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Caloosa Cove Resort by CoolVacay

Property class: 3
3-star condo in Matecumbe

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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 pool area with lounge chairs and umbrellas, overlooking the ocean.
An aerial view of a coastal resort with a marina, multiple buildings, and a large hotel labeled "CAYMAN COAST."
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 resort with a central swimming pool, multiple balconies, and palm trees.

Reviews

9.2 out of 10
Wonderful

Popular amenities

  • Kitchen
  • Parking included
  • Free WiFi
  • Air conditioning

Explore the area

View in a 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

Room options

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

  • 400 sq ft
  • 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
  • 400 sq ft
  • 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

  • 400 sq ft
  • 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

  • 800 sq ft
  • 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
  • 400 sq ft
  • 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
  • 400 sq ft
  • 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

  • 800 sq ft
  • 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

  • 800 sq ft
  • 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

  • 800 sq ft
  • 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
  • 800 sq ft
  • 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

  • 400 sq ft
  • 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

  • 800 sq ft
  • 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

  • 800 sq ft
  • 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
  • 800 sq ft
  • 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
  • 800 sq ft
  • 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

  • 800 sq ft
  • 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
  • 800 sq ft
  • 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

  • 400 sq ft
  • 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
  • 800 sq ft
  • 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
  • 400 sq ft
  • 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
  • 800 sq ft
  • 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
  • 800 sq ft
  • 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
  • 800 sq ft
  • 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

  • 800 sq ft
  • 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
  • 400 sq ft
  • 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
  • 800 sq ft
  • 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

  • 800 sq ft
  • 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
  • 400 sq ft
  • 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

  • 800 sq ft
  • 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

  • 800 sq ft
  • 1 bedroom
  • Sleeps 6
  • 1 Queen Bed, 1 Double Sofa Bed and 1 Queen Sofa Bed

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  • Pool
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9.6 out of 10, Exceptional, 83 reviews
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About the neighborhood

Islamorada

Matecumbe stay.Within a 10-minute walk of this Matecumbe condo, you'll find Sunset Drive Beach and Anne's Beach. Robbie’s of Islamorada and Indian Key Historic State Park are also within 6 miles (10 km).
View more Condo Rentals in IslamoradaOpens in a new window

What's nearby

  • Sunset Drive Beach - 3 min walk - 0.2 miles
  • Anne's Beach - 7 min walk - 0.4 miles
  • Robbie’s of Islamorada - 6 min drive - 4.8 miles
  • Bud n' Mary's Dive Center - 10 min drive - 7.8 miles
  • Theater of the Sea - 17 min drive - 14.0 miles

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

Entire place

You'll have the entire condo to yourself and will only share it with other guests in your party.

Caloosa Cove Resort by CoolVacay

3-star condo in Matecumbe
There's a restaurant on site. Public spaces have free WiFi. Caloosa Cove Resort by CoolVacay offers its guests a marina and an outdoor pool. Caloosa Cove Resort by CoolVacay also features barbecue grills, a picnic area, and an ATM. Self parking is free.

This 3-star Islamorada condo is smoke free.

  • 30 guestrooms or units
  • Front desk (limited hours)
  • BBQ grill(s)
  • Outdoor picnic space
  • ATM
  • No smoking on site
  • Dining venue
Caloosa Cove Resort by CoolVacay offers 30 air-conditioned accommodations with coffee/tea makers and irons/ironing boards. Rooms open to balconies. Accommodations have separate sitting areas and are furnished with double sofa beds and dining tables. Accommodations at this 3-star condo have kitchens.

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

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Amara Cay Resort
Matecumbe
  • On private beach
  • Pool
  • Pet friendly
  • Restaurant
4.4 out of 5, Excellent, 1,325 reviews
$220 nightly
The price is $248
Nov 15 - Nov 16
Total with taxes and fees
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Property amenities

Beach

  • Sandy beach nearby

Pool/Spa

  • Outdoor pool

Internet

  • Available in the condo: Free WiFi
  • Available in some public areas: Free WiFi

Parking and transportation

  • Free uncovered self parking on site

Kitchen

  • Blender
  • Coffee/tea maker
  • Toaster

Dining

  • A restaurant
  • Dining table

Bedrooms

  • Bed sheets provided
  • Double sofa bed

Bathroom

  • Towels provided

Living spaces

  • Dining table
  • Separate sitting area

Entertainment

  • 40-inch TV with cable channels
  • Books
  • Games

Outdoor areas

  • Balcony
  • Barbecue grill
  • Marina
  • Outdoor furniture
  • Picnic area

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • No elevator
  • Smoking not allowed

Services and conveniences

  • ATM
  • Blackout drapes
  • Iron/ironing board
  • Limited-hour front desk
  • Phone

Location highlights

  • On the waterfront

Things to do

  • Fishing
  • Swimming nearby

Safety features

  • Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
  • Smoke detector not reported (host has not indicated whether there is a smoke detector on the property)

General

  • 30 units

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

  • No pets allowed

Children and extra beds

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

Property payment types

  • American Express
  • Discover
  • Mastercard
  • Visa

Important information

You need to know

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, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
Charges for extra guests may apply and vary according to property policy.
A credit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children. If you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room. This property accepts Visa, Mastercard, American Express, Discover, and debit cards. Cash is not accepted. 

Frequently asked questions

How close is Caloosa Cove Resort by CoolVacay to the airport?

Caloosa Cove Resort by CoolVacay is 22.3 mi (28-min drive) away from the Marathon, FL (MTH-Florida Keys Marathon) airport, the closest popular airport to the property.

Does Caloosa Cove Resort by CoolVacay have an airport shuttle?

Airport shuttle services are not available at Caloosa Cove Resort by CoolVacay.

How close is Caloosa Cove Resort by CoolVacay to the beach?

This condo is a short 3-minute walk from Sunset Drive Beach and 6-minute walk from Anne's Beach. Don't forget your sunscreen!

Does Caloosa Cove Resort by CoolVacay offer free breakfast?

Caloosa Cove Resort by CoolVacay does not offer free breakfast.

Is there a casino at Caloosa Cove Resort by CoolVacay?

No, there is no casino at this condo.

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

Check-in begins at 3:00 PM.

Is there free parking at Caloosa Cove Resort by CoolVacay?

This condo offers free self parking.

Does Caloosa Cove Resort by CoolVacay have a pool?

Caloosa Cove Resort by CoolVacay features an outdoor pool.

Does Caloosa Cove Resort by CoolVacay have a restaurant?

Yes, there is a restaurant on site.

Does Caloosa Cove Resort by CoolVacay have a spa?

There are no spa services available at this condo.

How close is Caloosa Cove Resort by CoolVacay to downtown Islamorada?

Caloosa Cove Resort by CoolVacay is 8.6 mi away from Islamorada.

Caloosa Cove Resort by CoolVacay Reviews

Reviews

9.2

Wonderful

Rating 10 - Excellent. 15 out of 19 reviews
Rating 8 - Good. 1 out of 19 reviews
Rating 6 - Okay. 1 out of 19 reviews
Rating 4 - Poor. 2 out of 19 reviews
Rating 2 - Terrible. 0 out of 19 reviews

9.4/10

Cleanliness

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
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

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
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
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

10/10 Excellent

Stayed 2 nights in Aug 2026
Verified review

6/10 Okay

Stayed 2 nights in Jun 2026
Verified review

8/10 Good

Stayed 2 nights in Apr 2026

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