Condo

Caloosa Cove Resort by CoolVacay

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Photo gallery for Caloosa Cove Resort by CoolVacay

An aerial view of a resort with a swimming pool, beach, and marina.
A modern kitchen with white cabinets, a dining area with a round table and chairs, and a large window providing a view of the outdoors.
A pool area with lounge chairs and umbrellas, overlooking the ocean.
A resort with a central swimming pool, multiple balconies, and palm trees.
An aerial view of a coastal resort with a marina, multiple buildings, and a large hotel labeled "CAYMAN COAST."

Reviews

9.2 out of 10
Wonderful

Highlights

  • Outdoor pool
    The outdoor pool is a refreshing retreat under the open sky - a rare gem in this area.
  • Discover nearby landmarks
    Walk to Anne's Beach

Popular amenities

  • Balcony
  • Restaurant
  • Outdoor pool
  • Barbecue
  • Air-conditioning
  • Free Wi-Fi in public areas

Explore the area

View map
73801 Overseas Hwy, Islamorada, FL, 33036
  • Place, Sunset Drive Beach
    ‪3 min walk‬
  • Place, Anne's Beach
    ‪7 min walk‬
  • Place, Robbie’s of Islamorada
    ‪6 min drive‬
  • Airport, Marathon, FL (MTH-Florida Keys Marathon)
    ‪33 min drive‬

Choose your unit

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

Room

  • Sleeps 2

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About this property

Caloosa Cove Resort by CoolVacay

Along with a marina, this smoke-free condo building has an outdoor pool and a restaurant. Free WiFi in public areas and free self parking are also provided. Additionally, barbecues, a picnic area and ATM/banking services are on-site. Each condo provides a sofa bed and a sitting area, plus a kitchen and a TV with cable channels. Guests can appreciate conveniences, such as a coffee/tea maker and a dining table, and other amenities include free WiFi and a balcony.
Caloosa Cove Resort by CoolVacay offers 30 air-conditioned accommodations with coffee/tea makers and an iron/ironing board. Rooms open to balconies. This accommodation has separate sitting areas and is furnished with double sofa beds and dining tables. Accommodation at this 3-star condo has kitchens.

This Islamorada condo provides complimentary wireless Internet access, with a speed of 25+ Mbps. Cable televisions are provided.

Recreational amenities at the condo include an outdoor pool.

The recreational activities listed below are available either on-site or nearby; fees may apply.

Policies

Check-in

Check-in time starts at 3:00 PM
Late check-in subject to availability
Minimum check-in age - 21

Check-out

Check-out before 10:00 AM

Special check-in instructions

The front desk is open daily from 8:00 AM - 4:00 PM
Guests will receive an email within 2 weeks before arrival with check-in instructions; front desk staffed during limited hours
If you are planning to arrive after 4:00 PM please contact the property in advance using the information on the booking confirmation
Information provided by the property may be translated using automated translation tools

Access methods

Front desk (limited hours)

Pets

Pets not allowed

Children and extra beds

Children are welcome
Rollaway/extra beds are not available.
Cots (infant beds) are not available

Payment types

American ExpressDiscoverMastercardVisa

Important information

You need to know

Property # 126855425
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
This property accepts credit cards and debit cards; cash is not accepted
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room

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).

Caloosa Cove Resort by CoolVacay Reviews

Reviews

9.2

Wonderful

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 10 out of 13 reviews
Rating 8 - Good. 1 out of 13 reviews
Rating 6 - Okay. 1 out of 13 reviews
Rating 4 - Poor. 1 out of 13 reviews
Rating 2 - Terrible. 0 out of 13 reviews

9.4/10

Cleanliness

9.4/10

Check-in

9.0/10

Communication

9.2/10

Listing accuracy

Reviews

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
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
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

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