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Caloosa Cove Resort by CoolVacay

Property class: 3

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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 resort with a central swimming pool, multiple balconies, and palm trees.
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.

Reviews

9.0 out of 10
Wonderful

Popular amenities

  • Pool
  • Kitchen
  • Parking included
  • Free WiFi
  • Restaurant
  • 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
  • Free WiFi

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
  • Free WiFi

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
  • Free WiFi

View all photos for Deluxe Suite, 1 Bedroom, Balcony

Blackout drapes, iron/ironing board, WiFi (free), bed sheets

Deluxe Suite, 1 Bedroom, Balcony

  • 800 sq ft
  • 1 bedroom
  • Sleeps 6
  • 2 Queen Beds and 1 Double Sofa Bed
  • Free WiFi

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
  • Free WiFi

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
  • Free WiFi

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
  • Free WiFi

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

Blackout drapes, iron/ironing board, WiFi (free), bed sheets

Deluxe Suite, 1 Bedroom, Balcony, Pool View

  • 800 sq ft
  • 1 bedroom
  • Sleeps 6
  • 2 Queen Beds and 1 Double Sofa Bed
  • Free WiFi

View all photos for Deluxe Suite, 1 Bedroom, Balcony

Blackout drapes, iron/ironing board, WiFi (free), bed sheets

Deluxe Suite, 1 Bedroom, Balcony

  • 800 sq ft
  • 1 bedroom
  • Sleeps 6
  • 2 Queen Beds and 1 Double Sofa Bed
  • Free WiFi

View all photos for Deluxe Suite, 1 Bedroom, Balcony

Blackout drapes, iron/ironing board, WiFi (free), bed sheets

Deluxe Suite, 1 Bedroom, Balcony

  • Marina view
  • 800 sq ft
  • 1 bedroom
  • Sleeps 6
  • 2 Queen Beds and 1 Double Sofa Bed
  • Free WiFi

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
  • Free WiFi

View all photos for Deluxe Suite, 1 Bedroom, Balcony

Blackout drapes, iron/ironing board, WiFi (free), bed sheets

Deluxe Suite, 1 Bedroom, Balcony

  • 800 sq ft
  • 1 bedroom
  • Sleeps 6
  • 2 Queen Beds and 1 Double Sofa Bed
  • Free WiFi

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
  • Free WiFi

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
  • Free WiFi

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

Blackout drapes, iron/ironing board, WiFi (free), bed sheets

Deluxe Suite, 1 Bedroom, Balcony, Marina View

  • Marina view
  • 800 sq ft
  • 1 bedroom
  • Sleeps 6
  • 2 Queen Beds and 1 Double Sofa Bed
  • Free WiFi

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

Blackout drapes, iron/ironing board, WiFi (free), bed sheets

Deluxe Suite, 1 Bedroom, Balcony, Pool View

  • 800 sq ft
  • 1 bedroom
  • Sleeps 6
  • 2 Queen Beds and 1 Double Sofa Bed
  • Free WiFi

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

Blackout drapes, iron/ironing board, WiFi (free), bed sheets

Deluxe Suite, 1 Bedroom, Balcony, Marina View

  • Marina view
  • 800 sq ft
  • 1 bedroom
  • Sleeps 6
  • 2 Queen Beds and 1 Double Sofa Bed
  • Free WiFi

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
  • Free WiFi

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

Blackout drapes, iron/ironing board, WiFi (free), bed sheets

Deluxe Suite, 1 Bedroom, Balcony, Ocean View

  • Ocean view
  • 800 sq ft
  • 1 bedroom
  • Sleeps 6
  • 2 Queen Beds and 1 Double Sofa Bed
  • Free WiFi

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
  • Free WiFi

View all photos for Deluxe Suite, 1 Bedroom, Balcony

Blackout drapes, iron/ironing board, WiFi (free), bed sheets

Deluxe Suite, 1 Bedroom, Balcony

  • Marina view
  • 800 sq ft
  • 1 bedroom
  • Sleeps 6
  • 2 Queen Beds and 1 Double Sofa Bed
  • Free WiFi

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
  • Free WiFi

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

Blackout drapes, iron/ironing board, WiFi (free), bed sheets

Deluxe Suite, 1 Bedroom, Balcony, Ocean View

  • Ocean view
  • 800 sq ft
  • 1 bedroom
  • Sleeps 6
  • 2 Queen Beds and 1 Double Sofa Bed
  • Free WiFi

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

Blackout drapes, iron/ironing board, WiFi (free), bed sheets

Deluxe Suite, 1 Bedroom, Balcony, Pool View

  • 800 sq ft
  • 1 bedroom
  • Sleeps 6
  • 2 Queen Beds and 1 Double Sofa Bed
  • Free WiFi

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
  • Free WiFi

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

Blackout drapes, iron/ironing board, WiFi (free), bed sheets

Deluxe Suite, 1 Bedroom, Balcony, Ocean View

  • Ocean view
  • 800 sq ft
  • 1 bedroom
  • Sleeps 6
  • 2 Queen Beds and 1 Double Sofa Bed
  • Free WiFi

