a wardrobe.

Standard Suite, 1 Bedroom, Balcony

  • 74 sq m
  • 1 bedroom
  • Sleeps 6
  • 1 Queen Bed, 1 Double Sofa Bed and 1 Queen Sofa Bed

View all photos for Standard Suite, 1 Bedroom, Balcony, Marina View

A bedroom with a bed, a nightstand, a lamp, a ceiling fan, and a wardrobe.

Standard Suite, 1 Bedroom, Balcony, Marina View

  • Marina view
  • 74 sq m
  • 1 bedroom
  • Sleeps 6
  • 1 Queen Bed, 1 Double Sofa Bed and 1 Queen Sofa Bed

View all photos for Deluxe Suite, 1 Bedroom, Balcony, Marina View

Room

Deluxe Suite, 1 Bedroom, Balcony, Marina View

  • Marina view
  • 74 sq m
  • 1 bedroom
  • Sleeps 6
  • 2 Queen Beds and 1 Double Sofa Bed

View all photos for Deluxe Suite, 1 Bedroom, Balcony, Pool View

Room

Deluxe Suite, 1 Bedroom, Balcony, Pool View

  • 74 sq m
  • 1 bedroom
  • Sleeps 6
  • 2 Queen Beds and 1 Double Sofa Bed

View all photos for Deluxe Suite, 1 Bedroom, Balcony, Marina View

Room

Deluxe Suite, 1 Bedroom, Balcony, Marina View

  • Marina view
  • 74 sq m
  • 1 bedroom
  • Sleeps 6
  • 2 Queen Beds and 1 Double Sofa Bed

View all photos for Standard Studio, Balcony

A hotel room with a bed, a sofa, a nightstand, a lamp, a framed picture, and a wicker hanging light fixture.

Standard Studio, Balcony

  • 37 sq m
  • 1 bedroom
  • Sleeps 3
  • 1 Double Sofa Bed and 1 Queen Bed

View all photos for Deluxe Suite, 1 Bedroom, Balcony, Ocean View

Room

Deluxe Suite, 1 Bedroom, Balcony, Ocean View

  • Ocean view
  • 74 sq m
  • 1 bedroom
  • Sleeps 6
  • 2 Queen Beds and 1 Double Sofa Bed

View all photos for Standard Studio, Balcony, Ocean View

A hotel room with a bed, a sofa, a nightstand, a lamp, a framed picture, and a wicker hanging light fixture.

Standard Studio, Balcony, Ocean View

  • Ocean view
  • 37 sq m
  • 1 bedroom
  • Sleeps 3
  • 1 Double Sofa Bed and 1 Queen Bed

View all photos for Deluxe Suite, 1 Bedroom, Balcony

Room

Deluxe Suite, 1 Bedroom, Balcony

  • Marina view
  • 74 sq m
  • 1 bedroom
  • Sleeps 6
  • 2 Queen Beds and 1 Double Sofa Bed

View all photos for Standard Suite, 1 Bedroom, Balcony, Marina View

A bedroom with a bed, a nightstand, a lamp, a ceiling fan, and a wardrobe.

Standard Suite, 1 Bedroom, Balcony, Marina View

  • Marina view
  • 74 sq m
  • 1 bedroom
  • Sleeps 6
  • 1 Queen Bed, 1 Double Sofa Bed and 1 Queen Sofa Bed

View all photos for Deluxe Suite, 1 Bedroom, Balcony, Ocean View

Room

Deluxe Suite, 1 Bedroom, Balcony, Ocean View

  • Ocean view
  • 74 sq m
  • 1 bedroom
  • Sleeps 6
  • 2 Queen Beds and 1 Double Sofa Bed

View all photos for Deluxe Suite, 1 Bedroom, Balcony, Pool View

Room

Deluxe Suite, 1 Bedroom, Balcony, Pool View

  • 74 sq m
  • 1 bedroom
  • Sleeps 6
  • 2 Queen Beds and 1 Double Sofa Bed

View all photos for Standard Studio, Balcony, Ocean View

A hotel room with a bed, a sofa, a nightstand, a lamp, a framed picture, and a wicker hanging light fixture.

Standard Studio, Balcony, Ocean View

  • Ocean view
  • 37 sq m
  • 1 bedroom
  • Sleeps 3
  • 1 Queen Bed and 1 Double Sofa Bed

View all photos for Deluxe Suite, 1 Bedroom, Balcony, Ocean View

Room

Deluxe Suite, 1 Bedroom, Balcony, Ocean View

  • Ocean view
  • 74 sq m
  • 1 bedroom
  • Sleeps 6
  • 2 Queen Beds and 1 Double Sofa Bed

View all photos for Deluxe Suite, 1 Bedroom, Balcony

Room

Deluxe Suite, 1 Bedroom, Balcony

  • 74 sq m
  • 1 bedroom
  • Sleeps 6
  • 2 Queen Beds and 1 Double Sofa Bed

View all photos for Standard Studio, Balcony, Ocean View

A hotel room with a bed, a sofa, a nightstand, a lamp, a framed picture, and a wicker hanging light fixture.

Standard Studio, Balcony, Ocean View

  • Ocean view
  • 37 sq m
  • 1 bedroom
  • Sleeps 3
  • 1 Queen Bed and 1 Double Sofa Bed

View all photos for Deluxe Suite, 1 Bedroom, Balcony, Pool View

Room

Deluxe Suite, 1 Bedroom, Balcony, Pool View

  • 74 sq m
  • 1 bedroom
  • Sleeps 6
  • 2 Queen Beds and 1 Double Sofa Bed

View all photos for Standard Suite, 1 Bedroom, Balcony, Pool View

A bedroom with a bed, a nightstand, a lamp, a ceiling fan, and a wardrobe.