View all photos for Deluxe Suite, 1 Bedroom, Balcony

Blackout drapes, iron/ironing board, WiFi (free), bed sheets

Deluxe Suite, 1 Bedroom, Balcony

  • 800 sq ft
  • 1 bedroom
  • Sleeps 6
  • 2 Queen Beds and 1 Double Sofa Bed
  • Free WiFi

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
  • Free WiFi

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

Blackout drapes, iron/ironing board, WiFi (free), bed sheets

Deluxe Suite, 1 Bedroom, Balcony, Pool View

  • 800 sq ft
  • 1 bedroom
  • Sleeps 6
  • 2 Queen Beds and 1 Double Sofa Bed
  • Free WiFi

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
  • Free WiFi

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About the neighborhood

Islamorada

Located in Matecumbe within a 5-minute walk of Sunset Drive Beach, Caloosa Cove Resort by CoolVacay is within a 15-minute stroll of Anne's Beach. This 3-star condo building has 30 rooms and welcomes guests with a restaurant, a marina, and an outdoor pool.
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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
  • ‪Lazy Days Restaurant - ‬8 min drive
  • ‪Papa Joe’s Waterfront - ‬8 min drive
  • ‪Habanos Oceanfront Dining - ‬2 min walk
  • ‪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

Guests staying at Caloosa Cove Resort by CoolVacay enjoy access to a marina, an outdoor pool, and free WiFi in public areas. Free parking is available if you drive. Friendly staff can provide front-desk service during limited hours, and also offer advice about sightseeing. Additional amenities include an ATM, barbecue grills, and a picnic area.
Each condo is air-conditioned and features a kitchen and a balcony, and there's space to spread out with a sitting area. Guests can expect to find free WiFi and a 40-inch TV with cable channels. Other standard amenities include a sofa bed, a coffee maker, and a phone.
Recreational amenities at the condo include an outdoor pool.

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

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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

  • Bedsheets 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

  • This property doesn't allow pets

Property payment types

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
  • Check-in: 3:00 PM
  • Check-out: 10:00 AM
  • Minimum check-in age: 21
The front desk is available during limited hours. Driving? This property offers free parking.

We should mention

Details about charges, deposits, or other important information:

  • 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.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A credit card for incidental charges and a government-issued photo ID may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • This property accepts credit cards and debit cards. Cash is not accepted. 

Additional information about polices, regulations, and more:

  • There are no elevators.
  • No cribs or infant beds are available.
  • No rollaway or extra beds are available.

Frequently asked questions

What's there to see around Caloosa Cove Resort by CoolVacay?

This condo is situated in Matecumbe within a 10-minute walk of Anne's Beach and Sunset Drive Beach. You'll also find Robbie’s of Islamorada and Fiesta Key within a short drive.

Is there parking available at Caloosa Cove Resort by CoolVacay?

Yes, uncovered self parking is offered for free at the condo.

Does Caloosa Cove Resort by CoolVacay have a casino on the premises?

No, Caloosa Cove Resort by CoolVacay doesn't have a casino.

Will I find an indoor pool at Caloosa Cove Resort by CoolVacay?

No, this condo doesn't have an indoor pool; however, there is an outdoor pool.

Is Caloosa Cove Resort by CoolVacay a good place to stay for couples?

This waterfront condo offers plenty of amenities for couples including a restaurant, an outdoor pool, and a marina.

Are there hot tubs at Caloosa Cove Resort by CoolVacay?

No, this condo doesn't have a spa tub.

Does Caloosa Cove Resort by CoolVacay have a restaurant that serves breakfast?

No, Caloosa Cove Resort by CoolVacay doesn't have a restaurant that serves breakfast.

Does Caloosa Cove Resort by CoolVacay allow pets to stay free of charge?

No, pets aren't allowed at Caloosa Cove Resort by CoolVacay.

Are there connecting rooms at Caloosa Cove Resort by CoolVacay?

No, this condo doesn't feature connecting guestrooms.

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

The closest major airport to Caloosa Cove Resort by CoolVacay is Marathon, FL (MTH-Florida Keys Marathon), which is 22.3 mi away (28 minutes by car).

Are there rooms with balconies at Caloosa Cove Resort by CoolVacay?

Yes, every condo at Caloosa Cove Resort by CoolVacay comes with a balcony and some offer ocean views.

Caloosa Cove Resort by CoolVacay Reviews

Reviews

9.0

Wonderful

Rating 10 - Excellent. 8 out of 11 reviews
Rating 8 - Good. 1 out of 11 reviews
Rating 6 - Okay. 1 out of 11 reviews
Rating 4 - Poor. 1 out of 11 reviews
Rating 2 - Terrible. 0 out of 11 reviews

9.4/10

Cleanliness

Reviews

Verified review

10/10 Excellent

Dana

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

Marta

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

Kimberly

Stayed 2 nights in Apr 2026