Standard Suite, 1 Bedroom, Balcony, Pool View

  • 74 sq m
  • 1 bedroom
  • Sleeps 6
  • 1 Queen Bed, 1 Double Sofa Bed and 1 Queen Sofa Bed

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About the area

Located on the waterfront, Caloosa Cove Resort by CoolVacay is in Matecumbe, a neighbourhood in Islamorada. Keys History & Discovery Center and History of Diving Museum are cultural highlights, and some of the area's landmarks include Indian Key Historic State Park and Hurricane Monument. Ready for a night out? Consider Lorelei Restaurant & Cabana Bar and Hog Heaven. Take the opportunity to explore the area for water adventures such as swimming. Visit our Islamorada travel guide
View more Condo rentals in Islamorada
Map
73801 Overseas Hwy, Islamorada, FL, 33036

What's nearby

  • A wooden deck with benches overlooking a clear blue sea.
    Anne's Beach
    7 min walk - 0.7 km
  • A marina with boats docked, a motel, and a cafe.
    Bud n' Mary's Dive Center
    10 min drive - 12.6 km
  • A waterfall at SeaWorld, with text reading "I eat the sea" and "Marine Mammal Park, Islamorada, Florida".
    Theater of the Sea
    17 min drive - 22.6 km
  • Sunset Drive Beach
    3 min walk - 0.3 km
  • Robbie’s of Islamorada
    6 min drive - 7.6 km

Getting around

  • Marathon, FL (MTH-Florida Keys Marathon)
    28 min drive

Restaurants

  • Hungry Tarpon Restaurant
    5 min drive
  • Habanos Oceanfront Dining
    2 min walk
  • Lazy Days Restaurant
    8 min drive
  • Papa Joe’s Waterfront
    8 min drive
  • Tiki Bar at Amara Cay Resort
    8 min drive

About this property

Caloosa Cove Resort by CoolVacay

  • Condo located in Matecumbe
  • Caloosa Cove Resort by CoolVacay provides amenities, such as a marina and a restaurant. Stay connected with free in-room WiFi.
  • You'll also enjoy perks such as:
    • An outdoor pool
    • Free self-parking
    • Smoke-free property, outdoor furniture and games
    • Barbecues, ATM/banking services and books
  • Room features
  • All guest rooms at Caloosa Cove Resort by CoolVacay feature perks, such as air conditioning and separate sitting areas, as well as amenities, such as free WiFi and dining tables.
  • Other conveniences in all rooms include:
    • Kitchens with blenders and toasters
    • 40-inch TVs with cable channels
    • Wardrobes/cupboards, balconies and separate sitting areas

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Frequently asked questions

Does Caloosa Cove Resort by CoolVacay have a pool?

Yes, this property has an outdoor pool.

Is Caloosa Cove Resort by CoolVacay pet-friendly?

No, pets are not allowed at this property.

How much is parking at Caloosa Cove Resort by CoolVacay?

Self-parking is free at this property.

What time is check-in at Caloosa Cove Resort by CoolVacay?

Check-in begins at 3:00 PM. Late check-in is available during limited hours.

What time is check-out at Caloosa Cove Resort by CoolVacay?

Checkout is at 10:00 AM.

Where is Caloosa Cove Resort by CoolVacay located?

Located in Matecumbe, this condo building is within a 10-minute walk of Sunset Drive Beach and Anne's Beach. Robbie’s of Islamorada and Indian Key Historic State Park are also within 6 miles (10 km).

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Reviews

Caloosa Cove Resort by CoolVacay Reviews

9.0

Wonderful

9.4

Cleanliness
Rating 10 - Excellent. 13 out of 17 reviews
Rating 8 - Good. 1 out of 17 reviews
Rating 6 - Okay. 1 out of 17 reviews
Rating 4 - Poor. 2 out of 17 reviews
Rating 2 - Terrible. 0 out of 17 reviews

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in
Great location, we will return
Stayed 2 nights in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy
Very clean efficiency with a full fridge, stove and oven. Grills by the water to cook your own catch or from the market down the road. Large pool, well maintained.
Stayed 2 nights in Oct 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy
Easy check in if you come After business hours. Kayaks and sport equipment available. Has a small beach which is unique to the Keys. Pool pretty much vacant at all times. Great views. Highly recommend.
Stayed 3 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy
We really enjoyed our stay here. We stayed in the family suite. Check-in process was a breeze. The staff were friendly. The rooms were clean, no off odors, beds were comfortable, plenty of space to move around and specially for the kiddos to play. I really enjoyed the balcony area. Although we had access to a kitchenette (with a full size fridge) I didn’t get to use it, but if I would’ve stayed longer I would have definitely taken advantage of it. A restaurant is accessible by a short walk from the hotel. Best part, bar next door right beside the beach. Drinks were delicious. The ambiance was great too. We had access to the pool. Kids had a blast. Laundry room accessible, with fair prices. Overall, we had a wonderful stay, I would definitely recommend. We will definitely come back to this place.
Stayed 1 night in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy
Lovely staff clean room great crowd all around great stay
Stayed 2 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy
We had a great stay! The view is amazing. You are right on the water. Pool was clean and heated. A couple of restaurants you can walk too. Will probably stay here again!
Stayed 2 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy
.
Stayed 2 nights in Aug 2026
Verified review

4/10 Poor

Disliked: Communication
They said there would be 2 beds, it was 1 bed and a pull out couch that was absolutely the worst pull out couch I’ve slept on and that is saying something. Pretty disappointing
Stayed 5 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy
Todo bueno y tranquilo
Stayed 3 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy
La propiedad me encantó se las recomiendo 100/100%
Stayed 2 nights in Apr 2026
Verified review

8/10 Good

Stayed 2 nights in Apr 2026